诺托酰胺的生物合成研究：脱氧短裸甲藻毒素E和6-羟基脱氧短裸甲藻毒素E中异戊二烯单元的频哪醇型重排。
Study on the biosynthesis of the notoamides: Pinacol-type rearrangement of the isoprenyl unit in deoxybrevianamide E and 6-hydroxydeoxybrevianamide E.
作者信息
Kato Hikaru, Nakamura Yuichi, Finefield Jennifer M, Umaoka Hideharu, Nakahara Takashi, Williams Robert M, Tsukamoto Sachiko
机构信息
Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Kumamoto, 862-0973, Japan.
出版信息
Tetrahedron Lett. 2011 Dec 21;52(51):6923-6926. doi: 10.1016/j.tetlet.2011.10.065.
Abstract
Two reverse-prenylated indole alkaloids, deoxybrevianamide E and 6-hydroxydeoxybrevianamide E, are proposed as biosynthetic precursors for advanced metabolites isolated from the marine-derived Aspergillus sp. In order to uncover the role of the alkaloids in the biosynthetic pathway, the feeding experiments of the (13)C-[(15)N]-labeled deoxybrevianamide E and 6-hydroxydeoxybrevianamide E were performed to afford the metabolites, which were produced by oxidation and successive pinacol-type rearrangement of the isoprenyl units.
摘要
两种反式异戊烯基化吲哚生物碱，脱氧短裸壳菌素E和6-羟基脱氧短裸壳菌素E，被认为是从海洋来源的曲霉属真菌中分离出的高级代谢产物的生物合成前体。为了揭示这些生物碱在生物合成途径中的作用，进行了(13)C-[(15)N]标记的脱氧短裸壳菌素E和6-羟基脱氧短裸壳菌素E的饲喂实验，以得到由异戊烯基单元氧化和连续频哪醇型重排产生的代谢产物。
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本文引用的文献
1
Studies on the biosynthesis of the notoamides: synthesis of an isotopomer of 6-hydroxydeoxybrevianamide E and biosynthetic incorporation into notoamide J.关于诺托酰胺生物合成的研究：6-羟基去氧布雷文酰胺 E 的同位素类似物的合成及生物合成掺入到诺托酰胺 J 中。
J Org Chem. 2011 Aug 5;76(15):5954-8. doi: 10.1021/jo200218a. Epub 2011 Jun 28.
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Notoamide O, a structurally unprecedented prenylated indole alkaloid, and notoamides P-R from a marine-derived fungus, Aspergillus sp.来自海洋来源真菌 Aspergillus sp. 的 Notoamide O，一种结构上前所未有的prenylated 吲哚生物碱，以及 notoamides P-R
J Nat Prod. 2010 Aug 27;73(8):1438-40. doi: 10.1021/np1002498.
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Asymmetric total syntheses of (+)- and (-)-versicolamide B and biosynthetic implications.（+）-和（-）-变色胺 B 的不对称全合成及生物合成意义。
Nat Chem. 2009 Apr;1(1):63-8. doi: 10.1038/nchem.110.
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Isolation of notoamide E, a key precursor in the biosynthesis of prenylated indole alkaloids in a marine-derived fungus, Aspergillus sp.从海洋来源的真菌曲霉属（Aspergillus sp.）中分离出诺托酰胺E，它是异戊烯基化吲哚生物碱生物合成中的关键前体。
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Org Lett. 2009 Mar 19;11(6):1297-300. doi: 10.1021/ol900071c.
6
Notoamides F-K, prenylated indole alkaloids isolated from a marine-derived Aspergillus sp.诺托酰胺F-K，从海洋来源的曲霉属真菌中分离得到的异戊烯基化吲哚生物碱
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Nat Prod Res. 2008 May 20;22(8):709-14. doi: 10.1080/14786410802012361.
8
Isolation, structure elucidation, and biomimetic total synthesis of versicolamide B, and the isolation of antipodal (-)-stephacidin A and (+)-notoamide B from Aspergillus versicolor NRRL 35600.杂色曲菌素B的分离、结构解析及仿生全合成，以及从杂色曲霉NRRL 35600中分离出对映体（-）-斯蒂芬菌素A和（+）-诺托酰胺B。
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