Structure, properties of gossypol and its derivatives—from physiological activities to drug discovery and drug design

Abstract

Gossypol is a polyphenolic compound isolated from cottonseed.

Biogenetic and biomimetic synthesis of natural bisditerpenoids: hypothesis and practices

“…[21][22][23] The formation of DACD (3) was achieved by photochemical [4 + 2] dimerization in vitro starting from the monomer ent-15,16epoxy-19-hydroxy-1,3,13( 16),14-clerodatetraen-18-oic acid (DAC); both DAC and DACD have antioxidant and antinociceptive effects. 24 The example labdane dimers, ent-13 0nor-13 0 -oxomethylisoozate dimer (9) and ent-methylisoozate dimer (10), were isolated from the stem bark of Xylopia aromatica. 25 Cunlanceloic acids B-D (11)(12)(13) are asymmetric labdane DA adducts isolated from the cones of Cunninghamia lanceolata.…”

“…The subsequent Claisen rearrangement of 261c provided the intermediate 261d , which then underwent an intramolecular 5- exo -trig cyclization to produce the intermediate 261e . Then, nonstereoselective reduction of Δ 9,10 double bond in 261e would afford enantiomers 261–266 (Scheme 22). 153…”

“…However, they can exhibit multiple biological functions that are absent or weak in their monomers, such as the antifertility effect of gossypol and the anticancer effect of vinblastine. 9,10 Among the many types of natural oligomers, oligomeric terpenoids are famous for their structural complexity and diversity; accordingly, studies have reported the discovery of oligomeric terpenoids, such as dimers, trimers, and tetramers of sesquiterpenes. 4 So far, for higher terpenoids, only dimeric diterpenoids and triterpenoids have been discovered, 2,11 partly because of the challenges of isolation and identication posed by the greater structural complexity.…”

“…However, they can exhibit multiple biological functions that are absent or weak in their monomers, such as the antifertility effect of gossypol and the anticancer effect of vinblastine. 9,10…”

Application of Mathematical Modeling and Physico-Chemical Analysis Methods in the Prediction of Biological Activity and Quality Control of Gossypol Derivatives

“…The natural polyphenol gossypol contained in cotton (genus Gossypium, family Malvaceae) is of great interest in pharmacy due to the high biological activity detected in this natural compound [1,2]. Gossypol was discovered by Longmore and Marchlewski at the turn of the 19 th and 20 th centuries, having purified it by precipitation from an essential solution using acetic acid [3].…”