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.
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Acknowledgements
This study was supported by funds from the Institute for Fermentation, Osaka (IFO), Japan, the JSPS KAKENHI for Young Scientists (B) (grant number JP17K15250 and JP15K18601) and a Kitasato University Research Grant for Young Researchers awarded to Hirotaka, M. We thank Dr. Kenichiro Nagai, School of Pharmacy, Kitasato University, for HRESIMS measurements and the crew of the R/V Natsushima, and the operation team of the ROV Hyper-Dolphin for their cooperation in collecting deep-sea samples.
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Matsuo, H., Mokudai, T., Higo, M. et al. Cipralphelin, a new anti-oxidative N-cinnamoyl tripeptide produced by the deep sea-derived fungal strain Penicillium brevicompactum FKJ-0123. J Antibiot 72, 775–778 (2019). https://doi.org/10.1038/s41429-019-0208-6
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DOI: https://doi.org/10.1038/s41429-019-0208-6
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