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Below you will find dozens of scientific research articles related to Mangosteen and Xanthones, I've highlighted the Key Words for you in red...
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.·:*¨¨*:·. The Amazing Mangosteen Tree .·:*¨¨*:·.
J Ethnopharmacol. 2004 Jan;90(1):161-6.
Antiproliferation, antioxidation and induction of apoptosis by Garcinia mangostana (mangosteen) on SKBR3 human breast cancer cell line.
Moongkarndi P, Kosem N, Kaslungka S, Luanratana O, Pongpan N, Neungton N.
Department of Microbiology, Faculty of Pharmacy, Mahidol University, Sri Ayudthaya Road, Rajdhevee, Bangkok 10400, Thailand. pypmk@mahidol.ac.th
This study was designed to determine the antiproliferative, apoptotic and antioxidative properties of crude methanolic extract (CME) from the pericarp of Garcinia mangostana (family Guttiferae) using human breast cancer (SKBR3) cell line as a model system. SKBR3 cells were cultured in the presence of CME at various concentrations (0-50 microg/ml) for 48 h and the percentage of cell viability was evaluated by 3-(4,5-dimethylthiazol-2-yl)-2,5-di phenyl tetrazolium bromide (MTT) assay. CME showed a dose-dependent inhibition of cell proliferation with ED(50) of 9.25+/-0.64 microg/ml. We found that antiproliferative effect of CME was associated with apoptosis on breast cancer cell line by determinations of morphological changes and oligonucleosomal DNA fragments. In addition, CME at various concentrations and incubation times were also found to inhibit ROS production. These investigations suggested that the methanolic extract from the pericarp of Garcinia mangostana had strong antiproliferation, potent antioxidation and induction of apoptosis. Thus, it indicates that this substance can show different activities and has potential for cancer chemoprevention which were dose dependent as well as exposure time dependent.
PMID: 14698525 [PubMed - indexed for MEDLINE]
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J Nat Prod. 2003 Aug;66(8):1124-7.
Induction of apoptosis by xanthones from mangosteen in human leukemia cell lines.
Matsumoto K, Akao Y, Kobayashi E, Ohguchi K, Ito T, Tanaka T, Iinuma M, Nozawa Y.
Gifu International Institute of Biotechnology, 1-1 Naka-Fudogaoka, Kakamigahara, Gifu 504-0838, Japan. kmatsumoto@giib.or.jp
We examined the effects of six xanthones from the pericarps of mangosteen, Garcinia mangostana, on the cell growth inhibition of human leukemia cell line HL60. All xanthones displayed growth inhibitory effects. Among them, alpha-mangostin showed complete inhibition at 10 microM through the induction of apoptosis.
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Chem Pharm Bull (Tokyo). 2003 Jul;51(7):857-9.
Antimycobacterial activity of prenylated xanthones from the fruits of Garcinia mangostana.
Suksamrarn S, Suwannapoch N, Phakhodee W, Thanuhiranlert J, Ratananukul P, Chimnoi N, Suksamrarn A.
Department of Chemistry, Faculty of Science, Srinakharinwirot University, Bangkok, Thailand. sunit@swu.ac.th
Prenylated xanthones, isolated from the fruit hulls and the edible arils and seeds of Garcinia mangostana, were tested for their antituberculosis potential. Alpha- and beta-mangostins and garcinone B exhibited strong inhibitory effect against Mycobacterium tuberculosis with the minimum inhibitory concentration (MIC) value of 6.25 microg/ml. Tri- and tetra-oxygenated xanthones with di-C5 units or with a C5 and a modified C5 groups are essential for high activities. Substitution in the A and C rings has been shown to modify the bioactivity of the compounds.
PMID: 12843596 [PubMed - indexed for MEDLINE]
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Planta Med. 2002 Nov;68(11):975-9.
Garcinone E, a xanthone derivative, has potent cytotoxic effect against hepatocellular
carcinoma cell lines.
Ho CK, Huang YL, Chen CC.
Department of Medical Research & Education, Veterans General Hospital, Taipei, ROC.
Treatment of hepatocellular carcinomas (HCCs) with chemotherapy has generally been disappointing and it is most desirable to have more effective new drugs. We extracted and purified 6 xanthone compounds from the rinds (peel) of the fruits of Garcinia mangostana L., using partitioned chromatography and then tested the cytotoxic effects of these compounds on a panel of 14 different human cancer cell lines including 6 hepatoma cell lines, based on the MTT method. Several commonly used chemotherapeutic agents were included in the assay to determine the relative potency of the potential new drugs. Our results have shown that one of the xanthone derivatives which could be identified as garcinone E has potent cytotoxic effect on all HCC cell lines as well as on the other gastric and lung cancer cell lines included in the screen. We suggest that garcinone E may be potentially useful for the treatment of certain types of cancer.
PMID: 12451486 [PubMed - indexed for MEDLINE]
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Biol Pharm Bull. 2002 Sep;25(9):1137-41.
Inhibitions of histamine release and prostaglandin E2 synthesis by mangosteen, a Thai medicinal plant.
Nakatani K, Atsumi M, Arakawa T, Oosawa K, Shimura S, Nakahata N, Ohizumi Y.
Department of Pharmaceutical Molecular Biology, Graduate School of Pharmaceutical Sciences, Tohoku University, Sendai, Japan.
The fruit hull of mangosteen, Garcinia mangostana L. has been used as a Thai indigenous medicine for many years. However, its mechanism of action as a medicine has not been elucidated. The present study was undertaken to examine the effects of mangosteen extracts (100% ethanol, 70% ethanol, 40% ethanol and water) on histamine release and prostaglandin E2 synthesis. We found that the 40% ethanol extract of mangosteen inhibited IgE-mediated histamine release from RBL-2H3 cells with greater potency than the water extract of Rubus suavissimus that has been used as an anti-allergy crude drug in Japan. All extracts of mangosteen potently inhibited A23187-induced prostaglandin E2 synthesis in C6 rat glioma cells, while the water extract of Rubus suavissimus had no effect. The 40% ethanol extract of mangosteen inhibited the prostaglandin E2 synthesis in a concentration-dependent manner with relatively lower concentrations than the histamine release. In addition, passive cutaneous anaphylaxis (PCA) reactions in rats were significantly inhibited by this ethanol extract as well as by the water extract of Rubus suavissimus. These results suggest that the 40% ethanol extract of mangosteen has potent inhibitory activities of both histamine release and prostaglandin E2 synthesis.
PMID: 12230104 [PubMed - indexed for MEDLINE]
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Biochem Pharmacol. 2002 Jan 1;63(1):73-9.
Inhibition of cyclooxygenase and prostaglandin E2 synthesis by gamma-mangostin, a xanthone derivative in mangosteen, in C6 rat glioma cells.
Nakatani K, Nakahata N, Arakawa T, Yasuda H, Ohizumi Y.
Department of Pharmaceutical Molecular Biology, Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba, Aramaki, Aoba-ku, 980-8578, Sendai, Japan.
The fruit hull of mangosteen, Garcinia mangostana L., has been used for many years as a medicine for treatment of skin infection, wounds, and diarrhea in Southeast Asia. In the present study, we examined the effect of gamma-mangostin, a tetraoxygenated diprenylated xanthone contained in mangosteen, on arachidonic acid (AA) cascade in C6 rat glioma cells. gamma-Mangostin had a potent inhibitory activity of prostaglandin E2 (PGE2) release induced by A23187, a Ca2+ ionophore. The inhibition was concentration-dependent, with the IC50 value of about 5 microM. gamma-Mangostin had no inhibitory effect on A23187-induced phosphorylation of p42/p44 extracellular signal regulated kinase/mitogen-activated protein kinase or on the liberation of [14C]-AA from the cells labeled with [14C]-AA. However, gamma-mangostin concentration-dependently inhibited the conversion of AA to PGE2 in microsomal preparations, showing its possible inhibition of cyclooxygenase (COX). In enzyme assay in vitro, gamma-mangostin inhibited the activities of both constitutive COX (COX-1) and inducible COX (COX-2) in a concentration-dependent manner, with the IC50 values of about 0.8 and 2 microM, respectively. Lineweaver-Burk plot analysis indicated that gamma-mangostin competitively inhibited the activities of both COX-1 and -2. This study is a first demonstration that gamma-mangostin, a xanthone derivative, directly inhibits COX activity.
PMID: 11754876 [PubMed - indexed for MEDLINE]
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J Med Assoc Thai. 1997 Sep;80 Suppl 1:S149-54.
Immunopharmacological activity of polysaccharide from the pericarb of mangosteen garcinia: phagocytic intracellular killing activities.
Chanarat P, Chanarat N, Fujihara M, Nagumo T.
Department of Clinical Microscopy, Faculty of Associated Medical Sciences, Chiang Mai University, Thailand.
Polysaccharides from the pericarbs of mangosteen, Garcinia mangostana Linn., was obtained by treating the dried ground pericarbs with hot water followed by ethanol precipitation (M fraction). The extract was fractionated by anion exchange chromatography on a DEAE-cellulose column as MDE1-5 fractions. The fractions of MDE3 and MDE4 composed of mainly D-galacturonic acid and a small amount of neutral sugar (L-arabinose as the major one and L-rhamnose and D-galactose as the minor ones) were studied for immunopharmacological activities by phagocytic test to intracellular bacteria (Salmonella enteritidis) and nitroblue tetrazolium (NBT) and superoxide generation tests. The results showed that the number of S. enteritidis in cultured monocyte with extract of pericarb of mangosteen (MDE3) was killed. Activating score (mean +/- SD) of NBT test of 100 polymorphonuclear phagocytic cells were 145 +/- 78, 338 +/- 58, 222 +/- 73, 209 +/- 77, 211 +/- 63, 372 +/- 19, 369 +/- 20, 355 +/- 34 in normal saline control, phorbol myristate acetate (PMA), MDE3, MDE4, indomethacin (I), PMA + MDE3, PMA + MDE4 and PMA + I, respectively. Superoxide generation test was also done by color reduction of cytochrome c. Both MDE3 and MDE4 stimulate superoxide production. The number of S. enteritidis in cultured monocyte with extract of pericarb of mangosteen was killed. This paper suggests that polysaccharides in the extract can stimulate phagocytic cells and kill intracellular bacteria (S. enteritidis).
