Gossypol. Synthesis and in vitro spermicidal activity of isomeric hemigossypol derivatives

Manmade, A.; Herlihy, Patricia; Quick, James Campbell; Duffley, R. P.; Grande, María José López; Hoffer, Anita P.

doi:10.1007/bf01990368

Cited by 15 publications

(7 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…12) in 5% overall yield by Edwards and Cashaw (36)(37)(38). From this pioneering work, much research (47,54,56,175,(184)(185)(186)(187)(188)(189)(190)(191)(192)(193) has followed to devise new, higher-yielding methodologies to prepare gossypol's basic naphthalene framework. This work is beyond the scope of this review.…”

Section: Gossypol Reactionsmentioning

confidence: 99%

Reaction chemistry of gossypol and its derivatives

Kenar

2006

J Americ Oil Chem Soc

109

View full text Add to dashboard Cite

Gossypol, a complex polyphenolic compound, is a naturally occurring highly colored yellow pigment found in the small intercellular pigment glands in the leaves, stems, roots, and seed of cotton plants. In cottonseed, gossypol contributes to its toxicity and therefore it is regarded as an unwanted processing component. It was not until its antitumor and male infertility activities were discovered that gossypol was considered as a valueadded natural product from cottonseed with useful physiological and chemical properties. These serendipitous discoveries created much excitement, and an enormous amount of research on gossypol has ensued. Since then, much research has focused on the preparation of suitable gossypol derivatives for medicinal applications. This review summarizes current knowledge about gossypol, its stereochemistry, tautomerism, and the many varied reactions the gossypol molecule can undergo.

show abstract

Section: Gossypol Reactionsmentioning

confidence: 99%

Reaction chemistry of gossypol and its derivatives

Kenar

2006

J Americ Oil Chem Soc

109

View full text Add to dashboard Cite

show abstract

“…40 Unfortunately, compound 11 41 is the 2-formyl regioisomer of compound 3 and its structure was verified by methylation to give the known compound 12 . 17 Using the same conditions on compound 7b , which has a methyl group in position two, 10% of compound 10b was obtained.…”

mentioning

confidence: 97%

“…16 Furthermore, it was reported that methylated hemigossypol displayed comparable spermicidal activity as gossypol. 17 Hemigossylic lactone with a methoxy group on position six is a natural product isolated from the root bark of B. malabarium; 18 however, bioactivity has not been reported. In order to explore SAR of hemigossypol and hemigossylic lactone, we developed a short and convenient synthetic scheme to synthesize hemigossypol and its 2,5-alkyl substituted derivatives.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of hemigossypol and its derivatives

Wei

Jagt

Royer

et al. 2010

Tetrahedron Letters

View full text Add to dashboard Cite

Hemigossypol (3), a sesquiterpene natural product, was previously isolated from Gossypium barbadense and was shown to display improved anti-fungal activity compared to gossypol (1), the disesquiterpene dimer of hemigossypol (3). Gossypol exhibits multiple biological activities. In order to study whether hemigossypol and it derivatives retain the various bioactivities of gossypol, we developed a short and convenient synthetic scheme to synthesize hemigossypol. This is the first de novo synthesis of this natural product. In addition derivatives of hemigossypol with various 2,5-alkyl substituents were synthesized. Modification of the synthetic scheme also afforded the natural product hemigossylic lactone (4) and its 2,5-substituted derivatives.

show abstract

“…and is used as a male contraceptive agent [1]. Gossypol is orally administered and absorbed at a dose level of 5 or 10 mg/kg bw for it to induce male sterility in hamsters and rats [2].…”

Section: Introductionmentioning

confidence: 99%

Characterization of ion interference in gossypol consumption

Achudume

Eno

1996

Adv Contracept

View full text Add to dashboard Cite

The goal of the present investigation was to show that gossypol has the potential of ion interference capable of affecting the metabolic activation of the biologic system. Gossypol was administered orally at 20 mg/kg body weight (bw) for 8 weeks and the animals were fed a controlled diet. At the end of the experiment, liver supernatant was subjected to atomic absorption spectrometry. The characteristic ion interferences were examined for calcium, ferrous, sodium, magnesium, potassium and chloride ions. Glutathione level and lactate dehydrogenase activity were also monitored. The peak heights for calcium and ferrous ions were high and low respectively but the ion ratio for calcium is suggestive of a ligand-like substance that may be cumulative, thereby leading to biologic magnification (toxicity).

show abstract

Gossypol. Synthesis and in vitro spermicidal activity of isomeric hemigossypol derivatives

Abstract: Three isomeric hemigossypol derivatives (3,4,5) have been synthesized. Two of these derivatives (3,4) and one synthetic intermediate (7) have been shown to have activity comparable to gossypol (1) in a sperm motility assay.

Cited by 15 publications

References 5 publications

Reaction chemistry of gossypol and its derivatives

Reaction chemistry of gossypol and its derivatives

Synthesis of hemigossypol and its derivatives

Characterization of ion interference in gossypol consumption

Contact Info

Product

Resources

About