Gossypol

Gossypol is a lipid of Prenol Lipids (PR) class. Gossypol is associated with abnormalities such as Paralytic Ileus, PARKINSON DISEASE, LATE-ONSET, Fibrillation, Hepatic necrosis and Lymphopenia. The involved functions are known as Atrophic, Ulcer, Necrosis, Apoptosis and antagonists. Gossypol often locates in Mucous Membrane, Epithelium, Blood, Microsomes, Liver and Autophagic vacuole. The associated genes with Gossypol are BCL2A1 gene, BCL2 gene, Transgenes, IGH@ gene cluster and Bax protein (53-86). The related lipids are Promega, proteoliposomes, Phosphatidylserines and Liposomes. The related experimental models are Transgenic Model and Xenograft Model.

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Introduction

To understand associated biological information of Gossypol, we collected biological information of abnormalities, associated pathways, cellular/molecular locations, biological functions, related genes/proteins, lipids and common seen animal/experimental models with organized paragraphs from literatures.

What diseases are associated with Gossypol?

Gossypol is suspected in Severe Combined Immunodeficiency, Aortic Valve Insufficiency, PARKINSON DISEASE, LATE-ONSET, Infertility, CLEFT LIP, CONGENITAL HEALED, Pulmonary Fibrosis and other diseases in descending order of the highest number of associated sentences.

Related references are mostly published in these journals:

Disease Cross reference Weighted score Related literature
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Possible diseases from mapped MeSH terms on references

We collected disease MeSH terms mapped to the references associated with Gossypol

MeSH term MeSH ID Detail
Myxosarcoma D009236 1 associated lipids
Darier Disease D007644 2 associated lipids
Leukemia, Biphenotypic, Acute D015456 2 associated lipids
Carcinoma, Mucoepidermoid D018277 3 associated lipids
Retinal Neoplasms D019572 3 associated lipids
Prostatic Neoplasms, Castration-Resistant D064129 3 associated lipids
Genital Neoplasms, Male D005834 3 associated lipids
Hematologic Neoplasms D019337 4 associated lipids
Trypanosomiasis, African D014353 5 associated lipids
Infertility, Female D007247 5 associated lipids
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PubChem Associated disorders and diseases

What pathways are associated with Gossypol

Lipid pathways are not clear in current pathway databases. We organized associated pathways with Gossypol through full-text articles, including metabolic pathways or pathways of biological mechanisms.

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Pathway name Related literatures
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PubChem Biomolecular Interactions and Pathways

Link to PubChem Biomolecular Interactions and Pathways

What cellular locations are associated with Gossypol?

Related references are published most in these journals:

Location Cross reference Weighted score Related literatures
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What functions are associated with Gossypol?


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Function Cross reference Weighted score Related literatures

What lipids are associated with Gossypol?

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Lipid concept Cross reference Weighted score Related literatures
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What genes are associated with Gossypol?

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Gene Cross reference Weighted score Related literatures

What common seen animal models are associated with Gossypol?

Xenograft Model

Xenograft Model are used in the study 'Gossypol induces apoptosis by activating p53 in prostate cancer cells and prostate tumor-initiating cells.' (Volate SR et al., 2010), Xenograft Model are used in the study 'Sorafenib sensitizes (-)-gossypol-induced growth suppression in androgen-independent prostate cancer cells via Mcl-1 inhibition and Bak activation.' (Lian J et al., 2012), Xenograft Model are used in the study 'Natural BH3 mimetic (-)-gossypol chemosensitizes human prostate cancer via Bcl-xL inhibition accompanied by increase of Puma and Noxa.' (Meng Y et al., 2008), Xenograft Model are used in the study '(-)-Gossypol suppresses the growth of human prostate cancer xenografts via modulating VEGF signaling-mediated angiogenesis.' (Pang X et al., 2011) and Xenograft Model are used in the study 'Gossypol induces death receptor-5 through activation of the ROS-ERK-CHOP pathway and sensitizes colon cancer cells to TRAIL.' (Sung B et al., 2010).

Transgenic Model

Transgenic Model are used in the study 'Bcl-2 antagonist apogossypol (NSC736630) displays single-agent activity in Bcl-2-transgenic mice and has superior efficacy with less toxicity compared with gossypol (NSC19048).' (Kitada S et al., 2008).

