Verbascoside
Chemical compound
From Wikipedia, the free encyclopedia
Verbascoside is a polyphenol glycoside[1] in which the phenylpropanoid caffeic acid and the phenylethanoid hydroxytyrosol form an ester and an ether bond respectively, to the rhamnose part of a disaccharide, namely β-(3′,4′-dihydroxyphenyl)ethyl-O-α-L-rhamnopyranosyl(1→3)-β-D-(4-O-caffeoyl)-glucopyranoside.[2]
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| Names | |
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| IUPAC name
2-(3,4-Dihydroxyphenyl)ethyl α-L-rhamnopyranosyl-(1→4)-{5-O-[(2E)-3-(3,4-dihydroxymethyl)prop-2-enoyl]-β-D-glucopyranoside} | |
| Systematic 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]oxy}oxan-3-yl (2E)-3-(3,4-dihydroxymethyl)prop-2-enoate | |
| Other names
Acteoside Kusaginin Orobanchin | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.112.547 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C29H36O15 | |
| Molar mass | 624.592 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Occurrences
Natural occurrences
Verbascoside can be found in species in all the families of the order Lamiales (syn. Scrophulariales).[3] Only two examples are known from outside the order,[4] in the clade Asterids.
- in the Lamiales
In the family Lamiaceae, it can be found in the medicinal plants in the genus Phlomis,[5] in the Scrophulariaceae, in Verbascum phlomoides,[6] Verbascum mallophorum,[7] or, in the family Buddlejaceae, in Buddleja globosa[8] or Buddleja cordata,[9] in the family Bignoniaceae, in Pithecoctenium sp and Tynanthus panurensis, in the family Orobanchaceae, in Cistanche sp and Orobanche rapum-genistae,[2] 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,[4] and, in the Byblidaceae, in Byblis liniflora.[3]
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,[8] notably against Staphylococcus aureus.[9] It can also have anti-inflammatory properties.[7]
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]