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Parada F, Krajewski D, Duque C, Jäger E, Herderich M, Schreier P
1-O-β-D-glucopyranosyl anthranilate from piñuela (Bromelia plumieri) fruit
Phytochemistry 42(3) (1996)
871-873
Bromelia plumieri
(NCBI TaxID 4617,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: fruit
The structure was elucidated in this paperPublication DOI: 10.1016/0031-9422(95)00064-XJournal NLM ID: 0151434Publisher: Elsevier
Institutions: Departamento de Química, Universidad Nacional de Colombia, AA 14490, Bogotá, Colombia, Lehrstuhl für Lebensmittelchemie, Universität Würzburg, 97074 Würzburg, Germany
From the glycosidic extract of piñuela fruit; 1-O-β-D-glucopyranosyl anthranilate was isolated by adsorption chromatography on XAD-2, followed by rotation locular counter-current chromatography, multilayer coil counter-current chromatography and HPLC. Identification was carried out by NMR (1H, 13C, 1H-1H and 13C-1H COSY) and HPLC-MS/MS under electrospray ionization.
Electrospray Ionization, HPLC-MS/MS, Bromelia plumieri, Bromeliaceae, piñuela fruit, 1-O-β-D-glucopyranosyl anthranilate
Structure type: monomer ; 322.1 [M+Na]+
C
13H
17NO
7Location inside paper: compound 1, table 1(1), table 2(1), table 3
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, GC-MS, ESI-MS, HPLC, acetylation, COSY, hydrolysis, MLCCC, RLCC
Comments, role: NMR temperature was not specified
Related record ID(s): 63391
NCBI Taxonomy refs (TaxIDs): 4617
Show glycosyltransferases
NMR conditions: in CD3OD
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7
7 bDGlcp 95.4 73.9 78.0 71.0 78.7 62.3
xX2NBz 110.2 153.2 118.0 135.6 116.5 132.3 168.0
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7
7 bDGlcp 5.64 3.40-3.55 3.40-3.55 3.40-3.55 3.40-3.55 3.64-3.79
xX2NBz - - 6.67 7.18 6.50 7.83 -
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7
7 bDGlcp 95.4/5.64 73.9/3.40-3.55 78.0/3.40-3.55 71.0/3.40-3.55 78.7/3.40-3.55 62.3/3.64-3.79
xX2NBz 118.0/6.67 135.6/7.18 116.5/6.50 132.3/7.83
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 |
|---|
| 7 | bDGlcp | 5.64 | 3.40
3.55 | 3.40
3.55 | 3.40
3.55 | 3.40
3.55 | 3.64
3.79 | |
| | xX2NBz |
|
| 6.67 | 7.18 | 6.50 | 7.83 |
|
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 |
|---|
| 7 | bDGlcp | 95.4 | 73.9 | 78.0 | 71.0 | 78.7 | 62.3 | |
| | xX2NBz | 110.2 | 153.2 | 118.0 | 135.6 | 116.5 | 132.3 | 168.0 |
|
There is only one chemically distinct structure:
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Parada F, Krajewski D, Duque C, Jäger E, Herderich M, Schreier P
1-O-β-D-glucopyranosyl anthranilate from piñuela (Bromelia plumieri) fruit
Phytochemistry 42(3) (1996)
871-873
Bromelia plumieri
(NCBI TaxID 4617,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: fruit
The structure was elucidated in this paperPublication DOI: 10.1016/0031-9422(95)00064-XJournal NLM ID: 0151434Publisher: Elsevier
Institutions: Departamento de Química, Universidad Nacional de Colombia, AA 14490, Bogotá, Colombia, Lehrstuhl für Lebensmittelchemie, Universität Würzburg, 97074 Würzburg, Germany
From the glycosidic extract of piñuela fruit; 1-O-β-D-glucopyranosyl anthranilate was isolated by adsorption chromatography on XAD-2, followed by rotation locular counter-current chromatography, multilayer coil counter-current chromatography and HPLC. Identification was carried out by NMR (1H, 13C, 1H-1H and 13C-1H COSY) and HPLC-MS/MS under electrospray ionization.
