It07:Gossypol
Introduction
| Gossypol | |
|---|---|
| |
| IUPAC Systematic name | |
| 2,2′-bis-(Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene) | |
| Other name | |
| Gossypol | |
| Indentifiers | |
| ATC Code | |
| CAS number | {{{CASNo}}} |
| PubChem (CID) | 24895349 |
| SMILES | CC(C)C1=C(C=C(C)C(C3=C(O)C(C(C=O)=C(O)C(O)=C4C(C)C)=C4C=C3C)=C2O)C2=C(C=O)C(O)=C1O |
| Chemical Data | |
| Molecular formula | C30H30O8 |
| Molar mass | 518.554 g/mol |
| Pharmacokinetic Data | |
| Bioavailability | |
| Protein Binding | {{{Protein_binding}}} |
| Metabolism | |
| Half life | |
| Excretion | |
| Therapeutic considerations | |
| Pregnancy cat. | |
| Legal status | |
| Routes | |
| UV-Vis | |
|---|---|
| λmax | ? nm |
| Extinction coefficient, ε | ? |
| IR | |
| Major absorption bands | ? cm−1 |
| NMR | |
Proton NMR Summarise of H NMR for Gossypol
Proton Gossypol (δ0)
2- OH 5.740
4- H 7.802
6- OH 6.448
7- OH 15.225
CHO 11.185
CH 3.589
Isopropyl methyl 1.579
Phenyl methyl 2.169
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| Carbon-13 NMR | Carbon-13NMR |
| Other NMR data | |
| MS | |
| Masses of main fragments |
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Gossypol, C30H30O8, is a pigment named after the species of cotton gossypium L., malvaceae, that bears the seeds from which it is extracted. Initially known only as an undesirable toxin found in foods that contained cottonseed oil, it was thought to have potential uses as a rubber antioxidant, a stabilizer for vinyl polymers and as a potential insecticide. Today it is known primarily as a male oral contraceptive, after the discovery of remarkable fertility suppressive effects in men.
History
In 1929, to investigate anecdotal evidence that families who cooked with crude cottonseed oil produced fewer children, a large scale Chinese fertility survey was carried out. The study concluded that it was this oil that affected male fertility, and it was determined that gossypol in the cotton seed oil could be used as a contraceptive. During the 1970s over 8,000 men were tested using this type of contraceptive and it was found that men taking a daily gossypol pill had reliable contraception. '[I'd like to see sources for the previous paragraph please]'
In late 2005, a team of researchers at Sunderland University found that gossypol has been seen to help stop the spread of psoriasis, a fairly common and unpleasant genetic skin condition, as well as reducing inflammation in sufferers. Psoriasis suffers have a genetic fault that means that under certain conditions their skin starts to produce far too many skin cells.
It is knwon that gossypol exists as 3 differnt tautomeric forms. This is important as it determines gossypol's solubility by changing its polarity. Ther interconversion within gossypol's are shown below.
Uses and side effects
In 1970s, the Chinese proposed gossypol as a drug for male contraceptive use. Studies conducted by the International Organisation for Chemical Sciences in Development has shown that 40 of the 70 purified forms of gossypol were just as active as the original gossypol.[1]
Among the side effects assiciated with the use of gossypol, the most serious was hypokalemic paralysis. Hypokalemic paralysis[2] is also known as 'familial paralysis', and occurs due to low levels of potassium in the body. During an attack of paralysis, muscle weakness occurs in arms and legs. In more severe cases, this may also affect swallowing and breathing, which can be fatal. Also there are few other toxic symptoms such as reptosprisis, heart failure and jaundice.
Recovery of those who used gossypol is 75%; however, it can lead to other related symptoms such as smaller testicular colume, and elevated follicle stimulating hormone concentrations.
Known hazards
May be irritating to gastrointestinal tract. Large doses have caused edema of lungs, shortness of breath and paralysis in animals. Toxic to nonruminant animals such as humans, by reducing the capacity the blood has to carry oxygen.
A large-scale trial of gossypol was carried out in China. A high rate of hypokalemia was shown is test subjects.
A man who uses the drug for protracted periods could become partially, if not fully, infertile.
References
- The Merck Index- An Encylopedia of Chemicals, Drugs and Biologicals, Thirteenth edition, Merck & Co., Inc.