1H NMR studies of gossypol and its complexes with some organic compounds

Brzeziński, Bogumił; Olejnik, Judith; Paszỳc, S.; Aripov, T. F.

doi:10.1016/0022-2860(90)80116-2

Cited by 42 publications

(14 citation statements)

References 7 publications

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“…The optical rotation (α) of (+) and (−) Gossypol, expressed as + 348° and – 352° respectively, and 1 H NMR data (600 MHz, CDCl 3 : δ1.55 (d, 12H, J =5.5 Hz); 2.16 (s, 6H); 3.94 (m, 2H); 5.80 (s, 2H); 6.44 (s, 2H); 7.79 (s, 2H); 11.15 (s, 2H); 15.19 (s, 2H)) are in excellent agreement with published physical data for (+) and (−) gossypol [26]. The optical rotation of compounds 3a and 3b are −92.5° and + 95.0° respectively.…”

Section: Resultssupporting

confidence: 89%

Synthesis and evaluation of Apogossypol atropisomers as potential Bcl-xL antagonists

et al. 2009

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Anti-apoptotic Bcl-2 family proteins such as Bcl-2 and Bcl-X L have been recently validated as targets for the discovery of novel anti-cancer agents. We previously reported that racemic (+/−) Apogossypol, a semi-synthetic compound derived from the natural product Gossypol, binds and inhibits Bcl-2 and Bcl-X L in vitro and in cell. Given that (+) and (−) Gossypol display different proapoptotic activities, here we report on the synthesis of (+) and (−) Apogossypol and the evaluation of their in vitro and cellular activity.

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Section: Resultssupporting

confidence: 89%

Synthesis and evaluation of Apogossypol atropisomers as potential Bcl-xL antagonists

et al. 2009

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“…5a and b. The spectrum of gossypol was discussed earlier in detail [28]. The spectrum of GSBAL in Fig.…”

Section: Ft-ir Studiesmentioning

confidence: 99%

X-ray, FT-IR, ESI MS and PM5 studies of Schiff base of gossypol with allylamine and its complexes with alkali metal cations and perchlorate anion

et al. 2008

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Crystals of the Schiff base derivative of gossypol with allylamine (GSBAL) were grown and subsequently examined by X-ray diffraction and FT-IR methods. The crystal space group is C2/c with a = 16.057(1) Å , b = 14.112(1) Å , c = 27.185(2) Å , b = 99.371(5) and Z = 8. In the crystal, GSBAL exists in the enamineenamine tautomeric form. The FT-IR spectral features of the crystals are in agreement with the X-ray data indicating that both parts of the molecule are similarly intramolecular hydrogen-bonded but different intermolecular hydrogenbonded, although the molecule is symmetrically substituted. On the basis of the electrospray ionization mass spectrometry (ESI MS) experiments, it has been shown for the first time that Schiff base of gossypol forms complexes with the perchlorate anion and metal cations simultaneously. The ESI MS spectra of the 1:1:1 mixtures of GSBAL:GOS:M ? , in the positive and negative ion detection mode, have indicated the preferential formation of the 1:1 complexes of GSBAL with M ? (Li, Na or K) and ClO 4 -over the respective complexes forming between GOS and the metal cation or the anion. The PM5 semiempirical calculations have allowed visualization of the most energetically favourable structures of these two types of GSBAL complexes.

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“…In solvents such as CHCl 3 , benzene, acetone, or dioxane, gossypol's 1 H NMR spectrum shows the aldehydic 3 to be the only tautomeric form present in solution (80)(81)(82). The dialdehyde tautomer is also the predominant form found in the solid state (76,83).…”

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Reaction chemistry of gossypol and its derivatives

Kenar

2006

J Americ Oil Chem Soc

107

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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.

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1H NMR studies of gossypol and its complexes with some organic compounds

Cited by 42 publications

References 7 publications

Synthesis and evaluation of Apogossypol atropisomers as potential Bcl-xL antagonists

Synthesis and evaluation of Apogossypol atropisomers as potential Bcl-xL antagonists

X-ray, FT-IR, ESI MS and PM5 studies of Schiff base of gossypol with allylamine and its complexes with alkali metal cations and perchlorate anion

Reaction chemistry of gossypol and its derivatives

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