Electrospray Ionization, HPLC-MS/MS, Bromelia plumieri, Bromeliaceae, piñuela fruit, 1-O-β-D-glucopyranosyl anthranilate
Structure type: monomer ; 532.3 [M+Na]+
C
23H
27NO
12Location inside paper: compound 2, table 1(2), table 2(2), table 4
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192,SB_61
Methods: 13C NMR, 1H NMR, GC-MS, ESI-MS, HPLC, acetylation, COSY, hydrolysis, MLCCC, RLCC
Synthetic data: chemical
Comments, role: NMR temperature was not specified; peracetated derivative of ID 63390
Related record ID(s): 63390
NCBI Taxonomy refs (TaxIDs): 4617
Show glycosyltransferases
NMR conditions: in CDCl3
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7
7,2 Ac 168.9-169.9 20.5-20.6
7,3 Ac 168.9-169.9 20.5-20.6
7,4 Ac 168.9-169.9 20.5-20.6
7,6 Ac 168.9-169.9 20.5-20.6
7 bDGlcp 92.4 70.1 72.6 68.0 72.9 61.5
2 Ac 170.4 25.4
xX2NBz 113.0 142.3 120.5 135.8 122.8 131.3 166.3
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7
7,2 Ac - 2.02-2.07
7,3 Ac - 2.02-2.07
7,4 Ac - 2.02-2.07
7,6 Ac - 2.02-2.07
7 bDGlcp 5.86 5.33 5.33 5.20 3.93 4.14-4.32
2 Ac - 2.23
xX2NBz - - 8.69 7.58 7.09 7.95 -
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7
7,2 Ac 20.5-20.6/2.02-2.07
7,3 Ac 20.5-20.6/2.02-2.07
7,4 Ac 20.5-20.6/2.02-2.07
7,6 Ac 20.5-20.6/2.02-2.07
7 bDGlcp 92.4/5.86 70.1/5.33 72.6/5.33 68.0/5.20 72.9/3.93 61.5/4.14-4.32
2 Ac 25.4/2.23
xX2NBz 120.5/8.69 135.8/7.58 122.8/7.09 131.3/7.95
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 |
|---|
| 7,2 | Ac |
| 2.02
2.07 | |
| 7,3 | Ac |
| 2.02
2.07 | |
| 7,4 | Ac |
| 2.02
2.07 | |
| 7,6 | Ac |
| 2.02
2.07 | |
| 7 | bDGlcp | 5.86 | 5.33 | 5.33 | 5.20 | 3.93 | 4.14
4.32 | |
| 2 | Ac |
| 2.23 | |
| | xX2NBz |
|
| 8.69 | 7.58 | 7.09 | 7.95 |
|
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 |
|---|
| 7,2 | Ac | 168.9
169.9 | 20.5
20.6 | |
| 7,3 | Ac | 168.9
169.9 | 20.5
20.6 | |
| 7,4 | Ac | 168.9
169.9 | 20.5
20.6 | |
| 7,6 | Ac | 168.9
169.9 | 20.5
20.6 | |
| 7 | bDGlcp | 92.4 | 70.1 | 72.6 | 68.0 | 72.9 | 61.5 | |
| 2 | Ac | 170.4 | 25.4 | |
| | xX2NBz | 113.0 | 142.3 | 120.5 | 135.8 | 122.8 | 131.3 | 166.3 |
|
There is only one chemically distinct structure:
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Krajewski D, Toth G, Schreier P
2-Ethyl-3-methylmaleimide N-β-D-glucopyranoside from the leaves of mangosteen (Garcinia mangostana)
Phytochemistry 43(1) (1996)
141-143
|
b-D-Glcp1N-(1-1)-Subst
Subst = 2-ethyl-3-methylmaleimide = SMILES CCC1=C(C(=O){1}NC1=O)C |
Show graphically |
Garcinia mangostana
(NCBI TaxID 58228,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: leaf
The structure was elucidated in this paperPublication DOI: 10.1016/0031-9422(96)00276-2Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Lehrstuhl für Lebensmittelchemie, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany, Technical and Analytical Research Group of the Hungarian Academy of Science, Institute for General and Analytical Chemistry, Technical University Budapest, 1111 Budapest, St. Gellért tér 4, Hungary
From a methanolic extract of leaves of Garcinia mangostana, 2-ethyl-3-methylmaleimide N-β-D-glucopyranoside was isolated by adsorption chromatography on XAD resin followed by rotation locular countercurrent chromatography. After acetylation, separation was performed by column chromatography on silica gel and preparative HPLC on RP-18 phase. Identification was carried out by mass spectrometry (DCI, APCI) and nuclear magnetic resonance (1H NMR, 13C NMR, 1H-1H COSY, HMQC). Assignment of the quateranry carbon resonances was achieved by HMBC experiments.
