84687-42-3

Basic information

• Product Name: Astragaloside III
• Synonyms: Astragaloside III;Astragaloside-Ⅲ;β-D-Xylopyranoside,(3β,6α,16β,20R,24S)-20,24-epoxy-6,16,25-trihydroxy-9,19-cyclolanostan-3-yl2-O-β-D-glucopyranosyl-;ASTRAGALOSIDE III(SH)
• CAS NO: 84687-42-3
• Molecular Formula: C₄₁H₆₈O₁₄
• Molecular Weight: 784.974
• Product Categories: The group of Astralosides;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 84687-42-3.mol
• Article Data: 2

Chemical Properties

• Melting Point: 245～247℃
• Boiling Point: 906.8 °C at 760 mmHg
• Flash Point: 502.2 °C
• Appearance: /
• Density: 1.39 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.62
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Methanol (Slightly), Pyridine (Slightly)
• PKA: 12.89±0.70(Predicted)
• CAS DataBase Reference: Astragaloside III(CAS DataBase Reference)
• NIST Chemistry Reference: Astragaloside III(84687-42-3)
• EPA Substance Registry System: Astragaloside III(84687-42-3)

Safety Data

• Hazardous Substances Data: 84687-42-3(Hazardous Substances Data)

Usage

Description

Astragaloside III is a saponin first isolated from the dried plant roots of the genus Astragalus, which is used in traditional Chinese medicine. It is bioavailable after oral administration, distributed mainly to the thymus and spleen, and has a half-life of approximately 2 hours.

Uses

Astragaloside III has cardioprotective effects as well as causing improvement in cognitive function. Used in the prevention of cardio-cerebral vascular diseases. Antioxidant.

Definition

ChEBI: A triterpenoid saponin that is cycloastragenol with a 2-O-beta-D-glucopyranosyl-beta-D-xylopyranosyl moiety attached at position 3 via a glycosidic linkage.

InChI:InChI=1/C41H68O14/c1-35(2)24(53-34-30(26(46)21(45)17-51-34)54-33-29(49)28(48)27(47)22(16-42)52-33)9-11-41-18-40(41)13-12-37(5)32(39(7)10-8-25(55-39)36(3,4)50)20(44)15-38(37,6)23(40)14-19(43)31(35)41/h19-34,42-50H,8-18H2,1-7H3/t19-,20-,21+,22+,23-,24-,25-,26-,27+,28-,29+,30+,31-,32-,33-,34-,37+,38-,39+,40-,41+/m0/s1

Upstream product

• 133-89-1 UDP-glucose 
• 86541-83-5 cyclosieversigenin 3-O-β-D-xylopyranoside 
• 3616-06-6 UDP-xylose 
• 84605-18-5 cycloastragenol 
• 84687-44-5 astragaloside V 

Downstream Products

• 84605-18-5 cycloastragenol 
• 86541-83-5 cyclosieversigenin 3-O-β-D-xylopyranoside 

Relevant articles and documents

Functional Characterization and Protein Engineering of a Triterpene 3-/6-/2′-O-Glycosyltransferase Reveal a Conserved Residue Critical for the Regiospecificity

Engineering the function of triterpene glucosyltransferases (GTs) is challenging due to the large size of the sugar acceptors. In this work, we identified a multifunctional glycosyltransferase AmGT8 catalyzing triterpene 3-/6-/2′-O-glycosylation from the medicinal plant Astragalus membranaceus. To engineer its regiospecificity, a small mutant library was built based on semi-rational design. Variants A394F, A394D, and T131V were found to catalyze specific 6-O, 3-O, and 2′-O glycosylation, respectively. The origin of regioselectivity of AmGT8 and its A394F variant was studied by molecular dynamics and hydrogen deuterium exchange mass spectrometry. Residue 394 is highly conserved as A/G and is critical for the regiospecificity of the C- and O-GTs TcCGT1 and GuGT10/14. Finally, astragalosides III and IV were synthesized by mutants A394F, T131V and P192E. This work reports biocatalysts for saponin synthesis and gives new insights into protein engineering of regioselectivity in plant GTs.