Verbascoside - A review of its occurrence, (bio)synthesis and pharmacological significance

Biotechnology Advances

Volumn 32, Issue 6, 2014, Pages 1065-1076

  Alipieva, Kalina ^a   Korkina, Liudmila ^b   Orhan, Ilkay Erdogan ^c   Georgiev, Milen I ^d  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Bulgaria)

^b Molecular Pathology Laboratory Russian Research Medical University   (Russian Federation)

^c GAZI UNIVERSITY   (Turkey)

^d INSTITUTE OF MICROBIOLOGY   (Bulgaria)

Author keywords

(Bio)synthesis; Acteoside; Anti inflammatory; Cancer prevention; Cell suspension culture; Hairy roots; Phenylethanoid glycosides; Verbascum spp

Indexed keywords

CELL CULTURE;

ACTEOSIDE; ANTI-INFLAMMATORIES; CANCER PREVENTION; CELL SUSPENSION CULTURES; HAIRY ROOTS; PHENYLETHANOID GLYCOSIDES; VERBASCUM SPP;

SUGARS;

VERBASCUM;

ACTEOSIDE; ANTIINFLAMMATORY AGENT; GLUCOSIDE; PHENOL DERIVATIVE; PLANT EXTRACT;

ANIMAL; BIOAVAILABILITY; CELL LINE; CHEMISTRY; CLINICAL TRIAL (TOPIC); HUMAN; METABOLISM; MOUSE; PLANT ROOT;

ANIMALS; ANTI-INFLAMMATORY AGENTS; BIOLOGICAL AVAILABILITY; CELL LINE; CLINICAL TRIALS AS TOPIC; GLUCOSIDES; HUMANS; MICE; PHENOLS; PLANT EXTRACTS; PLANT ROOTS;

EID: 84926254927     PISSN: 07349750     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.biotechadv.2014.07.001     Document Type: Review

References (137)

