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Details

Stereochemistry ACHIRAL
Molecular Formula C19H18O7
Molecular Weight 358.342
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GARDENIN B

SMILES

COC1=CC=C(C=C1)C2=CC(=O)C3=C(O)C(OC)=C(OC)C(OC)=C3O2

InChI

InChIKey=LXEVSYZNYDZSOB-UHFFFAOYSA-N
InChI=1S/C19H18O7/c1-22-11-7-5-10(6-8-11)13-9-12(20)14-15(21)17(23-2)19(25-4)18(24-3)16(14)26-13/h5-9,21H,1-4H3

HIDE SMILES / InChI

Molecular Formula C19H18O7
Molecular Weight 358.342
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/26268971 | https://www.ncbi.nlm.nih.gov/pubmed/25378691 | https://www.ncbi.nlm.nih.gov/pubmed/23926120

Gardenin B is naturally occurring flavonoid isolated from Baccharis scandens, that shows potent anti-proliferative activity against human cancer cell lines. Although the exact target and binding sites of gardenin B have not yet been determined, the introduction of additional methyl groups could facilitate penetration through the cell membrane and increase the cytotoxicity in vitro. Cell cycle analysis performed in HL-60 cells showed that inhibition of cell viability by gardenin B was caused by a significant cell cycle arrest at the S and G2-M phases and accompanied by an increase in sub-G1 fraction and phosphatidylserine externalization, indicating apoptotic cell death. This methoxyflavonoid promotes the formation of apoptotic bodies and the internucleosomal degradation of DNA, resulting in the formation and eventual release of oligonucleosomal DNA fragments. Apoptosis induced by gardenin B is associated with activation of both the extrinsic and the intrinsic apoptotic pathways of cell death and occurs through a mechanism that is independent of the generation of reactive oxygen species.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Structural determination of abutilins A and B, new flavonoids from Abutilon pakistanicum, by 1D and 2D NMR spectroscopy.
2010 Feb
Inhibitory effects of 5-hydroxy polymethoxyflavones on colon cancer cells.
2010 Jul
Constituents of Calamintha ashei: effects on Florida sandhill species.
2010 May
Characterization of two candidate flavone 8-O-methyltransferases suggests the existence of two potential routes to nevadensin in sweet basil.
2013 Aug
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In vitro tubulin polymerization assays were performed as described by the manufacturer (Cytoskeleton, Inc., Denver, CO). Briefly, gardenin B was incubated with purified bovine tubulin in 80 mM PIPES buffer (pH 7.0) containing 1 mM GTP, 1 mM EGTA, 1 mM MgCl2, and 10% glycerol, and the increase in absorbance was measured at 340 nm in a Beckman Coulter DTX880 microplate reader at 37 C and recorded every 30 s for 50 min. Taxol (10 mkM) and colchicine (5 mkM) were used as positive controls of promotion and inhibition of tubulin polymerization, respectively.
Substance Class Chemical
Created
by admin
on Sat Dec 16 04:28:45 GMT 2023
Edited
by admin
on Sat Dec 16 04:28:45 GMT 2023
Record UNII
313E89KN5E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GARDENIN B
MI  
Common Name English
FLAVONE, 5-HYDROXY-4',6,7,8-TETRAMETHOXY-
Systematic Name English
5-HYDROXY-4',6,7,8-TETRAMETHOXYFLAVONE
Systematic Name English
5-O-DESMETHYLTANGERETIN
Common Name English
5-DEMETHYLTANGERETIN
Common Name English
GARDENIN B [MI]
Common Name English
4H-1-BENZOPYRAN-4-ONE, 5-HYDROXY-6,7,8-TRIMETHOXY-2-(4-METHOXYPHENYL)-
Systematic Name English
NSC-79093
Code English
5-HYDROXY-6,7,8,4'-TETRAMETHOXYFLAVONE
Systematic Name English
NSC-618926
Code English
DEMETHYLTANGERETIN
Common Name English
Code System Code Type Description
CAS
2798-20-1
Created by admin on Sat Dec 16 04:28:45 GMT 2023 , Edited by admin on Sat Dec 16 04:28:45 GMT 2023
PRIMARY
MERCK INDEX
m5669
Created by admin on Sat Dec 16 04:28:45 GMT 2023 , Edited by admin on Sat Dec 16 04:28:45 GMT 2023
PRIMARY Merck Index
CHEBI
79628
Created by admin on Sat Dec 16 04:28:45 GMT 2023 , Edited by admin on Sat Dec 16 04:28:45 GMT 2023
PRIMARY
NSC
79093
Created by admin on Sat Dec 16 04:28:45 GMT 2023 , Edited by admin on Sat Dec 16 04:28:45 GMT 2023
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NSC
618926
Created by admin on Sat Dec 16 04:28:45 GMT 2023 , Edited by admin on Sat Dec 16 04:28:45 GMT 2023
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PUBCHEM
96539
Created by admin on Sat Dec 16 04:28:45 GMT 2023 , Edited by admin on Sat Dec 16 04:28:45 GMT 2023
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FDA UNII
313E89KN5E
Created by admin on Sat Dec 16 04:28:45 GMT 2023 , Edited by admin on Sat Dec 16 04:28:45 GMT 2023
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EPA CompTox
DTXSID10182260
Created by admin on Sat Dec 16 04:28:45 GMT 2023 , Edited by admin on Sat Dec 16 04:28:45 GMT 2023
PRIMARY