CHEBI:68340 - β-(4-hydroxyphenyl)ethyl-4-O-E-caffeoyl-O-[β-D-apiofuranosyl-(1→2)]-β-D-glucopyranoside

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ChEBI Name β-(4-hydroxyphenyl)ethyl-4-O-E-caffeoyl-O-[β-D-apiofuranosyl-(1→2)]-β-D-glucopyranoside
ChEBI ID CHEBI:68340
ChEBI ASCII Name beta-(4-hydroxyphenyl)ethyl-4-O-E-caffeoyl-O-[beta-D-apiofuranosyl-(1->2)]-beta-D-glucopyranoside
Definition A phenylethanoid that is the 4-O-E-caffeoyl-O-[β-D-apiofuranosyl-(1→2)]-β-D-glucopyranosyl derivative of 4-(2-hydroxyethyl)phenol. Isolated from Lepisorus contortus, it exhibits inhibitory activities against aromatase and NF-κB.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ZINC000066124112
Download Molfile XML SDF
Formula C28H34O14
Net Charge 0
Average Mass 594.56120
Monoisotopic Mass 594.19486
InChI InChI=1S/C28H34O14/c29-12-20-23(41-21(34)8-4-16-3-7-18(32)19(33)11-16)22(35)24(42-27-25(36)28(37,13-30)14-39-27)26(40-20)38-10-9-15-1-5-17(31)6-2-15/h1-8,11,20,22-27,29-33,35-37H,9-10,12-14H2/b8-4+/t20-,22+,23-,24-,25+,26-,27+,28-/m1/s1
InChIKey TXTPNFUSMTWSFE-JCJVHILYSA-N
SMILES [H][C@]1(OC[C@](O)(CO)[C@H]1O)O[C@@H]1[C@@H](O)[C@H](OC(=O)\C=C\c2ccc(O)c(O)c2)[C@@H](CO)O[C@H]1OCCc1ccc(O)cc1
Metabolite of Species Details
Lepisorus contortus (NCBI:txid699669) Found in whole plant (BTO:0001461). 95% EtOH extract of air-dried, powdered whole plant See: PubMed
Roles Classification
Biological Role(s): EC 1.14.14.14 (aromatase) inhibitor
An EC 1.14.14.* (oxidoreductase acting on paired donors, incorporating of 1 atom of oxygen, with reduced flavin or flavoprotein as one donor) inhibitor which interferes with the action of aromatase (EC 1.14.14.14) and so reduces production of estrogenic steroid hormones.
NF-kappaB inhibitor
An inhibitor of NF-kappaB (nuclear factor kappa-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing β-(4-hydroxyphenyl)ethyl-4-O-E-caffeoyl-O-[β-D-apiofuranosyl-(1→2)]-β-D-glucopyranoside (CHEBI:68340) has role EC 1.14.14.14 (aromatase) inhibitor (CHEBI:50790)
β-(4-hydroxyphenyl)ethyl-4-O-E-caffeoyl-O-[β-D-apiofuranosyl-(1→2)]-β-D-glucopyranoside (CHEBI:68340) has role NF-κB inhibitor (CHEBI:73240)
β-(4-hydroxyphenyl)ethyl-4-O-E-caffeoyl-O-[β-D-apiofuranosyl-(1→2)]-β-D-glucopyranoside (CHEBI:68340) has role plant metabolite (CHEBI:76924)
β-(4-hydroxyphenyl)ethyl-4-O-E-caffeoyl-O-[β-D-apiofuranosyl-(1→2)]-β-D-glucopyranoside (CHEBI:68340) is a β-D-glucoside (CHEBI:22798)
β-(4-hydroxyphenyl)ethyl-4-O-E-caffeoyl-O-[β-D-apiofuranosyl-(1→2)]-β-D-glucopyranoside (CHEBI:68340) is a alkyl caffeate ester (CHEBI:65331)
β-(4-hydroxyphenyl)ethyl-4-O-E-caffeoyl-O-[β-D-apiofuranosyl-(1→2)]-β-D-glucopyranoside (CHEBI:68340) is a phenylethanoid (CHEBI:74644)
IUPAC Name
2-(4-hydroxyphenyl)ethyl 2-O-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl]-4-O-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-β-D-glucopyranoside
Citation
Yang JH, Kondratyuk TP, Jermihov KC, Marler LE, Qiu X, Choi Y, Cao H, Yu R, Sturdy M, Huang R, Liu Y, Wang LQ, Mesecar AD, van Breemen RB, Pezzuto JM, Fong HH, Chen YG, Zhang HJ (2011)
Bioactive compounds from the fern Lepisorus contortus.
Journal of natural products 74, 129-136 [PubMed:21261296]
[show Abstract]
Last Modified
25 March 2015