3beta-O-{alpha-L-Rhap-(1->2)-beta-D-Glcp-(1->4)-[beta-D-Glcp-(1->2)]-alpha-L-Arap}primulagenin A (CHEBI:65424)

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CHEBI:65424 - 3β-O-{α-L-Rhap-(1→2)-β-D-Glcp-(1→4)-[β-D-Glcp-(1→2)]-α-L-Arap}primulagenin A

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ChEBI ID	CHEBI:65424
ChEBI Name	3β-O-{α-L-Rhap-(1→2)-β-D-Glcp-(1→4)-[β-D-Glcp-(1→2)]-α-L-Arap}primulagenin A
Stars
ASCII Name	3beta-O-{alpha-L-Rhap-(1->2)-beta-D-Glcp-(1->4)-[beta-D-Glcp-(1->2)]-alpha-L-Arap}primulagenin A
Definition	A triterpenoid saponin that is composed of primulagenin A having a α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→2)]-α-L-arabinopyranosyl moiety attached to position 3 by a glycosidic linkage. It is isolated from the whole plants of Ardisia pusilla and exhibits cytotoxic activity against human gliboblastoma U251MG cells.
Last Modified	20 January 2014
Downloads	Molfile

Formula	C53H88O21
Net Charge	0
Average Mass	1061.266
Monoisotopic Mass	1060.58181
SMILES	[H][C@@]1(O[C@@H]2[C@@H](O)[C@@]([H])(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@]3([H])O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)CO[C@@]2([H])O[C@H]2CC[C@]3(C)[C@@]4([H])CC=C5[C@]6([H])CC(C)(C)CC[C@]6(CO)[C@H](O)C[C@@]5(C)[C@]4(C)CC[C@@]3([H])C2(C)C)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChI	InChI=1S/C53H88O21/c1-23-33(58)37(62)40(65)44(68-23)74-43-39(64)35(60)27(20-55)70-47(43)71-28-21-67-46(42(36(28)61)73-45-41(66)38(63)34(59)26(19-54)69-45)72-32-12-13-50(6)29(49(32,4)5)11-14-51(7)30(50)10-9-24-25-17-48(2,3)15-16-53(25,22-56)31(57)18-52(24,51)8/h9,23,25-47,54-66H,10-22H2,1-8H3/t23-,25-,26+,27+,28-,29-,30+,31+,32-,33-,34+,35+,36-,37+,38-,39-,40+,41+,42+,43+,44-,45-,46-,47-,50-,51+,52+,53+/m0/s1
InChIKey	KNJZSRUBTKLEDR-FXRKFYLMSA-N

Species of Metabolite	Component	Source	Comments
Ardisia pusilla (ncbitaxon:587403)	whole plant (BTO:0001461)	PubMed (19039733)
Lysimachia clethroides (ncbitaxon:167892)	aerial part (BTO:0001658)	PubMed (21928797)	Air-dried, powdered aerial parts were extracted with 70% aqueous ethyl alcohol.

Roles Classification

Biological Roles:	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.
Application:	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology

Outgoing Relation(s)
	3β-O-{α-L-Rhap-(1→2)-β-D-Glcp-(1→4)-[β-D-Glcp-(1→2)]-α-L-Arap}primulagenin A (CHEBI:65424) has functional parent primulagenin A (CHEBI:70978)
	3β-O-{α-L-Rhap-(1→2)-β-D-Glcp-(1→4)-[β-D-Glcp-(1→2)]-α-L-Arap}primulagenin A (CHEBI:65424) has role antineoplastic agent (CHEBI:35610)
	3β-O-{α-L-Rhap-(1→2)-β-D-Glcp-(1→4)-[β-D-Glcp-(1→2)]-α-L-Arap}primulagenin A (CHEBI:65424) has role plant metabolite (CHEBI:76924)
	3β-O-{α-L-Rhap-(1→2)-β-D-Glcp-(1→4)-[β-D-Glcp-(1→2)]-α-L-Arap}primulagenin A (CHEBI:65424) is a pentacyclic triterpenoid (CHEBI:25872)
	3β-O-{α-L-Rhap-(1→2)-β-D-Glcp-(1→4)-[β-D-Glcp-(1→2)]-α-L-Arap}primulagenin A (CHEBI:65424) is a tetrasaccharide derivative (CHEBI:63567)
	3β-O-{α-L-Rhap-(1→2)-β-D-Glcp-(1→4)-[β-D-Glcp-(1→2)]-α-L-Arap}primulagenin A (CHEBI:65424) is a triterpenoid saponin (CHEBI:61778)

IUPAC Name
(3β,16α)-16,28-dihydroxyolean-12-en-3-yl 6-deoxy-α-L-mannopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→2)]-α-L-arabinopyranoside

Synonyms	Source
3β-O-{α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→2)]-α-L-arabinopyranosyl}-16α,28-dihydroxy-olean-12-ene	ChEBI
3β-O-{α-L-Rhap-(1→2)-β-D-Glcp-(1→4)-[β-D-Glcp-(1→2)]-α-L-Arap}-16α,28-dihydroxyolean-12-ene	ChEBI
3β-O-{α-L-Rhap-(1→2)-β-D-Glcp-(1→4)-[β-D-Glcp-(1→2)]-α-L-Arap}-primulagenin A	ChEBI
Ardisia saponin	ChEBI

Registry Numbers	Sources
Reaxys:22007805	Reaxys

Citations