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Verbascoside, a phenolic antioxidant agent, is a white solid compound isolated from Lantana camara. It acts as an ATP-competitive inhibitor of protein kinase C (PKC) with an IC50 of 25 μM and exhibits antitumor, anti-inflammatory, and antineuropathic pain activities.

61276-17-3

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61276-17-3 Usage

Uses

Used in Pharmaceutical Industry:
Verbascoside is used as an anti-inflammatory agent for its ability to reduce inflammation and alleviate pain. It is particularly effective in treating glomerulonephritis, a type of kidney inflammation.
Used in Antitumor Applications:
Verbascoside is used as an antitumor agent due to its potential to inhibit tumor growth and progression. It may be employed in the development of novel cancer treatments and therapies.
Used in Antineuropathic Pain Management:
Verbascoside is used as an antineuropathic pain agent for its ability to alleviate pain associated with nerve damage or dysfunction.
Used in Oxidative Stress Reduction:
As a phenolic antioxidant agent, Verbascoside is used to protect cells from oxidative stress and damage, which can contribute to various diseases and conditions.

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.

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.

Check Digit Verification of cas no

The CAS Registry Mumber 61276-17-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,1,2,7 and 6 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 61276-17:
(7*6)+(6*1)+(5*2)+(4*7)+(3*6)+(2*1)+(1*7)=113
113 % 10 = 3
So 61276-17-3 is a valid CAS Registry Number.
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

61276-17-3 Well-known Company Product Price

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  • Sigma-Aldrich

  • (00820580)  Verbascoside  primary pharmaceutical reference standard

  • 61276-17-3

  • 00820580-10MG

  • 4,743.18CNY

  • Detail

61276-17-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name Verbascoside

1.2 Other means of identification

Product number -
Other names -

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

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More Details:61276-17-3 SDS

61276-17-3Relevant articles and documents

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

Zhang, Xiaojuan,Yang, Yutong,Wang, Fuye,Zhou, Zhengbing,Zhang, Hongbin,Zhu, Yugen

supporting information, p. 9210 - 9215 (2021/11/30)

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.

Samioside, a new phenylethanoid glycoside with free-radical scavenging and antimicrobial activities from Phlomis samia

Kyriakopoulou,Magiatis,Skaltsounis,Aligiannis,Harvala

, p. 1095 - 1097 (2007/10/03)

A new phenylethanoid glycoside, samioside, was isolated from the aerial parts of Phlomis samia and identified as 1-O-3,4-(dihydroxyphenyl)ethyl β-D-apiofuranosyl-(1→4)-α-L-rhamnopyranosyl-(1→3)-4-O- caffeoyl-β-D-glucopyranoside (1). In addition, one known phenylethanoid glycoside and three known flavonoids were identified as acteoside (2), apigenin, chrysoeriol, and ermanin, respectively. The structure of 1 was elucidated on the basis of its spectroscopic data. Samioside (1) demonstrated scavenging properties toward the DPPH radical and antimicrobial activity against Gram-positive and -negative bacteria.

Synthesis of verbascoside: A dihydroxyphenylethyl glycoside with diverse bioactivity

Duynstee, Howard I.,De Koning, Martijn C.,Ovaa, Huib,Van Der Marel, Gijs A.,Van Boom, Jacques H.

, p. 2623 - 2632 (2007/10/03)

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

Nishimura, Hiroaki,Sasaki, Hiroshi,Inagaki, Nobuyuki,Chin, Masao,Zhengxiong, Chen,Mitsuhashi, Hiroshi

, p. 965 - 969 (2007/10/02)

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.

PHENYLPROPANOID GLYCOSIDES OF Teucrium polium

Oganesyan, G. B.,Galstyan, A. M.,Mnatsakanyan, V. A.,Shashkov, A. S.,Agababyan, P. V.

, p. 556 - 559 (2007/10/02)

Together with poliumoside we have isolated for the first time from golden germander verbascoside and a new phenylpropanoid glycoside (teupolioside) for which the structure of 2-(3,4-dihydroxyphenyl)ethyl O-β-D-galactopyranosyl-(1->2)-O-α-L-rhamnopyranosyl-(1->3)-4-O-caffeoyl-β-D-glucopyranoside is proposed.A mixture of poliumoside and teupolioside revealed a moderate antibacterial activity.

Constitutions of forsythosides F and G, new phenol glycosides of Forsythia viridissima stems

Endo, Katsuya,Takahashi, Kazuhiro

, p. 291 - 294 (2007/10/02)

Two new phenol glycosides forsythoside F (1) and forsythoside G (2) have been isolated from Forsythia viridissima stems and their structures were established based on the spectroscopic data and chemical transformations.D-2-O-methylapiose was for the first time characterized in the natural product.

PHENOLIC GLYCOSIDES FROM DISEASED ROOTS OF REHMANNIA GLUTINOSA VAR. PURPUREA

Shoyama, Yukihiro,Matsumoto, Masami,Nishioka, Itsuo

, p. 983 - 986 (2007/10/02)

A new caffeoyl glycoside was isolated from the methanolic extract of the diseased root of Rehmannia glutinosa together with acteoside.The structure of the new phenol glycoside was elucidated as 3,4-dihydroxy-β-phenethyl-O-α-L-rhamnopyranosyl-(1 -> 3)-O-β-D-galactopyranosyl-(1 -> 6)-4-O-caffeoyl-β-D-glucopyranoside by spectral and chemical evidence.These compounds were detected as stress compounds in the roots of Rehmannia glutinosa following microbial infection.They inhibited the growth of the two Pseudomonas species. - Key Word Index: Rehmannia glutinosa; Scrophulariaceae; caffeoyl glycoside of 3,4-dihydroxyphenethyl alcohol; stress compound; antimicrobial activity.

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