Verbascoside Explained

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.

Occurrences

Natural occurrences

Verbascoside can be found in species in all the families of the order Lamiales (syn. Scrophulariales).[2] Only two examples are known from outside the order,[3] in the clade Asterids.

in the LamialesIn 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 family Buddlejaceae, in Buddleja globosa[7] or Buddleja cordata,[8] in the family Bignoniaceae, in Pithecoctenium sp and Tynanthus panurensis, in the family Orobanchaceae, 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]

See also

Notes and References

  1. 10.1016/j.phytochem.2005.04.020 . 15907957 . Chemotaxonomic markers in Digitalideae (Plantaginaceae) . Phytochemistry . 66 . 12 . 1440–7 . 2005 . Taskova . Rilka Mladenova . Gotfredsen . Charlotte Held . Jensen . Søren Rosendal. 2005PChem..66.1440T .
  2. 10.5586/asbp.2004.002 . Acteoside and related phenylethanoid glycosides in Byblis liniflora Salisb. Plants propagated in vitro and its systematic significance . Acta Societatis Botanicorum Poloniae . 73 . 1 . 9–15 . 2011 . Schlauer . Jan . Budzianowski . Jaromir . Kukułczanka . Krystyna . Ratajczak . Lidia . free.
  3. 10.1016/j.bse.2009.05.003 . Iridoid and caffeoyl phenylethanoid glycosides of the endangered carnivorous plant Pinguicula lusitanica L. (Lentibulariaceae) . Biochemical Systematics and Ecology . 37 . 4 . 285–9 . 2009 . Grevenstuk . Tomás . Van Der Hooft . Justin J.J . Vervoort . Jacques . De Waard . Pieter . Romano . Anabela. 2009BioSE..37..285G .
  4. 10.1186/2008-2231-22-32 . 24650578 . 3998186 . Quantification of verbascoside in medicinal species of Phlomis and their genetic relationships . DARU Journal of Pharmaceutical Sciences . 22 . 1 . 32 . 2014 . Sarkhail . Parisa . Nikan . Marjan . Sarkheil . Pantea . Gohari . Ahmad R . Ajani . Yousef . Hosseini . Rohollah . Hadjiakhoondi . Abbass . Saeidnia . Soodabeh . free .
  5. 10.1007/s10600-007-0240-9 . Verbascoside from Verbascum phlomoides . Chemistry of Natural Compounds . 43 . 6 . 710–1 . 2007 . Gvazava . L. N . Kikoladze . V. S. 37043342 .
  6. 19828096 . 2009 . Anti-inflammatory properties of the plant Verbascum mallophorum . Journal of Biological Regulators and Homeostatic Agents . 23 . 3 . 189–95. Speranza . L. . Franceschelli . S. . Pesce . M. . Menghini . L. . Patruno . A. . Vinciguerra . I. . De Lutiis . M. A. . Felaco . M. . Felaco . P. . Grilli . A..
  7. 10.1016/0378-8741(93)90041-3 . 8258981 . Isolation of verbascoside, an antimicrobial constituent of Buddleja globosa leaves . Journal of Ethnopharmacology . 39 . 3 . 221–2 . 1993 . Pardo . F . Perich . F . Villarroel . L . Torres . R.
  8. 10.1016/S0378-8741(98)00203-7 . 10432210 . Mode of action of Buddleja cordata verbascoside against Staphylococcus aureus . Journal of Ethnopharmacology . 66 . 1 . 75–8 . 1999 . Guillermo Avila . José . De Liverant . Juliana G . Martı́Nez . Andrés . Martı́Nez . Gabriel . Muñoz . José Luis . Arciniegas . Amira . Romo De Vivar . Alfonso.
  9. 10.1016/S0031-9422(00)82429-2 . Structures of verbascoside and orobanchoside, caffeic acid sugar esters from Orobanche rapum-genistae . Phytochemistry . 21 . 5 . 1123–7 . 1982 . Andary . C . Wylde . R . Laffite . C . Privat . G . Winternitz . F. 1982PChem..21.1123A .
