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Kofinas C, Chinou I, Loukis A, Harvala C, Maillard M, Hostettmann K
Flavonoids and bioactive coumarins of Tordylium apulum
Phytochemistry 48(4) (1998)
637-641
|
/Variants 0/-Kaempferol
/Variants 0/ is:
a-L-Rhap-(1-2)-b-D-Glcp-(1-3)-
OR (exclusively)
a-L-Rhap-(1-6)-b-D-Glcp-(1-3)- |
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Tordylium apulum
(NCBI TaxID 489417,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: aerial part
The structure was elucidated in this paperPublication DOI: 10.1016/S0031-9422(98)00018-1Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Division of Pharmacognosy, University of Athens, Panepistimiopolis Zografou, Athens, Creece, Institute de Pharmacognosie et Phytochimie, Universite de Lausanne, Lausanne, Switzerland
A new flavonol diglycoside, quercetin-3-O-[3,4 diacetyl-alpha-L-rhamnopyranosyl-(1-6)-beta-D-glucopyranoside and an antifungal dihydrofuranocoumarin, 2'(S),3'(R)-2'-acetoxyisopropyl-3'-acetoxy-2',3'- dihydroangelicin, together with four other known flavonoids and seven known bioactive coumarins, were isolated from the aerial parts of Tordylium apulum and their structures elucidated by NMR and mass spectroscopy.
antifungal activity, Apiaceae, flavonols, Tordylium apulum, dihydro-/furanocoumarins
Structure type: oligomer
Location inside paper: p. 637, column 1, paragraph 1, compound 9, compound 11
Compound class: glycoside
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_144144,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, HPLC, UV, extraction, CC, DEPT, TPS-MS
Related record ID(s): 61907, 61908
NCBI Taxonomy refs (TaxIDs): 489417
Show glycosyltransferases
There is only one chemically distinct structure:
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Kofinas C, Chinou I, Loukis A, Harvala C, Maillard M, Hostettmann K
Flavonoids and bioactive coumarins of Tordylium apulum
Phytochemistry 48(4) (1998)
637-641
Tordylium apulum
(NCBI TaxID 489417,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: aerial part
The structure was elucidated in this paperPublication DOI: 10.1016/S0031-9422(98)00018-1Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Division of Pharmacognosy, University of Athens, Panepistimiopolis Zografou, Athens, Creece, Institute de Pharmacognosie et Phytochimie, Universite de Lausanne, Lausanne, Switzerland
A new flavonol diglycoside, quercetin-3-O-[3,4 diacetyl-alpha-L-rhamnopyranosyl-(1-6)-beta-D-glucopyranoside and an antifungal dihydrofuranocoumarin, 2'(S),3'(R)-2'-acetoxyisopropyl-3'-acetoxy-2',3'- dihydroangelicin, together with four other known flavonoids and seven known bioactive coumarins, were isolated from the aerial parts of Tordylium apulum and their structures elucidated by NMR and mass spectroscopy.
antifungal activity, Apiaceae, flavonols, Tordylium apulum, dihydro-/furanocoumarins
Structure type: oligomer ; 695 [M+H]+
Location inside paper: p. 638, Scheme, compound 10, table 2
Compound class: glycoside
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_144144,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, HPLC, UV, extraction, CC, DEPT, TPS-MS
Related record ID(s): 61906, 61908
NCBI Taxonomy refs (TaxIDs): 489417
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
3,6,3 Ac 175.2 25.0
3,6,4 Ac 171.7 22.1
3,6 aLRhap 101.3 68.5 70.1 73.7 67.9 17.1
3 bDGlcp 101.4 74.0 76.4 68.9 76.0 67.3
xXQuercetin - 156.4 133.4 177.3 161.2 98.6 164.1 93.5 156.4 103.9 121.6 115.3 144.7 148.4 116.2 121.2
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16
3,6,3 Ac
3,6,4 Ac
3,6 aLRhap
3 bDGlcp 4.4 ? ? ? ? ?
xXQuercetin - - - - - 6.2 - 6.4 - - - 5.3 - - ? ?
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
3,6,3 Ac NMR TSV error 2: unequal length of 13C and 1H datasets
3,6,4 Ac NMR TSV error 2: unequal length of 13C and 1H datasets
3,6 aLRhap NMR TSV error 2: unequal length of 13C and 1H datasets
3 bDGlcp 101.4/4.4 74.0/? 76.4/? 68.9/? 76.0/? 67.3/?
xXQuercetin 98.6/6.2 93.5/6.4 115.3/5.3 116.2/? 121.2/?
