Novel 11-norbetaenone isolated from an entomopathogenic fungus Lecanicillium antillanum.
A novel nor-betaenone compound, 11-norbetaenone (1), was isolated from the culture broth of an entomopathogenic fungus Lecanicillium antillanum. The structure was determined on the basis of 1D and 2D NMR spectroscopic data. The absolute stereochemistry of 1 was further confirmed by X-ray single crystallography analysis. It is the first secondary metabolite reported from the species Lecanicillium antillanum. And it is also the first time that a betaenone-type compound was isolated from the genus Lecanicillium. Furthermore, 11-norbetaenone (1) displayed significant anti-angiogenic effect by suppressing tube formation.
Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan.
Chi-Ying
CY
Li
Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan.
I-Wen
IW
Lo
Department of Medicine, Mackay Medical College, New Taipei City 252, Taiwan.
Shih-Wei
SW
Wang
Graduate Institute of Natural Products, College of Medicine and Chinese Herbal Medicine Research Team, Healthy Aging Research Center, Chang Gung University, Taoyuan 333, Taiwan; Research Center for Industry of Human Ecology, Research Center for Chinese Herbal Medicine, and Graduate Institute of Health Industry Technology, College of Human Ecology, Chang Gung University of Science and Technology, Taoyuan 333, Taiwan; Department of Anesthesiology, Chang Gung Memorial Hospital, Taoyuan 333, Taiwan.
Tsong-Long
TL
Hwang
Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan.
Yu-Ming
YM
Chung
Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan; Center for Infectious Disease and Cancer Research, Kaohsiung Medical University, Kaohsiung 807, Taiwan; Research Center for Natural Products & Drug Development, Kaohsiung Medical University, Kaohsiung 807, Taiwan.
Yuan-Bin
YB
Cheng
Department of Medical Laboratory Science and Biotechnology, College of Health Sciences, Kaohsiung Medical University, Kaohsiung 807, Taiwan.
Sung-Pin
SP
Tseng
Instrumentation Center, National Taiwan University, Taipei 106, Taiwan.
Yi-Hung
YH
Liu
Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan.
Yu-Ming
YM
Hsu
Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan.
Shu-Rong
SR
Chen
Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan.
Hao-Chun
HC
Hu
Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan; Center for Infectious Disease and Cancer Research, Kaohsiung Medical University, Kaohsiung 807, Taiwan; Department of Marine Biotechnology and Resources, National Sun Yat-Sen University, Kaohsiung 804, Taiwan; Cancer Center, Kaohsiung Medical University Hospital, Kaohsiung 807, Taiwan; Research Center for Environmental Medicine, Kaohsiung Medical University, Kaohsiung 807, Taiwan. Electronic address: aaronfrc@kmu.edu.tw.
Fang-Rong
FR
Chang
Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan; School of Pharmacy, College of Pharmacy, China Medical University, Taichung 404, Taiwan; Chinese Medicine Research and Development Center, China Medical University Hospital, Taichung 404, Taiwan; Center for Molecular Medicine, China Medical University Hospital, Taichung 404, Taiwan; Research Center for Chinese Herbal Medicine, China Medical University, Taichung 404, Taiwan. Electronic address: yachwu@mail.cmu.edu.tw.
Yang-Chang
YC
Wu
D020533:Angiogenesis Inhibitors / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D066026:Endothelial Progenitor Cells / Q000166:cytology / Q000187:drug effects; D006801:Humans; D006999:Hypocreales / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular
C000621235:11-norbetaenone; D020533:Angiogenesis Inhibitors; D004224:Diterpenes
Anti-angiogenic effect; Betaenone; Lecanicillium antillanum; Polyketide synthase; Secondary metabolite