Aspersecosteroids A and B, Two 11(9 → 10)-abeo-5,10-Secosteroids with a Dioxatetraheterocyclic Ring System from Aspergillus flocculosus 16D-1

被引：26

作者：

Gu, Bin-Bin ^{[1
]}

Wu, Wei ^{[1
]}

Jiao, Fu-Rong ^{[1
]}

Jiao, Wei-hua ^{[1
]}

Li, Lei ^{[1
]}

Sun, Fan ^{[1
]}

Wang, Shu-Ping ^{[1
]}

Yang, Fan ^{[1
]}

Lin, Hou-Wen ^{[1
]}

机构：

[1] Shanghai Jiao Tong Univ, Ren Ji Hosp, State Key Lab Oncogenes & Related Genes, Res Ctr Marine Drugs,Dept Pharm,Sch Med, Shanghai 200127, Peoples R China

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 24期

基金：

国家高技术研究发展计划(863计划);

关键词：

FUNGUS; DERIVATIVES; PREDICTION; SKELETONS; STEROIDS; H-1-NMR; ACID;

D O I：

10.1021/acs.orglett.8b03530

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two 11(9 -> 10)-abeo-5,10-secosteroids possessing an unprecedented dioxatetraheterocyclic ring system, aspersecosteroids A (1) and B (2), and a new ergosteroid, asperflosterol (3), were isolated from the sponge-derived fungus Aspergillus flocculosus 16D-1. Their structures were determined by spectroscopic analysis, X-ray diffraction, and computational methods. Compounds 1-3 demonstrated inhibitory effects on key pro-inflammatory cytokine production in THP-1 cells. A biogenetic pathway with oxidative cleavage, Wagner-Meerwein rearrangement, and sequential acetalization as key steps is proposed for 1 and 2.

引用

页码：7957 / 7960

页数：4

共 2 条

[1] Asperflotone, an 8(14→15)-abeo-Ergostane from the Sponge-Derived Fungus Aspergillus flocculosus 16D-1
Gu, Bin-Bin
Wu, Wei
Jiao, Fu-Rong
Jiao, Wei-hua
Li, Lei
Sun, Fan
Wang, Shu-Ping
Yang, Fan
Lin, Hou-Wen
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (01) : 300 - 306
[2] Asperfloketals A and B, the First Two Ergostanes with Rearranged A and D Rings: From the Sponge-Associated Aspergillus flocculosus 16D-1
Jiao, Fu-Rong
Gu, Bin-Bin
Zhu, Hong-Rui
Zhang, Yun
Liu, Ke-Chun
Zhang, Wei
Han, Hua
Xu, Shi-Hai
Lin, Hou-Wen
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (16) : 10954 - 10961

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