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Duroux L, Delmotte FM, Lancelin JM, Keravis G
Insight into naphthoquinone metabolism: β-glucosidase-catalysed hydrolysis of hydrojuglone β-D-glucopyranoside
Journal of Applied Polymer Science 333 (1998)
275-283
|
b-D-Glcp-(1-4)-Subst
Subst = naphthalene-1,4,5-triol = SMILES O{1}c1cc{4}c(O)c2c1ccc{5}c2O |
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Juglans regia
(NCBI TaxID 51240,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
The structure was elucidated in this paperPublication DOI: 10.1042/bj3330275Journal NLM ID: 9891577Publisher: Wiley
Institutions: Station d'Amélioration des Arbres Forestiers, I.N.R.A.-Orléans, Ardon, France, Glycobiologie, Centre de Biophysique Moléculaire, C.N.R.S.-Université d'Orleéans, Orléans, France, Laboratoire de RMN Biomoléculaire, Université Claude Bernard, Villeurbane, France, Laboratoire de Biologie des Ligneux, Université d'Orléans, Orle!ans, France
In plants, the naphthoquinone juglone is known to be involved in pathogenic defence mechanisms, but it may also take part in plant developmental processes. This naphthoquinone can accumulate in a glycosylated form, namely hydrojuglone beta-D-glucopyranoside. The structural configuration of this compound was shown to be 1,5-dihydroxy-4-naphthalenyl-beta-D-glucopyranoside by means of MS, NMR and nuclear Overhauser effect spectroscopy analyses. A hydrojuglone beta-D-glucopyranoside beta-glucosidase (EC 3.2.1.21) was purified to homogeneity from Juglans regia L. The enzyme catalysed the release of juglone from hydrojuglone beta-D-glucopyranoside with high specificity and showed Michaelis-Menten kinetics with K-m = 0.62 mM and V-max = 14.5 mu kat/mg of protein. This enzyme also showed a higher activity towards beta-D-fucosyl than beta-D-glucosyl bonds. The purified enzyme had an apparent M-r of 64000 by SDS/PAGE and a pI 8.9 by isoelectrofocusing PAGE. The purified enzyme was inhibited by several bivalent cations, such as Cu2+, Fe2+, Hg2+, and by D-glucono-1,5-lactone, showing non-competitive inhibition of the mixed type.
biosynthesis, specificity, purification, Plants, oxidase, dalbergia-cochinchinensis-pierre, fucosidase activities, cell-cultures, juglone, walnut
Structure type: monomer ; 339 [M+H]+
Location inside paper: Fig. 2, HJG, table 1
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 1H NMR, EI-MS, enzymatic hydrolysis, HPLC, extraction, DQF-COSY, CIMS
Enzymes that release or process the structure: WBG8.9
NCBI Taxonomy refs (TaxIDs): 51240
Show glycosyltransferases
NMR conditions: in DMSO-d6 at 298(H) K
[as TSV]
13C NMR data:
missing...
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10
4 bDGlcp 4.50 3.32 3.30 3.17 3.36 3.78
Subst - 6.71 7.20 - - - 7.57 7.29 ? -
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 |
|---|
| 4 | bDGlcp | 4.50 | 3.32 | 3.30 | 3.17 | 3.36 | 3.78 | |
| | Subst |
| 6.71 | 7.20 |
|
|
| 7.57 | 7.29 | ? |
|
|
There is only one chemically distinct structure:
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Athayde ML, Schenkel EP, Gosmann G, Guillaume D
Triterpenoids from the leaves of Ilex theezans Martius ex Reiss.
