Design and synthesis of gambogic acid analogs as potent cytotoxic and anti-inflammatory agents

Yen, Chiao Ting; Nakagawa‐Goto, Kyoko; Hwang, Tsong‐Long; Morris‐Natschke, Susan L.; Bastow, Kenneth F.; Wu, Yang Chang; Lee, Kuo Hsiung̀

doi:10.1016/j.bmcl.2012.04.084

Cited by 24 publications

(16 citation statements)

References 25 publications

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“…The neutrophil-mediated inflammatory response is regarded as a multi-step process involving the initial adhesion of circulating neutrophils to activated vascular endothelium [43]. In fMLP/CB-stimulated human neutrophils, several gambogic acid analogs (23, 24, 29, 31, 32, 34, and 35) inhibited superoxide anion generation and elastase release [44]. Several xanthons (3, 9, 42, and 43) were isolated from the twigs of Hypericum oblongifolium wall, which showed anti-inflammatory activity in isolated human neutrophils [45].…”

Section: Xanthones With Anti-inflammatory Propertiesmentioning

confidence: 99%

Xanthones, A Promising Anti-Inflammatory Scaffold: Structure, Activity, and Drug Likeness Analysis

Feng

Gan

et al. 2020

Molecules

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Inflammation is the body’s self-protective response to multiple stimulus, from external harmful substances to internal danger signals released after trauma or cell dysfunction. Many diseases are considered to be related to inflammation, such as cancer, metabolic disorders, aging, and neurodegenerative diseases. Current therapeutic approaches include mainly non-steroidal anti-inflammatory drugs and glucocorticoids, which are generally of limited effectiveness and severe side-effects. Thus, it is urgent to develop novel effective anti-inflammatory therapeutic agents. Xanthones, a unique scaffold with a 9H-Xanthen-9-one core structure, widely exist in natural sources. Till now, over 250 xanthones were isolated and identified in plants from the families Gentianaceae and Hypericaceae. Many xanthones have been disclosed with anti-inflammatory properties on different models, either in vitro or in vivo. Herein, we provide a comprehensive and up-to-date review of xanthones with anti-inflammatory properties, and analyzed their drug likeness, which might be potential therapeutic agents to fight against inflammation-related diseases.

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Section: Xanthones With Anti-inflammatory Propertiesmentioning

confidence: 99%

Xanthones, A Promising Anti-Inflammatory Scaffold: Structure, Activity, and Drug Likeness Analysis

Feng

Gan

et al. 2020

Molecules

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“…It was isolated from Gamboge (the resin of Garcinia hanburyi Hook. In addition to significant anti-tumor effects, GA also exhibits anti-inflammatory, detoxification and parasiticide effects (Yen et al, 2012;Wen et al, 2014;Rahman et al, 2013). Gamboge possesses anti-inflammatory, anti-viral and anti-cancer effects (Xu and Yang, 2013;Yen et al, 2012;Wen et al, 2014;Kong et al, 1996).…”

Section: Introductionmentioning

confidence: 99%

“…F., a traditional Chinese medicine). Gamboge possesses anti-inflammatory, anti-viral and anti-cancer effects (Xu and Yang, 2013;Yen et al, 2012;Wen et al, 2014;Kong et al, 1996). As a promising natural anti-cancer candidate, GA's activity in numerous types of cancer cells has been well demonstrated in vivo and in vitro, including leukemia, lung, liver, SH-SY5Y neuroblastoma, breast, colorectal, U87 glioma, ovarian and gastrointestinal cancer cells Zhang et al, 2014;Qi et al, 2014;Duan et al, 2014;He et al, 2013;Wang and Yuan, 2013;Rahman et al, 2013;Li et al, 2012;Zou et al, 2012).…”

