ISOSAKURANETIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H14O5
Molecular Weight	286.2794
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C(C=C1)[C@@H]2CC(=O)C3=C(O)C=C(O)C=C3O2

InChI

InChIKey=HMUJXQRRKBLVOO-AWEZNQCLSA-N

InChI=1S/C16H14O5/c1-20-11-4-2-9(3-5-11)14-8-13(19)16-12(18)6-10(17)7-15(16)21-14/h2-7,14,17-18H,8H2,1H3/t14-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C16H14O5
Molecular Weight	286.2794
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20696580 | https://www.ncbi.nlm.nih.gov/pubmed/24006495 | https://www.ncbi.nlm.nih.gov/pubmed/28715803 | https://www.ncbi.nlm.nih.gov/pubmed/28013186

Isosakuranetin is a citrus fruit flavanone. It is a TRPM3 channel blocker and CYP1 enzyme isoforms inhibitor. It is a strong candidate, as chemopreventive food ingredient against CYP1B1-related carcinogenesis. Isosakuranetin may be useful in treating neuropathic pain without body temperature increase. Isosakuranetin attenuated ethanol-induced gastritis by inhibiting the infiltration of immune cells, including neutrophils, via the regulation of CXCL4 (or IL-8) secretion and the activation NF-κB.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
transient receptor potential cation channel, subfamily M, member 3 1 Target ID: 226025.0 Gene Symbol: Trpm3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24006495 \| https://www.ncbi.nlm.nih.gov/pubmed/28720517	Blocker 555	50.0 nM [IC50]
Cytochrome P450 1A1 32 Target ID: CHEMBL2231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20696580	Inhibitor 8504	2.2 µM [IC50]
Cytochrome P450 1A2 73 Target ID: CHEMBL3356 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20696580	Inhibitor 8504	3.1 µM [IC50]
Cytochrome P450 1B1 4 Target ID: CHEMBL4878 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20696580	Inhibitor 8504	1.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Pain 619 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24006495 https://www.ncbi.nlm.nih.gov/pubmed/28715803	Primary	Preclinical	Unknown Approved Use Unknown
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20696580	Preventing	Basic research	Unknown Approved Use Unknown
Hemorrhagic gastritis 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28013186	Preventing	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Carboxymethylated cyclosophoraose as a novel chiral additive for the stereoisomeric separation of some flavonoids by capillary electrophoresis.	2010-11-02	20850110
Phenolic compounds in cherry ( Prunus avium ) heartwood with a view to their use in cooperage.	2010-04-28	20302370
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
Modulation of Akt, JNK, and p38 activation is involved in citrus flavonoid-mediated cytoprotection of PC12 cells challenged by hydrogen peroxide.	2009-03-25	19222219
Stereospecific high-performance liquid chromatographic assay of isosakuranetin in rat urine.	2008-11-01	18514595
Enantiomeric separation of some flavanones using shinorhizobial linear octasaccharides in CE.	2008-11	18924103
Chemical composition and botanical origin of red propolis, a new type of brazilian propolis.	2008-09	18830449
A validated reverse-phase HPLC analytical method for the quantification of phenolic compounds in Baccharis dracunculifolia.	2008-08-30	18752260
Antimicrobial activity of the extract and isolated compounds from Baccharis dracunculifolia D. C. (Asteraceae).	2008-04-05	18386486
Effects of propolis crude hydroalcoholic extract on chromosomal aberrations induced by doxorubicin in rats.	2007-12	17999350
A reliable quantitative method for the analysis of phenolic compounds in Brazilian propolis by reverse phase high performance liquid chromatography.	2007-11	17880032
Spray-dried propolis extract, II: prenylated components of green propolis.	2007-07	17718187
Enantioseparation of some chiral flavanones using microbial cyclic beta-(1-->3),(1-->6)-glucans as novel chiral additives in capillary electrophoresis.	2007-04-09	17234165
Effect of Baccharis dracunculifolia D.C. (Asteraceae) extracts and its isolated compounds on macrophage activation.	2007-03	17331351
[Studies on flavonoid constituents from herbs of Artemisia ordosica II].	2006-12	17348189
Separation of some chiral flavonoids by microbial cyclosophoraoses and their sulfated derivatives in micellar electrokinetic chromatography.	2005-10	16167311
In-vitro trypanocidal activity evaluation of crude extract and isolated compounds from Baccharis dracunculifolia D.C. (Asteraceae).	2004-09	15324490
Effect of Brazilian green propolis on the production of reactive oxygen species by stimulated neutrophils.	2004-09	15261964
Antioxidative bioavailability of artepillin C in Brazilian propolis.	2004-04-15	15047190
Separation of some chiral flavanones by micellar electrokinetic chromatography.	2003-08	12900864

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 2 or 10 mg/kg

Route of Administration: Intraperitoneal

In Vitro Use Guide

Isosakuranetin blocked the inward TRPM3 currents at -113 mV slightly more potently (IC50 = 80 nM) compared with the outward TRPM currents measured at -87 mV (IC50 = 120 nM). Both currents were isosakuranetin sensitive and almost completely blocked at a concentration of 3 uM.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:52:34 GMT 2025` Edited by `admin` on `Mon Mar 31 19:52:34 GMT 2025`
Record UNII	U02X7TF8UA
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

4'-METHYLNARINGENIN

Preferred Name

English

ISOSAKURANETIN

Common Name

English

(2S)-5,7-DIHYDROXY-2-(4-METHOXYPHENYL)-2,3-DIHYDROCHROMEN-4-ONE

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID60963980