Garcinol

Modify Date: 2024-01-02 12:30:12

Garcinol Structure
Garcinol structure
Common Name Garcinol
CAS Number 78824-30-3 Molecular Weight 602.800
Density 1.1±0.1 g/cm3 Boiling Point 710.8±60.0 °C at 760 mmHg
Molecular Formula C38H50O6 Melting Point 235-236ºC
MSDS N/A Flash Point 397.6±29.4 °C

 Use of Garcinol


Garcinol, a polyisoprenylated benzophenone harvested from Garcinia indica, exerts anti-cholinesterase properties towards acetyl cholinesterase (AChE) and butyrylcholinesterase (BChE) with IC50s of 0.66 µM and 7.39 µM, respectively[1]. Garcinol also inhibits histone acetyltransferases (HATs, IC50= 7 μM) and p300/CPB-associated factor (PCAF, IC50 = 5 μM). Garcinol has anti-inflammatory and anti-cancer activity[2].

 Names

Name Garcinol
Synonym More Synonyms

 Garcinol Biological Activity

Description Garcinol, a polyisoprenylated benzophenone harvested from Garcinia indica, exerts anti-cholinesterase properties towards acetyl cholinesterase (AChE) and butyrylcholinesterase (BChE) with IC50s of 0.66 µM and 7.39 µM, respectively[1]. Garcinol also inhibits histone acetyltransferases (HATs, IC50= 7 μM) and p300/CPB-associated factor (PCAF, IC50 = 5 μM). Garcinol has anti-inflammatory and anti-cancer activity[2].
Related Catalog
Target

IC50: 0.66 µM (AChE); 7.39 µM (BChE)[1]; 7 μM (HATs); 5 µM (PCAF) [2]

In Vitro Garcinol (10-50 µM; 24-72 hours) can inhibit the proliferation of two HNSCC cell lines tested (CAL27 and UMSCC1) in a time- and dose-dependent manner[3]. Garcinol (10-50 µM; 24-72 hours) induces apoptosis in HNSCC cells[3]. Garcinol (50 µM; 1-6 hours) suppresses phosphorylation and degradation of the constitutive IκBα in a time-dependent manner[3]. Cell Proliferation Assay[3] Cell Line: CAL27 and UMSCC1 cells Concentration: 10, 25, 50 µM Incubation Time: 24, 48, and 72 hours Result: Inhibited the proliferation of two HNSCC cell lines in a time- and dose-dependent manner. Apoptosis Analysis[3] Cell Line: CAL27 and UMSCC1 cells Concentration: 10, 25, 50 µM Incubation Time: 24, 48, and 72 hours Result: Induced apoptosis in HNSCC cells. Western Blot Analysis[3] Cell Line: CAL27 cells Concentration: 50 µM Incubation Time: 1, 2, 4, 6 hours Result: Suppressed phosphorylation and degradation of the constitutive IκBα in a time-dependent manner.
In Vivo Garcinol (i.p.; 1 and 2 mg/kg; five times/week for 4 consecutive weeks) induces significant inhibition of tumor growth[3]. Animal Model: Five-week-old athymic nu/nu male mice bearing subcutaneous CAL27 tumors[3] Dosage: 1 and 2 mg/kg Administration: I.p.; five times/week for 4 consecutive weeks Result: Induced significant inhibition of tumor growth.
References

[1]. Lenta BN, et al. Leishmanicidal and cholinesterase inhibiting activities of phenolic compounds from Allanblackia monticola and Symphonia globulifera. Molecules. 2007 Jul 20;12(8):1548-57.

[2]. Ciochina R, et al. Polycyclic polyprenylated acylphloroglucinols. Chem Rev. 2006 Sep;106(9):3963-86.

[3]. Li F, et al. Garcinol, a polyisoprenylated benzophenone modulates multiple proinflammatory signalingcascades leading to the suppression of growth and survival of head and neck carcinoma. Cancer Prev Res (Phila). 2013 Aug;6(8):843-54.

 Chemical & Physical Properties

Density 1.1±0.1 g/cm3
Boiling Point 710.8±60.0 °C at 760 mmHg
Melting Point 235-236ºC
Molecular Formula C38H50O6
Molecular Weight 602.800
Flash Point 397.6±29.4 °C
Exact Mass 602.360718
PSA 111.90000
LogP 11.26
Vapour Pressure 0.0±2.4 mmHg at 25°C
Index of Refraction 1.563

 Synonyms

Garcinol
guttiferone F
guttiferone E
Bicyclo[3.3.1]non-3-ene-2,9-dione, 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]-, (1R,5R,7R)-
(1R,5R,7R)-3-(3,4-Dihydroxybenzoyl)-4-hydroxy-5-[(2S)-2-isopropenyl-5-methyl-4-hexen-1-yl]-8,8-dimethyl-1,7-bis(3-methyl-2-buten-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione
(1R,5R,7R)-3-(3,4-Dihydroxybenzoyl)-4-hydroxy-8,8-dimethyl-1,7-bis(3-methylbut-2-en-1-yl)-5-[(2S)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]bicyclo[3.3.1]non-3-ene-2,9-dione
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