| Verbascoside Basic information |
| Description Natural occurrences Mechanism of action |
| 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)-,;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;Verbacoside |
| CAS: | 61276-17-3 |
| MF: | C29H36O15 |
| MW: | 624.59 |
| EINECS: | |
| Product Categories: | reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;chemical reagent;pharmaceutical intermediate;phytochemical;Miscellaneous Natural Products |
| Mol File: | 61276-17-3.mol |
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| Verbascoside Chemical Properties |
| Melting point | 232℃ |
| Boiling point | 908.8±65.0 °C(Predicted) |
| density | 1.60±0.1 g/cm3(Predicted) |
| storage temp. | Sealed in dry,Room Temperature |
| solubility | DMSO (Slightly), Ethyl Acetate (Very Slightly), Methanol (Slightly) |
| pka | 9.31±0.10(Predicted) |
| form | Solid |
| color | White to Pale Yellow |
| Stability: | Hygroscopic |
| InChIKey | FBSKJMQYURKNSU-ZLSOWSIRSA-N |
| LogP | 0.077 (est) |
| CAS DataBase Reference | 61276-17-3(CAS DataBase Reference) |
| Safety Information |
| Safety Statements | 24/25 |
| WGK Germany | 2 |
| RTECS | LZ5786000 |
| HS Code | 29389090 |
| Toxicity | LD50 oral in rat: > 5gm/kg |
| Verbascoside Usage And Synthesis |
| 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. |
| Definition | ChEBI: Acteoside is a glycoside that is the alpha-L-rhamnosyl-(1->3)-beta-D-glucoside of hydroxytyrosol in which the hydroxy group at position 4 of the glucopyranosyl moiety has undergone esterification by formal condensation with trans-caffeic acid. It has a role as a neuroprotective agent, an antileishmanial agent, an anti-inflammatory agent, a plant metabolite and an antibacterial agent. It is a cinnamate ester, a disaccharide derivative, a member of catechols, a polyphenol and a glycoside. It is functionally related to a hydroxytyrosol and a trans-caffeic acid. |
| 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. |
| Verbascoside Preparation Products And Raw materials |
