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.
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.
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.
Disease | Cross reference | Weighted score | Related literature |
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We collected disease MeSH terms mapped to the references 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.
Pathway name | Related literatures |
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Associated locations are in red color. Not associated locations are in black.
Location | Cross reference | Weighted score | Related literatures |
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Function | Cross reference | Weighted score | Related literatures |
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Lipid concept | Cross reference | Weighted score | Related literatures |
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Gene | Cross reference | Weighted score | Related literatures |
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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 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).
Model | Cross reference | Weighted score | Related literatures |
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Authors | Title | Published | Journal | PubMed Link |
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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 |
RodrÃguez-EnrÃquez 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 |