1. Abdelouahab N., Heard C. Effect of the major glycosides of Harpagophytum procumbens (Devil's Claw) on epidermal cyclooxygenase-2 (COX-2) in vitro. J Nat Prod 2008, 71:746-749.
2. Akdemir Z., Kahraman C., Tatli I.I., Küpeli Akkol E., Süntar I., Keles H. Bioassay-guided isolation of anti-inflammatory, antinociceptive and wound healer glycosides from the flowers of Verbascum mucronatum Lam. J Ethnopharmacol 2011, 136:436-443.
3. Aldini G., Piccoli A., Beretta G., Morazzoni P., Riva A., Marinello C., et al. Antioxidant activity of polyphenols from solid olive residues of c.v. Coratina. Fitoterapia 2006, 77:121-128.
4. Alipieva K., Erdogan Orhan I., Tatli Cankaya I.I., Kostadinova E.P., Georgiev M.I. Treasure from garden: chemical profiling, pharmacology and biotechnology of mulleins. Phytochem Rev 2014, 13:417-444.
5. Andary C., Wydle R., Laffite C., Privat G., Winternitz F. Structures of verbascoside and orobanchoside caffeic acid sugar esters from Orobanche rapum-genistate. Phytochemistry 1982, 21:1123-1127.
6. Arruda A.L., Vieira C.J., Sousa D.G., Oliveira R.F., Castilho R.O. Jacaranda cuspidifolia Mart. (Bignoniaceae) as an antibacterial agent. J Med Food 2011, 14:1604-1608.
7. Avila J.G., de Liverant J.G., Martínez A., Martínez G., Muñoz J.L., Arciniegas A., et al. Mode of action of Buddleja cordata verbascoside against Staphylococcus aureus. J Ethnopharmacol 1999, 66:75-78.
8. Azimi H., Fallah-Tafti M., Khakshur A.A., Abdollahi M. A review of phytotherapy of acne vulgaris: perspective of new pharmacological treatments. Fitoterapia 2012, 83:1306-1317.
9. Backhouse N., Delporte C., Apablaza C., Farías M., Goïty L., Arrau S., et al. Antinociceptive activity of Buddleja globosa (matico) in several models of pain. J Ethnopharmacol 2008, 119:160-165.
10. Bilia A.R., Giomi M., Innocenti M., Gallori S., Vincieri F.F. HPLC-DAD-ESI-MS analysis of the constituents of aqueous preparation of verbena and lemon verbena and evaluation of the antioxidant activity. J Pharm Biomed Anal 2008, 46:463-470.
11. Birkofer L., Kaiser C., Thomas U. Acteosid und neoacteosid: Zukerester aus Syringa vulgaris. Z Naturforsch B 1968, 23:1051-1058.
12. Cardinali A., Pati S., Minervini F., Linsalata V., Lattanzio V. Verbascoside, isoverbascoside, and their derivates recovered from olive mill wastewater as possible food antioxidants. J Agric Food Chem 2012, 60:1822-1829.
13. Carrera-Quintanar L., Funes L., Viudes E., Tur J., Micol V., Roche E., et al. Antioxidant effect of lemon verbena extracts in lymphocytes of university students performing aerobic training program. Scand J Med Sci Sports 2012, 22:454-461.
14. Caturla N., Funes L., Perez-Fons L., Micol V. A randomized, double-blinded, placebo controlled study of the effect of a combination of lemon verbena extract and fish oil promega-3 fatty acid on joint management. J Altern Complement Med 2011, 17:1051-1063.
15. Chiou W.F., Lin L.C., Chen C.F. Acteoside protects endothelial cells against free radical-induced oxidative stress. J Pharm Pharmacol 2004, 56:743-748.
16. De Marco E., Savarese M., Paduano A., Sacchi R. Characterization and fractionation of phenolic compounds extracted from olive oil mill wastewaters. Food Chem 2007, 104:858-867.
17. De Souza P.A., Silva C.G., Machado B.R.P., Lucas N.C., Leitão G.G., Eleutherio E.C.A., et al. Evaluation of antimicrobial, antioxidant and phototoxic activities of extracts and isolated compounds from Stachytarpheta cayennesis (Rich.) Vahl. Rev Bras Farmacogn 2010, 20:922-928.
18. Deepak M., Umashankar D.C., Handa S.S. Verbascoside-a promising phenylpropanoid. Indian Drugs 1999, 36:336-345.
19. Del Rio D., Rodriguez-Mateos A., JPEm Spncer, Tognolini M., Borges G., Crozier A. Dietary (poly)phenolics in human health: structures, bioavailability, and evidence of protection against chronic diseases. Antioxid Redox Signal 2013, 18:1819-1892.
20. Dembitsky V.M. Astonishing diversity of natural surfactants: 5. Biologically active glycosides of aromatic metabolites. Lipids 2005, 40:869-900.