PMID: 9347663 [PubMed - indexed for MEDLINE]
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Planta Med. 1996 Oct;62(5):471-2. Healing Properties of Xanthones
Histaminergic and serotonergic receptor blocking substances from the medicinal plant Garcinia mangostana.
Chairungsrilerd N, Furukawa K, Ohta T, Nozoe S, Ohizumi Y.
A crude methanolic extract of the fruit hull of Mangosteen, Garcinia mangostana L. inhibited the contractions of isolated thoracic rabbit aorta induced by histamine and serotonin. The extract of the fruit hull has been fractionated by silica gel chromatography, monitoring the pharmacological activity to give alpha- and gamma-mangostin. On the basis of pharmacological data, it is suggested that alpha-mangostin and gamma-mangostin are a histaminergic and a serotonergic receptor blocking agent, respectively.
Publication Types:
• Letter
PMID: 8923814 [PubMed - indexed for MEDLINE]
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Yakugaku Zasshi. 2004 Jul;124(7):417-24.
Search for constituents with neurotrophic factor-potentiating activity from the medicinal plants of paraguay and Thailand.
Li Y, Ohizumi Y.
Department of Pharmaceutical Molecular Biology, Graduate School of Pharmaceutical Sciences, Tohoku University.
20 medicinal plants of Paraguay and 3 medicinal plants of Thailand were examined on nerve growth factor (NGF)-potentiating activities in PC12D cells. The trail results demonstrated that the methanol extracts of four plants, Verbena littoralis, Scoparia dulcis, Artemisia absinthium and Garcinia xanthochymus, markedly enhanced the neurite outgrowth induced by NGF from PC12D cells. Furthermore, utilizing the bioactivity-guided separation we successfully isolated 32, 4 and 5 constituents from V. littoralis, S. dulcis and G. xanthochymus, respectively, including nine iridoid and iridoid glucosides (1-9), two dihydrochalcone dimers (10 and 11), two flavonoids and three flavonoid glycosides (12-16), two sterols (17 and 18), ten triterpenoids (19-28), five xanthones (29-33), one naphthoquinone (34), one benzenepropanamide (35), four phenylethanoid glycosides (36-39) and two other compounds (40 and 41). Among which, 15 compounds (1-4, 10-11, 14-18, 29-31 and 34) were new natural products. The results of pharmacological trails verified that littoralisone (1), gelsemiol (5), 7a-hydroxysemperoside aglucone (6), verbenachalcone (10), littorachalcone (11), stigmast-5-ene 3beta,7alpha,22alpha-triol (18), ursolic acid (19), 3beta-hydroxyurs-11-en-28,13beta-olide (24), oleanolic acid (25), 2alpha,3beta-dihydroxyolean-12-en-28-oic acid (26), 1,4,5,6-tetrahydroxy-7,8-di(3-methylbut-2-enyl)xanthone (29), 1,2,6-trihydroxy-5-methoxy-7-(3-methylbut-2-enyl)xanthone (30), 1,3,5,6-tetrahydroxy-4,7,8-tri(3-methyl-2-butenyl)xanthone (31), 12b-hydroxy-des-D-garcigerrin A (32), garciniaxanthone E (33) and (4R)-4,9-dihydroxy-8-methoxy-alpha-lapachone (34) elicited marked enhancement of NGF-mediated neurite outgrowth in PC12D cells. These substances may contribute to the basic study and the medicinal development for the neurodegenerative disorder.
PMID: 15235225 [PubMed - in process]
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Cardiovasc Drug Rev. 2004 Summer;22(2):91-102.
Pharmacological effects of xanthones as cardiovascular protective agents.
Jiang DJ, Dai Z, Li YJ.
Department of Pharmacology, School of Pharmaceutical Sciences, Central South University, Xiang-Ya Road #90, Changsha 410078, China.
Many epidemiological studies indicate that consumption of dietary polyphenolic compounds is beneficial in the prevention of cardiovascular diseases. Xanthones are a class of polyphenolic compounds that commonly occur in plants and have been shown to have extensive biological and pharmacological activities. Recently, the pharmacological properties of xanthones in the cardiovascular system have attracted great interest. Xanthones and xanthone derivatives have been shown to have beneficial effects on some cardiovascular diseases, including ischemic heart disease, atherosclerosis, hypertension and thrombosis. The protective effects of xanthones in the cardiovascular system may be due to their antioxidant, antiinflammatory, platelet aggregation inhibitory, antithrombotic and/or vasorelaxant activities. In particular, the antagonism of endogenous nitric oxide synthase inhibitors by xanthones may represent the basis for improved endothelial function and for reduction of events associated with atherosclerosis.
PMID: 15179447 [PubMed - in process]
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J Pharmacol Sci. 2004 May;95(1):33-40.
Alpha-mangostin induces Ca(2+)-ATPase-dependent apoptosis via mitochondrial pathway in PC12 cells.
Sato A, Fujiwara H, Oku H, Ishiguro K, Ohizumi Y.
Department of Pharmaceutical Molecular Biology, Graduate School of Pharmaceutical Sciences, Tohoku University, Sendai, Japan.
We investigated the cell death effects of eight xanthones on PC12 rat pheochromocytoma cells. Among these compounds, alpha-mangostin, from the fruit hull of Garcinia mangostana L., had the most potent effect with the EC(50) value of 4 microM. Alpha-mangostin-treated PC12 cells demonstrated typical apoptotic DNA fragmentation and caspase-3 cleavage (equivalent to activation). The flow cytometric analysis indicated that this compound induced apoptosis in time-and concentration-dependent manners. Alpha-mangostin showed the features of the mitochondrial apoptotic pathway such as mitochondrial membrane depolarization and cytochrome c release. Furthermore, alpha-mangostin inhibited the sarco(endo)plasmic reticulum Ca(2+)-ATPase markedly. There was a correlation between the Ca(2+)-ATPase inhibitory effects and the apoptotic effects of the xanthone derivatives. On the other hand, c-Jun NH(2)-terminal kinase (JNK/SAPK), one of the signaling molecules of endoplasmic reticulum (ER) stress, was activated with alpha-mangostin treatment. These results suggest that alpha-mangostin inhibits Ca(2+)-ATPase to cause apoptosis through the mitochondrial pathway.
PMID: 15153648 [PubMed - in process]
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Bioorg Med Chem. 2003 Nov 17;11(23):5171-7.
Relationship between protective effect of xanthone on endothelial cells and endogenous nitric oxide synthase inhibitors.
Jiang DJ, Hu GY, Jiang JL, Xiang HL, Deng HW, Li YJ.
Department of Pharmacology, School of Pharmaceutical Sciences, Central South University, Changsha 410078, China.
1,3,5,6-tetrahydroxyxanthone was synthesized. The relationship between protective effect of xanthone on endothelial cells and endogenous nitric oxide synthase inhibitors was investigated. Endothelial cells were treated with ox-LDL (100 microg/mL) for 48 h. Adhesion of monocytes to endothelial cells and release of lactate dehydrogenase (LDH) was determined. Levels of tumor necrosis factor-alpha (TNF-alpha), monocyte chemoattractant protein-1 (MCP-1), nitric oxide (NO) and asymmetric dimethylarginine (ADMA, an endogenous inhibitor of nitric oxide synthase) in conditioned medium and activity of dimethylarginine dimethylaminohydrolase (DDAH) in endothelial cells were measured. Incubation of endothelial cells with ox-LDL (100 microg/mL) for 48 h markedly enhanced the adhesion of monocytes to endothelial cells, increased the release of LDH, the levels of TNF-alpha, MCP-1 and ADMA, and decreased the content of NO and the activity of DDAH. Xanthone (1,3,5,6-tetrahydroxyxanthone) (1, 3 or 10 micromol/L) significantly inhibited the increased adhesion of monocytes to endothelial cells and attenuated the increased levels of LDH, MCP-1 and ADMA induced by ox-LDL. Xanthone (1,3,5,6-tetrahydroxyxanthone) (3 or 10 micromol/L) significantly attenuated the increased level of TNF-alpha and decreased level of NO and activity of DDAH by ox-LDL. The present results suggest that xanthone (1,3,5,6-tetrahydroxyxanthone) preserves endothelial cells and inhibits the increased adhesion of monocytes to endothelial cells induced by ox-LDL, and that the protective effect of xanthone (1,3,5,6-tetrahydroxyxanthone) on endothelial cells is related to reduction of ADMA concentration via increase of DDAH activity.
PMID: 14604680 [PubMed - in process]
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Chem Pharm Bull (Tokyo). 2003 Nov;51(11):1332-4.
Prenylated xanthones from Garcinia xanthochymus.
Chanmahasathien W, Li Y, Satake M, Oshima Y, Ishibashi M, Ruangrungsi N, Ohizumi Y.
Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba, Aramaki, Aoba-ku, Sendai 980-8578, Japan.
A new prenylated xanthone, 1,3,5,6-tetrahydroxy-4,7,8-tri(3-methyl-2-butenyl)xanthone (1), was isolated from the wood of Garcinia xanthochymus together with a known xanthone, garciniaxanthone E (2). Their structures were determined by spectroscopic analysis. Compounds 1 (3 microM) and 2 (10 microM) elicited marked enhancement of nerve growth factor-mediated neurite outgrowth in PC12D cells.
PMID: 14600386 [PubMed - indexed for MEDLINE]
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Pol J Pharmacol. 2003 May-Jun;55(3):461-5.
Central activity of new xanthone derivatives with chiral center in some pharmacological tests in mice.
Jastrzebska-Wiesek M, Librowski T, Czarnecki R, Marona H, Nowak G.
