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
Protein Deficiency D011488 5 associated lipids
Prostatic Neoplasms D011471 126 associated lipids
Pemphigoid, Bullous D010391 8 associated lipids
Pancreatic Neoplasms D010190 77 associated lipids
Nutrition Disorders D009748 6 associated lipids
Neuroblastoma D009447 66 associated lipids
Neovascularization, Pathologic D009389 39 associated lipids
Neoplasms, Hormone-Dependent D009376 23 associated lipids
Myxosarcoma D009236 1 associated lipids
Melanoma D008545 69 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
Manabe S et al. Zone-specific hepatotoxicity of gossypol in perfused rat liver. 1991 Toxicon pmid:1926180
Makkar HP et al. Plant secondary metabolites. 2007 Methods Mol. Biol. pmid:19238775
Lin J et al. [Effect of apogossypolone on induction apoptosis in multiple myeloma cells and its mechanisms]. 2009 Zhongguo Shi Yan Xue Ye Xue Za Zhi pmid:19236755
Barba-Barajas M et al. Gossypol induced apoptosis of polymorphonuclear leukocytes and monocytes: involvement of mitochondrial pathway and reactive oxygen species. 2009 Immunopharmacol Immunotoxicol pmid:19235535
Kang MH and Reynolds CP Bcl-2 inhibitors: targeting mitochondrial apoptotic pathways in cancer therapy. 2009 Clin. Cancer Res. pmid:19228717
Przybylski P et al. Complexes of heterocyclic aza-derivatives of phytoalexin from cotton plant-gossypol with alkali metal cations and perchlorate anion studied by ESI mass spectrometric method in the positive and negative modes. 2009 J Mass Spectrom pmid:19189269
Majumdar SK et al. Genotoxic effects of gossypol acetic acid on cultured murine erythroleukemia cells. 1991 Environ. Mol. Mutagen. pmid:1915316
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
Stipanovic RD et al. Total and percent atropisomers of gossypol and gossypol-6-methyl ether in seeds from pima cottons and accessions of Gossypium barbadense L. 2009 J. Agric. Food Chem. pmid:19113939
Sheweita SA et al. N-Nitrosodimethylamine changes the expression of glutathione S-transferase in the liver of male mice: The role of antioxidants. 2008 Nov-Dec J. Biochem. Mol. Toxicol. pmid:19111000
Karaca B et al. Profiling of angiogenic cytokines produced by hormone- and drug-refractory prostate cancer cell lines, PC-3 and DU-145 before and after treatment with gossypol. 2008 Eur. Cytokine Netw. pmid:19103523
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
Moore SA et al. Brain microvessel 12-hydroxyeicosatetraenoic acid is the (S) enantiomer and is lipoxygenase derived. 1991 J. Neurochem. pmid:1907312
Chadha S et al. Alterations and reversibility of the effects of gossypol acetic acid on the intestinal uptake of end product nutrients in normal and protein calorie-malnourished male rats. 1991 Ann. Nutr. Metab. pmid:1905512
Stipanovic RD et al. Effect of racemic, (+)- and (-)-gossypol on survival and development of Heliothis virescens larvae. 2008 Environ. Entomol. pmid:19036185
Zhai G et al. A liposomal delivery vehicle for the anticancer agent gossypol. 2008 Sep-Oct Anticancer Res. pmid:19035313
Mi JX et al. Synergistic antitumoral activity and induction of apoptosis by novel pan Bcl-2 proteins inhibitor apogossypolone with adriamycin in human hepatocellular carcinoma. 2008 Acta Pharmacol. Sin. pmid:19026166
Gong YZ et al. Cinnamyl-3,4-dihydroxy-alpha-cyanocinnamate and nordihydroguaiaretic acid inhibit human Kv1.5 currents independently of lipoxygenase. 2008 Eur. J. Pharmacol. pmid:18930721
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
Janssen CO et al. Interaction of kendomycin and semi-synthetic analogues with the anti-apoptotic protein Bcl-xl. 2008 Bioorg. Med. Chem. Lett. pmid:18845435
Macoska JA et al. -(-)Gossypol promotes the apoptosis of bladder cancer cells in vitro. 2008 Nov-Dec Pharmacol. Res. pmid:18840529
Balakrishnan K et al. AT-101 induces apoptosis in CLL B cells and overcomes stromal cell-mediated Mcl-1 induction and drug resistance. 2009 Blood pmid:18836097
