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(O2)C=C(O)C=C3O

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

Molecular Formula	C16H12O6
Molecular Weight	300.2629
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 8504
TRAIL receptor-1 1 Target ID: CHEMBL3551 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25580686	Activator 1447
Oxidative Stress 162 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23869536 \| https://www.ncbi.nlm.nih.gov/pubmed/23840273	Inhibitor 8504
Hypoxia-inducible factor 1 alpha 17 Target ID: CHEMBL4261 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21865046	Inhibitor 8504
Tyrosinase 41 Target ID: CHEMBL5346 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19615910	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Cardiovascular diseases 72 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 39 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
Discovery of flavonoid derivatives as anti-HCV agents via pharmacophore search combining molecular docking strategy.	2012-06	22445328
Reversing β-lactam antibiotic resistance of Staphylococcus aureus with galangin from Alpinia officinarum Hance and synergism with ceftazidime.	2010-12-15	21036573
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.	2010-09	20104502
Effects of single and multiple flavonoids on BCRP-mediated accumulation, cytotoxicity and transport of mitoxantrone in vitro.	2010-07	20369276
Interaction of flavonoids, the naturally occurring antioxidants with different media: a UV-visible spectroscopic study.	2010-04	20163982
Inhibitory activity of Brazilian green propolis components and their derivatives on the release of cys-leukotrienes.	2010-01-01	19942440
Studies on the homolytic and heterolytic cleavage of kaempferol and kaempferide glycosides using electrospray ionization tandem mass spectrometry.	2010-01	19960496
Oleuropein in olive and its pharmacological effects.	2009-12-20	21179340
6-Hydroxy-methyl-4-meth-oxy-2H-pyran-2-one (Opuntiol).	2009-12-19	21580082
Methylation of dietary flavones increases their metabolic stability and chemopreventive effects.	2009-11-18	20087474
Melanogenesis inhibitors from the rhizomes of Alpinia officinarum in B16 melanoma cells.	2009-08-15	19615910
From functional food to medicinal product: systematic approach in analysis of polyphenolics from propolis and wine.	2009-07-22	19624827
Antihypertensive effects of flavonoids isolated from brazilian green propolis in spontaneously hypertensive rats.	2009-07	19571393
Cytochrome P450 CYP1A1: wider roles in cancer progression and prevention.	2009-06-16	19531241
A new chalcone glycoside from Rhamnus nipalensis.	2008-12	19085424
Metabolic modifications of birch leaf phenolics by an herbivorous insect: detoxification of flavonoid aglycones via glycosylation.	2008-11-13	18998416
[Studies on chemical constituents of Salacia prinoides].	2008-09	19180955
Brazilian propolis: correlation between chemical composition and antimicrobial activity.	2008-09	18830454
Chemical composition and botanical origin of red propolis, a new type of brazilian propolis.	2008-09	18830449
Antiproliferative and cytostatic effects of the natural product eupatorin on MDA-MB-468 human breast cancer cells due to CYP1-mediated metabolism.	2008	18454852
Effects of propolis crude hydroalcoholic extract on chromosomal aberrations induced by doxorubicin in rats.	2007-12	17999350
Bioavailable flavonoids: cytochrome P450-mediated metabolism of methoxyflavones.	2007-11	17709371
[Studies on flavonoids of Oxytropis falcata].	2007-02	17455467
Phenolics of Moringa oleifera leaves.	2007-01	17365690
Flavonoids from Echinops echinatus.	2006-07-26	16864424
In vitro antimalarial activity of flavonoid derivatives dehydrosilybin and 8-(1;1)-DMA-kaempferide.	2006-01	16256062
ABC transporters as multidrug resistance mechanisms and the development of chemosensitizers for their reversal.	2005-10-04	16202168
Effect of Brazilian green propolis on the production of reactive oxygen species by stimulated neutrophils.	2004-09	15261964
Flavonol glycosides of Warburgia ugandensis leaves.	2003-10	14559287
Oxidation of the flavonoids galangin and kaempferide by human liver microsomes and CYP1A1, CYP1A2, and CYP2C9.	2002-02	11792676
Phenolic compounds of propolis from Central Chilean matorral.	2001-05-24	11371020
Kaempferide triglycoside: a possible factor of resistance of carnation (Dianthus caryophyllus) to Fusarium oxysporum f. sp. dianthi.	2001-04	11314958
Inhibitory activity of flavonoids and tannins against HIV-1 protease.	2000-09	10993207

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

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:38:30 GMT 2025` Edited by `admin` on `Mon Mar 31 19:38:30 GMT 2025`
Record UNII	508XL61MPD
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

KAEMPFERIDE

Common Name

English

NSC-407294

Preferred Name

English

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

Systematic Name

English

4'-METHYLKAEMPFEROL

Common Name

English

KAEMPFEROL 4'-METHYL ETHER

Common Name

English

4'-O-METHYLKAEMPFEROL

Common Name

English

Code System Code Type Description

CHEBI

58925