21. Deng M., Ju X.-D., Fan D.-S., Tu P.-F., Zhang J., Shen Y. Verbascoside rescues the SHSY5Y neuronal cells from MPP+-induced apoptosis. Chin Pharmacol Bull 2008, 24:1297-1301.
22. Di Giancamillo A., Rossi R., Vitari F., Carollo V., Deponti D., Corino C., et al. Changes in nitrosative stress biomarkers in swine intestine following dietary intervention with verbascoside. Histol Histopathol 2013, 28:715-723.
23. Duynstee H.I., de Koning M.C., Ovaa H., van der Marel G.A., van Boom J.H. Synthesis of verbascoside: a dihydroxyphenylethyl glycoside with diverse bioactivity. Eur J Org Chem 1999, 10:2623-2632.
24. Ellis B.E. Production of hydroxyphenylethanol glycosides in suspension cultures of Syringa vulgaris. Phytochemistry 1983, 22:1941-1943.
25. Esposito E., Mazzon E., Paterniti I., Dal Toso R., Pressi G., Caminiti R., et al. PPAR-a contributes to the anti-inflammatory activity of verbascoside in a model of inflammatory bowel disease. PPAR Res 2010, 917312. 10.1155/2010/917312.
26. Esposito E., Dal Toso R., Pressi G., Bramanti P., Meli R., Cuzzocrea S. Protective effect of verbascoside in activated C6 glioma cells: possible molecular mechanisms. Naunyn Schmiedebergs Arch Pharmacol 2010, 381:93-105.
27. Filho A.G., Morel A.F., Adolpho L., Ilha V., Giralt E., Tarragó T., et al. Inhibitory effect of verbascoside isolated from Buddleja brasiliensis Jacq. ex Spreng on prolyl oligopeptidase activity. Phytother Res 2012, 26:1472-1475.
28. Frum Y., Viljoen A.M., Van Heerden F.R. Verbascoside and luteolin-5-O-β-d-glucoside isolated from Halleria lucida L. exhibit antagonistic anti-oxidant properties in vitro. S Afr J Bot 2007, 73:583-587.
29. Funari C.S., Gullo F.P., Napolitano A., Carneiro R.L., Mendes-Giannini M.J., Fusco-Almeida A.M., et al. Chemical and antifungal investigations of six Lippia species (Verbenaceae) from Brazil. Food Chem 2012, 135:2086-2094.
30. Funes L., Fernandez-Arroyo S., Laporta O., Pons A., Roche E., Segura-Carretero A., et al. Correlation between plasma antioxidant capacity and verbascoside levels in rats after oral administration of lemon verbena extract. Food Chem 2009, 117:589-598.
31. Funes L., Carrera-Quintanar L., Cerdan-Calera M., Ferres M.D., Drobnic F., Pons A., et al. Effect of lemon verbena supplementation on muscular damage markers, proinflammatory cytokines release and neutrophils' oxidative stress in chronic exercise. Eur J Appl Physiol 2011, 111:695-705.
32. Georgiev M.I., Alipieva K., Orhan I., Abrashev R., Denev P., Angelova M. Antioxidant and cholinesterases inhibitory activities of Verbascum xanthophoeniceum Griseb. and its phenylethanoid glycosides. Food Chem 2011, 128:100-105.
33. Georgiev M.I., Ali K., Alipieva K., Verpoorte R., Choi Y.H. Metabolic differentiations and classification of Verbascum species by NMR-based metabolomics. Phytochemistry 2011, 72:2045-2051.
34. Georgiev M.I., Ludwig-Mueller J., Weber J., Stancheva N., Bley T. Bioactive metabolites production and stress-related hormones in devil's claw cell suspension cultures grown in bioreactors. Appl Microbiol Biotechnol 2011, 89:1683-1691.
35. Georgiev M.I., Ludwig-Mueller J., Alipieva K., Lippert A. Sonication-assisted Agrobacterium rhizogenes-mediated transformation of Verbascum xanthophoeniceum Griseb. for bioactive metabolite accumulation. Plant Cell Rep 2011, 30:859-866.
36. Georgiev M.I., Pastore S., Lulli D., Alipieva K., Kostyuk V., Potapovich A., et al. Verbascum xanthophoeniceum-derived phenylethanoid glycosides are potent inhibitors of inflammatory chemokines in dormant and interferon-gamma-stimulated human keratinocytes. J Ethnopharmacol 2012, 144:754-760.
37. Georgiev M.I., Eibl R., Zhong J.J. Hosting the plant cells in vitro: recent trends in bioreactors. Appl Microbiol Biotechnol 2013, 97:3787-3800.
38. Gómez-Aguirre Y.A., Zamilpa A., González-Cortazar M., Trejo-Tapia G. Adventitious root cultures of Castilleja tenuiflora Benth. as a source of phenylethanoid glycosides. Ind Crop Prod 2012, 36:188-195.
39. Guarnerio C.F., Fraccaroli M., Gonzo I., Pressi G., Dal Toso R., Guzzo F., et al. Metabolomic analysis reveals that the accumulation of specific secondary metabolites in Echinacea angustifolia cells cultured in vitro can be controlled by light. Plant Cell Rep 2012, 31:361-367.