Related references are published most in these journals:

Model Cross reference Weighted score Related literatures
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NCBI Entrez Crosslinks

All references with Gossypol

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Per page 10 20 50 100 | Total 1511
Authors Title Published Journal PubMed Link
Bauer JA et al. Reversal of cisplatin resistance with a BH3 mimetic, (-)-gossypol, in head and neck cancer cells: role of wild-type p53 and Bcl-xL. 2005 Mol. Cancer Ther. pmid:16020667
Mohammad RM et al. Preclinical studies of a nonpeptidic small-molecule inhibitor of Bcl-2 and Bcl-X(L) [(-)-gossypol] against diffuse large cell lymphoma. 2005 Mol. Cancer Ther. pmid:15657349
Oliver CL et al. (-)-Gossypol acts directly on the mitochondria to overcome Bcl-2- and Bcl-X(L)-mediated apoptosis resistance. 2005 Mol. Cancer Ther. pmid:15657350
Xu L et al. (-)-Gossypol enhances response to radiation therapy and results in tumor regression of human prostate cancer. 2005 Mol. Cancer Ther. pmid:15713891
Billard C Development of Noxa-like BH3 mimetics for apoptosis-based therapeutic strategy in chronic lymphocytic leukemia. 2012 Mol. Cancer Res. pmid:22466256
Voss V et al. The pan-Bcl-2 inhibitor (-)-gossypol triggers autophagic cell death in malignant glioma. 2010 Mol. Cancer Res. pmid:20587533
Amm HM et al. Mechanisms of drug sensitization to TRA-8, an agonistic death receptor 5 antibody, involve modulation of the intrinsic apoptotic pathway in human breast cancer cells. 2011 Mol. Cancer Res. pmid:21357440
Arnold AA et al. Preclinical studies of Apogossypolone: a new nonpeptidic pan small-molecule inhibitor of Bcl-2, Bcl-XL and Mcl-1 proteins in Follicular Small Cleaved Cell Lymphoma model. 2008 Mol. Cancer pmid:18275607
Cengiz E et al. Overcoming drug resistance in hormone- and drug-refractory prostate cancer cell line, PC-3 by docetaxel and gossypol combination. 2010 Mol. Biol. Rep. pmid:19288219
Karaca B et al. Combination of AT-101/cisplatin overcomes chemoresistance by inducing apoptosis and modulating epigenetics in human ovarian cancer cells. 2013 Mol. Biol. Rep. pmid:23269627
Bork S et al. Identification of Babesia bovis L-lactate dehydrogenase as a potential chemotherapeutical target against bovine babesiosis. 2004 Mol. Biochem. Parasitol. pmid:15478796
Conners R et al. Mapping the binding site for gossypol-like inhibitors of Plasmodium falciparum lactate dehydrogenase. 2005 Mol. Biochem. Parasitol. pmid:15978953
Gomez MS et al. Substrate and cofactor specificity and selective inhibition of lactate dehydrogenase from the malarial parasite P. falciparum. 1997 Mol. Biochem. Parasitol. pmid:9497046
Dando C et al. The kinetic properties and sensitivities to inhibitors of lactate dehydrogenases (LDH1 and LDH2) from Toxoplasma gondii: comparisons with pLDH from Plasmodium falciparum. 2001 Mol. Biochem. Parasitol. pmid:11704270
Lan L et al. Natural product (-)-gossypol inhibits colon cancer cell growth by targeting RNA-binding protein Musashi-1. 2015 Mol Oncol pmid:25933687
Baoleri X et al. Combination of L-gossypol and low-concentration doxorubicin induces apoptosis in human synovial sarcoma cells. 2015 Mol Med Rep pmid:26238307
Zhan W et al. Inhibitory activity of apogossypol in human prostate cancer in vitro and in vivo. 2015 Mol Med Rep pmid:25672487
Zhang X et al. Apogossypolone inhibits the proliferation of LNCaP cells in vitro and in vivo. 2014 Mol Med Rep pmid:25060748
Wang J et al. Gossypol induces apoptosis in ovarian cancer cells through oxidative stress. 2013 Mol Biosyst pmid:23532321
Costantino A et al. Current status and future perspectives in male contraception. 2007 Minerva Ginecol pmid:17576406
Hadley MA and Burgos MH Gossypol injected in the rat epididymal fat pad inhibits epididymal sperm motility. 1986 Microsc Electron Biol Celular pmid:3587061
