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

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Cipralphelin, a new anti-oxidative N-cinnamoyl tripeptide produced by the deep sea-derived fungal strain Penicillium brevicompactum FKJ-0123.
The Journal of Antibiotics ( IF 2.1 ) Pub Date : 2019-07-22 , DOI: 10.1038/s41429-019-0208-6
Hirotaka Matsuo _{1,

2} , Takayuki Mokudai ₃ , Mayuka Higo ₁ , Kenichi Nonaka _{1,

2} , Yuriko Nagano ₄ , Takahiko Nagahama ₅ , Yoshimi Niwano ₆ , Yōko Takahashi ₁ , Satoshi Ōmura ₁ , Takuji Nakashima _{1,

2}

Affiliation

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.

中文翻译：

西弗拉林，一种新的抗氧化的N-肉桂酰基三肽，由深海衍生的真菌菌株Penicillium brevicompactum FKJ-0123生产。

通过理化（PC）筛选，从培养的短小青霉菌FKJ-0123的培养液中分离出一种新的N-肉桂酰基三肽，命名为西弗洛林（1）。化合物1通过硅胶和ODS柱色谱纯化，然后通过制备型HPLC纯化。通过核磁共振和质谱分析确定1的结构为N-肉桂酰基-脯氨酰基-丙氨酰基-苯丙氨酸甲酯。通过应用于1水解产物的先进Marfey方法确定三种氨基酸的绝对构型。对化合物1的细胞毒性，抗微生物活性以及清除或猝灭诸如超氧阴离子的活性氧（ROS）的能力进行了评估。自由基，羟基自由基和单线态氧。化合物1显示出对羟基自由基的有效清除活性。

更新日期：2019-11-18

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