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1. (Article ID: 9941)
Saito S, Sumita S, Tamura N, Nagamura Y, Nishida K, Ito M, Ishiguro I
Saponins from the leaves of Aralia elata SEEM. (Araliaceae)
Chemical and Pharmaceutical Bulletin 38 (1990)
411-414
Eleven triterpenoidal saponins having oleanolic acid or hederagenin as the aglycone and two flavonoidal glycosides were isolated from the leaves of Aralia elata SEEM. (Araliaceae). The structures of four new saponins (1,2,3,and 4) were established to be 3-O-α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranosyl-hederagenin 28-O-β-D-xylopyranosyl-(1→6)-β-D-glucopyranosyl ester, 3-O-α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranosyl-oleanolic acid 28-O-β-D-xylopyranosyl(1→6)-β-D-glucopyranosyl ester, 3-O-β-D-glucopyranosyl(1→3)-α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranosyl-hederagenin 28-O-β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl ester, and 3-O-β-D-glucopyranosyl(1→3)-α-L-rhamnopyranosyl(1→2)-α-L arabinopyranosyl-hederagenin, respectively, on the basis of spectroscopic and chemical evidence.
araliaceae, bisdesmoside, oleanolic acid glycoside, hederagenin glycoside, Aralia elata, triterpenoidal saponin, monodesmoside
Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/lognavi?name=nels&lang=en&type=pdf&id=ART0004135125Publisher: Pharmaceutical Society Of Japan
Institutions: Faculty of Pharmaceutical Sciences, Josai University:Fujita Gakuen Health University, Japan, School of Medicine:Fujita Gakuen Health University, Japan, Department of Chemistry, School of Dentistry, Meikai University:Fujita Gakuen Health University, Japan, School of Hygiene:Fujita Gakuen Health University, Japan
Methods: 13C NMR, 1H NMR, IR, FAB-MS, acid hydrolysis, HPLC, alkaline hydrolysis
The publication contains the following compound(s):
- Compound ID: 23949
|
a-L-Rhap-(1-2)-a-L-Arap-(1-3)-+
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a-L-Rhap-(1-4)-b-D-Glcp-(1-6)-b-D-Glcp-(1-28)-Hederagenin |
Show graphically |
Structure type: oligomer
C59H96O26
Trivial name: Kizutasaponin, Kalopanax-saponin B, kalopanax-saponin B, kalopanaxsaponin B, Kizutasaponin K12, hederasaponin C
Compound class: saponin glycoside, glycoside, triterpenoid glycoside
Reference(s) to other database(s): CCSD:
5523, CBank-STR:11737
- Compound ID: 23964
Structure type: oligomer
C41H66O12
Trivial name: Kalopanax-saponin A, α-hederin, kalopanaxsaponin A
Compound class: saponin glycoside, glycoside, triterpenoid glycoside
Reference(s) to other database(s): CCSD:
39886, CBank-STR:2464
- Compound ID: 24164
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a-L-Rhap-(1-2)-a-L-Arap-(1-3)-+
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b-D-Glcp-(1-6)-b-D-Glcp-(1-28)-Oleanolic
Oleanolic = 3β-hydroxyolean-12-en-28-oic acid |
Show graphically |
Structure type: oligomer
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
32234, CBank-STR:9017
- Compound ID: 24165
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a-L-Rhap-(1-2)-a-L-Arap-(1-3)-+
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b-D-Glcp-(1-6)-b-D-Glcp-(1-28)-Hederagenin |
Show graphically |
Structure type: oligomer
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
32236, CBank-STR:9019
- Compound ID: 24166
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b-D-Glcp-(1-6)-b-D-Glcp-(1-28)-+
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b-D-Glcp-(1-3)-a-L-Rhap-(1-2)-a-L-Arap-(1-3)-Oleanolic
Oleanolic = 3β-hydroxyolean-12-en-28-oic acid |
Show graphically |
