Verbascoside

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Verbascoside
Chemical structure of verbascoside
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

Identifiers
CAS number 61276-17-3 YesY=
PubChem 5281800
ChEMBL CHEMBL231853 N
Jmol-3D images Image 1
Properties
Molecular formula C29H36O15
Molar mass 624,59 g/mol
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Verbascoside is a phenylethanoid (with hydroxytyrosol) and a phenylpropanoid (with caffeic acid) sugar ester.

Natural occurrences

Verbascoside can be found in species in the Lamiales order (in the family Scrophulariaceae, Verbascum phlomoides,[1] Verbascum mallophorum,[2] or Buddlejaceae family Buddleja globosa[3] or Buddleja cordata,[4] in the Bignoniaceae family, Pithecoctenium sp and Tynanthus panurensis, in the Orobanchaceae family, Cistanche sp and Orobanche rapum-genistae[5] and in the Plantaginaceae Plantago lanceolata).[6] It has also been isolated from Verbena officinalis[7] and Lantana camara[8](Verbenaceae). It can also be produced in plant cell cultures of Leucosceptrum sp (Lamiaceae) and Syringa sp (Oleaceae).[9]

Verbascoside derivatives can be found in the Verbascum undulatum[10] and notably apiosides in Verbascum sp.[11]

Health effects

Verbascoside has an antimicrobial activity,[3] notably against Staphylococcus aureus.[4] It can also have anti-inflammatory properties.[2]

Although some "in vitro" genotoxicity of verbascoside has been reported on human lymphocytes with an involvement of PARP-1 and p53 proteins.,[12] subsequent "in vivo" tests reported no genotoxicity for high dosage oral administration.[13] It is a protein kinase C inhibitor.[8]


References

  1. ↑ 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. 
  2. ↑ 2.0 2.1 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. 
  3. ↑ 3.0 3.1 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. 
  4. ↑ 4.0 4.1 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. 
  5. ↑ 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. 
  6. ↑ 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
  7. ↑ 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
  8. ↑ 8.0 8.1 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. 
  9. ↑ Inagaki, Nobuyuki; Nishimura, Hiroaki; Okada, Minoru; Mitsuhashi, Hiroshi (1991). "Verbascoside production by plant cell cultures". Plant Cell Reports 9 (9). doi:10.1007/BF00232101. 
  10. ↑ 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. 
  11. ↑ Klimek, B (1996). "6'-0-apiosyl-verbascoside in the flowers of mullein (Verbascum species)". Acta poloniae pharmaceutica 53 (2): 137–40. PMID 8960288. 
  12. ↑ Santoro, Antonietta; Bianco, Giuseppe; Picerno, Patrizia; Aquino, Rita Patrizia; Autore, Giuseppina; Marzocco, Stefania; Gazzerro, Patrizia; Lioi, Maria Brigida et al. (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. 
  13. ↑ 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. 
Classes of phenylpropanoids
Examples
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