Structural highlights
Function
CLM1_GIBZE Terpene cyclase involved in the biosynthesis of culmorin, a tricyclic sesquiterpene diol reported to have antifungal activity and some phytotoxicity to wheat coleoptile tissue, contributing to Fusarium head blight disease (Probable) (PubMed:19880637). The terpene cyclase CLM1 is responsible for the cyclization of farnesyl diphosphate into the intermediate longiborneol (PubMed:19880637). Longiborneol is then hydroxylated in a regio- and endo-stereoselective manner at position C-11 by the cytochrome P450 monooxygenase CLM2 to produce culmorin (PubMed:26673640). Additional non-specific oxygenases are also able to hydroxylate longiborneol at other sites than C-11 leading to 3-hydroxylongiborneol, 5-hydroxylongiborneol, 12-hydroxylongiborneol and 15-hydroxylongiborneol (PubMed:26673640). Moreover, another oxygenase capable of installing a C-11 exo-hydroxy group in longiborneol can also yield 11-epi-acetylculmorin (PubMed:26673640). The production of these longiborneol derivatives is dwarfed by the high abundance of culmorin, suggesting that CLM2 displays superior enzymatic activity to the unidentified, possibly promiscuous, additional oxygenases (PubMed:26673640).[1] [2] [3]
References
- ↑ McCormick SP, Alexander NJ, Harris LJ. CLM1 of Fusarium graminearum encodes a longiborneol synthase required for culmorin production. Appl Environ Microbiol. 2010 Jan;76(1):136-41. PMID:19880637 doi:10.1128/AEM.02017-09
- ↑ Bahadoor A, Schneiderman D, Gemmill L, Bosnich W, Blackwell B, Melanson JE, McRae G, Harris LJ. Hydroxylation of Longiborneol by a Clm2-Encoded CYP450 Monooxygenase to Produce Culmorin in Fusarium graminearum. J Nat Prod. 2016 Jan 22;79(1):81-8. PMID:26673640 doi:10.1021/acs.jnatprod.5b00676
- ↑ Bresso E, Leroux V, Urban M, Hammond-Kosack KE, Maigret B, Martins NF. Structure-based virtual screening of hypothetical inhibitors of the enzyme longiborneol synthase-a potential target to reduce Fusarium head blight disease. J Mol Model. 2016 Jul;22(7):163. PMID:27324634 doi:10.1007/s00894-016-3021-1