61303-13-7

Basic information

• Product Name: Isoacteoside
• Synonyms: Isokusaginin;Isoacteoside, >=98%;β-D-Glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl 3-O-(6-deoxy-α-L-mannopyranosyl)-, 6-[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoate];ISOVERBASCOSIDE;ISOACTEOSIDE;Isoacteosid;[(2R,3R,4S,5R,6R)-5-(3,4-Dihydroxyphenyl)-6-ethoxy-3,5-dihydroxy-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate;2-(3,4-Dihydroxyphenyl)ethyl 3-O-(α-L-rhamnopyranosyl)-6-O-[(E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]-β-D-glucopyranoside
• CAS NO: 61303-13-7
• Molecular Formula: C₂₉H₃₆O₁₅
• Molecular Weight: 624.59
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 61303-13-7.mol
• Article Data: 2

Chemical Properties

• Melting Point: 220～230℃
• Boiling Point: 940.2 °C at 760 mmHg
• Flash Point: 305.2 °C
• Appearance: /
• Density: 1.6 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.689
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 9.32±0.10(Predicted)
• CAS DataBase Reference: Isoacteoside(CAS DataBase Reference)
• NIST Chemistry Reference: Isoacteoside(61303-13-7)
• EPA Substance Registry System: Isoacteoside(61303-13-7)

Safety Data

• Hazardous Substances Data: 61303-13-7(Hazardous Substances Data)

Usage

Description

Isoverbascoside is a phenylethanoid glycoside that has been found in C. trichotomum and has diverse biological activities. It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; ) radicals in a cell-free assay and inhibits hydrogen peroxide-induced lipid peroxidation in V79-4 cells when used at a concentration of 10 μg/ml. Isoverbascoside (7.5-30 μM) induces apoptosis and production of reactive oxygen species (ROS) in, and reduces viability of, OVCAR-3 cells. It inhibits tumor growth in an OVCAR-3 mouse xenograft model when administered at a dose of 30 mg/kg. Isoverbascoside (2.5 and 5 mg/kg) decreases brain amyloid deposition and increases exploratory behavior in rats when infused into the cerebral ventricles with amyloid-β (1-42) (Aβ42; ). It also decreases xylene-induced ear edema in mice and increases survival in a mouse model of LPS-induced endotoxic shock.

Uses

Isoacteoside is a possible food antioxidant.

InChI:InChI=1/C29H36O15/c1-13-22(35)24(37)25(38)29(42-13)44-27-23(36)20(12-41-21(34)7-4-14-2-5-16(30)18(32)10-14)43-28(26(27)39)40-9-8-15-3-6-17(31)19(33)11-15/h2-7,10-11,13,20,22-33,35-39H,8-9,12H2,1H3/b7-4+/t13-,20+,22-,23+,24+,25+,26+,27-,28+,29-/m0/s1

Upstream product

• 61276-17-3 Acteoside 

Downstream Products

• 83529-65-1 isoacteoside peracetate 
• 61548-34-3 decaffeoyl verbascoside 
• 5396-64-5 methyl (E)-3-(3,4-dimethoxyphenyl)acrylate 
• 2280-44-6 D-Glucose 
• 73-34-7 L-rhamnose 

Relevant articles and documents

Antioxidative activities of phenylethanoid glycosides from Ligustrum purpurascens

Tea and kudingcha (bitter tea) are the two most popular beverages consumed in China. Tea derived from the leaves of Camellia sinensis has been well studied for its various health benefits, but there are very limited data on the biological activities of bitter tea derived from the leaves of Ligustrum purpurascens (LP). The present study was carried out to characterize the antioxidants present in the bitter tea brewed from the leaves of LP. It was found that the crude glycoside fraction possessed strong protection against oxidation of human low-density lipoprotein (LDL). The column chromatographic separation led to the isolatation of five phenylethanoid glycosides, namely, acteoside, ligupurpuroside A, cis-ligupurpuroside B, trans-ligupurpuroside B, and osmanthuside B. When acteoside was heated in the boiling water, it was isomerized to form isoacteoside. Acteoside, isoacteoside, and ligupurpuroside A purified from LP were protective, whereas cis-ligupurpuroside B, trans-ligupurpuroside B, and osmanthuside B exhibited no protection to human LDL from Cu2+-medicated oxidation. Acteoside, isoacteoside, and ligupurpuroside A were also effective in preventing the peroxyl free radical-induced oxidation of α-tocopherol in human LDL. The antioxidant activities of acteoside, isoacteoside, and ligupurpuroside A were comparable to that observed for a green tea antioxidant, (-)-epicatechin gallate. The inhibitory effect of these three phenylethanoid glycosides on oxidation of human LDL and α-tocopherol was dose-dependent at concentrations of 5-40 μM. The present results suggest that the bitter tea beverage derived from LP contains effective antioxidants that may have an equal benefit as a green tea beverage.