TY - JOUR
T1 - Biosynthesis of the cyclooligomer depsipeptide bassianolide, an insecticidal virulence factor of Beauveria bassiana
AU - Xu, Yuquan
AU - Orozco, Rousel
AU - Kithsiri Wijeratne, E. M.
AU - Espinosa-Artiles, Patricia
AU - Leslie Gunatilaka, A. A.
AU - Patricia Stock, S.
AU - Molnár, István
N1 - Funding Information: Financial support for this work was provided by Contract 0013 awarded by the Arizona Biomedical Research Commission, and a grant from the Center of Insect Science, University of Arizona. R. O. acknowledges support of the Bio5 Institute, University of Arizona. HRFABMS service was provided by Dr. A. Somogyi at the University of Arizona Chemistry Core Facility.
PY - 2009/5
Y1 - 2009/5
N2 - Beauveria bassiana is a facultative entomopathogen with an extremely broad host range that is used as a commercial biopesticide for the control of insects of agricultural, veterinary and medical significance. B. bassiana produces bassianolide, a cyclooligomer depsipeptide secondary metabolite. We have cloned the bbBsls gene of B. bassiana encoding a nonribosomal peptide synthetase (NRPS). Targeted inactivation of the B. bassiana genomic copy of bbBsls abolished bassianolide production, but did not affect the biosynthesis of beauvericin, another cyclodepsipeptide produced by the strain. Comparative sequence analysis of the BbBSLS bassianolide synthetase revealed enzymatic domains for the iterative synthesis of an enzyme-bound dipeptidol monomer intermediate from d-2-hydroxyisovalerate and l-leucine. Further BbBSLS domains are predicted to catalyze the formation of the cyclic tetrameric ester bassianolide by recursive condensations of this monomer. Comparative infection assays against three selected insect hosts established bassianolide as a highly significant virulence factor of B. bassiana.
AB - Beauveria bassiana is a facultative entomopathogen with an extremely broad host range that is used as a commercial biopesticide for the control of insects of agricultural, veterinary and medical significance. B. bassiana produces bassianolide, a cyclooligomer depsipeptide secondary metabolite. We have cloned the bbBsls gene of B. bassiana encoding a nonribosomal peptide synthetase (NRPS). Targeted inactivation of the B. bassiana genomic copy of bbBsls abolished bassianolide production, but did not affect the biosynthesis of beauvericin, another cyclodepsipeptide produced by the strain. Comparative sequence analysis of the BbBSLS bassianolide synthetase revealed enzymatic domains for the iterative synthesis of an enzyme-bound dipeptidol monomer intermediate from d-2-hydroxyisovalerate and l-leucine. Further BbBSLS domains are predicted to catalyze the formation of the cyclic tetrameric ester bassianolide by recursive condensations of this monomer. Comparative infection assays against three selected insect hosts established bassianolide as a highly significant virulence factor of B. bassiana.
KW - Agrobacterium-mediated transformation
KW - Cyclic depsipeptide
KW - Insect pathogenesis assay
KW - Iterative biosynthesis
KW - Nonribosomal peptide synthetase
KW - Virulence
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U2 - 10.1016/j.fgb.2009.03.001
DO - 10.1016/j.fgb.2009.03.001
M3 - Article
C2 - 19285149
SN - 1087-1845
VL - 46
SP - 353
EP - 364
JO - Fungal Genetics and Biology
JF - Fungal Genetics and Biology
IS - 5
ER -