40. Han L., Ji L., Boakye-Yiadom M., Li W., Song X., Gao X. Preparative isolation and purification of four compounds from Cistanches deserticola Y.C. Ma by high-speed counter-current chromatography. Molecules 2012, 17:8276-8284.
41. Harput U.S., Genc Y., Saracoglu I. Cytotoxic and antioxidative activities of Plantago lagopus L. and characterization of its bioactive compounds. Food Chem Toxicol 2012, 50:1554-1559.
42. Hausmann M., Obermeier F., Paper D.H., Balan K., Dunger N., Menzel K., et al. In vivo treatment with the herbal phenylethanoid acteoside ameriliorates intestinal inflammation in dextran sulphate sodium-induced colitis. Clin Exp Immunol 2007, 148:373-381.
43. He Z.D., Lau K.M., Xu H.X., Li P.C., Pui-Hay But P. Antioxidant activity of phenylethanoid glycosides from Brandisia hancei. J Ethnopharmacol 2000, 71:483-486.
44. Hennebelle T., Sahpaz S., Gressier B., Joseph H., Bailleul F. Antioxidant and neurosedative properties of polyphenols and iridoids from Lippia alba. Phytother Res 2008, 22:256-258.
45. Huang W., Wu S.-B., Wang Y.-L., Guo Z.-Y., Kennelly E.J., Long C.-L. Chemical constituents from Striga asiatica and its chemotaxonomic study. Biochem Syst Ecol 2013, 48:100-106.
46. Hung C.-Y., Tsai Y.-C., Li K.-Y. Phenolic antioxidants isolated from the flowers of Osmanthus fragrans. Molecules 2012, 17:10724-10737.
47. Isacchi B., Iacopi R., Bergonzi M.C., Ghelardini C., Galeotti N., Norcini M. Antihyperalgesic activity of verbascoside in two models of neuropathic pain. J Pharm Pharmacol 2011, 63:594-601.
48. Japón-Luján R., Janeiro P., De Castro M.D.L. Solid-liquid transfer of biophenols from olive leaves for the enrichment of edible oils by a dynamic ultrasound-assisted approach. J Agric Food Chem 2008, 56:7231-7235.
49. Jimenez C., Riguera R. Phenylethanoid glycosides in plants: structure and biological activity. Nat Prod Rep 1994, 11:591-606.
50. Kahraman C., Tatli I.I., Orhan I.E., Akdemir Z.S. Cholinesterase inhibitory and antioxidant properties of Verbascum mucronatum Lam. and its secondary metabolites. Z Naturforsch C 2010, 65:667-674.
51. Kirmizibekmez H., Ariburnu E., Masullo M., Festa M., Capasso A., Yesilada E., et al. Iridoid, phenylethanoid and flavonoid glycosides from Sideritis trojana. Fitoterapia 2012, 83:130-136.
52. Korkina L.G. Phenylethanoids as naturally occurring antioxidants: from plant defense to human health. Cell Mol Biol 2007, 53:15-25.
53. Korkina L.G., Pastore S. The role of redox regulation in the normal physiology and inflammatory diseases of skin. Front Biosci (Elite Ed) 2009, 1:123-141.
54. Korkina L.G., Mikhal'chik E., Suprun M.V., Pastore S., Dal Toso R. Molecular mechanisms underlying wound healing and anti-inflammatory properties of naturally occurring biotechnologically produced phenylethanoid glycosides. Cell Mol Biol (Noisy-le-Grand) 2007, 53:84-91.
55. Korkina L.G., Pastore S., De Luca C., Kostyuk V.A. Metabolism of plant polyphenols in the skin: beneficial versus deleterious effects. Curr Drug Metab 2008, 9:710-729.
56. Korkina L.G., De Luca C., Kostyuk V.A., Pastore S. Plant polyphenols and tumors: from mechanisms to therapies, prevention, and protection against toxicity of anti-cancer treatments. Curr Med Chem 2009, 16:3943-3965.
57. Korkina L.G., Kostyuk V., De Luca C., Pastore S. Plant phenylpropanoids as emerging anti-inflammatory agents. Mini Rev Med Chem 2011, 11:823-835.
58. Korkina L.G., Pastore S., Dellambra E., De Luca C. New molecular and cellular targets for chemoprevention and treatment of skin tumors by plant polyphenols: a critical review. Curr Med Chem 2013, 20:852-868.
59. Kostyuk V.A., Potapovich A., Suhan T., De Luca C., Pressi G., Dal Toso R., et al. Plant polyphenols against UV-C-induced cellular death. Planta Med 2008, 74:509-514.
60. Kostyuk V.A., Potapovich A.I., Suhan T.O., De Luca C., Korkina L.G. Antioxidant and signal modulation properties of plant polyphenols in controlling vascular inflammation. Eur J Pharmacol 2011, 658:248-256.
