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Alvarez L, Delgado G
C- and O-glycosyl-α-hydroxydihydrochalcones from Eysenhardtia polystachya
Phytochemistry 50(4) (1999)
681-687
|
b-D-1dXylp-(1C-3')-Subst
Subst = (αR)-α,3,4,2',4'-pentahydroxydihydrochalcone = SMILES O=C(c1cc{54}c(O){53}c{52}c1O){1}[C@H](O)Cc2cc{3}c(O){4}c(O)c2 |
Show graphically |
Eysenhardtia polystachya
(NCBI TaxID 457900,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: bark,
trunk
The structure was elucidated in this paperPublication DOI: 10.1016/S0031-9422(98)00576-7Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Centro de Investigaciones Quı́micas de la Universidad Autónoma del Estado de Morelos, Avenida Universidad 1001, Cuernavaca 62210, Morelos, Mexico, Instituto de Quı́mica de la Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Coyoacán, 04510, Mexico
Three new α-hydroxydihydrochalcones, (αR)-α,3,4,2',4'-pentahydroxydihydrochalcone, (αR)-3'-C-β-D-xylopyranosyl-α,3,4,2',4'-pentahydroxydihydrochalcone, and (αR)-3'-O-β-D-xylopyranosyl-α,3,4,2',4'-pentahydroxydihydrochalcone, together with the known coatline B [(αR)-3'-C-β-D-glucopyranosyl-α,2',3,4',4-pentahydroxydihydrochalcone], were isolated from the bark and trunks of Eysenhardtia polystachya and their structures were deduced by spectral methods. One of the isolates displayed insecticidal activity.
insecticidal activity, Leguminosae, Eysenhardtia polystachya, C- and O-glycosyl α-hydroxydihydrochalcones
Structure type: monomer
C
20H
22O
10Location inside paper: compound 2, p. 682 (fig., 2), table 1(2), table 2(2)
Compound class: phenolic glycoside
Methods: 13C NMR, 1H NMR, IR, UV, EI-MS, acetylation, CD, RP-HPLC, TCL, cytotoxicity assay, HMBC, HMQC, DEPT, antimicrobial assay, COSY, NOESY, HCl hydrolysis, HETCOR, insecticidal activity
Comments, role: NMR temperature was not specified
Related record ID(s): 64100, 64101, 64102
NCBI Taxonomy refs (TaxIDs): 457900
Show glycosyltransferases
NMR conditions: in CDCl3 / DMSO-d6
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15
3' bD1dXylp 73.98 70.47 78.44 69.20 69.65
Subst 203.25 72.34 40.57 127.65 114.57 143.76 142.79 115.88 119.75 110.75 163.30 109.74 163.10 107.92 130.71
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15
3' bD1dXylp 4.81 4.06 3.46 3.69 3.32-4.02
Subst - 5.05 2.77-2.96 - 6.65 - - 6.69 6.52 - - - 6.45 - 7.62
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
3' bD1dXylp 73.98/4.81 70.47/4.06 78.44/3.46 69.20/3.69 69.65/3.32-4.02
Subst 72.34/5.05 40.57/2.77-2.96 114.57/6.65 115.88/6.69 119.75/6.52 163.10/6.45 130.71/7.62
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 |
|---|
| 3' | bD1dXylp | 4.81 | 4.06 | 3.46 | 3.69 | 3.32
4.02 | |
| | Subst |
| 5.05 | 2.77
2.96 |
| 6.65 |
|
| 6.69 | 6.52 |
|
|
| 6.45 |
| 7.62 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 |
|---|
| 3' | bD1dXylp | 73.98 | 70.47 | 78.44 | 69.20 | 69.65 | |
| | Subst | 203.25 | 72.34 | 40.57 | 127.65 | 114.57 | 143.76 | 142.79 | 115.88 | 119.75 | 110.75 | 163.30 | 109.74 | 163.10 | 107.92 | 130.71 |
|
There is only one chemically distinct structure:
Expand this record
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Alvarez L, Delgado G
C- and O-glycosyl-α-hydroxydihydrochalcones from Eysenhardtia polystachya
Phytochemistry 50(4) (1999)
681-687
|
