Asperosin A, a [4+2] Diets-Alder cyctoaddition polyketide dimer from Aspergillus rugulosa with immunosuppressive activity

A novel homologous polyketide dimer, asperosin A (1), constructed with a unique hetero-bicycle 6/5 ring system featuring four continuous quaternary carbons, was isolated from a solid culture of the fungus Aspergillus rugulosa. The structure of 1 was elucidated by extensive 400 MHz and 600 MHz nuclea...

Full description

Saved in:
Bibliographic Details
Published inORGANIC CHEMISTRY FRONTIERS Vol. 9; no. 9; pp. 2477 - 2485
Main Authors Qiao, Yuben, Tan, Xiaosheng, Xu, Qianqian, Zhang, Zijun, Xu, Qiaoxin, Tao, Li, Liu, Junjun, Zhu, Hucheng, Chen, Chunmei, Ye, Ying, Lu, Yuanyuan, Chen, Gang, Qi, Changxing, Zhang, Yonghui
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 03.05.2022
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ASPERTETRONIN
ACID
Online AccessGet more information

Cover

More Information
Summary:A novel homologous polyketide dimer, asperosin A (1), constructed with a unique hetero-bicycle 6/5 ring system featuring four continuous quaternary carbons, was isolated from a solid culture of the fungus Aspergillus rugulosa. The structure of 1 was elucidated by extensive 400 MHz and 600 MHz nuclear magnetic resonance (NMR) spectroscopy analysis, electronic circular dichroism (ECD) calculations, DP4(+) probability analysis, and a detailed discussion of its biosynthetic origin. Biogenetically, compound 1 was constructed from two identical original polyketides via the intermolecular [4 + 2] Diels-Alder cyclo-addition reaction. It is notable that compound 1 displayed remarkable immunosuppressive activity in murine splenocytes and human T cells stimulated by anti-CD3/anti-CD28 monoclonal antibodies.
ISSN:2052-4129
DOI:10.1039/d1qo01767e