Cipralphelin, a new anti-oxidative N-cinnamoyl tripeptide produced by the deep sea-derived fungal strain Penicillium brevicompactum FKJ-0123

• Published in: Journal of antibiotics Vol. 72; no. 10; pp. 775 - 778
• Main Authors: Matsuo, Hirotaka, Mokudai, Takayuki, Higo, Mayuka, Nonaka, Kenichi, Nagano, Yuriko, Nagahama, Takahiko, Niwano, Yoshimi, Takahashi, Yōko, Ōmura, Satoshi, Nakashima, Takuji
• Format: Journal Article
• Language: English
• Published: London Nature Publishing Group UK 01-10-2019; Nature Publishing Group
• Subjects: 101/58; 639/154; 639/638; Amino acids; Antibiotics; Antioxidants - chemistry; Antioxidants - isolation & purification; Antioxidants - metabolism; Antioxidants - pharmacology; Bacteriology; Biological Products - chemistry; Biological Products - isolation & purification; Biological Products - metabolism; Biological Products - pharmacology; Biomedical and Life Sciences; Bioorganic Chemistry; Brief Communication; Chromatography; Chromatography, Liquid; Cinnamates - chemistry; Cinnamates - isolation & purification; Cinnamates - metabolism; Cinnamates - pharmacology; Cytotoxicity; Deep sea; Free Radical Scavengers - chemistry; Free Radical Scavengers - isolation & purification; Free Radical Scavengers - metabolism; Free Radical Scavengers - pharmacology; Fungi; Life Sciences; Liquid chromatography; Magnetic Resonance Spectroscopy; Mass Spectrometry; Medicinal Chemistry; Metabolites; Microbial activity; Microbiology; Molecular Structure; NMR; Nuclear magnetic resonance; Oligopeptides - chemistry; Oligopeptides - isolation & purification; Oligopeptides - metabolism; Oligopeptides - pharmacology; Organic Chemistry; Penicillium - growth & development; Penicillium - metabolism; Seeds; Silica
• ISSN: 0021-8820; 1881-1469
• DOI: 10.1038/s41429-019-0208-6

A new
N
-cinnamoyl tripeptide, designated cipralphelin (
1
), was isolated from a cultured broth of
Penicillium brevicompactum
FKJ-0123 by physicochemical (PC) screening. Compound
1
was purified by silica gel and ODS column chromatography followed by preparative HPLC. The structure of
1
was determined as
N
-cinnamoyl-prolyl-alanyl-phenylalanine methyl ester by nuclear magnetic resonance and mass spectrometry analyses. The absolute configurations of three amino acids were determined by an advanced Marfey’s method applied to the hydrolysate of
1
. Compound
1
was evaluated for its cytotoxicity, anti-microbial activity, and ability to scavenge or quench reactive oxygen species (ROS) such as superoxide anion radicals, hydroxy radicals, and singlet oxygen. Compound
1
exhibited potent scavenging activity against hydroxy radicals.