b-D-1dXylp2Ac3Ac4Ac-(1C-3')-Subst1Ac3Ac4Ac2'Ac4'Ac
Subst = (αR)-α,3,4,2',4'-pentahydroxydihydrochalcone = SMILES O=C(c1cc{54}c(O){53}c{52}c1O){1}[C@H](O)Cc2cc{3}c(O){4}c(O)c2 |
Show graphically |
Eysenhardtia polystachya
(NCBI TaxID 457900,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: bark,
trunk
The structure was elucidated in this paperPublication DOI: 10.1016/S0031-9422(98)00576-7Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Centro de Investigaciones Quı́micas de la Universidad Autónoma del Estado de Morelos, Avenida Universidad 1001, Cuernavaca 62210, Morelos, Mexico, Instituto de Quı́mica de la Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Coyoacán, 04510, Mexico
Three new α-hydroxydihydrochalcones, (αR)-α,3,4,2',4'-pentahydroxydihydrochalcone, (αR)-3'-C-β-D-xylopyranosyl-α,3,4,2',4'-pentahydroxydihydrochalcone, and (αR)-3'-O-β-D-xylopyranosyl-α,3,4,2',4'-pentahydroxydihydrochalcone, together with the known coatline B [(αR)-3'-C-β-D-glucopyranosyl-α,2',3,4',4-pentahydroxydihydrochalcone], were isolated from the bark and trunks of Eysenhardtia polystachya and their structures were deduced by spectral methods. One of the isolates displayed insecticidal activity.
insecticidal activity, Leguminosae, Eysenhardtia polystachya, C- and O-glycosyl α-hydroxydihydrochalcones
Structure type: monomer
Location inside paper: compound 2a, p. 682 (fig., 2a), table 1(2a), table 2(2a)
Compound class: phenolic glycoside
Methods: 13C NMR, 1H NMR, IR, UV, EI-MS, acetylation, CD, RP-HPLC, TCL, cytotoxicity assay, HMBC, HMQC, DEPT, antimicrobial assay, COSY, NOESY, HCl hydrolysis, HETCOR, insecticidal activity
Synthetic data: chemical
Comments, role: NMR temperature was not specified; peracetated derivative of ID 64099
Related record ID(s): 64099, 64101, 64102
NCBI Taxonomy refs (TaxIDs): 457900
Show glycosyltransferases
NMR conditions: in CDCl3 / DMSO-d6
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15
3',2 Ac
3',3 Ac
3',4 Ac
3' bD1dXylp 70.66 74.20 74.44 69.09 67.58
1 Ac
3 Ac
4 Ac
2' Ac
4' Ac
Subst 198.52 70.38 37.26 127.28 123.50 142.01 141.21 110.21 124.45 108.74 163.11 134.60 164.04 108.74 131.77
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15
3',2 Ac
3',3 Ac
3',4 Ac
3' bD1dXylp 5.17 5.41 5.27 5.12 3.51-4.34
1 Ac
3 Ac
4 Ac
2' Ac
4' Ac
Subst - 5.85 3.11 - 7.10 - - 7.10 7.10 - - - 6.45 - 7.59
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
3',2 Ac
3',3 Ac
3',4 Ac
3' bD1dXylp 70.66/5.17 74.20/5.41 74.44/5.27 69.09/5.12 67.58/3.51-4.34
1 Ac
3 Ac
4 Ac
2' Ac
4' Ac
Subst 70.38/5.85 37.26/3.11 123.50/7.10 110.21/7.10 124.45/7.10 164.04/6.45 131.77/7.59
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 |
|---|
| 3',2 | Ac | |
| 3',3 | Ac | |
| 3',4 | Ac | |
| 3' | bD1dXylp | 5.17 | 5.41 | 5.27 | 5.12 | 3.51
4.34 | |
| 1 | Ac | |
| 3 | Ac | |
| 4 | Ac | |
| 2' | Ac | |
| 4' | Ac | |
| | Subst |
| 5.85 | 3.11 |
| 7.10 |
|
| 7.10 | 7.10 |
|
|
| 6.45 |
| 7.59 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 |
|---|
| 3',2 | Ac | |
| 3',3 | Ac | |
| 3',4 | Ac | |
| 3' | bD1dXylp | 70.66 | 74.20 | 74.44 | 69.09 | 67.58 | |
| 1 | Ac | |
| 3 | Ac | |
| 4 | Ac | |
| 2' | Ac | |
| 4' | Ac | |
| | Subst | 198.52 | 70.38 | 37.26 | 127.28 | 123.50 | 142.01 | 141.21 | 110.21 | 124.45 | 108.74 | 163.11 | 134.60 | 164.04 | 108.74 | 131.77 |
|
