Cytotoxic Xanthones from Garcinia penangiana Pierre (original) (raw)
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Cytotoxic Xanthones from the Leaves of Garcinia Urophylla
Natural Product Communications, 2007
Two new xanthones, 7-hydroxydesoxymorellin (1) and isocaledonixanthone D (2), and four known ones, gaudichaudione H, 1,7-dihydroxy-3-methoxy-2-(3-methyl-2-butenyl)xanthone, 1,5-dihydroxy-3-methoxy-2-(3-methyl-2-butenyl)xanthone, and 1,3,7-trihydroxy-2-(3-methyl-2-butenyl)xanthone, as well as lupeol were isolated from the leaves of Garcinia urophylla (Guttiferae). Their structures were determined using a combination of 1D (1H NMR, 13C NMR, DEPT) and 2D (COSY, gHSQC, gHMBC) NMR spectroscopic techniques. Among the isolates, 7-hydroxydesoxymorellin (1), gaudichaudione H, 1,5-dihydroxy-3-methoxy-2-(3-methyl-2-butenyl)xanthone, and 1,3,7-trihydroxy-2-(3-methyl-2-butenyl)xanthone demonstrated cytotoxic activities against breast (MCF-7), prostate (DU-145), and lung (NCI-H460) human cancer cell lines.
A new cytotoxic xanthone from Garcinia rigida
Fitoterapia, 2008
A new xanthone, yahyaxanthone (1), was isolated from Garcinia rigida leaves. Cytotoxicity evaluation showed that 1 was inhibitory to L1210 cell, with an IC 50 value 4.08 μg/ml.
Cytotoxic xanthones from the stem bark of Garcinia cowa Roxb
The aims of this study was to isolate compounds from the methanol extract of stem bark of Garcinia cowa and to evaluated their cytotoxic activity against breast (MCF-7) and lung (H-460) cancer cell lines. The ethyl acetate fraction was separated by successive silica gel column chromatography to give three compounds. Based on spectroscopic comparison with those of the literature, these compounds were elucidated as 6-hydroxy- calabaxanthone (2), 2-(3-methyl-2-butenyl)-1,5,6-trihydroxy-3-methoxy-4-(1,1-dimethyl-2-propenyl)-9H-xanthen-9- one(3), rubraxanthone (4), α-mangostin (5), a new compound 1,3,6-trihydoxy-7-methoxy-4-(4-acetoxy-3-methyl-2- butenyl)-8-(3,7-dimethyl-2,6-octadienyl)xanthone (6) and cowanin (7). Complete NMR assignment of 6-hydroxy- calabaxanthone (2) and cowanin (7) were published for the first time. All isolated compounds were subjected to MTT assay against MCF-7, H-460 and DU-145 cancer cell lines. α-mangostin (5) and cowanin (7) were found to be potent against MCF-7 while 6-hydroxy-calabaxanthone (2) potent against DU-145 cell lines. Conclusion: The results indicate that G. cowa stem bark could be one of important sources of natural cytotoxic compounds.
Antiproliferative activity of a new xanthone derivative from leaves of Garcinia nobilis Engl
Natural Product Research, 2020
A new xanthone, mboudiexanthone (1), together with five known compounds, euxanthone (2), isogarcinol (3), garcinol (4), betulinic acid (5) and zeorin (6) were isolated from the leaves of Garcinia nobilis Engl. The structures were determined by 1D and 2D NMR techniques and X-ray diffraction for 6. The in vitro antiproliferative properties of isolated compounds were evaluated against the human breast cancer cell line MCF-7. All compounds showed an antiproliferative activity with an IC 50 value down to $11 mM for isogarcinol.
Garcixanthone A, a new cytotoxic xanthone from the pericarps of Garcinia mangostana
Journal of Asian natural products research, 2018
A new prenylated xanthone, garcixanthone A (5), together with eight known compounds, mangostanaxanthones I (1) and II (2), garcinone E (3), β-mangostin (4), 8-hydroxycudraxanthone G (6), garcinone C (7), cudraxanthone G (8), and (-)-epicatechin (9) were isolated from the EtOAc-soluble fraction of the air-dried pericarps of Garcinia mangostana (family Clusiaceae). Their structures were verified on the basis of spectroscopic data interpretation as well as comparison with the literature. The cytotoxic and antimicrobial activities of the new compound were assessed using sulforhodamine B (SRB) and agar disk diffusion assays, respectively. Compound 5 showed significant cytotoxic potential against epithelial lung carcinoma (A549) and breast carcinoma (MCF7) cell lines with IC50s 3.0 and 4.2 μM, respectively, compared to doxorubicin (0.74 and 0.41 μM, respectively).
