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Camelliaside B

$672

  • Brand : BIOFRON

  • Catalogue Number : BD-P0165

  • Specification : 98.5%(HPLC)

  • CAS number : 131573-90-5

  • Formula : C32H38O19

  • Molecular Weight : 726.6

  • PUBCHEM ID : 25115190

  • Volume : 25mg

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Catalogue Number

BD-P0165

Analysis Method

HPLC,NMR,MS

Specification

98.5%(HPLC)

Storage

2-8°C

Molecular Weight

726.6

Appearance

Camellia oleifera Abel.

Botanical Source

Structure Type

Flavonoids

Category

SMILES

CC1C(C(C(C(O1)OC2C(C(OC(C2OC3C(C(C(CO3)O)O)O)OC4=C(OC5=CC(=CC(=C5C4=O)O)O)C6=CC=C(C=C6)O)CO)O)O)O)O

Synonyms

5,7-dihydroxy-3-[(2R,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-2-(4-hydroxyphenyl)chromen-4-one

IUPAC Name

3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

Applications

Density

1.8±0.1 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

336.2±27.8 °C

Boiling Point

1058.6±65.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C32H38O19/c1-10-19(38)23(42)25(44)31(46-10)49-27-21(40)17(8-33)48-32(29(27)51-30-24(43)20(39)15(37)9-45-30)50-28-22(41)18-14(36)6-13(35)7-16(18)47-26(28)11-2-4-12(34)5-3-11/h2-7,10,15,17,19-21,23-25,27,29-40,42-44H,8-9H2,1H3/t10-,15+,17+,19-,20-,21+,23+,24+,25+,27-,29+,30-,31-,32+/m0/s1

InChl Key

MVXYVHBRCFDZCJ-IRIIMWQRSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:131573-90-5) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

27015590

Abstract

Accumulating evidence suggested that soluble oligomeric β-amyloid protein (Aβ) exerts diverse roles in neuronal cell death, neuroinflammation, oxidative stress, and the eventual dementia associated with Alzheimer’s disease (AD). Developing an agent with multiple properties may be a reasonable strategy for the treatment of AD. In this study, we isolated a novel multifunctional compound named camellikaempferoside B (YCF-2) from Fuzhuan brick tea. YCF-2 consists of kaempferol backbone, p-coumaric acid (p-CA) group, and a novel structure of rhamnopyranosyl group at the C-4′ position, possessing the properties of both kaempferol and p-CA. YCF-2 significantly inhibited Aβ production by decreasing β-secretase activity. Moreover, YCF-2 suppressed Aβ42 fibrillation and facilitated nontoxic oligomer formation by binding to Aβ42 oligomers and by blocking the conformational transition to β-sheet. Furthermore, YCF-2 ameliorated Aβ-induced neuronal cell death, ROS production, inflammatory factor release, and microglia activation by blocking the NF-κB signaling pathway in microglia. These findings indicated that YCF-2 with a novel lead structure has potential applications for drug development for AD treatment.

KEYWORDS

Amyloid-beta; aggregation; camellikaempferoside B; microglia; neurotoxicity; β-secretase.

Title

A Novel Multifunctional Compound Camellikaempferoside B Decreases Aβ Production, Interferes with Aβ Aggregation, and Prohibits Aβ-Mediated Neurotoxicity and Neuroinflammation

Author

Shigao Yang 1, Wen Liu 1 2, Shuai Lu 1, Yong-zhen Tian 3, Wei-yun Wang 2, Tie-jun Ling 3, Rui-tian Liu 1

Publish date

2016 Apr 20

PMID

22777867

Abstract

Background: The application of tea seed extract (TSE) has been widely investigated owing to its biological activities. In this paper, two flavonol triglycosides found in TSE, camelliaside A (CamA) and camelliaside B (CamB), were subjected to hydrolysis in the presence of three commercial enzyme complexes of the Pectinex® series, 5XL, XXL and Ultra SP-L (Ultra).

Results: XXL and 5XL induced stepwise deglycosylation of CamA and CamB to yield kaempferol diglycoside (nicotiflorin), kaempferol monoglycoside (astragalin) and kaempferol, while Ultra produced an additional new compound (1) that had not been observed in earlier studies. Upon hydrolysis of isolated CamA and CamB, compound (1) was obtained only from CamB. Both the molecular ion peak in liquid chromatography/mass spectrometry and the ¹H and ¹³C nuclear magnetic resonance spectra of (1) isolated by Ultra-induced hydrolysis of TSE indicated that (1) was kaempferol 3-O-β-xylopyranosyl (1 → 2)-β-glucopyranoside (leucoside), formed by selective hydrolysis of the rhamnosyl moiety of CamB.

Conclusion: Pure leucoside can be prepared by enzymatic partial hydrolysis of TSE. This is the first study to address the synthesis of pure leucoside from a natural source.

Copyright © 2012 Society of Chemical Industry.

Title

Novel synthesis of leucoside by enzymatic hydrolysis of tea seed extract

Author

Dae-won Chung 1, Seul Bi Lee

Publish date

2013 Jan;

PMID

21567414

Abstract

Background: The application of tea seed extract (TSE) has been widely investigated because of its biological activities. In this paper, two flavonol triglycosides in TSE-camelliaside A (CamA) and camelliaside B (CamB)-were subjected to hydrolysis in the presence of two commercial enzyme complexes (Pectinex™ series): Smash and Mash.

Results: Smash hydrolyzed only the xylosyl moiety of CamB, and the main product was kaempferol diglycoside (nicotiflorin, NF). On the other hand, Mash induced the hydrolysis of both CamA and CamB, and kaempferol monoglycoside (astragalin, AS) was found to be a main product. Pure AS with > 96% purity was prepared by enzymatic hydrolysis of TSE using Mash, and the chemical structure of AS was confirmed by (1)H- and (13)C-nuclear magnetic resonance analyses. The prepared pure AS showed anti-inflammatory activities by significantly inhibiting cellular nitrite oxide (IC(50) = 363 µg mL(-1)), prostaglandin E(2) (IC(50) = 134 µg mL(-1)) and interleukin-6 production (IC(50) = 289 µg mL(-1)) by lipopolysaccharide -stimulated RAW 264.7 cells.

Conclusion: It was concluded that pure AS can be prepared by enzymatic partial hydrolysis of TSE and employed as an anti-inflammatory material. This is the first study to address the preparation of pure AS from natural sources.

Copyright © 2011 Society of Chemical Industry.

Title

Isolation and anti-inflammatory effect of astragalin synthesized by enzymatic hydrolysis of tea seed extract

Author

Hyang-Bok Lee 1, Eun-Ki Kim, Sang-Jae Park, Sang-gu Bang, Tae Gil Kim, Dae-won Chung

Publish date

2011 Oct