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Aspertaichunol A, an Immunomodulatory Polyketide with an Uncommon Scaffold from the Insect-Derived Endophytic Aspergillus taichungensis SMU01.

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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… Click to show full abstract

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[6.2.0.02,6]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.

Keywords: endophytic aspergillus; taichungensis smu01; derived endophytic; polyketide; aspergillus taichungensis

Journal Title: Organic letters
Year Published: 2022

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