The antifertility agent, gossypol, releases calcium from rat liver mitochondria

Martı́nez, Federico; Milán, Rebeca; Espinosa-García, María Teresa; Pardo, Juan Pablo

doi:10.1016/0742-8413(93)90129-9

Cited by 8 publications

(4 citation statements)

References 24 publications

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“…Gossypol decreased cell viability and down regulate the expression of some genes in human colon cancer cells [20]. Gossypol was demonstrated to be specific inhibitor of DNA synthesis [12]. Rosenberg et al (1986) highlighted that gossypol affects nuclear DNA by upregulating DNA replication and mismatched proteins [13].…”

Section: Introductionmentioning

confidence: 99%

Silica Gel Chromatographic Methods for Identification, Isolation and Purification of Gossypol Acetic Acids Prepared in Lab

Amara,

Hesham El-Masry,

Salem

et al. 2024

Preprint

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Quite a number of cottonseed varieties are existed. The seeds of each variety produce a different amount of gossypol as a natural toxic compound. The increased interest in this natural product and its toxic effects were enhanced the demand for establishing simple silica-gel-based methods for its isolation, purification, and characterization. Historically, silica gel plays a significant role in isolation and purification of many different natural products. Silica gel is variants and can intro-duce a lab, simple tool for tracking a compound in certain plants during its purification process. In this study, gossypol was isolated and purified in the form of yellow crystals as gossypol acetic ac-id. Several methods and tools were used for its characterization including TLC, preparative TLC, silica gel column, UV/IR spectrophotometer and HPLC (Robust spherical silica gel). A compara-tive study between its amounts in both Egyptian and Chinese varieties were performed. Under the experimental condition, the Egyptian cottonseeds contain 8.705 gm/kg, while the Chinese contains 5.395 gm/kg. Thin Layer Chromatography (TLC) had been flourished the science of the phytochemistry and still popular till nowadays and is recommended for fast, accurate, and inex-pensive evaluation and quantification of gossypol. It is recommended to isolate and purify gossy-pol as gossypol acetic acid using optimized combined methods used in this study. Using Silica gel different protocols will assist and facilitate the parallel comparison and save the compact column from any unexpected contaminants during the purification steps. During each step the silica gel itself could be simply removed by paper filtration.

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Section: Introductionmentioning

confidence: 99%

Silica Gel Chromatographic Methods for Identification, Isolation and Purification of Gossypol Acetic Acids Prepared in Lab

Amara,

Hesham El-Masry,

Salem

et al. 2024

Preprint

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“…The biological activity of gossypol is mainly due to a disturbance of mitochondrial function, such as modification of the mitochondrial concentration of Ca 2+ , that associated with membrane fluidity [ 11 ], disruption of oxidative phosphorylation by inhibition of mitochondrial succinic dehydrogenase [ 12 ], release of cytochrome c from mitochondria into the cytosol suggesting a mitochondrial-mediated apoptotic mechanism [ 13 , 14 ]. It is the diversity of mitochondrial dysfunctions that remains the problem of gossypol toxicity opened.…”

Section: Introductionmentioning

confidence: 99%

Gossypol Inhibits Electron Transport and Stimulates ROS Generation in Yarrowia lipolytica Mitochondria

Arinbasarova¹,

Меденцев²,

Krupyanko³

2012

Open Biochem J

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This work studied the effect of gossypol on the mitochondrial respiratory chain of Yarrowia lipolytica. The compound was shown to inhibit mitochondrial electron transfer and stimulate generation of reactive oxygen species. The inhibition kinetics in oxidation of various substrates (NADH, succinate, α-glycerophosphate and pyruvate + malate) by isolated mitochondria was investigated. Analysis of the kinetic parameters showed gossypol to inhibit two fragments of the mitochondrial electron transfer chain: a) between coenzyme Q and cytochrome b with KIIIi of 118.3 μM (inhibition by the noncompetitive type), and b) at the level of exogenous NADH dehydrogenase with of KIi 17.2 μM (inhibition by the mixed type).

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“…with a wide range of biological effects including antifertility, − antiproliferative, − antiviral, and immunomodulatory activities. − The diversity of these pharmacological effects of gossypol and its derivatives is partly attributable to their membranotrophic properties. A study of the distribution of 14 C-gossypol and its derivatives in subcellular fractions of rat hepatocytes showed that most of the label was located in the microsomes and mitochondria. , Gossypol and its derivatives concentrate in the lipid bilayers of biological membranes as they possess high affinity for lipids and induce both structural and functional alterations. − In particular, they make artificial and biological membranes permeable to mono- and divalent cations. The protonophoric activity of gossypol, uncoupling of mitochondria, ,, may account for its antifertility ,, and anticancerogenic ,, effects.…”

Section: Introductionmentioning

confidence: 99%

“…18,19 Gossypol and its derivatives concentrate in the lipid bilayers of biological membranes as they possess high affinity for lipids and induce both structural and functional alterations. [20][21][22][23][24][25][26] In particular, they make artificial and biological membranes permeable to mono-and divalent cations. The protonophoric activity of gossypol, uncoupling of mitochondria, 7,27,28 may account for its antifertility 4,5,7 and anticancerogenic 10,11,29 effects.…”

Section: Introductionmentioning

confidence: 99%

The Immobilization of Gossypol Derivative on N-Polyvinylpyrrolidone Increases its Water Solubility and Modifies Membrane-Active Properties

et al. 2009

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The conjugate of the gossypol derivative megosin (1) with N-polyvinylpyrrolidone named rometin (2) was synthesized. The effects of 1 and 2 on the structure and permeability of human erythrocytes and rat liver mitochondria were compared. Compound 1 induced dose-dependent erythrocyte hemolysis and increased mitochondrial permeability, with concomitant changes in membrane structure as determined by ESR and fluorescence anisotropy methods. Immobilization of 1 on N-polyvinylpyrrolidone (compound 2) increased its water solubility and reduced the intensity of its effects on erythrocyte membrane integrity and mitochondrial permeability, which correlated with a decrease in the membranes structural changes induced by the compound. Although the same concentrations of free and N-polyvinylpyrrolidone bound 1 were used, far less (14)C-labeled 1 was incorporated into the membranes from complex than free 1. The increase in water solubility and the reduction of membrane-active properties of 1 after immobilization on N-polyvinylpyrrolidone could explain our previous observation of the decreased toxicity of 1.

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The antifertility agent, gossypol, releases calcium from rat liver mitochondria

Cited by 8 publications

References 24 publications

Silica Gel Chromatographic Methods for Identification, Isolation and Purification of Gossypol Acetic Acids Prepared in Lab

Silica Gel Chromatographic Methods for Identification, Isolation and Purification of Gossypol Acetic Acids Prepared in Lab

Gossypol Inhibits Electron Transport and Stimulates ROS Generation in Yarrowia lipolytica Mitochondria

The Immobilization of Gossypol Derivative on N-Polyvinylpyrrolidone Increases its Water Solubility and Modifies Membrane-Active Properties

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