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

30 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

UN SDGs

This output contributes to the following Sustainable Development Goal(s)

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10.1021/np200386c

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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

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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

UN SDGs

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