Acta Farmacéutica Bonaerense = Buenos Aires Pharmaceutical Acta [Spanish] 18(1) (1999)
49-52
|
b-D-Glcp-(1-28)-Subst
Subst = rotundic acid = SMILES C[C@@H]1CC[C@]2({28}C(O)=O)CC[C@]3(C)C([C@@H]2{19}[C@@]1(O)C)=CC[C@H]4[C@@]3(C)CC[C@@H]5[C@]4(C)CC{3}[C@H](O)[C@]5({23}CO)C |
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Ilex theizans
(previously named: Ilex theezans)
(NCBI TaxID 185555,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: leaf
The structure was elucidated in this paperJournal NLM ID: 8711484WWW link: http://www.latamjpharm.org/trabajos/18/1/LAJOP_18_1_1_8_RR5LBM80W1.pdfPublisher: Colegio de Farmaceuticos de la Provincia de Buenos Aires
Correspondence: Schenkel EP <Schenkel
farmacia.ufrgs.br>
Institutions: Faculdade de Farmácia, UFRGS, Av. Ipiranga, 2752,90610-000 Porto Alegre, RS, Brazil, Laboratoire de Chimie Thérapeutique, URA 1310 du CNRS, Faculté des Sciences Pharmaceutiques et Biologiques, Paris V, France
From Ilex theezans leaves, a species reported as adulterant of the genuine erva-mate (Ilex paraguariensis St. Hil.), two saponins and one triterpene have been isolated. Their structures were elucidated by mean of spectroscopic methods. The saponins were identified as the 28-O-β-D-glucopyranosylester of rotundic acid (pedunculoside) and the 28-O-β-D-glucopyranosylester of rotundioic acid. The triterpene was identified as rotundic acid.
saponins, Aquifoliaceae, rotundic acid, Ilex theezans, pedunculoside, rotundioic acid
Structure type: monomer ; 651 [M+H]+
C
36H
58O
10Location inside paper: compound 1, figure 1(1), table 1(1)
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, EI-MS, FAB-MS, TLC, acid hydrolysis, alkaline hydrolysis, optical rotation measurement, acetylation, CIMS
Comments, role: NMR temperature was not specified
Related record ID(s): 62222, 62223, 120105
NCBI Taxonomy refs (TaxIDs): 185555
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
28 bDGlcp 95.8 73.9 78.8 71.3 79.1 62.4
Subst 38.9 27.0 73.8 42.8 48.7 18.8 33.2 40.6 47.8 37.2 24.1 128.4 139.3 42.1 29.2 26.7 48.6 54.4 72.7 42.1 26.1 37.7 68.2 13.0 17.5 16.6 24.5 177.1 27.5 15.1
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
28 bDGlcp 6.25 ? ? ? ? ?
Subst ? ? ? - ? ? ? - ? - ? ? - - ? ? - 2.95 - ? ? ? ? 1.04-1.62 1.04-1.62 1.04-1.62 1.04-1.62 - 1.04-1.62 1.06
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
28 bDGlcp 95.8/6.25 73.9/? 78.8/? 71.3/? 79.1/? 62.4/?
Subst 38.9/? 27.0/? 73.8/? 48.7/? 18.8/? 33.2/? 47.8/? 24.1/? 128.4/? 29.2/? 26.7/? 54.4/2.95 42.1/? 26.1/? 37.7/? 68.2/? 13.0/1.04-1.62 17.5/1.04-1.62 16.6/1.04-1.62 24.5/1.04-1.62 27.5/1.04-1.62 15.1/1.06
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 |
|---|
| 28 | bDGlcp | 6.25 | ? | ? | ? | ? | ? | |
| | Subst | ? | ? | ? |
| ? | ? | ? |
| ? |
| ? | ? |
|
| ? | ? |
| 2.95 |
| ? | ? | ? | ? | 1.04
1.62 | 1.04
1.62 | 1.04
1.62 | 1.04
1.62 |
| 1.04
1.62 | 1.06 |
|
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 |
|---|
| 28 | bDGlcp | 95.8 | 73.9 | 78.8 | 71.3 | 79.1 | 62.4 | |
| | Subst | 38.9 | 27.0 | 73.8 | 42.8 | 48.7 | 18.8 | 33.2 | 40.6 | 47.8 | 37.2 | 24.1 | 128.4 | 139.3 | 42.1 | 29.2 | 26.7 | 48.6 | 54.4 | 72.7 | 42.1 | 26.1 | 37.7 | 68.2 | 13.0 | 17.5 | 16.6 | 24.5 | 177.1 | 27.5 | 15.1 |
|
There is only one chemically distinct structure:
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Athayde ML, Schenkel EP, Gosmann G, Guillaume D
Triterpenoids from the leaves of Ilex theezans Martius ex Reiss.
