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Galloylpaeoniflorin

$896

  • Brand : BIOFRON

  • Catalogue Number : BD-P0210

  • Specification : 98.0%(HPLC)

  • CAS number : 122965-41-7

  • PUBCHEM ID : 101604718

  • Volume : 25mg

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Catalogue Number

BD-P0210

Analysis Method

HPLC,NMR,MS

Specification

98.0%(HPLC)

Storage

2-8°C

Molecular Weight

Appearance

White crystalline powder

Botanical Source

Paeonia lactiflora

Structure Type

Monoterpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC12CC3(C4CC1(C4(C(O2)O3)COC(=O)C5=CC=CC=C5)OC6C(C(C(C(O6)COC(=O)C7=CC(=C(C(=C7)O)O)O)O)O)O)O

Synonyms

[(1R,2S,3R,5R,6R,8S)-6-Hydroxy-8-methyl-3-{[6-O-(3,4,5-trihydroxybenzoyl)-β-D-glucopyranosyl]oxy}-9,10-dioxatetracyclo[4.3.1.0.0]dec-2-yl]methyl benzoate/((2R,3S,4S,5R,6S)-6-(((1aR,1a1S,2R,3aR,5S,5aR)-1a1-((benzoyloxy)methyl)-2-hydroxy-5-methyltetrahydro-1H-3,4-dioxa-2,5-methanocyclobuta[cd]pentalen-5a(5H)-yl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methyl 3,4,5-trihydroxybenzoate/β-D-Glucopyranoside, (1aR,2S,3aR,5R,5aR,5bS)-5b-[(benzoyloxy)methyl]tetrahydro-5-hydroxy-2-methyl-2,5-methano-1H-3,4-dioxacyclobuta[cd]pentalen-1a(2H)-yl, 6-(3,4,5-trihydroxybenzoate)/Galloylpaeoniflorin/6'-O-Galloyl paeoniflorin

IUPAC Name

[(2R,3S,4S,5R,6S)-6-[[(1R,2S,3R,5R,6R,8S)-2-(benzoyloxymethyl)-6-hydroxy-8-methyl-9,10-dioxatetracyclo[4.3.1.02,5.03,8]decan-3-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate

Applications

Platelet anti-aggregatory and blood anti-coagulant effects of compounds isolated from Paeonia lactiflora and Paeonia suffruticosa. PUMID/DOI:20824965 Pharmazie. 2010 Aug;65(8):624-8. Eighteen compounds, which have been reported to be present in both plant medicines, were evaluated for their effects on platelet aggregation and blood coagulation. Paeonol (5), paeoniflorin (9), benzoylpaeoniflorin (11), and benzoyloxypaeoniflorin (12) were found to be the major common active constituents and they would collectively contribute to improving blood circulation through their inhibitory effects on both platelet aggregation and blood coagulation. In addition, methylgallate (4), (+)-catechin (7), paeoniflorigenone (8), Galloylpaeoniflorin (13), and daucosterol (16) may also take part in improving blood circulation by inhibiting ether platelet aggregation and/or blood coagulation. 6'-o-galloylpaeoniflorin protects human keratinocytes against oxidative stress-induced cell damage. PUMID/DOI:24244822 Biomol. Ther., 2013, 21(5):349-57. 6'-O-Galloyl paeoniflorin (GPF) is a galloylated derivate of paeoniflorin and a key chemical constituent of the peony root, a perennial flowering plant that is widely used as an herbal medicine in East Asia. This study is the first investigation of the cytoprotective effects of GPF against hydrogen peroxide (H2O2)-induced cell injury and death in human HaCaT keratinocytes. GPF demonstrated a significant scavenging capacity against the 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical, H2O2-generated intracellular reactive oxygen species (ROS), the superoxide anion radical (O2 (-)), and the hydroxyl radical (OH). GPF also safeguarded HaCaT keratinocytes against H2O2-provoked apoptotic cell death and attenuated oxidative macromolecular damage to DNA, lipids, and proteins. The compound exerted its cytoprotective actions in keratinocytes at least in part by decreasing the number of DNA strand breaks, the levels of 8-isoprostane (a stable end-product of lipid peroxidation), and the formation of carbonylated protein species. Taken together, these results indicate that GPF may be developed as a cytoprotector against ROS-mediated oxidative stress. Androgen modulators from the roots of Paeonia lactiflora (paeoniae radix) grown and processed in nara prefecture, Japan. PUMID/DOI:19721258 Chem. Pharm. Bull., 2009, 57(9):971-4. The monoterpene glycoside, 3'-O-galloylpaeoniflorin (1), and four known compounds, 6'-O-galloylalbiflorin (2), pentagalloylglucose (3), 6'-O-benzoylpaeoniflorin (4) and 6'-O-Galloyl paeoniflorin (5), were isolated from the roots of Paeonia lactiflora that had been grown and processed in Nara prefecture, Japan, as androgen modulators. Their structures were elucidated based on spectroscopic analysis. Compounds 2 and 3 showed strong androgen receptor (AR) binding activity (IC(50) values 33.7 and 4.1 microg/ml, respectively), 1, 4 and 5 showed weak activity (20, 31 and 12% at 120 microg/ml, respectively). However, paeoniflorin (6) and albiflorin (7), the structures of which are related to 1, 2, 4 and 5, showed no activity. These results suggested that both the structure of albiflorin and the galloyl moiety are important for 2 to show strong AR binding activity. Furthermore, compounds 1-5 inhibited growth of an androgen-dependent LNCaP-FGC (prostate cancer cell line), and were indicated to be AR antagonists. Compounds 2 and 3 might be candidates as safe, natural anti-androgens.

Density

1.7±0.1 g/cm3

Solubility

Methanol; Water

Flash Point

290.8±27.8 °C

Boiling Point

887.7±65.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C30H32O15/c1-27-11-29(39)18-9-30(27,28(18,26(44-27)45-29)12-41-23(37)13-5-3-2-4-6-13)43-25-22(36)21(35)20(34)17(42-25)10-40-24(38)14-7-15(31)19(33)16(32)8-14/h2-8,17-18,20-22,25-26,31-36,39H,9-12H2,1H3/t17-,18-,20-,21+,22-,25+,26-,27+,28+,29-,30+/m1/s1

InChl Key

KLFIUQCKSSAFFU-UHFFFAOYSA-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#:122965-41-7) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

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