Department of Pharmacodynamics, Jagiellonian University, Medical College, Medyczna 9, PL 30-688 Krakow, Poland.
The study was designed to investigate some central effects of chiral xanthone derivatives [(R,S)-2-N-(6-chloro-2-xanthonemethyl)-amino-1-propanol - MH-31, R enantiomer - MH-32 and S enantiomer - MH-33] in mice. The effects of these chiral compounds were examined in picrotoxin-induced seizures, spontaneous locomotor activity and chimney tests. The tested compounds demonstrated variable influence on the central nervous system in mice. The compound MH-32 exhibits anticonvulsant activity in picrotoxin-induced seizures, whereas MH-31 and its R enantiomer--compound MH-32 demonstrated antidepressant-like activity in the forced swimming test. Moreover, all tested xanthones reduced the locomotor activity in mice. The obtained results indicate the importance to examine pharmacologically enantiomers rather than only racemic mixtures of newly synthesized compounds.
PMID: 14506327 [PubMed - indexed for MEDLINE]
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Bioorg Med Chem. 2002 Dec;10(12):3725-30.
Xanthones as inhibitors of growth of human cancer cell lines and their effects on the proliferation of human lymphocytes in vitro.
Pedro M, Cerqueira F, Sousa ME, Nascimento MS, Pinto M.
Centro de Estudos de Quimica Organica, Fitoquimica e Farmacologia da Universidade do Porto, Faculdade de Farmacia, Porto, Portugal. madalena@ff.up.pt
Twenty-seven oxygenated xanthones have been assessed for their capacity to inhibit in vitro the growth of three human cancer cell lines, MCF-7 (breast cancer), TK-10 (renal cancer) and UACC-62 (melanoma). The effect of these xanthones on the proliferation of human T-lymphocytes was also evaluated. Differences on their potency towards the effect on the growth of the human cancer cell lines as well as on the proliferation of human T-lymphocytes can be ascribed to the nature and positions of the substituents on the xanthonic nucleus.
PMID: 12413829 [PubMed - indexed for MEDLINE]
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J Nat Prod. 2002 May;65(5):761-3.
Xanthones from the green fruit hulls of Garcinia mangostana.
Suksamrarn S, Suwannapoch N, Ratananukul P, Aroonlerk N, Suksamrarn A.
Department of Chemistry, Faculty of Science, Srinakharinwirot University, Bangkok 10110, Thailand. sunit@psm.swu.ac.th
Three new xanthones, mangostenol (1), mangostenone A (2), and mangostenone B (3), were isolated from the green fruit hulls of Garcinia mangostana, along with the known xanthones, trapezifolixanthone, tovophyllin B (4), alpha- and beta-mangostins, garcinone B, mangostinone, mangostanol, and the flavonoid epicatechin. The structures of the new xanthones were elucidated by analysis of their spectroscopic data.
PMID: 12027762 [PubMed - indexed for MEDLINE]
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Planta Med. 2002 Jan;68(1):86-7.
Inhibition of HIV-1 reverse transcriptase and HIV-1 replication by Calophyllum coumarins and xanthones.
Dharmaratne HR, Tan GT, Marasinghe GP, Pezzuto JM.
1 Natural Products Programme, Institute of Fundamental Studies, Kandy, Sri Lanka. hrwd13@hotmail.com
As part of our continuing study on the Calophyllum species, a number of coumarins, xanthones and chromene acids from different Calophyllum species of Sri Lanka were tested for inhibitory activity against the HIV-1 and its virally-encoded reverse transcriptase (RT). These compounds were found to be inactive in both the HIV-1 RT and whole virus systems. In contrast, cordatolide A and B demonstrated IC(50) values of 19.3 and 11.7 microM, respectively, against HIV-1 replication in a novel green fluorescent protein (GFP)-based reporter cell assay (HOG.R5).
Publication Types:
• Letter
PMID: 11842340 [PubMed - indexed for MEDLINE]
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Bioorg Med Chem. 2002 Mar;10(3):567-72.
Antihypertensive and vasorelaxing activities of synthetic xanthone derivatives.
Wang LW, Kang JJ, Chen IJ, Teng CM, Lin CN.
School of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan 807, ROC.
A series of xanthones and xanthonoxypropanolamines have been synthesized. The activity of compounds on cardiovascular system was evaluated. All the compounds tested exhibited effective hypotensive activity in anesthetized rats. An oxypropanolamine side chain substituted at the C-3 position of the xanthone nucleus significantly enhanced the hypotensive activity. In rat thoracic aorta, all the compounds tested significantly depressed the contractions induced by Ca(2+) (1.9mM) in high K+(80mM) medium and the phasic and tonic contractions caused by norepinephrine (3 microM). In the rat thoracic aorta, the phenylephrine- and high K+ -induced 45Ca(2+) influx were both inhibited by a selective xanthone derivative, 13. In addition to the previously reported result of 13, evaluated as beta adrenoceptor blocker, the depressor and bradycardia effects of 9 are independent of the parasympathetic passway. These results suggest that 13 showed inhibitory effects on the contractile response caused by high K+ and norepinephrine in rat thoracic aorta are mainly due to inhibition of Ca(2+) influx through both voltage-dependent and receptor-operated Ca(2+) channels. The vasodilating properties of 13 is due to its calcium channel and beta adrenergic blocking effects.
PMID: 11814844 [PubMed - indexed for MEDLINE]
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Antimicrob Agents Chemother. 2002 Jan;46(1):144-50.
Optimization of xanthones for antimalarial activity: the 3,6-bis-omega-diethylaminoalkoxyxanthone series.
Kelly JX, Winter R, Peyton DH, Hinrichs DJ, Riscoe M.
Department of Chemistry, Portland State University, Portland, Oregon 97207-0751, USA.
Hydroxyxanthones have been identified as novel antimalarial agents. The compounds are believed to exert their activity by complexation to heme and inhibition of hemozoin formation. Modification of the xanthone structure was pursued to improve their antimalarial activity. Attachment of R-groups bearing protonatable nitrogen atoms was conducted to enhance heme affinity through ionic interactions with the propionate side chains of the metalloporphyrin and to facilitate drug accumulation in the parasite food vacuole. A series of 3,6-bis-omega-diethylaminoalkoxyxanthones with side chains ranging from 2 to 8 carbon atoms were prepared and evaluated. Measurement of heme affinity for each of the derivatives revealed a strong correlation (R(2) = 0.97) between affinity and antimalarial potency. The two most active compounds in the series contained 5- and 6-carbon side chains and exhibited low nanomolar 50% inhibitory concentration (IC(50)) values against strains of chloroquine-susceptible and multidrug-resistant Plasmodium falciparum in vitro. Both of these xanthones exhibit stronger heme affinity (8.26 x 10(5) and 9.02 x 10(5) M(-1), respectively) than either chloroquine or quinine under similar conditions and appear to complex heme in a unique manner.
PMID: 11751125 [PubMed - indexed for MEDLINE]
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Phytomedicine. 2001 Mar;8(2):85-7.
Antidiabetic activity of a xanthone compound, mangiferin.
Miura T, Ichiki H, Hashimoto I, Iwamoto N, Kato M, Kubo M, Ishihara E, Komatsu Y, Okada M, Ishida T, Tanigawa K.
Suzuka University of Medical Science, Mie, Japan.
Mangiferin (MF) isolated from Anemarrhena asphodeloides Bunge rhizome, was tested for antidiabetic activity in KK-Ay mice, an animal model of type-2 diabetes. MF lowered the blood glucose level of KK-Ay mice 3 weeks after oral administration (p < 0.01). However, no effect on the blood glucose level in normal mice was seen, indicating that MF could be useful in treating type-2 diabetes. In addition, MF improved hyperinsulinemia and, on insulin tolerance test, reduced blood glucose levels of KK-Ay mice. From these findings, it seems likely that MF exerts its antidiabetic activity by decreasing insulin resistance.
PMID: 11315760 [PubMed - indexed for MEDLINE]
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J Ethnopharmacol. 2001 May;75(2-3):287-90.
Inhibitory effects of xanthones on platelet activating factor receptor binding in vitro.
Jantan I, Juriyati J, Warif NA.
Department of Pharmacy, Faculty of Allied Health Sciences, Universiti Kebangsaan Malaysia, Jalan Raja Muda Abdul Aziz, 50300, Kuala Lumpur, Malaysia. ibj@medic.ukm.my
Nine naturally occurring xanthones were investigated for their platelet activating factor (PAF) receptor binding inhibitory effects using rabbit platelets. 2-(3-methylbut-2-enyl)-1,3,5-trihydoxyxanthone, macluraxanthone, 1,3,5-trihydroxy-6,6'-dimethylpyrano(2',3':6,7)-4-(1,1-dimethylprop-2-enyl)xanthone, 6-deoxyjacareubin and 2-(3-methylbut-2-enyl)-1,3,5,6-terahydroxyxanthone showed strong inhibition with IC50 values of 4.8, 11.0, 21.0, 29.0 and 44.0 microM, respectively. The prenyl group at C-2, the dimethylprop-2-enyl group at C-4 and the hydroxyl group at C-5 are all beneficial to the binding of xanthones to the PAF receptor. The results revealed that xanthones can represent a new class of natural PAF receptor antagonists.
PMID: 11297865 [PubMed - indexed for MEDLINE]
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J Med Chem. 2001 Mar 1;44(5):672-80.
A new class of nonsteroidal aromatase inhibitors: design and synthesis of chromone and xanthone derivatives and inhibition of the P450 enzymes aromatase and 17 alpha-hydroxylase/C17,20-lyase.
Recanatini M, Bisi A, Cavalli A, Belluti F, Gobbi S, Rampa A, Valenti P, Palzer M, Palusczak A, Hartmann RW.