Makkar HP et al. Plant secondary metabolites. 2007 Methods Mol. Biol. pmid:19238775
Ansari N et al. Quantitative 3D cell-based assay performed with cellular spheroids and fluorescence microscopy. 2013 Methods Cell Biol. pmid:23317907
Blackstaffe L et al. Cytotoxicity of gossypol enantiomers and its quinone metabolite gossypolone in melanoma cell lines. 1997 Melanoma Res. pmid:9429219
Semon B Dietary intake of cottonseed toxins is hypothesized to be a partial cause of Alzheimer's disorder. 2012 Med. Hypotheses pmid:22136946
Cheng CC A common structural pattern among many biologically active compounds of natural and synthetic origin. 1986 Med. Hypotheses pmid:3090407
Yurekli B et al. Can gossypol be a hope for transsexual patients (male to female) before sex reassignment surgery? Just for adjusting the body to mind. 2009 Med. Hypotheses pmid:19647947
Harper MJ Fertility control. 1982 Oct-Dec Med Res Rev pmid:6757597
Przybylski P et al. CP/MAS spectroscopy in the determination of the tautomeric forms of gossypol, its Schiff bases and hydrazones in the solid state. 2008 Magn Reson Chem pmid:18338327
That QT et al. Schiff bases of gossypol: an NMR and DFT study. 2005 Magn Reson Chem pmid:15678567
Abou-Donia MB et al. Metabolic fate of gossypol: the metabolism of 14C-gossypol in rats. 1970 Lipids pmid:5484207
Shandilya LN and Clarkson TB Hypolipidemic effects of gossypol in cynomolgus monkeys (Macaca fascicularis). 1982 Lipids pmid:6952061
Posinovec J [Gossypol - the newest agent for the prevention of male fertility]. 1983 Lijec Vjesn pmid:6888153
Abou-Donia MB and Dieckert JW Gossypol: uncoupling of respiratory chain and oxidative phosphorylation. 1974 Life Sci. pmid:4277086
Lin YC et al. Transfer of 3H-gossypol to neonatal rats via milk of nursing dams. 1992 Life Sci. pmid:1435075
Gilbert NE et al. Antiproliferative activity of gossypol and gossypolone on human breast cancer cells. 1995 Life Sci. pmid:7596222
Wang X et al. Cytotoxic effect of gossypol on colon carcinoma cells. 2000 Life Sci. pmid:11105982
Gu Y et al. Inhibitory effect of gossypol on human chorionic gonadotropin (hCG)-induced progesterone secretion in cultured bovine luteal cells. 1990 Life Sci. pmid:2168511
Benz CC et al. Gossypol effects on endothelial cells and tumor blood flow. 1991 Life Sci. pmid:1875793
Zhang M et al. Gossypol induces apoptosis in human PC-3 prostate cancer cells by modulating caspase-dependent and caspase-independent cell death pathways. 2007 Life Sci. pmid:17156797
Lin YC et al. Binding of 3H-gossypol in organelles of cultured bovine luteal cells. 1992 Life Sci. pmid:1734162
Ye YX et al. Modification of the positive inotropic effects of catecholamines, cardiac glycosides and Ca2+ by the orally active male contraceptive, gossypol, in isolated guinea-pig heart. 1989 Life Sci. pmid:2557505
Lin YC et al. Inhibition of in vitro fertilization and early embryonic development in hamsters by gossypol. 1994 Life Sci. pmid:8090055
Hu YF et al. Gossypol inhibits basal and estrogen-stimulated DNA synthesis in human breast carcinoma cells. 1993 Life Sci. pmid:8255144
Lin YC et al. Gossypol in female fertility control: ovum implantation and early pregnancy inhibited in rats. 1985 Life Sci. pmid:4010468
Jang GH and Lee M BH3-mimetic gossypol-induced autophagic cell death in mutant BRAF melanoma cells with high expression of p21Cip¹.). 2014 Life Sci. pmid:24625733
Soderquist R et al. Gossypol overcomes stroma-mediated resistance to the BCL2 inhibitor ABT-737 in chronic lymphocytic leukemia cells ex vivo. 2013 Leukemia pmid:23640104
Meng Y et al. (-)Gossypol and its combination with imatinib induce apoptosis in human chronic myeloid leukemic cells. 2007 Leuk. Lymphoma pmid:17926190
Balakrishnan K et al. Bax and Bak are required for apogossypolone, a BH3-mimetic, induced apoptosis in chronic lymphocytic leukemia cells. 2013 Leuk. Lymphoma pmid:22866921
