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Abdel-Gawad MM, El-Sayed MM, Abdel-Hameed ES
Molluscicidal steroidal saponins and lipid content of Agave decipiens
Fitoterapia 70(4) (1999)
371-381
|
b-D-Glcp-(1-26)-+
|
a-L-Rhap-(1-4)-+ |
| |
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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Agave decipiens
(NCBI TaxID 2695036,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: leaf
The structure was elucidated in this paperPublication DOI: 10.1016/S0367-326X(99)00057-XJournal NLM ID: 16930290RPublisher: Elsevier
Institutions: Laboratory of Medicinal Chemistry, Theodor Bilharz Research Institute, Giza, Egypt
GLC analysis of the petrol extract of the leaves of Agave decipiens revealed that n-hexacosane was the main hydrocarbon, β-sitosterol the main sterol and oleic acid the main fatty acid. Two spirostanol and two furostanol saponins have been isolated from the methanolic extract. The structures of these saponins were established as 3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranosyl-26-O-β-D-glucopyranosyl-22α-methoxy-(25R)-furost-5-ene-3β,26-diol (1), neoruscogenin 1-O-β-D-glucopyranosyl-(1→3)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (2), 1-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranosyl-26-O-β-D-glucopyranosyl-22-methylfurosta-5,25(27)-diene-1β,3β,22,26-tetraol (3) and neohecogenin 3-O-β-D-glucopyranosyl-(1→3)-[β-D-xylopyranosyl-(1→3)-β-D-xylopyranosyl-(1→2)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (4). Saponins 2 and 4 showed high molluscicidal activity against B. alexandrina snails (LC90 = 13 and 6 ppm, respectively), whereas saponins 1 and 3 were inactive up to 50 ppm.
fatty acids, steroidal saponins, sterols, molluscicidal activity, Agave decipiens, hydrocarbons
Structure type: oligomer ; 1063 [M+H]+
Location inside paper: compound 1, p. 373 (compound 1), table 1(1), table 2(1)
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, IR, TLC, GLC, CI-MS, methylation analysis, PTLC, HCl hydrolysis, molluscicidal assay
Comments, role: NMR temperature was not specified
Related record ID(s): 62857, 62858, 62859
NCBI Taxonomy refs (TaxIDs): 2695036
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 102.00 70.50 72.60 74.00 69.00 18.50
3,4 aLRhap 102.50 71.60 72.20 74.10 69.00 18.90
3 bDGlcp 100.80 81.00 76.10 77.00 76.80 61.80
22 Me 46.4
26 bDGlcp 105.50 75.20 78.80 71.80 77.80 62.30
Subst 36.2 30.1 77.5 39.1 140.0 121.4 31.9 31.3 45.2 36.2 21.2 39.5 40.6 56.2 32.1 80.5 62.5 16.10 19.10 40.6 15.9 112.1 30.3 28.7 34.2 75.3 17.20
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
3,2 aLRhap
3,4 aLRhap
3 bDGlcp
22 Me 3.12
26 bDGlcp
Subst ? ? ? ? - ? ? ? ? - ? ? - ? ? ? ? 0.67 0.95 ? 1.15 ? ? ? ? ? 0.85
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
3,2 aLRhap NMR TSV error 2: unequal length of 13C and 1H datasets
3,4 aLRhap NMR TSV error 2: unequal length of 13C and 1H datasets
3 bDGlcp NMR TSV error 2: unequal length of 13C and 1H datasets
22 Me 46.4/3.12
26 bDGlcp NMR TSV error 2: unequal length of 13C and 1H datasets
Subst 36.2/? 30.1/? 77.5/? 39.1/? 121.4/? 31.9/? 31.3/? 45.2/? 21.2/? 39.5/? 56.2/? 32.1/? 80.5/? 62.5/? 16.10/0.67 19.10/0.95 40.6/? 15.9/1.15 112.1/? 30.3/? 28.7/? 34.2/? 75.3/? 17.20/0.85
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 |
