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.

Cross Reference

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
Loading... please refresh the page if content is not showing up.

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
Hematologic Neoplasms D019337 4 associated lipids
Darier Disease D007644 2 associated lipids
Endometrial Neoplasms D016889 30 associated lipids
Trypanosomiasis, African D014353 5 associated lipids
Retinoblastoma D012175 12 associated lipids
Lymphoma, B-Cell D016393 24 associated lipids
Carcinoma, Mucoepidermoid D018277 3 associated lipids
Lung Injury D055370 14 associated lipids
Retinal Neoplasms D019572 3 associated lipids
Prostatic Neoplasms, Castration-Resistant D064129 3 associated lipids
Per page 10 20 50 100 | Total 52

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.

Related references are published most in these journals:

Pathway name Related literatures
Loading... please refresh the page if content is not showing up.

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
Loading... please refresh the page if content is not showing up.

What functions are associated with Gossypol?


Related references are published most in these journals:

Function Cross reference Weighted score Related literatures

What lipids are associated with Gossypol?

Related references are published most in these journals:

Lipid concept Cross reference Weighted score Related literatures
Loading... please refresh the page if content is not showing up.

What genes are associated with Gossypol?

Related references are published most in these journals:


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
Loading... please refresh the page if content is not showing up.

NCBI Entrez Crosslinks

All references with Gossypol

Download all related citations
Per page 10 20 50 100 | Total 1511
Authors Title Published Journal PubMed Link
Morris ID Gossypol: a male contraceptive with potential? 1986 IRCS J Med Sci pmid:12280996
Wu GP [Gossypol and its related compounds as contraceptive drugs and drugs for gynecological diseases]. 1988 Shengzhi Yu Biyun pmid:12282152
Baram N et al. Inactivation of intestinal brush-border enzymes by gossypol. 1987 Agric. Biol. Chem. pmid:12283503
Bialy G and Alexander NJ Developments in male contraception. 1992 Health Sex pmid:12286189
Yu ZH and Chan HC Gossypol and hypokalemia: a critical review. 1994 Adv Contracept Deliv Syst pmid:12289957
Xiao B and Wang M Birth control techniques in China. 1983 China Popul Newsl pmid:12312957
Zhong CQ [The morphology and formation of micronuclei of blood lymphocytes in man after cessation of gossypol administration]. 1986 Shengzhi Yu Biyun pmid:12314624
Tung DS et al. Effect of long term gossypol treatment on human testicular structure. 1987 Adv Contracept Deliv Syst pmid:12314752
Zhong CQ [Studies on sperm function in man long after cessation of gossypol administration]. 1988 Shengzhi Yu Biyun pmid:12315492
Wang YX and Chen ZX [A possible mechanism of gossypol-induced hypokalemia and its relation to gossypol dose]. 1991 Shengzhi Yu Biyun pmid:12317367
Herndon N Looking for the "male pill". 1992 Netw Res Triangle Park N C pmid:12317724
Yuan JR [Methods of extraction and purification of gossypol]. 1984 Shengzhi Yu Biyun pmid:12339570
Zheng DK et al. Resolution of racemic gossypol. 1985 J. Chem. Soc. Chem. Commun. pmid:12340526
Gonzales-garza MT et al. Cytotoxic effects of gossypol and vitamin E on human and rat lymphocytes and spermatozoa. 1985 Nutr Rep Int pmid:12340733
Goldstein M The future of male birth control. 1986 Plan Parent Rev pmid:12340896
Wang R [Sister chromatid exchanges in gossypol formic acid users after its discontinuation]. 1986 Shengzhi Yu Biyun pmid:12341303
Andrade AT [Information on advances in sciences and technology. Advances in contraceptive technology]. 1993 Bol Cent Biol Reprod pmid:12345521
Velasquez-Pereira J et al. Effects of gossypol from cottonseed meal and dietary vitamin E on the reproductive characteristics of superovulated beef heifers. 2002 J. Anim. Sci. pmid:12350026
