Acautalides A-C, Neuroprotective Diels-Alder Adducts from Solid-State Cultivated sp. H-JQSF.

Org Lett

State Key Laboratory of Pharmaceutical Biotechnology, Institute of Functional Biomolecules, Nanjing University, Nanjing, Jiangsu 210023, People's Republic of China.

Published: July 2021

The solid-state cultivation of sp. H-JQSF isolated from produces acautalides A-C (-) as skeletally unprecedented Diels-Alder adducts of a 14-membered macrodiolide to an octadeca-9,11,13-trienoic acid. The acautalide structures, along with the intramolecular transesterifications of 1-acylglycerols, were elucidated by mass spectrometry, nuclear magnetic resonance, chemical transformation, and single-crystal X-ray diffraction. Compounds - were found to be neuroprotective with antiparkinsonic potential in the 1-methyl-4-phenylpyridinium-challenged nematode model, with the magnitude impacted by the glycerol esterification.

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http://dx.doi.org/10.1021/acs.orglett.1c02089DOI Listing

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