Section: Introductionmentioning

confidence: 99%

“…As a promising natural anti-cancer candidate, GA's activity in numerous types of cancer cells has been well demonstrated in vivo and in vitro, including leukemia, lung, liver, SH-SY5Y neuroblastoma, breast, colorectal, U87 glioma, ovarian and gastrointestinal cancer cells Zhang et al, 2014;Qi et al, 2014;Duan et al, 2014;He et al, 2013;Wang and Yuan, 2013;Rahman et al, 2013;Li et al, 2012;Zou et al, 2012). In addition to significant anti-tumor effects, GA also exhibits anti-inflammatory, detoxification and parasiticide effects (Yen et al, 2012;Wen et al, 2014;Rahman et al, 2013). However, although GA shows various pharmacological activities, information regarding the in vivo fate of GA is still limited.…”

Section: Introductionmentioning

confidence: 99%

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UHPLC‐MS method for determination of gambogic acid and application to bioavailability, pharmacokinetics, excretion and tissue distribution in rats

Zheng

Zhang

et al. 2015

Biomedical Chromatography

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A sensitive ultrahigh performance liquid chromatography tandem mass spectrometry (UHPLC-MS) method was developed for determination of gambogic acid (GA) in rat plasma, urine, bile and main tissues. GA was separated on an Agilent Zorbax XDB-C18 column (50 × 2.1 mm, 1.8 µm) with gradient mobile phase at the flow rate of 0.2 mL/min. The detection was performed by negative electrospray ionization with multiple reaction monitoring mode. The calibration curves of GA were linear between 1.0 and 1000 ng/mL in rat plasma and bile and between 1.0 and 500 ng/mL in urine and tissues. The lowest limit of quantification for all matrices was 1.0 ng/mL. Both accuracy and precision of the assay were satisfactory. This validated method was firstly applied to bioavailability (BA), pharmacokinetics, excretion and tissue distribution in rats. The BAs of GA (40 and 80 mg/kg) in rats were 0.25 and 0.32%, respectively. GA was distributed extensively in rats after oral administration and exhibited the highest level in liver. GA reached the cumulative excretion amount of 25.3 ± 1.7 µg in bile and 0.275 ± 0.08 µg in urine after i.g. 80 mg/kg to rats at 24 h. The present results would be helpful for further clinical use of GA as a potential anticancer drug.

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“…其一是水杨酸类化合物在伊顿试剂的催化作用下与间苯三酚发生 Friedel-Craft 酰化 (1) 以伊顿试剂为催化剂合成呫吨酮类化合物已有文献报道 [28] . 亚硝酸钠标准溶液的配制: 准确称取在硅胶干燥器中干燥了 24 h 的亚硝酸钠 0.1000 g, 加水溶解, 定容至 250 mL(浓度为 400 μg/mL), 作为储备液.…”

Section: 呫吨酮类化合物的合成有多种方法胡利红等unclassified

Concise Syntheses of 1,3-Dihydroxylxanthones and Their Clearance Effections against Nitrite

毛双双¹,

郑欢欢²,

罗翠婷³

et al. 2014

Chin. J. Org. Chem.

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Twelve 1,3-dihydroxylxanthones (3a～3l) were synthesized under the catalysis of Eaton's reagent applying phloroglucinol and substituted salicylic acids as starting materials. The yields were from 63% to 87%. The reaction mechanism and their structure-reaction activity relationship have been discussed. The clearance effections of all the prepared xanthones against nitrite have been investigated by UV spectrophotometry. It is disclosed that all the tested xanthones have obvious clearance effections against nitrite at the conditions of pH 3, room temperature, and 30 min treatment. 3b and 3f are identified as the most active compounds with clearance rate up to 34.0%. The clearance mechanism of xanthones against nitrite and their structure-activity relationships were also included here.

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Design and synthesis of gambogic acid analogs as potent cytotoxic and anti-inflammatory agents

Cited by 24 publications

References 25 publications

Xanthones, A Promising Anti-Inflammatory Scaffold: Structure, Activity, and Drug Likeness Analysis

Xanthones, A Promising Anti-Inflammatory Scaffold: Structure, Activity, and Drug Likeness Analysis

UHPLC‐MS method for determination of gambogic acid and application to bioavailability, pharmacokinetics, excretion and tissue distribution in rats

Concise Syntheses of 1,3-Dihydroxylxanthones and Their Clearance Effections against Nitrite

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