Lee KJ and Dabrowski K High-performance liquid chromatographic determination of gossypol and gossypolone enantiomers in fish tissues using simultaneous electrochemical and ultraviolet detectors. 2002 J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. pmid:12361745
Pandey SN and Thejappa N Study on relationship between oil, protein, and gossypol in cottonseed kernels. 1975 J Am Oil Chem Soc pmid:1242138
Puckhaber LS et al. Toxicity of (+)- and (-)-gossypol to the plant pathogen, Rhizoctonia solani. 2002 J. Agric. Food Chem. pmid:12428953
Phillis JW et al. Effects of immunosuppressants, calcineurin inhibition, and blockade of endoplasmic reticulum calcium channels on free fatty acid efflux from the ischemic/reperfused rat cerebral cortex. 2002 Brain Res. pmid:12443975
Le Blanc M et al. An in vitro study of inhibitory activity of gossypol, a cottonseed extract, in human carcinoma cell lines. 2002 Pharmacol. Res. pmid:12457630
Kuhn G et al. Gossypol induces chloride secretion in rat proximal colon. 2002 Eur. J. Pharmacol. pmid:12464365
NarovlianskiÄ­ AN et al. [Effect of interferon inductors on infection induced by hepatitis C virus and activity of mRNA cytokines in cell cultures SW-13 and MT-4]. 2002 Nov-Dec Vopr. Virusol. pmid:12508677
Shi YL et al. Ion-channels in human sperm membrane and contraceptive mechanisms of male antifertility compounds derived from Chinese traditional medicine. 2003 Acta Pharmacol. Sin. pmid:12511225
Risco CA et al. Effects of gossypol from cottonseed on hematological responses and plasma alpha-tocopherol concentration of dairy cows. 2002 J. Dairy Sci. pmid:12512612
Freedman TB et al. Determination of the absolute configuration and solution conformation of gossypol by vibrational circular dichroism. 2003 Chirality pmid:12520512
Tone JN and Jensen DR The accumulation pattern of ingested gossypol in selected organs of the rat. 1976 Experientia pmid:1253913
Keller PA et al. Novel pharmacophore-based methods reveal gossypol as a reverse transcriptase inhibitor. 2003 J. Mol. Graph. Model. pmid:12543135
Shi A et al. [Screening and breeding of highly-effected degrading cotton-phenol strains and study on defoxication technology and conditions]. 1998 Wei Sheng Wu Xue Bao pmid:12549423
Mego M Telomerase inhibitors in anticancer therapy: gossypol as a potential telomerase inhibitor. 2002 Bratisl Lek Listy pmid:12583508
Bai JP et al. Effects of demethylzeylasteral and celastrol on spermatogenic cell Ca2+ channels and progesterone-induced sperm acrosome reaction. 2003 Eur. J. Pharmacol. pmid:12600689
Prieto JG et al. Increasing dietary levels of cracked pima cottonseed increase plasma gossypol but do not influence productive performance of lactating Holstein cows. 2003 J. Dairy Sci. pmid:12613869
Dao VT et al. New thioderivatives of gossypol and gossypolone, as prodrugs of cytotoxic agents. 2003 Bioorg. Med. Chem. pmid:12670651
Vershinina MY et al. Regulation of cytokine mRNAs by interferon and interferon inducers. 2002 Russ. J. Immunol. pmid:12687259
Santos JE et al. Type of cottonseed and level of gossypol in diets of lactating dairy cows: plasma gossypol, health, and reproductive performance. 2003 J. Dairy Sci. pmid:12703626
Dowd MK Preparation of enantiomeric gossypol by crystallization. 2003 Chirality pmid:12774287
Cui GH et al. [Determination of gossypol in cotton root bark by HPLC]. 2002 Zhongguo Zhong Yao Za Zhi pmid:12774395
Zhang M et al. Molecular mechanism of gossypol-induced cell growth inhibition and cell death of HT-29 human colon carcinoma cells. 2003 Biochem. Pharmacol. pmid:12818369
Sagach VF et al. Functional hyperemia of skeletal muscle: role of endothelium. 1992 J. Cardiovasc. Pharmacol. pmid:1282960
Tkachenko MN et al. Involvement of endothelium in vasodilating effects of vintoperol. 1992 J. Cardiovasc. Pharmacol. pmid:1282997
Dowd MK and Stevens ED The gossypol-cyclododecanone (1/2) inclusion complex. 2003 Acta Crystallogr C pmid:12855869
Kawanishi K et al. Aldose reductase inhibitors from the nature. 2003 Curr. Med. Chem. pmid:12871134