|---|
| 3,2 | aLRhap | |
| 3,4 | aLRhap | |
| 3 | bDGlcp | |
| 22 | Me | 3.12 | |
| 26 | bDGlcp | |
| | Subst | ? | ? | ? | ? |
| ? | ? | ? | ? |
| ? | ? |
| ? | ? | ? | ? | 0.67 | 0.95 | ? | 1.15 | ? | ? | ? | ? | ? | 0.85 |
|
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 | 102.00 | 70.50 | 72.60 | 74.00 | 69.00 | 18.50 | |
| 3,4 | aLRhap | 102.50 | 71.60 | 72.20 | 74.10 | 69.00 | 18.90 | |
| 3 | bDGlcp | 100.80 | 81.00 | 76.10 | 77.00 | 76.80 | 61.80 | |
| 22 | Me | 46.4 | |
| 26 | bDGlcp | 105.50 | 75.20 | 78.80 | 71.80 | 77.80 | 62.30 | |
| | Subst | 36.2 | 30.1 | 77.5 | 39.1 | 140.0 | 121.4 | 31.9 | 31.3 | 45.2 | 36.2 | 21.2 | 39.5 | 40.6 | 56.2 | 32.1 | 80.5 | 62.5 | 16.10 | 19.10 | 40.6 | 15.9 | 112.1 | 30.3 | 28.7 | 34.2 | 75.3 | 17.20 |
|
There is only one chemically distinct structure:
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Abdel-Gawad MM, El-Sayed MM, Abdel-Hameed ES
Molluscicidal steroidal saponins and lipid content of Agave decipiens
Fitoterapia 70(4) (1999)
371-381
|
b-D-Glcp-(1-3)-+
|
a-L-Rhap-(1-2)-b-D-Glcp-(1-4)-b-D-Galp-(1-1)-Subst
Subst = neoruscogenin = SMILES [H][C@]1(O[C@](OCC2=C)(CC2)[C@H]3C)C[C@@]4([H])[C@]5([H])CC=C6C{3}[C@@H](O)C{1}[C@@H](O)[C@]6(C)[C@@]5([H])CC[C@]4(C)[C@]13[H] |
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Agave decipiens
(NCBI TaxID 2695036,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: leaf
The structure was elucidated in this paperPublication DOI: 10.1016/S0367-326X(99)00057-XJournal NLM ID: 16930290RPublisher: Elsevier
Institutions: Laboratory of Medicinal Chemistry, Theodor Bilharz Research Institute, Giza, Egypt
GLC analysis of the petrol extract of the leaves of Agave decipiens revealed that n-hexacosane was the main hydrocarbon, β-sitosterol the main sterol and oleic acid the main fatty acid. Two spirostanol and two furostanol saponins have been isolated from the methanolic extract. The structures of these saponins were established as 3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranosyl-26-O-β-D-glucopyranosyl-22α-methoxy-(25R)-furost-5-ene-3β,26-diol (1), neoruscogenin 1-O-β-D-glucopyranosyl-(1→3)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (2), 1-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranosyl-26-O-β-D-glucopyranosyl-22-methylfurosta-5,25(27)-diene-1β,3β,22,26-tetraol (3) and neohecogenin 3-O-β-D-glucopyranosyl-(1→3)-[β-D-xylopyranosyl-(1→3)-β-D-xylopyranosyl-(1→2)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (4). Saponins 2 and 4 showed high molluscicidal activity against B. alexandrina snails (LC90 = 13 and 6 ppm, respectively), whereas saponins 1 and 3 were inactive up to 50 ppm.
fatty acids, steroidal saponins, sterols, molluscicidal activity, Agave decipiens, hydrocarbons
Structure type: oligomer ; 1061 [M+H]+
Location inside paper: compound 2, p. 373 (compound 2), table 1(2), table 2(2)
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_136044,IEDB_136105,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_153543,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
Methods: 13C NMR, 1H NMR, IR, TLC, GLC, CI-MS, methylation analysis, PTLC, HCl hydrolysis, molluscicidal assay
Biological activity: Compound 2 had strong molluscicidal activity against B. alexandrina snails with LC90 of 13 ppm within 24 h.
