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Puri SC, Nazir A, Chawla R, Arora R, Riyaz-Ul-Hasan S, Amna T, Ahmed B, Verma V, Singh S, Sagar R, Sharma A, Kumar R, Sharma RK, Qazi GN
The endophytic fungus Trametes hirsuta as a novel alternative source of podophyllotoxin and related aryl tetralin lignans
Journal of Biotechnology 122(4) (2006)
494-510
|
b-D-Glcp-(1-9)-Subst
Subst = 3',4',5'-tridemethylpodophyllotoxin = SMILES O=C1OC[C@@H]2{9}[C@H](C3=C([C@H]([C@@H]12)C4=C{53}C(O)={54}C(O){55}C(O)=C4)C=C5OCOC5=C3)O |
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Trametes hirsuta
(NCBI TaxID 5327,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Host organism: Podophyllum hexandrum; Sinopodophyllum hexandrum
Organ / tissue: mycelium
The structure was elucidated in this paperNCBI PubMed ID: 16375985Publication DOI: 10.1016/j.jbiotec.2005.10.015Journal NLM ID: 8411927Publisher: Amsterdam: Elsevier
Correspondence: Puri SC <rks
inmas.org>
Institutions: Natural Products Chemistry Division, Regional Research Laboratory (CSIR), Jammu, India, Biotechnology Division, Regional Research Laboratory (CSIR), Jammu, India, Institute of Nuclear Medicine and Allied Sciences (DRDO), Delhi, India
The aryl tetralin lignans are synthesized by Podophyllum sps. and are in great demand worldwide due to their use in synthesis of topoisomerase inhibitors. However, the sustained production of these aryl tetralin lignans requires large-scale harvesting from the natural environments, which has resulted in the plant-endangered status. In view of the difficulties in their total chemical synthesis, cultivation and failure of metabolic engineering approaches, there is a need to search for alternative sources of production of aryl tetralin lignans. We unequivocally established the methodology for isolation, identification, and characterization of a novel fungal endophyte (Trametes hirsuta) that produces aryl tetralin lignans consistently as shown by HPLC, LC-MS, LC/MS-MS and 1H NMR. The lignans produced by the microorganism are biologically active, and exhibit potent antioxidant, anticancer and radioprotective properties. This strategy promises to improve the production of these therapeutically important compounds at lower costs
endophyte, Podophyllum hexandrum, Trametes hirsuta, radioprotection, aryl tetralin lignans, podophyllotoxin
Structure type: monomer ; 599.15 [M+Na]+
Location inside paper: Table 1, fungal podophyllotoxin-glycoside, Fig. 4, b
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 1H NMR, IR, DNA sequencing, DNA techniques, TLC, ESI-MS/MS, biological assays, HPLC, extraction, optical rotation measurement, LC-MS, cell growth, melting point determination, cytotoxicity assay, radical scavenging assay, evaporation, sonication, centrifugation, LC-APCI-MS/MS
NCBI Taxonomy refs (TaxIDs): 5327
Show glycosyltransferases
NMR conditions: in CDCl3
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
9 bDGlcp 104.69 75.20 78.00 71.22 77.06 68.56
Subst
1H NMR data: present in publication
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 9 | bDGlcp | 104.69 | 75.20 | 78.00 | 71.22 | 77.06 | 68.56 |
| | Subst | |
|
There is only one chemically distinct structure:
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Roscher R, Herderich M, Steffen JP, Schreier P, Schwab W
2,5-Dimethyl-4-hydroxy-3[2H]-furanone 6'O-malonyl-β-D-glucopyranoside in strawberry fruits
Phytochemistry 43(1) (1996)
155-159
|
b-D-Glcp-(1-3)-Subst
Subst = 4-hydroxy-2,5-dimethylfuran-3(2H)-one = SMILES C/C1={3}C(O)/C(=O)C(C)O1 |
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Fragaria x ananassa
(previously named: Fragaria ananassa, Fragaria chiloensis x Fragaria virginiana, Fragaria virginiana x Fragaria chiloensis)
(NCBI TaxID 3747,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: fruit
The structure was elucidated in this paperNCBI PubMed ID: 8987510Publication DOI: 10.1016/0031-9422(96)00216-6Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Lehrstuhl für Lebensmittelchemie, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany
2,5-Dimethyl-4-hydroxy-3[2H]-furanone 6'-O-malonyl-β-D-glucopyranoside was isolated from a glycosidic extract of strawberry fruit (Fragaria x ananassa, cv. Senga Sengana) by means of countercurrent chromatography and reverse-phase HPLC. Identification was achieved by comparison of chromatographic and 1H, 13C and 2D-NMR, as well as mass spectral data with those of the synthesized reference compound. In ripe strawberry fruit, a 1:1 ratio of the malonylated glucoside to its deacylated glucoconjugate was determined by on-line liquid chromatography-atmospheric pressure chemical ionization-tandem mass spectrometry.
