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1. (Article ID: 11914)
Fontanel D, Galtier C, Debouzy JC, Gueiffier A, Viel C
Sesquiterpene lactone glycosides from Lapsana communis L. subsp. communis
Phytochemistry 51(8) (1999)
999-1004
From the latex of Lapsana communis L. subps. communis, five guaianolide glycosides were identified: crepiside E, tectoroside and three new ones: 3-O-β-D-glucopyranosyl-8-O-β-acetyl-1αH,5αH,6βH,7αH-guai-4(15),10(14),11(13)-triene-6,12-olide, 3-O-β-D-glucopyranosyl-8-O-β-acetyl-1αH,5αH,6βH,7αH-guai-3(4),10(14),11(13)-triene-15-methyl-6,12-olide, and 3-O-β-glucopyranosyl-8-O-β-(4-hydroxyphenyl)-lactyl-1αH,5αH,6βH,7αH-guai-3(4),10(14),11(13)-triene-15-methyl-6,12-olide. Their structures were established by spectroscopic methods.
Asteraceae, Lactuceae, guaianolides, sesquiterpene lactone glycosides, Lapsana communis subsp. communis
NCBI PubMed ID: 10444857Publication DOI: 10.1016/S0031-9422(98)00718-3Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Department of Pharmacognosy, Faculty of Pharmaceutical Sciences, University of Tours, 31 Avenue Monge, 37 200 Tours, France, Department of Medicinal Chemistry, Faculty of Pharmaceutical Sciences, University of Tours, 31 Avenue Monge, 37 200 Tours, France, Department of Biophysic, Army Research Center of Health, 38 702 La Tronche, France
Methods: 13C NMR, 1H NMR, NOE, EI-MS, FAB-MS, TLC, HPLC, CI-MS, cytotoxicity assay, DEPT, NOESY, HOHAHA, DFQ-COSY
The publication contains the following compound(s):
- Compound ID: 30875
|
b-D-Glcp-(1-3)-Subst8Ac
Subst = 8-epidesacylcynaropicrin = SMILES C=C1C{8}[C@@H](O)[C@@H]2[C@H](OC(C2=C)=O)[C@@H]3[C@H]1C{3}[C@H](O)C3=C |
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Structure type: monomer
; 484 [M+NH4]+
Trivial name: lapsanoside A
Compound class: sesquiterpenoid glycoside
- Compound ID: 30876
|
Subst1-(9-8)-+
|
b-D-Glcp-(1-3)-Subst2
Subst1 = latifolicinin C acid = SMILES c1cc(ccc1CC({9}C(=O)O)O)O;
Subst2 = 8-epidesacylcynaropicrin = SMILES C=C1C{8}[C@@H](O)[C@@H]2[C@H](OC(C2=C)=O)[C@@H]3[C@H]1C{3}[C@H](O)C3=C |
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Structure type: monomer
Trivial name: tectoroside
Compound class: sesquiterpenoid glycoside
- Compound ID: 30877
|
b-D-Glcp-(1-3)-Subst
Subst = 8-epidesacylcynaropicrin = SMILES C=C1C{8}[C@@H](O)[C@@H]2[C@H](OC(C2=C)=O)[C@@H]3[C@H]1C{3}[C@H](O)C3=C |
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Structure type: monomer
; 484 [M+NH4]+
Trivial name: crepiside E
Compound class: sesquiterpenoid glycoside
- Compound ID: 30878
|
Subst1-(9-8)-+
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b-D-Glcp-(1-3)-Subst2
Subst1 = latifolicinin C acid = SMILES c1cc(ccc1CC({9}C(=O)O)O)O;
Subst2 = crepiside C aglycone = SMILES C=C1C{8}[C@@H](O)[C@H]2C(=C)C(=O)O[C@@H]2[C@H]2C(C)={3}C(O)C[C@@H]12 |
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Structure type: monomer
; 419
Trivial name: lapsanoside B
Compound class: sesquiterpenoid glycoside
- Compound ID: 30879
|
b-D-Glcp-(1-3)-Subst8Ac
Subst = crepiside C aglycone = SMILES C=C1C{8}[C@@H](O)[C@H]2C(=C)C(=O)O[C@@H]2[C@H]2C(C)={3}C(O)C[C@@H]12 |
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Structure type: monomer
Trivial name: lapsanoside C
Compound class: sesquiterpenoid glycoside
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