JBIR-56 and JBIR-57, 2(1 H)-pyrazinones from a marine sponge-derived streptomyces sp. SpD081030SC-03

Keiichiro Motohashi; Kennichi Inaba; Shinichiro Fuse; Takayuki Doi; Miho Izumikawa; Shams Tabrez Khan; Motoki Takagi; Takashi Takahashi; Kazuo Shin-Ya

doi:10.1021/np200386c

JBIR-56 and JBIR-57, 2(1 H)-pyrazinones from a marine sponge-derived streptomyces sp. SpD081030SC-03

Keiichiro Motohashi, Kennichi Inaba, Shinichiro Fuse, Takayuki Doi, Miho Izumikawa, Shams Tabrez Khan, Motoki Takagi, Takashi Takahashi, Kazuo Shin-Ya

PHA - Molecular Pharmaceutical Science

Research output: Contribution to journal › Article › peer-review

32 Citations (Scopus)

Abstract

Strain SpD081030SC-03, representing a novel species of Streptomyces, was isolated from a marine sponge. Two 3,5,6-trisubstituted 2(1H)-pyrazinones, JBIR-56 (1) and JBIR-57 (2), were isolated from a culture of SpD081030SC-03. The planar structures of 1 and 2 were assigned on the basis of extensive NMR and MS analyses. In addition, analyses of the methylated derivative of 1 confirmed a 3,5,6-trisubstituted 2(1H)-pyrazinone moiety. The absolute configurations of the amino acid residues were determined by application of Marfey's method. Because 1 did not appear to comprise the normal connection of amino acid units, we confirmed its structure by the total synthesis of 1. Biosynthetically, 1 consists of a unique skeleton connected to the peptide chain at C-5 of the pyrazinone ring.

Original language	English
Pages (from-to)	1630-1635
Number of pages	6
Journal	Journal of Natural Products
Volume	74
Issue number	7
DOIs	https://doi.org/10.1021/np200386c
Publication status	Published - 2011 Jul 22

ASJC Scopus subject areas

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

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This output contributes to the following UN Sustainable Development Goals (SDGs)

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JBIR-56 and JBIR-57, 2(1 H)-pyrazinones from a marine sponge-derived streptomyces sp. SpD081030SC-03. / Motohashi, Keiichiro; Inaba, Kennichi; Fuse, Shinichiro; Doi, Takayuki; Izumikawa, Miho; Khan, Shams Tabrez; Takagi, Motoki; Takahashi, Takashi; Shin-Ya, Kazuo.

In: Journal of Natural Products, Vol. 74, No. 7, 22.07.2011, p. 1630-1635.

Research output: Contribution to journal › Article › peer-review

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title = "JBIR-56 and JBIR-57, 2(1 H)-pyrazinones from a marine sponge-derived streptomyces sp. SpD081030SC-03",

abstract = "Strain SpD081030SC-03, representing a novel species of Streptomyces, was isolated from a marine sponge. Two 3,5,6-trisubstituted 2(1H)-pyrazinones, JBIR-56 (1) and JBIR-57 (2), were isolated from a culture of SpD081030SC-03. The planar structures of 1 and 2 were assigned on the basis of extensive NMR and MS analyses. In addition, analyses of the methylated derivative of 1 confirmed a 3,5,6-trisubstituted 2(1H)-pyrazinone moiety. The absolute configurations of the amino acid residues were determined by application of Marfey's method. Because 1 did not appear to comprise the normal connection of amino acid units, we confirmed its structure by the total synthesis of 1. Biosynthetically, 1 consists of a unique skeleton connected to the peptide chain at C-5 of the pyrazinone ring.",

author = "Keiichiro Motohashi and Kennichi Inaba and Shinichiro Fuse and Takayuki Doi and Miho Izumikawa and Khan, {Shams Tabrez} and Motoki Takagi and Takashi Takahashi and Kazuo Shin-Ya",

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doi = "10.1021/np200386c",

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AU - Motohashi, Keiichiro

AU - Inaba, Kennichi

AU - Fuse, Shinichiro

AU - Doi, Takayuki

AU - Izumikawa, Miho

AU - Khan, Shams Tabrez

AU - Takagi, Motoki

AU - Takahashi, Takashi

AU - Shin-Ya, Kazuo

PY - 2011/7/22

Y1 - 2011/7/22

N2 - Strain SpD081030SC-03, representing a novel species of Streptomyces, was isolated from a marine sponge. Two 3,5,6-trisubstituted 2(1H)-pyrazinones, JBIR-56 (1) and JBIR-57 (2), were isolated from a culture of SpD081030SC-03. The planar structures of 1 and 2 were assigned on the basis of extensive NMR and MS analyses. In addition, analyses of the methylated derivative of 1 confirmed a 3,5,6-trisubstituted 2(1H)-pyrazinone moiety. The absolute configurations of the amino acid residues were determined by application of Marfey's method. Because 1 did not appear to comprise the normal connection of amino acid units, we confirmed its structure by the total synthesis of 1. Biosynthetically, 1 consists of a unique skeleton connected to the peptide chain at C-5 of the pyrazinone ring.

AB - Strain SpD081030SC-03, representing a novel species of Streptomyces, was isolated from a marine sponge. Two 3,5,6-trisubstituted 2(1H)-pyrazinones, JBIR-56 (1) and JBIR-57 (2), were isolated from a culture of SpD081030SC-03. The planar structures of 1 and 2 were assigned on the basis of extensive NMR and MS analyses. In addition, analyses of the methylated derivative of 1 confirmed a 3,5,6-trisubstituted 2(1H)-pyrazinone moiety. The absolute configurations of the amino acid residues were determined by application of Marfey's method. Because 1 did not appear to comprise the normal connection of amino acid units, we confirmed its structure by the total synthesis of 1. Biosynthetically, 1 consists of a unique skeleton connected to the peptide chain at C-5 of the pyrazinone ring.

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JBIR-56 and JBIR-57, 2(1 H)-pyrazinones from a marine sponge-derived streptomyces sp. SpD081030SC-03

Abstract

ASJC Scopus subject areas

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