Four new cytotoxic xanthones from Garcinia nujiangensis

Tang, Zhongyan; Xia, Zheng-xiang; Qiao, Shi-ping; Jiang, Chao; Guo-rong, Shen; Cai, Meixiang; Tang, Xiao‐Yan

doi:10.1016/j.fitote.2015.02.011

Cited by 27 publications

(22 citation statements)

References 13 publications

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“…A MeOH extract of the stem bark of G. propinqua was dissolved in H 2 O and partitioned with CH 2 Cl 2 and EtOAc. A combination of the CH 2 Cl 2 and EtOAc extracts was separated by chromatographic techniques resulting in the isolation of seven new caged xanthones (1)(2)(3)(4)(5)(6)(7) together with 10 known compounds, xerophenone A (8), 34 doitunggarcinones A (9) 2, 35 and B (10), 2,35 sampsonione B (11), 36 7β-H-11-benzoyl-5α-hydroxy-6,6,10,10-tetramethyl-1-(3methyl-2-butenyl)tetracyclo [7.3.1.1 3,11 0 3,7 ]tetradecane-2,12,14-trione (12), 37 hypersampsone M (13), 38 assiguxanthone A (14), 39 cudraxanthone Q (15), 40 10-O-methylmacluraxanthone (16), 41 and 5-O-methylxanthone V 1 (17). 12 Compound 1 was obtained as a white solid (m.p.…”

Section: Resultsmentioning

confidence: 99%

“…The structure was solved by direct methods. The absolute configurations of (+)-1 was assigned as (5S, 6R, 7R, 8S, 8aS, 10as, 17R, 22S) with a Flack x-parameter of 0.01 (6) NMR spectra for all new compounds (1-7), and details for the X-ray single crystal structure of (+)-1.…”

Section: X-ray Crystallographic Analysis Of Compound (+)-1mentioning

confidence: 99%

“…[26][27][28][29][30] Many of these compounds have a wide range of biological and pharmacological activities, including antimicrobial, 29,31 antidepressant, 29 anti-HIV, 29,32 antibacterial, 2,3,9,10,18,22 and cytotoxic activities. 6,8,[12][13][14][15][16][17]27,29 In a previous paper we reported the isolation of xanthones, caged…”

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confidence: 99%

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Scalemic Caged Xanthones Isolated from the Stem Bark Extract of Garcinia propinqua

et al. 2017

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Seven new caged xanthones, doitunggarcinones E-K (1-7), all as scalemic mixtures and 10 known compounds (8-17), were isolated from the stem bark extract of Garcinia propinqua. The structures were elucidated on the basis of spectroscopic methods. The separation of the enantiomers of 1-6 was achieved by semipreparative chiral HPLC. The absolute configuration of compound (+)-1 was determined by single-crystal X-ray crystallographic analysis using Cu Kα radiation. The absolute configurations of the other related compounds were determined from comparisons of their ECD spectra with that of compound (+)-1. Compounds (-)-6 and 7 showed cytotoxicity against a colon cancer cell line with IC values of 14.23 and 23.95 μM, respectively.

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Section: Resultsmentioning

confidence: 99%

Section: X-ray Crystallographic Analysis Of Compound (+)-1mentioning

confidence: 99%

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Scalemic Caged Xanthones Isolated from the Stem Bark Extract of Garcinia propinqua

et al. 2017

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“…Xanthone compound was also reported for having some activities as anticancer, [7][8][9] antitumor, [10][11] antioxidant, 12-13 cytotoxic, [14][15][16] leukemia, 17 antidiabetic. 18 These facts show that xanthone has tremendous potential activities.…”

Section: Introductionmentioning

confidence: 99%

Xanthone as Antimalarial: QSAR Analysis, Synthesis, Molecular Docking and In-vitro Antimalarial Evaluation

