Verbascoside
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| Names | |
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| 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
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| Other names
Acteoside
Kusaginin Orobanchin |
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| Identifiers | |
61276-17-3  |
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| ChEMBL | ChEMBL231853  |
| ChemSpider | 4445112 |
| Jmol 3D model | Interactive image |
| PubChem | 5281800 |
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| Properties | |
| C29H36O15 | |
| Molar mass | 624.59 g·mol−1 |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 verify (what is ?) |
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| Infobox references | |
Verbascoside is a caffeoyl phenylethanoid glycoside (CPG).[1] It is an ester formed with the phenylethanoid hydroxytyrosol, the phenylpropanoid caffeic acid and the sugar alpha-L-rhamnopyranosyl-(1->3)-beta-D-glucopyranose.
Contents
Occurrences
Natural occurrences
Verbascoside can be found in species in all the families of the Lamiales order (syn. Scrophulariales).[2] Only two examples are known from outside the order,[3] in the clade Asterids.
- in the Lamiales
In the family Lamiaceae, it can be found in the medicinal plants in the genus Phlomis,[4] in the Scrophulariaceae, in Verbascum phlomoides,[5] Verbascum mallophorum,[6] or, in the Buddlejaceae family, in Buddleja globosa[7] or Buddleja cordata,[8] in the Bignoniaceae family, in Pithecoctenium sp and Tynanthus panurensis, in the Orobanchaceae family, in Cistanche sp and Orobanche rapum-genistae,[9] in the Plantaginaceae, in Plantago lanceolata,[10] in Verbenaceae, in Verbena officinalis (common vervain),[11] Aloysia citrodora (lemon verbena) and Lantana camara,[12] in the Oleaceae, in Olea europaea (olive),[13] in the Lentibulariaceae, in the carnivorous plant Pinguicula lusitanica,[3] and, in the Byblidaceae, in Byblis liniflora.[2]
Derivatives
Verbascoside derivatives can be found in the Verbascum undulatum[14] and notably apiosides in Verbascum sp.[15]
In in vitro cultures
It can also be produced in plant cell cultures of Leucosceptrum sp (Lamiaceae) and Syringa sp (Oleaceae).[16] It can also be produced in hairy roots cultures of Paulownia tomentosa (empress tree, Paulowniaceae).[17]
Biological activity
Verbascoside has an antimicrobial activity,[7] notably against Staphylococcus aureus.[8] It can also have anti-inflammatory properties.[6]
Although some in vitro genotoxicity of verbascoside has been reported on human lymphocytes with an involvement of PARP-1 and p53 proteins,[18] subsequent in vivo tests reported no genotoxicity for high dosage oral administration.[19] It is a protein kinase C inhibitor.[12]
References
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