Garcinol CAS: 78824-30-3
MF: C38H50O6
MW: 602.80

Garcinol (CAS 78824-30-3)

Garcinol | CAS 78824-30-3 is rated 5.0 out of 5 by 1.
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Alternate Names: Garcinol is also known as Camboginol.
Application: Garcinol is a polyisoprenylated benzophenone derived p300 and PCAF histone acetyltransferase inhibitor.
CAS Number: 78824-30-3
Purity: ≥95%
Molecular Weight: 602.80
Molecular Formula: C38H50O6
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data (including water content).
DISCOUNT: Bulk orders of Chemicals totaling $1,000 or more receive a 5% discount.
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Garcinol (camboginol) is a polyisoprenylated benzophenone derivative from the rind of Garcinia indica fruit and is a potent inhibitor of histone acetyltransferases p300 (IC50= ~7 µm) and PCAF (IC50= ~5 µm) both in vitro and in vivo. p300, also known as E1A binding protein p300, regulates cell growth and division through interacting with numerous transcription factors, and the p53 associated trancriptional coactivator PCAF (P300/CBP-associated factor) plays a direct role in transcriptional regulation. Reports show that Garcinol represses the p300-mediated acetylation of p53 in vivo, promotes apoptosis through caspase-3 activation and predominantly down-regulates the global gene expression in HeLa cells. Researchers found that Garcinol exhibits dose-dependent cancer cell-specific growth inhibition in ER-positive MCF-7 and ER-negative MDA-MB-231 breast cancer cells. Additional research shows that Garcinol exhibits anti-carcinogenic and anti-inflammatory properties through selectively suppressing Prostaglandin E2 synthesis and 5-lipoxygenase product formation. Garcinol is also known as Camboginol, and 3-(3,4-dihydroxybenzoyl)-4-hydroxy-8,8-dimethyl-1,7-bis(3-methyl-2-buten-1-yl)-5-[(2S)-5-methyl-2-(1-methylethenyl)-4-hexen-1-yl]-bicyclo[3.3.1]non-3-ene-2,9-dione.


References

1. Matsumoto, Kenji., et al., 2003. Cytotoxic benzophenone derivatives from Garcinia species display a strong apoptosis-inducing effect against human leukemia cell lines. Biological & pharmaceutical bulletin. 26(4): 569-71. PMID: 12673047

2. Balasubramanyam, Karanam., et al., 2004. Polyisoprenylated benzophenone, garcinol, a natural histone acetyltransferase inhibitor, represses chromatin transcription and alters global gene expression. The Journal of biological chemistry. 279(32): 33716-26. PMID: 15155757

3. Mantelingu, K., et al., 2007. Specific inhibition of p300-HAT alters global gene expression and represses HIV replication. Chemistry & biology. 14(6): 645-57. PMID: 17584612

4. Koeberle, Andreas., et al., 2009. Identification of 5-lipoxygenase and microsomal prostaglandin E2 synthase-1 as functional targets of the anti-inflammatory and anti-carcinogenic garcinol. Biochemical pharmacology. 77(9): 1513-21. PMID: 19426689

5. Ahmad, Aamir., et al., 2010. Apoptosis-inducing effect of garcinol is mediated by NF-kappaB signaling in breast cancer cells. Journal of cellular biochemistry. 109(6): 1134-41. PMID: 20108249

6. Chen, Ching-Shyang., et al., 2011. Nicotine-induced human breast cancer cell proliferation attenuated by garcinol through down-regulation of the nicotinic receptor and cyclin D3 proteins. Breast cancer research and treatment. 125(1): 73-87. PMID: 20229177

Physical State :
Solid
Solubility :
Soluble in ethanol (25 mg/ml), DMSO (25 mg/ml), and DMF (25 mg/ml). Insoluble in water.
Storage :
Store at -20° C
Melting Point :
72° C
Boiling Point :
~710.8° C at 760 mmHg (Predicted)
Density :
~1.1 g/cm3 (Predicted)
Refractive Index :
n20D 1.56
IC50 :
histone acetyltransferases (HATs) p300: IC50 = 7 µM; PCAF: IC50 = 5 µM
Ki Data :
Histone acetyltransferase p300: Ki= 4900 nM
pK Values :
pKa: 4.5
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
2
PubChem CID :
MDL Number :
MFCD03700761
SMILES :
CC(=CCC1CC2(C(=O)C(=C(C3=CC(=C(C=C3)O)O)O)C(=O)C(C2=O)(C1(C)C)CC=C(C)C)CC(CC=C(C)C)C(=C)C)C

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Certificate of Analysis

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Garcinol (CAS 78824-30-3)  Product Citations

See how others have used Garcinol (CAS 78824-30-3). Click on the entry to view the PubMed entry .

Citations 1 to 9 of 9 total

PMID: # 34017833  Xia, S.|Yu, W.|Menden, H.|Younger, ST.|Sampath, V.| et al. 2021. Front Cell Dev Biol. 9: 657662.

PMID: # 33809417  Chang, NC.|Yeh, CT.|Lin, YK.|Kuo, KT.|Fong, IH.|Kounis, NG.|Hu, P.|Hung, MY.| et al. 2021. Antioxidants (Basel). 10:

PMID: # 29174768  Ghosh, TK. et al. 2018. J. Mol. Cell. Cardiol. 114: 185-198.

PMID: # 29414668  Huang, WC.|Kuo, KT.|Adebayo, BO.|Wang, CH.|Chen, YJ.|Jin, K.|Tsai, TH.|Yeh, CT.| et al. 2018. J. Nutr. Biochem. 54: 140-150.

PMID: # 29740418  Simpson, S. et al. 2018. Front Microbiol. 9: 788.

PMID: # 25538147  Yao, XH. et al. 2014. Physiological reports. 2:

PMID: # 23644046  Du, T. et al. 2013. Experimental and molecular pathology. 95: 38-45.

PMID: # 33300026  Nucleic Acids Res.

PMID: # 30377593  Habibi, A.|Soleimani, M.|Atashi, A.|AkhavanRahnama, M.|Anbarlou, A.|Ajami, M.|Ajami, M.| et al. Avicenna J Phytomed. 8: 350-357.

Citations 1 to 9 of 9 total

How long would you recommend storing the stock solution?

Asked by: chemicalsmg
Thank you for your question. We do not recommend storing the aqueous solution for more than one day. If you have any further questions or concerns, please feel free to contact our Technical Service department by calling 800-457-3801 option 2, emailing [email protected], or using the Live Chat function on our website.
Answered by: Tech Service 8
Date published: 2017-01-12
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Rated 5 out of 5 by from Chen et al Chen et al. (PubMed ID 20229177) used garcinol to reduce the expression of nicotinic receptors in human breast cancer cells by blocking acetylation of the cyclin D1promoter. -SCBT Publication Review
Date published: 2015-06-06
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