Acta Farmacéutica Bonaerense = Buenos Aires Pharmaceutical Acta [Spanish] 18(1) (1999)
49-52
|
b-D-Glcp-(1-28)-Subst
Subst = rotundioic acid = SMILES C[C@@H]1CC[C@@]2(CC[C@@]3(C([C@@H]2{19}[C@@]1(O)C)=CC[C@@H]4[C@]5(CC{3}[C@@H]([C@@]({23}C(O)=O)([C@@H]5CC[C@]43C)C)O)C)C){28}C(O)=O |
Show graphically |
Ilex theizans
(previously named: Ilex theezans)
(NCBI TaxID 185555,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: leaf
The structure was elucidated in this paperJournal NLM ID: 8711484WWW link: http://www.latamjpharm.org/trabajos/18/1/LAJOP_18_1_1_8_RR5LBM80W1.pdfPublisher: Colegio de Farmaceuticos de la Provincia de Buenos Aires
Correspondence: Schenkel EP <Schenkel
farmacia.ufrgs.br>
Institutions: Faculdade de Farmácia, UFRGS, Av. Ipiranga, 2752,90610-000 Porto Alegre, RS, Brazil, Laboratoire de Chimie Thérapeutique, URA 1310 du CNRS, Faculté des Sciences Pharmaceutiques et Biologiques, Paris V, France
From Ilex theezans leaves, a species reported as adulterant of the genuine erva-mate (Ilex paraguariensis St. Hil.), two saponins and one triterpene have been isolated. Their structures were elucidated by mean of spectroscopic methods. The saponins were identified as the 28-O-β-D-glucopyranosylester of rotundic acid (pedunculoside) and the 28-O-β-D-glucopyranosylester of rotundioic acid. The triterpene was identified as rotundic acid.
saponins, Aquifoliaceae, rotundic acid, Ilex theezans, pedunculoside, rotundioic acid
Structure type: monomer ; 687 [M+Na]+
C
36H
58O
10Location inside paper: compound 2, figure 1(2)
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, EI-MS, FAB-MS, TLC, acid hydrolysis, alkaline hydrolysis, optical rotation measurement, acetylation, CIMS
Comments, role: NMR data is given only for ID 62223
Related record ID(s): 62221, 62223, 120105
NCBI Taxonomy refs (TaxIDs): 185555
Show glycosyltransferases
There is only one chemically distinct structure:
Expand this record
Collapse this record
Athayde ML, Schenkel EP, Gosmann G, Guillaume D
Triterpenoids from the leaves of Ilex theezans Martius ex Reiss.
Acta Farmacéutica Bonaerense = Buenos Aires Pharmaceutical Acta [Spanish] 18(1) (1999)
49-52
|
b-D-Glcp2Ac3Ac4Ac6Ac-(1-28)-Subst3Ac19Ac
Subst = rotundioic acid = SMILES C[C@@H]1CC[C@@]2(CC[C@@]3(C([C@@H]2{19}[C@@]1(O)C)=CC[C@@H]4[C@]5(CC{3}[C@@H]([C@@]({23}C(O)=O)([C@@H]5CC[C@]43C)C)O)C)C){28}C(O)=O |
Show graphically |
Ilex theizans
(previously named: Ilex theezans)
(NCBI TaxID 185555,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: leaf
The structure was elucidated in this paperJournal NLM ID: 8711484WWW link: http://www.latamjpharm.org/trabajos/18/1/LAJOP_18_1_1_8_RR5LBM80W1.pdfPublisher: Colegio de Farmaceuticos de la Provincia de Buenos Aires
Correspondence: Schenkel EP <Schenkel
farmacia.ufrgs.br>
Institutions: Faculdade de Farmácia, UFRGS, Av. Ipiranga, 2752,90610-000 Porto Alegre, RS, Brazil, Laboratoire de Chimie Thérapeutique, URA 1310 du CNRS, Faculté des Sciences Pharmaceutiques et Biologiques, Paris V, France
From Ilex theezans leaves, a species reported as adulterant of the genuine erva-mate (Ilex paraguariensis St. Hil.), two saponins and one triterpene have been isolated. Their structures were elucidated by mean of spectroscopic methods. The saponins were identified as the 28-O-β-D-glucopyranosylester of rotundic acid (pedunculoside) and the 28-O-β-D-glucopyranosylester of rotundioic acid. The triterpene was identified as rotundic acid.