61. Kostyuk V.A., Potapovich A.I., Lulli D., Stancato A., De Luca C., Pastore S., et al. Modulation of human keratinocyte responses to solar UV by plant polyphenols as a basis for chemoprevention of non-melanoma skin cancers. Curr Med Chem 2013, 20:869-879.
62. Kurisu M., Miyamae Y., Murakami K., Han J., Isoda H., Irie K., et al. Inhibition of amyloid β aggregation by acteoside, a phenylethanoid glycoside. Biosci Biotechnol Biochem 2013, 77:1329-1332.
63. Lee J.Y., Woo E.R., Kang K.W. Inhibition of lipopolysaccharide-inducible nitric oxide synthase expression by acteoside through blocking of AP-1 activation. J Ethnopharmacol 2005, 97:561-566.
64. Lee J.H., Lee J.Y., Kang H.S., Jeong C.H., Moon H., Whang W.K., et al. The effect of acteoside on histamine release and arachidonic acid release in RBL-2H3 mast cells. Arch Pharm Res 2006, 29:508-513.
65. Lee K.Y., Jeong E.J., Lee H.S., Kim Y.C. Acteoside of Callicarpa dichotoma attenuates scopolamine-induced memory impairments. Biol Pharm Bull 2006, 29:71-74.
66. Lee K.W., Kim H.J., Lee Y.S., Park H.J., Choi J.W., Ha J., et al. Acteoside inhibits human promyelocytic HL-60 leukemia cell proliferation via inducing cell cycle arrest at G0/G1 phase and differentiation into monocytes. Carcinogenesis 2007, 28:1928-1936.
67. Lenoir L., Rossary A., Joubert-Zakeyh J., Vergnaud-Gauduchon J., Farges M.C., Fraisse D., et al. Lemon verbena infusion consumption attenuates oxidative stress in dextran sulfate sodium-induced colitis in the rat. Dig Dis Sci 2011, 56:3534-3545.
68. Li J., Ge R.C., Zheng R.L., Liu Z.M., Jia Z.J. Antioxidative and chelating activities of phenylpropanoid glycosides from Pedicularis striata. Zhongguo Yao Li Xue Bao 1997, 18:77-80.
69. Li J.X., Xin D., Li H., Lu J.F., Tong C.W., Gao J.N., et al. Effect of verbascoside on decreasing concentration of oxygen free radicals and lipid peroxidation in skeletal muscle. Zhongguo Yao Li Xue Bao 1999, 20:126-130.
70. Li Y.M., Han Z.H., Jiang S.H., Jiang Y., Yao S.D., Zhu D.Y. Fast repairing of oxidized OH radical adducts of dAMP and dGMP by phenylethanoid glycosides from Scrophularia ningpoensis Hemsl. Acta Pharmacol Sin 2000, 21:1125-1128.
71. Li Y., Gan L., Li G.Q., Deng L., Zhang X., Deng Y. Pharmacokinetics of plantamajoside and acteoside from Plantago asiatica in rats by liquid chromatography-mass spectrometry. J Pharm Biomed Anal 2014, 89:251-256.
72. Lim E.-K., Bowles D. Plant production systems for bioactive small molecules. Curr Opin Biotechnol 2012, 23:271-277.
73. Lin J., Gao L., Huo S.X., Peng X.M., Wu P.P., Cai L.M., et al. Effect of acteoside on learning and memory impairment induced by scopolamine in mice. Zhongguo Zhong Yao Za Zhi 2012, 37:2956-2959.
74. Liu J.Y., Guo Z.G., Zeng Z.L. Improved accumulation of phenylethanoid glycosides be precursor feeding to suspension culture of Cistanche salsa. Biochem Eng J 2007, 33:88-93.
75. Martin K.R., Appel C.L. Polyphenols as dietary supplements: a double-edged sword. Nutr Diet Suppl 2010, 2:1-12.
76. Martin-Nizard F., Sahpaz S., Furman C., Fruchart J.C., Duriez P., Bailleul F. Natural phenylethanoids protect endothelial cells against oxidized LDL-induced cytotoxicity. Planta Med 2003, 69:207-211.
77. Marzocco S., Piccinelli A.L., Rastrelli L., Mazzon E., Cuzzocrea S., Autore G. Inhibition of inducible nitric oxide synthase in vitro and in vivo by a water-soluble extract of Wendita calysina leaves. Naunyn Schmiedebergs Arch Pharmacol 2007, 375:349-358.
78. Mazzon E., Esposito E., Di Paola R., Riccardi L., Caminiti R., Dal Toso R., et al. Effects of verbascoside biotechnologically produced by Syringa vulgaris plant cell cultures in rodent model of colitis. Naunyn Schmiedebergs Arch Pharmacol 2009, 380:79-94.
79. Mestre-Alfaro A., Ferrer M.D., Sureda A., Tauler P., Marttinez E., Bibiloni M.M., et al. Phytoestrogens enhance antioxidant enzymes after swimming exercise and modulate sex hormone plasma levels in female swimmers. Eur J Appl Physiol 2011, 111:2281-2294.
