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

• Published in: Journal of agricultural and food chemistry Vol. 53; no. 16; pp. 6266 - 6271
• Main Authors: Stipanovic, Robert D, Puckhaber, Lorraine S, Bell, Alois A, Percival, Albert E, Jacobs, John
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 10.08.2005
• 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
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf050702d

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