An antibacterial metabolite from Lasiodiplodia pseudotheobromae F2

Wei Wei; Nan Jiang; Ya Ning Mei; Yan Liang Chu; Hui Ming Ge; Yong Chun Song; Seik Weng Ng; Ren Xiang Tan

doi:10.1016/j.phytochem.2014.01.003

An antibacterial metabolite from Lasiodiplodia pseudotheobromae F2

Phytochemistry. 2014 Apr:100:103-9. doi: 10.1016/j.phytochem.2014.01.003. Epub 2014 Feb 12.

Authors

Wei Wei¹, Nan Jiang², Ya Ning Mei³, Yan Liang Chu¹, Hui Ming Ge¹, Yong Chun Song¹, Seik Weng Ng⁴, Ren Xiang Tan⁵

Affiliations

¹ Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210093, PR China.
² School of Pharmacy, Nanjing Medical University, Nanjing 210029, PR China.
³ Department of Clinical Laboratory, The First Affiliated Hospital of Nanjing Medical University, Nanjing 210029, PR China.
⁴ Department of Chemistry, University of Malaya, Kuala Lumpur 50603, Malaysia.
⁵ Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210093, PR China. Electronic address: rxtan@nju.edu.cn.

PMID: 24529576
DOI: 10.1016/j.phytochem.2014.01.003

Abstract

In searching for symbionts derived from bioactive natural products, six sulfureous diketopiperazines designated as lasiodiplines A-F (1-6) were characterized from the culture of Lasiodiplodia pseudotheobromae F2, previously residing in the apparently normal flower of Illigera rhodantha (Hernandiaceae). Identification of structures was accomplished by a combination of spectroscopic and computational approaches, in conjunction with the low-temperature (100K) single-crystal X-ray diffraction with Cu Kα radiation. Lasiodipline E (5) was demonstrated to be antibacterial against the clinical strains Streptococcus sp., Bacteroides vulgates, Peptostreptococcus sp. and Veillonella parvula, respectively, with an minimum inhibitory concentration (MIC) range of 0.12-0.25 μg/mL. In addition, compounds 4 and 6 exemplify two unusual architectures of natural cyclodipeptides, signifying the unique biochemical characteristics of the producing fungus.

Keywords: Antibacterial; Hernandiaceae; Illigera rhodantha; Lasiodipline; Lasiodiplodia pseudotheobromae; Structure elucidation; Sulfureous diketopiperazine.

Publication types

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

MeSH terms

Anti-Bacterial Agents / chemistry
Anti-Bacterial Agents / isolation & purification
Anti-Bacterial Agents / metabolism*
Anti-Bacterial Agents / pharmacology*
Ascomycota / metabolism*
Bacteria / drug effects
Diketopiperazines / chemistry
Diketopiperazines / isolation & purification
Diketopiperazines / metabolism*
Diketopiperazines / pharmacology*
Microbial Sensitivity Tests
Models, Molecular
Molecular Conformation

Substances

Anti-Bacterial Agents
Diketopiperazines