3-O-[beta-D-glucopyranosyl]-28-O-[alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranosyl]arjunolic acid (CHEBI:68378)

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CHEBI:68378 - 3-O-[β-D-glucopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl]arjunolic acid

ChEBI ID	CHEBI:68378
ChEBI Name	3-O-[β-D-glucopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl]arjunolic acid
Stars
ASCII Name	3-O-[beta-D-glucopyranosyl]-28-O-[alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranosyl]arjunolic acid
Definition	A triterpenoid saponin that is arjunolic acid attached to a β-D-glucopyranosyl residue at position 3 and a α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl residue at position 28. Isolated from the methanolic extract of the leaves of Symplocos lancifolia, it exhibits antibacterial activity.
Last Modified	20 January 2014
Downloads	Molfile

Formula	C48H78O19
Net Charge	0
Average Mass	959.133
Monoisotopic Mass	958.51373
SMILES	[H][C@@]1(O[C@H]2[C@H](OC(=O)[C@]34CCC(C)(C)C[C@@]3([H])C3=CC[C@]5([H])[C@@]6(C)C[C@@H](O)[C@H](O[C@]7([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@@](C)(CO)[C@]6([H])CC[C@@]5(C)[C@]3(C)CC4)O[C@H](CO)[C@@H](O)[C@@H]2O)O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O
InChI	InChI=1S/C48H78O19/c1-21-29(53)32(56)35(59)39(62-21)65-37-34(58)31(55)26(19-50)64-41(37)67-42(61)48-14-12-43(2,3)16-23(48)22-8-9-28-44(4)17-24(52)38(66-40-36(60)33(57)30(54)25(18-49)63-40)45(5,20-51)27(44)10-11-47(28,7)46(22,6)13-15-48/h8,21,23-41,49-60H,9-20H2,1-7H3/t21-,23-,24+,25+,26+,27+,28+,29-,30+,31+,32+,33-,34-,35+,36+,37+,38-,39-,40-,41-,44-,45-,46+,47+,48-/m0/s1
InChIKey	IYMDTUUDLAHXGD-HADMNRPSSA-N

Species of Metabolite	Component	Source	Comments
Symplocos lancifolia (ncbitaxon:239704)	leaf (BTO:0000713)	PubMed (21288041)	Dried, powdered leaves extracted with boiling 80% methanol

Roles Classification

Biological Roles:

antibacterial agent A substance (or active part thereof) that kills or slows the growth of bacteria.

plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.

metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.

ChEBI Ontology

Outgoing Relation(s)
	3-O-[β-D-glucopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl]arjunolic acid (CHEBI:68378) has functional parent arjunolic acid (CHEBI:68381)
	3-O-[β-D-glucopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl]arjunolic acid (CHEBI:68378) has role antibacterial agent (CHEBI:33282)
	3-O-[β-D-glucopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl]arjunolic acid (CHEBI:68378) has role plant metabolite (CHEBI:76924)
	3-O-[β-D-glucopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl]arjunolic acid (CHEBI:68378) is a pentacyclic triterpenoid (CHEBI:25872)
	3-O-[β-D-glucopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl]arjunolic acid (CHEBI:68378) is a triterpenoid saponin (CHEBI:61778)

IUPAC Name
2-O-(6-deoxy-α-L-mannopyranosyl)-1-O-[(2α,3β)-3-(β-D-glucopyranosyloxy)-2,23-dihydroxy-28-oxoolean-12-en-28-yl]-β-D-glucopyranose

Registry Numbers	Sources
Reaxys:21306693	Reaxys

Citations