Structure type: oligomer
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
32237, CBank-STR:12501
- Compound ID: 24167
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a-L-Rhap-(1-2)-a-L-Arap-(1-3)-Oleanolic
Oleanolic = 3β-hydroxyolean-12-en-28-oic acid |
Show graphically |
Structure type: oligomer
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
32229, CBank-STR:2462
- Compound ID: 24168
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b-D-Glcp-(1-3)-a-L-Rhap-(1-2)-a-L-Arap-(1-3)-Oleanolic
Oleanolic = 3β-hydroxyolean-12-en-28-oic acid |
Show graphically |
Structure type: oligomer
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
32231, CBank-STR:6398
- Compound ID: 24169
Structure type: oligomer
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
1365, CBank-STR:2244
- Compound ID: 24170
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a-L-Rhap-(1-2)-a-L-Arap-(1-3)-+
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b-D-Xylp-(1-6)-b-D-Glcp-(1-28)-Hederagenin |
Show graphically |
Structure type: oligomer
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
32235, CBank-STR:8977
- Compound ID: 24171
|
a-L-Rhap-(1-2)-a-L-Arap-(1-3)-+
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b-D-Xylp-(1-6)-b-D-Glcp-(1-28)-Oleanolic
Oleanolic = 3β-hydroxyolean-12-en-28-oic acid |
Show graphically |
Structure type: oligomer
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
32233, CBank-STR:8976
- Compound ID: 24172
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b-D-Glcp-(1-6)-b-D-Glcp-(1-28)-+
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b-D-Glcp-(1-3)-a-L-Rhap-(1-2)-a-L-Arap-(1-3)-Hederagenin |
Show graphically |
Structure type: oligomer
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
32239, CBank-STR:12503
- Compound ID: 24173
Structure type: oligomer
Compound class: saponin glycoside, glycoside, triterpenoid glycoside
Reference(s) to other database(s): CCSD:
32232, CBank-STR:6400
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2. (Article ID: 10059)
Yashikawa M, Murakami T, Yamahara J, Matsuda H
Bioactive saponins and glycosides. XII. horse chestnut. (2): structures of escins IIIb, IV, V, and VI and isoescins Ia, Ib, and V, acylated polyhydroxyoleanene triterpene oligoglycisides, from the seeds of horse chestnut tree (Aesculus hippocastanum L., Hippocastanaceae)
Chemical and Pharmaceutical Bulletin 46(11) (1998)
1764-1769
New acylated polyhydroxyoleanene triterpene oligoglycosides, escins IIIb, IV, V, and VI and isoescins Ia, Ib, and V, were isolated from the seeds of horse chestnut tree (Aesculus hippocastanum L.). Their structures were elucidated on the basis of chemical and physicochemical evidence.
saponin, horse chestnut, Aesculus hippocastanum, escin, isoescin, Hippocastanaceae
NCBI PubMed ID: 9845957Publication DOI: 10.1248/cpb.46.1764Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Kyoto Pharmaceutical University, Kyoto, Japan
Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, acid hydrolysis, alkaline hydrolysis, extraction, optical rotation measurement, HPTLC, CC, melting point determination, HMBC, HR-FAB-MS, reverse-phase silica gel CC, acid treatment
The publication contains the following compound(s):
- Compound ID: 24327
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Tig-(1-21)-+
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b-D-Glcp-(1-4)-+ |
| |
b-D-Glcp-(1-2)-b-D-GlcpA-(1-3)-Subst22Ac
Subst = protoaescigenin = SMILES C[C@]12CC{3}[C@H](O)[C@](C)({24}CO)C1CC[C@]3(C)C2CC=C4[C@@]3(C)C{16}[C@@H](O)[C@]5({28}CO)[C@H]4CC(C)(C){21}[C@@H](O){22}[C@@H]5O;
