Astellolides R-W, Drimane-Type Sesquiterpenoids from an Aspergillus parasiticus Strain Associated with an Isopod

被引:7
|
作者
Dai, Guangzhi [1 ]
Sun, Jianpeng [1 ]
Peng, Xiaoping [2 ]
Shen, Qiyao [1 ]
Wu, Changzheng [1 ]
Sun, Zhiheng [1 ]
Sui, Haiyan [1 ]
Ren, Xiangmei [1 ]
Zhang, Youming [1 ]
Bian, Xiaoying [1 ]
机构
[1] Shandong Univ, Helmholtz Int Lab Antiinfect, Helmholtz Inst Biotechnol, State Key Lab Microbial Technol, Qingdao 266237, Peoples R China
[2] Qingdao Univ, Sch Pharm, Dept Nat Med Chem & Pharmacognosy, Qingdao 266071, Peoples R China
来源
JOURNAL OF NATURAL PRODUCTS | 2023年 / 86卷 / 07期
基金
国家重点研发计划; 中国国家自然科学基金;
关键词
NITROBENZOYL SESQUITERPENOIDS; FUNGUS; PERICONIANONE; SKELETON;
D O I
10.1021/acs.jnatprod.3c00215
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Sesquiterpenoids with a cage-like multiring frame arerarely foundin nature. Mining of the isopod-derived fungus Aspergillusparasiticus SDU001 by the one strain-many compounds(OSMAC) strategy unexpectedly led to the discovery of fungal drimane-typesesquiterpenoids astellolide R (1), featuring an unusualcage-like 6/6/5/6/5 pentacyclic ring system, astellolide S (2), possessing a rare nicotinic acid building block, and astellolidesT-W (3-6). Their structureswere comprehensively assigned by spectroscopic data analysis, single-crystalX-ray diffraction, and electronic circular dichroism calculations.Furthermore, compounds 3 and 5 exhibitedanti-inflammatory activity by inhibiting the lipopolyssacharide-inducedNO production in RAW264.7 macrophages with IC50 valuesof 6.1 & PLUSMN; 0.8 and 6.8 & PLUSMN; 0.8 & mu;M, respectively. A putativebiosynthetic pathway for 1 is proposed. Our results enlargethe chemical space of the drimane-type sesquiterpenoids generatedfrom endophytic fungi.
引用
收藏
页码:1746 / 1753
页数:8
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