80. Motojima H., Villareal M.O., Iijima R., Han J., Isoda H. Acteoside inhibits type I allergy through the down-regulation of Ca/NFAT and JNK MAPK signaling pathways in basophilic cells. J Nat Med 2013, 67:790-798.
81. Muñoz E., Avila J.G., Alarcón J., Kubo I., Werner E., Céspedes C.L. Tyrosinase inhibitors from Calceolaria integrifolia s.l.: Calceolaria talcana aerial parts. J Agric Food Chem 2013, 61:4336-4343.
82. Obied H.K., Bedgood D.R., Prenzler P.D., Robards K. Bioscreening of Australian olive mill waste extracts: Biophenol content, antioxidant, antimicrobial and molluscicidal activities. Food Chem Toxicol 2007, 45:1238-1248.
83. Ouitas N.A., Heard C.M. A novel ex vivo skin model for the assessment of the potential transcutaneous anti-inflammatory effect of topically applied Harpagophytum procumbens extract. Int J Pharm 2009, 376:63-68.
84. Oyourou J.-N., Combrinck S., Regnier T., Marston A. Purification, stability and antifungal activity of verbascoside from Lippia javanica and Lantana camara leaf extracts. Ind Crop Prod 2013, 43:820-826.
85. Paola R.D., Oteri G., Mazzon E., Crisafulli C., Galuppo M., Toso R.D., et al. Effects of verbascoside, biotechnologically purified by Syringa vulgaris plant cell cultures, in a rodent model of periodontitis. J Pharm Pharmacol 2011, 63:707-717.
86. Papoutsi Z., Kassi E., Mitakou S., Aligiannis N., Tsiapara A., Chrousos G.P., et al. Acteoside and martynoside exhibit estrogenic/antiestrogenic properties. J Steroid Biochem Mol Biol 2006, 98:63-71.
87. Pastore S., Korkina L. Redox imbalance in T cell-mediated skin diseases. Mediators Inflamm 2010, 2010:861949.
88. Pastore S., Potapovich A., Kostyuk V., Mariani V., Lulli D., De Luca C., et al. Plant polyphenols effectively protect HaCaT cells from ultraviolet C-triggered necrosis and suppress inflammatory chemokine expression. Ann N Y Acad Sci 2009, 1171:305-311.
89. Pastore S., Lulli D., Fidanza P., Potapovich A.I., Kostyuk V.A., De Luca C., et al. Plant polyphenols regulate chemokine expression and tissue repair in human keratinocytes through interaction with cytoplasmic and nuclear components of epidermal growth factor receptor system. Antioxid Redox Signal 2012, 16:314-328.
90. Pastore S., Lulli D., Pascarella A., Maurelli R., Dellambra E., Potapovich A., et al. Resveratrol enhances solar UV-induced responses in normal human epidermal keratinocytes. Photochem Photobiol 2012, 88:1522-1530.
91. Pastore S., Lulli D., Maurelli R., Dellambra E., De Luca C., Korkina L.G. Resveratrol induces long-lasting IL-8 expression and peculiar EGFR activation/distribution in human keratinocytes: mechanisms and implications for skin administration. PLoS One 2013, 8:e59632.
92. Pendota S.C., Aderogba M.A., Ndhlala A.R., Van Staden J. Antimicrobial and acetylcholinesterase inhibitory activities of Buddleja salviifolia (L.) Lam. leaf extracts and isolated compounds. J Ethnopharmacol 2013, 148:515-520.
93. Phakeovilay C., Disadee W., Sahakitpichan P., Sitthimonchai S., Kittakoop P., Ruchirawat S., et al. Phenylethanoid and flavone glycosides from Ruellia tuberosa L. J Nat Med 2013, 67:228-233.
94. Picerno P., Autore G., Marzocco S., Meloni M., Sanogo R., Aquino R.P. Anti-inflammatory activity of verminoside from Kigelia africana and evaluation of cutaneous irritation in cell cultures and reconstituted human epidermis. J Nat Prod 2005, 68:1610-1614.
95. Potapovich A.I., Lulli D., Fidanza P., Kostyuk V.A., De Luca C., Pastore S., et al. Plant polyphenols differentially modulate inflammatory responses of human keratinocytes by interfering with activation of transcription factors NFκB and AhR and EGFR-ERK pathway. Toxicol Appl Pharmacol 2011, 255:138-149.
96. Potapovich A.I., Kostyuk V.A., Kostyuk T.V., de Luca C., Korkina L.G. Effects of pre- and post-treatment with plant polyphenols on human keratinocyte responses to solar UV. Inflamm Res 2013, 62:773-780.
97. Pu X., Song Z., Li Y., Tu P., Li H. Acteoside from Cistanche salsa inhibits apoptosis by 1-methyl-4-phenylpyridinium ion in cerebellar granule neurons. Planta Med 2003, 69:65-66.
