Gossypol

A natural polyphenol with diverse effects

Gossypol is a racemic mixture of natural polyphenols isolated from parts of the cotton plant (genus Gossypium). It causes infertility in a variety of cotton pests and spermatogenesis arrest in humans.1 Gossypol also has antimalarial properties, preventing the growth of P. falciparum at low micromolar concentrations.2 It inhibits aldose reductase (Ki = 0.5 µM).3 Gossypol also acts as an anticancer agent, inhibiting cell growth in various cancer cell lines, in part by blocking the anti-apoptotic functions of Bcl-2 and Bcl-xL, again at low micromolar concentrations.4

518.6

≥85%

(±)-Gossypol|BL 193|NSC 56817|NSC 624336|Pogosin

OC1=C(O)C(C(C)C)=C(C=C(C)C(C2=C(O)C(C(C([H])=O)=C(O)C(O)=C3C(C)C)=C3C=C2C)=C4O)C4=C1C([H])=O

C30H30O8

303-45-7

≥ 4 years

DMF: 20 mg/ml DMF:PBS(pH 7.2)(1:1): 0.5 mg/ml DMSO: 16.7 mg/ml Ethanol: 14.3 mg/ml

1.Coutinho, E.M. Gossypol: A contraceptive for men. Contraception 65(4), 259-263 (2002).
2.Royer, R.E.,Deck, L.M.,Campos, N.M., et al. Biologically active derivatives of gossypol: Synthesis and antimalarial activities of peri-acylated gossylic nitriles. Journal of Medicinal Chemistry 29(9), 1799-1801 (1986).
3.Deck, L.M.,Vander Jagt, D.L. and Royer, R.E. Gossypol and derivatives: A new class of aldose reductase inhibitors. Journal of Medicinal Chemistry 34(11), 3301-3305 (1991).
4.Yan, F.,Cao, X.X.,Jiang, H.X., et al. A novel water-soluble gossypol derivative increases chemotherapeutic sensitivity and promotes growth inhibition in colon cancer. Journal of Medicinal Chemistry 53(15), 5502-5510 (2010).