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Yoshikawa M, Murakami T, Komatsu H, Matsuda H
Medicinal foodstuffs. XII. Saponin constituents with adjuvant activity from hyacinth bean, the seeds of Dolichos lablab L. (1): Structures of lablabosides A, B, and C
Chemical and Pharmaceutical Bulletin 46(5) (1998)
812-816
|
b-D-Glcp-(1-28)-+
|
a-L-Rhap-(1-2)-b-D-Galp-(1-2)-b-D-GlcpA-(1-3)-Subst
Subst = oleanolic acid = SMILES O{3}[C@H]1CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])CC(C)(C)CC[C@@]({28}C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@]([H])2C1(C)C |
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Dolichos lablab
(later renamed to: Lablab purpureus)
(NCBI TaxID 35936,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: seed
The structure was elucidated in this paperNCBI PubMed ID: 9621416Publication DOI: 10.1248/cpb.46.812Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Kyoto Pharmaceutical University, Kyoto, Japan
From the glgcoside mixture with adjuvant activity obtained from the hyacinth bean, the seeds of Dolichos lablab L., six new oleanane-type triterpene bisdesmosides, lablabosides A, B, C, D, E, and F, were isolated together with chikusetsusaponin IVa. The structures of lablabosides A, B, and C were determined on the basis of chemical and physicochemical evidence as follows: 3-O-[alpha-L-rhamnopyranosyl (1 --> 2)-beta-D-galactopyranosyl (1 --> 2)-beta-D-glucopyranosiduronic acid]-28-O-(beta-D-glucopyranosyl) oleanolic acid (lablaboside A), 3-O-[alpha-L-rhamnopyranosyl (1 --> 2)-beta-D-galactopyranosyl (1 --> 2)-beta-D-glucopyranosiduronic acid]-28-O-(beta-D-glucopyranosyl) 24-epi-hederagenin (lablaboside B), 3-O-[alpha-L-rhamnopyranosyl (1 --> 2)-beta-D-galactopyranosyl (1 --> 2)-beta-D-glucopyranosiduronic acid]-28-O-[alpha-L-rhamnopyranosyl (1 --> 2)-beta-D-glucopyranosyl] 24-epi-hederagenin (lablaboside C).
adjuvant activity, medicinal foodstuff, hyacinth bean, lablaboside, Dolichos lablab, oleanane-type triterpene bisdesmoside
Structure type: oligomer ; 1125.5436 [M+Na]+
C
54H
86O
23Location inside paper: Chart 2, compound 1, table 1
Trivial name: lablaboside A
Compound class: triterpenoid glycoside
Contained glycoepitopes: IEDB_115136,IEDB_136044,IEDB_136105,IEDB_137472,IEDB_140630,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_190606,IEDB_225177,IEDB_423153,IEDB_885823,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
Methods: 13C NMR, 1H NMR, IR, FAB-MS, acid hydrolysis, GLC, methanolysis, HPLC, optical rotation measurement, column chromatography, HMBC, HR-FAB-MS, extraciton, mehtanolysis
Related record ID(s): 61209, 61210, 61211
NCBI Taxonomy refs (TaxIDs): 35936
Show glycosyltransferases
NMR conditions: in C5D5N
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16 C17 C18 C19 C20 C21 C22 C23 C24 C25 C26 C27 C28 C29 C30
3,2,2 aLRhap 102.0 72.4 72.7 74.4 69.5 18.9
3,2 bDGalp 102.8 76.7 76.1 70.6 76.3 62.0
3 bDGlcpA 105.3 79.4 78.8 73.4 77.4 172.5
28 bDGlcp 95.8 74.2 78.9 71.3 79.2 62.4
Subst 38.8 26.5 90.0 39.7 56.0 18.6 33.2 40.0 48.1 37.0 23.5 122.9 144.1 42.2 28.3 23.8 47.0 41.8 46.2 30.8 34.1 32.6 28.5 16.8 15.5 17.5 26.1 176.4 33.1 23.7
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16 H17 H18 H19 H20 H21 H22 H23 H24 H25 H26 H27 H28 H29 H30
3,2,2 aLRhap 6.25 ? ? ? ? 1.74
3,2 bDGalp 5.66 ? ? ? ? ?
3 bDGlcpA 5.03 ? ? ? ? -
28 bDGlcp 6.28 ? ? ? ? ?