Phytochemistry Letters, 2018
Two new prenylated xanthones, garcixanthones B (1) and C (2) and six known metabolites: gartanin (3), 1,3,8trihydroxy-2-(3-methyl-2-butenyl)-4-(3-hydroxy-3-methylbutanoyl)-xanthone (4), rubraxanthone (5), 1,3,6,7tetrahydroxy-8-prenylxanthone (6), garcinone C (7), and xanthone I (9-hydroxycalabaxanthone) (8) were separated from the EtOAc-soluble fraction of the air-dried pericarps of Garcinia mangostana (Clusiaceae). Their structures were verified on the basis of spectroscopic data analysis as well as by comparison with the literature. The cytotoxic activity of the new compounds was assessed against MCF7, A549, and HCT116 cell lines using sulforhodamine B (SRB) assay. Compounds 1 and 2 showed significant cytotoxic potential against MCF7 (human breast adenocarcinoma) and A549 (lung carcinoma) cell lines with IC 50 s 4.27 and 2.65 and 3.08 and 3.91 μM, respectively compared to doxorubicin (0.06 and 0.44 μM, respectively). However, they exhibited moderate activity towards HCT116 (colon carcinoma) cell line.
Biphenyl and xanthone derivatives from the twigs of a Garcinia sp. (Clusiaceae)
Phytochemistry Letters, 2014
The genus Garcinia is a well known rich source of bioactive xanthones and benzophenones. Some species of this genus also produce flavonoids and biphenyls as minor constituents. In this study, two new biphenyls, doitungbiphenyls A (1) and B (2), along with two biphenyls, schomburgbiphenyl (3) and nigrolineabiphenyl B (4); and four xanthones, 1,3,6-trihydroxy-8-isoprenyl-7-methoxyxanthone (5), morusignin K (6), 1,5-dihydroxyxanthone (7), and 1,7-dihydroxyxanthone (8), were isolated from the acetone extract of the twigs of a Garcinia sp. Their structures were characterized extensively by 1D and 2D NMR spectroscopy and HR-EI-MS. The cytotoxicity of the two new biphenyls against the oral cavity cancer (KB) and the breast cancer (MCF7) cell lines was also evaluated.
Cytotoxic caged-polyprenylated xanthonoids and a xanthone from Garcinia cantleyana
Phytochemistry, 2007
Phytochemical studies on the leaves and trunk bark of Garcinia cantleyana yielded five caged-xanthonoids including one tetra- and four tri-prenylated xanthones, cantleyanone A (1), 7-hydroxyforbesione (2) and cantleyanones B–D (4–6), as well as a simple xanthone, 4-(1,1-dimethylprop-2-enyl)-1,3,5,8-tetrahydroxyxanthone (3). Eight other known compounds, deoxygaudichaudione A, gaudichaudione H, friedelin, garbogiol, macranthol, glutin-5-en-3β-ol, and a mixture of sitosterol and stigmasterol were also isolated. Their structures were elucidated by means of spectroscopic data and comparison of their NMR data with literature values. Significant cytotoxicity against MDA-MB-231, CaOV-3, MCF-7 and HeLa cancer cell-lines was demonstrated by cantleyanones B–D, 7-hydroxyforbesione, deoxygaudichaudione A and macranthol, with IC50 values ranging from 0.22 to 17.17 μg/ml.Five caged-xanthonoids, cantleyanone A (1), 7-hydroxyforbesione (2), cantleyanones B–D (4–6) and a simple xanthone, 4-(1,1-dimethylprop-2-enyl)-1,3,5,8-tetrahydroxyxanthone (3) together with eight other known compounds were isolated from Garcinia cantleyana. Significant cytotoxicity against MDA-MB-231, CaOV-3, MCF-7 and HeLa cancer cell-lines were demonstrated by cantleyanones B–D, 7-hydroxyforbesione, deoxygaudichaudione A and macranthol, with IC50 values ranging from 0.22 to 17.17 μg/ml.