Comments, role: NMR temperature was not specified
Related record ID(s): 62856, 62858, 62859
NCBI Taxonomy refs (TaxIDs): 2695036
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
1,4,2 aLRhap 102.50 71.60 72.50 74.30 69.70 18.30
1,4,3 bDGlcp 104.1 75.20 77.30 71.30 77.60 62.60
1,4 bDGlcp 103.50 81.32 82.60 70.60 72.30 62.20
1 bDGalp 102.40 72.62 75.10 80.10 75.20 61.30
Subst 82.57 37.84 68.74 41.05 139.71 121.20 31.56 32.39 49.45 41.16 23.9 40.42 40.10 55.84 32.33 80.62 64.09 16.07 15.51 41.05 14.68 109.12 33.41 29.71 143.32 64.9 108.65
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
1,4,2 aLRhap 5.10 ? ? ? ? 1.70
1,4,3 bDGlcp
1,4 bDGlcp
1 bDGalp 4.70 ? ? ? ? ?
Subst ? ? ? ? - ? ? ? ? ? ? ? - ? ? ? ? 0.72 1.10 ? 0.87 - ? ? - ? 4.81-4.87
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
1,4,2 aLRhap 102.50/5.10 71.60/? 72.50/? 74.30/? 69.70/? 18.30/1.70
1,4,3 bDGlcp NMR TSV error 2: unequal length of 13C and 1H datasets
1,4 bDGlcp NMR TSV error 2: unequal length of 13C and 1H datasets
1 bDGalp 102.40/4.70 72.62/? 75.10/? 80.10/? 75.20/? 61.30/?
Subst 82.57/? 37.84/? 68.74/? 41.05/? 121.20/? 31.56/? 32.39/? 49.45/? 41.16/? 23.9/? 40.42/? 55.84/? 32.33/? 80.62/? 64.09/? 16.07/0.72 15.51/1.10 41.05/? 14.68/0.87 33.41/? 29.71/? 64.9/? 108.65/4.81-4.87
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 |
|---|
| 1,4,2 | aLRhap | 5.10 | ? | ? | ? | ? | 1.70 | |
| 1,4,3 | bDGlcp | |
| 1,4 | bDGlcp | |
| 1 | bDGalp | 4.70 | ? | ? | ? | ? | ? | |
| | Subst | ? | ? | ? | ? |
| ? | ? | ? | ? | ? | ? | ? |
| ? | ? | ? | ? | 0.72 | 1.10 | ? | 0.87 |
| ? | ? |
| ? | 4.81
4.87 |
|
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 |
|---|
| 1,4,2 | aLRhap | 102.50 | 71.60 | 72.50 | 74.30 | 69.70 | 18.30 | |
| 1,4,3 | bDGlcp | 104.1 | 75.20 | 77.30 | 71.30 | 77.60 | 62.60 | |
| 1,4 | bDGlcp | 103.50 | 81.32 | 82.60 | 70.60 | 72.30 | 62.20 | |
| 1 | bDGalp | 102.40 | 72.62 | 75.10 | 80.10 | 75.20 | 61.30 | |
| | Subst | 82.57 | 37.84 | 68.74 | 41.05 | 139.71 | 121.20 | 31.56 | 32.39 | 49.45 | 41.16 | 23.9 | 40.42 | 40.10 | 55.84 | 32.33 | 80.62 | 64.09 | 16.07 | 15.51 | 41.05 | 14.68 | 109.12 | 33.41 | 29.71 | 143.32 | 64.9 | 108.65 |
|
There is only one chemically distinct structure:
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Abdel-Gawad MM, El-Sayed MM, Abdel-Hameed ES
Molluscicidal steroidal saponins and lipid content of Agave decipiens
Fitoterapia 70(4) (1999)
371-381
|
b-D-Glcp-(1-26)-+
|
a-L-Rhap-(1-4)-+ |
| |
a-L-Rhap-(1-2)-b-D-Glcp-(1-1)-Subst22Me
Subst = furosta-5,25(27)-dien-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(CCC(=C){26}[CH2]O)O |
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Agave decipiens
(NCBI TaxID 2695036,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: leaf
