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The novel agricultural fungicide 3-[5-(4-chlorophenyl)-2,3-dimethyl-3-isoxazolidinyl] pyridine (SYP-Z048) developed by China Shenyang Research Institute of Chemical Industry has been confirmed to be an ergosterol biosynthesis inhibitor (EBI). Previous studies have shown that EBIs target the proteins from a range of genes, including  CYP51 ,  ERG2  and/or  ERG24 , and  ERG27 , which are involved in the ergosterol biosynthesis pathway. In the current study the  ERG2 ,  ERG24 , and  ERG27  genes were cloned from wild type and resistant mutants of  Monilinia fructicola  in an attempt to clarify the target site of SYP-Z048. Comparative analysis of the deduced aa sequence of these genes, as well as  CYP51 , revealed several point mutations that resulted in amino acid variation among the sensitive and resistant isolates. However, sensitivity assays indicated that only one, the substitution of phenylalanine (F) for the tyrosine (Y) at 136 in  CYP51 , was correlated with reduced sensitivity to SYP-Z048. Heterologous expression of  MfCYP51 - 136Y  ( MfCYP136Y ) and  MfCYP51 - 136F  ( MfCYP136F)  in  Pichia pastoris  revealed that  MfCYP136F  significantly reduced sensitivity to SYP-Z048, increasing the average EC 50  of the transformants 11-fold relative to those carrying  MfCYP136Y . However, neither the additional copy of  MfCYP136Y  nor multiple copies of  MfCYP136F  were found to reduce sensitivity relative to the empty vector control or single copy transformants, respectively. Molecular docking experiments using SYP-Z048 with  HsCYP145Y  and the mutated version  HsCYP145F  as substitutes for  MfCYP136Y  and  MfCYP136F , respectively, indicated that the reduced affinity of  HsCYP145F  for SYP-Z048 resulted from the loss of a hydrogen bond between the fungicide and the active site. Taken together these results indicate that  MfCYP51  is the major target site of SYP-Z048 in  M. fructicola , which has important implications for the resistance management of this fungicide in the field.

frontiers in microbiology

Heterologous expression of the Monilinia fructicola CYP51 (MfCYP51) gene in Pichia pastoris confirms the mode of action of the novel fungicide, SYP-Z048