2, rosaceae, countercurrent chromatography, Fragaria x ananassa, strawberry fruits, 6'O-malonyl-β-D-glucopyranoside, 5-dimethyl-4-hydroxy-3[2H]furanone, furaneol®, HPLC-MS/MS
Structure type: monomer ; 291 [M+H]+
C
12H
18O
8Location inside paper: compound 1, p. 155 (fig., 1), table 3(1), p. 158 (right col., compound 1)
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, TLC, enzymatic hydrolysis, HPLC, UV, DEPT, COSY, HPLC-MS/MS, LC-APCI-MS/MS, MLCCC, HRGC-MS, HRGC, HPLC-ESI-MS/MS
Synthetic data: chemical
Comments, role: NMR temperature was not specified, experimental data in tables 1-3 is given for synthetic compound
Related record ID(s): 62295
NCBI Taxonomy refs (TaxIDs): 3747
Show glycosyltransferases
NMR conditions: in D2O
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3 bDGlcp 105.9 75.8 78.3 72.1 79.0 63.3
Subst 16.6 188.4 136.0 203.2 84.7 18.0-18.1
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3 bDGlcp 4.73-4.80 3.42-3.54 3.42-3.54 3.42-3.54 3.42-3.54 3.73-3.87
Subst 2.40 - - - 4.73-4.80 1.45
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3 bDGlcp 105.9/4.73-4.80 75.8/3.42-3.54 78.3/3.42-3.54 72.1/3.42-3.54 79.0/3.42-3.54 63.3/3.73-3.87
Subst 16.6/2.40 84.7/4.73-4.80 18.0-18.1/1.45
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3 | bDGlcp | 4.73
4.80 | 3.42
3.54 | 3.42
3.54 | 3.42
3.54 | 3.42
3.54 | 3.73
3.87 |
| | Subst | 2.40 |
|
|
| 4.73
4.80 | 1.45 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3 | bDGlcp | 105.9 | 75.8 | 78.3 | 72.1 | 79.0 | 63.3 |
| | Subst | 16.6 | 188.4 | 136.0 | 203.2 | 84.7 | 18.0
18.1 |
|
There is only one chemically distinct structure:
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Roscher R, Herderich M, Steffen JP, Schreier P, Schwab W
2,5-Dimethyl-4-hydroxy-3[2H]-furanone 6'O-malonyl-β-D-glucopyranoside in strawberry fruits
Phytochemistry 43(1) (1996)
155-159
|
Mal-(1-6)-b-D-Glcp-(1-3)-Subst
Subst = 4-hydroxy-2,5-dimethylfuran-3(2H)-one = SMILES C/C1={3}C(O)/C(=O)C(C)O1 |
Show graphically |
Fragaria x ananassa
(previously named: Fragaria ananassa, Fragaria chiloensis x Fragaria virginiana, Fragaria virginiana x Fragaria chiloensis)
(NCBI TaxID 3747,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: fruit
The structure was elucidated in this paperNCBI PubMed ID: 8987510Publication DOI: 10.1016/0031-9422(96)00216-6Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Lehrstuhl für Lebensmittelchemie, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany
2,5-Dimethyl-4-hydroxy-3[2H]-furanone 6'-O-malonyl-β-D-glucopyranoside was isolated from a glycosidic extract of strawberry fruit (Fragaria x ananassa, cv. Senga Sengana) by means of countercurrent chromatography and reverse-phase HPLC. Identification was achieved by comparison of chromatographic and 1H, 13C and 2D-NMR, as well as mass spectral data with those of the synthesized reference compound. In ripe strawberry fruit, a 1:1 ratio of the malonylated glucoside to its deacylated glucoconjugate was determined by on-line liquid chromatography-atmospheric pressure chemical ionization-tandem mass spectrometry.
2, rosaceae, countercurrent chromatography, Fragaria x ananassa, strawberry fruits, 6'O-malonyl-β-D-glucopyranoside, 5-dimethyl-4-hydroxy-3[2H]furanone, furaneol®, HPLC-MS/MS
Structure type: monomer ; 377 [M+H]+
C
15H
20O
11Location inside paper: compound 2, p. 155 (fig., 2), table 3(2), p. 158 (right col., compound 2)
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, TLC, enzymatic hydrolysis, HPLC, UV, DEPT, COSY, HPLC-MS/MS, LC-APCI-MS/MS, MLCCC, HRGC-MS, HRGC, HPLC-ESI-MS/MS
Synthetic data: chemical
Comments, role: NMR temperature was not specified, experimental data in tables 1-3 is given for synthetic compound
Related record ID(s): 62294
NCBI Taxonomy refs (TaxIDs): 3747
Show glycosyltransferases
NMR conditions: in D2O
[as TSV]
13C NMR data:
missing...
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,6 xXMal - 3.32 -
3 bDGlcp 4.70-4.84 3.45-3.85 3.45-3.85 3.45-3.85 3.45-3.85 4.31-4.44
Subst 2.30 - - - 4.65-4.90 1.43
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,6 | xXMal |
| 3.32 |
| |
| 3 | bDGlcp | 4.70
4.84 | 3.45
3.85 | 3.45
3.85 | 3.45
3.85 | 3.45
3.85 | 4.31
4.44 |
| | Subst | 2.30 |
|
|
| 4.65
4.90 | 1.43 |
|
There is only one chemically distinct structure:
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