JBIR-12, a novel antioxidative agent from Penicillium sp. NBRC 103941

Miho Izumikawa; Aya Nagai; Takayuki Doi; Motoki Takagi; Kazuo Shin-Ya

doi:10.1038/ja.2009.13

JBIR-12, a novel antioxidative agent from Penicillium sp. NBRC 103941

Miho Izumikawa, Aya Nagai, Takayuki Doi, Motoki Takagi, Kazuo Shin-Ya

PHA - Molecular Pharmaceutical Science

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

9 Citations (Scopus)

Abstract

In the course of our screening program for active compounds from fungal metabolites, we isolated JBIR-12 (1) as a free radical scavenger from the culture broth of Penicillium sp. NBRC 103941. Structure elucidation of 1 was carried out using methylated and/or acetylated derivatives of 1. As a consequence, the structure of 1 was determined to be a novel highly oxygenated tetrahydronaphthalene species attached to an acyl chain moiety on the basis of NMR and other spectroscopic data. It was interesting that 1 was spontaneously methylated when left in methanol. Furthermore, isomerization or rearrangements could occur during the derivatization of 1. Compound 1 exhibited potent radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl radical with an IC"5"0 value of 75 μM.

Original language	English
Pages (from-to)	177-180
Number of pages	4
Journal	Journal of Antibiotics
Volume	62
Issue number	4
DOIs	https://doi.org/10.1038/ja.2009.13
Publication status	Published - 2009 Apr

Keywords

Antioxidative agent
JBIR-12
Penicillium sp.
Radical scavenging

ASJC Scopus subject areas

Pharmacology
Drug Discovery

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title = "JBIR-12, a novel antioxidative agent from Penicillium sp. NBRC 103941",

abstract = "In the course of our screening program for active compounds from fungal metabolites, we isolated JBIR-12 (1) as a free radical scavenger from the culture broth of Penicillium sp. NBRC 103941. Structure elucidation of 1 was carried out using methylated and/or acetylated derivatives of 1. As a consequence, the structure of 1 was determined to be a novel highly oxygenated tetrahydronaphthalene species attached to an acyl chain moiety on the basis of NMR and other spectroscopic data. It was interesting that 1 was spontaneously methylated when left in methanol. Furthermore, isomerization or rearrangements could occur during the derivatization of 1. Compound 1 exhibited potent radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl radical with an IC{"}5{"}0 value of 75 μM.",

keywords = "Antioxidative agent, JBIR-12, Penicillium sp., Radical scavenging",

author = "Miho Izumikawa and Aya Nagai and Takayuki Doi and Motoki Takagi and Kazuo Shin-Ya",

note = "Funding Information: This work was supported by a grant from the New Energy and Industrial Technology Department Organization (NEDO) of Japan.",

year = "2009",

month = apr,

doi = "10.1038/ja.2009.13",

language = "English",

volume = "62",

pages = "177--180",

journal = "Journal of Antibiotics",

issn = "0021-8820",

publisher = "Japan Antibiotics Research Association",

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T1 - JBIR-12, a novel antioxidative agent from Penicillium sp. NBRC 103941

AU - Izumikawa, Miho

AU - Nagai, Aya

AU - Doi, Takayuki

AU - Takagi, Motoki

AU - Shin-Ya, Kazuo

N1 - Funding Information: This work was supported by a grant from the New Energy and Industrial Technology Department Organization (NEDO) of Japan.

PY - 2009/4

Y1 - 2009/4

N2 - In the course of our screening program for active compounds from fungal metabolites, we isolated JBIR-12 (1) as a free radical scavenger from the culture broth of Penicillium sp. NBRC 103941. Structure elucidation of 1 was carried out using methylated and/or acetylated derivatives of 1. As a consequence, the structure of 1 was determined to be a novel highly oxygenated tetrahydronaphthalene species attached to an acyl chain moiety on the basis of NMR and other spectroscopic data. It was interesting that 1 was spontaneously methylated when left in methanol. Furthermore, isomerization or rearrangements could occur during the derivatization of 1. Compound 1 exhibited potent radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl radical with an IC"5"0 value of 75 μM.

AB - In the course of our screening program for active compounds from fungal metabolites, we isolated JBIR-12 (1) as a free radical scavenger from the culture broth of Penicillium sp. NBRC 103941. Structure elucidation of 1 was carried out using methylated and/or acetylated derivatives of 1. As a consequence, the structure of 1 was determined to be a novel highly oxygenated tetrahydronaphthalene species attached to an acyl chain moiety on the basis of NMR and other spectroscopic data. It was interesting that 1 was spontaneously methylated when left in methanol. Furthermore, isomerization or rearrangements could occur during the derivatization of 1. Compound 1 exhibited potent radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl radical with an IC"5"0 value of 75 μM.

KW - Antioxidative agent

KW - JBIR-12

KW - Penicillium sp.

KW - Radical scavenging

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