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1. (Article ID: 9774)
Miyamura M, Nakano K, Nohara T, Tomimatsu T, Kawasaki T
Steroid saponins from Paris polyphylla Sm.-supplement
Chemical and Pharmaceutical Bulletin 30(2) (1982)
712-718
Previously, four steroid glycosides (Pa-d) were isolated from the rhizomes of Paris polyphylla SM. and characterized. In a continuation of our studies on this plant, a further five new steroid glycosides (1,2,12,14 and 16) together with three known compounds (13,18 and 19; the latter two have been obtained synthetically as acetyl derivatives) have been isolated and their structures established as follows. 1 and 2: (22ξ,25R)-22-methoxyfurostanol 3,26-O-bisglycosides (proto-type saponins) corresponding to Pa [diosgein 3-O-α-L-ara*fur-(1→4)-[α-L-rha*pyr-(1→2)]-β-D-glc*pyranoside (3)] and Pb [diosgein 3-O-α-L-rha*pyr-(1→4)-α-L-rha*pyr-(1→4)-[α-L-rha*pyr-(1→2)]-β-D-glc*pyranoside (6)], respectively; 12 and 13: pennogenin oligosides having the same sugar moieties as 3 and 6, respectively; 14 and 18: pennogenin derivatives carrying 3-O-α-L-ara*fur-(1→4)-β-D-glc*pyranoside and hexaacetyl 3-O-α-L-rha*pyr-(1→2)-β-D-glc・pyranoside, respectively; 16 and 19: diosgenin derivatives carrying the same sugar moieties as 14 and 18, respectively.
Liliaceae, Paris polyphylla, furostanol glycoside, diosgenin glycoside, pennogenin glycoside, arabinofuranoside
Publication DOI: 10.1248/cpb.30.712Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003634336Publisher: Pharmaceutical Society Of Japan
Institutions: Faculty of Pharmaceutical Sciences, Tokushima University, Tokushima, Japan, Faculty of Pharmaceutical Sciences, Kyushu University, Fukuoka, Japan
Methods: 13C NMR, 1H NMR, IR, TLC, GLC, MS, methanolysis, UV, enzymatic digestion, methylation analysis, melting point determination, PPC, acetylation analysis
The publication contains the following compound(s):
- Compound ID: 23732
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a-L-Rhap-(1-2)-+
|
a-L-Rhap-(1-4)-a-L-Rhap-(1-4)-b-D-Glcp-(1-3)-Subst
Subst = pennogenin = SMILES C[C@@H]1CC[C@@]2([C@H]({17}[C@]3([C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC=C6[C@@]5(CC{3}[C@@H](C6)O)C)C)O)C)OC1 |
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Structure type: oligomer
Trivial name: Tg
Compound class: saponin glycoside, triterpenoid glycoside
Reference(s) to other database(s): CCSD:
17921, CBank-STR:9345
- Compound ID: 23733
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a-L-Rhap-(1-2)-+
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a-L-Rhap-(1-4)-a-L-Rhap-(1-4)-b-D-Glcp-(1-3)-Diosgenin |
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Structure type: oligomer
Trivial name: Pb
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
20252, CBank-STR:9343
- Compound ID: 23802
Structure type: oligomer
Trivial name: diosgenin, polyphyllin D
Compound class: saponin glycoside, triterpenoid glycoside
Reference(s) to other database(s): CCSD:
23222, CBank-STR:6171
- Compound ID: 23803
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b-D-Glcp-(1-26)-+
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a-L-Araf-(1-4)-+ |
| |
a-L-Rhap-(1-2)-b-D-Glcp-(1-3)-Subst22Me
Subst = 25R-furost-5-en-3β,22,26-triol = SMILES C[C@H]1[C@H]2[C@H](C[C@@H]3[C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4(CC{3}[C@@H](C5)O)C)C)O{22}C1(CC[C@@H](C){26}[CH2]O)O |
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Structure type: oligomer
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
26977, CBank-STR:9912
- Compound ID: 23804
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b-D-Glcp-(1-26)-+
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a-L-Rhap-(1-2)-+ |
| |
a-L-Rhap-(1-4)-a-L-Rhap-(1-4)-b-D-Glcp-(1-3)-Subst22Me
Subst = 25R-furost-5-en-3β,22,26-triol = SMILES C[C@H]1[C@H]2[C@H](C[C@@H]3[C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4(CC{3}[C@@H](C5)O)C)C)O{22}C1(CC[C@@H](C){26}[CH2]O)O |
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Structure type: oligomer
Trivial name: methyl-proto-Pb, methyl proto-Pb
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
20247, CBank-STR:11972
- Compound ID: 23805
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a-L-Arap-(1-4)-b-D-Glcp-(1-3)-Subst
Subst = pennogenin = SMILES C[C@@H]1CC[C@@]2([C@H]({17}[C@]3([C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC=C6[C@@]5(CC{3}[C@@H](C6)O)C)C)O)C)OC1 |
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Structure type: oligomer
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
26980, CBank-STR:3214
- Compound ID: 23806
Structure type: oligomer
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
26981, CBank-STR:3210
- Compound ID: 23807
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a-L-Rhap2Ac3Ac4Ac-(1-2)-b-D-Glcp3Ac4Ac6Ac-(1-3)-Subst
Subst = pennogenin = SMILES C[C@@H]1CC[C@@]2([C@H]({17}[C@]3([C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC=C6[C@@]5(CC{3}[C@@H](C6)O)C)C)O)C)OC1 |
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Structure type: oligomer
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
26982, CBank-STR:3462
- Compound ID: 23808
Structure type: oligomer
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
26983, CBank-STR:3461
- Compound ID: 23809
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a-L-Araf-(1-4)-+
|
a-L-Rhap-(1-2)-b-D-Glcp-(1-3)-Subst
Subst = pennogenin = SMILES C[C@@H]1CC[C@@]2([C@H]({17}[C@]3([C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC=C6[C@@]5(CC{3}[C@@H](C6)O)C)C)O)C)OC1 |
Show graphically |
Structure type: oligomer
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
17761, CBank-STR:6173
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