Tig = (E)-2-methylbut-2-enoic (tiglic) acid |
Show graphically |
Structure type: oligomer
C55H86O24
Trivial name: escin Ia
Compound class: triterpene saponin
Reference(s) to other database(s): CCSD:
14986, CBank-STR:6250
- Compound ID: 24328
|
b-D-Glcp-(1-4)-+
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b-D-Glcp-(1-2)-b-D-GlcpA-(1-3)-Subst
Subst = protoaescigenin = SMILES C[C@]12CC{3}[C@H](O)[C@](C)({24}CO)C1CC[C@]3(C)C2CC=C4[C@@]3(C)C{16}[C@@H](O)[C@]5({28}CO)[C@H]4CC(C)(C){21}[C@@H](O){22}[C@@H]5O |
Show graphically |
Structure type: oligomer
Trivial name: desacylescin I, aesculuside A, desacylescin-I
Compound class: saponin glycoside, sulfoglycolipid (SGL), triterpenoid glycoside, triterpene saponin
Reference(s) to other database(s): CCSD:
36733, CBank-STR:7837
- Compound ID: 24330
|
b-D-Glcp-(1-4)-+
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b-D-Galp-(1-2)-b-D-GlcpA-(1-3)-Subst
Subst = barringtogenol C = SMILES C[C@]12CC{3}[C@H](O)C(C)(C)C1CC[C@]3(C)C2CC=C4[C@@]3(C)C{16}[C@@H](O)[C@]5({28}CO)[C@H]4CC(C)(C){21}[C@@H](O){22}[C@@H]5O |
Show graphically |
Structure type: oligomer
Trivial name: desacylescin III, desacylescin-III
Compound class: triterpenoid glycoside, triterpene saponin
Reference(s) to other database(s): CCSD:
36735, CBank-STR:9087
- Compound ID: 24331
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Ang-(1-21)-+
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b-D-Glcp-(1-4)-+ |
| |
b-D-Glcp-(1-2)-b-D-GlcpA-(1-3)-Subst22Ac
Subst = protoaescigenin = SMILES C[C@]12CC{3}[C@H](O)[C@](C)({24}CO)C1CC[C@]3(C)C2CC=C4[C@@]3(C)C{16}[C@@H](O)[C@]5({28}CO)[C@H]4CC(C)(C){21}[C@@H](O){22}[C@@H]5O;
Ang = (Z)-2-methylbut-2-enoic (angelic) acid |
Show graphically |
Structure type: oligomer
C55H86O24
Trivial name: escin Ib
Compound class: triterpene saponin
Reference(s) to other database(s): CCSD:
14987, CBank-STR:6410
- Compound ID: 24332
|
Tig-(1-21)-+
|
b-D-Glcp-(1-4)-+ |
| |
b-D-Xylp-(1-2)-b-D-GlcpA-(1-3)-Subst22Ac
Subst = protoaescigenin = SMILES C[C@]12CC{3}[C@H](O)[C@](C)({24}CO)C1CC[C@]3(C)C2CC=C4[C@@]3(C)C{16}[C@@H](O)[C@]5({28}CO)[C@H]4CC(C)(C){21}[C@@H](O){22}[C@@H]5O;
Tig = (E)-2-methylbut-2-enoic (tiglic) acid |
Show graphically |
Structure type: oligomer
C54H84O23
Trivial name: escin IIa
Compound class: triterpene saponin
Reference(s) to other database(s): CCSD:
14988, CBank-STR:6778
- Compound ID: 24333
|
Ang-(1-21)-+
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b-D-Glcp-(1-4)-+ |
| |
b-D-Xylp-(1-2)-b-D-GlcpA-(1-3)-Subst22Ac
Subst = protoaescigenin = SMILES C[C@]12CC{3}[C@H](O)[C@](C)({24}CO)C1CC[C@]3(C)C2CC=C4[C@@]3(C)C{16}[C@@H](O)[C@]5({28}CO)[C@H]4CC(C)(C){21}[C@@H](O){22}[C@@H]5O;
Ang = (Z)-2-methylbut-2-enoic (angelic) acid |
Show graphically |
Structure type: oligomer
C54H84O23
Trivial name: escin IIb
Compound class: triterpene saponin
Reference(s) to other database(s): CCSD:
14989, CBank-STR:6884
- Compound ID: 24334
|
Tig-(1-21)-+
|
b-D-Glcp-(1-4)-+ |
| |
b-D-Galp-(1-2)-b-D-GlcpA-(1-3)-Subst22Ac
Subst = barringtogenol C = SMILES C[C@]12CC{3}[C@H](O)C(C)(C)C1CC[C@]3(C)C2CC=C4[C@@]3(C)C{16}[C@@H](O)[C@]5({28}CO)[C@H]4CC(C)(C){21}[C@@H](O){22}[C@@H]5O;
Tig = (E)-2-methylbut-2-enoic (tiglic) acid |
Show graphically |
Structure type: oligomer
C55H86O23
Trivial name: escin IIIa
Compound class: triterpene saponin
Reference(s) to other database(s): CCSD:
14990, CBank-STR:6950
- Compound ID: 24498
|
Ang-(1-21)-+
|
b-D-Glcp-(1-4)-+ |
| |
b-D-Galp-(1-2)-b-D-GlcpA-(1-3)-Subst22Ac
