| 词条 | Verbascoside |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 406122558 | Name = Verbascoside | ImageFile = Acteoside.svg | ImageName = Chemical structure of verbascoside | ImageAlt = Chemical structure of verbascoside | IUPACName = [(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 | OtherNames = Acteoside Kusaginin Orobanchin |Section1={{Chembox Identifiers | CASNo = 61276-17-3 | CASNo_Ref = {{cascite|correct|??}} | CASNoOther = | PubChem = 5281800 | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 132853 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 231853 | SMILES = C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H](O[C@@H]([C@H]2OC(=O)/C=C/C3=CC(=C(C=C3)O)O)CO)OCCC4=CC(=C(C=C4)O)O)O)O)O)O | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 4445112 | InChI = 1/C29H36O15/c1-13-22(36)23(37)24(38)29(41-13)44-27-25(39)28(40-9-8-15-3-6-17(32)19(34)11-15)42-20(12-30)26(27)43-21(35)7-4-14-2-5-16(31)18(33)10-14/h2-7,10-11,13,20,22-34,36-39H,8-9,12H2,1H3/b7-4+/t13-,20+,22-,23+,24+,25+,26+,27+,28+,29-/m0/s1 | InChIKey = FBSKJMQYURKNSU-ZLSOWSIRBQ | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C29H36O15/c1-13-22(36)23(37)24(38)29(41-13)44-27-25(39)28(40-9-8-15-3-6-17(32)19(34)11-15)42-20(12-30)26(27)43-21(35)7-4-14-2-5-16(31)18(33)10-14/h2-7,10-11,13,20,22-34,36-39H,8-9,12H2,1H3/b7-4+/t13-,20+,22-,23+,24+,25+,26+,27+,28+,29-/m0/s1 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = FBSKJMQYURKNSU-ZLSOWSIRSA-N | MeSHName = }} |Section2={{Chembox Properties | C=29 | H=36 | O=15 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} }}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] OccurrencesNatural occurrencesVerbascoside 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 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] DerivativesVerbascoside derivatives can be found in the Verbascum undulatum[14] and notably apiosides in Verbascum sp.[15] In in vitro culturesIt 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 activityVerbascoside 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
References1. ^{{cite journal |doi=10.1016/j.phytochem.2005.04.020 |pmid=15907957 |title=Chemotaxonomic markers in Digitalideae (Plantaginaceae) |journal=Phytochemistry |volume=66 |issue=12 |pages=1440–7 |year=2005 |last1=Taskova |first1=Rilka Mladenova |last2=Gotfredsen |first2=Charlotte Held |last3=Jensen |first3=Søren Rosendal }} {{Hydroxycinnamic acid}}2. ^1 {{cite journal |doi=10.5586/asbp.2004.002 |title=Acteoside and related phenylethanoid glycosides in Byblis liniflora Salisb. Plants propagated in vitro and its systematic significance |journal=Acta Societatis Botanicorum Poloniae |volume=73 |issue=1 |pages=9–15 |year=2011 |last1=Schlauer |first1=Jan |last2=Budzianowski |first2=Jaromir |last3=Kukułczanka |first3=Krystyna |last4=Ratajczak |first4=Lidia }} 3. ^1 {{cite journal |doi=10.1016/j.bse.2009.05.003 |title=Iridoid and caffeoyl phenylethanoid glycosides of the endangered carnivorous plant Pinguicula lusitanica L. (Lentibulariaceae) |journal=Biochemical Systematics and Ecology |volume=37 |issue=4 |pages=285–9 |year=2009 |last1=Grevenstuk |first1=Tomás |last2=Van Der Hooft |first2=Justin J.J |last3=Vervoort |first3=Jacques |last4=De Waard |first4=Pieter |last5=Romano |first5=Anabela }} 4. ^{{cite journal |doi=10.1186/2008-2231-22-32 |pmid=24650578 |pmc=3998186 |title=Quantification of verbascoside in medicinal species of Phlomis and their genetic relationships |journal=DARU Journal of Pharmaceutical Sciences |volume=22 |issue=1 |pages=32 |year=2014 |last1=Sarkhail |first1=Parisa |last2=Nikan |first2=Marjan |last3=Sarkheil |first3=Pantea |last4=Gohari |first4=Ahmad R |last5=Ajani |first5=Yousef |last6=Hosseini |first6=Rohollah |last7=Hadjiakhoondi |first7=Abbass |last8=Saeidnia |first8=Soodabeh }} 5. ^{{cite journal |doi=10.1007/s10600-007-0240-9 |title=Verbascoside from Verbascum phlomoides |journal=Chemistry of Natural Compounds |volume=43 |issue=6 |pages=710–1 |year=2007 |last1=Gvazava |first1=L. N |last2=Kikoladze |first2=V. S }} 6. ^1 {{cite journal |pmid=19828096 |year=2009 |author1=Speranza |first1=L |title=Anti-inflammatory properties of the plant Verbascum mallophorum |journal=Journal of biological regulators and homeostatic agents |volume=23 |issue=3 |pages=189–95 |last2=Franceschelli |first2=S |last3=Pesce |first3=M |last4=Menghini |first4=L |last5=Patruno |first5=A |last6=Vinciguerra |first6=I |last7=De Lutiis |first7=M. A |last8=Felaco |first8=M |last9=Felaco |first9=P |last10=Grilli |first10=A }} 7. ^1 {{cite journal |doi=10.1016/0378-8741(93)90041-3 |pmid=8258981 |title=Isolation of verbascoside, an antimicrobial constituent of Buddleja globosa leaves |journal=Journal of Ethnopharmacology |volume=39 |issue=3 |pages=221–2 |year=1993 |last1=Pardo |first1=F |last2=Perich |first2=F |last3=Villarroel |first3=L |last4=Torres |first4=R }} 8. ^1 {{cite journal |doi=10.1016/S0378-8741(98)00203-7 |pmid=10432210 |title=Mode of action of Buddleja cordata verbascoside against Staphylococcus aureus |journal=Journal of Ethnopharmacology |volume=66 |issue=1 |pages=75–8 |year=1999 |last1=Guillermo Avila |first1=José |last2=De Liverant |first2=Juliana G |last3=Martı́Nez |first3=Andrés |last4=Martı́Nez |first4=Gabriel |last5=Muñoz |first5=José Luis |last6=Arciniegas |first6=Amira |last7=Romo De Vivar |first7=Alfonso }} 9. ^1 {{cite journal |doi=10.1016/S0031-9422(00)82429-2 |title=Structures of verbascoside and orobanchoside, caffeic acid sugar esters from Orobanche rapum-genistae |journal=Phytochemistry |volume=21 |issue=5 |pages=1123–7 |year=1982 |last1=Andary |first1=C |last2=Wylde |first2=R |last3=Laffite |first3=C |last4=Privat |first4=G |last5=Winternitz |first5=F }} 10. ^{{cite journal |doi=10.1055/s-2006-958143 |pmid=7480214 |title=Phenylethanoids in the Herb of Plantago lanceolataand Inhibitory Effect on Arachidonic Acid-Induced Mouse Ear Edema1 |journal=Planta Medica |volume=61 |issue=5 |pages=479–80 |year=2007 |last1=Murai |first1=Michiko |last2=Tamayama |first2=Yasuhiko |last3=Nishibe |first3=Sansei }} 11. ^{{cite journal |doi=10.1002/1099-1573(200009)14:6<463::AID-PTR611>3.0.CO;2-G |pmid=10960904 |title=Antiinflammatory activity and chemical composition of extracts of Verbena officinalis |journal=Phytotherapy Research |volume=14 |issue=6 |pages=463–5 |year=2000 |last1=Deepak |first1=Mundkinajeddu |last2=Handa |first2=Sukhdev Swami }} 12. ^1 {{cite journal |doi=10.1021/np50078a016 |pmid=1812212 |title=Verbascoside Isolated from Lantana camara, an