  10. 10.1055/s-2006-958143 . 7480214 . Phenylethanoids in the Herb of Plantago lanceolataand Inhibitory Effect on Arachidonic Acid-Induced Mouse Ear Edema1 . Planta Medica . 61 . 5 . 479–80 . 2007 . Murai . Michiko . Tamayama . Yasuhiko . Nishibe . Sansei. 260249396 .
  11. 10.1002/1099-1573(200009)14:6<463::AID-PTR611>3.0.CO;2-G . 10960904 . Antiinflammatory activity and chemical composition of extracts of Verbena officinalis . Phytotherapy Research . 14 . 6 . 463–5 . 2000 . Deepak . Mundkinajeddu . Handa . Sukhdev Swami. 24506417 .
  12. 10.1021/np50078a016 . 1812212 . Verbascoside Isolated from Lantana camara, an Inhibitor of Protein Kinase C . Journal of Natural Products . 54 . 6 . 1595–600 . 1991 . Herbert . J. M . Maffrand . J. P . Taoubi . K . Augereau . J. M . Fouraste . I . Gleye . J.
  13. 10.1021/jf204001p . 22268549 . Verbascoside, Isoverbascoside, and Their Derivatives Recovered from Olive Mill Wastewater as Possible Food Antioxidants . Journal of Agricultural and Food Chemistry . 60 . 7 . 1822–9 . 2012 . Cardinali . Angela . Pati . Sandra . Minervini . Fiorenza . d'Antuono . Isabella . Linsalata . Vito . Lattanzio . Vincenzo.
  14. 10.1080/10575639808048278 . Verbascoside Derivatives and Iridoid Glycosides from Verbascum Undulatum . Natural Product Letters . 12 . 2 . 111–5 . 1998 . Magiatis . P . Mitaku . S . Tsitsa . E . Skaltsounis . A. L . Harvala . C.
  15. 8960288 . 1996 . Klimek . B . 6'-0-apiosyl-verbascoside in the flowers of mullein (Verbascum species) . Acta Poloniae Pharmaceutica . 53 . 2 . 137–40.
  16. 10.1007/BF00232101 . Verbascoside production by plant cell cultures . Plant Cell Reports . 9 . 9 . 1991 . Inagaki . Nobuyuki . Nishimura . Hiroaki . Okada . Minoru . Mitsuhashi . Hiroshi . 484–487 . 24213785 . 32914451 .
  17. 10.1016/S0176-1617(98)80105-3 . Establishment of transformed root cultures of Paulownia tomentosa for verbascoside production . Journal of Plant Physiology . 152 . 1 . 78–83 . 1998 . Wysokiińska . H . Rózga . M.
  18. 10.1016/j.toxlet.2008.02.006 . 18395372 . Verminoside- and verbascoside-induced genotoxicity on human lymphocytes: Involvement of PARP-1 and p53 proteins . Toxicology Letters . 178 . 2 . 71–6 . 2008 . Santoro . Antonietta . Bianco . Giuseppe . Picerno . Patrizia . Aquino . Rita Patrizia . Autore . Giuseppina . Marzocco . Stefania . Gazzerro . Patrizia . Lioi . Maria Brigida . Bifulco . Maurizio.
  19. 10.1016/j.fct.2011.12.006 . 22197714 . Verbascoside is not genotoxic in the ST and HB crosses of the Drosophila wing spot test, and its constituent, caffeic acid, decreases the spontaneous mutation rate in the ST cross . Food and Chemical Toxicology . 50 . 3–4 . 1082–90 . 2012 . Santos-Cruz . Luis Felipe . Ávila-Acevedo . José Guillermo . Ortega-Capitaine . Diego . Ojeda-Duplancher . Jesús Clemente . Perdigón-Moya . Juana Laura . Hernández-Portilla . Luis Barbo . López-Dionicio . Héctor . Durán-Díaz . Ángel . Dueñas-García . Irma Elena . Castañeda-Partida . Laura . García-Bores . Ana María . Heres-Pulido . María Eugenia.

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