78824-30-3

78824-30-3 structure

Name: Garcinol
Chemical Name: Garcinol
CAS Number: 78824-30-3
Molecular Formula: C₃₈H₅₀O₆
Molecular Weight: 602.800
Catalog: Signaling Pathways Apoptosis Apoptosis
Create Date: 2018-08-31 10:08:30
Modify Date: 2024-01-02 12:30:12
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].

Name	Garcinol
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

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	Signaling Pathways >> Apoptosis >> Apoptosis Research Areas >> Cancer Research Areas >> Inflammation/Immunology Signaling Pathways >> Epigenetics >> Histone Acetyltransferase Signaling Pathways >> Neuronal Signaling >> AChE
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.

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