Department of Pharmaceutical Sciences, University of Bologna, Via Belmeloro 6, I-40126 Bologna, Italy. mreca@alma.unibo.it
Aromatase (P450arom) is a target of pharmacological interest for the treatment of breast cancer. In this paper, we report the design, synthesis, and in vitro biological evaluation of a series of new (di)benzopyranone-based inhibitors of this enzyme. The design of the new compounds was guided by a CoMFA model previously developed for a series of nonsteroidal aromatase inhibitors. Both the chromone and the xanthone nuclei were taken as molecular skeletons, and the functions supposed to be critical for binding to the aromatase active site - a heterocyclic ring (imidazole or 1,3,4-triazole) linked to the aromatic moiety by a methylene unit and an H-bond accepting function (CN, NO(2), Br) located on the aromatic ring at a suitable distance from the heterocyclic nitrogen carrying the lone pair--were attached to them. The chromone, xanthone, and flavone derivatives were prepared by conventional synthetic methods from the appropriate methyl analogues. Aromatase inhibitory activities were determined by the method of Thompson and Siiteri, using human placental microsomes and [1 beta,2 beta-(3)H]testosterone as the labeled substrate. All the compounds were also tested on 17 alpha-hydroxylase/C17,20-lyase (P450 17), an enzyme of therapeutic interest for the treatment of prostatic diseases. The goal to find new potent inhibitors of aromatase was reached with the xanthone derivatives 22d,e (IC(50) values 43 and 40 nM, respectively), which exceeded the potency of the known reference drug fadrozole and also showed high selectivity with respect to P450 17. Moreover, compounds 22g-i based on the same xanthonic nucleus showed fairly high potency as P450 17 inhibitors (IC(50) values 220, 130, and 42 nM, respectively). Thus, they might be new leads for the development of drug candidates for androgen-dependent diseases.
PMID: 11262078 [PubMed - indexed for MEDLINE]
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Am J Trop Med Hyg. 2000 Jan;62(1):77-81.
Xanthones as antimalarial agents: stage specificity.
Ignatushchenko MV, Winter RW, Riscoe M.
Department of Biochemistry and Molecular Biology, Oregon Health Sciences University, Portland 97201, USA.
The erythrocytic development of Plasmodium falciparum is divided into the ring, trophozoite, and schizont stages based on morphologic assessment. Using highly synchronous ring and trophozoite cultures of P. falciparum, we observed considerable differences in their sensitivity to hydroxyxanthones: trophozoites were much more sensitive to the drugs than ring-stage parasites. Trophozoites treated with a prototypic xanthone, the 2,3,4,5,6-pentahydroxy derivative (X5), were arrested in their development and became degenerate in appearance within 24 hr of drug exposure. These morphologic changes appeared to reflect the cytotoxic nature of the action of the drug against the parasite, since daughter ring-stage forms were not observed following addition of the drug. That X5 was more active against parasites in the later stages of intraerythrocytic development is consistent with the proposed mode of action, inhibition of heme polymerization. Knowledge of the structure-activity relationships for xanthones as antimalarial agents has also been expanded. Xanthones with a hydroxyl group in the peri-position exhibited decreased antimalarial activity, possibly due to intramolecular hydrogen bonding with the carbonyl and consequent reduced affinity for heme. Paired hydroxyls attached to the lower half of the xanthone greatly enhanced drug potency.
PMID: 10761728 [PubMed - indexed for MEDLINE
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Acta Pol Pharm. 1999 Jul-Aug;56(4):319-24.
Antiplatelets activity of some xanthone derivatives.
Rajtar G, Zolkowska D, Kleinrok Z, Marona H.
Department of Pharmacology and Toxicology, Medical University School, Lublin, Poland.
The effects of twelve aminoalkanolic derivatives of xanthone on platelet aggregation have been evaluated. Five from them inhibited thrombin-induced platelet aggregation. The most active compound was R-(+)-2-N-(7-chloro-2-xanthonemethyl)-2-N-methylamino-1-butanol [IV] which, at a concentration of 40 micrograms/ml, nearly completely inhibited the aggregation concentration (TAC) of thrombin.
PMID: 10635366 [PubMed - indexed for MEDLINE]
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Acta Pol Pharm. 1999 Jul-Aug;56(4):311-8.
Pharmacological properties of some xanthone derivatives.
Rajtar G, Zolkowska D, Kleinrok Z, Marona H.
Department of Pharmacology and Toxicology, Medical University School, Lublin, Poland.
A series of aminoalkanolic derivatives of xanthone were examined in some experimental models of epilepsia, i.e., pilocarpine, aminophylline and pentetrazole-induced seizures. A final objective of this research was to examine the action of these compounds on the central nervous system, namely on spontaneous locomotor activity, amphetamine-induced hyperactivity and narcotic sleep induced by hexobarbital, as well as their influence on the gamma-aminobutyric acid (GABA) level and glutamic acid decarboxylase (GAD) activity in mice brain. The most interesting were the pharmacological results of (R)-2-N-methylamino-1-butanol derivative of 7-chloro-2-methylxanthone [Id], which displayed protective activity against the seizures induced by maximum electroshock and pentetrazole induced seizures; moreover, this compound had a relatively low toxicity and did not exhibit a neurotoxic effect. The influence on the locomotor activity as well as on the amphetamine-induced locomotor hyperactivity in mice was also seen for Id. Compound Id did not decrease the GABA level in mice brain.
PMID: 10635365 [PubMed - indexed for MEDLINE]
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Acta Pol Pharm. 1999 Jan-Feb;56(1):87-90.
Chiral 2-amino-1-butanol xanthone derivatives as potential antiarrhythmic and hypotensive agents.
Librowski T, Czarnecki R, Jastrzebska M.
Department of Pharmacodynamics, Collegium Medicum Jagiellonian University, Krakow, Poland.
PMID: 10635353 [PubMed - indexed for MEDLINE]
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J Ethnopharmacol. 1999 Sep;66(3):339-42.
Antimicrobial activity of xanthones from Calophyllum species, against methicillin-resistant Staphylococcus aureus (MRSA).
Dharmaratne HR, Wijesinghe WM, Thevanasem V.
Natural Products Programme, Institute of Fundamental Studies, Kandy, Sri Lanka.
During the past 5 years, a considerable number of known and new xanthones from the Calophyllum species of Sri Lanka have been isolated and characterized. We have investigated the antimicrobial activity of Calophyllum xanthones, with a special reference to methicillin-resistant Staphylococcus aureus (MRSA). These activity studies were carried out using the agar plate method. Calozeloxanthone, a xanthone which has been isolated from C. moonii and C. lankensis, showed the highest activity against methicillin-resistant S. aureus (MRSA) strains at a concentration of 8.3 microg/ml. Hence, calozeyloxanthone appears to hold promise as an antimicrobial agent in the treatment of infections with S. aureus, including methicillin-sensitive S. aureus (MRSA), and should be investigated further.
PMID: 10473182 [PubMed - indexed for MEDLINE]
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Farmaco. 1999 Jun 30;54(6):411-5.
Flavone and xanthone derivatives related to fluoroquinolones.
Mari S, Rossi M, Valenti P, Da Re P.
Institute of Pharmaceutical Chemistry, University of Milan, Italy.
A number of flavone and xanthone derivatives bearing some characteristic features of fluoroquinolones such as the fluorine atom and an ortho piperazine ring are described. The new compounds have been tested for possible cytotoxic and antimicrobial activities. Cytotoxicity of both groups of compounds is rather poor, while the antibacterial activity is restricted to xanthones.
PMID: 10443020 [PubMed - indexed for MEDLINE]
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Cancer Lett. 1998 Oct 23;132(1-2):113-7.
Xanthones as inhibitors of Epstein-Barr virus activation.
Ito C, Itoigawa M, Furukawa H, Rao KS, Enjo F, Bu P, Takayasu J, Tokuda H, Nishino H.
Faculty of Pharmacy, Meijo University, Nagoya, Japan.
To search for possible antitumor promoters, we carried out a primary screening of 20 xanthones isolated from plants of the Guttiferae family, using their possible inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells. Some of these xanthones, namely 1,3,7-trihydroxy-2-(3-methyl-2-butenyl)xanthone (8), dulxanthone-B (10) and latisxanthone-C (15), were observed to significantly inhibit the EBV-EA activation. The investigation indicated that 8, 10 and 15 might be valuable antitumor promoters.
PMID: 10397461 [PubMed - indexed for MEDLINE]
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Pharmazie. 1998 Oct;53(10):672-6.
Synthesis and anticonvulsant effects of some aminoalkanolic derivatives of xanthone.
Marona H.
Department of Chemical Technology of Drugs, Collegium Medicum, Jagiellonian University, Krakow, Poland.
Synthesis and physicochemical properties of alkanolamine derivatives of xanthone are described. Alkanolamines were synthesized by of the reaction of an appropriate aminoalcohol with corresponding 2-bromomethylxanthones. The obtained compounds 1-13 were evaluated for anticonvulsant activity in the maximal electroshock seizure (MES) and subcutaneous pentylenetetrazole seizure threshold (scMet) assays and for neurotoxicity (TOX). Several alkanolamines were found to be active in both the anticonvulsant tests. Most interesting were the 2-amino-1-propanol-, 1-amino-2-propanol- or 1-amino-2-butanol derivatives of 6-methoxy- or 6-chloroxanthone, which displayed anti MES activity with a protective index (TD50/ED50) in the range 2.21-5.84 corresponding with that for phenytoin, carbamazepine and valproate.
PMID: 9812332 [PubMed - indexed for MEDLINE]
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Arch Pharm (Weinheim). 1998 Jun;331(6):225-7.
Allylamine type xanthone antimycotics.
Salmoiraghi I, Rossi M, Valenti P, Da Re P.
Institute of Pharmaceutical Chemistry, University of Milan, Italy.
A number of xanthone derivatives bearing the basic chain of naftifine and butenafine antimycotics in 1, 2, 3, and 4 nuclear positions are described. The in vitro antifungal activity against representative strains of molds and yeasts is reported. Only butenafine xanthone analogues show significant activity against Cryptococcus neoformans, in particular the regioisomer 4d (1.5 micrograms/ml).
PMID: 9713256 [PubMed - indexed for MEDLINE]
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Pharmazie. 1998 Jun;53(6):405-9.
