title: An antibacterial metabolite from Lasiodiplodia pseudotheobromae F2.
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.
authors: Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210093, PR China.
authors: Wei
authors: W
authors: Wei
authors: School of Pharmacy, Nanjing Medical University, Nanjing 210029, PR China.
authors: Nan
authors: N
authors: Jiang
authors: Department of Clinical Laboratory, The First Affiliated Hospital of Nanjing Medical University, Nanjing 210029, PR China.
authors: Ya Ning
authors: YN
authors: Mei
authors: Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210093, PR China.
authors: Yan Liang
authors: YL
authors: Chu
authors: Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210093, PR China.
authors: Hui Ming
authors: HM
authors: Ge
authors: Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210093, PR China.
authors: Yong Chun
authors: YC
authors: Song
authors: Department of Chemistry, University of Malaya, Kuala Lumpur 50603, Malaysia.
authors: Seik Weng
authors: SW
authors: Ng
authors: Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210093, PR China. Electronic address: rxtan@nju.edu.cn.
authors: Ren Xiang
authors: RX
authors: Tan
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism* / Q000494:pharmacology*; D001203:Ascomycota / Q000378:metabolism*; D001419:Bacteria / Q000187:drug effects; D054659:Diketopiperazines / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism* / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D008968:Molecular Conformation
chemical_list: D000900:Anti-Bacterial Agents; D054659:Diketopiperazines
keywords: Antibacterial; Hernandiaceae; Illigera rhodantha; Lasiodipline; Lasiodiplodia pseudotheobromae; Structure elucidation; Sulfureous diketopiperazine