The structure was elucidated in this paperPublication DOI: 10.1016/S0367-326X(99)00057-XJournal NLM ID: 16930290RPublisher: Elsevier
Institutions: Laboratory of Medicinal Chemistry, Theodor Bilharz Research Institute, Giza, Egypt
GLC analysis of the petrol extract of the leaves of Agave decipiens revealed that n-hexacosane was the main hydrocarbon, β-sitosterol the main sterol and oleic acid the main fatty acid. Two spirostanol and two furostanol saponins have been isolated from the methanolic extract. The structures of these saponins were established as 3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranosyl-26-O-β-D-glucopyranosyl-22α-methoxy-(25R)-furost-5-ene-3β,26-diol (1), neoruscogenin 1-O-β-D-glucopyranosyl-(1→3)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (2), 1-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranosyl-26-O-β-D-glucopyranosyl-22-methylfurosta-5,25(27)-diene-1β,3β,22,26-tetraol (3) and neohecogenin 3-O-β-D-glucopyranosyl-(1→3)-[β-D-xylopyranosyl-(1→3)-β-D-xylopyranosyl-(1→2)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (4). Saponins 2 and 4 showed high molluscicidal activity against B. alexandrina snails (LC90 = 13 and 6 ppm, respectively), whereas saponins 1 and 3 were inactive up to 50 ppm.
fatty acids, steroidal saponins, sterols, molluscicidal activity, Agave decipiens, hydrocarbons
Structure type: oligomer ; 1077 [M+H]+
Location inside paper: compound 3, p. 373 (compound 3), table 1(3), table 2(3)
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, IR, TLC, GLC, CI-MS, methylation analysis, PTLC, HCl hydrolysis, molluscicidal assay
Comments, role: NMR temperature was not specified
Related record ID(s): 62856, 62857, 62859
NCBI Taxonomy refs (TaxIDs): 2695036
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
1,2 aLRhap 102.50 71.60 72.10 74.20 69.30 18.30
1,4 aLRhap 101.50 72.80 72.30 74.10 69.10 18.50
1 bDGlcp 103.50 79.80 76.20 81.90 76.30 62.10
22 Me 46.3
26 bDGlcp 104.50 75.10 77.90 71.20 78.20 62.60
Subst 82.51 37.50 68.3 41.9 139.5 121.5 31.5 32.6 49.40 42.4 24.7 40.3 40.1 55.5 31.5 80.02 63.50 16.40 14.60 40.20 15.90 112.10 31.50 27.80 146.0 71.8 111.2
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
1,2 aLRhap
1,4 aLRhap
1 bDGlcp
22 Me 3.24
26 bDGlcp
Subst ? ? ? ? - ? ? ? ? ? ? ? - ? ? ? ? 0.75 1.0 ? 0.90 - ? ? - ? ?
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
1,2 aLRhap NMR TSV error 2: unequal length of 13C and 1H datasets
1,4 aLRhap NMR TSV error 2: unequal length of 13C and 1H datasets
1 bDGlcp NMR TSV error 2: unequal length of 13C and 1H datasets
22 Me 46.3/3.24
26 bDGlcp NMR TSV error 2: unequal length of 13C and 1H datasets
Subst 82.51/? 37.50/? 68.3/? 41.9/? 121.5/? 31.5/? 32.6/? 49.40/? 42.4/? 24.7/? 40.3/? 55.5/? 31.5/? 80.02/? 63.50/? 16.40/0.75 14.60/1.0 40.20/? 15.90/0.90 31.50/? 27.80/? 71.8/? 111.2/?