Ni Z et al. Natural Bcl-2 inhibitor (-)- gossypol induces protective autophagy via reactive oxygen species-high mobility group box 1 pathway in Burkitt lymphoma. 2013 Leuk. Lymphoma pmid:23398207
Anderson MA et al. BH3 mimetic therapy: an emerging and promising approach to treating chronic lymphocytic leukemia. 2013 Leuk. Lymphoma pmid:23339446
Mellon JE et al. Inhibitory effects of gossypol-related compounds on growth of Aspergillus flavus. 2011 Lett. Appl. Microbiol. pmid:21291481
Mellon JE et al. Growth inhibitory effects of gossypol and related compounds on fungal cotton root pathogens. 2014 Lett. Appl. Microbiol. pmid:24713043
Susman E Cottonseed-oil byproduct as anticancer radiation sensitiser. 2004 Lancet Oncol. pmid:15536689
Gossypol prospects. 1984 Lancet pmid:6144835
Soufir JC et al. Epididymal effects of gossypol. 1984 Lancet pmid:6145995
Pösö H et al. Gossypol, a powerful inhibitor of human spermatozoal metabolism. 1980 Lancet pmid:6103251
Deng S et al. Gossypol acetic acid induces apoptosis in RAW264.7 cells via a caspase-dependent mitochondrial signaling pathway. 2013 J. Vet. Sci. pmid:23820203
Uzal FA et al. Gossypol toxicosis in a dog consequent to ingestion of cottonseed bedding. 2005 J. Vet. Diagn. Invest. pmid:16475530
Dale GL and Friese P Bax activators potentiate coated-platelet formation. 2006 J. Thromb. Haemost. pmid:16970802
Yeow WS et al. Gossypol, a phytochemical with BH3-mimetic property, sensitizes cultured thoracic cancer cells to Apo2 ligand/tumor necrosis factor-related apoptosis-inducing ligand. 2006 J. Thorac. Cardiovasc. Surg. pmid:17140955
Kilic A et al. Efficacy of signal pathway inhibitors alone and in combination with Cisplatin varies between human non-small cell lung cancer lines. 2009 J. Surg. Res. pmid:19084241
Druez D et al. Effect of gossypol on the morphology, motility and metabolism of a flagellated protist, Dunaliella bioculata. 1989 J. Submicrosc. Cytol. Pathol. pmid:2752364
Gu Y et al. Gossypolone suppresses progesterone synthesis in bovine luteal cells. 1991 J. Steroid Biochem. Mol. Biol. pmid:2064986
Sang GW et al. Inhibitory effects of gossypol on corticosteroid 11-beta-hydroxysteroid dehydrogenase from guinea pig kidney: a possible mechanism for causing hypokalemia. 1991 J. Steroid Biochem. Mol. Biol. pmid:1888675
Cuéllar A et al. Cholesterol side-chain cleavage and 11 beta-hydroxylation are inhibited by gossypol in adrenal cortex mitochondria. 1990 J. Steroid Biochem. Mol. Biol. pmid:2278843
Chen BB et al. The (+)- and (-)-gossypols potently inhibit human and rat 11beta-hydroxysteroid dehydrogenase type 2. 2009 J. Steroid Biochem. Mol. Biol. pmid:19150652
Hu GX et al. The (+)- and (-)-gossypols potently inhibit both 3beta-hydroxysteroid dehydrogenase and 17beta-hydroxysteroid dehydrogenase 3 in human and rat testes. 2009 J. Steroid Biochem. Mol. Biol. pmid:19429456
Pearce S et al. Site of gossypol inhibition of steroidogenesis in purified mouse Leydig cells. 1986 J. Steroid Biochem. pmid:3025516
Damaty SM and Hudson BJ Preparation of low-gossypol cottonseed flour. 1975 J. Sci. Food Agric. pmid:1172995
Yang X et al. Identification and proteomic analysis of a novel gossypol-degrading fungal strain. 2012 J. Sci. Food Agric. pmid:22002592
Den Boer PJ and Grootegoed JA Differential effects of (+)- and (-)-gossypol enantiomers on LDH-C4 activity of hamster spermatogenic epithelium in vitro. 1988 J. Reprod. Fertil. pmid:3411560
Yang YQ and Wu XY Antifertility mechanisms of gossypol acetic acid in female rats. 1987 J. Reprod. Fertil. pmid:3656277
Soufir JC et al. Gossypol-induced modifications in the microenvironment of rat epididymal spermatozoa. 1989 J. Reprod. Fertil. pmid:2760873
Hunt S and Mittwoch U Effects of gossypol on sperm counts in two inbred strains of mice. 1984 J. Reprod. Fertil. pmid:6694149
Stephens DT et al. Mechanism of inhibition by gossypol of glycolysis and motility of monkey spermatozoa in vitro. 1983 J. Reprod. Fertil. pmid:6631812
