1. Acautalides A–C, Neuroprotective Diels–Alder Adducts from Solid-State Cultivated Acaulium sp. H-JQSF
- Author
-
Ren-Xiang Tan, Hui Ming Ge, Rui Hua Jiao, Ming Lu, Gang Hu, Ting Ting Wang, Xia Hong Xie, and Zhi Wu Tong
- Subjects
Armadillidium vulgare ,Chemical transformation ,biology ,010405 organic chemistry ,Stereochemistry ,Organic Chemistry ,010402 general chemistry ,biology.organism_classification ,Mass spectrometry ,01 natural sciences ,Biochemistry ,Neuroprotection ,0104 chemical sciences ,Adduct ,chemistry.chemical_compound ,chemistry ,Intramolecular force ,Diels alder ,Glycerol ,Physical and Theoretical Chemistry - 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.
- Published
- 2021