title: Toxicity of (+)- and (-)-gossypol to the plant pathogen, Rhizoctonia solani.
abstract: The dimeric sesquiterpene gossypol occurs naturally in cottonseed and other parts of the cotton plant. Gossypol exists as enantiomers because of the restricted rotation around the central binaphthyl bond. The (-)-enantiomer is toxic to nonruminant animals while the (+)-enantiomer exhibits little, if any, toxicity to these animals. Developing cotton plants with low levels of the (-)-gossypol could expand the use of cottonseed as a feed source. Gossypol also may play a role in protecting the plant from pathogens. The relative toxicity of (+)- and (-)-gossypol to plant pathogens has not been reported. We measured the concentration of (+)- and (-)-gossypol in roots from cotton seedlings that were treated with the biocontrol agent Trichoderma virens that induces biosynthesis of gossypol and related terpenoids in cotton roots. (-)-Gossypol was the minor enantiomer in control and treated roots, but levels were slightly higher in roots from T. virens-treated seed. We also determined the toxicity of the gossypol enantiomers and the racemate to the seedling disease pathogen Rhizoctonia solani. The (+)- and (-)-enantiomers of gossypol and the racemate are equally effective in inhibiting growth of this pathogen. The lethal doses of the gossypols required to kill the pathogen appeared to be similar, but their toxicities are significantly less than those of related cotton and kenaf sesquiterpenes. The results indicate that altering the enantiomeric ratio in cotton roots will not adversely affect the resistance of seedlings to the seedling pathogen R. solani.
authors.affiliation: USDA-ARS, Southern Plains Agricultural Research Center, 2765 F&B Road, College Station, Texas 77845, USA.
authors.forename: Lorraine S
authors.initials: LS
authors.lastname: Puckhaber
authors.forename: Michael K
authors.initials: MK
authors.lastname: Dowd
authors.forename: Robert D
authors.initials: RD
authors.lastname: Stipanovic
authors.forename: Charles R
authors.initials: CR
authors.lastname: Howell
mesh_terms: D003368:Gossypium / Q000737:chemistry* / Q000382:microbiology*; D006072:Gossypol / Q000032:analysis / Q000494:pharmacology*; D010935:Plant Diseases / Q000382:microbiology; D018517:Plant Roots / Q000737:chemistry; D012232:Rhizoctonia / Q000187:drug effects* / Q000254:growth & development; D036226:Seedlings / Q000737:chemistry / Q000382:microbiology; D012639:Seeds / Q000737:chemistry; D013237:Stereoisomerism; D014242:Trichoderma
chemical_list: D006072:Gossypol