Phakellisins A-E, cyclopeptides from a marine sponge Phakellia sp. guided by LC-MS

Can Kong; Ying Wu; Hui-Min Zhao; Shuai-Shuai Zhang; Zong-Mei Wu; Xiao-Bin Li; Ke-Chun Liu; Hou-Wen Lin; Shu-Ping Wang

doi:10.1016/j.bioorg.2023.106699

Phakellisins A-E, cyclopeptides from a marine sponge Phakellia sp. guided by LC-MS

Bioorg Chem. 2023 Oct:139:106699. doi: 10.1016/j.bioorg.2023.106699. Epub 2023 Jun 23.

Authors

Can Kong¹, Ying Wu², Hui-Min Zhao², Shuai-Shuai Zhang³, Zong-Mei Wu², Xiao-Bin Li¹, Ke-Chun Liu¹, Hou-Wen Lin⁴, Shu-Ping Wang⁵

Affiliations

¹ Engineering Research Center of Zebrafish Models for Human Diseases and Drug Screening of Shandong Province, Key Laboratory for Biosensor of Shandong Province, Biology Institute, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250103, Shandong, People's Republic of China.
² Research Center for Marine Drugs, State Key Laboratory of Oncogene and Related Genes, Department of Pharmacy, Ren Ji Hospital, School of Medicine, Shanghai Jiao Tong University, Shanghai 200127, People's Republic of China.
³ School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, Liaoning, People's Republic of China.
⁴ Engineering Research Center of Zebrafish Models for Human Diseases and Drug Screening of Shandong Province, Key Laboratory for Biosensor of Shandong Province, Biology Institute, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250103, Shandong, People's Republic of China; Research Center for Marine Drugs, State Key Laboratory of Oncogene and Related Genes, Department of Pharmacy, Ren Ji Hospital, School of Medicine, Shanghai Jiao Tong University, Shanghai 200127, People's Republic of China. Electronic address: franklin67@126.com.
⁵ Research Center for Marine Drugs, State Key Laboratory of Oncogene and Related Genes, Department of Pharmacy, Ren Ji Hospital, School of Medicine, Shanghai Jiao Tong University, Shanghai 200127, People's Republic of China. Electronic address: shupingwang2007@163.com.

PMID: 37390633
DOI: 10.1016/j.bioorg.2023.106699

Abstract

A chemical investigation of the marine sponge Phakellia sp. from the South China Sea yielded five new cyclopeptides, phakellisins A-E (1-5). Structures of these compounds were determined by comprehensive analysis of 1D/2D NMR, HRESIMS/MS spectroscopic data and the advanced Marfey's method. All compounds were evaluated for their cytotoxic activity. Compound 1 showed a strong inhibitory activity against WSU-DLCL-2 cells with an IC₅₀ value of 5.25 ± 0.2 μM by induction of G0/G1 cell cycle arrest and apoptosis.

Keywords: Cyclic peptides; Cytotoxic activity; Phakellia sp.; Structure elucidation.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Chromatography, Liquid
Magnetic Resonance Spectroscopy
Molecular Structure
Peptides, Cyclic* / chemistry
Peptides, Cyclic* / pharmacology
Porifera* / chemistry
Tandem Mass Spectrometry

Substances

Peptides, Cyclic