Subst ? ? 3.30 - ? ? ? - - - ? 5.39 - - ? ? - 3.17 ? - ? ? 1.36 1.13 0.82 1.06 1.25 ? 0.91 0.88
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8 C9/H9 C10/H10 C11/H11 C12/H12 C13/H13 C14/H14 C15/H15 C16/H16 C17/H17 C18/H18 C19/H19 C20/H20 C21/H21 C22/H22 C23/H23 C24/H24 C25/H25 C26/H26 C27/H27 C28/H28 C29/H29 C30/H30
3,2,2 aLRhap 102.0/6.25 72.4/? 72.7/? 74.4/? 69.5/? 18.9/1.74
3,2 bDGalp 102.8/5.66 76.7/? 76.1/? 70.6/? 76.3/? 62.0/?
3 bDGlcpA 105.3/5.03 79.4/? 78.8/? 73.4/? 77.4/?
28 bDGlcp 95.8/6.28 74.2/? 78.9/? 71.3/? 79.2/? 62.4/?
Subst 38.8/? 26.5/? 90.0/3.30 56.0/? 18.6/? 33.2/? 23.5/? 122.9/5.39 28.3/? 23.8/? 41.8/3.17 46.2/? 34.1/? 32.6/? 28.5/1.36 16.8/1.13 15.5/0.82 17.5/1.06 26.1/1.25 176.4/? 33.1/0.91 23.7/0.88
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 | H17 | H18 | H19 | H20 | H21 | H22 | H23 | H24 | H25 | H26 | H27 | H28 | H29 | H30 |
|---|
| 3,2,2 | aLRhap | 6.25 | ? | ? | ? | ? | 1.74 | |
| 3,2 | bDGalp | 5.66 | ? | ? | ? | ? | ? | |
| 3 | bDGlcpA | 5.03 | ? | ? | ? | ? |
| |
| 28 | bDGlcp | 6.28 | ? | ? | ? | ? | ? | |
| | Subst | ? | ? | 3.30 |
| ? | ? | ? |
|
|
| ? | 5.39 |
|
| ? | ? |
| 3.17 | ? |
| ? | ? | 1.36 | 1.13 | 0.82 | 1.06 | 1.25 | ? | 0.91 | 0.88 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 | C16 | C17 | C18 | C19 | C20 | C21 | C22 | C23 | C24 | C25 | C26 | C27 | C28 | C29 | C30 |
|---|
| 3,2,2 | aLRhap | 102.0 | 72.4 | 72.7 | 74.4 | 69.5 | 18.9 | |
| 3,2 | bDGalp | 102.8 | 76.7 | 76.1 | 70.6 | 76.3 | 62.0 | |
| 3 | bDGlcpA | 105.3 | 79.4 | 78.8 | 73.4 | 77.4 | 172.5 | |
| 28 | bDGlcp | 95.8 | 74.2 | 78.9 | 71.3 | 79.2 | 62.4 | |
| | Subst | 38.8 | 26.5 | 90.0 | 39.7 | 56.0 | 18.6 | 33.2 | 40.0 | 48.1 | 37.0 | 23.5 | 122.9 | 144.1 | 42.2 | 28.3 | 23.8 | 47.0 | 41.8 | 46.2 | 30.8 | 34.1 | 32.6 | 28.5 | 16.8 | 15.5 | 17.5 | 26.1 | 176.4 | 33.1 | 23.7 |
|
There is only one chemically distinct structure:
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Yoshikawa M, Murakami T, Komatsu H, Matsuda H
Medicinal foodstuffs. XII. Saponin constituents with adjuvant activity from hyacinth bean, the seeds of Dolichos lablab L. (1): Structures of lablabosides A, B, and C
Chemical and Pharmaceutical Bulletin 46(5) (1998)
812-816
|
b-D-Glcp-(1-28)-+
|
a-L-Rhap-(1-2)-b-D-Galp-(1-2)-b-D-GlcpA-(1-3)-Subst
Subst = hederagenin = SMILES CC1(C)CC[C@]2({28}C(O)=O)CC[C@@]3(C)[C@]4(C)CC[C@@]5([H])[C@](C)({23}CO){3}[C@@H](O)CC[C@]5(C)[C@@]4([H])CC=C3[C@]2([H])C1 |
Show graphically |
Dolichos lablab
(later renamed to: Lablab purpureus)
(NCBI TaxID 35936,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: seed
The structure was elucidated in this paperNCBI PubMed ID: 9621416Publication DOI: 10.1248/cpb.46.812Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Kyoto Pharmaceutical University, Kyoto, Japan
From the glgcoside mixture with adjuvant activity obtained from the hyacinth bean, the seeds of Dolichos lablab L., six new oleanane-type triterpene bisdesmosides, lablabosides A, B, C, D, E, and F, were isolated together with chikusetsusaponin IVa. The structures of lablabosides A, B, and C were determined on the basis of chemical and physicochemical evidence as follows: 3-O-[alpha-L-rhamnopyranosyl (1 --> 2)-beta-D-galactopyranosyl (1 --> 2)-beta-D-glucopyranosiduronic acid]-28-O-(beta-D-glucopyranosyl) oleanolic acid (lablaboside A), 3-O-[alpha-L-rhamnopyranosyl (1 --> 2)-beta-D-galactopyranosyl (1 --> 2)-beta-D-glucopyranosiduronic acid]-28-O-(beta-D-glucopyranosyl) 24-epi-hederagenin (lablaboside B), 3-O-[alpha-L-rhamnopyranosyl (1 --> 2)-beta-D-galactopyranosyl (1 --> 2)-beta-D-glucopyranosiduronic acid]-28-O-[alpha-L-rhamnopyranosyl (1 --> 2)-beta-D-glucopyranosyl] 24-epi-hederagenin (lablaboside C).