Evaluation of some 2-substituted derivatives of xanthone for anticonvulsant properties.
Marona H.
Department of Chemical Technology of Drugs, Collegium Medicum of the Jagiellonian University, Krakow, Poland.
A series of alkanolamides and alkanoamines derivatives of xanthone were prepared and evaluated for antiepileptic activity in the maximal electroshock seizure (MES) and subcutaneous pentylenetetrazol seizure threshold (ScMet) assays and for neurotoxicity (TOX). Several analogues from the appropriate alkanolamines were found to be active in both the anticonvulsant tests. Most interesting were the anticonvulsant results of the appropriate 2-amino- or 2-N-methylamino-1-butanol derivatives of 7-chloroxanthone 8-11, which displayed anti-MES activity with a protective index (TD50/ED50) in the range 2.84-3.62 for 8-11 corresponding with that for phenytoin, carbamazepine and valproate.
PMID: 9675771 [PubMed - indexed for MEDLINE]
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Pharmazie. 1998 Apr;53(4):219-23. Properties of Xanthones
Aminoalkanolic derivatives of xanthone with potential antiepileptic activity.
Marona H, Gorka Z, Szneler E.
Department of Chemical Technology of Drugs, Jagiellonian University, Krakow, Poland.
Synthesis, physicochemical and anticonvulsant properties of some aminoisopropanoloxy derivatives of 2-xanthone are described. The compounds were prepared by the amination of 2-[(2,3-epoxy)-propoxyl]-xanthone or 2-(3-chloro-2-hydroxy-propoxy)-xanthone. The obtained compounds were evaluated for anticonvulsant activity in the maximal electroshock (MES)- and subcutaneous pentylenetetrazole (scMet)-induced seizures and for neurotoxicity in the rotorod test in mice and rats. The most promising compounds seem to be the 3-(tert.-butyl-amino) (3), 3-[N-methyl-(tert.-butyl)-amino] (12) and 3-[4-(benzyl)-1-piperazinyl (5) substituted 2-hydroxy-1-(2-xanthonoxy)-propane from which 3 and 5 were active in both the anticonvulsant tests. The protective index (TD50/ED50) in MES in mice for 3 and valproate, as for 12 and phenytoin or carbamazepine, is similar.
PMID: 9583083 [PubMed - indexed for MEDLINE]
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Planta Med. 1998 Feb;64(1):70-2.
Antimalarial xanthones from Garcinia cowa.
Likhitwitayawuid K, Phadungcharoen T, Krungkrai J.
Five xanthones from the bark of Garcinia cowa, namely 7-O-methylgarcinone E (1), cowanin (2), cowanol (3), cowaxanthone (4), and beta-mangostin (5), were found to possess in vitro antimalarial activity against Plasmodium falciparum with IC50 values ranging from 1.50 to 3.00 micrograms/ml. Complete 1H- and 13C-NMR assignments of these compounds are also reported.
Publication Types:
• Letter
PMID: 9491769 [PubMed - indexed for MEDLINE]
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Eur J Pharmacol. 1997 Oct 1;336(1):23-8.
Mechanism of vasorelaxation of thoracic aorta caused by xanthone.
Cheng YW, Kang JJ.
Institute of Toxicology, College of Medicine, National Taiwan University, Taipei.
The effect of xanthone on smooth muscle was studied in thoracic aorta isolated from rats. Xanthone relaxed the norepinephrine-induced contraction of rat thoracic aorta. This relaxing effect of xanthone persisted in endothelium-denuded aorta suggesting that the relaxation induced by xanthone is endothelium-independent. The norepinephrine and high-K+-induced vasoconstriction was inhibited dose dependently in aorta pretreated with xanthone with IC50 values of 60.26 +/- 8.43 and 82.9 +/- 13.21 microM, respectively. The inositol 1,4,5-trisphosphate formation induced by norepinephrine (3 microM) in rat aorta was not affected by xanthone (10-100 microM), suggesting that the vasorelaxant effect of xanthone was not exerted on the receptor. Xanthone concentration dependently inhibited the 45Ca2+ influx induced by either norepinephrine or high-K+, suggesting that xanthone might act as a blocker of both receptor-operated and voltage-dependent Ca2+ channels. Furthermore, xanthone caused an increase in the level of intracellular cyclic adenosine 3',5'-monophosphate (cAMP), but not cyclic guanosine 3',5'-monophosphate (cGMP) content. These data suggested that the mechanism of xanthone-induced vasorelaxation might involve the increase of intracellular cyclic adenosine 3',5'-monophosphate (cAMP) content and block of Ca2+ channels.
PMID: 9384250 [PubMed - indexed for MEDLINE]
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FEBS Lett. 1997 Jun 2;409(1):67-73. Properties of Xanthones
Xanthones as antimalarial agents; studies of a possible mode of action.
Ignatushchenko MV, Winter RW, Bachinger HP, Hinrichs DJ, Riscoe MK.
Department of Biochemistry and Molecular Biology, Oregon Health Sciences University, Portland 97201, USA.
We recently demonstrated that 2,3,4,5,6-pentahydroxyxanthone (X5) inhibits the in vitro growth of both chloroquine-sensitive and multidrug-resistant strains of P. falciparum. To study the molecular basis of its antimalarial action, we tested X5 and selected hydroxyxanthone analogs as inhibitors of in vitro heme polymerization in a low ionic strength phosphate solution at mildly acidic pH. We found that addition of 1 Eq. of X5 resulted in complete inhibition of polymerization in this system whereas addition of up to 40 Eqs. of standard antimalarial compounds (chloroquine, primaquine, quinacrine, artemisinin and methylene blue) had no such effect although these compounds did co-precipitate with heme. The antimalarial potency of the hydroxyxanthones correlated well with their ability to inhibit in vitro heme polymerization in our assay, suggesting that these compounds exert their antimalarial action by preventing hemozoin formation. Based on the observed structure-activity relationships, we propose a model displaying possible interactions between hydroxyxanthones and heme.
PMID: 9199506 [PubMed - indexed for MEDLINE]
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Anticancer Res. 1997 Mar-Apr;17(2A):1107-14.
Antitumor effect of 2,6-di(2,3-epoxypropoxy)xanthone on tumor cell lines.
Liu HS, Lin CN, Won SJ.
Department of Microbiology and Immunology, National Cheng Kung University, Tainan, Taiwan, R.O.C. a713@mail.ncku.edu.tw
2,6-di(2,3-epoxypropoxy)xanthone (EPX), a newly synthesized xanthone derivative, is a potent antitumor agent, which is more cytotoxic than the antitumor drug mytomycin C. EPX also demonstrated stronger growth inhibition to T24 (bladder carcinoma with Ha-ras gene mutation) and 212 cells (a NIH/3T3 derivative, transformed by Ha-ras oncogene) than to PLC/PRF/S (hepatoma with normal Ha-ras gene) and NIH/3T3 cells. The preferential repression of EPX on the cell proliferation of 212 and T24 cells was further demonstrated by decreasing Ha-ras oncogene expression levels while EPX dosage increased. The drug concentrations for 50% inhibition (IC50) of cell growth, DNA synthesis Ha-ras oncogene expression and colony formation of T24 and 212 cells are in the same range and lower than the values for RNA and protein synthesis. Moreover, EPX irreversibly reversed 212 cell morphology from a transformed phenotype to a normal one. These data indicate that EPX probably suppresses tumor cell proliferation by inhibiting DNA synthesis and reverses the transformed properties by suppressing Ha-ras gene expression. The mechanisms of biochemical action and cytotoxicity of EPX remain to be determined. However, our data suggest that the EPX-mediated inhibition of cell proliferative capacity of 212 and T24 cells was preceded by a selective down-regulation of Ha-ras oncogene RNA levels. EPX may have the potential to be used broadly against diverse tumors or specifically against Ha-ras oncogene initiated malignancy.
PMID: 9137457 [PubMed - indexed for MEDLINE]
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J Pharm Pharmacol. 1996 Sep;48(9):887-90.
Synthesis and antithrombotic effect of xanthone derivatives.
Lin CN, Hsieh HK, Liou SJ, Ko HH, Lin HC, Chung MI, Ko FN, Liu HW, Teng CM.
School of Pharmacy, Department of Internal Medicine, Kaohsiung Medical College, Taiwan, R.O.C.
A series of xanthone derivatives was synthesized and tested in-vitro for their ability to inhibit aggregation of rabbit washed platelets and human platelet-rich plasma (PRP) induced by various inducers. 2-Prenyloxyxanthone showed the most potent inhibition of rabbit washed platelet aggregation induced by arachidonic acid (1C50 = 10.2 microM). Of the compounds tested in human PRP, 2-[3 (propylamino)-2-hydroxypropoxy]xanthone (4) hydrochloride salt exhibited the most potent inhibition of platelet aggregation induced by adrenaline (IC50 = 4.4 microM), whereas in evaluation of mouse antithrombotic activity, compound 4 exhibited the most potent protection of mice from thrombotic challenge. Compound 4, 2-[3-(isopropylamino)-2-hydroxypropoxylxanthone hydrochloride salt and 2,5 dihydroxyxanthone suppressed the secondary aggregation induced by adrenaline in human PRP. We conclude that the antiplatelet effects of these compounds are mainly due to an inhibitory effect on thromboxane formation.
PMID: 8910846 [PubMed - indexed for MEDLINE]
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J Pharm Pharmacol. 1996 Aug;48(8):861-5.
Antibacterial activity of xanthones from guttiferaeous plants against methicillin-resistant Staphylococcus aureus.
Iinuma M, Tosa H, Tanaka T, Asai F, Kobayashi Y, Shimano R, Miyauchi K.
Department of Pharmacognosy, Gifu Pharmaceutical University, Japan.
