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Akhov LS, Musienko MM, Piacente S, Pizza C, Oleszek W
Structure of steroidal saponins from underground parts of Allium nutans L.
Journal of Agricultural and Food Chemistry 47(8) (1999)
3193-3196
|
b-D-Glcp-(1-26)-+
|
b-D-Glcp-(1-4)-+ |
| |
a-L-Rhap-(1-2)-b-D-Glcp-(1-3)-Subst
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 |
Show graphically |
Allium nutans
(NCBI TaxID 138328,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: underground part
The structure was elucidated in this paperNCBI PubMed ID: 10552629Publication DOI: 10.1021/jf9901800Journal NLM ID: 0374755Publisher: American Chemical Society
Correspondence: Oleszek W <WO
iung.Pulawy.pl>
Institutions: Department of Biochemistry, Institute of Soil Science and Plant Cultivation, ul. Czartoryskich 8, 24-100 Pulawy, Poland, Department of Plant Physiology, Kyiv State University, Vladimirskaya Str. 64, 252033 Kyiv, Ukraine, Dipartimento di Scienze Farmaceutiche, Universita degli Studi di Salerno, Piazza V. Emanuele 9, 84084, Salerno, Italy
Four steroidal glycosides including deltoside and nolinofuroside D and two novel saponins were isolated from underground parts of Allium nutans L. On the basis of the spectral (LSIMS and NMR) analysis, the structures of the new compounds were established as 25R Δ5-spirostan 3β-ol-3-O-{α-L-rhamnopyranosyl(l→2)-[β-D-glucopyranosyl(1→4)]-O-β-D-galactopyranoside} and 25R Δ5-spirostan 1β,3β-diol 1-O-β-D-galactopyranoside. On the basis of the extraction efficiency, the concentration of saponins was established to be about 4% of dry matter, which makes this species a good source of steroidal saponins for commercial use.
glycosides, diosgenin, steroidal saponins, ruscogenin, Allium nutans
Structure type: oligomer ; 1065 [M-H]-
Location inside paper: compound 1, table 1(1), fig. 1(1)
Trivial name: deltoside
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, TLC, HPLC, LSI-MS, TOCSY, DFQ-COSY, HSQS
Comments, role: compound was identified based on data from ref. [Agrawal, 1985]; NMR temperature was not specified
Related record ID(s): 63278, 63279, 63280
NCBI Taxonomy refs (TaxIDs): 138328
Show glycosyltransferases
NMR conditions: in CD3OD
[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
3,2 aLRhap 101.9 72.2 72.5 74.0 69.7 17.6
3,4 bDGlcp 104.7 75.1 78.2 71.8 77.9 62.4
3 bDGlcp 100.5 78.7 77.9 81.1 76.3 62.3
26 bDGlcp 104.6 75.2 78.2 71.5 77.9 62.3
Subst 38.48 30.80 79.41 39.6 142.0 122.7 33.02 32.24 51.7 38.1 21.85 40.63 16.78 57.81 32.54 82.43 65.26 16.78 19.6 41.18 16.14 113 32.0 29.04 34.84 17.3 75.98
1H NMR data:
missing...
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 |
|---|
| 3,2 | aLRhap | 101.9 | 72.2 | 72.5 | 74.0 | 69.7 | 17.6 | |
| 3,4 | bDGlcp | 104.7 | 75.1 | 78.2 | 71.8 | 77.9 | 62.4 | |
| 3 | bDGlcp | 100.5 | 78.7 | 77.9 | 81.1 | 76.3 | 62.3 | |
| 26 | bDGlcp | 104.6 | 75.2 | 78.2 | 71.5 | 77.9 | 62.3 | |
| | Subst | 38.48 | 30.80 | 79.41 | 39.6 | 142.0 | 122.7 | 33.02 | 32.24 | 51.7 | 38.1 | 21.85 | 40.63 | 16.78 | 57.81 | 32.54 | 82.43 | 65.26 | 16.78 | 19.6 | 41.18 | 16.14 | 113 | 32.0 | 29.04 | 34.84 | 17.3 | 75.98 |
|
There is only one chemically distinct structure:
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Akhov LS, Musienko MM, Piacente S, Pizza C, Oleszek W
Structure of steroidal saponins from underground parts of Allium nutans L.
Journal of Agricultural and Food Chemistry 47(8) (1999)
3193-3196
|
b-D-Glcp-(1-4)-+
|
a-L-Rhap-(1-2)-b-D-Glcp-(1-3)-Subst
Subst = tigogenin = SMILES [H][C@]1(O[C@@]2(OC[C@H](C)CC2)[C@H]3C)C[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] |
Show graphically |
Allium nutans
(NCBI TaxID 138328,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: underground part
The structure was elucidated in this paperNCBI PubMed ID: 10552629Publication DOI: 10.1021/jf9901800Journal NLM ID: 0374755Publisher: American Chemical Society
Correspondence: Oleszek W <WO
iung.Pulawy.pl>
Institutions: Department of Biochemistry, Institute of Soil Science and Plant Cultivation, ul. Czartoryskich 8, 24-100 Pulawy, Poland, Department of Plant Physiology, Kyiv State University, Vladimirskaya Str. 64, 252033 Kyiv, Ukraine, Dipartimento di Scienze Farmaceutiche, Universita degli Studi di Salerno, Piazza V. Emanuele 9, 84084, Salerno, Italy
Four steroidal glycosides including deltoside and nolinofuroside D and two novel saponins were isolated from underground parts of Allium nutans L. On the basis of the spectral (LSIMS and NMR) analysis, the structures of the new compounds were established as 25R Δ5-spirostan 3β-ol-3-O-{α-L-rhamnopyranosyl(l→2)-[β-D-glucopyranosyl(1→4)]-O-β-D-galactopyranoside} and 25R Δ5-spirostan 1β,3β-diol 1-O-β-D-galactopyranoside. On the basis of the extraction efficiency, the concentration of saponins was established to be about 4% of dry matter, which makes this species a good source of steroidal saponins for commercial use.
glycosides, diosgenin, steroidal saponins, ruscogenin, Allium nutans
Structure type: oligomer ; 883 [M-H]-
C
42H
76O
19Location inside paper: compound 2, table 1(2), table 2(2), fig. 1(2)
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, TLC, HPLC, LSI-MS, TOCSY, DFQ-COSY, HSQS
Comments, role: NMR temperature was not specified
Related record ID(s): 63277, 63279, 63280
NCBI Taxonomy refs (TaxIDs): 138328
Show glycosyltransferases
NMR conditions: in DMSO-d6
[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
3,2 aLRhap 99.6 70.3 70.4 71.7 67.5 17.6
3,4 bDGlcp 103.0 73.1 76.3 69.8 76.6 60.5
3 bDGlcp 97.9 75.9 75.7 80.7 74.3 60.1
Subst 36.2 28.8 76.2 36.6 140.1 121.1 30.9 30.8 49.4 37.5 20.8 39.1 39.0 55.6 31.4 80.0 61.6 15.9 18.8 40.9 14.5 109.0 31.3 28.3 29.6 65.8 16.9
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,2 aLRhap 5.08 3.63 3.42 3.22 4.00 1.15
3,4 bDGlcp 4.26 3.00 3.18 3.10 3.22 3.42-3.71
3 bDGlcp 4.52 3.25 3.53 3.30 3.28 3.58-3.75
Subst
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,2 aLRhap 99.6/5.08 70.3/3.63 70.4/3.42 71.7/3.22 67.5/4.00 17.6/1.15
3,4 bDGlcp 103.0/4.26 73.1/3.00 76.3/3.18 69.8/3.10 76.6/3.22 60.5/3.42-3.71
3 bDGlcp 97.9/4.52 75.9/3.25 75.7/3.53 80.7/3.30 74.3/3.28 60.1/3.58-3.75
Subst NMR TSV error 2: unequal length of 13C and 1H datasets
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,2 | aLRhap | 5.08 | 3.63 | 3.42 | 3.22 | 4.00 | 1.15 |
| 3,4 | bDGlcp | 4.26 | 3.00 | 3.18 | 3.10 | 3.22 | 3.42
3.71 |
| 3 | bDGlcp | 4.52 | 3.25 | 3.53 | 3.30 | 3.28 | 3.58
3.75 |
| | Subst | |
|
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 |
|---|
| 3,2 | aLRhap | 99.6 | 70.3 | 70.4 | 71.7 | 67.5 | 17.6 | |
| 3,4 | bDGlcp | 103.0 | 73.1 | 76.3 | 69.8 | 76.6 | 60.5 | |
| 3 | bDGlcp | 97.9 | 75.9 | 75.7 | 80.7 | 74.3 | 60.1 | |
| | Subst | 36.2 | 28.8 | 76.2 | 36.6 | 140.1 | 121.1 | 30.9 | 30.8 | 49.4 | 37.5 | 20.8 | 39.1 | 39.0 | 55.6 | 31.4 | 80.0 | 61.6 | 15.9 | 18.8 | 40.9 | 14.5 | 109.0 | 31.3 | 28.3 | 29.6 | 65.8 | 16.9 |
|
There is only one chemically distinct structure:
Expand this record
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Akhov LS, Musienko MM, Piacente S, Pizza C, Oleszek W
Structure of steroidal saponins from underground parts of Allium nutans L.