Inhibitor of Protein Kinase C |journal=Journal of Natural Products |volume=54 |issue=6 |pages=1595–600 |year=1991 |last1=Herbert |first1=J. M |last2=Maffrand |first2=J. P |last3=Taoubi |first3=K |last4=Augereau |first4=J. M |last5=Fouraste |first5=I |last6=Gleye |first6=J }} 13. ^{{cite journal |doi=10.1021/jf204001p |pmid=22268549 |title=Verbascoside, Isoverbascoside, and Their Derivatives Recovered from Olive Mill Wastewater as Possible Food Antioxidants |journal=Journal of Agricultural and Food Chemistry |volume=60 |issue=7 |pages=1822–9 |year=2012 |last1=Cardinali |first1=Angela |last2=Pati |first2=Sandra |last3=Minervini |first3=Fiorenza |last4=d'Antuono |first4=Isabella |last5=Linsalata |first5=Vito |last6=Lattanzio |first6=Vincenzo }} 14. ^{{cite journal |doi=10.1080/10575639808048278 |title=Verbascoside Derivatives and Iridoid Glycosides from Verbascum Undulatum |journal=Natural Product Letters |volume=12 |issue=2 |pages=111–5 |year=1998 |last1=Magiatis |first1=P |last2=Mitaku |first2=S |last3=Tsitsa |first3=E |last4=Skaltsounis |first4=A. L |last5=Harvala |first5=C }} 15. ^{{cite journal |pmid=8960288 |year=1996 |author1=Klimek |first1=B |title=6'-0-apiosyl-verbascoside in the flowers of mullein (Verbascum species) |journal=Acta poloniae pharmaceutica |volume=53 |issue=2 |pages=137–40 }} 16. ^{{cite journal |doi=10.1007/BF00232101 |title=Verbascoside production by plant cell cultures |journal=Plant Cell Reports |volume=9 |issue=9 |year=1991 |last1=Inagaki |first1=Nobuyuki |last2=Nishimura |first2=Hiroaki |last3=Okada |first3=Minoru |last4=Mitsuhashi |first4=Hiroshi }} 17. ^{{cite journal |doi=10.1016/S0176-1617(98)80105-3 |title=Establishment of transformed root cultures of Paulownia tomentosa for verbascoside production |journal=Journal of Plant Physiology |volume=152 |issue=1 |pages=78–83 |year=1998 |last1=Wysokiińska |first1=H |last2=Rózga |first2=M }} 18. ^{{cite journal |doi=10.1016/j.toxlet.2008.02.006 |pmid=18395372 |title=Verminoside- and verbascoside-induced genotoxicity on human lymphocytes: Involvement of PARP-1 and p53 proteins |journal=Toxicology Letters |volume=178 |issue=2 |pages=71–6 |year=2008 |last1=Santoro |first1=Antonietta |last2=Bianco |first2=Giuseppe |last3=Picerno |first3=Patrizia |last4=Aquino |first4=Rita Patrizia |last5=Autore |first5=Giuseppina |last6=Marzocco |first6=Stefania |last7=Gazzerro |first7=Patrizia |last8=Lioi |first8=Maria Brigida |last9=Bifulco |first9=Maurizio }} 19. ^{{cite journal |doi=10.1016/j.fct.2011.12.006 |pmid=22197714 |title=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 |journal=Food and Chemical Toxicology |volume=50 |issue=3–4 |pages=1082–90 |year=2012 |last1=Santos-Cruz |first1=Luis Felipe |last2=Ávila-Acevedo |first2=José Guillermo |last3=Ortega-Capitaine |first3=Diego |last4=Ojeda-Duplancher |first4=Jesús Clemente |last5=Perdigón-Moya |first5=Juana Laura |last6=Hernández-Portilla |first6=Luis Barbo |last7=López-Dionicio |first7=Héctor |last8=Durán-Díaz |first8=Ángel |last9=Dueñas-García |first9=Irma Elena |last10=Castañeda-Partida |first10=Laura |last11=García-Bores |first11=Ana María |last12=Heres-Pulido |first12=María Eugenia }} 2 : Phenylpropanoid glycosides|Phenylethanoids |
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