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1. (Article ID: 10851)
Kinjo J, Kishida F, Watanabe K, Hashimoto F, Nohara T
Five new triterpene glycosides from Russell lupine
Chemical and Pharmaceutical Bulletin 42 (1994)
1874-1878
In a continuing study on the ingredients of Lupinus genus, we examined the oligoglycoside constituents of the Russell lupine (L. polyphyllus×L. arboreus hybrid). Five new oleanene glycosides, called Lupinosides PA_<1-5> (1-5), together with three known ones were isolated. Their structures of 1-5 were determined to be 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glactopyranosyl-(1→2)-β-D-glucuronopyranosyl soyasapogenol A 21-O-β-D-xylopyranoside (1), 3-O-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl soyasapogenol A 21-O-β-D-xylopyranoside (2), 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl kudzusapogenol A 21-O-β-D-xylopyranoside (3), 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl soyasapogenol B 22-O-α-L-rhamnopyranoside (4), and 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl soyasapogenol B 22-O-β-D-glucopyranosyl-(1→4)-α-L-rhamnopyranoside (5), respectively.
Leguminosae, oleanene glycoside, lupinoside, Russell lupine, Lupinus polyphyllus x L. arboreus
NCBI PubMed ID: 7954941Publication DOI: 10.1248/cpb.42.1874Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Faculty of Pharmaceutical Sciences, Kumamoto University, Japan
Methods: 13C NMR, 1H NMR, EI-MS, IR, FAB-MS, TLC, acid hydrolysis, HPLC, enzymatic digestion, CC
The publication contains the following compound(s):
- Compound ID: 23677
Structure type: oligomer
Trivial name: soyasaponin I, astrachrysoside A soyasaponin I, soyasaponin 1, saponin Bb soyasaponin I, soyasaponin Bb
Compound class: saponin glycoside, glycoside, triterpenoid glycoside
Reference(s) to other database(s): CCSD:
48360, CBank-STR:9568, PubChem:122097
- Compound ID: 24730
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a-L-Rhap-(1-2)-b-D-Galp-(1-2)-b-D-GlcpA-(1-3)-Subst
Subst = olean-12-en-3β,23-diol-22-one = SMILES C[C@]({23}CO)([C@](CC[C@@]([C@](CC[C@@]12C)3C)4C)5[H]){3}[C@@H](O)CC[C@]5(C)[C@@]4([H])CC=C3[C@]2([H])CC(C)(C)CC1=O |
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Structure type: oligomer
Trivial name: dehydrosoyasaponin I
Compound class: saponin glycoside, glycoside
Reference(s) to other database(s): CCSD:
17898, CBank-STR:9575
- Compound ID: 27000
|
b-D-Xylp-(1-21)-+
|
a-L-Rhap-(1-2)-b-D-Galp-(1-2)-b-D-GlcpA-(1-3)-SoyasapogenolA |
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Structure type: oligomer
; 1089 [M-H]-
C53H86O23
Trivial name: lupinoside PA1
Compound class: glycoside
Reference(s) to other database(s): CCSD:
46100, CBank-STR:12206
- Compound ID: 27001
|
a-L-Rhap-(1-2)-b-D-Galp-(1-2)-b-D-GlcpA-(1-3)-Subst
Subst = kudzusapogenol A = SMILES C[C@]1({24}CO){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])C[C@](C)({29}CO){21}[C@@H](O){22}[C@@H](O)[C@@](C)5CC[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
Trivial name: kudzusaponin A3
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 27002
Structure type: monomer
Compound class: glycoside
- Compound ID: 27003
Structure type: monomer
Compound class: glycoside
- Compound ID: 27004
|
b-D-Xylp-(1-21)-+
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b-D-Galp-(1-2)-b-D-GlcpA-(1-3)-SoyasapogenolA |
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Structure type: oligomer
; 943 [M-H]-
C47H76O19
Trivial name: lupinoside PA2
Compound class: glycoside
Reference(s) to other database(s): CCSD:
46101, CBank-STR:8779
- Compound ID: 27005
|
b-D-Xylp-(1-21)-+
|
a-L-Rhap-(1-2)-b-D-Galp-(1-2)-b-D-GlcpA-(1-3)-Subst
Subst = kudzusapogenol A = SMILES C[C@]1({24}CO){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])C[C@](C)({29}CO){21}[C@@H](O){22}[C@@H](O)[C@@](C)5CC[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
; 1105 [M-H]-
C53H86O24
Trivial name: lupinoside PA3
Compound class: glycoside
Reference(s) to other database(s): CCSD:
46102, CBank-STR:12207
- Compound ID: 27006
|
a-L-Rhap-(1-22)-+
|
a-L-Rhap-(1-2)-b-D-Galp-(1-2)-b-D-GlcpA-(1-3)-SoyasapogenolB |
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Structure type: oligomer
; 1087 [M-H]-
C54H89O22
Trivial name: lupinoside PA4
Compound class: glycoside
Reference(s) to other database(s): CCSD:
46103, CBank-STR:12032
- Compound ID: 27007
|
b-D-Glcp-(1-4)-a-L-Rhap-(1-22)-+
|
a-L-Rhap-(1-2)-b-D-Galp-(1-2)-b-D-GlcpA-(1-3)-SoyasapogenolB |
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Structure type: oligomer
; 1249 [M-H]-
C60H98O27
Trivial name: lupinoside PA5
Compound class: glycoside
Reference(s) to other database(s): CCSD:
46104, CBank-STR:14595
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