Extracts of Garcinia mangostana (Guttiferae) showing inhibitory effects against the growth of S. aureus NIHJ 209p were fractionated according to guidance obtained from bioassay and some of the components with activity against methicillin-resistant Staphylococcus aureus (MRSA) were characterized. One active isolate, alpha-mangostin, a xanthone derivative, had a minimum inhibitory concentration (MIC) of 1.57-12.5 micrograms mL-1. Other related xanthones were also examined to determine their anti-MRSA activity. Rubraxanthone, which was isolated from Garcinia dioica and has a structure similar to that of alpha-mangostin, had the highest activity against staphylococcal strains (MIC = 0.31-1.25 micrograms mL-1), an activity which was greater than that of the antibiotic vancomycin (3.13-6.25 micrograms mL-1). The inhibitory effect against strains of MRSA of two of the compounds when used in conjunction with other antibiotics was also studied. The anti-MRSA activity of alpha-mangostin was clearly increased by the presence of vancomycin; this behaviour was not observed for rubraxanthone. The strong in-vitro antibacterial activity of xanthone derivatives against both methicillin-resistant and methicillin-sensitive Staphylococcus aureus suggests the compounds might find wide pharmaceutical use.
PMID: 8887739 [PubMed - indexed for MEDLINE]
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J Pharm Pharmacol. 1996 May;48(5):539-44.
Xanthone derivatives as potential anti-cancer drugs.
Lin CN, Liou SJ, Lee TH, Chuang YC, Won SJ.
School of Pharmacy, Kaohsiung Medical College, Taiwan, Republic of China.
Xanthone derivatives have been shown to be potent inhibitors of tumour growth. Oxygenated xanthones and [3-(dialkylamino)-2-hydroxypropoxy]xanthones have been prepared and tested for in-vitro inhibition of human PLC/PRF/5, KB and 212 cells. Structure-activity analysis indicated epoxidation of the hydroxyxanthone increased cytotoxicity against tumour cells but ring-opening of the epoxide group with dialkylamine did not enhance the anti-tumour activity. Further evaluation of three of the most active compounds 2, 6-, 3, 6-, and 3, 5-di(2,3-epoxypropoxy)xanthone (compounds 10a, 11a, and 12a, respectively) in DNA, RNA and protein synthesis of tumour cells showed potent inhibitory activity. The 3,5-di(2,3-epoxypropoxy)xanthone also showed potent inhibitory activity against 212 cells, a Ha-ras oncogene-transformed NIH 3T3 cell line. The results indicated that compounds 10a and 12a are potent anti-tumour agents which not only suppressed cellular DNA, RNA and protein synthesis but also specifically inhibited the Ha-ras oncogene in 212 cells.
PMID: 8799883 [PubMed - indexed for MEDLINE]
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J Pharm Pharmacol. 1996 May;48(5):532-8.
Synthesis and anti-inflammatory effects of xanthone derivatives.
Lin CN, Chung MI, Liou SJ, Lee TH, Wang JP.
School of Pharmacy, Kaohsiung Medical College, Taiwan, R.O.C.
Eighteen synthetic xanthone derivatives were tested for their inhibitory effects on the activation of mast cells and neutrophils. 1,3- and 3,5-Dihydroxyxanthone showed strong inhibitory effects on the release of beta-glucuronidase and histamine from rat peritoneal mast cells stimulated with compound 48/80. 1,6-Dihydroxyxanthone and 1,3,8-trihydroxyxanthone showed strong inhibitory effects on the release of beta-glucuronidase, and beta-glucuronidase and lysozyme, respectively, from rat neutrophils stimulated with formyl-Met-Leu-Phe (fMLP). 1,3- and 1,6-Dihydroxyxanthone, 1,3,7-trihydroxyxanthone, and 1,3,5,6-, 2,3,6,7-, and 3,4,5,6-tetrahydroxyxanthone showed potent inhibitory effects on superoxide formation of rat neutrophils stimulated with fMLP. 1,6- and 3,5-Dihydroxyxanthone showed remarkable inhibitory effects on hind-paw oedema induced by polymyxin B in normal as well as in adrenalectomized mice. These data indicated that the anti-inflammatory effect of these compounds is mediated through the suppression of chemical mediators released from mast cell and neutrophil degranulation.
PMID: 8799882 [PubMed - indexed for MEDLINE]
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J Nat Prod. 1995 Jul;58(7):1024-31.
Mechanistic evaluation of new plant-derived compounds that inhibit HIV-1 reverse transcriptase.
Pengsuparp T, Cai L, Constant H, Fong HH, Lin LZ, Kinghorn AD, Pezzuto JM, Cordell GA, Ingolfsdottir K, Wagner H, et al.
Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago 60612, USA.
Swertifrancheside [1], a new flavonone-xanthone glucoside isolated from Swertia franchetiana, 1 beta-hydroxyaleuritolic acid 3-p-hydroxybenzoate [2], a triterpene isolated from the roots of Maprounea africana, and protolichesterinic acid [3], an aliphatic alpha-methylene-gamma-lactone isolated from the lichen Cetraria islandica, were found to be potent inhibitors of the DNA polymerase activity of human immunodeficiency virus-1 reverse transcriptase (HIV-1 RT), with 50% inhibitory doses (IC50 values) of 43, 3.7, and 24 microM, respectively. They were not cytotoxic with cultured mammalian cells. The kinetic mechanisms by which compounds 1-3 inhibited HIV-1 RT were studied as was their potential to inhibit other nucleic acid polymerases. Swertifrancheside [1] bound to DNA and was shown to be a competitive inhibitor with respect to template-primer, but a mixed-type competitive inhibitor with respect to TTP. On the other hand, 1 beta-hydroxyaleuritolic acid 3-p-hydroxybenzoate [2] and protolichesterinic acid [3] were mixed-type competitive inhibitors with respect to template-primer and noncompetitive inhibitors with respect to TTP. Therefore, the mechanism of action of 1 beta-hydroxyaleuritolic acid 3-p-hydroxybenzoate [2] and protolichesterinic acid [3] as HIV-1 RT inhibitors involves nonspecific binding to the enzyme at nonsubstrate binding sites, whereas swertifrancheside [1] inhibits enzyme activity by binding to the template-primer.
PMID: 7561895 [PubMed - indexed for MEDLINE]
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Chem Pharm Bull (Tokyo). 1995 Feb;43(2):347-9.
Novel xanthones with superoxide scavenging activity from Garcinia subelliptica.
Minami H, Takahashi E, Fukuyama Y, Kodama M, Yoshizawa T, Nakagawa K.
Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Japan.
Two new xanthones, garciniaxanthone D (1) containing a dihydrobenzofuran ring and 1,4,5-trihydroxyxanthone (2), have been isolated from Garcinia subelliptica as superoxide anion scavengers. Their structures have been determined mainly by spectroscopic methods and some chemical reactions.
PMID: 7728938 [PubMed - indexed for MEDLINE]
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Planta Med. 1994 Aug;60(4):365-8. Properties of Xanthones
Xanthones of Garcinia cowa.
na Pattalung P, Thongtheeraparp W, Wiriyachitra P, Taylor WC.
Research Centre for Natural Products, Faculty of Pharmacy, Chiang Mai University, Thailand.
Five xanthones have been isolated from Garcinia cowa Roxb. (Guttiferae): cowanin (1), cowanol (2), cowaxanthone (3), 1,3,6-trihydroxy-7-methoxy- 2-5-bis(3-methyl-2-butenyl)xanthone (4), and norcowanin (5). The structures were assigned by spectroscopic studies. Xanthones 2 and 3 showed moderate antimicrobial activity against Staphylococcus aureus.
PMID: 7938273 [PubMed - indexed for MEDLINE]
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Cancer Res. 1994 Jun 15;54(12):3191-5.
Mechanism of action of the antileukemic xanthone psorospermin: DNA strand breaks, abasic sites, and protein-DNA cross-links.
Permana PA, Ho DK, Cassady JM, Snapka RM.
Department of Radiology, Ohio State University, Columbus 43210.
Psorospermin, a cytotoxic dihydrofuranoxanthone isolated from Psorospermum febrifugum, produced aberrant simian virus 40 DNA replication intermediates when added to lytically infected CV-1 monkey kidney cells. The aberrant viral intermediates showed dose-dependent DNA strand breaks and protein-DNA cross-links, as well as decreased electrophoretic mobility. Simian virus 40 DNA from psorospermin-treated cells was shown to contain numerous abasic (apyrimidinic/apurinic) sites. The density of abasic sites was a function of the psorospermin dose. We conclude that psorospermin causes extensive loss of DNA bases in vivo. Primary amine groups of cellular proteins are known to react with abasic sites to form covalent protein-DNA cross-links and DNA strand breaks. Cytochrome c cross-linked spontaneously to viral DNA prepared from psorospermin-treated cells but not to DNA from untreated cells. This suggests that the protein-DNA cross-links and many of the DNA strand breaks observed in vivo result from reactions between abasic sites and chromosomal proteins. It is likely that the protein-DNA cross-links and DNA strand breaks contribute to the cytotoxicity and antineoplastic activity of psorospermin.
PMID: 8205539 [PubMed - indexed for MEDLINE]
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Arzneimittelforschung. 1990 Feb;40(2 Pt 1):122-5.
Xanthone 1,4-dihydropyridine derivatives with a potent selective bradycardic effect.
Valenti P, Chiarini A, Gasperi F, Budriesi R.
Department of Pharmaceutical Sciences, University of Bologna, Italy.
A series of xanthone 1,4-dihydropyridine derivatives were prepared. The compounds were evaluated for inotropic, chronotropic and calcium antagonistic properties. The tested compounds are weak calcium antagonists but exert potent selective bradycardic effects.
PMID: 2334451 [PubMed - indexed for MEDLINE]
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Biochem Pharmacol. 1989 Nov 1;38(21):3791-5.
Novel inhibitory actions on platelet thromboxane and inositolphosphate formation by xanthones and their glycosides.
Teng CM, Lin CN, Ko FN, Cheng KL, Huang TF.
Pharmacological Institute, College of Medicine, National Taiwan University, Taipei, Republic of China.
