sakuranetin
(S)-4',5-dihydroxy-7-methoxyflavone
Identification
| Name | sakuranetin |
| IUPAC | (2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydrochromen-4-one |
| CAS Number | 2957-21-3 |
| EINECS | 220-980-5 |
| FDA UNII | 3O38P61299 |
| Molecular Formula | C16 H14 O5 |
| Molecular Weight | 286.28358000 |
| MDL Number | MFCD00075651 |
| Nikkaji Number | J7.652J |
| Beilstein | 0092466 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 152.00 °C. @ 760.00 mm Hg |
| Boiling Point | 555.90 °C. @ 760.00 mm Hg (est) |
| Flash Point | 414.00 °F. TCC ( 212.40 °C. ) (est) |
| logP (o/w) | 3.370 (est) |
| Soluble in | water, 109.2 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for sakuranetin usage levels up to | not for fragrance use. |
| Recommendation for sakuranetin flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
4H-1-
benzopyran-4-one, 2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-, (2S)-
4H-1-
benzopyran-4-one, 2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-, (S)- (9CI)
(2S)-2,3-
dihydro-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one
(S)-2,3-
dihydro-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one
(S)-(-)-4',5-
dihydroxy-7-methoxyflavanone
(S)-4',5-
dihydroxy-7-methoxyflavanone
(S)-4',5-
dihydroxy-7-methoxyflavone
(2S)-5-
hydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-4H-chromen-4-one
(2S)-5-
hydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydrochromen-4-one
(2S)-5-
hydroxy-2-(4-hydroxyphenyl)-7-methoxy-chroman-4-one
7-O-
methylnaringenin
naringenin 7-O-methyl ether
(-)-(S)-
sakuranetin
(2S)-
sakuranetin
PubMed:
Analysis on blast fungus-responsive characters of a flavonoid phytoalexin sakuranetin; accumulation in infected rice leaves, antifungal activity and detoxification by fungus.
PubMed:
Structural crystalline characterization of sakuranetin--an antimicrobial flavanone from twigs of Baccharis retusa (Asteraceae).
PubMed:
The potential bioproduction of the pharmaceutical agent sakuranetin, a flavonoid phytoalexin in rice.
PubMed:
Purification and identification of naringenin 7-O-methyltransferase, a key enzyme in biosynthesis of flavonoid phytoalexin sakuranetin in rice.
PubMed:
A nicotinic receptor-mediated anti-inflammatory effect of the flavonoid rhamnetin in BV2 microglia.
PubMed:
A flavanone from Baccharis retusa (Asteraceae) prevents elastase-induced emphysema in mice by regulating NF-κB, oxidative stress and metalloproteinases.
PubMed:
Transcriptomic analysis of UV-treated rice leaves reveals UV-induced phytoalexin biosynthetic pathways and their regulatory networks in rice.
PubMed:
Biosynthesis of bioactive O-methylated flavonoids in Escherichia coli.
PubMed:
Sakuranetin induces adipogenesis of 3T3-L1 cells through enhanced expression of PPARgamma2.
PubMed:
Flavonone treatment reverses airway inflammation and remodelling in an asthma murine model.
PubMed:
Ethanol extract and isolated constituents from artemisia dracunculus inhibit esophageal squamous cell carcinoma and induce apoptotic cell death.
PubMed:
Antimicrobial activity of UV-induced phenylamides from rice leaves.
PubMed:
A methyltransferase for synthesis of the flavanone phytoalexin sakuranetin in rice leaves.
PubMed:
Stereospecific analysis of sakuranetin by high-performance liquid chromatography: pharmacokinetic and botanical applications.
PubMed:
Naringenin 7-O-methyltransferase involved in the biosynthesis of the flavanone phytoalexin sakuranetin from rice (Oryza sativa L.).
PubMed:
Multiple phytohormones and phytoalexins are involved in disease resistance to Magnaporthe oryzae invaded from roots in rice.
PubMed:
Effects of chemopreventive natural products on non-homologous end-joining DNA double-strand break repair.
PubMed:
In vitro antileishmanial and antitrypanosomal activities of flavanones from Baccharis retusa DC. (Asteraceae).
PubMed:
[Derivations from asebotin to sakuranetin and from phlorizin to naringenin].
PubMed:
Biosynthesis of phytoalexins and regulatory mechanisms of it in rice.
PubMed:
[Chemical constituents contained in Populus tomentosa].
PubMed:
Isoprenylated flavonoid and adipogenesis-promoting constituents of Dodonaea viscosa.
PubMed:
Transcriptome Analysis of Early Responsive Genes in Rice during Magnaporthe oryzae Infection.
PubMed:
OsJAR1 contributes mainly to biosynthesis of the stress-induced jasmonoyl-isoleucine involved in defense responses in rice.
PubMed:
Measurement of the influence of flavonoids on DNA repair kinetics using the comet assay.
PubMed:
In vitro evaluation of flavonoids from Eriodictyon californicum for antagonist activity against the bitterness receptor hTAS2R31.
