Found 13 structures.
Displayed structures from 1 to 13
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1. Compound ID: 28586
Structure type: oligomer
Trivial name: plantalloside
Compound class: glycoside, phenolic glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 11315
Franzyk H, Husum TL, Jensen SR "A caffeoyl phenylethanoid glycoside from Plantago myosuros" -
Phytochemistry 47(6) (1998) 1161-1162
From Plantago myosuros, the iridoid glucoside, aucubin was isolated, together with the caffeoyl phenylethanoid glycosides, plantalloside and verbascoside. Plantalloside is a new verbascoside analogue with a beta-allopyranosyl moiety. The structure was elucidated by NMR spectroscopy.
verbascoside, Plantago myosuros, Plantaginaceae, aucubin, plantalloside, alloside
Publication DOI: 10.1016/S0031-9422(97)00527-XJournal NLM ID: 0151434Publisher: Elsevier
Institutions: Department of Organic Chemistry, The Technical University of Denmark, Lyngby, Denmark
Methods: 13C NMR, 1H NMR, extraction, optical rotation measurement, reversed-phase chromatography
- Article ID: 12622
Rønsted N, Gøbel E, Franzyk H, Jensen SR, Olsen CE "Chemotaxonomy of Plantago. Iridoid glucosides and caffeoyl phenylethanoid glycosides" -
Phytochemistry 55(4) (2000) 337-348
Data for 34 species of Plantago (Plantaginaceae), including subgen. Littorella (= Littorella uniflora), have been collected with regard to their content of iridoid glucosides and caffeoyl phenylethanoid glycosides (CPGs). In the present work, 21 species were investigated for the first time and many known compounds were found together with three new iridoid glucosides. Of these, arborescoside and arborescosidic acid, both of the uncommon type with an 8,9-double bond, were present in several species, while 6-deoxymelittoside was found only in P. subulata. The known compounds deoxyloganic acid, caryoptoside and rehmannioside D were isolated from the genus for the first time. The earlier reported occurrence of sorbitol in the family was confirmed, and this compound was shown by NMR spectroscopy to be the main sugar in the three species investigated for this. The combined data show that CPGs are present in all species investigated. With regard to the iridoids, the distribution patterns showed a good correlation with the classification of Rahn. Thus, aucubin is typical for the whole genus, while bartsioside and catalpol as well as 5-substituted iridoids are each characteristic for a subgenus in the family. Finally, the close relationship between Plantago and Veronica suggested by chloroplast DNA sequence analysis. could be corroborated by the common occurrence of the rare 8,9-unsaturated iridoids in these two genera.
Plantago; Plantaginaceae; chemotaxonomy; iridoid glucosides; bartsioside; aucubin; catalpol; arborescoside; arborescosidic acid; 6-deoxymelittoside; verbascoside; sorbitol
NCBI PubMed ID: 11117882Publication DOI: 10.1016/s0031-9422(00)00306-xJournal NLM ID: 0151434Publisher: Elsevier
Correspondence: Jensen SR
Institutions: Department of Organic Chemistry, The Technical University of Denmark, Lyngby, Denmark, Department of Chemistry, The Royal Veterinary and Agricultural University, Frederiksberg, Denmark
Methods: 13C NMR, 1H NMR, extraction, CC, MT: extraction
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2. Compound ID: 28807
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b-D-Xylp-(1-3)-+
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b-D-Allp-(1-6)-b-D-Glcp-(1-28)-Subst
Subst = pomolic acid = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H]){19}[C@](C)(O)[C@H](C)CC[C@@]({28}C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
; 951 [M+Na]+
C47H76O18
Trivial name: scabrioside A
Compound class: triterpenoid glycoside
Contained glycoepitopes: IEDB_114701,IEDB_142488,IEDB_146664,IEDB_167188,IEDB_174332,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 11352
Baykal T, Panayir T, Tasdemir D, Sticher O, Calis I "Triterpene saponins from Scabiosa rotata" -
Phytochemistry 48(5) (1998) 867-873
Four new allose-containing triterpenoid saponosides, scabriosides A, B, C and D were isolated from the roots of Scabiosa rotata. Their structures were established as 3-O-beta-D-xylopyranosyl-28-O-[beta-D-allopyranosyl (1-->6)-beta-D-glucopyranosyl]-pomolic acid, 3-O-[alpha-L-rhamnopyranosyl (1-->2)-beta-D-xylopyranosyl]-28-O-[beta-D-allopyranosyl (1-->6)-beta-D-glucopyranosyl]-pomolic acid, 3-O-[alpha-L-rhamnopyranosyl (1-->2)-alpha-L-arabinopyranosyl]-28-O-[beta-D-allopyranosyl (1-->6)-beta-D-glucopyranosyl]-pomolic acid, and 3-O-[beta-D-glucopyranosyl (1-->3)-alpha-L-rhamnopyranosyl (1-->2)-beta-D-xylopyranosyl]-28-O-[beta-D-allopyranosyl(1-->6) -beta-D-glucopyranosyl]-pomolic acid, respectively, by the help of spectral evidence (IR, 1D- and 2D-NMR, FAB-MS).
