Verbascoside: Difference between revisions

|Verifiedfields = changed

|Watchedfields = changed

|verifiedrevid = 406122558

|Name = Verbascoside

|ImageFile = Acteoside.svg

|ImageName = Chemical structure of verbascoside

|ImageAlt = Chemical structure of verbascoside

|IUPACName = 2-(3,4-Dihydroxyphenyl)ethyl α-{{small|L}}-rhamnopyranosyl-(1→4)-<nowiki/>{5-''O''-[(2''E'')-3-(3,4-dihydroxymethyl)prop-2-enoyl]-β-{{small|D}}-glucopyranoside}

|SystematicName = (2''R'',3''R'',4''R'',5''R'',6''R'')-6-[2-(3,4-Dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-<nowiki/>{[(2''S'',3''R'',4''R'',5''R'',6''S'')-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2''E'')-3-(3,4-dihydroxymethyl)prop-2-enoate

|OtherNames = Acteoside<br>Kusaginin<br>Orobanchin

|Section1={{Chembox Identifiers

|CASNo = 61276-17-3

|CASNo_Ref = {{cascite|correct|??}}

|UNII_Ref = {{fdacite|correct|FDA}}

|UNII = 3TGX09BD5B

|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

|Section2={{Chembox Properties

| C=29 | H=36 | O=15

'''Verbascoside''' is a [[polyphenol]] glycoside<ref>{{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|bibcode=2005PChem..66.1440T }}</ref> 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.<ref name="Andary et al 1982"/>

== Occurrences ==

=== Natural occurrences ===

Verbascoside can be found in species in all the families of the order [[Lamiales]] (syn. Scrophulariales).<ref name=Schlauer>{{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 |doi-access=free}}</ref> Only two examples are known from outside the order,<ref name=Grevenstuk>{{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|bibcode=2009BioSE..37..285G }}</ref> in the clade [[Asterids]].

; in the Lamiales

In the family [[Lamiaceae]], it can be found in the medicinal plants in the genus ''[[Phlomis]]'',<ref>{{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 |doi-access=free }}</ref> in the [[Scrophulariaceae]], in ''[[Verbascum phlomoides]]'',<ref>{{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|s2cid=37043342 }}</ref> ''[[Verbascum mallophorum]]'',<ref name=pmid19828096>{{cite journal |pmid=19828096 |year=2009 |title=Anti-inflammatory properties of the plant Verbascum mallophorum |journal=Journal of Biological Regulators and Homeostatic Agents |volume=23 |issue=3 |pages=189–95|last1=Speranza |first1=L. |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.}}</ref> or, in the family [[Buddlejaceae]], in ''[[Buddleja globosa]]''<ref name=pmid8258981>{{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}}</ref> or ''[[Buddleja cordata]]'',<ref name=pmid10432210>{{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}}</ref> in the family [[Bignoniaceae]], in ''[[Pithecoctenium]] sp'' and ''[[Tynanthus panurensis]]'', in the family [[Orobanchaceae]], in ''[[Cistanche]] sp'' and ''[[Orobanche rapum-genistae]]'',<ref name="Andary et al 1982">{{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|bibcode=1982PChem..21.1123A }}</ref> in the [[Plantaginaceae]], in ''[[Plantago lanceolata]]'',<ref>{{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|s2cid=260249396 }}</ref> in [[Verbenaceae]], in ''[[Verbena officinalis]]'' (common vervain),<ref>{{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|s2cid=24506417 }}</ref> ''[[Aloysia citrodora]]'' (lemon verbena) and ''[[Lantana camara]]'',<ref name=pmid1812212>{{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}}</ref> in the [[Oleaceae]], in ''Olea europaea'' ([[olive]]),<ref>{{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}}</ref> in the [[Lentibulariaceae]], in the carnivorous plant ''[[Pinguicula lusitanica]]'',<ref name=Grevenstuk/> and, in the Byblidaceae, in ''[[Byblis liniflora]]''.<ref name=Schlauer/>

=== Derivatives ===

Verbascoside derivatives can be found in the ''[[Verbascum undulatum]]''<ref>{{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}}</ref> and notably [[apioside]]s in ''[[Verbascum]] sp''.<ref>{{cite journal |pmid=8960288 |year=1996 |last1=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}}</ref>

=== In ''in vitro'' cultures ===

It can also be produced in [[plant cell culture]]s of ''[[Leucosceptrum]] sp'' ([[Lamiaceae]]) and ''[[Syringa]] sp'' ([[Oleaceae]]).<ref>{{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 |pages=484–487 |pmid=24213785 |s2cid=32914451 }}</ref> It can also be produced in [[hairy root]]s cultures of ''[[Paulownia tomentosa]]'' (empress tree, [[Paulowniaceae]]).<ref>{{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}}</ref>

== Biological activity ==

Verbascoside has an [[antimicrobial]] activity,<ref name=pmid8258981/> notably against ''[[Staphylococcus aureus]]''.<ref name=pmid10432210/> It can also have [[anti-inflammatory]] properties.<ref name=pmid19828096/>

Although some ''[[in vitro]]'' [[genotoxicity]] of verbascoside has been reported on human [[lymphocyte]]s with an involvement of [[PARP-1]] and [[p53 protein]]s,<ref>{{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}}</ref> subsequent ''[[in vivo]]'' tests reported no genotoxicity for high dosage oral administration.<ref>{{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}}</ref> It is a [[protein kinase C]] inhibitor.<ref name=pmid1812212/>

== See also ==

* [[Echinacoside]]

== References ==

{{reflist}}

{{Hydroxycinnamic acid}}

[[Category:Phenylpropanoid glycosides]]

[[Category:Phenylethanoids]]

[[Category:Esters]]

[[Category:Rhamnosides]]

[[Category:Polyols]]