adjuvant activity, medicinal foodstuff, hyacinth bean, lablaboside, Dolichos lablab, oleanane-type triterpene bisdesmoside
Structure type: oligomer ; 1141.5385 [M+Na]+
C
54H
86O
24Location inside paper: Chart 2, compound 2, table 1
Trivial name: lablaboside B
Compound class: triterpenoid glycoside
Contained glycoepitopes: IEDB_115136,IEDB_136044,IEDB_136105,IEDB_137472,IEDB_140630,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_190606,IEDB_225177,IEDB_423153,IEDB_885823,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
Methods: 13C NMR, 1H NMR, IR, FAB-MS, acid hydrolysis, GLC, methanolysis, HPLC, optical rotation measurement, column chromatography, HMBC, HR-FAB-MS, extraciton, mehtanolysis
Related record ID(s): 61208, 61210, 61211
NCBI Taxonomy refs (TaxIDs): 35936
Show glycosyltransferases
NMR conditions: in C5D5N
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16 C17 C18 C19 C20 C21 C22 C23 C24 C25 C26 C27 C28 C29 C30
3,2,2 aLRhap 102.3 72.4 72.8 74.4 69.4 18.9
3,2 bDGalp 101.8 77.7 76.6 71.3 76.4 61.8
3 bDGlcpA 105.4 77.0 78.5 73.8 77.6 172.3
28 bDGlcp 95.8 74.2 78.9 71.3 79.2 62.4
Subst 38.6 26.7 91.3 43.9 56.2 18.6 33.3 39.9 47.9 36.6 24.0 122.8 144.1 42.2 28.3 23.5 47.1 41.8 46.3 30.8 34.1 32.6 23.0 63.6 15.7 17.4 26.0 176.4 33.1 23.7
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16 H17 H18 H19 H20 H21 H22 H23 H24 H25 H26 H27 H28 H29 H30
3,2,2 aLRhap 6.21 ? ? ? ? 1.75
3,2 bDGalp 5.72 ? ? ? ? ?
3 bDGlcpA 4.96 ? ? ? ? -
28 bDGlcp 6.27 ? ? ? ? ?
Subst ? ? 3.39 - ? ? ? - - - ? 5.38 - - ? ? - 3.15 ? - ? ? 1.41 3.22-4.22 0.65 1.01 1.26 ? 0.90 0.88
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8 C9/H9 C10/H10 C11/H11 C12/H12 C13/H13 C14/H14 C15/H15 C16/H16 C17/H17 C18/H18 C19/H19 C20/H20 C21/H21 C22/H22 C23/H23 C24/H24 C25/H25 C26/H26 C27/H27 C28/H28 C29/H29 C30/H30
3,2,2 aLRhap 102.3/6.21 72.4/? 72.8/? 74.4/? 69.4/? 18.9/1.75
3,2 bDGalp 101.8/5.72 77.7/? 76.6/? 71.3/? 76.4/? 61.8/?
3 bDGlcpA 105.4/4.96 77.0/? 78.5/? 73.8/? 77.6/?
28 bDGlcp 95.8/6.27 74.2/? 78.9/? 71.3/? 79.2/? 62.4/?
