Structural Elucidation and Biomimetic Synthesis of (+/-)-Cochlactone A with Anti-Inflammatory Activity
Peng, Xing-Rong1; Lu, Shuang-Yang1,2; Shao, Li-Dong1; Zhou, Lin1; Qiu, Ming-Hua1,2
2018-05-18
Source PublicationJOURNAL OF ORGANIC CHEMISTRY
ISSN0022-3263
Volume83Issue:10Pages:5516-5522
Abstract

A pair of new natural meroterpenoids, (+/-)-cochlactone A (1) possessing a bicyclo[4.4.0]decane ring system with a gamma-lactone fragment, was isolated from Ganoderma cochlear. To further confirm their absolute configurations, a high-yielding, one-step biomimetic synthesis of (+/-)-cochlactone A (1) from ganomycin C (3) was conducted. In addition, a new compound, (+/-)-cochlactone B (2), featuring a bicyclo[3.3.1]decane fragment fused to a gamma-lactone moiety was synthesized. Their structures were determined using spectroscopic data, X-ray diffraction crystallography, and electronic circular dichroism (ECD) analyses. Furthermore, a plausible reaction mechanism for the formation of 1 and 2 was proposed. Compounds (+)-2 and (+/-)-2 showed inhibitory effects against Staphylococcus aureus with MIC50 values of 41.1 +/- 0.1 and 64.0 +/- 2.6 mu g/mL, respectively. Meanwhile, (+/-)-1, (+/-)-1, (+)-2, and (+/-) displayed significant anti-inflammatory activities (IC50: 5.9 +/- 0.1, 6.1 +/- 0.2, 12.1 +/- 0.4, and 18.7 +/- 1.9 mu M, respectively).

DOI10.1021/acs.joc.8b00525
Language英语
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Cited Times:2[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/61332
Collection植物化学与西部植物资源持续利用国家重点实验室
Affiliation1.Chinese Acad Sci, Kunming Inst Bot, Key Lab Phytochem & Plant Resources West China, Kunming 650201, Yunnan, Peoples R China
2.Chinese Acad Sci, Grad Univ, Beijing 100049, Peoples R China
Recommended Citation
GB/T 7714
Peng, Xing-Rong,Lu, Shuang-Yang,Shao, Li-Dong,et al. Structural Elucidation and Biomimetic Synthesis of (+/-)-Cochlactone A with Anti-Inflammatory Activity[J]. JOURNAL OF ORGANIC CHEMISTRY,2018,83(10):5516-5522.
APA Peng, Xing-Rong,Lu, Shuang-Yang,Shao, Li-Dong,Zhou, Lin,&Qiu, Ming-Hua.(2018).Structural Elucidation and Biomimetic Synthesis of (+/-)-Cochlactone A with Anti-Inflammatory Activity.JOURNAL OF ORGANIC CHEMISTRY,83(10),5516-5522.
MLA Peng, Xing-Rong,et al."Structural Elucidation and Biomimetic Synthesis of (+/-)-Cochlactone A with Anti-Inflammatory Activity".JOURNAL OF ORGANIC CHEMISTRY 83.10(2018):5516-5522.
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