| Synonyms |
Verbascoside; Kusaginin; β-D-Glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl 3-O-(6-deoxy-α-L-mannopyranosyl)-, 4-[3-(3,4-dihydroxyphenyl)-2-propenoate],
(E)-; (3,4-Dihydroxyphenyl)ethyl O-α-rhamnopyranosyl(1→3)-4-O-caffeoyl-β-D glucopyranoside; Acteroside; Distinctive Active Powder SL Special; Distinctive Phytostem Lilac; NSC 603831; O'''-Desarabinosyllavandulifolioside A; Russetinol; Stereospermin; TJC 160; trans-Acteoside; trans-Verbascoside |
| IUPAC Name |
[(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 |
| Molecular Weight |
624.59 |
| Molecular Formula |
C29H36O15 |
| Canonical SMILES |
CC1C(C(C(C(O1)OC2C(C(OC(C2OC(=O)C=CC3=CC(=C(C=C3)O)O)CO)OCCC4=CC(=C(C=C4)O)O)O)O)O)O |
| InChI |
InChI=1S/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 |
| InChIKey |
FBSKJMQYURKNSU-ZLSOWSIRSA-N |
| Boiling Point |
908.8±65.0 °C at 760 mmHg |
| Flash Point |
294.7°C |
| Purity |
>98% |
| Density |
1.6 g/cm3 |
| Solubility |
Soluble in DMSO (10 mM) |
| Appearance |
Powder |
| Application |
antineoplastic; antimetastatic;antimicrobial activity |
| Storage |
-20 °C |
| Complexity |
936 |
| Exact Mass |
624.20542044 |
| Index Of Refraction |
1.689 |
| In Vitro |
Verbascoside acts as an ATP-competitive inhibitor of PKC, with an IC50 of 25 µM. Verbascoside shows Kis of 22 and 28 µM with respect to ATP and histone, respectively. Verbascoside has potent antitumor activity against L-1210 cells, with an IC50 of 13 µM. Verbascoside (5, 10 µM) suppresses 2,4-dinitrochlorobenzene (DNCB)-induced T cell costimulatory factors CD86 and CD54, proinflammatory cytokines, and NFκB pathway activation in THP-1 cells. |
| In Vivo |
Verbascoside (1%) reduces the overall scratching behavior incidence as well as the severity of the skin lesions in 2,4-dinitrochlorobenzene (DNCB)-induced atopic dermatitis (AD) mice model. Verbascoside also blocks DNCB-induced expression of proinflammatory cytokine TNF-α, IL-6, and IL-4 mRNA in skin lesions. Verbascoside (50, 100 mg/kg, i.p.) does not modify chronic constriction injury (CCI)-induced cold allodynia. Verbascoside (200 mg/kg, i.p.) decreases hyper-sensitivity to cold stimulus, acetone, on day 3 in rats. Verbascoside also significantly reduces behavioral changes associated with neuropathy. Moreover, Verbascoside decreases Bax and increases Bcl-2 on day 3. |
| PSA |
245.29000 |
| Target |
PKC; Apoptosis; Bacterial; HSV |
| Vapor Pressure |
0.0±0.3 mmHg at 25°C |
| XLogP3-AA |
-0.5 |
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