Occurrence of (+)- and (−)-Gossypol in Wild Species of Cotton and in Gossypium hirsutum Var. marie-galante (Watt) Hutchinson

Gossypol occurs as a mixture of enantiomers in cottonseed. These enantiomers exhibit different biological activities. The (−)-enantiomer is toxic to animals, but it has potential medicinal uses. Therefore, cottonseed with >95% (−)-gossypol could have biopharmaceutical applications. The (+)-enanti...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2005-08, Vol.53 (16), p.6266-6271
Main Authors: Stipanovic, Robert D, Puckhaber, Lorraine S, Bell, Alois A, Percival, Albert E, Jacobs, John
Format: Article
Language:English
Subjects:
Animal Feed
chemical composition
cotton
cottonseed
enantiomers
Gossypium
Gossypium - chemistry
Gossypium hirsutum
gossypol
Gossypol - analysis
Gossypol - chemistry
Gossypol - toxicity
seeds
Seeds - chemistry
Stereoisomerism
Structure-Activity Relationship
varieties
wild relatives
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Summary:Gossypol occurs as a mixture of enantiomers in cottonseed. These enantiomers exhibit different biological activities. The (−)-enantiomer is toxic to animals, but it has potential medicinal uses. Therefore, cottonseed with >95% (−)-gossypol could have biopharmaceutical applications. The (+)-enantiomer shows little, if any, toxicity to nonruminant animals. Thus, cottonseed with >95% (+)-gossypol could be more readily utilized as a feed for nonruminants. The (+)- to (−)-gossypol ratio in commercial Upland (Gossypium hirsutum) cottonseed is usually about 3:2, whereas that in commercial Pima cottonseed (Gossypium barbadense) is approximately 2:3. Herein are reported the (+)- to (−)-gossypol ratios in the seed from 28 wild species of cotton (194 accessions), 94 accessions of G. hirsutum var. marie-galante, and 3 domesticated species (11 accessions). It was found that some or all of the accessions of Gossypium darwinii, Gossypium sturtianum, Gossypium areysianum, Gossypium longicalyx, Gossypium harknessii, and Gossypium costulatum produce an excess of (−)-gossypol but none >65%. At least one accession of Gossypium anomalum, Gossypium mustelinum, Gossypium gossypioides, and Gossypium capitis-viridis contained >94% (+)-gossypol. One of the 94 accessions of G. hirsutum var. marie-galante (i.e., no. 2469) contained 97% (+)-gossypol. Keywords: Cotton; (+)-gossypol; (−)-gossypol; Gossypium; wild cotton species; G. hirsutum var. marie-galante
ISSN:0021-8561
1520-5118
DOI:10.1021/jf050702d