Verbascoside

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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
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.112.547 Edit this at Wikidata
UNII
  • 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
  • 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
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 checkY☒N ?)

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]

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

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

apiosides in Verbascum sp.[15]

In in vitro cultures

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

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

References

  1. PMID 15907957
    .
  2. ^
    doi:10.1016/S0031-9422(00)82429-2
    .
  3. ^
    doi:10.5586/asbp.2004.002
    .
  4. ^
    doi:10.1016/j.bse.2009.05.003
    .
  5. PMID 24650578
    .
  6. S2CID 37043342
    .
  7. ^
    PMID 19828096
    .
  8. ^
    PMID 8258981
    .
  9. ^
    PMID 10432210
    .
  10. S2CID 260249396
    .
  11. S2CID 24506417
    .
  12. ^
    PMID 1812212
    .
  13. PMID 22268549
    .
  14. doi:10.1080/10575639808048278
    .
  15. PMID 8960288
    .
  16. S2CID 32914451
    .
  17. doi:10.1016/S0176-1617(98)80105-3
    .
  18. PMID 18395372
    .
  19. PMID 22197714
    .
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