PubMed:
Prunus yedoensis bark inhibits lipopolysaccharide-induced inflammatory cytokine synthesis by IκBα degradation and MAPK activation in macrophages.
PubMed:
Evaluation of estrogen receptor Beta binding of pruni cortex and its constituents.
PubMed:
Biflavonoids from Caper (Capparis spinosa L.) fruits and their effects in inhibiting NF-kappa B activation.
PubMed:
Transport mechanisms of flavanone aglycones across Caco-2 cell monolayers and artificial PAMPA membranes.
PubMed:
Identification of rice Allene Oxide Cyclase mutants and the function of jasmonate for defence against Magnaporthe oryzae.
PubMed:
Three flavonoids targeting the beta-hydroxyacyl-acyl carrier protein dehydratase from Helicobacter pylori: crystal structure characterization with enzymatic inhibition assay.
PubMed:
Thymus mastichina: chemical constituents and their anti-cancer activity.
PubMed:
Production of 7-O-methyl aromadendrin, a medicinally valuable flavonoid, in Escherichia coli.
PubMed:
A convenient method for simultaneous quantification of multiple phytohormones and metabolites: application in study of rice-bacterium interaction.
PubMed:
Spasmolytic effects of Scrophularia nodosa extract on isolated rabbit intestine.
PubMed:
Interconverting flavanone glucosides and other phenolic compounds in Lippia salviaefolia Cham. ethanol extracts.
PubMed:
Investigation of the extraction process and phytochemical composition of preparations of Dodonaea viscosa (L.) Jacq.
PubMed:
Qualitative variation of anti-diabetic compounds in different tarragon (Artemisia dracunculus L.) cytotypes.
PubMed:
Effects of naturally occurring dihydroflavonols from Inula viscosa on inflammation and enzymes involved in the arachidonic acid metabolism.
PubMed:
Methionine-induced phytoalexin production in rice leaves.
PubMed:
Phytoalexin production by amino acid conjugates of jasmonic acid through induction of naringenin-7-O-methyltransferase, a key enzyme on phytoalexin biosynthesis in rice (Oryza sativa L.).
PubMed:
Reversal of multidrug resitance by natural substances from plants.
PubMed:
Smooth muscle relaxing compounds from Dodonaea viscosa.
PubMed:
Coronatine elicits phytoalexin production in rice leaves (Oryza sativa L.) in the same manner as jasmonic acid.
PubMed:
Antifungal activity of Heterothalamus alienus metabolites.
PubMed:
Antifungal flavanones and prenylated hydroquinones from Piper crassinervium Kunth.
PubMed:
O-demethylation and sulfation of 7-methoxylated flavanones by Cunninghamella elegans.
PubMed:
Differential expression of defense/stress-related marker proteins in leaves of a unique rice blast lesion mimic mutant (blm).
PubMed:
The rice (Oryza sativa) blast lesion mimic mutant, blm, may confer resistance to blast pathogens by triggering multiple defense-associated signaling pathways.
PubMed:
[Studies on chemical constitutes of Phellinus igniarius].
PubMed:
Effects of selected flavonoids and carotenoids on drug accumulation and apoptosis induction in multidrug-resistant colon cancer cells expressing MDR1/LRP.
PubMed:
Regiospecific flavonoid 7-O-methylation with Streptomyces avermitilis O-methyltransferase expressed in Escherichia coli.
PubMed:
Allergy-preventive flavonoids from Xanthorrhoea hastilis.
PubMed:
Isolation and molecular characterization of a Spotted leaf 18 mutant by modified activation-tagging in rice.
PubMed:
Anti-inflammatory activity of flavonoids from Populus davidiana.
PubMed:
Antimycobacterial agents from selected Mexican medicinal plants.
PubMed:
Methoxylated flavonols and flavanones from Eupatorium odoratum.
PubMed:
Enantioseparation of some chiral flavanones using microbial cyclic beta-(1-->3),(1-->6)-glucans as novel chiral additives in capillary electrophoresis.
PubMed:
Separation of some chiral flavonoids by microbial cyclosophoraoses and their sulfated derivatives in micellar electrokinetic chromatography.
PubMed:
Cyclohexanoid protoflavanones from the stem-bark and roots of Ongokea gore.
PubMed:
Induced volatiles in elicitor-treated and rice blast fungus-inoculated rice leaves.
PubMed:
Anti-inflammatory cyclohexenyl chalcone derivatives in Boesenbergia pandurata.
PubMed:
A C-glucosylflavone from leaves of Piper lhotzkyanum.
PubMed:
Phenolic compounds from Eucalyptus maculata.
PubMed:
Synthesis of 7-methoxyapigeninidin and its fungicidal activity against Gloeocercospora sorghi.
PubMed:
Cytotoxic and antibacterial dihydrochalcones from Piper aduncum.
PubMed:
Isolation of potential cancer chemopreventive agents from Eriodictyon californicum.
PubMed:
[Flavonoids of Artemisia campestris, ssp. glutinosa].