Subst 38.6/? 26.7/? 91.3/3.39 56.2/? 18.6/? 33.3/? 24.0/? 122.8/5.38 28.3/? 23.5/? 41.8/3.15 46.3/? 34.1/? 32.6/? 23.0/1.41 63.6/3.22-4.22 15.7/0.65 17.4/1.01 26.0/1.26 176.4/? 33.1/0.90 23.7/0.88
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 | H17 | H18 | H19 | H20 | H21 | H22 | H23 | H24 | H25 | H26 | H27 | H28 | H29 | H30 |
|---|
| 3,2,2 | aLRhap | 6.21 | ? | ? | ? | ? | 1.75 | |
| 3,2 | bDGalp | 5.72 | ? | ? | ? | ? | ? | |
| 3 | bDGlcpA | 4.96 | ? | ? | ? | ? |
| |
| 28 | bDGlcp | 6.27 | ? | ? | ? | ? | ? | |
| | Subst | ? | ? | 3.39 |
| ? | ? | ? |
|
|
| ? | 5.38 |
|
| ? | ? |
| 3.15 | ? |
| ? | ? | 1.41 | 3.22
4.22 | 0.65 | 1.01 | 1.26 | ? | 0.90 | 0.88 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 | C16 | C17 | C18 | C19 | C20 | C21 | C22 | C23 | C24 | C25 | C26 | C27 | C28 | C29 | C30 |
|---|
| 3,2,2 | aLRhap | 102.3 | 72.4 | 72.8 | 74.4 | 69.4 | 18.9 | |
| 3,2 | bDGalp | 101.8 | 77.7 | 76.6 | 71.3 | 76.4 | 61.8 | |
| 3 | bDGlcpA | 105.4 | 77.0 | 78.5 | 73.8 | 77.6 | 172.3 | |
| 28 | bDGlcp | 95.8 | 74.2 | 78.9 | 71.3 | 79.2 | 62.4 | |
| | Subst | 38.6 | 26.7 | 91.3 | 43.9 | 56.2 | 18.6 | 33.3 | 39.9 | 47.9 | 36.6 | 24.0 | 122.8 | 144.1 | 42.2 | 28.3 | 23.5 | 47.1 | 41.8 | 46.3 | 30.8 | 34.1 | 32.6 | 23.0 | 63.6 | 15.7 | 17.4 | 26.0 | 176.4 | 33.1 | 23.7 |
|
There is only one chemically distinct structure:
Expand this record
Collapse this record
Yoshikawa M, Murakami T, Komatsu H, Matsuda H
Medicinal foodstuffs. XII. Saponin constituents with adjuvant activity from hyacinth bean, the seeds of Dolichos lablab L. (1): Structures of lablabosides A, B, and C
Chemical and Pharmaceutical Bulletin 46(5) (1998)
812-816
|
a-L-Rhap-(1-2)-b-D-Glcp-(1-28)-+
|
a-L-Rhap-(1-2)-b-D-Galp-(1-2)-b-D-GlcpA-(1-3)-Hederagenin |
Show graphically |
Dolichos lablab
(later renamed to: Lablab purpureus)
(NCBI TaxID 35936,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: seed
The structure was elucidated in this paperNCBI PubMed ID: 9621416Publication DOI: 10.1248/cpb.46.812Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Kyoto Pharmaceutical University, Kyoto, Japan
From the glgcoside mixture with adjuvant activity obtained from the hyacinth bean, the seeds of Dolichos lablab L., six new oleanane-type triterpene bisdesmosides, lablabosides A, B, C, D, E, and F, were isolated together with chikusetsusaponin IVa. The structures of lablabosides A, B, and C were determined on the basis of chemical and physicochemical evidence as follows: 3-O-[alpha-L-rhamnopyranosyl (1 --> 2)-beta-D-galactopyranosyl (1 --> 2)-beta-D-glucopyranosiduronic acid]-28-O-(beta-D-glucopyranosyl) oleanolic acid (lablaboside A), 3-O-[alpha-L-rhamnopyranosyl (1 --> 2)-beta-D-galactopyranosyl (1 --> 2)-beta-D-glucopyranosiduronic acid]-28-O-(beta-D-glucopyranosyl) 24-epi-hederagenin (lablaboside B), 3-O-[alpha-L-rhamnopyranosyl (1 --> 2)-beta-D-galactopyranosyl (1 --> 2)-beta-D-glucopyranosiduronic acid]-28-O-[alpha-L-rhamnopyranosyl (1 --> 2)-beta-D-glucopyranosyl] 24-epi-hederagenin (lablaboside C).
adjuvant activity, medicinal foodstuff, hyacinth bean, lablaboside, Dolichos lablab, oleanane-type triterpene bisdesmoside
Structure type: oligomer ; 1287.5996 [M+Na]+
C
60H
96O
28Location inside paper: Chart 2, compound 3, table 1
Trivial name: lablaboside C
Compound class: triterpenoid glycoside
Contained glycoepitopes: IEDB_115136,IEDB_136044,IEDB_136105,IEDB_137472,IEDB_140630,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_190606,IEDB_225177,IEDB_423153,IEDB_885823,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
Methods: 13C NMR, 1H NMR, IR, FAB-MS, acid hydrolysis, GLC, methanolysis, HPLC, optical rotation measurement, column chromatography, HMBC, HR-FAB-MS, extraciton, mehtanolysis
Related record ID(s): 61208, 61209, 61211
NCBI Taxonomy refs (TaxIDs): 35936
Show glycosyltransferases
NMR conditions: in C5D5N
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16 C17 C18 C19 C20 C21 C22 C23 C24 C25 C26 C27 C28 C29 C30
3,2,2 aLRhap 102.5 72.5 72.8 74.4 69.5 19.0
3,2 bDGalp 101.7 77.9 76.6 71.2 76.4 61.6
3 bDGlcpA 105.6 76.6 78.5 73.9 77.7 172.4
28,2 aLRhap 101.4 72.3 72.6 73.9 69.8 18.7
28 bDGlcp 94.9 75.6 79.9 71.4 79.0 62.1
xXHederagenin 38.6 26.7 91.3 43.9 56.2 18.6 33.3 39.9 47.9 36.6 24.0 122.8 144.1 42.2 28.3 23.4 47.1 41.8 46.3 30.8 34.1 32.6 23.0 63.6 15.7 17.4 26.0 176.4 33.1 23.7
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16 H17 H18 H19 H20 H21 H22 H23 H24 H25 H26 H27 H28 H29 H30
3,2,2 aLRhap 6.28 ? ? ? ? 1.81
3,2 bDGalp 5.41 ? ? ? ? ?
3 bDGlcpA 4.98 ? ? ? ? -
28,2 aLRhap 6.66 ? ? ? ? 1.79
28 bDGlcp 6.19 ? ? ? ? ?
xXHederagenin ? ? 3.34 - ? ? ? - - - ? 5.38 - - ? ? - 3.10 ? - ? ? 1.35 3.13-4.19 0.63 0.99 1.28 ? 0.89 0.80
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8 C9/H9 C10/H10 C11/H11 C12/H12 C13/H13 C14/H14 C15/H15 C16/H16 C17/H17 C18/H18 C19/H19 C20/H20 C21/H21 C22/H22 C23/H23 C24/H24 C25/H25 C26/H26 C27/H27 C28/H28 C29/H29 C30/H30
3,2,2 aLRhap 102.5/6.28 72.5/? 72.8/? 74.4/? 69.5/? 19.0/1.81
3,2 bDGalp 101.7/5.41 77.9/? 76.6/? 71.2/? 76.4/? 61.6/?
3 bDGlcpA 105.6/4.98 76.6/? 78.5/? 73.9/? 77.7/?
28,2 aLRhap 101.4/6.66 72.3/? 72.6/? 73.9/? 69.8/? 18.7/1.79
28 bDGlcp 94.9/6.19 75.6/? 79.9/? 71.4/? 79.0/? 62.1/?
