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Taxonomic group: plant / Streptophyta (Phylum: Streptophyta)
Organ / tissue: leaf

The structure was elucidated in this paper
Journal NLM ID: 0377775
WWW link: http://ci.nii.ac.jp/naid/110003633966
Publisher: Pharmaceutical Society Of Japan
Institutions: Faculty of Pharmaceutical Sciences, Nagoya City University, Nagoya, Japan

Two new triglycosides of oleanane-type triterpenes, rotundioside E (3) and F (1), isolated from the leaves of Bupleurum rotundifolium L. were identified as 16α,28-dihydroxyoleana-11,13(18)-dien-3β-yl α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-fucopyranoside (3) and 13β,28-epoxy-16α-hydroxyoleana-11-en-3β-yl α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-fucopyranoside (1), respectively, on the basis of chemical and spectroscopic evidence.

oleanane triterpenoid glycoside, Bupleurum rotundifolium L., Umbelliferae, rotundioside E, rotundioside F, CMR spectrum, Smith-de Mayo degradation

Structure type: oligomer
Location inside paper: chart 1, structure 1
Trivial name: rotundioside F
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_142489,IEDB_146664,IEDB_149135,IEDB_225177,IEDB_885823,IEDB_983931,SB_192,SB_86

Methods: IR, TLC, acid hydrolysis, MS, methylation analysis, melting point determination, PMR, acetylation analysis, CMR, Smith-de Mayo degradation

NCBI Taxonomy refs (TaxIDs): 90446
Reference(s) to other database(s): CCSD:15440, CBank-STR:7615
Show glycosyltransferases

NMR conditions: in C5D5N [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
3,2,2	aLRhap	102.5	72.9	72.9	74.7	69.9	18.7
3,2	bDGlcp	102.3	79.8	77.7	72.9	77.7	63.7
3	bDFucp	105.7	78.4	76.6	72.9	71.2	17.8
	Subst


1H NMR data:
missing...

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
3,2,2	aLRhap	102.5	72.9	72.9	74.7	69.9	18.7
3,2	bDGlcp	102.3	79.8	77.7	72.9	77.7	63.7
3	bDFucp	105.7	78.4	76.6	72.9	71.2	17.8
	Subst

There is only one chemically distinct structure:

C[C@@H]1O[C@@H](O[C@H]2[C@H](O[C@@H]3[C@@H](O)[C@@H](O)[C@@H](C)O[C@H]3O[C@H]3CC[C@@]4(C)[C@@H](CC[C@]5(C)[C@@H]4C=C[C@]46OC[C@@]7(CCC(C)(C)C[C@H]74)[C@H](O)C[C@]65C)C3(C)C)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O

SVG MW SMILES 3D mol Ionize

oleanane triterpenoid glycoside, Bupleurum rotundifolium L., Umbelliferae, rotundioside E, rotundioside F, CMR spectrum, Smith-de Mayo degradation

Structure type: oligomer
Location inside paper: chart 1, 3
Trivial name: rotundioside E
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_142489,IEDB_146664,IEDB_149135,IEDB_225177,IEDB_885823,IEDB_983931,SB_192,SB_86

Methods: IR, TLC, acid hydrolysis, MS, methylation analysis, melting point determination, PMR, acetylation analysis, CMR, Smith-de Mayo degradation
Comments, role: rotundiogenin B = 16-epi-saikogenin C

NCBI Taxonomy refs (TaxIDs): 90446
Reference(s) to other database(s): CCSD:15440, CBank-STR:7615
Show glycosyltransferases

NMR conditions: in C5D5N [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
3,2,2	aLRhap	102.2	72.8	72.8	74.3	69.5	18.7
3,2	bDGlcp	101.8	79.5	77.2	72.8	77.2	63.3
3	bDFucp	105.3	78.0	76.2	72.8	70.9	17.4
	Subst


1H NMR data:
missing...

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
3,2,2	aLRhap	102.2	72.8	72.8	74.3	69.5	18.7
3,2	bDGlcp	101.8	79.5	77.2	72.8	77.2	63.3
3	bDFucp	105.3	78.0	76.2	72.8	70.9	17.4
	Subst

There is only one chemically distinct structure:

C[C@@H]1O[C@@H](O[C@H]2[C@H](O[C@@H]3[C@@H](O)[C@@H](O)[C@@H](C)O[C@H]3O[C@H]3CC[C@@]4(C)[C@@H](CC[C@]5(C)[C@@H]4C=CC4=C6CC(C)(C)CC[C@]6(CO)[C@H](O)C[C@]45C)C3(C)C)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O

SVG MW SMILES 3D mol Ionize