Isolation of a new indoxyl alkaloid, Amoenamide B, from Aspergillus amoenus NRRL 35600: Biosynthetic implications and correction of the structure of Speramide B

TETRAHEDRON LETTERS

卷:59

Article

Kai, Aika¹  Kato, Hikaru¹  Sherman, David H.^2,3  Williams, Robert M.^4,5  Tsukamoto, Sachiko¹ 

[1] Kumamoto Univ, Grad Sch Pharmaceut Sci, Oe Honmachi 5-1, Kumamoto, Kumamoto 8620973, Japan

[2] Univ Michigan, Life Sci Inst, Ann Arbor, MI 48109 USA

[3] Univ Michigan, Dept Microbiol & Immunol, Dept Chem, Dept Med Chem, Ann Arbor, MI 48109 USA

[4] Colorado State Univ, Dept Chem, 1301 Ctr Ave, Ft Collins, CO 80523 USA

[5] Univ Colorado, Canc Ctr, Aurora, CO 80045 USA

关键词: Indoxyl alkaloid;    Aspergillus;    Fungus;   

DOI  :  10.1016/j.tetlet.2018.10.034

来源: Elsevier

【 摘 要 】

A new prenylated indoxyl alkaloid, Amoenamide B (1), was isolated from Aspergillus amoenus NRRL 35600 along with Asperochramide A (2). Although many prenylated oxindole alkaloids, containing bicyclo[2.2.2]diazaoctane cores, have been isolated from the fungus of the genera Aspergillus and Penicillium to date, 1 is the fourth compound with the indoxyl unit containing the cores. During the structure elucidation of 1, we found that the planar structure matched to that of Speramide A (3), isolated from A. ochraceus KM007, but the reported structure of 3 was incorrect and turned out to be that of Taichunamide H (4), recently isolated from A. versicolor HDN11-84. (C) 2018 Elsevier Ltd. All rights reserved.

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