GAMBOGIC ACID

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C38H44O8
Molecular Weight	628.7512
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)=CCC[C@@]1(C)OC2=C(C=C1)C(O)=C3C(=O)C4=C[C@@H]5C[C@H]6C(C)(C)O[C@@](C\C=C(\C)C(O)=O)(C5=O)[C@@]46OC3=C2CC=C(C)C

InChI

InChIKey=GEZHEQNLKAOMCA-RRZNCOCZSA-N

InChI=1S/C38H44O8/c1-20(2)10-9-15-36(8)16-14-24-29(39)28-30(40)26-18-23-19-27-35(6,7)46-37(33(23)41,17-13-22(5)34(42)43)38(26,27)45-32(28)25(31(24)44-36)12-11-21(3)4/h10-11,13-14,16,18,23,27,39H,9,12,15,17,19H2,1-8H3,(H,42,43)/b22-13-/t23-,27+,36-,37+,38-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C38H44O8
Molecular Weight	628.7512
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27448303
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/17876042 | https://www.ncbi.nlm.nih.gov/pubmed/22759348 | https://www.ncbi.nlm.nih.gov/pubmed/16103367

Gambogic acid (GA), a naturally occurring xanthone-based moiety, reported from Garcinia hanburyi tree, is known to perform numerous intracellular and extracellular actions, including programmed cell death, autophagy, cell cycle arrest, antiangiogenesis, antimetastatic, and anti-inflammatory activities. In addition, GA-based synergistic approaches have been proven to enhance the healing strength of existing chemotherapeutic agents along with lesser side effects. Among cellular targets of gambogic acid topoisomerase, multidrug-resistant protein ATP-binding cassette transporter B1 (ABCB1) and Transferrin receptor.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Potency
DNA topoisomerase II alpha 37 Target ID: CHEMBL1806 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17876042	Inhibitor 8297	6.3 µM [IC50]
DNA topoisomerase 1 16 Target ID: CHEMBL5948 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17876042	Inhibitor 8297	50.0 µM [IC50]
Cannabinoid CB2 receptor 71 Target ID: CHEMBL253 Sources: http://www.fasebj.org/content/24/1_Supplement/769.1.short?cited-by=yes&legid=fasebj%3B24%2F1_Supplement%2F769.1&trendmd-shared=1	Partial Agonist 290	3.6 µM [Ki]
26S proteosome 7 Target ID: CHEMBL2364701 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23260670	Inhibitor 8297	25.0 µM [IC50]
P-glycoprotein 1 54 Target ID: CHEMBL4302 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22759348	Inhibitor 8297
Transferrin receptor protein 1 1 Target ID: P02786 Gene ID: 7037.0 Gene Symbol: TFRC Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16103367	Modulator 828	2.2 µM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27448303	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Anticancer effect and apoptosis induction of gambogic acid in human gastric cancer line BGC-823.	2005 Jun 28	15968715
Gambogic acid induces G0/G1 arrest and apoptosis involving inhibition of SRC-3 and inactivation of Akt pathway in K562 leukemia cells.	2009 Aug 3	19433130
Synergistic effect of 5-fluorouracil with gambogic acid on BGC-823 human gastric carcinoma.	2009 Feb 4	19084572
Reactive oxygen species accumulation contributes to gambogic acid-induced apoptosis in human hepatoma SMMC-7721 cells.	2009 Jun 16	19464570
Calcium channel blocker verapamil accelerates gambogic acid-induced cytotoxicity via enhancing proteasome inhibition and ROS generation.	2014 Apr	24373880
The combination of proteasome inhibitors bortezomib and gambogic acid triggers synergistic cytotoxicity in vitro but not in vivo.	2014 Jan 30	24291039
Gambogic acid sensitizes resistant breast cancer cells to doxorubicin through inhibiting P-glycoprotein and suppressing survivin expression.	2015 Jun 25	25824409

Patents

Sample Use Guides

In Vivo Use Guide

The animals in the treatment group received one of three dosages of gambogic acid (in saline; 5, 10 or 20 mg/kg) via the caudal vein twice weekly. For intraperitoneal administration the mice were randomly assigned to treatment with 10, 20 or 30 mg/kg gambogic acid for 3 weeks.

Route of Administration: Other

In Vitro Use Guide

Gambogic acid displays potent antiproliferative activity against a wide panel of human tumors without distinct selectivity among the cells lines tested. The average IC50 of GA against the 21 cell lines was 1.23 μmol/L.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:12:25 UTC 2023` Edited by `admin` on `Sat Dec 16 08:12:25 UTC 2023`
Record UNII	8N585K83U2
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GAMBOGIC ACID

Common Name

English

.BETA.-GUTTIFERIN

Common Name

English

GAMBOGIC ACID [MI]

Common Name

English

(2Z)-2-METHYL-4-((1R,3AS,5S,11R,14AS)-3A,4,5,7-TETRAHYDRO-8-HYDROXY-3,3,11-TRIMETHYL-13-(3-METHYL-2-BUTEN-1-YL)-11-(4-METHYL-3-PENTEN-1-YL)-7,15-DIOXO-1,5-METHANO-1H,3H,11H-FURO(3,4-G)PYRANO(3,2-B)XANTHEN-1-YL)-2-BUTENOIC ACID

Systematic Name

English

2-BUTENOIC ACID, 2-METHYL-4-((1R,3AS,5S,11R,14AS)-3A,4,5,7-TETRAHYDRO-8-HYDROXY-3,3,11-TRIMETHYL-13-(3-METHYL-2-BUTEN-1-YL)-11-(4-METHYL-3-PENTEN-1-YL)-7,15-DIOXO-1,5-METHANO-1H,3H,11H-FURO(3,4-G)PYRANO(3,2-B)XANTHEN-1-YL)-, (2Z)-

Systematic Name

English

R-GAMBOGIC ACID

Common Name

English

(-)-GAMBOGIC ACID

Common Name

English

Code System Code Type Description

CAS

2752-65-0