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

Hirotaka Matsuo, Takayuki Mokudai, Mayuka Higo, Kenichi Nonaka, Yuriko Nagano, Takahiko Nagahama, Yoshimi Niwano, Yōko Takahashi, Satoshi Ōmura, Takuji Nakashima

    Research output: Contribution to journalArticlepeer-review

    3 Citations (Scopus)

    Abstract

    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.

    Original languageEnglish
    Pages (from-to)775-778
    Number of pages4
    JournalJournal of Antibiotics
    Volume72
    Issue number10
    DOIs
    Publication statusPublished - 2019 Oct 1

    ASJC Scopus subject areas

    • Pharmacology
    • Drug Discovery

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