Räsänen TL et al. Gossypol activates pancreatic polyamine catabolism in normal rats and induces acute pancreatitis in transgenic rats over-expressing spermidine/spermine N1-acetyltransferase. 2003 Scand. J. Gastroenterol. pmid:12889567
Xue S [A beam of dawn light of study on gossypol as a safe, effective, and reversible male antifertility contraceptive--evaluation of the studies by using low dose gossypol combined with steroid hormone for male contraception]. 2000 Zhongguo Yi Xue Ke Xue Yuan Xue Bao pmid:12903461
Wang L et al. [Combined use of steroid hormone and low dose gossypol for antifertility and its mechanism in rats]. 2000 Zhongguo Yi Xue Ke Xue Yuan Xue Bao pmid:12903462
Cao J et al. [Effect of low dose gossypol treatment on male sperm nuclear basic protein]. 2000 Zhongguo Yi Xue Ke Xue Yuan Xue Bao pmid:12903463
Zaidi R and Hadi SM Complexes involving gossypol, DNA and Cu(II). 1992 Biochem. Int. pmid:1290468
Jo C et al. Irradiation effects on embryotoxicity and oxidative properties of gossypol dissolved in methanol. 2003 Food Chem. Toxicol. pmid:12909266
Zaidi R and Hadi SM Strand scission in DNA by gossypol and Cu(II): role of Cu(I) and oxygen-free radicals. 1992 J. Biochem. Toxicol. pmid:1293310
Wang YH et al. 8-Hydroxy-(+)-delta-cadinene is a precursor to hemigossypol in Gossypium hirsutum. 2003 Phytochemistry pmid:12946420
Adekunle AO et al. Seminal plasma zinc level in users of gossypol. 1999 Mar-Jun Afr J Med Med Sci pmid:12953977
Yurtcu E et al. Apoptotic effect of gossypol on human lymphocytes. 2003 Cell Biol. Int. pmid:12972286
Franklin RB et al. Prolactin stimulates transcription of aspartate aminotransferase in prostate cells. 1992 Mol. Cell. Endocrinol. pmid:1301396
Chang SM et al. [Effect of gossypol on the proliferation of rat prostate cells studies in vivo and in vitro]. 1992 Shi Yan Sheng Wu Xue Bao pmid:1303003
CASTILLON LE et al. Preparation of combination products of gossypol with glycine and dextrose and their toxicity toward mice. 1953 Arch. Biochem. Biophys. pmid:13058367
Udoh P and Patil DR Effects of gossypol acetate on pituitary-adrenal axis in male albino rats. 1992 Contraception pmid:1324828
SMITH HA The pathology of gossypol poisoning. 1957 Mar-Apr Am. J. Pathol. pmid:13402891
González-Garza MT et al. Further studies on the in vitro activity of gossypol as antiamebic agent. 1992 Arch. Med. Res. pmid:1340324
Martínez F The antifertility agent, gossypol, changes several mitochondrial functions in the presence of Mg2+. 1992 Comp. Biochem. Physiol. C, Comp. Pharmacol. Toxicol. pmid:1360378
pmid:13611584
CONKERTON EJ and FRAMPTON VL Reaction of gossypol with free epsilon-amino groups of lysine in proteins. 1959 Arch. Biochem. Biophys. pmid:13637974
Kitada S et al. Discovery, characterization, and structure-activity relationships studies of proapoptotic polyphenols targeting B-cell lymphocyte/leukemia-2 proteins. 2003 J. Med. Chem. pmid:13678404
ADAMS R et al. Gossypol, a pigment of cottonseed. 1960 Chem. Rev. pmid:13681414
Smith C et al. Protection by albumin against the pro-oxidant actions of phenolic dietary components. 1992 Food Chem. Toxicol. pmid:1379971
HEINSTEIN PF et al. Biosynthesis of C-14-labeled gossypol. 1962 J. Biol. Chem. pmid:13906099
Stein RC et al. A preliminary clinical study of gossypol in advanced human cancer. 1992 Cancer Chemother. Pharmacol. pmid:1394805
Rao AG A stoichiometric analysis of bovine serum albumin-gossypol interactions: a fluorescence quenching study. 1992 Indian J. Biochem. Biophys. pmid:1398710
VERMEL EM and KRUGLIAK SA [ANTINEOPLASTIC ACTIVITY OF GOSSYPOL IN EXPERIMENTAL TRANSPLANTED TUMORS]. 1963 Vopr Onkol pmid:14148612
VERMEL EM THE SEARCH FOR ANTITUMOUR SUBSTANCES OF PLANT ORIGIN. 1964 Acta Unio Int Contra Cancrum pmid:14151888
BRESSANI R et al. ALL-VEGETABLE PROTEIN MIXTURES FOR HUMAN FEEDING. XV. STUDIES IN DOGS ON THE ABSORPTION OF GASSYPOL FROM COTTONSEED FLOUR-CONTAINING VEGETABLE PROTEIN MIXTURES. 1964 J. Nutr. pmid:14191421
SMITH FH DETERMINATION OF FREE AND BOUND GOSSYPOL IN SWINE TISSUES. 1965 J Am Oil Chem Soc pmid:14268479
