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Details

Stereochemistry ABSOLUTE
Molecular Formula C38H50O6
Molecular Weight 602.8
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GARCINOL

SMILES

CC(=C)[C@@H](CC=C(C)C)C[C@]12C[C@@H](CC=C(C)C)C(C)(C)[C@](CC=C(C)C)(C(=O)C(C(=O)C3=CC=C(O)C(O)=C3)=C1O)C2=O

InChI

InChIKey=QDKLRKZQSOQWJQ-MZBNNVTPSA-N
InChI=1S/C38H50O6/c1-22(2)11-13-27(25(7)8)20-37-21-28(15-12-23(3)4)36(9,10)38(35(37)44,18-17-24(5)6)34(43)31(33(37)42)32(41)26-14-16-29(39)30(40)19-26/h11-12,14,16-17,19,27-28,39-40,42H,7,13,15,18,20-21H2,1-6,8-10H3/t27-,28+,37?,38?/m0/s1

HIDE SMILES / InChI

Molecular Formula C38H50O6
Molecular Weight 602.8
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/28598692 | https://www.ncbi.nlm.nih.gov/pubmed/28302538 | https://www.ncbi.nlm.nih.gov/pubmed/19101154 | https://www.ncbi.nlm.nih.gov/pubmed/25634295

Garcinol is a polyisoprenylated benzophenone derivative from the rind of Garcinia indica fruit and is a potent inhibitor of histone acetyltransferases. Garcinol is primarily present in family Clusiaceae and genus Garcinia . Although Garcinia indica is commonly referenced in the scientific literature, it is found in other plant species. Numerous in vitro and scientific animal studies on garcinol document anti-inflammatory, antioxidant, anticancer, and antibacterial activity. In preclinical study Topical application or oral administration of garcinol inhibited TPA-induced ear inflammation in a dose-dependent manner in CD-1 mice. TPA-induced expression of proinflammatory cytokine IL-6 protein was inhibited by topical application of garcinol to the ears of CD-1 mice. UVB-induced ear inflammation and proinflammatory cytokines IL-1 beta and IL-6 were inhibited in mice after oral administration of garcinol. Topical application of garcinol strongly inhibited TPA-induced skin tumor promotion in mice. Garcinol is used as an active ingredient in various topical products for its antioxidant activity. It is also used as an additive ingredient in hydroxycitric acid, purported by some commercial manufacturers to improve lean body mass.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.7 µM [IC50]
6.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Polyisoprenylated benzophenone, garcinol, a natural histone acetyltransferase inhibitor, represses chromatin transcription and alters global gene expression.
2004 Aug 6
Patents

Patents

Sample Use Guides

Rat: oral 10-20 mg/kg body weight/day for one month
Route of Administration: Oral
Cell viability was assayed by 3-(4,5-dimethylthiazol-2-yl)-2,5- diphenyltetrazolium bromide (MTT). Hep3B, HepG2, A431, MCF-7, and COLO205 cellswere plated into 24 well plates at a density of 1 x 10^5 cells per well. After overnight growth, cells were treated with a series of garcinol concentrations for 24 h. The final DMSO concentration in the culture medium was <0.05%. At the end of treatment, 30 mL of MTT was added, and the cells were incubated for 4 h. Cell viability was determined by scanning with an enzyme-linked immunosorbent assay reader at 570 nm
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:12:01 UTC 2023
Edited
by admin
on Sat Dec 16 09:12:01 UTC 2023
Record UNII
TR1VR1V71B
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GARCINOL
Common Name English
GARCINOL (CONSTITUENT OF GARCINIA CAMBOGIA AND GARCINIA INDICA) [DSC]
Common Name English
GARCINOL (BENZOPHENONE)
Common Name English
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)-
Common Name English
CAMBOGINOL
Common Name English
Code System Code Type Description
FDA UNII
TR1VR1V71B
Created by admin on Sat Dec 16 09:12:01 UTC 2023 , Edited by admin on Sat Dec 16 09:12:01 UTC 2023
PRIMARY
EPA CompTox
DTXSID201025617
Created by admin on Sat Dec 16 09:12:01 UTC 2023 , Edited by admin on Sat Dec 16 09:12:01 UTC 2023
PRIMARY
CAS
78824-30-3
Created by admin on Sat Dec 16 09:12:01 UTC 2023 , Edited by admin on Sat Dec 16 09:12:01 UTC 2023
PRIMARY
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