JBIR-12, a novel antioxidative agent from Penicillium sp. NBRC 103941.
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(50) value of 75 microM.
Izumikawa
Miho
M
Biomedicinal Information Research Center, Japan Biological Informatics Consortium, Tokyo, Japan.
Nagai
Aya
A
Doi
Takayuki
T
Takagi
Motoki
M
Shin-Ya
Kazuo
K
D000107:Acetylation; D000975:Antioxidants / Q000737:chemistry / Q000494:pharmacology*; D001713:Biphenyl Compounds / Q000737:chemistry; D003470:Culture Media; D005285:Fermentation; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D009281:Naphthalenes / Q000737:chemistry / Q000494:pharmacology*; D016877:Oxidants / Q000737:chemistry; D010407:Penicillium / Q000378:metabolism*; D010851:Picrates / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet
D000975:Antioxidants; D001713:Biphenyl Compounds; D003470:Culture Media; C544288:JBIR-12; D009281:Naphthalenes; D016877:Oxidants; D010851:Picrates; C004931:1,1-diphenyl-2-picrylhydrazyl