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 537	50.0 nM [IC50]
Cytochrome P450 1A1 31 Target ID: CHEMBL2231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20696580	Inhibitor 8297	2.2 µM [IC50]
Cytochrome P450 1A2 72 Target ID: CHEMBL3356 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20696580	Inhibitor 8297	3.1 µM [IC50]
Cytochrome P450 1B1 4 Target ID: CHEMBL4878 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20696580	Inhibitor 8297	1.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24006495 https://www.ncbi.nlm.nih.gov/pubmed/28715803	Primary	Preclinical	Unknown Approved Use Unknown
Cancer 592 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
Separation of some chiral flavanones by micellar electrokinetic chromatography.	2003 Aug	12900864
Antioxidative bioavailability of artepillin C in Brazilian propolis.	2004 Apr 15	15047190
In-vitro trypanocidal activity evaluation of crude extract and isolated compounds from Baccharis dracunculifolia D.C. (Asteraceae).	2004 Sep	15324490
Effect of Brazilian green propolis on the production of reactive oxygen species by stimulated neutrophils.	2004 Sep	15261964
Separation of some chiral flavonoids by microbial cyclosophoraoses and their sulfated derivatives in micellar electrokinetic chromatography.	2005 Oct	16167311
[Studies on flavonoid constituents from herbs of Artemisia ordosica II].	2006 Dec	17348189
Enantioseparation of some chiral flavanones using microbial cyclic beta-(1-->3),(1-->6)-glucans as novel chiral additives in capillary electrophoresis.	2007 Apr 9	17234165
Effects of propolis crude hydroalcoholic extract on chromosomal aberrations induced by doxorubicin in rats.	2007 Dec	17999350
Spray-dried propolis extract, II: prenylated components of green propolis.	2007 Jul	17718187
Effect of Baccharis dracunculifolia D.C. (Asteraceae) extracts and its isolated compounds on macrophage activation.	2007 Mar	17331351
A reliable quantitative method for the analysis of phenolic compounds in Brazilian propolis by reverse phase high performance liquid chromatography.	2007 Nov	17880032
Antimicrobial activity of the extract and isolated compounds from Baccharis dracunculifolia D. C. (Asteraceae).	2008 Jan-Feb	18386486
Stereospecific high-performance liquid chromatographic assay of isosakuranetin in rat urine.	2008 Nov 1	18514595
A validated reverse-phase HPLC analytical method for the quantification of phenolic compounds in Baccharis dracunculifolia.	2009 Jan-Feb	18752260
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
Phenolic compounds in cherry ( Prunus avium ) heartwood with a view to their use in cooperage.	2010 Apr 28	20302370
Carboxymethylated cyclosophoraose as a novel chiral additive for the stereoisomeric separation of some flavonoids by capillary electrophoresis.	2010 Nov 2	20850110

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 `Fri Dec 15 19:39:40 GMT 2023` Edited by `admin` on `Fri Dec 15 19:39:40 GMT 2023`
Record UNII	U02X7TF8UA
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ISOSAKURANETIN

Common Name

English

4'-METHYLNARINGENIN

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