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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:46:20 UTC
Update Date2019-07-23 06:17:03 UTC
HMDB IDHMDB0034843
Secondary Accession Numbers
  • HMDB34843
Metabolite Identification
Common NameActeoside
DescriptionActeoside, also known as kusaginin or verbascoside, belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Verbascoside is a caffeoyl phenylethanoid glycoside 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. Only two examples are known from outside the order, in the clade Asterids.in the LamialesIn the family Lamiaceae, it can be found in the medicinal plants in the genus Phlomis, in the Scrophulariaceae, in Verbascum phlomoides, Verbascum mallophorum, or, in the family Buddlejaceae, in Buddleja globosa or Buddleja cordata, in the family Bignoniaceae, in Pithecoctenium sp and Tynanthus panurensis, in the family Orobanchaceae, in Cistanche sp and Orobanche rapum-genistae, in the Plantaginaceae, in Plantago lanceolata, in Verbenaceae, in Verbena officinalis (common vervain), Aloysia citrodora (lemon verbena) and Lantana camara, in the Oleaceae, in Olea europaea (olive), in the Lentibulariaceae, in the carnivorous plant Pinguicula lusitanica, and, in the Byblidaceae, in Byblis liniflora. Acteoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Acteoside is found, on average, in the highest concentration within a few different foods, such as common verbena, lemon verbena, and olives. Acteoside has also been detected, but not quantified in, a few different foods, such as bitter gourds, fruits, and sesames. This could make acteoside a potential biomarker for the consumption of these foods. Although some in vitro genotoxicity of verbascoside has been reported on human lymphocytes with an involvement of PARP-1 and p53 proteins, subsequent in vivo tests reported no genotoxicity for high dosage oral administration. It can also have anti-inflammatory properties. It can also be produced in hairy roots cultures of Paulownia tomentosa (empress tree, Paulowniaceae). It can also be produced in plant cell cultures of Leucosceptrum sp (Lamiaceae) and Syringa sp (Oleaceae). Verbascoside derivatives can be found in the Verbascum undulatum and notably apiosides in Verbascum sp. Verbascoside can be found in species in all the families of the order Lamiales (syn. Scrophulariales).
Structure
Data?1563862623
Synonyms
ValueSource
KusagininHMDB
VerbascosideHMDB
6-[2-(3,4-Dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoic acidGenerator
ActeosideMeSH
Chemical FormulaC29H36O15
Average Molecular Weight624.5871
Monoisotopic Molecular Weight624.205420482
IUPAC Name6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Traditional Nameverbascoside
CAS Registry Number61276-17-3
SMILES
CC1OC(OC2C(O)C(OCCC3=CC(O)=C(O)C=C3)OC(CO)C2OC(=O)\C=C\C2=CC(O)=C(O)C=C2)C(O)C(O)C1O
InChI Identifier
InChI=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+
InChI KeyFBSKJMQYURKNSU-QPJJXVBHSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentCoumaric acids and derivatives
Alternative Parents
Substituents
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Tyrosol derivative
  • Catechol
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Phenol
  • Monocyclic benzene moiety
  • Fatty acyl
  • Oxane
  • Benzenoid
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Polyol
  • Acetal
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Primary alcohol
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.97 g/LALOGPS
logP1.09ALOGPS
logP0.82ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)9.01ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area245.29 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity148.4 m³·mol⁻¹ChemAxon
Polarizability61.69 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0c01-8920533000-c097428fe1e65a0969d1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00gv-9700035000-c5b8ef4573cf92ca120fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06vi-0610905000-d3e010321fe0d919d876Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08g0-0902400000-dd983ed069c1287efa62Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-07vs-0936300000-3704d6fa7e12bff5166cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-024i-1711907000-8d66cf1f56e75f6558adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ta-1931400000-86ecba3eeab93093ef6cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-2912000000-635e9beb27d765412134Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB013409
KNApSAcK IDC00002783
Chemspider ID4572852
KEGG Compound IDC10501
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkVerbascoside
METLIN IDNot Available
PubChem Compound5459010
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yamada P, Iijima R, Han J, Shigemori H, Yokota S, Isoda H: Inhibitory effect of acteoside isolated from Cistanche tubulosa on chemical mediator release and inflammatory cytokine production by RBL-2H3 and KU812 cells. Planta Med. 2010 Oct;76(14):1512-8. doi: 10.1055/s-0030-1249775. Epub 2010 Mar 30. [PubMed:20354949 ]
  2. Lau CW, Chen ZY, Wong CM, Yao X, He Z, Xu H, Huang Y: Attenuated endothelium-mediated relaxation by acteoside in rat aorta: Role of endothelial [Ca2+]i and nitric oxide/cyclic GMP pathway. Life Sci. 2004 Jul 23;75(10):1149-57. [PubMed:15219803 ]
  3. He ZD, Huang Y, Yao X, Lau CW, Law WI, Chen ZY: Purification of phenylethanoids from Brandisia hancei and the antiproliferative effects on aortic smooth muscle. Planta Med. 2001 Aug;67(6):520-2. [PubMed:11509971 ]
  4. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .