Verbascoside

Verbascoside
Chemical structure of verbascoside
Names
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
Other names
Acteoside
Kusaginin
Orobanchin
Identifiers
61276-17-3 Yes
ChEMBL ChEMBL231853 
Jmol-3D images Image
PubChem 5281800
Properties
Molecular formula
 C29H36O15
Molar mass 624.59 g·mol−1
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
  verify (what is: Yes/?)
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.

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

  1. ↑ Chemotaxonomic markers in Digitalideae (Plantaginaceae). R.M. Taskova, C.H. Gotfredsen and S.R. Jensen, Phytochemistry, 2005, volume 66, pages 1440–1447, doi:10.1016/j.phytochem.2005.04.020
  2. ↑ 2.0 2.1 Acteoside and related phenylethanoid glycosides in Byblis liniflora Salisb. plants propagated in vitro and its systematic significance. Jan Schlauer, Jaromir Budzianowski, Krystyna Kukułczanka and Lidia Ratajczak, Acta Societatis Botanicorum Poloniae, 2004, volume 73, issue 1, doi:10.5586/asbp.2004.002
  3. ↑ 3.0 3.1 Iridoid and caffeoyl phenylethanoid glycosides of the endangered carnivorous plant Pinguicula lusitanica L. (Lentibulariaceae). Tomás Grevenstuk, Justin J.J. van der Hooft, Jacques Vervoort, c, Pieter de Waard and Anabela Romano, Biochemical Systematics and Ecology, October 2009, Volume 37, Issue 4, Pages 285–289, doi:10.1016/j.bse.2009.05.003
  4. ↑ Sarkhail, P; Nikan, M; Sarkheil, P; Gohari, AR; Ajani, Y; Hosseini, R; Hadjiakhoondi, A; Saeidnia, S (2014). "Quantification of verbascoside in medicinal species of Phlomis and their genetic relationships" 22 (1). p. 32. doi:10.1186/2008-2231-22-32.
  5. ↑ Gvazava, L. N.; Kikoladze, V. S. (2007). "Verbascoside from Verbascum phlomoides". Chemistry of Natural Compounds 43 (6): 710. doi:10.1007/s10600-007-0240-9.
  6. ↑ 6.0 6.1 Speranza, L; Franceschelli, S; Pesce, M; Menghini, L; Patruno, A; Vinciguerra, I; De Lutiis, MA; Felaco, M et al. (2009). "Anti-inflammatory properties of the plant Verbascum mallophorum". Journal of biological regulators and homeostatic agents 23 (3): 189–95. PMID 19828096.
  7. ↑ 7.0 7.1 Pardo F, Perich F, Villarroel L, Torres R (August 1993). "Isolation of verbascoside, an antimicrobial constituent of Buddleja globosa leaves". J Ethnopharmacol 39 (3): 221–2. doi:10.1016/0378-8741(93)90041-3. PMID 8258981.
  8. ↑ 8.0 8.1 Guillermo Avila, José; De Liverant, Juliana G.; Martı́Nez, Andrés; Martı́Nez, Gabriel; Muñoz, José Luis; Arciniegas, Amira; Romo De Vivar, Alfonso (1999). "Mode of action of Buddleja cordata verbascoside against Staphylococcus aureus". Journal of Ethnopharmacology 66 (1): 75–8. doi:10.1016/S0378-8741(98)00203-7. PMID 10432210.
  9. ↑ Andary, C.; Wylde, R.; Laffite, C.; Privat, G.; Winternitz, F. (1982). "Structures of verbascoside and orobanchoside, caffeic acid sugar esters from Orobanche rapum-genistae". Phytochemistry 21 (5): 1123. doi:10.1016/S0031-9422(00)82429-2.
  10. ↑ Phenylethanoids in the Herb of Plantago lanceolata and Inhibitory Effect on Arachidonic Acid-Induced Mouse Ear Edema. Michiko Murai (nee Sasahara), Yasuhiko Tamayama and Sansei Nishibe, Planta Med., 1995;, volume 61, issue 5, pages 479-480, doi:10.1055/s-2006-958143
  11. ↑ Antiinflammatory activity and chemical composition of extracts of Verbena officinalis. Mundkinajeddu Deepak and Sukhdev Swami Handa, Phytotherapy Research, September 2000, Volume 14, Issue 6, pages 463–465, doi:10.1002/1099-1573(200009)14:6<463::AID-PTR611>3.0.CO;2-G
  12. ↑ 12.0 12.1 Herbert, J. M.; Maffrand, J. P.; Taoubi, K.; Augereau, J. M.; Fouraste, I.; Gleye, J. (1991). "Verbascoside Isolated from Lantana camara, an Inhibitor of Protein Kinase C". Journal of Natural Products 54 (6): 1595–600. doi:10.1021/np50078a016. PMID 1812212.
  13. ↑ Cardinali, A; Pati, S; Minervini, F; D'Antuono, I; Linsalata, V; Lattanzio, V (2012). "Verbascoside, isoverbascoside, and their derivatives recovered from olive mill wastewater as possible food antioxidants". J Agric Food Chem. 60 (7): 1822–1829. doi:10.1021/jf204001p. PMID 22268549.
  14. ↑ Magiatis, P.; Mitaku, S.; Tsitsa, E.; Skaltsounis, A. L.; Harvala, C. (1998). "Verbascoside Derivatives and Iridoid Glycosides fromVerbascum Undulatum". Natural Product Letters 12 (2): 111. doi:10.1080/10575639808048278.
  15. ↑ Klimek, B (1996). "6'-0-apiosyl-verbascoside in the flowers of mullein (Verbascum species)". Acta poloniae pharmaceutica 53 (2): 137–40. PMID 8960288.
  16. ↑ Inagaki, Nobuyuki; Nishimura, Hiroaki; Okada, Minoru; Mitsuhashi, Hiroshi (1991). "Verbascoside production by plant cell cultures". Plant Cell Reports 9 (9). doi:10.1007/BF00232101.
  17. ↑ Establishment of transformed root cultures of Paulownia tomentosa for verbascoside production. H. Wysokiińska and M. Rózga, Journal of Plant Physiology, 1998, Volume 152, Issue 1, Pages 78–83, doi:10.1016/S0176-1617(98)80105-3
  18. ↑ Santoro, Antonietta; Bianco, Giuseppe; Picerno, Patrizia; Aquino, Rita Patrizia; Autore, Giuseppina; Marzocco, Stefania; Gazzerro, Patrizia; Lioi, Maria Brigida; Bifulco, Maurizio (2008). "Verminoside- and verbascoside-induced genotoxicity on human lymphocytes: Involvement of PARP-1 and p53 proteins". Toxicology Letters 178 (2): 71–6. doi:10.1016/j.toxlet.2008.02.006. PMID 18395372.
  19. ↑ 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 et al. (2012). "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. doi:10.1016/j.fct.2011.12.006. PMID 22197714.