There is only one chemically distinct structure:
Expand this record
Collapse this record
Alvarez L, Delgado G
C- and O-glycosyl-α-hydroxydihydrochalcones from Eysenhardtia polystachya
Phytochemistry 50(4) (1999)
681-687
|
b-D-Xylp-(1-3')-Subst
Subst = (αR)-α,3,4,2',3',4'-hexahydroxydihydrochalcone = SMILES O=C(c1cc{54}c(O){53}c(O){52}c1O){1}[C@H](O)Cc2cc{3}c(O){4}c(O)c2 |
Show graphically |
Eysenhardtia polystachya
(NCBI TaxID 457900,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: bark,
trunk
The structure was elucidated in this paperPublication DOI: 10.1016/S0031-9422(98)00576-7Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Centro de Investigaciones Quı́micas de la Universidad Autónoma del Estado de Morelos, Avenida Universidad 1001, Cuernavaca 62210, Morelos, Mexico, Instituto de Quı́mica de la Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Coyoacán, 04510, Mexico
Three new α-hydroxydihydrochalcones, (αR)-α,3,4,2',4'-pentahydroxydihydrochalcone, (αR)-3'-C-β-D-xylopyranosyl-α,3,4,2',4'-pentahydroxydihydrochalcone, and (αR)-3'-O-β-D-xylopyranosyl-α,3,4,2',4'-pentahydroxydihydrochalcone, together with the known coatline B [(αR)-3'-C-β-D-glucopyranosyl-α,2',3,4',4-pentahydroxydihydrochalcone], were isolated from the bark and trunks of Eysenhardtia polystachya and their structures were deduced by spectral methods. One of the isolates displayed insecticidal activity.
insecticidal activity, Leguminosae, Eysenhardtia polystachya, C- and O-glycosyl α-hydroxydihydrochalcones
Structure type: monomer
C
20H
22O
11Location inside paper: compound 3, p. 682 (fig., 3), table 1(3), table 2(3)
Compound class: phenolic glycoside
Contained glycoepitopes: IEDB_114701,IEDB_167188,IEDB_174332
Methods: 13C NMR, 1H NMR, IR, UV, EI-MS, acetylation, CD, RP-HPLC, TCL, cytotoxicity assay, HMBC, HMQC, DEPT, antimicrobial assay, COSY, NOESY, HCl hydrolysis, HETCOR, insecticidal activity
Biological activity: Compound 3 demonstrated insecticidal activity against Epilachna varivestis larvae with LC100 < 100 ng/cm2.
Comments, role: NMR temperature was not specified
Related record ID(s): 64099, 64100, 64102
NCBI Taxonomy refs (TaxIDs): 457900
Show glycosyltransferases
NMR conditions: in CDCl3 / DMSO-d6
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15
3' bDXylp 114.82 73.97 79.23 70.25 69.96
Subst 204.76 72.89 40.74 128.62 115.23 144.75 143.59 116.87 120.02 112.23 164.58 110.27 163.92 107.97 131.91
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15
3' bDXylp 4.74 4.11 3.37 3.63 3.27-3.96
Subst - 5.01 2.74-2.93 - 6.68 - - 6.67 6.51 - - - 6.45 - 7.66
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
3' bDXylp 114.82/4.74 73.97/4.11 79.23/3.37 70.25/3.63 69.96/3.27-3.96
Subst 72.89/5.01 40.74/2.74-2.93 115.23/6.68 116.87/6.67 120.02/6.51 163.92/6.45 131.91/7.66
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 |
|---|
| 3' | bDXylp | 4.74 | 4.11 | 3.37 | 3.63 | 3.27
3.96 | |
| | Subst |
| 5.01 | 2.74
2.93 |
| 6.68 |
|
| 6.67 | 6.51 |
|
|
| 6.45 |
| 7.66 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 |
|---|
| 3' | bDXylp | 114.82 | 73.97 | 79.23 | 70.25 | 69.96 | |
| | Subst | 204.76 | 72.89 | 40.74 | 128.62 | 115.23 | 144.75 | 143.59 | 116.87 | 120.02 | 112.23 | 164.58 | 110.27 | 163.92 | 107.97 | 131.91 |
|
There is only one chemically distinct structure:
