Cyclic Hexapeptides from the Deep South China Sea-Derived Streptomyces scopuliridis SCSIO ZJ46 Active Against Pathogenic Gram-Positive Bacteria

Yongxiang Song; Qinglian Li; Xue Liu; Yuchan Chen; Yun Zhang; Aijun Sun; Weimin Zhang; Jingren Zhang; Jianhua Ju

doi:10.1021/np500399v

Cyclic Hexapeptides from the Deep South China Sea-Derived Streptomyces scopuliridis SCSIO ZJ46 Active Against Pathogenic Gram-Positive Bacteria

J Nat Prod. 2014 Aug 22;77(8):1937-41. doi: 10.1021/np500399v.

Authors

Yongxiang Song¹, Qinglian Li¹, Xue Liu², Yuchan Chen³, Yun Zhang¹, Aijun Sun¹, Weimin Zhang³, Jingren Zhang², Jianhua Ju¹

Affiliations

¹ CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences , 164 West Xingang Road, Guangzhou 510301, China.
² Center for Infectious Disease Research, School of Medicine, Tsinghua University , Beijing 100084, China.
³ Guangdong Institute of Microbiology , 100 Central Xianlie Road, Guangzhou 510070, China.

PMID: 25072108
DOI: 10.1021/np500399v

Abstract

Three new cyclohexapeptides, desotamides B-D (2-4), and the known desotamide (1) were isolated from marine microbe Streptomyces scopuliridis SCSIO ZJ46. The sequences and absolute configurations of 2-4 were elucidated on the basis of high-resolution spectroscopic data, Marfey's method, and chiral-phase HPLC data. Desotamide C (3) contains a unique N-formyl-kynurenine residue, whereas 4 lacks formylation at the same site. Compounds 1 and 2 displayed notable antibacterial activities against strains of Streptococcus pnuemoniae, Staphylococcus aureus, and methicillin-resistant Staphylococcus epidermidis (MRSE), and structure activity relationship studies revealed the indispensability of the Trp component for antibacterial activity within this new scaffold.

Publication types

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

MeSH terms

Amino Acid Sequence
Anti-Bacterial Agents / chemistry
China
Chromatography, High Pressure Liquid
Gram-Positive Bacteria / drug effects
Marine Biology
Methicillin Resistance / drug effects
Microbial Sensitivity Tests
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Peptides, Cyclic / chemistry
Peptides, Cyclic / isolation & purification*
Peptides, Cyclic / pharmacology*
Staphylococcus aureus / drug effects
Streptomyces / drug effects
Structure-Activity Relationship

Substances

Anti-Bacterial Agents
Peptides, Cyclic
desotamide B
desotamide C
desotamide D