xXHederagenin 38.6/? 26.7/? 91.3/3.34 56.2/? 18.6/? 33.3/? 24.0/? 122.8/5.38 28.3/? 23.4/? 41.8/3.10 46.3/? 34.1/? 32.6/? 23.0/1.35 63.6/3.13-4.19 15.7/0.63 17.4/0.99 26.0/1.28 176.4/? 33.1/0.89 23.7/0.80
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 | H17 | H18 | H19 | H20 | H21 | H22 | H23 | H24 | H25 | H26 | H27 | H28 | H29 | H30 |
|---|
| 3,2,2 | aLRhap | 6.28 | ? | ? | ? | ? | 1.81 | |
| 3,2 | bDGalp | 5.41 | ? | ? | ? | ? | ? | |
| 3 | bDGlcpA | 4.98 | ? | ? | ? | ? |
| |
| 28,2 | aLRhap | 6.66 | ? | ? | ? | ? | 1.79 | |
| 28 | bDGlcp | 6.19 | ? | ? | ? | ? | ? | |
| | xXHederagenin | ? | ? | 3.34 |
| ? | ? | ? |
|
|
| ? | 5.38 |
|
| ? | ? |
| 3.10 | ? |
| ? | ? | 1.35 | 3.13
4.19 | 0.63 | 0.99 | 1.28 | ? | 0.89 | 0.80 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 | C16 | C17 | C18 | C19 | C20 | C21 | C22 | C23 | C24 | C25 | C26 | C27 | C28 | C29 | C30 |
|---|
| 3,2,2 | aLRhap | 102.5 | 72.5 | 72.8 | 74.4 | 69.5 | 19.0 | |
| 3,2 | bDGalp | 101.7 | 77.9 | 76.6 | 71.2 | 76.4 | 61.6 | |
| 3 | bDGlcpA | 105.6 | 76.6 | 78.5 | 73.9 | 77.7 | 172.4 | |
| 28,2 | aLRhap | 101.4 | 72.3 | 72.6 | 73.9 | 69.8 | 18.7 | |
| 28 | bDGlcp | 94.9 | 75.6 | 79.9 | 71.4 | 79.0 | 62.1 | |
| | xXHederagenin | 38.6 | 26.7 | 91.3 | 43.9 | 56.2 | 18.6 | 33.3 | 39.9 | 47.9 | 36.6 | 24.0 | 122.8 | 144.1 | 42.2 | 28.3 | 23.4 | 47.1 | 41.8 | 46.3 | 30.8 | 34.1 | 32.6 | 23.0 | 63.6 | 15.7 | 17.4 | 26.0 | 176.4 | 33.1 | 23.7 |
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There is only one chemically distinct structure:
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Yoshikawa M, Murakami T, Komatsu H, Matsuda H
Medicinal foodstuffs. XII. Saponin constituents with adjuvant activity from hyacinth bean, the seeds of Dolichos lablab L. (1): Structures of lablabosides A, B, and C
Chemical and Pharmaceutical Bulletin 46(5) (1998)
812-816
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b-D-Glcp-(1-28)-+
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b-D-GlcpA-(1-3)-Subst
Subst = oleanolic acid = SMILES O{3}[C@H]1CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])CC(C)(C)CC[C@@]({28}C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@]([H])2C1(C)C |
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Dolichos lablab
(later renamed to: Lablab purpureus)
(NCBI TaxID 35936,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: seed
The structure was elucidated in this paperNCBI PubMed ID: 9621416Publication DOI: 10.1248/cpb.46.812Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Kyoto Pharmaceutical University, Kyoto, Japan
From the glgcoside mixture with adjuvant activity obtained from the hyacinth bean, the seeds of Dolichos lablab L., six new oleanane-type triterpene bisdesmosides, lablabosides A, B, C, D, E, and F, were isolated together with chikusetsusaponin IVa. The structures of lablabosides A, B, and C were determined on the basis of chemical and physicochemical evidence as follows: 3-O-[alpha-L-rhamnopyranosyl (1 --> 2)-beta-D-galactopyranosyl (1 --> 2)-beta-D-glucopyranosiduronic acid]-28-O-(beta-D-glucopyranosyl) oleanolic acid (lablaboside A), 3-O-[alpha-L-rhamnopyranosyl (1 --> 2)-beta-D-galactopyranosyl (1 --> 2)-beta-D-glucopyranosiduronic acid]-28-O-(beta-D-glucopyranosyl) 24-epi-hederagenin (lablaboside B), 3-O-[alpha-L-rhamnopyranosyl (1 --> 2)-beta-D-galactopyranosyl (1 --> 2)-beta-D-glucopyranosiduronic acid]-28-O-[alpha-L-rhamnopyranosyl (1 --> 2)-beta-D-glucopyranosyl] 24-epi-hederagenin (lablaboside C).
adjuvant activity, medicinal foodstuff, hyacinth bean, lablaboside, Dolichos lablab, oleanane-type triterpene bisdesmoside
Structure type: oligomer
Location inside paper: Chart 2, compound 4
Trivial name: chikusetsusaponin IVa
Compound class: triterpene glycoside, triterpenoid glycoside
Contained glycoepitopes: IEDB_115136,IEDB_140630,IEDB_142488,IEDB_146664,IEDB_423153,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, IR, FAB-MS, acid hydrolysis, GLC, methanolysis, HPLC, optical rotation measurement, column chromatography, HMBC, HR-FAB-MS, extraciton, mehtanolysis
Related record ID(s): 61208, 61209, 61210
NCBI Taxonomy refs (TaxIDs): 35936
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There is only one chemically distinct structure:
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