saponins, Aquifoliaceae, rotundic acid, Ilex theezans, pedunculoside, rotundioic acid
Structure type: monomer
Location inside paper: compound 2a, p. 50 (compound 2a), table 1(2a)
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192,SB_61
Methods: 13C NMR, 1H NMR, EI-MS, FAB-MS, TLC, acid hydrolysis, alkaline hydrolysis, optical rotation measurement, acetylation, CIMS
Synthetic data: chemical
Comments, role: compound 2a is peracetylated derivative of ID 62222, NMR temperature was not specified
Related record ID(s): 62221, 62222, 120105
NCBI Taxonomy refs (TaxIDs): 185555
Show glycosyltransferases
NMR conditions: in CDCl3
[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
28,2 Ac
28,3 Ac
28,4 Ac
28,6 Ac
28 bDGlcp 91.5 69.7 72.7 67.8 72.3 61.4
3 Ac
19 Ac
Subst 37.7 25.7 77.0 51.6 50.5 22.8 32.4 40.0 47.0 36.5 23.9 128.7 137.3 40.9 28.1 23.5 47.7 52.8 72.9 40.9 25.1 36.2 180.2 11.5 15.5 15.9 24.0 175.6 27.2 16.6
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
28,2 Ac
28,3 Ac
28,4 Ac
28,6 Ac
28 bDGlcp 5.55 ? ? ? ? ?
3 Ac
19 Ac
Subst ? ? ? - ? ? ? - ? - ? 5.41 - - ? ? - 2.54 - ? ? ? - 0.74-1.28 0.74-1.28 0.74-1.28 0.74-1.28 - 0.74-1.28 1.23
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
28,2 Ac
28,3 Ac
28,4 Ac
28,6 Ac
28 bDGlcp 91.5/5.55 69.7/? 72.7/? 67.8/? 72.3/? 61.4/?
3 Ac
19 Ac
Subst 37.7/? 25.7/? 77.0/? 50.5/? 22.8/? 32.4/? 47.0/? 23.9/? 128.7/5.41 28.1/? 23.5/? 52.8/2.54 40.9/? 25.1/? 36.2/? 11.5/0.74-1.28 15.5/0.74-1.28 15.9/0.74-1.28 24.0/0.74-1.28 27.2/0.74-1.28 16.6/1.23
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 |
|---|
| 28,2 | Ac | |
| 28,3 | Ac | |
| 28,4 | Ac | |
| 28,6 | Ac | |
| 28 | bDGlcp | 5.55 | ? | ? | ? | ? | ? | |
| 3 | Ac | |
| 19 | Ac | |
| | Subst | ? | ? | ? |
| ? | ? | ? |
| ? |
| ? | 5.41 |
|
| ? | ? |
| 2.54 |
| ? | ? | ? |
| 0.74
1.28 | 0.74
1.28 | 0.74
1.28 | 0.74
1.28 |
| 0.74
1.28 | 1.23 |
|
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 |
|---|
| 28,2 | Ac | |
| 28,3 | Ac | |
| 28,4 | Ac | |
| 28,6 | Ac | |
| 28 | bDGlcp | 91.5 | 69.7 | 72.7 | 67.8 | 72.3 | 61.4 | |
| 3 | Ac | |
| 19 | Ac | |
| | Subst | 37.7 | 25.7 | 77.0 | 51.6 | 50.5 | 22.8 | 32.4 | 40.0 | 47.0 | 36.5 | 23.9 | 128.7 | 137.3 | 40.9 | 28.1 | 23.5 | 47.7 | 52.8 | 72.9 | 40.9 | 25.1 | 36.2 | 180.2 | 11.5 | 15.5 | 15.9 | 24.0 | 175.6 | 27.2 | 16.6 |
|
There is only one chemically distinct structure:
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