Acautalides A–C, Neuroprotective Diels–Alder Adducts from Solid-State Cultivated <i>Acaulium</i> sp. H-JQSF
Zhi Wu Tong, Xia Hong Xie, Ting Ting Wang, Ming Lu, Rui Jiao, Hui Ming Ge, Gang Hu, Ren Xiang Tan
Abstract
The solid-state cultivation of Acaulium sp. H-JQSF isolated from Armadillidium vulgare produces acautalides A–C (1–3) 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 1–3 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.