Isolation of Notoamide S and Enantiomeric 6-epi-Stephacidin A from the Fungus Aspergillus amoenus: Biogenetic Implications

Hikaru Kato; Takashi Nakahara; Kayo Sugimoto; Kanae Matsuo; Ippei Kagiyama; Jens Christian Frisvad; David H. Sherman; Robert M. Williams; Sachiko Tsukamoto

doi:10.1021/ol5037198

Isolation of Notoamide S and Enantiomeric 6-epi-Stephacidin A from the Fungus Aspergillus amoenus: Biogenetic Implications

Hikaru Kato, Takashi Nakahara, Kayo Sugimoto, Kanae Matsuo, Ippei Kagiyama, Jens Christian Frisvad, David H. Sherman, Robert M. Williams, Sachiko Tsukamoto

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

Notoamide S has been hypothesized to be a key biosynthetic intermediate for characteristic metabolites stephacidin A, notoamide B, and versicolamide B in Aspergillus sp. but has not yet been isolated. The isolation of notoamide S and an enantiomeric mixture of 6-epi-stephacidin A enriched with the (-)-isomer from Aspergillus amoenus is reported. The presence of (+)-versicolamide B suggests that the fungus possesses only the oxidase, which converts (+)-6-epi-stephacidin A into (+)-Versicolamide B, but not for (-)-6-epi-Stephacidin A.

Original language	English
Journal	Organic Letters
Volume	17
Issue number	3
Pages (from-to)	700-703
Number of pages	4
ISSN	1523-7060
DOIs	https://doi.org/10.1021/ol5037198
Publication status	Published - 2015

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title = "Isolation of Notoamide S and Enantiomeric 6-epi-Stephacidin A from the Fungus Aspergillus amoenus: Biogenetic Implications",

abstract = "Notoamide S has been hypothesized to be a key biosynthetic intermediate for characteristic metabolites stephacidin A, notoamide B, and versicolamide B in Aspergillus sp. but has not yet been isolated. The isolation of notoamide S and an enantiomeric mixture of 6-epi-stephacidin A enriched with the (-)-isomer from Aspergillus amoenus is reported. The presence of (+)-versicolamide B suggests that the fungus possesses only the oxidase, which converts (+)-6-epi-stephacidin A into (+)-Versicolamide B, but not for (-)-6-epi-Stephacidin A.",

author = "Hikaru Kato and Takashi Nakahara and Kayo Sugimoto and Kanae Matsuo and Ippei Kagiyama and Frisvad, {Jens Christian} and Sherman, {David H.} and Williams, {Robert M.} and Sachiko Tsukamoto",

year = "2015",

doi = "10.1021/ol5037198",

language = "English",

volume = "17",

pages = "700--703",

journal = "Organic Letters",

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T1 - Isolation of Notoamide S and Enantiomeric 6-epi-Stephacidin A from the Fungus Aspergillus amoenus: Biogenetic Implications

AU - Kato, Hikaru

AU - Nakahara, Takashi

AU - Sugimoto, Kayo

AU - Matsuo, Kanae

AU - Kagiyama, Ippei

AU - Frisvad, Jens Christian

AU - Sherman, David H.

AU - Williams, Robert M.

AU - Tsukamoto, Sachiko

PY - 2015

Y1 - 2015

N2 - Notoamide S has been hypothesized to be a key biosynthetic intermediate for characteristic metabolites stephacidin A, notoamide B, and versicolamide B in Aspergillus sp. but has not yet been isolated. The isolation of notoamide S and an enantiomeric mixture of 6-epi-stephacidin A enriched with the (-)-isomer from Aspergillus amoenus is reported. The presence of (+)-versicolamide B suggests that the fungus possesses only the oxidase, which converts (+)-6-epi-stephacidin A into (+)-Versicolamide B, but not for (-)-6-epi-Stephacidin A.

AB - Notoamide S has been hypothesized to be a key biosynthetic intermediate for characteristic metabolites stephacidin A, notoamide B, and versicolamide B in Aspergillus sp. but has not yet been isolated. The isolation of notoamide S and an enantiomeric mixture of 6-epi-stephacidin A enriched with the (-)-isomer from Aspergillus amoenus is reported. The presence of (+)-versicolamide B suggests that the fungus possesses only the oxidase, which converts (+)-6-epi-stephacidin A into (+)-Versicolamide B, but not for (-)-6-epi-Stephacidin A.

U2 - 10.1021/ol5037198

DO - 10.1021/ol5037198

M3 - Journal article

C2 - 25615822

SN - 1523-7060

VL - 17

SP - 700

EP - 703

JO - Organic Letters

JF - Organic Letters

IS - 3

ER -

Isolation of Notoamide S and Enantiomeric 6-epi-Stephacidin A from the Fungus Aspergillus amoenus: Biogenetic Implications

Abstract

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