Sun J et al. ApoG2 inhibits antiapoptotic Bcl-2 family proteins and induces mitochondria-dependent apoptosis in human lymphoma U937 cells. 2008 Anticancer Drugs pmid:18827561
Tang Y et al. [Progress in small-molecule inhibitors of Bcl-2 family proteins]. 2008 Yao Xue Xue Bao pmid:18819468
Aoyama K [Determination of gossypol in feeds by HPLC]. 2008 Shokuhin Eiseigaku Zasshi pmid:18787315
Wei J et al. Synthesis and evaluation of Apogossypol atropisomers as potential Bcl-xL antagonists. 2009 Cancer Lett. pmid:18782651
Moon DO et al. Gossypol suppresses telomerase activity in human leukemia cells via regulating hTERT. 2008 FEBS Lett. pmid:18775705
Sun Y et al. Apogossypolone, a nonpeptidic small molecule inhibitor targeting Bcl-2 family proteins, effectively inhibits growth of diffuse large cell lymphoma cells in vitro and in vivo. 2008 Cancer Biol. Ther. pmid:18769131
Azmi AS and Mohammad RM Non-peptidic small molecule inhibitors against Bcl-2 for cancer therapy. 2009 J. Cell. Physiol. pmid:18767026
Etxebarria A et al. Regulation of antiapoptotic MCL-1 function by gossypol: mechanistic insights from in vitro reconstituted systems. 2008 Biochem. Pharmacol. pmid:18762177
Benz CC et al. Gossypol effects on endothelial cells and tumor blood flow. 1991 Life Sci. pmid:1875793
Zhou DR et al. Gossypol repressed the gap junctional intercellular communication between Sertoli cells by decreasing the expression of Connexin43. 2008 Toxicol In Vitro pmid:18706992
Przybylski P et al. Molecular structures and stability constants of gossypol and its aza-derivative complexes with silver(I) cations studied by potentiometric, ESI MS, NMR, and AM1d semiempirical methods. 2008 J Phys Chem A pmid:18698745
Pankajakshy A and Madambath I Spermatotoxic effects of Cananga odorata (Lam): a comparison with gossypol. 2009 Fertil. Steril. pmid:18692834
Villaseñor M et al. Gossypol disrupts embryo development in heifers. 2008 J. Dairy Sci. pmid:18650278
Meng Y et al. Natural BH3 mimetic (-)-gossypol chemosensitizes human prostate cancer via Bcl-xL inhibition accompanied by increase of Puma and Noxa. 2008 Mol. Cancer Ther. pmid:18645028
Liu J et al. Stereoselective coupling of hemigossypol to form (+)-gossypol in moco cotton is mediated by a dirigent protein. 2008 Phytochemistry pmid:18639908
Marzo I and Naval J Bcl-2 family members as molecular targets in cancer therapy. 2008 Biochem. Pharmacol. pmid:18638457
Trischitta F and Faggio C Gossypol affects ion transport in the isolated intestine of the seawater adapted eel, Anguilla anguilla. 2008 Comp. Biochem. Physiol., Part A Mol. Integr. Physiol. pmid:18606239
Politzer WM Long-term clinical remission of a patient with chronic lymphocytic leukemia using alternative treatment option: cottonseed oil (gossypol). 2008 Phytomedicine pmid:18573644
Balakrishnan K et al. Gossypol, a BH3 mimetic, induces apoptosis in chronic lymphocytic leukemia cells. 2008 Blood pmid:18566329
Boonsri S et al. Cytotoxic and antibacterial sesquiterpenes from Thespesia populnea. 2008 J. Nat. Prod. pmid:18553924
Messiha FS Behavioral and metabolic interaction between gossypol and ethanol. 1991 Toxicol. Lett. pmid:1853362
Johnson PW New targets for lymphoma treatment. 2008 Ann. Oncol. pmid:18519406
Wang X et al. Bioactivities of gossypol, 6-methoxygossypol, and 6,6'-dimethoxygossypol. 2008 J. Agric. Food Chem. pmid:18517219
Lu H and Liu GT Effect of dibenzo[a,c]cyclooctene lignans isolated from Fructus schizandrae on lipid peroxidation and anti-oxidative enzyme activity. 1991 Chem. Biol. Interact. pmid:1849050
Lv G et al. [The effect of gossypol, praziquantel and artemether on recombinant lactate dehydrogenase from Schistosoma japonicum]. 2007 Zhongguo Ji Sheng Chong Xue Yu Ji Sheng Chong Bing Za Zhi pmid:18441994
Dowd MK and Pelitire SM HPLC preparation of the chiral forms of 6-methoxy-gossypol and 6,6'-dimethoxy-gossypol. 2008 J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. pmid:18407810
