Is gossypol water soluble?
Gossypol was soluble in ether and acetone, but only sparingly soluble in other common organic solvents. It was insoluble in water, but dissolved readily in dilute ammonia and sodium carbonate.
Why is gossypol considered chiral?
Because of restricted rotation of the internaphthyl bond, gossypol is a chiral compound, which has two atropisomers (i.e., (+)- and (-)-gossypol) that exhibit different levels of biological activities.
What is gossypol in chemistry?
Gossypol is a natural phenol derived from the cotton plant (genus Gossypium). Gossypol is a phenolic aldehyde that permeates cells and acts as an inhibitor for several dehydrogenase enzymes. It is a yellow pigment. The structure exhibits axial chirality, with the two enantiomers having different biochemical properties.
What is free gossypol?
Gossypol is a polyphenolic compound which occurs in free or (protein-) bound forms and is found in both the vegetative and reproductive tissues of the cotton plant (Gossypium L.); the highest levels of which are found in the cottonseeds. Cottonseeds are used as a feed material due to their high protein content.
What is gossypol used for?
Gossypol is a polyphenol isolated from the seed, roots, and stem of the cotton plant (Gossypium sp.). The substance, a yellow pigment similar to flavonoids, is present in cottonseed oil. In the plant, it acts as a natural defensive agent against predators, provoking infertility in insects.
What feed contains gossypol?
Gossypol is a phenolic compound produced by pigment glands in cotton stems, leaves, seeds, and flower buds (Gossypium spp.). Cottonseed meal is a by-product of cotton that is used for animal feeding because it is rich in oil and proteins. However, gossypol toxicity limits cottonseed use in animal feed.
What is the mode of action of gossypol?
Gossypol is non-steroidal and does not affect hormone levels, but does inhibit sperm production and motility in male animals and humans. It acts as a contraceptive by inhibiting enzyme systems that effect energy metabolism in sperm and spermatogenic cells (Coutinho, 2002. (2002). Gossypol: A contraceptive for men.
How is gossypol produced?
Gossypol is a phenolic compound produced by pigment glands in cotton stems, leaves, seeds, and flower buds (Gossypium spp.). Cottonseed meal is a by-product of cotton that is used for animal feeding because it is rich in oil and proteins.
How toxic is gossypol?
High concentrations of free gossypol may be responsible for acute clinical signs of gossypol poisoning which include respiratory distress, impaired body weight gain, anorexia, weakness, apathy, and death after several days. However, the most common toxic effects is the impairment of male and female reproduction.
How can gossypol be prevented?
Preventive procedures to limit gossypol toxicity involve treatment of the cottonseed product to reduce the concentration of free gossypol with the most common treatment being exposure to heat. However, free gossypol can be released from the bound form during digestion.
What is gossypol contraception?
Does okra contain gossypol?
A unique substance in okra is “gossypol”. It is a polyphenolic compound that is mostly found in okra seeds. Gossypol is also found in other species of the mallow family, such as cotton and cacao, with cottonseeds containing the highest concentrations.
What is the mechanism of action of gossypol?
Mechanism of Action. Gossypol was found to be cytotoxic in HL-60 cells with the IC (50) dose of 4.5 microM. The combination of gossypol and okadaic acid in IC (50) doses revealed the increased cytotoxicity in a time-dependent manner. Treatment of cells with gossypol has shown significant decrease in PP2A activity.
What are the side effects of gossypol 50 mg?
Grade I-II toxicities with gossypol treatment included nausea in 30% of patients, fatigue 15%, emesis 15%, altered taste sensation 15% and diarrhea in 10% of patients. Two of the three patients receiving 50 mg/day experienced dose limiting dermatologic toxicity (grade III).
How is the Koc of gossypol determined?
Using a structure estimation method based on molecular connectivity indices(1), the Koc of gossypol can be estimated to be 1.2X10+6(SRC). According to a classification scheme(2), this estimated Koc value suggests that gossypol is expected to be immobile mobility in soil.
Where can I find gossypol in my body?
This agent also inhibits cell-signaling enzymes, resulting in inhibition of cell growth, and may act as a male contraceptive. (-)-Gossypol is found in fats and oils. (-)-Gossypol is a constituent of Gossypium hirsutum (cotton). Gossypol has been used in trials studying the treatment of Non-small Cell Lung Cancer.