61276-17-3

Basic information

• Product Name: Verbascoside
• Synonyms: glucopyranoside,2-(3,4-dihydroxyphenyl)ethyl3-o-(6-deoxy-alpha-l-mannopyranos;ACTEOSIDE :B-D-GLUCOPYRANOSIDE, 2-(3,4-DIHYDROXYPHENYL)ETHYL 3-O-(6-DEOXY-A-L-MANNOPYRANOSYL)-,4-[3-(3,4-DIHYDROXYPHENYL)-2-PROPENOATE],(E)-,;Acetoside;Extract from Verbena minutiflora (B864379);[(2R,3R,4R,5R,6R)-6-[2-(3,4-Dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate;VERBASCOSIDE WITH HPLC;2-(3,4-Dihydroxyphenyl)ethyl 3-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranoside 4-[(E)-3-(3,4-dihydroxyphenyl)propenoate];3,4-Dihydroxyphenethyl alcohol acteoside
• CAS NO: 61276-17-3
• Molecular Formula: C₂₉H₃₆O₁₅
• Molecular Weight: 624.59
• Product Categories: Miscellaneous Natural Products;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 61276-17-3.mol
• Article Data: 8

Chemical Properties

• Melting Point: 232℃
• Boiling Point: 908.8 °C at 760 mmHg
• Flash Point: 294.7 °C
• Appearance: /
• Density: 1.6 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.689
• Storage Temp.: room temp
• Solubility: DMSO (Slightly), Ethyl Acetate (Very Slightly), Methanol (Slightly)
• PKA: 9.31±0.10(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: Verbascoside(CAS DataBase Reference)
• NIST Chemistry Reference: Verbascoside(61276-17-3)
• EPA Substance Registry System: Verbascoside(61276-17-3)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 2
• RTECS: LZ5786000
• Hazardous Substances Data: 61276-17-3(Hazardous Substances Data)

Usage

Description

Verbascoside is isolated from Lantana camara, acts as an ATP-competitive inhibitor of PKC, with an IC50 of 25 μM, and has antitumor, anti-inflammatory and antineuropathic pain activity.

Natural occurrences

Verbascoside can be found in species in all the families of the order Lamiales (syn. Scrophulariales). Only two examples are known from outside the order,in the clade Asterids.

Mechanism of action

It is known, that amyloid fibrils accumulation in cerebral can easily lead to neurodegenerative disorders. Acteoside has been reported to inhibit Aβ42 aggregation by activating nuclear translocation of the transcription factor NF-E2-related factor 2 (Nrf2), increasing heme oxygenase-1 (HO-1) expression. It has also been shown that acteoside could decrease nitric oxide synthase (NOS) activity and caspase-3 expression.

Chemical Properties

White solid

Uses

Verbascoside is an agent producing effects on anti-GBM nephritis in rats. Effective agent against glomerulonephritis. Phenolic anti-oxidant agent.

Enzyme inhibitor

This plant glycoside and antioxidant (FW = 624.60 g/mol; CAS 61276-173), also known as verbascoside, inhibits TNFa-mediated apoptosis in LPSstimulated macrophages as well as 1-methyl-4-phenylpyridiniuminduced apoptosis in cerebellar granule neurons. It also inhibits proliferation of human promyelocytic HL-60 leukemia cells by inducing cell cycle arrest at the G0/G1 phase, followed by differentiation into monocytes. Acteoside inhibits PMA-induced invasion and migration of human fibrosarcoma cells by Ca2+-dependent CaMK/ERK and JNK/NFκB-signaling pathways. Acteoside thus shows the potential as antimetastatic agent. Another intriguing finding is that acteoside inhibits amyloid-β aggregation. Target(s): aldose reductase; protein kinase C; integrase, HIV-1; peptidyl-dipeptidase A, or angiotensin-converting enzyme; tyrosinase, or monophenol monooxygenase; 5-lipoxygenase, or arachidonate 5-lipoxygenase.

