On the Botanical Distribution of Chiral Forms of Gossypol

Abstract

Plants belonging to Malvaceae (about 90 species belonging to 33 genera) were analysed for the presence of gossypol by reversed-phase HPLC using absorbance detection at 365 nm, and the chirality and optical purity of gossypol were determined whenever the analysis was positive. Only plants belonging to the cotton tribe (Gossypieae) contained gossypol (detection limit better than 0.001%). In particular, no gossypol could be detected in ABELMOSCHUS ESCULENTUS (ocra), HIBISCUS TILIACEUS, H. SABDARIFFA, and HEREA BRASI-LIENSIS, earlier claimed to contain this compound. Gossypol-containing plants usually produced dextrorotatory gossypol of varying optical purity; an enantiomeric excess of (-)-gossypol was detected in only one plant, GOSSYPIUTN BARBADENSE.

HPLC preparation of the chiral forms of 6-methoxy-gossypol and 6,6′-dimethoxy-gossypol

“…Seed had slightly more (−)-gossypol (52.7%) than (+)-gossypol (47.3%). A small excess of (−)-gossypol is frequently observed in the seed for G. barbadense varieties [13,15,16] and has been previously reported for this variety [13]. In the root bark, (+)-gossypol is in considerable excess relative to (−)-gossypol.…”

“…As a result, gossypol exists in two enantiomeric forms. Both forms are produced by the cotton plant, but in ratios that vary with cotton species, variety, and tissue [15][16][17][18]. Considerable work has established that the gossypol enantiomers have different anti-cancer and anti-viral activities [3,4,7,8], contraceptive effects [9,10], and animal toxicities [19].…”

Small-Molecule Inhibitors of Human Ldh5

“…Gossypol is usually found in high concentrations in the pigment glands of the cotton plant. Hence its name derives from Gossypium , the plant from which it was originally isolated, but it was subsequently found in several other closely related genera belonging to the Malvaceae family [40]. Together, with other sesquiterpenoids detected in these plants, gossypol exerts the function of a natural insecticide, defending the plant from attacks of several kinds of pathogens and insects [41].…”

Therapeutic potential of gossypol: An overview

“…ex Corrêa, both members of the family Malvaceae (Figure 1; Jaroszewski et al, 1992a;King & de Silva, 1968). Gossypol is produced in the plant by the dimerization of two molecules of hemigossypol and is best classified as a dimeric-sesquiterpenoid.…”