Journal of Agricultural and Food Chemistry 47(8) (1999)
3193-3196
|
b-D-Galp-(1-1)-Subst
Subst = 25R-5α-spirostan-1β,3β-diol = SMILES [H][C@]1(O[C@@]2(OC[C@H](C)CC2)[C@H]3C)C[C@@]4([H])[C@]5([H])CC[C@@]6([H])C{3}[C@@H](O)C{1}[C@@H](O)[C@]6(C)[C@@]5([H])CC[C@]4(C)[C@]13[H] |
Show graphically |
Allium nutans
(NCBI TaxID 138328,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: underground part
The structure was elucidated in this paperNCBI PubMed ID: 10552629Publication DOI: 10.1021/jf9901800Journal NLM ID: 0374755Publisher: American Chemical Society
Correspondence: Oleszek W <WO
iung.Pulawy.pl>
Institutions: Department of Biochemistry, Institute of Soil Science and Plant Cultivation, ul. Czartoryskich 8, 24-100 Pulawy, Poland, Department of Plant Physiology, Kyiv State University, Vladimirskaya Str. 64, 252033 Kyiv, Ukraine, Dipartimento di Scienze Farmaceutiche, Universita degli Studi di Salerno, Piazza V. Emanuele 9, 84084, Salerno, Italy
Four steroidal glycosides including deltoside and nolinofuroside D and two novel saponins were isolated from underground parts of Allium nutans L. On the basis of the spectral (LSIMS and NMR) analysis, the structures of the new compounds were established as 25R Δ5-spirostan 3β-ol-3-O-{α-L-rhamnopyranosyl(l→2)-[β-D-glucopyranosyl(1→4)]-O-β-D-galactopyranoside} and 25R Δ5-spirostan 1β,3β-diol 1-O-β-D-galactopyranoside. On the basis of the extraction efficiency, the concentration of saponins was established to be about 4% of dry matter, which makes this species a good source of steroidal saponins for commercial use.
glycosides, diosgenin, steroidal saponins, ruscogenin, Allium nutans
Structure type: monomer ; 591 [M-H]-
C
33H
52O
9Location inside paper: compound 3, table 1(3), table 2(3), fig. 1(3)
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_136044,IEDB_137472,IEDB_141794,IEDB_190606,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
Methods: 13C NMR, 1H NMR, TLC, HPLC, LSI-MS, TOCSY, DFQ-COSY, HSQS
Comments, role: NMR temperature was not specified
Related record ID(s): 63277, 63278, 63280
NCBI Taxonomy refs (TaxIDs): 138328
Show glycosyltransferases
NMR conditions: in CD3OD
[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
1 bDGalp 101.9 72.9 74.7 69.6 76.0 62.0
Subst 83.4 36.9 68.6 42.9 139.2 125.7 32.4 33.7 51.3 42.9 24.3 41.1 40.5 57.7 32.6 81.9 63.5 16.7 14.6 42.9 14.7 110.9 32.0 28.5 31.1 65.6 16.7
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
1 bDGalp 4.30 3.52 3.48 3.87 3.47 3.47-3.78
Subst
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
1 bDGalp 101.9/4.30 72.9/3.52 74.7/3.48 69.6/3.87 76.0/3.47 62.0/3.47-3.78
Subst NMR TSV error 2: unequal length of 13C and 1H datasets
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 1 | bDGalp | 4.30 | 3.52 | 3.48 | 3.87 | 3.47 | 3.47
3.78 |
| | Subst | |
|
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 |
|---|
| 1 | bDGalp | 101.9 | 72.9 | 74.7 | 69.6 | 76.0 | 62.0 | |
| | Subst | 83.4 | 36.9 | 68.6 | 42.9 | 139.2 | 125.7 | 32.4 | 33.7 | 51.3 | 42.9 | 24.3 | 41.1 | 40.5 | 57.7 | 32.6 | 81.9 | 63.5 | 16.7 | 14.6 | 42.9 | 14.7 | 110.9 | 32.0 | 28.5 | 31.1 | 65.6 | 16.7 |
|
There is only one chemically distinct structure:
Expand this record
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Akhov LS, Musienko MM, Piacente S, Pizza C, Oleszek W
Structure of steroidal saponins from underground parts of Allium nutans L.
