Verbascoside

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]

Verbascoside

Chemical structure of verbascoside
Names
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
CAS Number	61276-17-3 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:132853 N
ChEMBL	ChEMBL231853 N
ChemSpider	4445112 N
ECHA InfoCard	100.112.547
PubChem CID	5281800
UNII	3TGX09BD5B Y
CompTox Dashboard (EPA)	DTXSID701021953
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 N Key: FBSKJMQYURKNSU-ZLSOWSIRSA-N N 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 Key: FBSKJMQYURKNSU-ZLSOWSIRBQ
SMILES C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H](O[C@@H]([C@H]2OC(=O)/C=C/C3=CC(=C(C=C3)O)O)CO)OCCC4=CC(=C(C=C4)O)O)O)O)O)O
Properties
Chemical formula	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). N verify (what is YN ?) Infobox references

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]

See also

• Echinacoside