Chemistry: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
UNII
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).
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Infobox references

Verbascoside is a caffeoyl phenylethanoid 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 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

References

  1. ↑ Taskova, Rilka Mladenova; Gotfredsen, Charlotte Held; Jensen, Søren Rosendal (2005). "Chemotaxonomic markers in Digitalideae (Plantaginaceae)". Phytochemistry 66 (12): 1440–7. doi:10.1016/j.phytochem.2005.04.020. PMID 15907957. Bibcode: 2005PChem..66.1440T. 
  2. ↑ 2.0 2.1 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): 1123–7. doi:10.1016/S0031-9422(00)82429-2. Bibcode: 1982PChem..21.1123A. 
  3. ↑ 3.0 3.1 Schlauer, Jan; Budzianowski, Jaromir; Kukułczanka, Krystyna; Ratajczak, Lidia (2011). "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. doi:10.5586/asbp.2004.002. 
  4. ↑ 4.0 4.1 Grevenstuk, Tomás; Van Der Hooft, Justin J.J; Vervoort, Jacques; De Waard, Pieter; Romano, Anabela (2009). "Iridoid and caffeoyl phenylethanoid glycosides of the endangered carnivorous plant Pinguicula lusitanica L. (Lentibulariaceae)". Biochemical Systematics and Ecology 37 (4): 285–9. doi:10.1016/j.bse.2009.05.003. 
  5. ↑ Sarkhail, Parisa; Nikan, Marjan; Sarkheil, Pantea; Gohari, Ahmad R; Ajani, Yousef; Hosseini, Rohollah; Hadjiakhoondi, Abbass; Saeidnia, Soodabeh (2014). "Quantification of verbascoside in medicinal species of Phlomis and their genetic relationships". DARU Journal of Pharmaceutical Sciences 22 (1): 32. doi:10.1186/2008-2231-22-32. PMID 24650578. 
  6. ↑ Gvazava, L. N; Kikoladze, V. S (2007). "Verbascoside from Verbascum phlomoides". Chemistry of Natural Compounds 43 (6): 710–1. doi:10.1007/s10600-007-0240-9. 
  7. ↑ 7.0 7.1 Speranza, L.; Franceschelli, S.; Pesce, M.; Menghini, L.; Patruno, A.; Vinciguerra, I.; De Lutiis, M. A.; 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. 
  8. ↑ 8.0 8.1 Pardo, F; Perich, F; Villarroel, L; Torres, R (1993). "Isolation of verbascoside, an antimicrobial constituent of Buddleja globosa leaves". Journal of Ethnopharmacology 39 (3): 221–2. doi:10.1016/0378-8741(93)90041-3. PMID 8258981. 
  9. ↑ 9.0 9.1 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. 
  10. ↑ Murai, Michiko; Tamayama, Yasuhiko; Nishibe, Sansei (2007). "Phenylethanoids in the Herb of Plantago lanceolataand Inhibitory Effect on Arachidonic Acid-Induced Mouse Ear Edema1". Planta Medica 61 (5): 479–80. doi:10.1055/s-2006-958143. PMID 7480214. 
  11. ↑ Deepak, Mundkinajeddu; Handa, Sukhdev Swami (2000). "Antiinflammatory activity and chemical composition of extracts of Verbena officinalis". Phytotherapy Research 14 (6): 463–5. doi:10.1002/1099-1573(200009)14:6<463::AID-PTR611>3.0.CO;2-G. PMID 10960904. 
  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, Angela; Pati, Sandra; Minervini, Fiorenza; d'Antuono, Isabella; Linsalata, Vito; Lattanzio, Vincenzo (2012). "Verbascoside, Isoverbascoside, and Their Derivatives Recovered from Olive Mill Wastewater as Possible Food Antioxidants". Journal of Agricultural and Food Chemistry 60 (7): 1822–9. doi:10.1021/jf204001p. PMID 22268549. 
  14. ↑ Magiatis, P; Mitaku, S; Tsitsa, E; Skaltsounis, A. L; Harvala, C (1998). "Verbascoside Derivatives and Iridoid Glycosides from Verbascum Undulatum". Natural Product Letters 12 (2): 111–5. 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): 484–487. doi:10.1007/BF00232101. PMID 24213785. 
  17. ↑ Wysokiińska, H; Rózga, M (1998). "Establishment of transformed root cultures of Paulownia tomentosa for verbascoside production". Journal of Plant Physiology 152 (1): 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 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. 
  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. 



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