KAEMPFERIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H12O6
Molecular Weight	300.2629
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=SQFSKOYWJBQGKQ-UHFFFAOYSA-N

InChI=1S/C16H12O6/c1-21-10-4-2-8(3-5-10)16-15(20)14(19)13-11(18)6-9(17)7-12(13)22-16/h2-7,17-18,20H,1H3

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28928604 | https://www.ncbi.nlm.nih.gov/pubmed/26345098 | https://www.ncbi.nlm.nih.gov/pubmed/23869536 | https://www.ncbi.nlm.nih.gov/pubmed/23355380 | http://pubs.rsc.org/-/content/articlelanding/2015/ra/c5ra19199h/unauth#!divAbstract

Kaempferide (3,5,7-trihydroxy-4′-methoxyflavone, Kae) is a naturally occurring flavonoid that is isolated from the roots of Alpinia officinarum (lesser galangal). Like other flavonoids, Kae also has a very good antioxidant properties and Kae can effectively reduce 1,1- diphenyl-2-picrylhydrazyl (DPPH). Studies have shown that Kae has anticancer and antihypertension effects. Kaempferide protects against myocardial Ischemia/reperfusion Injury through activation of the PI3K/Akt/GSK-3β pathway. Kaempferide inhibited potent antioxidant activity. Kaempferide is one of the candidates for active compound in propolis. Kaempferide, the most active among the four flavonoids isolated and characterized from Chromolaena odorata, induces apoptosis in cervical cancer cells while being pharmacologically safe.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Tyrosine--tRNA ligase 1 Target ID: P0AGJ9 Gene ID: 948855.0 Gene Symbol: tyrS Target Organism: Escherichia coli (strain K12) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27487455	Inhibitor 8297
TRAIL receptor-1 1 Target ID: CHEMBL3551 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25580686	Activator 1430
Oxidative Stress 160 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23869536 \| https://www.ncbi.nlm.nih.gov/pubmed/23840273	Inhibitor 8297
Hypoxia-inducible factor 1 alpha 17 Target ID: CHEMBL4261 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21865046	Inhibitor 8297
Tyrosinase 41 Target ID: CHEMBL5346 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19615910	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Cardiovascular diseases 71 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28928604 https://www.ncbi.nlm.nih.gov/pubmed/21865046	Primary	Preclinical	Unknown Approved Use Unknown
Amyotrophic lateral sclerosis 41 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28588226	Primary	Basic research	Unknown Approved Use Unknown
Hyperpigmentation 14 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19615910	Primary	Basic research	Unknown Approved Use Unknown
Cervical cancer 40 Sources: http://pubs.rsc.org/-/content/articlelanding/2015/ra/c5ra19199h/unauth#!divAbstract	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Oxidation of the flavonoids galangin and kaempferide by human liver microsomes and CYP1A1, CYP1A2, and CYP2C9.	2002 Feb	11792676
Metabolic modifications of birch leaf phenolics by an herbivorous insect: detoxification of flavonoid aglycones via glycosylation.	2004 May-Jun	18998416
Flavonoids from Echinops echinatus.	2006 Apr-May	16864424
In vitro antimalarial activity of flavonoid derivatives dehydrosilybin and 8-(1;1)-DMA-kaempferide.	2006 Jan	16256062
Effects of propolis crude hydroalcoholic extract on chromosomal aberrations induced by doxorubicin in rats.	2007 Dec	17999350
Phenolics of Moringa oleifera leaves.	2007 Jan	17365690
Bioavailable flavonoids: cytochrome P450-mediated metabolism of methoxyflavones.	2007 Nov	17709371
A new chalcone glycoside from Rhamnus nipalensis.	2008 Dec	19085424
[Studies on chemical constituents of Salacia prinoides].	2008 Sep	19180955
Chemical composition and botanical origin of red propolis, a new type of brazilian propolis.	2008 Sep	18830449
Melanogenesis inhibitors from the rhizomes of Alpinia officinarum in B16 melanoma cells.	2009 Aug 15	19615910
6-Hydroxy-methyl-4-meth-oxy-2H-pyran-2-one (Opuntiol).	2009 Dec 19	21580082
Antihypertensive effects of flavonoids isolated from brazilian green propolis in spontaneously hypertensive rats.	2009 Jul	19571393
From functional food to medicinal product: systematic approach in analysis of polyphenolics from propolis and wine.	2009 Jul 22	19624827
Cytochrome P450 CYP1A1: wider roles in cancer progression and prevention.	2009 Jun 16	19531241
Methylation of dietary flavones increases their metabolic stability and chemopreventive effects.	2009 Nov 18	20087474
Interaction of flavonoids, the naturally occurring antioxidants with different media: a UV-visible spectroscopic study.	2010 Apr	20163982
Oleuropein in olive and its pharmacological effects.	2010 Apr-Jun	21179340
Reversing β-lactam antibiotic resistance of Staphylococcus aureus with galangin from Alpinia officinarum Hance and synergism with ceftazidime.	2010 Dec 15	21036573
Effects of single and multiple flavonoids on BCRP-mediated accumulation, cytotoxicity and transport of mitoxantrone in vitro.	2010 Jul	20369276
Inhibition of in vitro growth and arrest in the G0/G1 phase of HCT8 line human colon cancer cells by kaempferide triglycoside from Dianthus caryophyllus.	2010 Sep	20104502
Discovery of flavonoid derivatives as anti-HCV agents via pharmacophore search combining molecular docking strategy.	2012 Jun	22445328

Patents

Sample Use Guides

In Vivo Use Guide

Rats were randomly divided into 7 groups: (1) sham group, rats underwent sham surgery; (2) I/R group, rats were subjected to a 30 min LAD coronary artery ligation followed by a 2 h reperfusion; (3) L-Kae (Kaempferide) + I/R group, rats were injected with a low dose of Kae (L-Kae; 0.1 mg/kg body weight) 30 min prior to I/R, then subjected to a 30 min LAD coronary artery ligation followed by a 2 h reperfusion; (4) M-Kae + I/R group, rats were injected with a moderate dose of Kae (M-Kae; 0.3 mg/kg body weight) 30 min prior to I/R, then subjected to a 30 min LAD coronary artery ligation followed by a 2 h reperfusion; (5) H-Kae + I/R group, rats were injected with a high dose of Kae (H-Kae; 1 mg/kg body weight) 30 min prior to I/R, then subjected to a 30 min LAD coronary artery ligation followed by a 2 h reperfusion;

Route of Administration: Intravenous

In Vitro Use Guide

Kaempferide inhibited melanogenesis (81.2% inhibition) in theophylline-stimulated mouse B16-4A5 cells at 30 uM after 72 hrs

Name

Type

Language

KAEMPFERIDE

Common Name

English

3,5,7-TRIHYDROXY-2-(4-METHOXYPHENYL)CHROMEN-4-ONE

Systematic Name

English

4'-METHYLKAEMPFEROL

Common Name

English

NSC-407294

Code

English

KAEMPFEROL 4'-METHYL ETHER

Common Name

English

4'-O-METHYLKAEMPFEROL

Common Name

English

Code System Code Type Description

CHEBI

58925