B-norsteroids from Hymenoscyphus pseudoalbidus

被引：22

作者：

Andersson, Pierre F. ^{[1
]}

Bengtsson, Stina ^{[2
]}

Stenlid, Jan ^{[2
]}

Broberg, Anders ^{[1
]}

机构：

[1] Swedish Univ Agr Sci, Dept Chem, Uppsala BioCtr, SE-75007 Uppsala, Sweden

[2] Swedish Univ Agr Sci, Dept Forest Mycol & Plant Pathol, Uppsala BioCtr, SE-75007 Uppsala, Sweden

来源：

MOLECULES | 2012年 / 17卷 / 07期

基金：

瑞典研究理事会;

关键词：

Hymenoscyphus pseudoalbidus; Chalara fraxinea; B-norsteroids; secondary metabolites; structure elucidation; CHALARA-FRAXINEA; HYDROGEN-BOND; IDENTIFICATION; VIRIDIOL; SPONGE; BIOSYNTHESIS; METABOLITES; EXCELSIOR; STEROIDS; FUNGUS;

D O I：

10.3390/molecules17077769

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Two viridin-related B-norsteroids, B-norviridiol lactone (1) and B-norviridin enol (2), both possessing distinct unprecedented carbon skeletons, were isolated from a liquid culture of the ash dieback-causing fungus Hymenoscyphus pseudoalbidus. Compound 2 was found to degrade to a third B-norsteroidal compound, 1 beta-hydroxy-2 alpha-hydro-asterogynin A (3), which was later detected in the original culture. The proposed structure of 1 is, regarding connectivity, identical to the original erroneous structure for TAEMC161, which was later reassigned as viridiol. Compound 2 showed an unprecedented H-1-C-13 HMBC correlation through an intramolecular hydrogen bond. The five-membered B-ring of compounds 1-3 was proposed to be formed by a benzilic acid rearrangement. The known compound asterogynin A was found to be formed from 3 by a beta-elimination of water. All compounds were characterized by NMR spectroscopy, LC-HRMS and polarimetry.

引用

页码：7769 / 7781

页数：13

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