Sikora MJ et al. Anti-oxidant treatment enhances anti-tumor cytotoxicity of (-)-gossypol. 2008 Cancer Biol. Ther. pmid:18376141
Gao F et al. Interactive effects of elevated CO2 and cotton cultivar on tri-trophic interaction of Gossypium hirsutum, Aphis gossyppii, and Propylaea japonica. 2008 Environ. Entomol. pmid:18348793
Kline MP et al. R-(-)-gossypol (AT-101) activates programmed cell death in multiple myeloma cells. 2008 Exp. Hematol. pmid:18346839
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
Mazumder B et al. Effect of chlorpromazine and gossypol on Ca(2+)-ATPase activity in the microsomal membranes of rat testes. 1991 Indian J. Biochem. Biophys. pmid:1831790
Moon DO et al. Gossypol suppresses NF-kappaB activity and NF-kappaB-related gene expression in human leukemia U937 cells. 2008 Cancer Lett. pmid:18314260
Zha SW et al. [Male antifertility drugs and cell apoptosis]. 2008 Zhonghua Nan Ke Xue pmid:18297819
Paoluzzi L et al. Targeting Bcl-2 family members with the BH3 mimetic AT-101 markedly enhances the therapeutic effects of chemotherapeutic agents in in vitro and in vivo models of B-cell lymphoma. 2008 Blood pmid:18292288
Sprogøe K et al. Combining HPLC-PDA-MS-SPE-NMR with circular dichroism for complete natural product characterization in crude extracts: levorotatory gossypol in Thespesia danis. 2008 J. Nat. Prod. pmid:18290629
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
Rodríguez-Enríquez S et al. Energy metabolism transition in multi-cellular human tumor spheroids. 2008 J. Cell. Physiol. pmid:18264981
Tang G et al. Acylpyrogallols as inhibitors of antiapoptotic Bcl-2 proteins. 2008 J. Med. Chem. pmid:18237106
Woolley RJ Contraception--a look forward, Part II: Mifepristone and gossypol. 1991 Mar-Apr J Am Board Fam Pract pmid:1823560
Brozic P et al. Inhibitors of 17beta-hydroxysteroid dehydrogenase type 1. 2008 Curr. Med. Chem. pmid:18220769
Kitada S et al. 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). 2008 Blood pmid:18202226
Przybylski P et al. EI MS and ESI MS studies of the bisesquiterpene from cotton seeds: Gossypol and its Aza-derivatives. 2008 J Mass Spectrom pmid:18200654
Akinola OB et al. Spermatoprotective activity of the leaf extract of Psidium guajava Linn. 2007 Niger Postgrad Med J pmid:18163132
HOFFPAUIR CL and GUTHRIE JD The use of aminized and phosphorylated cotton fabrics as ion exchange materials in the preparation of oil seed proteins. 1949 J. Biol. Chem. pmid:18112104
Sagach VF and Kindybaliuk AM [The role of the endothelium in the development of functional hyperemia of the skeletal muscles]. 1991 Biull Eksp Biol Med pmid:1810472
Loberg RD et al. In vivo evaluation of AT-101 (R-(-)-gossypol acetic acid) in androgen-independent growth of VCaP prostate cancer cells in combination with surgical castration. 2007 Neoplasia pmid:18084610
Murohara T et al. Age related attenuation of the endothelium dependent relaxation to noradrenaline in isolated pig coronary arteries. 1991 Cardiovasc. Res. pmid:1806231
Royer RE et al. Inhibition of human immunodeficiency virus type I replication by derivatives of gossypol. 1991 Pharmacol. Res. pmid:1805194
Turco E et al. The in vitro effect of gossypol and its interaction with salts on conidial germination and viability of Fusarium oxysporum sp. vasinfectum isolates. 2007 J. Appl. Microbiol. pmid:18045422
Mao YB et al. Silencing a cotton bollworm P450 monooxygenase gene by plant-mediated RNAi impairs larval tolerance of gossypol. 2007 Nat. Biotechnol. pmid:17982444
Shaaban WF et al. Reproductive toxicologic effects of gossypol on male rabbits: biochemical, enzymatic, and electrolytic properties of seminal plasma. 2008 Fertil. Steril. pmid:17953964
Li ZM et al. Synergistic cytotoxicity of Bcl-xL inhibitor, gossypol and chemotherapeutic agents in non-Hodgkin's lymphoma cells. 2008 Cancer Biol. Ther. pmid:17938578
