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
MSDS
28715803
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.
Chronic constriction injury; Hyperalgesia; Isosakuranetin; Neuropathic pain; Rats; Rotarod test
Antinociceptive Effects of Isosakuranetin in a Rat Model of Peripheral Neuropathy.
Jia S1, Zhang Y, Yu J.
2017
27598131
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.
MMP-1; UV-B-radiation; anti-photoaging; isosakuranetin; methoxyflavonoid
The Methoxyflavonoid Isosakuranetin Suppresses UV-B-Induced Matrix Metalloproteinase-1 Expression and Collagen Degradation Relevant for Skin Photoaging.
Jung H1, Lee EH2, Lee TH3, Cho MH4.
2016 Sep 1
26524968
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.
Flavonoid; Isosakuranetin; Melanogenesis; Mitf; TRP1; TRP2; Tyr
Isosakuranetin, a 4'-O-methylated flavonoid, stimulates melanogenesis in B16BL6 murine melanoma cells.
Drira R1, Sakamoto K2.
2015 Dec 15
Description :
Isosakuranetin is a flavanone flavonoid which can be found in the fruit of Citrus bergamia.
