Novel 11-norbetaenone isolated from an entomopathogenic fungus Lecanicillium antillanum

Chi-Ying Li; I-Wen Lo; Shih-Wei Wang; Tsong-Long Hwang; Yu-Ming Chung; Yuan-Bin Cheng; Sung-Pin Tseng; Yi-Hung Liu; Yu-Ming Hsu; Shu-Rong Chen; Hao-Chun Hu; Fang-Rong Chang; Yang-Chang Wu

doi:10.1016/j.bmcl.2017.03.019

Novel 11-norbetaenone isolated from an entomopathogenic fungus Lecanicillium antillanum

Bioorg Med Chem Lett. 2017 May 1;27(9):1978-1982. doi: 10.1016/j.bmcl.2017.03.019. Epub 2017 Mar 11.

Authors

Affiliations

¹ Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan.
² Department of Medicine, Mackay Medical College, New Taipei City 252, Taiwan.
³ 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.
⁴ 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.
⁵ Department of Medical Laboratory Science and Biotechnology, College of Health Sciences, Kaohsiung Medical University, Kaohsiung 807, Taiwan.
⁶ Instrumentation Center, National Taiwan University, Taipei 106, Taiwan.
⁷ 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.
⁸ 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.

PMID: 28336142
DOI: 10.1016/j.bmcl.2017.03.019

Abstract

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.

Keywords: Anti-angiogenic effect; Betaenone; Lecanicillium antillanum; Polyketide synthase; Secondary metabolite.

Publication types

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

MeSH terms

Angiogenesis Inhibitors / chemistry*
Angiogenesis Inhibitors / isolation & purification
Angiogenesis Inhibitors / pharmacology*
Crystallography, X-Ray
Diterpenes / chemistry*
Diterpenes / isolation & purification
Diterpenes / pharmacology*
Endothelial Progenitor Cells / cytology
Endothelial Progenitor Cells / drug effects
Humans
Hypocreales / chemistry*
Magnetic Resonance Spectroscopy
Models, Molecular

Substances

11-norbetaenone
Angiogenesis Inhibitors
Diterpenes