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 |
|---|
| 1,2 | aLRhap | |
| 1,4 | aLRhap | |
| 1 | bDGlcp | |
| 22 | Me | 3.24 | |
| 26 | bDGlcp | |
| | Subst | ? | ? | ? | ? |
| ? | ? | ? | ? | ? | ? | ? |
| ? | ? | ? | ? | 0.75 | 1.0 | ? | 0.90 |
| ? | ? |
| ? | ? |
|
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 |
|---|
| 1,2 | aLRhap | 102.50 | 71.60 | 72.10 | 74.20 | 69.30 | 18.30 | |
| 1,4 | aLRhap | 101.50 | 72.80 | 72.30 | 74.10 | 69.10 | 18.50 | |
| 1 | bDGlcp | 103.50 | 79.80 | 76.20 | 81.90 | 76.30 | 62.10 | |
| 22 | Me | 46.3 | |
| 26 | bDGlcp | 104.50 | 75.10 | 77.90 | 71.20 | 78.20 | 62.60 | |
| | Subst | 82.51 | 37.50 | 68.3 | 41.9 | 139.5 | 121.5 | 31.5 | 32.6 | 49.40 | 42.4 | 24.7 | 40.3 | 40.1 | 55.5 | 31.5 | 80.02 | 63.50 | 16.40 | 14.60 | 40.20 | 15.90 | 112.10 | 31.50 | 27.80 | 146.0 | 71.8 | 111.2 |
|
There is only one chemically distinct structure:
Expand this record
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Abdel-Gawad MM, El-Sayed MM, Abdel-Hameed ES
Molluscicidal steroidal saponins and lipid content of Agave decipiens
Fitoterapia 70(4) (1999)
371-381
|
b-D-Glcp-(1-3)-+
|
b-D-Xylp-(1-3)-b-D-Xylp-(1-2)-b-D-Glcp-(1-4)-b-D-Galp-(1-3)-Subst
Subst = neohecogenin = SMILES C[C@]12CC{3}[C@H](O)C[C@]1([H])CC[C@]3([H])[C@@]2(CC([C@@]4(C)[C@@]3([H])C[C@@]5(C)[C@]4([H])[C@H](C)[C@@]6(O5)OC[C@@H](C)CC6)=O)[H] |
Show graphically |
Agave decipiens
(NCBI TaxID 2695036,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: leaf
The structure was elucidated in this paperPublication DOI: 10.1016/S0367-326X(99)00057-XJournal NLM ID: 16930290RPublisher: Elsevier
Institutions: Laboratory of Medicinal Chemistry, Theodor Bilharz Research Institute, Giza, Egypt
GLC analysis of the petrol extract of the leaves of Agave decipiens revealed that n-hexacosane was the main hydrocarbon, β-sitosterol the main sterol and oleic acid the main fatty acid. Two spirostanol and two furostanol saponins have been isolated from the methanolic extract. The structures of these saponins were established as 3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranosyl-26-O-β-D-glucopyranosyl-22α-methoxy-(25R)-furost-5-ene-3β,26-diol (1), neoruscogenin 1-O-β-D-glucopyranosyl-(1→3)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (2), 1-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranosyl-26-O-β-D-glucopyranosyl-22-methylfurosta-5,25(27)-diene-1β,3β,22,26-tetraol (3) and neohecogenin 3-O-β-D-glucopyranosyl-(1→3)-[β-D-xylopyranosyl-(1→3)-β-D-xylopyranosyl-(1→2)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (4). Saponins 2 and 4 showed high molluscicidal activity against B. alexandrina snails (LC90 = 13 and 6 ppm, respectively), whereas saponins 1 and 3 were inactive up to 50 ppm.
fatty acids, steroidal saponins, sterols, molluscicidal activity, Agave decipiens, hydrocarbons
Structure type: oligomer ; 1181.9 [M+H]+
Location inside paper: compound 4, p. 373 (compound 4), table 1(4), table 2(4)
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_114701,IEDB_136044,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_153543,IEDB_167188,IEDB_174332,IEDB_190606,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
Methods: 13C NMR, 1H NMR, IR, TLC, GLC, CI-MS, methylation analysis, PTLC, HCl hydrolysis, molluscicidal assay
Biological activity: Compound 4 had strong molluscicidal activity against B. alexandrina snails with LC90 of 6 ppm within 24 h.