98. Quirantes-Piné R., Funes L., Micol V., Segura-Carretero A., Fernández-Gutiérrez A. High-performance liquid chromatography with diode array detection coupled to electrospray time-of-flight and ion-trap tandem mass spectrometry to indentify phenolic compounds from a lemon verbena extract. J Chromatogr A 2009, 1216:5391-5397.
99. Quirantes-Piné R., Herranz-Lopez M., Funes L., Borrás-Linares I., Micol V., Segura-Carretero A., et al. Phenylpropanoids and their metabolites are the major compounds responsible for blood-cell protection against oxidative stress after administration of Lippia citriodora in rats. Phytomedicine 2013, 20:1112-1118.
100. Quirantes-Piné R., Zurek G., Barrajón-Catalán E., Bässmann C., Micol V., Segura-Carretero A., et al. A metabolite-profiling approach to assess the uptake and metabolism of phenolic compounds from olive leaves in SKBR3 cells by HPLC-ESI-QTOF-MS. J Pharm Biomed Anal 2013, 72:121-126.
101. Rao Y.K., Fang S.H., Hsieh S.C., Yeh T.H., Tzeng Y.M. The constituents of Anisomeles indica and their anti-inflammatory activities. J Ethnopharmacol 2009, 121:292-296.
102. Saimaru H., Orihara Y. Biosynthesis of acteoside in cultured cells of Olea europaea. J Nat Med 2010, 64:139-145.
103. Sakurai A., Kato T. A new glycoside, kusaginin isolated from Clerodendron trichotomum. Bull Chem Soc Jpn 1983, 56:1573-1574.
104. Sanchez P.M., Villarreal M.L., Herrera-Ruiz M., Zamilpa A., Jiménez-Ferrer E., Trejo-Tapia G. In vivo anti-inflammatory and anti-ulcerogenic activities of extracts from wild growing and in vitro plants of Castilleja tenuiflora Benth. (Orobanchaceae). J Ethnopharmacol 2013, 150:1032-1037.
105. Santos R.X., Correia S.C., Zhu X., Smith M.A., Moreira P.I., Castellani R.J., et al. Mitochondrial DNA oxidative damage and repair in aging and Alzheimer's disease. Antioxid Redox Signal 2013, 18:2444-2457.
106. Scarpati M.L., Monache D. Isolation from Verbascum sinuatum of two new glucosides, verbascoside and isoverbascoside. Ann Chim 1963, 53:356-367.
107. Schapira A.H. Etiology of Parkinson's disease. Neurology 2006, 66:S10-S23.
108. Schlauer J., Budzianowski J., Kukulczanka K., Ratajczak L. Acteoside and related phenylethanoid glycosides in Byblis liniflora Salisb. plants propagated in vitro and its systematic significance. Acta Soc Bot Pol 2004, 73:9-15.
109. Schmitt S., Schaefer U.F., Doebler L., Reichling J. Cooperative interaction of monoterpenes and phenylpropanoids on the in vitro human skin permeation of complex composed essential oils. Planta Med 2009, 75:1381-1385.
110. Seidel V., Verholle M., Malard Y., Tillequin F., Fruchart J.C., Duriez P., et al. Phenylpropanoids from Ballota nigra L. inhibit in vitro LDL peroxidation. Phytother Res 2000, 14:93-98.
111. Seo E.S., Oh B.K., Pak J.H., Yim S.H., Gurunathan S., Kim Y.P., et al. Acteoside improves survival in cecal ligation and puncture-induced septic mice via blocking of high mobility group box 1 release. Mol Cells 2013, 35:348-354.
112. Sgarbossa A., Dal Bosco M., Pressi G., Cuzzocrea S., Dal Toso R., Menegazzi M. Phenylethanoid glycosides from plant cell cultures induce heme oxygenase 1 gene expression in a human keratinocyte cell line by affecting the balance of NRF2 and BACH1 transcription factors. Chem Biol Interact 2012, 199:87-95.
113. Shaulian E., Karin M. AP-1 in cell proliferation and survival. Oncogene 2001, 20:2390-2400.
114. Sheng G.-Q., Zhang J.-R., Pu X.-P., Ma J., Li C.-L. Protective effect of verbascoside on 1-methyl-4-phenylpyridinium ion-induced neurotoxicity in PC12 cells. Eur J Pharmacol 2002, 451:119-124.
115. Si C.-L., Liu S.-C., Hu H.-Y., Jiang J.-Z., Yu G.-J., Ren X.-D., et al. Activity-guided screening of the antioxidants from Paulownia tomentosa var. tomentosa bark. Bioresources 2013, 8:628-637.
116. Sinico C., Caddeo C., Valenti D., Fadda A.M., Bilia A.R., Vinceri F.F. Liposomes as carriers for verbascoside: stability and skin permeation studies. J Liposome Res 2008, 18:83-90.
117. Son Y.O., Lee S.A., Kim S.S., Jang Y.S., Chun J.C., Lee J.C. Acteoside inhibits melanogenesis in B16F10 cells through ERK activation and tyrosinase down-regulation. J Pharm Pharmacol 2011, 63:1309-1319.