Morris ID et al. Inhibition of testicular LDH-X from laboratory animals and man by gossypol and its isomers. 1986 J. Reprod. Fertil. pmid:3735252
Wang JM et al. Differential binding of (+) and (-) gossypol to plasma protein and their entry into rat testis. 1992 J. Reprod. Fertil. pmid:1625243
Mohan J et al. Studies on antifertility effects of gossypol acetic acid in domestic cocks. 1989 J. Reprod. Fertil. pmid:2536813
Den Boer PJ and Grootegoed JA Mechanism of action of (-)gossypol on ATP production in isolated hamster spermatids. 1988 J. Reprod. Fertil. pmid:3411559
Wichmann K et al. Effect of gossypol on the motility and metabolism of human spermatozoa. 1983 J. Reprod. Fertil. pmid:6411909
Wong YC and Tam CC A structural and cytochemical study of the effects of gossypol on the epithelial cells of the guinea-pig seminal vesicle. 1988 J. Reprod. Fertil. pmid:3199385
Wang JM et al. Effect of gossypol on testicular blood flow and testosterone production in rats. 1984 J. Reprod. Fertil. pmid:6726673
Blanco A et al. Effect of gossypol upon motility and ultrastructure of Trypanosoma cruzi. 1983 J. Protozool. pmid:6363678
Rovai LE et al. Effect of gossypol on trypomastigotes and amastigotes of Trypanosoma cruzi. 1990 Jul-Aug J. Protozool. pmid:2258832
Neild TO et al. Vasodilatation of arterioles by acetylcholine released from single neurones in the guinea-pig submucosal plexus. 1990 J. Physiol. (Lond.) pmid:2324984
Haspel HC et al. Effect of gossypol on erythrocyte membrane function: specific inhibition of inorganic anion exchange and interaction with band 3. 1985 J. Pharmacol. Exp. Ther. pmid:4032282
Haspel HC et al. Cytocidal effect of gossypol on cultured murine erythroleukemia cells is prevented by serum protein. 1984 J. Pharmacol. Exp. Ther. pmid:6584595
Förstermann U et al. Inhibitors of acyl-coenzyme A:lysolecithin acyltransferase activate the production of endothelium-derived vascular relaxing factor. 1986 J. Pharmacol. Exp. Ther. pmid:3487639
Förstermann U et al. Endothelium-derived relaxing factor is likely to modulate the tone of resistance arteries in rabbit hindlimb in vivo. 1987 J. Pharmacol. Exp. Ther. pmid:2447263
González-Garza MT et al. Differential effects of the (+)- and (-)-gossypol enantiomers upon Entamoeba histolytica axenic cultures. 1993 J. Pharm. Pharmacol. pmid:8095532
Touvay C et al. Gossypol: a potent inhibitor of PAF-acether- and leukotriene-induced contractions of guinea-pig lung parenchyma strips. 1987 J. Pharm. Pharmacol. pmid:2886603
Le TT et al. Evidence for a trianion intermediate in the metalation of 4-hydroxy-6,7-dimethoxy-8-methyl-2-naphthoic acid. Methodology and application to racemic 5,5'-didesisopropyl-5,5'-dialkylapogossypol derivatives. 2011 J. Org. Chem. pmid:21174400
Matsuo M Preference of female students for "tempe" preparations composed of glandless cottonseed and defatted soybean or corn at various ratios. 2000 J. Nutr. Sci. Vitaminol. pmid:11185660
Braham JE et al. Effect of calcium and gossypol on the performance of swine and on certain enzymes and other blood constituents. 1967 J. Nutr. pmid:6018252
Sharma MP et al. Effects of levels of protein and gossypol, and length of feeding period on the accumulation of gossypol in tissues of swine. 1966 J. Nutr. pmid:5931188
REISER R and FU HC The mechanism of gossypol detoxification by ruminant animals. 1962 J. Nutr. pmid:14491326
Prost J et al. Digestion and absorption rates of [3H]-oleic acid and [14C]-triolein do not differ in rats fed heated (-) and (+) gossypol cottonseed and soybean flours. 1998 J. Nutr. pmid:9808656
Sotelo A et al. Infertility in male rats induced by diets containing whole cottonseed flour. 1982 J. Nutr. pmid:6897076
GRAU CR Protein concentrates as amino acid sources for the chick; corn gluten meal, cottonseed meal and peanut meal. 1946 J. Nutr. pmid:20999576