8-Hydroxy-(+)-delta-cadinene is a precursor to hemigossypol in Gossypium hirsutum.
[(3)H](+)-delta-Cadinene and its 8-hydroxy derivative, prepared from (1RS)-[1-(3)H]FPP by the action of one and two recombinant enzymes, respectively, were infiltrated into cotyledons of bacterial blight-resistant cotton plants as they biosynthesized sesquiterpene phytoalexins in response to infection by Xanthomonas campestris pv. malvacearum. Following both treatments, tritium appeared in the HPLC fraction that contained hemigossypol. Hemigossypol was isolated from the cotyledons that had been treated with [(3)H](+)-8-hydroxy-delta-cadinene and was trimethylsilylated and purified. In two experiments, specific radioactivity of the hemigossypol derivative indicated that 5% and 10%, respectively, of the [(3)H](+)-8-hydroxy-delta-cadinene had been converted to hemigossypol.
Wang
Yan-Hong
YH
Department of Biochemistry and Molecular Biology, Oklahoma State University, Stillwater, OK 74078-3035, USA.
Davila-Huerta
Guadalupe
G
Essenberg
Margaret
M
D018548:Cotyledon / Q000378:metabolism; D003368:Gossypium / Q000378:metabolism*; D006072:Gossypol / Q000031:analogs & derivatives* / Q000096:biosynthesis*; D007536:Isomerism; D008861:Microsomes / Q000378:metabolism; D000081223:Polycyclic Sesquiterpenes; D012588:Scintillation Counting; D012717:Sesquiterpenes / Q000737:chemistry / Q000378:metabolism*; D014297:Trimethylsilyl Compounds / Q000737:chemistry; D014316:Tritium
D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; D014297:Trimethylsilyl Compounds; D014316:Tritium; C000607799:delta-cadinene; D006072:Gossypol