Aspertaichunol A, an Immunomodulatory Polyketide with an Uncommon Scaffold from the Insect-Derived Endophytic <em>Aspergillus taichungensis</em> SMU01

Org Lett. 2022 Sep 25. doi: 10.1021/acs.orglett.2c02978. Online ahead of print.


Aspertaichunol A (1), a polyketide with a novel scaffold, was isolated from the medicinal insect (Periplaneta americana)-derived endophytic Aspergillus taichungensis SMU01. Its structure was assigned on the basis of spectroscopic data and quantum chemical computational methods. Notably, 1 possesses an uncommon tricyclo[,6]decane motif and an unusual bridgehead double bond (anti-Bredt system). A plausible biosynthetic pathway, involving a key intramolecular [2+2] cycloaddition and a reductive cyclization, is postulated. Finally, the immunomodulatory activity of 1 at 20 nM was evaluated by promoting Th9 cell differentiation from naive CD4+CD62L+ T cells.

PMID:36153741 | DOI:10.1021/acs.orglett.2c02978

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