118. Song H.S., Sim S.S. Acteoside inhibits alpha-MSH-induced melanin production in B16 melanoma cells by inactivation of adenyl cyclase. J Pharm Pharmacol 2009, 61:1347-1351.
119. Song H.S., Choi M.Y., Ko M.S., Jeong J.M., Kim Y.H., Jang B.H., et al. Competitive inhibition of cytosolic Ca2+-dependent phospholipase A2 by acteoside in RBL-2H3 cells. Arch Pharm Res 2012, 35:905-910.
120. Speranza L., Franceschelli S., Pesce M., Reale M., Menghini L., Vinciguerra I., et al. Antiinflammatory effects in THP-1 cells treated with verbascoside. Phytother Res 2010, 24:1398-1404.
121. Tai B.H., Jung B.Y., Cuong N.M., Linh P.T., Tung N.H., Nhiem N.X., et al. Total peroxynitrite scavenging capacity of phenylethanoid and flavonoid glycosides from the flowers of Buddleja officinalis. Biol Pharm Bull 2009, 32:1952-1956.
122. Taskova R.M., Gotfredsen C.H., Jensen S.R. Chemotaxonomic markers in Digitalideae (Plantaginaceae). Phytochemistry 2005, 66:1440-1447.
123. Vertuani S., Beghelli E., Scalambra E., Malisardi G., Copetti S., Dal Toso R., et al. Activity and stability studies of verbascoside, a novel antioxidant, in dermo-cosmetic and pharmaceutical topical formulations. Molecules 2011, 16:7068-7080.
124. Wang H., Xu Y., Yan J., Zhao X., Sun X., Zhang Y., et al. Acteoside protects human neuroblastoma SH-SY5Y cells against beta-amyloid-induced cell injury. Brain Res 2009, 1283:139-147.
125. Wang H.Q., Xu Y.X., Zhu C.Q. Upregulation of heme oxygenase-1 by acteoside through ERK and PI3 K/Akt pathway confer neuroprotection against beta-amyloid-induced neurotoxicity. Neurotox Res 2012, 21:368-378.
126. Wartenberg M., Budde P., De Marees M., Grunheck F., Tsang S.Y., Huang Y., et al. Inhibition of tumor-induced angiogenesis and matrix-metalloproteinase expression in confrontation culture of embryoid bodies and tumor spheroids by plant ingredients used in traditional Chinese medicine. Lab Invest 2003, 83:87-98.
127. Wong I.Y., He Z.D., Huang Y., Chen Z.Y. Antioxidative activities of phenylethanoid glycosides from Ligustrum purpurascens. J Agric Food Chem 2001, 49:3113-3119.
128. Wu Y.T., Lc Lin, Sung J.S., Tsai T.H. Determination of acteoside in Cistanche deserticola and Boschniakia rossica and its pharmacokinetics in freely-moving rats using LC-MS/MS. J Chromatogr B 2006, 844:89-95.
129. Wysokinska H., Rozga M. Establishment of transformed root cultures of Paulownia tomentosa for verbascoside production. J Plant Physiol 1998, 152:78-83.
130. Xiong Q., Tezuka Y., Kaneko T., Li H., Tran L.Q., Hase K., et al. Inhibition of nitric oxide by phenylethanoids in activated macrophages. Eur J Pharmacol 2000, 400:137-144.
131. 2 induces mitochondrial-mediated, MAPK- and caspase-independent growth inhibition and cytotoxicity in human gingival fibroblasts. Toxicol In Vitro 2012, 26:561-570.
132. Yue H.L., Zhao X.H., Lei L.J., Shao Y. Separation and purification of five phenylpropanoid glycosides from Lamiophlomis rotata (Benth.) Kudo by a macroporous resin column combined with high-speed counter-current chromatography. J Sep Sci 2013, 36:3123-3129.
133. Zaabat N., Hay A.E., Michalet S., Darbour N., Bayet C., Skandrani I., et al. Antioxidant and antigenotoxic properties of compounds isolated from Marrubium deserti de Noé. Food Chem Toxicol 2011, 49:3328-3335.
134. Zenz R., Eferl R., Scheinecker C., Redlich K., Smolen J., Schonthaler H.B., et al. Activator protein 1 (Fos/Jun) functions in inflammatory bone and skin disease. Arthritis Res Ther 2008, 10:201. 10.1186/ar2338.
135. Zhang F., Jia Z., Deng Z., Wei Y., Zheng R., Yu L. In vitro modulation of telomerase activity, telomere length and cell cycle in MKN45 cells by verbascoside. Planta Med 2002, 68:115-118.
136. Zhao C., Dodin G., Yuan C., Chen H., Zheng R., Jia Z., et al. In vitro protection of DNA from Fenton reaction by plant polyphenol verbascoside. Biochim Biophys Acta 2005, 1723:114-123.
137. Zhou A., Sadik A.O. Comparative analysis of quercetin oxidation by electrochemical, enzymatic, autoxidation, and free radical generation techniques: a mechanistic study. J Agric Food Chem 2008, 56:12081-12091.