Expand this record
Collapse this record
Alvarez L, Delgado G
C- and O-glycosyl-α-hydroxydihydrochalcones from Eysenhardtia polystachya
Phytochemistry 50(4) (1999)
681-687
|
b-D-1dGlcp-(1C-3')-Subst
Subst = (αR)-α,3,4,2',4'-pentahydroxydihydrochalcone = SMILES O=C(c1cc{54}c(O){53}c{52}c1O){1}[C@H](O)Cc2cc{3}c(O){4}c(O)c2 |
Show graphically |
Eysenhardtia polystachya
(NCBI TaxID 457900,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: bark,
trunk
The structure was elucidated in this paperPublication DOI: 10.1016/S0031-9422(98)00576-7Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Centro de Investigaciones Quı́micas de la Universidad Autónoma del Estado de Morelos, Avenida Universidad 1001, Cuernavaca 62210, Morelos, Mexico, Instituto de Quı́mica de la Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Coyoacán, 04510, Mexico
Three new α-hydroxydihydrochalcones, (αR)-α,3,4,2',4'-pentahydroxydihydrochalcone, (αR)-3'-C-β-D-xylopyranosyl-α,3,4,2',4'-pentahydroxydihydrochalcone, and (αR)-3'-O-β-D-xylopyranosyl-α,3,4,2',4'-pentahydroxydihydrochalcone, together with the known coatline B [(αR)-3'-C-β-D-glucopyranosyl-α,2',3,4',4-pentahydroxydihydrochalcone], were isolated from the bark and trunks of Eysenhardtia polystachya and their structures were deduced by spectral methods. One of the isolates displayed insecticidal activity.
insecticidal activity, Leguminosae, Eysenhardtia polystachya, C- and O-glycosyl α-hydroxydihydrochalcones
Structure type: monomer ; 452
C
21H
24O
11Location inside paper: compound 4, p. 682 (fig., 4), table 1(4), table 2(4)
Compound class: phenolic glycoside
Methods: 13C NMR, 1H NMR, IR, UV, EI-MS, acetylation, CD, RP-HPLC, TCL, cytotoxicity assay, HMBC, HMQC, DEPT, antimicrobial assay, COSY, NOESY, HCl hydrolysis, HETCOR, insecticidal activity
Comments, role: NMR temperature was not specified
Related record ID(s): 64099, 64100, 64101
NCBI Taxonomy refs (TaxIDs): 457900
Show glycosyltransferases
NMR conditions: in CDCl3 / DMSO-d6
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15
3' bD1dGlcp 73.55 71.10 78.38 69.77 80.57 60.83
Subst 204.08 73.11 40.47 128.29 116.53 144.43 143.37 115.13 120.05 110.41 163.50 111.73 163.73 108.40 131.36
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15
3' bD1dGlcp 4.63 3.95 3.66 3.45 3.20 3.80
Subst - 4.93 2.64-2.84 - 6.59 - - 6.57 6.43 - - - 6.39 - 7.62
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
3' bD1dGlcp 73.55/4.63 71.10/3.95 78.38/3.66 69.77/3.45 80.57/3.20 60.83/3.80
Subst 73.11/4.93 40.47/2.64-2.84 116.53/6.59 115.13/6.57 120.05/6.43 163.73/6.39 131.36/7.62
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 |
|---|
| 3' | bD1dGlcp | 4.63 | 3.95 | 3.66 | 3.45 | 3.20 | 3.80 | |
| | Subst |
| 4.93 | 2.64
2.84 |
| 6.59 |
|
| 6.57 | 6.43 |
|
|
| 6.39 |
| 7.62 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 |
|---|
| 3' | bD1dGlcp | 73.55 | 71.10 | 78.38 | 69.77 | 80.57 | 60.83 | |
| | Subst | 204.08 | 73.11 | 40.47 | 128.29 | 116.53 | 144.43 | 143.37 | 115.13 | 120.05 | 110.41 | 163.50 | 111.73 | 163.73 | 108.40 | 131.36 |
|
There is only one chemically distinct structure:
Expand this record
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Total list of record IDs on all result pages of the current query:
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