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Isosakuranetin

$250

  • Brand : BIOFRON

  • Catalogue Number : BF-I4005

  • Specification : 98%(HPLC)

  • CAS number : 480-43-3

  • Formula : C16H14O5

  • Molecular Weight : 286.28

  • PUBCHEM ID : 160481

  • Volume : 25mg

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Catalogue Number

BF-I4005

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

2-8°C

Molecular Weight

286.28

Appearance

Yellow crystalline powder

Botanical Source

Clinopodium chinense,Citrus aurantium,Elsholtzia eriostachya,Ilex centrochinensis,Murraya euchrestifolia

Structure Type

Flavonoids

Category

Standards;Natural Pytochemical;API

SMILES

COC1=CC=C(C=C1)C2CC(=O)C3=C(C=C(C=C3O2)O)O

Synonyms

iso-Sakuranetin/5,7-DIHYDROXY-4'-METHOXYFLAVANONE/Isosakurametin/4'-Methylnaringenin/Citrifoliol/4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-methoxyphenyl)-, (2S)-/Isosakuranetin/Kikokunetin/Angophorol/(2S)-5,7-Dihydroxy-2-(4-methoxyphenyl)-2,3-dihydro-4H-chromen-4-one/naringenin 4'-methyl ether/isokaurentin/4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-methoxyphenyl)-, (S)-/4'-methoxy-5,7-dihydroxyflavanone

IUPAC Name

(2S)-5,7-dihydroxy-2-(4-methoxyphenyl)-2,3-dihydrochromen-4-one

Density

1.4±0.1 g/cm3

Solubility

Methanol; Ethanol; Ethyl Acetate

Flash Point

205.6±23.6 °C

Boiling Point

539.2±50.0 °C at 760 mmHg

Melting Point

193-194ºC

InChl

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

InChl Key

HMUJXQRRKBLVOO-AWEZNQCLSA-N

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:480-43-3) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

28715803

Abstract

Chronic pain remains a challenging clinical reality, yet currently available analgesics are insufficient to meet clinical needs. Increasing attention has been paid to bioactive compounds from natural plants, which may be efficacious against pain. This study examined the antinociceptive effects of isosakuranetin, a plant-derived transient receptor potential melastatin 3 blocker, in a rat model of peripheral neuropathy. Adult male Sprague-Dawley rats were first allowed to go through the chronic constriction injury surgery to develop neuropathic pain. They were then treated with isosakuranetin (1.5, 3, or 6 mg/kg) intraperitoneally and the effects on mechanical, thermal, and cold hyperalgesia were assessed using the von Frey filament test, Hargreaves’ plantar test, and cold plate test, respectively. Isosakuranetin dose-dependently alleviated mechanical, thermal, and cold hyperalgesia and the antinociceptive potency was similar across the assays. In the rotarod test, isosakuranetin did not significantly affect motor performance within the doses tested, confirming the antinociceptive specificity. In summary, these findings suggest that isosakuranetin may be useful in treating neuropathic pain and deserves further investigation.
© 2017 S. Karger AG, Basel.

KEYWORDS

Chronic constriction injury; Hyperalgesia; Isosakuranetin; Neuropathic pain; Rats; Rotarod test

Title

Antinociceptive Effects of Isosakuranetin in a Rat Model of Peripheral Neuropathy.

Author

Jia S1, Zhang Y, Yu J.

Publish date

2017

PMID

27598131

Abstract

Solar ultraviolet (UV) radiation is a main extrinsic factor for skin aging. Chronic exposure of the skin to UV radiation causes the induction of matrix metalloproteinases (MMPs), such as MMP-1, and consequently results in alterations of the extracellular matrix (ECM) and skin photoaging. Flavonoids are considered as potent anti-photoaging agents due to their UV-absorbing and antioxidant properties and inhibitory activity against UV-mediated MMP induction. To identify anti-photoaging agents, in the present study we examined the preventative effect of methoxyflavonoids, such as sakuranetin, isosakuranetin, homoeriodictyol, genkwanin, chrysoeriol and syringetin, on UV-B-induced skin photo-damage. Of the examined methoxyflavonoids, pretreatment with isosakuranetin strongly suppressed the UV-B-mediated induction of MMP-1 in human keratinocytes in a concentration-dependent manner. Isosakuranetin inhibited UV-B-induced phosphorylation of mitogen-activated protein kinase (MAPK) signaling components, ERK1/2, JNK1/2 and p38 proteins. This result suggests that the ERK1/2 kinase pathways likely contribute to the inhibitory effects of isosakuranetin on UV-induced MMP-1 production in human keratinocytes. Isosakuranetin also prevented UV-B-induced degradation of type-1 collagen in human dermal fibroblast cells. Taken together, our findings suggest that isosakuranetin has the potential for development as a protective agent for skin photoaging through the inhibition of UV-induced MMP-1 production and collagen degradation.

KEYWORDS

MMP-1; UV-B-radiation; anti-photoaging; isosakuranetin; methoxyflavonoid

Title

The Methoxyflavonoid Isosakuranetin Suppresses UV-B-Induced Matrix Metalloproteinase-1 Expression and Collagen Degradation Relevant for Skin Photoaging.

Author

Jung H1, Lee EH2, Lee TH3, Cho MH4.

Publish date

2016 Sep 1

PMID

26524968

Abstract

AIMS:
The beneficial effects of 4′-O-methylated flavonoids on induction of melanogenesis are well established. Here, we report the effect of isosakuranetin (Iso) on melanogenesis in B16BL6 melanoma cells and an analysis of the signaling pathways involved in this activity.
METHODS:
B16BL6 melanoma cells were treated with several concentrations of Iso and melanin content was measured. Activation and expression of factors involved in melanogenesis were assessed via western blotting.
KEY FINDINGS:
Iso (15 and 30μmol/L) strongly stimulated melanogenesis in a dose-dependent manner. Iso increased tyrosinase activity and up-regulated tyrosinase (Tyr), tyrosinase related protein 1 (TRP1), and tyrosinase related protein 2 (TRP2) in a time-dependent manner. Iso decreased B16 cell proliferation at a concentration above 45μmol/L, and had no effect on cell viability as revealed by MTT and trypan blue assays. Iso up-regulated expression of microphthalmia transcription factor (MITF), with a maximum effect after 12h. H89, a specific inhibitor of PKA, showed that MITF up-regulation is mediated through PKA/CREB activation. Furthermore, Iso decreased phosphorylation of MITF at Ser73 after 24h and 48h of exposure, activating MITF and leading to up-regulation of Tyr, TRP1, and TRP2. Iso inhibited phosphorylation and activation of ERK1/2 after 12h, while no significant effects on p38 and JNK phosphorylation were observed. Iso inhibited AKT phosphorylation and led to activation of GSK3β.
SIGNIFICANCE:
Iso stimulates melanogenesis in B16 melanoma cells via up-regulation of MITF. Furthermore, Iso-induced inhibition of ERK1/2 and PI3K/AKT signaling pathways activate MITF and subsequent expression of Tyr, TRP1, and TRP2.
Copyright © 2015 Elsevier Inc. All rights reserved.

KEYWORDS

Flavonoid; Isosakuranetin; Melanogenesis; Mitf; TRP1; TRP2; Tyr

Title

Isosakuranetin, a 4'-O-methylated flavonoid, stimulates melanogenesis in B16BL6 murine melanoma cells.

Author

Drira R1, Sakamoto K2.

Publish date

2015 Dec 15


Description :

Isosakuranetin is a flavanone flavonoid which can be found in the fruit of Citrus bergamia.