VERMEL EM and KRUGLYAK SA ANTITUMOR ACTIVITY OF GOSSYPOL IN EXPERIMENTS ON TRANSPLANTABLE TUMORS. 1965 Jan-Feb Fed Proc Transl Suppl pmid:14275562
DANKE RJ and TILLMAN AD EFFECT OF GOSSYPOL AND HEXAHOMOSERINE ON PERFORMANCE OF RATS FED PURIFIED DIETS WITH AND WITHOUT LYSINE. 1965 J. Anim. Sci. pmid:14296177
Risco CA et al. Effect of graded concentrations of gossypol on calf performance: toxicological and pathological considerations. 1992 J. Dairy Sci. pmid:1430484
CASADY RB et al. FURTHER STUDIES OF DEGOSSYPOLIZED COTTONSEED MEAL AS A SOURCE OF PLANT PROTEIN IN RABBIT FEEDS. 1965 J Am Oil Chem Soc pmid:14328364
Lin YC et al. Transfer of 3H-gossypol to neonatal rats via milk of nursing dams. 1992 Life Sci. pmid:1435075
LYMAN CM et al. Reactions of proteins with gossypol. 1959 Arch. Biochem. Biophys. pmid:14419129
Tres LL et al. Permeable collagen-glycosaminoglycan cross-linked copolymers for the study of biological responses of cocultured Sertoli and spermatogenic cells. 1992 Jul-Sep Cell Biol. Toxicol. pmid:1446259
REISER R and FU HC The mechanism of gossypol detoxification by ruminant animals. 1962 J. Nutr. pmid:14491326
Aneja R et al. Modulatory influence of tin-protoporphyrin on gossypol-induced alterations of heme oxygenase activity in male Wistar rats. 2003 Jul-Sep Eur J Drug Metab Pharmacokinet pmid:14527098
Kovacic P Mechanism of drug and toxic actions of gossypol: focus on reactive oxygen species and electron transfer. 2003 Curr. Med. Chem. pmid:14529461
Sheriff DS Effect of gossypol on tissue levels of glutathione and thiobarbituric acid reactive products in rats. 1992 Indian J. Exp. Biol. pmid:1459652
Cheng JS et al. Effect of gossypol on intracellular Ca2+ regulation in human hepatoma cells. 2003 Chin J Physiol pmid:14672280
Abe F et al. Trypanocidal constituents in plants 3. Leaves of Garcinia intermedia and heartwood of Calophyllum brasiliense. 2004 Biol. Pharm. Bull. pmid:14709920
Sabirova FM and Madaminov AA [Anti-inflammatory activity of the novel water soluble gossipol derivative mebavine]. 2003 Nov-Dec Eksp Klin Farmakol pmid:14743712
MARX MH Note of depression of spontaneous running activity by the appetite depressant gossypol in rats. 1950 J Comp Physiol Psychol pmid:14784530
PARHAM AP et al. The influence of solvent extracted and hydraulic processed cottonseed meals upon performance and level of plasma carotene, vitamin A, and fat in the blood of wintering beef cows. 1950 J. Anim. Sci. pmid:14794574
GALLUP WD et al. Comparative effect on vitamin A metabolism in sheep of urea, soybean oil meal and cottonseed meal as sources of protein. 1951 J. Anim. Sci. pmid:14814051
AMBROSE AM and ROBBINS DJ Studies on the chronic oral toxicity of cottonseed meal and cottonseed pigment glands. 1951 J. Nutr. pmid:14851050
HARMS WS and HOLLEY KT Hypoprothrombinemia induced by gossypol. 1951 Proc. Soc. Exp. Biol. Med. pmid:14854026
COTTONSEED meal. 1951 Nutr. Rev. pmid:14863810
Wang X and Plhak LC Monoclonal antibodies for the analysis of gossypol in cottonseed products. 2004 J. Agric. Food Chem. pmid:14969520
Ergun MA et al. Apoptosis and nitric oxide release induced by thalidomide, gossypol and dexamethasone in cultured human chronic myelogenous leukemic K-562 cells. 2004 Cell Biol. Int. pmid:14984751
Przybylski P et al. Schiff base of gossypol with 3,6,9-trioxa-decylamine complexes with monovalent cations studied by mass spectrometry, (1)H-NMR, FTIR, and PM5 semiempirical methods. 2004 Biopolymers pmid:14991665
Jiang J et al. The inhibitory effects of gossypol on human prostate cancer cells-PC3 are associated with transforming growth factor beta1 (TGFbeta1) signal transduction pathway. 2004 Jan-Feb Anticancer Res. pmid:15015581
Aneja R et al. Effect of gossypol in association with chromium protoporphyrin on heme metabolic enzymes. 2004 Artif Cells Blood Substit Immobil Biotechnol pmid:15027808
Hassan ME et al. Reversibility of the reproductive toxicity of gossypol in peripubertal bulls. 2004 Theriogenology pmid:15037004
Fombad RB and Bryant MJ An evaluation of the use of cottonseed cake in the diet of growing pigs. 2004 Trop Anim Health Prod pmid:15080544