Phomanolides A and B from the Fungus Phoma sp.: Meroterpenoids Derived from a Putative Tropolonic Sesquiterpene via Hetero-Diels− Alder Reactions

By Jinyu Zhang, Ling Liu, Bo Wang, Yang Zhang, Lili Wang, Xingzhong Liu, Yongsheng Che

July 28, 2017

  • Year

  • Technique

  • Industry

Title

Phomanolides A and B from the Fungus Phoma sp.: Meroterpenoids Derived from a Putative Tropolonic Sesquiterpene via Hetero-Diels− Alder Reactions

Author

Jinyu Zhang, Ling Liu, Bo Wang, Yang Zhang, Lili Wang, Xingzhong Liu, Yongsheng Che

Year

2015

Journal

Journal of Natural Products

Abstract

Phomanolides A (1) and B (2), unique meroterpenoids with new pentacyclic and tetracyclic skeletons, respectively, and phomanoxide (3), the double-epoxidation product of a putative biosynthetic precursor of 1 and 2, were isolated from the solid substrate fermentation cultures of the fungus Phoma sp., along with the known compound eupenifeldin (4). The structures of 1–3were elucidated based on NMR spectroscopic data and electronic circular dichroism calculations and further secured by X-ray crystallography. Biogenetically, compounds 1 and 2 could be derived from a hypothetical monotropolonic sesquiterpene intermediate via hetero-Diels–Alder reactions. Compound 4 showed potent antiproliferative effects against three human glioma cell lines, with IC50 values of 0.08–0.13 μM.

Full Article

http://pubs.acs.org/doi/abs/10.1021/acs.jnatprod.5b00969

Instrument

J-815

Keywords

Circular dichroism, Absolute configuration