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 |
|---|
| 3,6,3 | Ac | |
| 3,6,4 | Ac | |
| 3,6 | aLRhap | |
| 3 | bDGlcp | 4.4 | ? | ? | ? | ? | ? | |
| | xXQuercetin |
|
|
|
|
| 6.2 |
| 6.4 |
|
|
| 5.3 |
|
| ? | ? |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 | C16 |
|---|
| 3,6,3 | Ac | 175.2 | 25.0 | |
| 3,6,4 | Ac | 171.7 | 22.1 | |
| 3,6 | aLRhap | 101.3 | 68.5 | 70.1 | 73.7 | 67.9 | 17.1 | |
| 3 | bDGlcp | 101.4 | 74.0 | 76.4 | 68.9 | 76.0 | 67.3 | |
| | xXQuercetin |
| 156.4 | 133.4 | 177.3 | 161.2 | 98.6 | 164.1 | 93.5 | 156.4 | 103.9 | 121.6 | 115.3 | 144.7 | 148.4 | 116.2 | 121.2 |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":175.2,"l":"1","c":[0,0,0]},{"s":25,"l":"2","c":[0,0,0]},{"s":171.7,"l":"1","c":[0,0,0]},{"s":22.1,"l":"2","c":[0,0,0]},{"s":101.3,"l":"1","c":[0,0,225]},{"s":68.5,"l":"2","c":[0,0,225]},{"s":70.1,"l":"3","c":[0,0,225]},{"s":73.7,"l":"4","c":[0,0,225]},{"s":67.9,"l":"5","c":[0,0,225]},{"s":17.1,"l":"6","c":[0,0,225]},{"s":101.4,"l":"1","c":[230,0,30]},{"s":74,"l":"2","c":[230,0,30]},{"s":76.4,"l":"3","c":[230,0,30]},{"s":68.9,"l":"4","c":[230,0,30]},{"s":76,"l":"5","c":[230,0,30]},{"s":67.3,"l":"6","c":[230,0,30]},{"s":156.4,"l":"2","c":[0,165,0]},{"s":133.4,"l":"3","c":[0,165,0]},{"s":177.3,"l":"4","c":[0,165,0]},{"s":161.2,"l":"5","c":[0,165,0]},{"s":98.6,"l":"6","c":[0,165,0]},{"s":164.1,"l":"7","c":[0,165,0]},{"s":93.5,"l":"8","c":[0,165,0]},{"s":156.4,"l":"9","c":[0,165,0]},{"s":103.9,"l":"10","c":[0,165,0]},{"s":121.6,"l":"11","c":[0,165,0]},{"s":115.3,"l":"12","c":[0,165,0]},{"s":144.7,"l":"13","c":[0,165,0]},{"s":148.4,"l":"14","c":[0,165,0]},{"s":116.2,"l":"15","c":[0,165,0]},{"s":121.2,"l":"16","c":[0,165,0]}])
The spectrum also has 1 signal at unknown position (not plotted). |
There is only one chemically distinct structure:
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Kofinas C, Chinou I, Loukis A, Harvala C, Maillard M, Hostettmann K
Flavonoids and bioactive coumarins of Tordylium apulum
Phytochemistry 48(4) (1998)
637-641
|
/Variants 0/-+
|
a-L-Rhap-(1-6)-b-D-Glcp
/Variants 0/ is:
Quercetin-(3-1)-
OR (exclusively)
Subst-(3-1)-
Subst = isorhamnetin = SMILES O{3}C1=C(C2=CC={54}C(O)C(OC)=C2)OC3=C({5}C(O)=C{7}C(O)=C3)C1=O |
Show graphically |
Tordylium apulum
(NCBI TaxID 489417,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: aerial part
The structure was elucidated in this paperPublication DOI: 10.1016/S0031-9422(98)00018-1Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Division of Pharmacognosy, University of Athens, Panepistimiopolis Zografou, Athens, Creece, Institute de Pharmacognosie et Phytochimie, Universite de Lausanne, Lausanne, Switzerland
A new flavonol diglycoside, quercetin-3-O-[3,4 diacetyl-alpha-L-rhamnopyranosyl-(1-6)-beta-D-glucopyranoside and an antifungal dihydrofuranocoumarin, 2'(S),3'(R)-2'-acetoxyisopropyl-3'-acetoxy-2',3'- dihydroangelicin, together with four other known flavonoids and seven known bioactive coumarins, were isolated from the aerial parts of Tordylium apulum and their structures elucidated by NMR and mass spectroscopy.
antifungal activity, Apiaceae, flavonols, Tordylium apulum, dihydro-/furanocoumarins
Structure type: oligomer
Location inside paper: p. 637, column 1, paragraph 1, compound 12, compund 13
Compound class: glycoside
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_144144,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, HPLC, UV, extraction, CC, DEPT, TPS-MS
Related record ID(s): 61906, 61907
NCBI Taxonomy refs (TaxIDs): 489417
Show glycosyltransferases
There is only one chemically distinct structure:
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