Structural and Stereochemical Diversity in Prenylated Indole Alkaloids Containing the Bicyclo[2.2.2]diazaoctane Ring System from Marine and Terrestrial Fungi

Overview

Journal Nat Prod Rep

Publisher Royal Society of Chemistry

Date 2018 Apr 11

PMID 29632911

Citations 26

Authors

Kimberly R Klas

Hikaru Kato

Jens C Frisvad

Fengan Yu

Sean A Newmister

Amy E Fraley

David H Sherman

Sachiko Tsukamoto

Robert M Williams

Affiliations

Soon will be listed here.

Abstract

Covering: up to February 2017 Various fungi of the genera Aspergillus, Penicillium, and Malbranchea produce prenylated indole alkaloids possessing a bicyclo[2.2.2]diazaoctane ring system. After the discovery of distinct enantiomers of the natural alkaloids stephacidin A and notoamide B, from A. protuberus MF297-2 and A. amoenus NRRL 35660, another fungi, A. taichungensis, was found to produce their diastereomers, 6-epi-stephacidin A and versicolamide B, as major metabolites. Distinct enantiomers of stephacidin A and 6-epi-stephacidin A may be derived from a common precursor, notoamide S, by enzymes that form a bicyclo[2.2.2]diazaoctane core via a putative intramolecular hetero-Diels-Alder cycloaddition. This review provides our current understanding of the structural and stereochemical homologies and disparities of these alkaloids. Through the deployment of biomimetic syntheses, whole-genome sequencing, and biochemical studies, a unified biogenesis of both the dioxopiperazine and the monooxopiperazine families of prenylated indole alkaloids constituted of bicyclo[2.2.2]diazaoctane ring systems is presented.

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