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

Upstream product

• 250740-80-8 2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethyl 4-O-[(E,Z)-3,4-bis(O-tert-butyldimethylsilyl)caffeoyl]-6-O-(4,4'-dimethoxytrityl)-3-O-(α-L-rhamnopyranosyl)-β-D-glucopyranose 
• 253790-75-9 3,4-di(benzyloxy)phenethyl 2,6-di-O-acetyl-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-4-O-(3,4-di-O-benzylcaffeoyl)-β-D-glucopyranoside 
• 253790-73-7 3,4-di(benzyloxy)phenethyl 2,6-di-O-acetyl-3-O-allyl-4-O-(3,4-di-O-benzylcaffeoyl)-β-D-glucopyranoside 
• 253790-74-8 3,4-di(benzyloxy)phenethyl 2,6-di-O-acetyl-4-O-(3,4-di-O-benzylcaffeoyl)-β-D-glucopyranoside 
• 253790-71-5 3,4-di(benzyloxy)phenethyl 2,4-di-O-acetyl-3-O-allyl-6-O-trityl-β-D-glucopyranoside 
• 253790-70-4 3,4-di(benzyloxy)phenethyl 3-O-allyl-6-O-trityl-β-D-glucopyranoside 
• 253790-68-0 3,4-di(benzyloxy)phenethyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranoside 
• 253790-72-6 3,4-di(benzyloxy)phenethyl 2,6-di-O-acetyl-3-O-allyl-β-D-glucopyranoside 
• 253790-69-1 3,4-di(benzyloxy)phenethyl 3-O-allyl-β-D-glucopyranoside 
• 253790-67-9 2,4,6-tri-O-acetyl-3-O-allyl-α-D-glucopyranosyl chloride 
• 39698-00-5 acetyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranoside 
• 54429-62-8 (E)-3-(3,4-bis(benzyloxy)phenyl)acrylic acid 
• 96826-11-8 2-<3,4-bis(benzyloxy)phenyl>ethanol 
• 253790-76-0 3,4-di(benzyloxy)phenethyl 3-O-(α-L-rhamnopyranosyl)-4-O-(3,4-di-O-benzylcaffeoyl)-β-D-glucopyranoside 

Downstream Products

• 90985-64-1 deacylverbascoside dimethyl ether 
• 64142-09-2 acteoside tetramethyl ether 
• 3615-41-6 L-Rhamnose 
• 50-99-7 D-glucose 
• 97747-56-3 cis-verbascoside 
• 2280-44-6 D-Glucose 
• 73-34-7 L-rhamnose 
• 61548-34-3 decaffeoyl verbascoside 
• 10597-60-1 hydroxytyrosol 
• 3843-74-1 Methyl caffeate 

Relevant articles and documents

An Approach to the Synthesis of Electron-Rich and Hindered Esters and Its Application to the Synthesis of Acteoside

Electron-rich esters are ubiquitously distributed in natural products and play a central role in bioactivities. Herein, we disclose an efficient, mild, and general esterification approach to the synthesis of these esters by employing gold(I)-catalyzed acylation reaction with alkyne-tethered mixed anhydrides and alcohols. This method can be applied to ester-bond formation in complex substrates and facilitates efficient synthesis of acteoside, which belongs to the family of phenylethanoid glycosides and possesses a broad range of bioactivities.

Synthesis of verbascoside: A dihydroxyphenylethyl glycoside with diverse bioactivity

TMSOTf-mediated condensation of ethyl 4,6-O-benzylidene-1-thio-β-D- glucopyranoside (2) with peracetylated α-L-rhamnopyranosyl trichloroacetimidate donor 3a resulted in the formation of orthoester 4, which, after acetylation, rearranged into ethyl 3-O-(α-L-rhamnopyranosyl)-l- thio-β-D-glucopyranoside derivative 6a. The latter compound was converted into the corresponding trichloroacetimidate donors 8a-b. An alternative approach to trichloroacetimidate 8c commenced with the iodonium ion mediated glycosidation of ethyl 2,3,4-tri-O-benzoyl-1-thio-α-L-rhamnopyranside (15) with 1,2:5,6-diisopropylidene-D-glucofuranose (16) to afford disaccharide 17, which was transformed into 8c in five steps. Condensation of 8a-c with 2- [3,4-di-(tert-butyldimethylsilyloxy)phenyl]ethanol (12) gave, after deacylation, key intermediate 14. Protecting-group manipulation of 14 and subsequent esterification of resulting 22 with 3,4-di-O-tert- butyldimethylsilylcaffeic acid (27) gave, after deprotection, verbascoside (1).

NINE PHENETHYL ALCOHOL GLYCOSIDES FROM STACHYS SIEBOLDII

Three new phenethyl alcohol glycosides together with six known compounds have been isolated from the leaves of Stachys sieboldii.On the basis of chemical and spectral analyses, the structures of three new compounds named stachysosides A, B and C have been established as 2-(3,4-dihydroxyphenyl)ethyl O-α-L-arabinopyranosyl-(1->2)-α-L-rhamnopyranosyl-(1->3)-4-O-E-caffeoyl-β-D-glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl O-α-L-arabinopyranosyl-(1->2)-α-L-rhamnopyranosyl-(1->3)-4-O-E-feruloyl-β-D-glucopyranoside and 2-(3-hydroxy-4-methoxyphenyl)ethyl O-α-L-arabinopranosyl-(1->2)-α-L-rhamnopyranosyl-(1->3)-4-O-E-feruloyl-β-D-glucopyranoside, respectively.