Syahri¹,

Yuanita²

2017

Orient. J. Chem

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The rational design of eighteen new antimalarial compounds from xanthone derivatives has been conducted based on Quantitative Structure-Activity Relationship (QSAR) calculation using semiempirical AM1 methods. The best equation model obtained from QSAR calculation was Log pIC 50 = 2.997 -29.256 (qO8) -138.234 (qC9) -6.882 (qC12) -107.836 (qC14) + 48.764 (qO15). Among the designed compounds, 3,6-dihydroxy-9H-xanthen-9-one (26) and 3,4,6-trihydroxy-9H-xanthen-9-one (27) have been synthesized and investigated their in-vitro antimalarial activities against the chloroquine-sensitive 3D7 strain. An in-vitro antimalarial activity of compound 26 and 27 showed to be highly potential as antimalarial compounds with IC 50 of 0.71 and 0.11 µM respectively. Molecular docking studies of compound 26 and 27 showed the formation of a binding interaction between the compounds with the amino acids Ala16, Ser108, Phe58, Asp54 and Leu46, which is the crucial amino acids for antimalarial activity based on the protein-ligand co-crystal structure of WR99210 (1,3,5-triazine, a pre-clinical molecule as P. falciparum DHFR-TS inhibitor).

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“…Although chemotherapy is still an important means of tackling cancers nowadays, low efficiency, severe side effects, and especially multidrug resistance (MDR) become main impediments to achieve a satisfying efficacy in long-term treatments [ 10 ]. Available evidences show xanthones have growth inhibitory potency against various tumor cell lines including some MDR types [ 11 – 14 ]. We also found MDR NSCLC lung tumor cell line A549/Taxol was sensitive to xanthones from SI.…”

Section: Introductionmentioning

confidence: 99%

Regulation of MAPKs Signaling Contributes to the Growth Inhibition of 1,7‐Dihydroxy‐3,4‐dimethoxyxanthone on Multidrug Resistance A549/Taxol Cells

Zuo

Jiang

Zhu

et al. 2016

Evidence-Based Complementary and Alternative Medicine

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1,7-Dihydroxy-3,4-dimethoxyxanthone (XAN) is a bioactive compound isolated from Securidaca inappendiculata Hassk. and validated with antiproliferative activities on a panel of cancer cell lines. This study was designed to investigate its growth inhibitory effects on multidrug resistance (MDR) non-small cell lung carcinoma (NSCLC) cell line A549/Taxol and explore the possible linkage between modulation of MAPKs and the bioactivities. Its growth inhibitory potency on the cells was estimated by MTT assay, and flow cytometric analysis was employed to investigate its potential cell cycle arrest and proapoptosis effects. Expressions of hallmark proteins were assessed by Western-Blot method. The results showed A549/Taxol cells were sensitive to XAN. XAN inhibited the proliferation of A549/Taxol cells in the time and concentration dependent manners. It acted as a potent inducer of apoptosis and cell cycle arrest in the cells. Western-Blot investigation validated the proapoptosis and cell cycle arrest activities of XAN and the potential of MDR reversion. Upregulation of p38 by XAN, which accounted for the cell cycle arrest at G2 phase, and the downregulation of ERK associated with the proapoptosis activity were also revealed. Further analysis found p53 may be the central role mediated the bioactivities of MAPKs in A549/Taxol cells. Based on these evidences, a conclusion has been deduced that XAN could be a potential agent for MDR NSCLC therapy targeting specifically MAPKs.

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Four new cytotoxic xanthones from Garcinia nujiangensis

Cited by 27 publications

References 13 publications

Scalemic Caged Xanthones Isolated from the Stem Bark Extract of Garcinia propinqua

Scalemic Caged Xanthones Isolated from the Stem Bark Extract of Garcinia propinqua

Xanthone as Antimalarial: QSAR Analysis, Synthesis, Molecular Docking and In-vitro Antimalarial Evaluation

Regulation of MAPKs Signaling Contributes to the Growth Inhibition of 1,7‐Dihydroxy‐3,4‐dimethoxyxanthone on Multidrug Resistance A549/Taxol Cells

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