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1. (Article ID: 9766)
Konishi T, Shoji J
Studies on the constituents of asparagi radix. I. On the structures of furostanol oligosides of Asparagus cochinchinensis (Loureio) Merrill
Chemical and Pharmaceutical Bulletin 27(12) (1979)
3086-3094
Asp-IV, V, VI and VII, the major furostanol oligosides, have been isolated from the methanol extract of Asparagus cochinchinensis (LOUREIO) MERRILL (Liliaceae). The structures of Asp-IV, V, VI and VII have been established as 26-O-β-D-glucopyranosyl-22-methoxyfurostane-3β,26-diol 3-O-β-D-xylopyranosyl(1→4)-β-D-glucopyranoside (1), 26-O-β-D-glucopyranosyl-22-methoxyfurostane-3β,26-diol 3-O-α-L-rhamnopyranosyl(1→6)-β-D-glucopyranoside (2), 26-O-β-D-glucopyranosyl-22-methoxyfurostane-3β,26-diol 3-O-β-D-xylopyranosyl(1→4)-[α-L-rhamnopyranosyl(1→6)]-β-D-glucopyranoside (3) and 26-O-β-D-glucopyranosyl-22-methoxyfurostane-3β,26-diol 3-O-[β-D-glucopyranosyl(1→2)] [β-D-xylopyranosyl(1→4)] [α-L-rhamnopyranosyl(1→6)]-β-D-glucopyranoside (4), respectively. Amethoxyl group at C-22 of each furostanol oligoside is converted to a hydroxyl group by boiling in aqueous acetone. The interconversions between methoxyl and hydroxyl groups at C-22 of the furostanol oligosides were investigated and the genuine furostanol oligosides of Asparagi radix appear to be of the hydroxyl type, based on comparative studies of the methanol and pyridine extracts.
13C NMR, Liliaceae, Asparagi radix, Asparagus cochinchinensis, furostanol oligoside, steroidal saponin, sarsasapogenin
Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003623577Publisher: Pharmaceutical Society Of Japan
Institutions: School of Pharmaceutical Sciences, Showa University, Japan
Methods: 13C NMR, IR, partial acid hydrolysis, acid hydrolysis, GLC, MS, methanolysis, enzymatic digestion, methylation analysis, PMR
The publication contains the following compound(s):
- Compound ID: 23783
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b-D-Glcp-(1-15)-+
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a-L-Rhap-(1-6)-b-D-Glcp-(1-3)-Subst
Subst = 15-hydroxysarsasapogenin = SMILES [H][C@]1(O[C@@]2(OC[C@@H](C)CC2)[C@H]3C){15}[C@H](O)[C@@]4([H])[C@]5([H])CC[C@]6([H])C{3}[C@@H](O)CC[C@]6(C)[C@@]5([H])CC[C@]4(C)[C@]13[H] |
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Structure type: oligomer
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
10353, CBank-STR:6752
- Compound ID: 23784
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b-D-Glcp-(1-26)-+
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b-D-Xylp-(1-4)-b-D-Glcp-(1-3)-Subst22Me
Subst = 25S-5β-furostan-3β,22,26-triol = SMILES C[C@H]1[C@H]2[C@@H](O{22}C1(O)CC[C@@H]({26}[CH2]O)C)C[C@@H]3[C@]2(C)CC[C@H]4[C@H]3CC[C@H]5[C@]4(C)CC{3}[C@H](O)C5 |
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Structure type: oligomer
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
10354, CBank-STR:7434
- Compound ID: 23785
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b-D-Glcp-(1-15)-+
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a-L-Rhap-(1-6)-+ |
| |
b-D-Xylp-(1-4)-b-D-Glcp-(1-3)-Subst
Subst = 15-hydroxysarsasapogenin = SMILES [H][C@]1(O[C@@]2(OC[C@@H](C)CC2)[C@H]3C){15}[C@H](O)[C@@]4([H])[C@]5([H])CC[C@]6([H])C{3}[C@@H](O)CC[C@]6(C)[C@@]5([H])CC[C@]4(C)[C@]13[H] |
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Structure type: oligomer
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
10355, CBank-STR:10676
- Compound ID: 23786
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b-D-Glcp-(1-15)-+
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b-D-Xylp-(1-4)-+ |
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b-D-Glcp-(1-2)-b-D-Glcp-(1-3)-Subst
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a-L-Rhap-(1-6)-+
Subst = 15-hydroxysarsasapogenin = SMILES [H][C@]1(O[C@@]2(OC[C@@H](C)CC2)[C@H]3C){15}[C@H](O)[C@@]4([H])[C@]5([H])CC[C@]6([H])C{3}[C@@H](O)CC[C@]6(C)[C@@]5([H])CC[C@]4(C)[C@]13[H] |
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Structure type: oligomer
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
10356, CBank-STR:13081
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2. (Article ID: 10134)
Liang Z, Aquino R, De Simone F, Dini A, Schettino O, Pizza C
Oligofurostanosides from Asparagus cochinchinensis
Planta Medica 54 (1988)
344-346
The aqueous extract of ASPARAGUS COCHINCHINENSIS yielded a new oligofurostanoside 3- O-[α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl]-26- O-(β-D-glucopyranosyl)-(25 R)-furosta-5,20-diene,-3β,26-diol as well as two known furostanosides, methylprotodioscin and pseudoprotodioscin.
NCBI PubMed ID: 17265283Publication DOI: 10.1055/s-2006-962453Journal NLM ID: 0066751Publisher: George Thieme
Institutions: Shanghai Institute of Pharmaceutical Industry, Shanghai, China
The publication contains the following compound(s):
- Compound ID: 23826
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b-D-Glcp-(1-26)-+
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a-L-Rhap-(1-4)-+ |
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a-L-Rhap-(1-2)-b-D-Glcp-(1-3)-Subst22Me
Subst = 25R-furost-5-en-3β,22α,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}[C@@]1(CC[C@@H](C){26}[CH2]O)O |
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Structure type: oligomer
Trivial name: methyl-proto-dioscin, polyphyllin D, methyl protodioscin
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
27804, CBank-STR:6380
- Compound ID: 24415
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b-D-Glcp-(1-26)-+
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a-L-Rhap-(1-4)-+ |
| |
a-L-Rhap-(1-2)-b-D-Glcp-(1-3)-Subst
Subst = 25R-furost-5,20(22)-dien-3β,26-diol = SMILES [H][C@]1(OC(CC[C@@H](C){26}[CH2]O)=C2C)C[C@@]3([H])[C@]4([H])CC=C5C{3}[C@@H](O)CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@]12[H] |
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Structure type: oligomer
Trivial name: pseudoproto-dioscin, pesudoprotodioscin
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
17631, CBank-STR:10005
- Compound ID: 24705
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b-D-Glcp-(1-26)-+
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a-L-Rhap-(1-4)-b-D-Glcp-(1-3)-Subst
Subst = 25R-furost-5,20(22)-dien-3β,26-diol = SMILES [H][C@]1(OC(CC[C@@H](C){26}[CH2]O)=C2C)C[C@@]3([H])[C@]4([H])CC=C5C{3}[C@@H](O)CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@]12[H] |
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Structure type: oligomer
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
28097, CBank-STR:6766
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