HMBC, guttiferae, Garcinia mangostana, mangosteen leaves, 2-ethyl-3-methylmaleimide, N-β-D-glucopyranoside, 3-ethyl-4-methyl-1H-pyrrole-2, 5-dione, APCIMS
Structure type: monomer
Location inside paper: 2-ethyl-3-methylmaleimide N-β-D-glucopyranoside
Compound class: glycoside
Methods: 13C NMR, 1H NMR, GC-MS, TLC, HPLC, UV, CID-MS, acetylation, HMBC, HMQC, COSY, DCI-MS, HPLC-APCI-MS, RLCC
Related record ID(s): 64067
NCBI Taxonomy refs (TaxIDs): 58228
Show glycosyltransferases
There is only one chemically distinct structure:
Expand this record
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Krajewski D, Toth G, Schreier P
2-Ethyl-3-methylmaleimide N-β-D-glucopyranoside from the leaves of mangosteen (Garcinia mangostana)
Phytochemistry 43(1) (1996)
141-143
|
b-D-Glcp1N2Ac3Ac4Ac6Ac-(1-1)-Subst
Subst = 2-ethyl-3-methylmaleimide = SMILES CCC1=C(C(=O){1}NC1=O)C |
Show graphically |
Garcinia mangostana
(NCBI TaxID 58228,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: leaf
The structure was elucidated in this paperPublication DOI: 10.1016/0031-9422(96)00276-2Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Lehrstuhl für Lebensmittelchemie, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany, Technical and Analytical Research Group of the Hungarian Academy of Science, Institute for General and Analytical Chemistry, Technical University Budapest, 1111 Budapest, St. Gellért tér 4, Hungary
From a methanolic extract of leaves of Garcinia mangostana, 2-ethyl-3-methylmaleimide N-β-D-glucopyranoside was isolated by adsorption chromatography on XAD resin followed by rotation locular countercurrent chromatography. After acetylation, separation was performed by column chromatography on silica gel and preparative HPLC on RP-18 phase. Identification was carried out by mass spectrometry (DCI, APCI) and nuclear magnetic resonance (1H NMR, 13C NMR, 1H-1H COSY, HMQC). Assignment of the quateranry carbon resonances was achieved by HMBC experiments.
HMBC, guttiferae, Garcinia mangostana, mangosteen leaves, 2-ethyl-3-methylmaleimide, N-β-D-glucopyranoside, 3-ethyl-4-methyl-1H-pyrrole-2, 5-dione, APCIMS
Structure type: monomer ; 470 [M+H]+
C
21H
27NO
1l
Location inside paper: compound 1, table 1, table 2
Compound class: glycoside
Methods: 13C NMR, 1H NMR, GC-MS, TLC, HPLC, UV, CID-MS, acetylation, HMBC, HMQC, COSY, DCI-MS, HPLC-APCI-MS, RLCC
Synthetic data: chemical
Comments, role: peracetylated derivetive of ID 64066; NMR temperature was not specified
Related record ID(s): 64066
NCBI Taxonomy refs (TaxIDs): 58228
Show glycosyltransferases
NMR conditions: in CDCl3
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7
1,2 Ac 168.9 20.4
1,3 Ac 170.1 20.6
1,4 Ac 169.3 20.6
1,6 Ac 170.6 20.7
1 bDGlcp1N 77.6 68.1 73.7 67.9 74.5 61.8
Subst 169.6 143.0 137.4 170.1 17.2 12.4 8.6
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7
1,2 Ac - 1.93
1,3 Ac - 2.02
1,4 Ac - 2.04
1,6 Ac - 2.08
1 bDGlcp1N 5.20 5.92 5.27 5.20 3.78 4.17-4.19
Subst - - - - 2.41 1.14 1.97
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7
1,2 Ac 20.4/1.93
1,3 Ac 20.6/2.02
1,4 Ac 20.6/2.04
1,6 Ac 20.7/2.08
1 bDGlcp1N 77.6/5.20 68.1/5.92 73.7/5.27 67.9/5.20 74.5/3.78 61.8/4.17-4.19
Subst 17.2/2.41 12.4/1.14 8.6/1.97
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 |
|---|
| 1,2 | Ac |
| 1.93 | |
| 1,3 | Ac |
| 2.02 | |
| 1,4 | Ac |
| 2.04 | |
| 1,6 | Ac |
| 2.08 | |
| 1 | bDGlcp1N | 5.20 | 5.92 | 5.27 | 5.20 | 3.78 | 4.17
4.19 | |
| | Subst |
|
|
|
| 2.41 | 1.14 | 1.97 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 |
|---|
| 1,2 | Ac | 168.9 | 20.4 | |
| 1,3 | Ac | 170.1 | 20.6 | |
| 1,4 | Ac | 169.3 | 20.6 | |
| 1,6 | Ac | 170.6 | 20.7 | |
| 1 | bDGlcp1N | 77.6 | 68.1 | 73.7 | 67.9 | 74.5 | 61.8 | |
| | Subst | 169.6 | 143.0 | 137.4 | 170.1 | 17.2 | 12.4 | 8.6 |
|
There is only one chemically distinct structure:
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