61276-17-3 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.
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
61276-17-3Relevant 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.
Total Synthesis of the Phenylpropanoid Glycoside, Acteoside
Kawada, Toshinari,Asano, Ryuji,Hayashida, Shiho,Sakuno, Tomoyasu
, p. 9268 - 9271 (2007/10/03)
-
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.