Xanthones and their glycosides were tested for their antiplatelet activities in washed rabbit platelets. Tripteroside acetate and norathyriol acetate were the most potent inhibitors. Tripteroside acetate inhibited platelet aggregation and ATP release induced by ADP, arachidonic acid, platelet-activating factor (PAF), collagen, ionophore A23187 and thrombin. The IC50 values of tripteroside acetate toward arachidonic acid- (100 microM) and collagen- (10 micrograms/ml) induced platelet aggregation were 10 and 30 micrograms/ml respectively. It inhibited thromboxane B2 formation of washed platelets caused by arachidonic acid, collagen, thrombin and ionophore A23187 and also that caused by the incubation of lysed platelet homogenate with arachidonic acid. Tripteroside acetate decreased the formation of inositolphosphate caused by thrombin, collagen and PAF, whereas it had no direct effect on fibrinogen-platelet interaction. It is concluded that xanthone derivatives inhibited platelet aggregation and release reaction by diminishing thromboxane formation and phosphoinositide breakdown.
PMID: 2512926 [PubMed - indexed for MEDLINE]
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Farmaco. 1989 Jun;44(6):547-54.
Synthesis of 2-hydroxyacetyl-7-acetyl-xanthone, a new xanthone derivative endowed with antianaphylactic, analgesic, and antinflammatory activities.
Bianco A, Passacantilli P, Righi G, Brufani M, Cellai L, Marchi E, Milani MR.
Dipartimento di Chimica, Universita La Sapienza, Roma.
2-Hydroxyacetyl-7-acetylxanthone (V), a new xanthone derivative, was synthesized in four steps starting from xanthene, by two synthetic approaches. The new compound displayed antianaphylactic activity in the PCA test and in the anaphylaxis shock test in rats. It also displayed analgesic activity in the writhing test in mice, and antiinflammatory activity in the carrageenin edema test in rats. The activity of the new compound has been tentatively interpreted on the basis of its chemical and structural analogy with known drugs.
PMID: 2803446 [PubMed - indexed for MEDLINE]
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J Antibiot (Tokyo). 1987 Mar;40(3):301-8.
Structure of cervinomycin, a novel xantone antibiotic active against anaerobe and mycoplasma.
Nakagawa A, Omura S, Kushida K, Shimizu H, Lukacs G.
The structures of cervinomycins A1 (1) and A2 (2), a potent anti-anaerobic and anti-mycoplasmal antibiotic were investigated by means of recent NMR techniques of O-methyl ether (3) and C,O-dimethyl ether (4) obtained by methylation of 2 with CH3I in the presence of Ag2O. The antibiotic 2 posesses a polycyclic structure involving a xanthone skeleton. The structure of 1 was confirmed to be a hydroquinone of 2 from the evidences that oxidation of 1 with Ag2O and acetylation of 1 with (CH3CO)2O in pyridine afforded quantitatively 2 and triacetylcervinomycin A1 (7), respectively.
PMID: 3570983 [PubMed - indexed for MEDLINE]
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Arch Int Pharmacodyn Ther. 1982 Sep;259(1):166-76.
Xanthone-2-carboxylic acid effect on lens growth, hydration and proteins during diabetic cataract development.
Beyer-Mears A, Cruz E, Nicolas-Alexandre J, Varagiannis E.
The concomitant protective effects of the aldose reductase inhibitor, 7-dimethylsulfamoyl-xanthone-2-carboxylic acid, were established by three lens parameters (soluble crystallin proteins, growth and cell hydration) because their quantitation provided a comprehensive index of lens physiology during sugar cataractogenesis in the rat neonate. Their fused eyelids provided the orbital pouch for topical administration of inhibitor to the treated lens; the contralateral pouch served as an untreated control. Protein preservation was determined by gel filtration chromatography. In galactose-maintained neonates, untreated lenses exhibited only 50% of the normal Fraction II protein whereas xanthone-treatment maintained 73% of this component. Quantitative analysis of scanning electron micrographs indicated that xanthone-treatment partially protected lenses against both intra and extracellular fluid accumulation as determined by measurements of individual fiber cell thickness, density (the number of cells/10 micron cortex), and interdigitation. In addition, xanthone-treatment improved lens growth as evidenced by radius and dry weight measurements. Our results suggest that topically applied xanthone partially inhibited sugar cataractogenesis.
PMID: 6817723 [PubMed - indexed for MEDLINE]
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Arch Immunol Ther Exp (Warsz). 1982;30(5-6):333-9.
Antiallergic action of disodium cromoglycate and xanthone RS 7540.
Gonzalez Alvarez R, Kazimierczak W.
Disodium cromoglycate (DSCG) and RS 7540 both inhibited the rat PCA reaction mediated by mouse IgE; RS 7540 was more potent. RS 7540 showed self- and cross-tachyphylaxis with DSCG and failed to protect rat mast cells against desensitization induced by antigen. In the guinea pig ileum test, DSCG reduced stimulation by various spasmogens, whereas RS 7540 even at high doses was inactive. These differences suggest that RS 7540 has major deficiencies as a potential alternative to DSCG in the treatment of bronchial asthma.
PMID: 6135406 [PubMed - indexed for MEDLINE]
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Planta Med. 1981 May;42(1):17-21.
Inhibition of type A and type B monoamine oxidases by naturally occurring xanthones.
Suzuki O, Katsumata Y, Oya M, Chari VM, Vermes B, Wagner H, Hostettmann K.
PMID: 7255567 [PubMed - indexed for MEDLINE]
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Indian J Exp Biol. 1980 Aug;18(8):843-6.
Effect of mangostin, a xanthone from Garcinia mangostana Linn. in immunopathological & inflammatory reactions.
Gopalakrishnan C, Shankaranarayanan D, Kameswaran L, Nazimudeen SK.
PMID: 7461736 [PubMed - indexed for MEDLINE]
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Scand J Respir Dis. 1978 Apr;59(2):75-81.
The effect of inhaled RS 7540, a xanthone, on exercise-induced asthma.
Stenius B, Salorinne Y, Parrott D.
The effect of 71 oxo-7-thiomethoxyxanthone-2-carboxylic acid sodium salt (RS 7540) in inhibiting exercise-induced asthma was compared with that of placebo in a double-blind crossover study. Single doses of 40 mg were given by inhalation to 12 patients. Ten of these subsequently received a dose of 20 mg. RS 7540 at both dose levels had a statistically significant effect in giving total or partial protection from exercise-induced bronchospasm; however, no dose relationship was apparent.
Publication Types:
• Clinical Trial
• Controlled Clinical Trial
PMID: 356252 [PubMed - indexed for MEDLINE]
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Arzneimittelforschung. 1968 Jun;18(6):718-20.
Xanthone derivatives with centrally stimulating and analeptic activities.
Da Re P, Mancini V, Toth E, Cima L.
PMID: 4387810 [PubMed - indexed for MEDLINE]
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Mol Pharmacol. 2004 Jun 24 [Epub ahead of print]
gamma-Mangostin Inhibits IkappaB Kinase Activity and Decreases Lipopolysaccharide-Induced Cyclooxygenase-2 Gene Expression in C6 Rat Glioma Cells.
Nakatani K, Yamakuni T, Kondo N, Arakawa T, Oosawa K, Shimura S, Inoue H, Ohizumi Y.
Graduate school of Pharmaceutical Science, Tohoku University.
We here investigated the effect of gamma-mangostin purified from the fruit hull of the medicinal plant, Garcinia mangostana, on spontaneous prostaglandin E2 (PGE2) release and inducible cyclooxygenase (COX-2) gene expression in C6 rat glioma cells. An 18-h treatment with gamma-mangostin potently inhibited spontaneous PGE2 release in a concentration-dependent manner with the IC50 value of about 2 microM, without affecting the cell viability even at 30 microM. By immunoblotting and RT-PCR, it was shown that gamma-mangostin concentration-dependently inhibited lipopolysaccharide (LPS)-induced expression of COX-2 protein and its mRNA, but not those of constitutive COX-1 cyclooxygenase. Since LPS is known to stimulate IkappaB kinase (IKK)-mediated phosphorylation of inhibitor kappaB (IkappaB) followed by its degradation which in turn induces NF-kappaB nuclear translocation leading to transcriptional activation of COX-2 gene, the effect of gamma-mangostin on the IKK/IkappaB cascade controlling the NF-kappaB activation was examined. An in vitro IKK assay using IKK protein immunoprecipitated from C6 cell extract showed that this compound inhibited IKK activity in a concentration-dependent manner with the IC50 value of about 10 microM. Consistently gamma-mangostin was also observed to decrease the LPS-induced IkappaB degradation and phosphorylation in a concentration-dependent manner, as assayed by immunoblotting. Furthermore, luciferase reporter assays showed that gamma-mangostin reduced the LPS-inducible activation of NF-kappaB- and human COX-2 gene promoter region-dependent transcription. gamma-Mangostin also inhibited rat carrageenan-induced paw edema. These results suggest that gamma-mangostin directly inhibits IKK activity, and thereby prevents COX-2 gene transcription, an NF-kappaB target gene, probably to decrease the inflammatory agent-stimulated PGE2 production in vivo, and is a new useful lead compound for anti-inflammatory drug development.
PMID: 15218091 [PubMed - as supplied by publisher]
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Br J Pharmacol. 1998 Mar;123(5):855-62. Properties of Xanthones
Effect of gamma-mangostin through the inhibition of 5-hydroxy-tryptamine2A receptors in 5-fluoro-alpha-methyltryptamine-induced head-twitch responses of mice.
Chairungsrilerd N, Furukawa K, Tadano T, Kisara K, Ohizumi Y.
Department of Molecular Biology, Faculty of Pharmaceutical Sciences, Tohoku University, Sendai, Japan.
