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Gossypol (Gossipol)

Polyphenol C30H30O8 from plants of the Gossypium genus, Malvaceae.

Gossypol Structure

Molecular Weight: 518.5634
Molecular f0rmula: C30H30O8
Melting Point: 177-182°C (decomp.)
CAS Number: 303-45-7
Name: 2,2′-bis-(Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene)

Additional Information About Gossypol

Description and Properties

Brown solid. PROTECT FROM LIGHT. PACKAGED UNDER INERT GAS. A cell-permeable polyphenolic aldehyde extracted from cotton seeds that acts as an inhibitor of several dehydrogenases and thereby depletes cellular energy. Shown to be an effective PKC inhibitor. Exhibits antitumor and proapoptotic properties, probably linked to the regulation of Bax and Bcl-2. Reported to act as an inhibitor of microtubule assembly and amyloid-b formation. Acts as a reversible Calcineurin (CaN) inhibitor (IC50 = 14-17 mM). Also inhibits replication of HIV type 1 and binds to calmodulin, abolishing Ca2+-dependent enhancement of dansyl-calmodulin fluorescence.

Ref.: Merck Index 13, 4543. Baumgrass, R., et al. 2001. J. Bio. Chem. 276, 47914. Heiser, V., et al. 2000. Proc. Natl. Acad. Sci. USA 97, 6739. Wang, X., et al. 2000. Life Sci. 67, 2663. Shidaifat, F., et al. 1997. Anticancer Res. 17, 1003. Jarvis, W.D., et al. 1994. Cancer Res. 54, 1707. Pelosin, J.M., et al. 1990. Biochem. Biophys. Res. Commun. 169, 1040. Medrano, E.J., and Andreu, J.M. 1986. Eur. J. Biochem. 158, 63.

About Gossypol, Definitions of Gossypol

– An anticancer drug extracted from the cotton plant

– Gossypol is a polyphenol C30H30O8derived from the cottonseed plant (genus Gossypium, family Malvaceae)used as a male oral contraceptive in China. Its efficacy is comparable to the female birth control pill.

– A pigment normally found in cotton which gives this crop some resistance to insects

Chemical Names
2,2′-bis-(Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene), ((1,1′,6,6′,7,7′-hexahydroxy-5,5′-diisopropyl-3,3′-dimethyl)2,2′-binaphthyl)-8,8′-dicarbaldehyde

Gossypol Biological Properties

  • A polyphenolic aldehyde that permeates cells and acts as an inhibitor for several dehydrogenase enzymes.
  • Gossypol is antimalarial being the selective inhibitor of Plasmodium falciparum (pfLDH over hLDHs), an essential enzyme for energy generation within malarial parasite.
  • Posesses proapoptotic properties, probably due to the regulation of the Bax and Bcl2.
  • Reversibly inhibits Calcineurin and binds to calmodulin.
  • Inhibits replication of the HIV-1 virus.
  • An effective protein kinase C inhibitor.

Additional information about Gossypol

Gossipol, Gossypol Dipotassium Salt; Gossypol Sodium Salt; Gossypol, (+)-Isomer; Gossypol, (+-)-Isomer; Gossypol, (-)-Isomer; Dipotassium Salt, Gossypol; Sodium Salt, Gossypol.

A dimeric sesquiterpene found in cottonseed (GOSSYPIUM). The (-) isomer is active as a male contraceptive (CONTRACEPTIVE AGENTS, MALE) whereas toxic symptoms are associated with the (+) isomer.

GOSSYPIUM

A plant genus of the family MALVACEAE. It is the source of COTTON FIBER; COTTONSEED OIL, which is used for cooking, and GOSSYPOL. The economically important cotton crop is a major user of agricultural PESTICIDES.

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