Subst = barringtogenol C = SMILES C[C@]12CC{3}[C@H](O)C(C)(C)C1CC[C@]3(C)C2CC=C4[C@@]3(C)C{16}[C@@H](O)[C@]5({28}CO)[C@H]4CC(C)(C){21}[C@@H](O){22}[C@@H]5O;
Ang = (Z)-2-methylbut-2-enoic (angelic) acid |
Show graphically |
Structure type: oligomer
; 1113 [M-H]-, 1137.5481 [M+Na]+
C55H85O23
Trivial name: escin IIIb
Compound class: triterpene saponin
Reference(s) to other database(s): CCSD:
15719, CBank-STR:15924
- Compound ID: 24499
|
b-D-Glcp-(1-4)-+
|
b-D-Glcp-(1-2)-b-D-GlcpA-(1-3)-Subst21Ac22Ac
Subst = protoaescigenin = SMILES C[C@]12CC{3}[C@H](O)[C@](C)({24}CO)C1CC[C@]3(C)C2CC=C4[C@@]3(C)C{16}[C@@H](O)[C@]5({28}CO)[C@H]4CC(C)(C){21}[C@@H](O){22}[C@@H]5O |
Show graphically |
Structure type: oligomer
; 1089 [M-H]-, 1113.5071 [M+Na]+
C52H82O24
Trivial name: escin IV
Compound class: triterpene saponin
Reference(s) to other database(s): CCSD:
15807, CBank-STR:15928
- Compound ID: 24500
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iBut-(1-21)-+
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b-D-Glcp-(1-4)-+ |
| |
b-D-Glcp-(1-2)-b-D-GlcpA-(1-3)-Subst22Ac
Subst = protoaescigenin = SMILES C[C@]12CC{3}[C@H](O)[C@](C)({24}CO)C1CC[C@]3(C)C2CC=C4[C@@]3(C)C{16}[C@@H](O)[C@]5({28}CO)[C@H]4CC(C)(C){21}[C@@H](O){22}[C@@H]5O |
Show graphically |
Structure type: oligomer
; 1117 [M-H]-, 1141.5410 [M+Na]+
C54H86O24
Trivial name: escin V
Compound class: triterpene saponin
Reference(s) to other database(s): CCSD:
15829, CBank-STR:15931
- Compound ID: 24501
|
aiVl-(1-21)-+
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b-D-Glcp-(1-4)-+ |
| |
b-D-Glcp-(1-2)-b-D-GlcpA-(1-3)-Subst22Ac
Subst = protoaescigenin = SMILES C[C@]12CC{3}[C@H](O)[C@](C)({24}CO)C1CC[C@]3(C)C2CC=C4[C@@]3(C)C{16}[C@@H](O)[C@]5({28}CO)[C@H]4CC(C)(C){21}[C@@H](O){22}[C@@H]5O |
Show graphically |
Structure type: oligomer
; 1131 [M-H]-, 1155.5587 [M+Na]+
C55H88O24
Trivial name: escin VI
Compound class: triterpene saponin
Reference(s) to other database(s): CCSD:
15844, CBank-STR:15933
- Compound ID: 24502
|
Tig-(1-21)-+
|
b-D-Glcp-(1-4)-+ |
| |
b-D-Glcp-(1-2)-b-D-GlcpA-(1-3)-Subst28Ac
Subst = protoaescigenin = SMILES C[C@]12CC{3}[C@H](O)[C@](C)({24}CO)C1CC[C@]3(C)C2CC=C4[C@@]3(C)C{16}[C@@H](O)[C@]5({28}CO)[C@H]4CC(C)(C){21}[C@@H](O){22}[C@@H]5O;
Tig = (E)-2-methylbut-2-enoic (tiglic) acid |
Show graphically |
Structure type: oligomer
; 1129.5431 [M-H]-
C55H86O24
Trivial name: isoescin Ia
Compound class: triterpene saponin
Reference(s) to other database(s): CCSD:
15870, CBank-STR:15938
- Compound ID: 24503
|
Ang-(1-21)-+
|
b-D-Glcp-(1-4)-+ |
| |
b-D-Glcp-(1-2)-b-D-GlcpA-(1-3)-Subst28Ac
Subst = protoaescigenin = SMILES C[C@]12CC{3}[C@H](O)[C@](C)({24}CO)C1CC[C@]3(C)C2CC=C4[C@@]3(C)C{16}[C@@H](O)[C@]5({28}CO)[C@H]4CC(C)(C){21}[C@@H](O){22}[C@@H]5O;
Ang = (Z)-2-methylbut-2-enoic (angelic) acid |
Show graphically |
Structure type: oligomer
; 1129.5324 [M-H]-
C55H86O24
Trivial name: isoescin Ib
Compound class: triterpene saponin
Reference(s) to other database(s): CCSD:
15871, CBank-STR:15961
- Compound ID: 24504
|
iBut-(1-21)-+
|
b-D-Glcp-(1-4)-+ |
| |
b-D-Glcp-(1-2)-b-D-GlcpA-(1-3)-Subst28Ac
Subst = protoaescigenin = SMILES C[C@]12CC{3}[C@H](O)[C@](C)({24}CO)C1CC[C@]3(C)C2CC=C4[C@@]3(C)C{16}[C@@H](O)[C@]5({28}CO)[C@H]4CC(C)(C){21}[C@@H](O){22}[C@@H]5O |
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Structure type: oligomer
; 1117 [M-H]-, 1141.5374 [M+Na]+
C54H86O24
Trivial name: isoescin V
Compound class: triterpene saponin
Reference(s) to other database(s): CCSD:
15877, CBank-STR:16075
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