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Asperorydines A–M: Prenylated Tryptophan-Derived Alkaloids with Neurotrophic Effects from Aspergillus oryzae

Author:
Liu, Li, Bao, Li, Wang, Long, Ma, Ke, Han, Junjie, Yang, Yanlong, Liu, Ruixing, Ren, Jinwei, Yin, Wenbing, Wang, Wenzhao, Liu, Hongwei
Source:
Journal of organic chemistry 2018 v.83 no.2 pp. 812-822
ISSN:
1520-6904
Subject:
Aspergillus oryzae, chemical reactions, chemical structure, circular dichroism spectroscopy, fungi, neurites, organic chemistry, quinoline alkaloids
Abstract:
As part of our program to discover new bioactive agents from fungi, 13 new alkaloids accompanying 13 known related alkaloids were isolated from a wild strain of Aspergillus oryzae L1020. Compounds 1 and 2 have unprecedented 6/6/5/7/5 and 6/6/6/5/5 chemical skeletons, representing new members of quinoline alkaloids. Compound 3 is a new macrolactam with an unusual 6/5/6/8 ring system. Compounds 4–13 are new α-cyclopiazonic acid-related alkaloids. The absolute configurations of 1–4, 8, and 9 were assigned by electronic circular dichroism calculations. Compounds 2, 5, 6, 11, 14, 22, and 26 exhibit pronounced neurite outgrowth-promoting effects on PC12 cells in the range of 25–100 μM.
Agid:
6046754