1. Intracerebronventricular (i.c.v.) injection of gamma-mangostin (10-40 nmol/mouse), a major compound of the fruit hull of Garcinia mangostana Lin., like ketanserin (10, 20 nmol/mouse, i.c.v.) inhibited 5-fluoro-alpha-methyltryptamine (5-FMT) (45 mg kg(-1), i.p.)-induced head-twitch response in mice in the presence or absence of citalopram (a 5-hydroxytryptamine (5-HT)-uptake inhibitor). 2. Neither the 5-FMT- nor the 8-hydroxy-2-(di-n-propylamino)tetralin (5-HT1A-agonist)-induced 5-HT syndrome (head weaving and hindlimb abduction) was affected by gamma-mangostin or ketanserin. 3. The locomotor activity stimulated by 5-FMT through the activation of alpha1-adrenoceptors did not alter in the presence of gamma-mangostin. 4. 5-HT-induced inositol phosphates accumulation in mouse brain slices was abolished by ketanserin. Gamma-mangostin caused a concentration-dependent inhibition of the inositol phosphates accumulation. 5. Gamma-mangostin caused a concentration-dependent inhibition of the binding of [3H]-spiperone, a specific 5-HT2A receptor antagonist, to mouse brain membranes. 6. Kinetic analysis of the [3H]-spiperone binding revealed that gamma-mangostin increased the Kd value without affecting the Bmax value, indicating the mode of the competitive nature of the inhibition by gamma-mangostin. 7. These results suggest that gamma-mangostin inhibits 5-FMT-induced head-twitch response in mice by blocking 5-HT2A receptors not by blocking the release of 5-HT from the central neurone. Gamma-mangostin is a promising 5-HT2A receptor antagonist in the central nervous system.
PMID: 9535013 [PubMed - indexed for MEDLINE]
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Nippon Yakurigaku Zasshi. 1997 Oct;110 Suppl 1:153P-158P.
[Novel types of receptor antagonists from the medicinal plant Garcinia mangostana]
[Article in Japanese]
Furukawa K, Chairungsrilerd N, Ohta T, Nozoe S, Ohizumi Y.
Department of Pharmaceutical Molecular Biology, Faculty of Pharmaceutical Sciences, Tohoku University, Sendai, Japan.
A crude methanolic extract of the fruit hull of Garcinia mangostana L. inhibited the contraction of the isolated rabbit aorta induced by histamine and serotonin. The extract has been fractionated by silica gel chromatography, monitoring the pharmacological activity to give active compounds. On the basis of physicochemical data, the active substances were identified as alpha-mangostin and gamma-mangostin. To define the pharmacological properties of alpha-mangostin, the effect of alpha-mangostin on both histamine H1 and H2 receptors were examined by monitoring the mechanical responses of smooth muscles and measuring the radioligand binding to cultured vascular smooth muscle cells. The results suggest that alpha-mangostin acts as a selective and competitive histamine H1 receptor antagonist. The pharmacological actions of gamma-mangostin on 5-HT receptors were also investigated by using contractile response of vascular smooth muscle, platelet aggregation and radioligand binding studies. The results provide the evidence that gamma-mangostin is a selective and competitive 5-HT2A receptor antagonist. It is of great interest that the structures of alpha-mangostin and gamma-mangostin free from nitrogen atom are not resemble to the common structures of histamine and serotonin receptor antagonists. alpha-Mangostin and gamma-mangostin may become novel types of lead compounds for histamine and serotonin receptor antagonists.
PMID: 9503424 [PubMed - indexed for MEDLINE]
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Naunyn Schmiedebergs Arch Pharmacol. 1998 Jan;357(1):25-31.
Gamma-mangostin, a novel type of 5-hydroxytryptamine 2A receptor antagonist.
Chairungsrilerd N, Furukawa KI, Ohta T, Nozoe S, Ohizumi Y.
Department of Pharmaceutical Molecular Biology, Faculty of Pharmaceutical Sciences, Tohoku University, Sendai, Japan.
Gamma-mangostin, purified from the fruit hull of the medicinal plant Garcinia mangostana caused a parallel rightwards shift of the concentration/response curve for the contraction elicited by 5-hydroxytryptamine (5-HT) in the rabbit aorta (pA2 = 8.2) without affecting the contractile responses to KCl, phenylephrine (alpha1) or histamine (H1). The perfusion pressure response of rat coronary artery to 5-HT (5-HT2A) was reduced concentration dependently by gamma-mangostin (IC50 = 0.32 microM). 5-HT amplified, ADP-induced aggregation of rabbit platelets (5-HT2A) was inhibited by gamma-mangostin (IC50 = 0.29 microM), whereas that induced by thrombin was not affected, nor did gamma-mangostin affect 5-HT-induced contraction of the guinea-pig ileum (5-HT3)in the presence of 5-HT1, 5-HT2 and 5-HT4 receptor antagonists. Furthermore, 5-HT-induced contraction of the rat fundus (5-HT2B) and 5-HT-induced relaxation of the rabbit aorta in the presence of ketanserin (5-HT1) and carbachol-induced contraction of the guinea-pig ileum (muscarinic M3) were not affected by gamma-mangostin (5 microM). Gamma-mangostin inhibited [3H]spiperone binding to cultured rat aortic myocytes (IC50 = 3.5 nM). The Kd for [3H]spiperone binding was increased by gamma-mangostin (3 nM) from 11.7 to 27.4 nM without affecting Bmax. These results suggest that gamma-mangostin is a novel competitive antagonist, free from a nitrogen atom, for the 5-HT2A receptors in vascular smooth muscles and platelets.
PMID: 9459569 [PubMed - indexed for MEDLINE]
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J Nat Prod. 1997 May;60(5):519-24.
Evaluation of the antifungal activity of natural xanthones from Garcinia mangostana and their synthetic derivatives.
Gopalakrishnan G, Banumathi B, Suresh G.
Centre for Agrochemical Research, SPIC Science Foundations, Madras, India.
The antifungal activity of several xanthones isolated from the fruit hulls of Garcinia mangostana and some derivatives of mangostin against three phytopathogenic fungi, Fusarium oxysporum vasinfectum, Alternaria tenuis, and Dreschlera oryzae, has been evaluated. The natural xanthones showed good inhibitory activity against the three fungi. Substitution in the A and C rings has been shown to modify the bioactivities of the compounds.
PMID: 9213587 [PubMed - indexed for MEDLINE]
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Planta Med. 1996 Aug;62(4):381-2.
Active constituents against HIV-1 protease from Garcinia mangostana.
Chen SX, Wan M, Loh BN.
The ethanol extract of Garcinia mangostana L. (Guttiferae) showed potent inhibitory activity against HIV-1 protease. The activity-guided purification of the extract resulted in the isolation of two active, known compounds. The chemical structures of the isolated compounds were established by spectroscopic analyses as mangostin (IC50 = 5.12 +/- 0.41 microM) and gamma-mangostin (IC50 = 4.81 +/- 0.32 microM). The type of inhibition by both compounds is noncompetitive.
Publication Types:
• Letter
PMID: 8792678 [PubMed - indexed for MEDLINE]
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Free Radic Res. 1995 Aug;23(2):175-84.
Mangostin inhibits the oxidative modification of human low density lipoprotein.
Williams P, Ongsakul M, Proudfoot J, Croft K, Beilin L.
University of Western Australia, Department of Medicine, Royal Perth Hospital, Australia.
The oxidation of low density lipoprotein (LDL) may play an important role in atherosclerosis. We investigated the possible antioxidant effects of mangostin, isolated from Garcinia mangostana, on metal ion dependent (Cu2+) and independent (aqueous peroxyl radicals) oxidation of human LDL. Mangostin prolonged the lagtime to both metal ion dependent and independent oxidation of LDL in a dose dependent manner over 5 to 50 microM as monitored by the formation of conjugated dienes at 234 nm (P < 0.001). There was no significant effect of mangostin on the rate at which conjugated dienes were formed in the uninhibited phase of oxidation. Levels of thiobarbituric reactive substances (TBARS) generated in LDL were measured 4 and 24 hours after oxidation with 5 microM Cu2+ in the presence or absence of 50 microM or 100 microM mangostin. We observed an inhibition of TBARS formation with 100 microM mangostin at 4 hours (P = 0.027) but not at 24 hours (P = 0.163). Similar results were observed in the presence of 50 microM mangostin. Mangostin, at 100 microM, retarded the relative electrophoretic mobility of LDL at both 4 and 24 hours after Cu2+ induced oxidation. Mangostin (100 microM) significantly inhibited the consumption of alpha-tocopherol in the LDL during Cu2+ initiated oxidation over a 75 minute period (P < 0.001). From these results, we conclude that mangostin is acting as a free radical scavenger to protect the LDL from oxidative damage in this in vitro system.
PMID: 7581813 [PubMed - indexed for MEDLINE]
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Planta Med. 1983 May;48(1):59-60.
Antimicrobial activities of Garcinia mangostana.
Sundaram BM, Gopalakrishnan C, Subramanian S, Shankaranarayanan D, Kameswaran L.
PMID: 6611746 [PubMed - indexed for MEDLINE]
The Mangosteen Tree is trully a gift of nature.
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J Enzyme Inhib. 2000;15(2):129-38.
Inhibition of acidic sphingomyelinase by xanthone compounds isolated from Garcinia speciosa.
Okudaira C, Ikeda Y, Kondo S, Furuya S, Hirabayashi Y, Koyano T, Saito Y, Umezawa K.
Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-0061, Japan.
Sphingomyelinase is considered to be involved in the regulation of apoptosis and cell growth. In the course of our screening for acidic sphingomyelinase inhibitors we isolated three xanthone compounds, alpha-mangostin, cowanin, and cowanol, from the bark of Garcinia speciosa. These compounds competitively inhibited bovine brain-derived acidic sphingomyelinase with IC(50) values of 14.1, 19.2, and 10.9 microM, respectively and inhibited the acidic sphingomyelinase more effectively than the neutral sphingomyelinase of bovine brain. alpha-Mangostin inhibited the acidic sphingomyelinase in the most selective manner. alpha-Mangostin was chemically modified and its structure-activity relationships are discussed.
PMID: 10938539 [PubMed - indexed for MEDLINE]
