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
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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
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
Leukemia, Biphenotypic, Acute D015456 2 associated lipids
Myxosarcoma D009236 1 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?

Related references are published most in these journals:

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
Braham JE et al. Effect of gossypol on the iron-binding capacity of serum in swine. 1967 J. Nutr. pmid:6052995
Roehm JN et al. Accumulation and elimination of dietary gossypol in the organs of rainbow trout. 1967 J. Nutr. pmid:6054742
Alford BB and Onley K The minimum cottonseed protein required for nitrogen balance in women. 1978 J. Nutr. pmid:580097
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
Abou-Donia MB and Dieckert JW Urinary and biliary excretion of 14C-gossypol in swine. 1974 J. Nutr. pmid:4830281
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
Smith FH and Clawson AJ Effect of diet on accumulation of gossypol in the organs of swine. 1965 J. Nutr. pmid:5892976
Danke RJ and Tillman AD Effect of free gossypol and supplemental dietary iron on blood constituents of rats. 1965 J. Nutr. pmid:5897732
Clawson AJ and Smith FH Effect of dietary iron on gossypol toxicity and on residues of gossypil in porcine liver. 1966 J. Nutr. pmid:5950205
Skutches CL and Smith FH Effect of phenobarbital on the level of gossypol in the liver and the effect of gossypol and phenobarbital on liver microsomal O-demethylation and lipid peroxidation activities in the rat. 1974 J. Nutr. pmid:4430931
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
Skutches CL et al. Effect of intravenous gossypol injection on iron ultilization in swine. 1973 J. Nutr. pmid:4705271
Herman DL and Smith FH Effect of bound gossypol on the absorption of iron by rats. 1973 J. Nutr. pmid:4705274
GRAU CR Protein concentrates as amino acid sources for the chick; corn gluten meal, cottonseed meal and peanut meal. 1946 J. Nutr. pmid:20999576
Coyle T et al. In vitro and in vivo cytotoxicity of gossypol against central nervous system tumor cell lines. 1994 J. Neurooncol. pmid:7815102
Bushunow P et al. Gossypol treatment of recurrent adult malignant gliomas. 1999 J. Neurooncol. pmid:10448875
Chatterjee TK and Bhatnagar RK Ca2(+)-dependent, ATP-induced conversion of the [3H]hemicholinium-3 binding sites from high- to low-affinity states in rat striatum: effect of protein kinase inhibitors on this affinity conversion and synaptosomal choline transport. 1990 J. Neurochem. pmid:2324736
Moore SA et al. Brain microvessel 12-hydroxyeicosatetraenoic acid is the (S) enantiomer and is lipoxygenase derived. 1991 J. Neurochem. pmid:1907312
Sinnhuber RO et al. Dietary factors and hepatoma in rainbow trout (Salmo gairdneri). II. Cocarcinogenes by cyclopropenoid fatty acids and the effect of gossypol and altered lipids on aflatoxin-induced liver cancer. 1968 J. Natl. Cancer Inst. pmid:4178161
Dhaliwal MK et al. Cytogenetic analysis of a gossypol-induced murine myxosarcoma. 1987 J. Natl. Cancer Inst. pmid:3473256
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
Boonsri S et al. Cytotoxic and antibacterial sesquiterpenes from Thespesia populnea. 2008 J. Nat. Prod. pmid:18553924
Lu Z et al. Mirabamides E-H, HIV-inhibitory depsipeptides from the sponge Stelletta clavosa. 2011 J. Nat. Prod. pmid:21280591
Meng YL et al. Coordinated accumulation of (+)-delta-cadinene synthase mRNAs and gossypol in developing seeds of Gossypium hirsutum and a new member of the cad1 family from G. arboreum. 1999 J. Nat. Prod. pmid:10075752
Keller PA et al. Novel pharmacophore-based methods reveal gossypol as a reverse transcriptase inhibitor. 2003 J. Mol. Graph. Model. pmid:12543135
Szücs G et al. Characterization of volume-activated chloride currents in endothelial cells from bovine pulmonary artery. 1996 J. Membr. Biol. pmid:8801351
Nordenskjöld M and Lambert B Gossypol induces DNA strand breaks in human fibroblasts and sister chromatid exchanges in human lymphocytes in vitro. 1984 J. Med. Genet. pmid:6716412
Tsui YC et al. The effect of the male contraceptive agent Gossypol on human lymphocytes in vitro: traditional chromosome breakage, micronuclei, sister chromatid exchange, and cell kinetics. 1983 J. Med. Genet. pmid:6842561
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
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
Feng BY et al. A high-throughput screen for aggregation-based inhibition in a large compound library. 2007 J. Med. Chem. pmid:17447748
Choi SR et al. Design, synthesis, and biological evaluation of Plasmodium falciparum lactate dehydrogenase inhibitors. 2007 J. Med. Chem. pmid:17636950
Tang G et al. Acylpyrogallols as inhibitors of antiapoptotic Bcl-2 proteins. 2008 J. Med. Chem. pmid:18237106
Royer RE et al. Synthesis and anti-HIV activity of 1,1'-dideoxygossypol and related compounds. 1995 J. Med. Chem. pmid:7608907
Wang G et al. Structure-based design of potent small-molecule inhibitors of anti-apoptotic Bcl-2 proteins. 2006 J. Med. Chem. pmid:17034116
Yan F et al. A novel water-soluble gossypol derivative increases chemotherapeutic sensitivity and promotes growth inhibition in colon cancer. 2010 J. Med. Chem. pmid:20684596
Wei J et al. Synthesis and biological evaluation of Apogossypolone derivatives as pan-active inhibitors of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins. 2010 J. Med. Chem. pmid:21033669
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Das SG et al. Structure-activity relationship and molecular mechanisms of ethyl 2-amino-4-(2-ethoxy-2-oxoethyl)-6-phenyl-4h-chromene-3-carboxylate (sha 14-1) and its analogues. 2009 J. Med. Chem. pmid:19743858
Wei J et al. Apogossypol derivatives as pan-active inhibitors of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins. 2009 J. Med. Chem. pmid:19555126
Ionov M et al. The immobilization of gossypol derivative on N-polyvinylpyrrolidone increases its water solubility and modifies membrane-active properties. 2009 J. Med. Chem. pmid:19603832
Deck LM et al. Gossypol and derivatives: a new class of aldose reductase inhibitors. 1991 J. Med. Chem. pmid:1956050
Wei J et al. BI-97C1, an optically pure Apogossypol derivative as pan-active inhibitor of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins. 2010 J. Med. Chem. pmid:20443627
Barelier S et al. Fragment-based deconstruction of Bcl-xL inhibitors. 2010 J. Med. Chem. pmid:20192224
Granchi C et al. Discovery of N-hydroxyindole-based inhibitors of human lactate dehydrogenase isoform A (LDH-A) as starvation agents against cancer cells. 2011 J. Med. Chem. pmid:21332213
Guo J and Reidenberg MM Inhibition of 11beta-hydroxysteroid dehydrogenase by bioflavonoids and their interaction with furosemide and gossypol. 1998 J. Lab. Clin. Med. pmid:9665369
Wu G et al. Responses of three successive generations of beet armyworm, Spodoptera exigua, fed exclusively on different levels of gossypol in cotton leaves. 2010 J. Insect Sci. pmid:21067414
Russell DH et al. Prolactin-dependent mitogenesis in Nb 2 node lymphoma cells: effects of immunosuppressive cyclopeptides. 1987 J. Immunol. pmid:3097147