Meng Y et al. (-)Gossypol and its combination with imatinib induce apoptosis in human chronic myeloid leukemic cells. 2007 Leuk. Lymphoma pmid:17926190
Gonzalez-Garza T et al. In vitro evaluation of gossypol as potential antiamoebic drug. 1991 Proc. West. Pharmacol. Soc. pmid:1788315
Nikokyris P et al. Effects of gossypol content of cottonseed cake on blood constituents in growing-fattening lambs. 1991 J. Dairy Sci. pmid:1787198
Botsoglou NA High-performance liquid chromatographic method for the determination of free gossypol in chicken liver. 1991 J. Chromatogr. pmid:1783672
Thomas KD et al. Effects of an aqueous extract of cotton seed (Gossypium barbadense Linn.) on adult male rats. 1991 Adv Contracept pmid:1776560
Eagle E Chronic Toxicity of Gossypol. 1949 Science pmid:17742136
Jinsart W et al. Inhibition of wheat embryo calcium-dependent protein kinase and avian myosin light chain kinase by flavonoids and related compounds. 1991 Biol. Chem. Hoppe-Seyler pmid:1772594
Lin YC et al. Gossypol pharmacokinetics in mid-lactation Brown Swiss dairy cows. 1991 Vet. Res. Commun. pmid:1771762
Gerasimidis K et al. Preparation of an edible cottonseed protein concentrate and evaluation of its functional properties. 2007 Int J Food Sci Nutr pmid:17710592
Choi SR et al. Design, synthesis, and biological evaluation of Plasmodium falciparum lactate dehydrogenase inhibitors. 2007 J. Med. Chem. pmid:17636950
Bertrand V and Belleville J Effect of refeeding diets containing cottonseed flour with traces of gossypol on rat liver and testis. 1991 Br. J. Nutr. pmid:1760445
Ko CH et al. Gossypol reduction of tumor growth through ROS-dependent mitochondria pathway in human colorectal carcinoma cells. 2007 Int. J. Cancer pmid:17597109
Costantino A et al. Current status and future perspectives in male contraception. 2007 Minerva Ginecol pmid:17576406
Tang G et al. Structure-based design of flavonoid compounds as a new class of small-molecule inhibitors of the anti-apoptotic Bcl-2 proteins. 2007 J. Med. Chem. pmid:17552510
Wolter KG et al. Therapeutic window for melanoma treatment provided by selective effects of the proteasome on Bcl-2 proteins. 2007 Cell Death Differ. pmid:17541428
Kasten-Pisula U et al. Radiosensitization of tumour cell lines by the polyphenol Gossypol results from depressed double-strand break repair and not from enhanced apoptosis. 2007 Radiother Oncol pmid:17521756
Orth RG et al. Determining larval host plant use by a polyphagous lepidopteran through analysis of adult moths for plant secondary metabolites. 2007 J. Chem. Ecol. pmid:17492366
Badawy SZ et al. Gossypol inhibits proliferation of endometrioma cells in culture. 2007 Asian J. Androl. pmid:17486280
Thomas M et al. Effects of gossypol on the cell cycle phases in T-47D human breast cancer cells. 1991 Jul-Aug Anticancer Res. pmid:1746904
Cui G et al. Gossypol with methyltestosterone and ethinylestradiol male does not affect rat spermatogonial stem cell differentiation. 2007 Mar-Apr Arch. Androl. pmid:17453689
Feng BY et al. A high-throughput screen for aggregation-based inhibition in a large compound library. 2007 J. Med. Chem. pmid:17447748
Barraza ML et al. Iron sulfate and feed pelleting to detoxify free gossypol in cottonseed diets for dairy cattle. 1991 J. Dairy Sci. pmid:1744276
pmid:17438551
Jia L et al. Comparison of pharmacokinetic and metabolic profiling among gossypol, apogossypol and apogossypol hexaacetate. 2008 Cancer Chemother. Pharmacol. pmid:17356822
Leyman A et al. The absence of expression of the three isoenzymes of the inositol 1,4,5-trisphosphate 3-kinase does not prevent the formation of inositol pentakisphosphate and hexakisphosphate in mouse embryonic fibroblasts. 2007 Cell. Signal. pmid:17355905
Ye W et al. Modulation of multidrug resistance gene expression in human breast cancer cells by (-)-gossypol-enriched cottonseed oil. 2007 Jan-Feb Anticancer Res. pmid:17352222