Journal of Agricultural and Food Chemistry 47(8) (1999)
3193-3196
|
b-D-Galp-(1-1)-+
|
b-D-Glcp-(1-26)-Subst
Subst = 25R-furost-5-en-1β,3β,22,26-tetrol = 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({1}[C@H](O)C{3}[C@@H](C5)O)C)C)O{22}C1(CC[C@@H](C){26}[CH2]O)O |
Show graphically |
Allium nutans
(NCBI TaxID 138328,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: underground part
The structure was elucidated in this paperNCBI PubMed ID: 10552629Publication DOI: 10.1021/jf9901800Journal NLM ID: 0374755Publisher: American Chemical Society
Correspondence: Oleszek W <WO
iung.Pulawy.pl>
Institutions: Department of Biochemistry, Institute of Soil Science and Plant Cultivation, ul. Czartoryskich 8, 24-100 Pulawy, Poland, Department of Plant Physiology, Kyiv State University, Vladimirskaya Str. 64, 252033 Kyiv, Ukraine, Dipartimento di Scienze Farmaceutiche, Universita degli Studi di Salerno, Piazza V. Emanuele 9, 84084, Salerno, Italy
Four steroidal glycosides including deltoside and nolinofuroside D and two novel saponins were isolated from underground parts of Allium nutans L. On the basis of the spectral (LSIMS and NMR) analysis, the structures of the new compounds were established as 25R Δ5-spirostan 3β-ol-3-O-{α-L-rhamnopyranosyl(l→2)-[β-D-glucopyranosyl(1→4)]-O-β-D-galactopyranoside} and 25R Δ5-spirostan 1β,3β-diol 1-O-β-D-galactopyranoside. On the basis of the extraction efficiency, the concentration of saponins was established to be about 4% of dry matter, which makes this species a good source of steroidal saponins for commercial use.
glycosides, diosgenin, steroidal saponins, ruscogenin, Allium nutans
Structure type: oligomer ; 771 [M-H]-
C
39H
64O
15Location inside paper: compound 4, table 1(4), table 2(4), fig. 1(4)
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_136044,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_190606,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
Methods: 13C NMR, 1H NMR, TLC, HPLC, LSI-MS, TOCSY, DFQ-COSY, HSQS
Comments, role: NMR temperature was not specified; published erroneous #1_bDGalp С4 chemical shift (63.9) was replaced by a matching candidate (69.4) by CSDB staff
Related record ID(s): 63277, 63278, 63279
NCBI Taxonomy refs (TaxIDs): 138328
Show glycosyltransferases
NMR conditions: in CD3OD
[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
1 bDGalp 101.9 72.1 74.8 69.4 76.0 62.1
26 bDGlcp 104.4 74.9 77.8 71.3 77.6 62.3
Subst 83.7 36.9 68.7 42.6 139.7 125.7 32.3 33.6 51.1 42.7 24.1 40.9 40.5 57.6 32.7 82.2 63.9 16.8 14.6 40.1 15.8 110.7 36.4 28.5 34.5 75.7 16.8
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
1 bDGalp 4.30 3.50 3.49 3.86 3.47 3.75-3.78
26 bDGlcp 4.27 3.20 3.38 3.30 3.28 3.69-3.88
Subst
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
1 bDGalp 101.9/4.30 72.1/3.50 74.8/3.49 69.4/3.86 76.0/3.47 62.1/3.75-3.78
26 bDGlcp 104.4/4.27 74.9/3.20 77.8/3.38 71.3/3.30 77.6/3.28 62.3/3.69-3.88
Subst NMR TSV error 2: unequal length of 13C and 1H datasets
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 1 | bDGalp | 4.30 | 3.50 | 3.49 | 3.86 | 3.47 | 3.75
3.78 |
| 26 | bDGlcp | 4.27 | 3.20 | 3.38 | 3.30 | 3.28 | 3.69
3.88 |
| | Subst | |
|
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 |
|---|
| 1 | bDGalp | 101.9 | 72.1 | 74.8 | 69.4 | 76.0 | 62.1 | |
| 26 | bDGlcp | 104.4 | 74.9 | 77.8 | 71.3 | 77.6 | 62.3 | |
| | Subst | 83.7 | 36.9 | 68.7 | 42.6 | 139.7 | 125.7 | 32.3 | 33.6 | 51.1 | 42.7 | 24.1 | 40.9 | 40.5 | 57.6 | 32.7 | 82.2 | 63.9 | 16.8 | 14.6 | 40.1 | 15.8 | 110.7 | 36.4 | 28.5 | 34.5 | 75.7 | 16.8 |
|
There is only one chemically distinct structure:
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Total list of record IDs on all result pages of the current query:
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