title: Gossypol--a polyphenolic compound from cotton plant.
abstract: Gossypol (C(30)H(30)O(8)) is a polyphenolic compound derived from the cotton plant (genus Gossypium, family Malvaceae). The presence of six phenolic hydroxyl groups and two aldehydic groups makes gossypol chemically reactive. Gossypol can undergo Schiff base formation, ozonolysis, oxidation, and methylation to form gossypol derivatives. Gossypol and its derivatives have been the target of much research due to their multifaceted biological activities including antifertility, antivirus, anticancer, antioxidant, antitrypanosomal, antimicrobial, and antimalarial activities. Because of restricted rotation of the internaphthyl bond, gossypol is a chiral compound, which has two atropisomers (i.e., (+)- and (-)-gossypol) that exhibit different levels of biological activities. This chapter covers the physiochemical properties, analyses, biological properties, and agricultural and clinical implications of gossypol.
authors.affiliation: Department of Genetics and Biochemistry, Clemson University, Clemson, South Carolina 29634, USA.
authors.forename: Xi
authors.initials: X
authors.lastname: Wang
authors.forename: Cheryl Page
authors.initials: CP
authors.lastname: Howell
authors.forename: Feng
authors.initials: F
authors.lastname: Chen
authors.forename: Juanjuan
authors.initials: J
authors.lastname: Yin
authors.forename: Yueming
authors.initials: Y
authors.lastname: Jiang
mesh_terms: D016573:Agrochemicals / Q000737:chemistry / Q000494:pharmacology / Q000633:toxicity; D000821:Animal Feed / Q000009:adverse effects / Q000032:analysis; D000818:Animals; D055598:Chemical Phenomena; D003369:Cottonseed Oil / Q000737:chemistry; D004353:Drug Evaluation, Preclinical; D003368:Gossypium / Q000737:chemistry*; D006072:Gossypol / Q000031:analogs & derivatives / Q000737:chemistry* / Q000494:pharmacology / Q000633:toxicity; D006801:Humans; D012639:Seeds / Q000737:chemistry*
chemical_list: D016573:Agrochemicals; D003369:Cottonseed Oil; D006072:Gossypol