Phaeosphspirone (1/1 '), a pair of unique polyketide enantiomers with an unusual 6/5/5/6 tetracyclic ring from the desert plant endophytic fungus Phaeosphaeriaceae sp.

Xu, Zhen-Lu ¹Yan, Dao-Jiang ²Tan, Xiang-Mei ¹Yu, Meng ¹Niu, Shu-Bin ³Sun, Bing-Da ⁴Ding, Cai-Feng ⁴Zhang, Yong-Gang ⁵Ding, Gang¹

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作者信息

1. Peking Union Med Coll & Chinese Acad Med Sci
2. Chinese Acad Med Sci & Peking Union Med Coll
3. Beijing City Univ
4. Chinese Acad Sci
5. Qilu Univ Technol
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Abstract

Phaeosphspirone, an undescribed polyketide with a unique 6/5/5/6-fused tetracyclic system, and two known analogues, herbarin and O-methylherbarin, were purified from the endophytic fungus Phaeosphaeriaceae sp. isolated from the desert plant Bassia dasyphylla. The connectivity and relative configuration of phaeosphspirone was elucidated by comprehensive HR-ESI-MS and NMR analysis together with a computer-assisted structure elucidation (CASE) method. A pair of enantiomers existing in phaeosphspirone were separated by HPLC chromatography after reacting with chiral reagents, from which the absolute configuration of phaeosphspirone was simultaneously determined based on Mosher's rule. This tandem strategy provides a useful approach for the separation and stereochemical determination of enantiomers possessing secondary hydroxyl groups. The structural feature of phaeosphspirone, herbarin and O-methylherbarin together with gene cluster analysis suggested their polyketide biosynthetic origin. Herbarin and O-methylherbarin exhibited moderate cytotoxicity against three cancer cell lines.

Key words

Phaeosphspirone/Phaeosphaeriaceae/Absolute configurations/Biosynthetic pathway/Cytotoxicity/ASSISTED STRUCTURE ELUCIDATION/BIOSYNTHESIS/REVISION

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出版年

2022

Phytochemistry

CCR

ISSN：0031-9422

被引量2

参考文献量28

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