Comments, role: NMR temperature was not specified
Related record ID(s): 62856, 62857, 62858
NCBI Taxonomy refs (TaxIDs): 2695036
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
3,4,2,3 bDXylp 104.31 75.20 78.10 71.60 67.20
3,4,2 bDXylp 105.50 75.10 76.50 70.90 66.60
3,4,3 bDGlcp 102.30 75.20 77.10 70.90 76.80 62.10
3,4 bDGlcp 101.50 81.10 83.50 70.90 76.00 76.00
3 bDGalp 100.50 72.50 75.30 79.60 75.00 60.30
Subst 37.2 31.5 76.08 37.7 44.7 28.3 31.3 31.9 55.5 36.7 37.2 ? 55.5 55.8 31.7 79.2 52.9 16.02 18.12 42.4 13.4 108.6 26.3 25.5 26.9 65.8 16.02
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
3,4,2,3 bDXylp
3,4,2 bDXylp
3,4,3 bDGlcp
3,4 bDGlcp
3 bDGalp 4.47 ? ? ? ? ?
Subst ? ? ? ? ? ? ? ? ? - ? - - ? ? ? ? 1.01 0.75 - 1.25 ? ? ? ? ? 0.95
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
3,4,2,3 bDXylp NMR TSV error 2: unequal length of 13C and 1H datasets
3,4,2 bDXylp NMR TSV error 2: unequal length of 13C and 1H datasets
3,4,3 bDGlcp NMR TSV error 2: unequal length of 13C and 1H datasets
3,4 bDGlcp NMR TSV error 2: unequal length of 13C and 1H datasets
3 bDGalp 100.50/4.47 72.50/? 75.30/? 79.60/? 75.00/? 60.30/?
Subst 37.2/? 31.5/? 76.08/? 37.7/? 44.7/? 28.3/? 31.3/? 31.9/? 55.5/? 37.2/? 55.8/? 31.7/? 79.2/? 52.9/? 16.02/1.01 18.12/0.75 13.4/1.25 108.6/? 26.3/? 25.5/? 26.9/? 65.8/? 16.02/0.95
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 |
|---|
| 3,4,2,3 | bDXylp | |
| 3,4,2 | bDXylp | |
| 3,4,3 | bDGlcp | |
| 3,4 | bDGlcp | |
| 3 | bDGalp | 4.47 | ? | ? | ? | ? | ? | |
| | Subst | ? | ? | ? | ? | ? | ? | ? | ? | ? |
| ? |
|
| ? | ? | ? | ? | 1.01 | 0.75 |
| 1.25 | ? | ? | ? | ? | ? | 0.95 |
|
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 |
|---|
| 3,4,2,3 | bDXylp | 104.31 | 75.20 | 78.10 | 71.60 | 67.20 | |
| 3,4,2 | bDXylp | 105.50 | 75.10 | 76.50 | 70.90 | 66.60 | |
| 3,4,3 | bDGlcp | 102.30 | 75.20 | 77.10 | 70.90 | 76.80 | 62.10 | |
| 3,4 | bDGlcp | 101.50 | 81.10 | 83.50 | 70.90 | 76.00 | 76.00 | |
| 3 | bDGalp | 100.50 | 72.50 | 75.30 | 79.60 | 75.00 | 60.30 | |
| | Subst | 37.2 | 31.5 | 76.08 | 37.7 | 44.7 | 28.3 | 31.3 | 31.9 | 55.5 | 36.7 | 37.2 | ? | 55.5 | 55.8 | 31.7 | 79.2 | 52.9 | 16.02 | 18.12 | 42.4 | 13.4 | 108.6 | 26.3 | 25.5 | 26.9 | 65.8 | 16.02 |
|
The spectrum also has 1 signal at unknown position (not plotted). |
There is only one chemically distinct structure:
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