ImageFileL1 = Gossypol.png
ImageSizeL1 = 200px
ImageFileR1 = Gossypol_(structure).png
ImageSizeR1 = 220px
IUPACName = 2,2′-bis-(Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene)
Section1 = Chembox Identifiers
CASNo = 303-45-7
SMILES = CC(C)c2c1cc(C)c(c(c4O)c(C)cc3c4c(C=O) c(O)c(O)c3C(C)C)c(O)c1c(C=O)c(O)c2O
InChI = 1/C30H30O8/c1-11(2)19-15-7- 13(5)21(27(35)23(15)17(9- 31)25(33)29(19)37)22- 14(6)8-16-20(12(3)4)30(38) 26(34)18(10-32)24(16) 28(22)36/h7-12,33-38H,1-6H3
Section2 = Chembox Properties
Formula = C30H30O8
MolarMass = 518.563 g/mol
Appearance = Brown solid
MeltingPt =177 - 182 °C (dec)
Section3 = Chembox Hazards
Gossypol C30H30O8 is a
polyphenolderived from the cotton plant (genus " Gossypium", family " Malvaceae"). Gossypol is a polyphenolic aldehydethat permeates cells and acts as an inhibitorfor several dehydrogenase enzymes. It is a yellow pigment.
Among other things, it has been tested as a
male oral contraceptivein China. In addition to its contraceptive properties, gossypol has also long been known to possess anti-malarialproperties. Other researchers are investigating the anti-cancer properties of gossypol.
It has proapoptotic properties, probably due to the regulation of the Bax and
Bcl2. It also reversibly inhibits Calcineurinand binds to calmodulin. Inhibits replication of the HIV-1 virus. It is an effective protein kinase Cinhibitor. [ [http://www.bioscreening.net/glossary/gossypol/ About Gossypol at Bioscreening.net] ]
A 1929 investigation in
Jiangxishowed correlation between low fertility in males and use of crude cottonseed oilfor cooking. The compound causing the contraceptive effect was determined to be gossypol.
In the 1970s, the Chinese government began researching the use of gossypol as a
contraceptive. Their studies involved over 10,000 subjects, and continued for over a decade. They concluded that gossypol provided reliable contraception, could be taken orally as a tablet, and did not upset men's balance of hormones.
However, gossypol also had serious flaws. The studies also discovered an abnormally high rate of
hypokalemiaamong subjects. Hypokalemia — low blood potassiumlevels — is usually the result of kidneymalfunction and causes symptoms of fatigue, muscle weakness, and at its most extreme, paralysis. In addition, about 7% of subjects reported effects on their digestive system, and about 12% increased fatigue. Most subjects recovered after stopping treatment and taking potassium supplements. A later study showed that taking potassium supplements during gossypol treatment did not prevent hypokalemia in primates.
In the mid-1990s, the
Brazilian pharmaceutical company Hebron announced plans to market a low-dose gossypol pill called Nofertil, but the pill never came to market. Its release was indefinitely postponed due to unacceptably high rates of permanent infertility. Between five and twenty-five percent of the men remained azoospermicup to a year after stopping treatment. The longer the men had taken the drug and the higher their overall dosage, the more likely the men were to have lowered fertility or to become completely infertile. Researchers have suggested that gossypol might make a good non-invasive alternative to surgical vasectomy. [cite journal|journal=Contraception| author=Coutinho, F. M.| title = Gossypol: a contraceptive for men| date = Apr 2002| volume = 65| issue = 4| pages = 259–263| pmid= 12020773| doi = 10.1016/S0010-7824(02)00294-9]
In 1986, the Chinese stopped research because of these side effects.Fact|date=March 2007
In 1998, the
World Health Organization's Research Group on Methods for the Regulation of Male Fertility recommended that research should be abandoned. In addition to the other side effects, the WHO researchers were concerned about gossypol's toxicity: the toxic dose in primates is less than 10 times the contraceptive dose. This report effectively ended further studies of gossypol as a temporary contraceptive, but research into using it as an alternative to vasectomycontinues in Austria, Brazil, Chile, China, the Dominican Republic, and Nigeria.
Gossypol is also under investigation as a possible chemotherapy drug especially in its R- state. It is currently believed that gossypol in itself will not kill cancerous cells, however it changes the chemistery within the cancer cell and makes it more suceptible to traditional chemotherapy drugs. Phased trials have been done on resistant prostate and lung cancer. Few results have been published to date so no conclusions can be drawn.
Food and animal agricultural industries must manage cotton-derivative product levels to avoid toxicity. For example, only
ruminant microfloracan digest gossypol, but only to a certain level, and cottonseed oil must be refined.
Texas A&M Universityhave genetically engineered cotton plants that contain very little gossypol in the seed, but still contain the compound in the stems and leaves. This provides protection against pests and diseases, while allowing the seed to be used for oil and meal for human consumption. The plants are modified by RNAi, shutting down the genes for gossypol production in the seed while leaving them unaffected in the rest of the plant. The resulting gossypol-free cottonseed is then suitable as a high-quality proteinsource suitable for consumption not only by cattle, but also by humans, pigs, chickens, or turkeys, making the plant additionally valuable as a food crop. [ [http://www.medgadget.com/archives/2006/11/cottonseed_prot.html Cottonseed Protein: From Farmers to Your Family Table - Medgadget - www.medgadget.com ] ]
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