Comparative anti‐fertility effects of gossypol enantiomers in male hamsters

Lindberg, Marjorie C.; Naqvi, Rehan H.; Matlin, Stephen A.; Zhou, Rong; Bialy, G.; Blye, Richard P.

doi:10.1111/j.1365-2605.1987.tb00361.x

Cited by 44 publications

(22 citation statements)

References 7 publications

(7 reference statements)

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“…1). Known for its ability to inhibit maturation in human sperm, [1][2][3][4] gossypol has recently attracted considerable interest for its potential as an antineoplastic agent. [5][6][7][8][9][10] Gossypol is an axial chiral compound due to restricted rotation about the internaphthyl 2-2Ј-bond, which results in helical sense (M) or (P).…”

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confidence: 99%

Determination of the absolute configuration and solution conformation of gossypol by vibrational circular dichroism

et al. 2003

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Vibrational circular dichroism (VCD) measurements and density functional theory (DFT) calculations were used to obtain the first definitive assignment of the absolute configuration for the polyphenolic binaphpthyl dialdehyde gossypol and a determination of the solution conformation in CDCl(3). VCD spectra recorded for the two resolved enantiomers are near mirror images and excellent agreement between the observed IR and VCD spectra and intensity calculations carried out at the DFT (B3LYP/6-31G*) level establish the absolute configurations of (+)-gossypol as P and (-)-gossypol as M, with two conformations in CDCl(3) solution that differ in isopropyl group orientation.

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confidence: 99%

Determination of the absolute configuration and solution conformation of gossypol by vibrational circular dichroism

et al. 2003

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“…Both forms are produced by the cotton plant, but in ratios that vary with cotton species, variety, and tissue [15][16][17][18]. Considerable work has established that the gossypol enantiomers have different anti-cancer and anti-viral activities [3,4,7,8], contraceptive effects [9,10], and animal toxicities [19].…”

Section: Gossypolmentioning

confidence: 99%

“…Gossypol also has a wide range of potentially important biological activity, including inhibitory effects against viruses [3,4], protozoa [5], and cancer cells [6][7][8]. The compound also exhibits male contraceptive effects [9][10][11].…”

Section: Gossypolmentioning

confidence: 99%

HPLC preparation of the chiral forms of 6-methoxy-gossypol and 6,6′-dimethoxy-gossypol

Dowd

Pelitire

2008

Journal of Chromatography B

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“…12 Recent research indicates that individual gossypol enantiomers do not contribute equally to the compound's biological effects. 2,8,9,11 To further our understanding of these differences, improved methods are needed for the preparation of enantiomeric gossypol in high chemical and optical purity.…”

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confidence: 99%

“…1 As a natural product, the compound exhibits a wide spectrum of activity, including contraceptive, 2,3 antitumor, [4][5][6][7][8][9] antiamebic, 10 and antiviral effects. 11 Gossypol can also be toxic to animals overfed cottonseed products.…”

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confidence: 99%

Preparation of enantiomeric gossypol by crystallization

Dowd

2003

Chirality

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Large enantiomorphic crystals of gossypol-acetone (1:3) were grown from acetone solutions of rac-gossypol-acetic acid (1:1) at 4 degrees C. By controlling the initial gossypol concentration, crystallization time, and solution volume, single crystals were grown that weighed >50 mg, equivalent to >37 mg of enantiomeric gossypol. Even larger crystals were possible, but it was difficult to produce these reliably without contamination of the antipode. Essentially all of the acetone within the crystal form was removed by storing the crystals under vacuum for 3-4 days. By employing these techniques, gram quantities of enantiomeric gossypol were prepared in high chemical and optical purity. Based on measured and reported optical rotations, the optical purity of samples prepared by crystallization was greater than the optical purity of samples prepared by chromatographic separation of gossypol-amine diastereomers. The principal limitation of crystallization as a preparative method is the need to determine the chirality and purity of each product crystal. Nevertheless, the method competes favorably with preparative-scale chromatographic procedures.

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Comparative anti‐fertility effects of gossypol enantiomers in male hamsters

Abstract: The enantiomers of gossypol have been tested as male oral anti-fertility agents in hamsters. As determined by fertility tests the (-) isomer was fully active at half the effective dose of the racemate, whereas the (+) isomer exerted no anti-fertility effect.

Cited by 44 publications

References 7 publications

Determination of the absolute configuration and solution conformation of gossypol by vibrational circular dichroism

Determination of the absolute configuration and solution conformation of gossypol by vibrational circular dichroism

HPLC preparation of the chiral forms of 6-methoxy-gossypol and 6,6′-dimethoxy-gossypol

Preparation of enantiomeric gossypol by crystallization

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