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从NRRL 35600中分离出一种新的吲哚生物碱——Amoenamide B:生物合成意义及Speramide B结构的修正

Isolation of a new indoxyl alkaloid, Amoenamide B, from NRRL 35600: biosynthetic implications and correction of the structure of Speramide B.

作者信息

Kai Aika, Kato Hikaru, Sherman David H, Williams Robert M, Tsukamoto Sachiko

机构信息

Graduate School of Pharmaceutical Sciences, Kumamoto University, Oe-honmachi 5-1, Kumamoto 862-0973, Kumamoto, Japan.

Life Sciences Institute, University of Michigan, Ann Arbor, Michigan 48109, United States.

出版信息

Tetrahedron Lett. 2018 Nov 28;50(48):4236-4240. doi: 10.1016/j.tetlet.2018.10.034. Epub 2018 Oct 20.

DOI:10.1016/j.tetlet.2018.10.034
PMID:30765898
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6370310/
Abstract

A new prenylated indoxyl alkaloid, Amoenamide B (), was isolated from NRRL 35600 along with Asperochramide A (). Although many prenylated oxyindole alkaloids, containing bicyclo[2.2.2]diazaoctane cores, have been isolated from the fungus of the genera and to date, is the fourth compound with the indoxyl unit containing the cores. During the structure elucidation of , we found that the planar structure matched to that of Speramide A (), isolated from KM007, but the reported structure of was incorrect and turned out to be that of Taichunamide H (), recently isolated from HDN11-84.

摘要

从NRRL 35600中分离出一种新的异戊烯基吲哚生物碱,Amoenamide B(),同时还分离出了Asperochramide A()。尽管迄今为止已从多个属的真菌中分离出许多含有双环[2.2.2]二氮杂辛烷核心的异戊烯基氧化吲哚生物碱,但 是第四个含有该核心的吲哚单元的化合物。在对 的结构解析过程中,我们发现其平面结构与从KM007中分离出的Speramide A()的平面结构相匹配,但报道的 的结构是错误的,结果证明它是最近从HDN11-84中分离出的Taichunamide H()的结构。

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本文引用的文献

1
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Tetrahedron Lett. 2017 Jul 19;58(29):2797-2800. doi: 10.1016/j.tetlet.2017.05.057. Epub 2017 May 18.
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Three New Indole Diketopiperazine Alkaloids from Aspergillus ochraceus.来自赭曲霉的三种新吲哚二酮哌嗪生物碱。
Chem Biodivers. 2018 Apr;15(4):e1700550. doi: 10.1002/cbdv.201700550. Epub 2018 Apr 17.
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Determination of Taichunamide H and Structural Revision of Taichunamide A.太春花酰胺 H 的测定及太春花酰胺 A 的结构修订。
Org Lett. 2018 Feb 16;20(4):1138-1141. doi: 10.1021/acs.orglett.8b00061. Epub 2018 Feb 5.
4
Taichunamides: Prenylated Indole Alkaloids from Aspergillus taichungensis (IBT 19404).台中酰胺类化合物:来自台中曲霉(IBT 19404)的异戊烯基化吲哚生物碱
Angew Chem Int Ed Engl. 2016 Jan 18;55(3):1128-32. doi: 10.1002/anie.201509462. Epub 2015 Dec 8.
5
Bioconversion of 6--Notoamide T Produces Metabolites of Unprecedented Structures in a Marine-derived sp.6-去甲酰胺T在一种海洋来源的菌种中的生物转化产生了结构前所未有的代谢产物
Tetrahedron Lett. 2015 Jan 1;56(1):247-251. doi: 10.1016/j.tetlet.2014.11.083.
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