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Garcinol

Names

[ CAS No. ]:
78824-30-3

[ Name ]:
Garcinol

[Synonym ]:
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

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]:

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.

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

MSDS

Click to get detail MSDS

Related Compounds