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番荔枝环肽A的合成、表征及生物活性研究

Synthesis, Characterization, and Biological Activity Studies on Fanlizhicyclopeptide A.

作者信息

Dahiya Rajiv, Singh Sunil

机构信息

Laboratory of Peptide Research and Development,School of Pharmacy, Faculty of Medical Sciences, The University of the West Indies, St. Augustine, Trinidad & Tobago, West Indies.

Research Scholar, Department of Pharmacy, Mewar University, Gangrar, Chittorgarh, Rajasthan, India.

出版信息

Iran J Pharm Res. 2017 Summer;16(3):1176-1184.

Abstract

The synthesis of a proline-rich cyclic heptapeptide, fanlizhicyclopeptide A (8), previously isolated from the fruits of Annona squamosa (sugar-apples), is described via coupling of tetrapeptide -prolyl--tyrosyl--leucyl--proline methyl ester with tripeptide Boc-glycyl--valyl--proline followed by cyclization of the linear fragment having seven amino acid units. Structure of the synthesized cyclooligopeptide was confirmed by the means of chemical and spectroscopic methods including FTIR, H NMR, C NMR, FABMS and further, subjected to the anthelmintic, antibacterial and the antifungal activity studies. Bioactivity results indicated that the newly synthesized cyclic peptide displayed potent anthelmintic activity against the three earthworm species , and at 2 mg/mL and remarkable anti-dermatophytic activities against and at concentration of 6 g/mL.

摘要

本文描述了一种富含脯氨酸的环状七肽——番荔枝环肽A(8)的合成方法,该七肽先前是从番荔枝(释迦果)果实中分离得到的。合成过程是通过将四肽——脯氨酰——酪氨酰——亮氨酰——脯氨酸甲酯与三肽Boc-甘氨酰——缬氨酰——脯氨酸偶联,然后将具有七个氨基酸单元的线性片段环化。通过包括傅里叶变换红外光谱(FTIR)、氢核磁共振(1H NMR)、碳核磁共振(13C NMR)、快原子轰击质谱(FABMS)在内的化学和光谱方法确定了合成的环寡肽的结构,并进一步进行了驱虫、抗菌和抗真菌活性研究。生物活性结果表明,新合成的环肽在2 mg/mL时对三种蚯蚓(蚯蚓属、正蚓属和爱胜蚓属)显示出强效驱虫活性,在6 μg/mL浓度下对须癣毛癣菌和石膏样小孢子菌显示出显著的抗皮肤癣菌活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5a16/5610772/4f0fc30b2ba5/ijpr-16-1176-g001.jpg

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