An antibacterial metabolite from Lasiodiplodia pseudotheobromae F2

Wei W 1 , Jiang N 2 , Mei YN 3 , Chu YL 1 , Ge HM 1 , Song YC 1 Show all authors , Ng SW 4 , Tan RX 5

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
Phytochemistry, 2014 Apr;100:103-9.
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.

* Title and MeSH Headings from MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.

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