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Gambogellic acid

目录号 : GC38024

Gambogellic acid 是从加工过的藤黄中分离得到的氧杂蒽酮类化合物,具有抗肿瘤活性。

Gambogellic acid Chemical Structure

Cas No.:173867-04-4

规格 价格 库存 购买数量
1mg
¥810.00
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5mg
¥2,421.00
现货
10mg
¥4,113.00
现货

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产品描述

Gambogellic acid is an xanthone isolated from the processed gamboge, with antitumor activity[1].

[1]. Dong B, et al. Two new xanthone epimers from the processed gamboge. Nat Prod Res. 2017 Apr;31(7):817-821.

Chemical Properties

Cas No. 173867-04-4 SDF
Canonical SMILES CC(C1C2C[C@](CC1)(C)OC3=C(C/C=C(C)/C)C4=C(C(C([C@]56O4)=C[C@H]7C([C@]5(C/C=C(C)/C(O)=O)OC(C)(C)[C@H]6C7)=O)=O)C(O)=C23)=C
分子式 C38H44O8 分子量 628.75
溶解度 Soluble in DMSO 储存条件 Store at -20°C
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溶解性数据

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1 mg 5 mg 10 mg
1 mM 1.5905 mL 7.9523 mL 15.9046 mL
5 mM 0.3181 mL 1.5905 mL 3.1809 mL
10 mM 0.159 mL 0.7952 mL 1.5905 mL
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Research Update

Studies on chemical modification and biology of a natural product, gambogic acid (II): Synthesis and bioevaluation of Gambogellic acid and its derivatives from gambogic acid as antitumor agents

Eur J Med Chem 2010 Sep;45(9):4343-53.PMID:20605273DOI:10.1016/j.ejmech.2010.04.037.

Gambogic acid (GA) has been reported to be a potent apoptosis inducer. The fact that it is amenable to chemical modification makes GA an attractive molecule for the development of anticancer agents. We firstly reported the synthesis of Gambogellic acid, which was generated under acid catalysis from readily available GA by a base-catalyzed diene intramolecular annelation. Sequentially, thirteen new compounds were synthesized and their inhibitory activity on HT-29, Bel-7402, BGC-823, and A549 cell lines were evaluated in vitro by MTT assay, and (38, 40)-epoxy-33-chlorogambogellic acid (4) was identified as a BGC-823 cell apoptosis inducer through MTT cell assay, observations of morphological changes, and Annexin-V/PI double-staining assay. Compound 4 showed significant effects in inducing apoptosis and might serve as a potential lead compound for discovery of new anticancer drugs. Further structure-activity relationships (SARs) of gambogic acid derivatives were discussed.

Two new xanthone epimers from the processed gamboge

Nat Prod Res 2017 Apr;31(7):817-821.PMID:27809607DOI:10.1080/14786419.2016.1247079.

Two new xanthones, gambogollic acid (1), epigambogollic acid (2), together with three rare compounds, Gambogellic acid (3), epigambogellic acid (4) and gambogic acid (5), were isolated from the processed gamboge. The new structures were determined by 1D and 2D NMR spectroscopic analysis. And the cytotoxicity of these five compounds was evaluated against human hepatoma carcinoma and human lung adenocarcinoma cell. Two new compounds showed excellent antitumor activity. All five compounds exhibited inhibitory effect against SMMC-7221cell and A549 cell.

Cytotoxic xanthones from Garcinia hanburyi

Phytochemistry 1996 Feb;41(3):815-20.PMID:8835458DOI:10.1016/0031-9422(95)00682-6.

Eleven novel cytotoxic xanthones, gambogin, morellin dimethyl acetal, isomoreollin B, moreollic acid, gambogenic acid, gambogenin, isogambogenin, desoxygambogenin, gambogenin dimethyl acetal, Gambogellic acid and hanburin were isolated together with four known xanthones, gambogic acid, isomorellin, morellic acid and desoxymorellin, from the dry latex of Garcinia hanburyi. The structures were elucidated by a detailed spectroscopic analysis.

Improved high-performance liquid chromatographic method for simultaneous determination of 12 cytotoxic caged xanthones in gamboges, a potential anticancer resin from Garcinia hanburyi

Biomed Chromatogr 2008 Jun;22(6):637-44.PMID:18254140DOI:10.1002/bmc.981.

The potential anti-tumor activity of gamboges, a herbal medicine derived from Garcinia hanburyi, has increasingly gained the interest of scientist worldwide. The major components of gamboges are cytotoxic caged xanthones. In the present study, an improved HPLC method was developed to simultaneously quantify 12 caged xanthones, including three pairs of epimers and four pairs of trans-cis isomers, i.e. forbesione, isomorellic acid, morellic acid, R-30-hydroxygambogic acid, S-30-hydroxygambogic acid, isogambogenic acid, gambogenic acid, Gambogellic acid, R-isogambogic acid, S-isogambogic acid, R-gambogic acid and S-gambogic acid. This method was validated to be sensitive, precise and accurate with limits of detection of 0.03-0.08 microg/mL, overall intra-day and inter-day variations less than 7.9% and overall recovery over 93.2%. The correlation coefficients (r(2)) of the calibration curves were higher than 0.995 for all analytes. The newly established method was successfully applied to reveal the difference in the chemical profiles and contents of these analytes in gamboges from different origins. It can be concluded that this method was not only an effective quality control method to ensure the safety and efficacy consistency of gamboges, but also a useful tool for screening and determining more potent cytotoxic xanthones with potential anticancer activity.