(±)-Gossypol


CAS No. : 303-45-7

(±)-Gossypol,303-45-7
Product Details
For research use only. Not Intended for Therapeutic Use!
Cat No:I003062
Synonyms:7-(8-formyl-1,6,7-trihydroxy-3-methyl-5-propan-2-ylnaphthalen-2-yl)-2,3,8-trihydroxy-6-methyl-4-propan-2-ylnaphthalene-1-carbaldehyde
Molecular Formula:C₃₀H₃₀O₈
Molecular Weight:518.55
Target:Bcl-2 Family
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Appearance:Solid powder
Purity: > 98%
Cat No:I003062
Cas No:303-45-7
Product-Name:(±)-Gossypol
MDL No:MFCD00017352
InChI:InChI=1S/C30H30O8/c1-11(2)19-15-7-13(5)21(27(35)23(15)17(9-31)25(33)29(19)37)22-14(6)8-16-20(12(3)4)30(38)26(34)18(10-32)24(16)28(22)36/h7-12,33-38H,1-6H3
InChIKey:QBKSWRVVCFFDOT-UHFFFAOYSA-N
SMILES:CC1=C(C(=C2C(=C1)C(=C(C(=C2C=O)O)O)C(C)C)O)C3=C(C=C4C(=C3O)C(=C(C(=C4C(C)C)O)O)C=O)C

Gossypol has been known to exert a potential for anti-cancer, anti-inflammatory and other important therapeutic activities, gossypol binds and antagonizes anti-apoptotic effect of Bcl-2 family proteins.
IC50 value:
Target: Bcl-2; anticancer agent
The substance, a yellow pigment similar to flavonoids, is present in cottonseed oil. In the plant, it acts as a natural defensive agent against predators, provoking infertility in insects. In most animals, gossypol provokes infertility, and in man it causes spermatogenesis arrest at relatively low doses.
in vitro: The natural product and putative BH3 mimetic gossypol enhanced the cytotoxicity of BRD4770 in a synergistic manner in p53-mutant PANC-1 cells but not in immortalized non-tumorigenic pancreatic cells. The combination of gossypol and BRD4770 increased LC3-II levels and the autophagosome number in PANC-1 cells, and the compound combination appears to act in a BNIP3 (B-cell lymphoma 2 19-kDa interacting protein)-dependent manner [1]. Gossypol treatment resulted in cell death through oxidative stress. Metabolite analysis showed that gossypol induces a decrease of the cellular levels of GSH, aspartic acid, and FAD in ovarian cancer cell line, SKOV3 [2]. gossypol blocked the phosphorylation of IκBα protein, p65, p38, c-Junterminal kinase (JNK) and extracellular signal-regulated kinase (ERK) in LPS stimulated RAW 264.7 cells [3]. gossypol could down-regulate activation of ConA-induced NF-κB, NFAT and AP-1 signal transduction pathways in mouse T lymphocyte [4].
in vivo: gossypol significantly inhibited the production of LPS-induced TNF-α, IL-6 and IL-1β both in vitro and vivo.gossypol attenuated lung histopathologic changes in mouse models [3].Preliminary studies in vivo showed that a growth inhibition (T/C) of 30.9% (gossypol acetate 40 mg/kg) was obtained in Balb/C mice bearing Wus1 cells. In addition, there was no body weight loss for the treated group in comparison with the vehicle mice [5].


1:Development of SECheM Concept for Isolation and Chemical Modification of Gossypol Directly from Cienfuegosia digitata. Sidi Boune MV, Ould Elemine B, Lepitre T, Ould Hadou A, Aliyenne A, Boumediana AI, Daïch A, Othman M, Lawson AM.Phytochem Anal. 2017 May 5. doi: 10.1002/pca.2688. [Epub ahead of print] PMID: 28474346
2:The Lactate Dehydrogenase Inhibitor Gossypol Inhibits Radiation-Induced Pulmonary Fibrosis. Judge JL, Lacy SH, Ku WY, Owens KM, Hernady E, Thatcher TH, Williams JP, Phipps RP, Sime PJ, Kottmann RM.Radiat Res. 2017 May 2. doi: 10.1667/RR14620.1. [Epub ahead of print] PMID: 28463588
3:Preparation and evaluation of molecularly imprinted polymer for selective recognition and adsorption of gossypol. Zhi K, Wang L, Zhang Y, Zhang X, Zhang L, Liu L, Yao J, Xiang W.J Mol Recognit. 2017 Mar 22. doi: 10.1002/jmr.2627. [Epub ahead of print] PMID: 28326626
4:Gossypol has anti-cancer effects by dual-targeting MDM2 and VEGF in human breast cancer. Xiong J, Li J, Yang Q, Wang J, Su T, Zhou S.Breast Cancer Res. 2017 Mar 9;19(1):27. doi: 10.1186/s13058-017-0818-5. PMID: 28274247 Free PMC Article
5:Gossypol with Hydrophobic Linear Esters Exhibits Enhanced Antitumor Activity as an Inhibitor of Antiapoptotic Proteins. Lu Y, Wu S, Yue Y, He S, Li J, Tang J, Wang W, Zhou HB.ACS Med Chem Lett. 2016 Oct 19;7(12):1185-1190. eCollection 2016 Dec 8. PMID: 27994761
6:Determination of gossypol content in cottonseeds by near infrared spectroscopy based on Monte Carlo uninformative variable elimination and nonlinear calibration methods. Li C, Zhao T, Li C, Mei L, Yu E, Dong Y, Chen J, Zhu S.Food Chem. 2017 Apr 15;221:990-996. doi: 10.1016/j.foodchem.2016.11.064. Epub 2016 Nov 15. PMID: 27979304
7:Dietary gossypol suppressed postprandial TOR signaling and elevated ER stress pathways in turbot (Scophthalmus maximus L.). Bian F, Jiang H, Man M, Mai K, Zhou H, Xu W, He G.Am J Physiol Endocrinol Metab. 2017 Jan 1;312(1):E37-E47. doi: 10.1152/ajpendo.00285.2016. Epub 2016 Nov 15. PMID: 27894064
8:Expression in Pichia pastoris and characterization of two novel dirigent proteins for atropselective formation of gossypol. Effenberger I, Harport M, Pfannstiel J, Klaiber I, Schaller A.Appl Microbiol Biotechnol. 2017 Mar;101(5):2021-2032. doi: 10.1007/s00253-016-7997-3. Epub 2016 Nov 17. PMID: 27858135
9:Injectable (-)-gossypol-loaded Pluronic P85 micelles for cancer chemoradiotherapy. Tomoda K, Chiang HC, Kozak KR, Kwon GS.Int J Radiat Biol. 2017 Apr;93(4):402-406. doi: 10.1080/09553002.2016.1257833. Epub 2016 Dec 9. PMID: 27827005
10:Gossypol toxicity and detoxification in Helicoverpa armigera and Heliothis virescens. Krempl C, Heidel-Fischer HM, Jiménez-Alemán GH, Reichelt M, Menezes RC, Boland W, Vogel H, Heckel DG, Joußen N.Insect Biochem Mol Biol. 2016 Nov;78:69-77. doi: 10.1016/j.ibmb.2016.09.003. Epub 2016 Sep 26. PMID: 27687846
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