pomolic acid, Dipsacaceae, Scabiosa rotata, triterpenoid saponosides, Scabrioside A, Scabrioside B, Scabrioside C, Scabrioside D
NCBI PubMed ID: 9664710Publication DOI: 10.1016/s0031-9422(97)00982-5Journal NLM ID: 0151434Publisher: Elsevier
Correspondence: Calis I
Institutions: Swiss Federal Institute of Technology (ETH) Zürich, Department of Pharmacy, Zürich, Switzerland, Department of Pharmacognosy, Faculty of Pharmacy, Gazi University, Ankara, Turkey, Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University Ankara, Turkey
Methods: 13C NMR, 1H NMR, IR, FAB-MS, GC-MS, TLC, extraction, CC, HMBC, HMQC, COSY, optical rotatin measurement
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3. Compound ID: 28808
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a-L-Rhap-(1-2)-b-D-Xylp-(1-3)-+
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b-D-Allp-(1-6)-b-D-Glcp-(1-28)-Subst
Subst = pomolic acid = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H]){19}[C@](C)(O)[C@H](C)CC[C@@]({28}C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
; 1097 [M+Na]+
C53H86O22
Trivial name: scabrioside B
Compound class: triterpenoid glycoside
Contained glycoepitopes: IEDB_114701,IEDB_136105,IEDB_142488,IEDB_146664,IEDB_167188,IEDB_174332,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 11352
Baykal T, Panayir T, Tasdemir D, Sticher O, Calis I "Triterpene saponins from Scabiosa rotata" -
Phytochemistry 48(5) (1998) 867-873
Four new allose-containing triterpenoid saponosides, scabriosides A, B, C and D were isolated from the roots of Scabiosa rotata. Their structures were established as 3-O-beta-D-xylopyranosyl-28-O-[beta-D-allopyranosyl (1-->6)-beta-D-glucopyranosyl]-pomolic acid, 3-O-[alpha-L-rhamnopyranosyl (1-->2)-beta-D-xylopyranosyl]-28-O-[beta-D-allopyranosyl (1-->6)-beta-D-glucopyranosyl]-pomolic acid, 3-O-[alpha-L-rhamnopyranosyl (1-->2)-alpha-L-arabinopyranosyl]-28-O-[beta-D-allopyranosyl (1-->6)-beta-D-glucopyranosyl]-pomolic acid, and 3-O-[beta-D-glucopyranosyl (1-->3)-alpha-L-rhamnopyranosyl (1-->2)-beta-D-xylopyranosyl]-28-O-[beta-D-allopyranosyl(1-->6) -beta-D-glucopyranosyl]-pomolic acid, respectively, by the help of spectral evidence (IR, 1D- and 2D-NMR, FAB-MS).
pomolic acid, Dipsacaceae, Scabiosa rotata, triterpenoid saponosides, Scabrioside A, Scabrioside B, Scabrioside C, Scabrioside D
NCBI PubMed ID: 9664710Publication DOI: 10.1016/s0031-9422(97)00982-5Journal NLM ID: 0151434Publisher: Elsevier
Correspondence: Calis I
Institutions: Swiss Federal Institute of Technology (ETH) Zürich, Department of Pharmacy, Zürich, Switzerland, Department of Pharmacognosy, Faculty of Pharmacy, Gazi University, Ankara, Turkey, Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University Ankara, Turkey
Methods: 13C NMR, 1H NMR, IR, FAB-MS, GC-MS, TLC, extraction, CC, HMBC, HMQC, COSY, optical rotatin measurement
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4. Compound ID: 28809
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a-L-Rhap-(1-2)-b-D-Arap-(1-3)-+
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b-D-Allp-(1-6)-b-D-Glcp-(1-28)-Subst
Subst = pomolic acid = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H]){19}[C@](C)(O)[C@H](C)CC[C@@]({28}C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
; 1097 [M+Na]+
C53H86O22
Trivial name: scabrioside C
Compound class: triterpenoid glycoside
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_581506,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 11352
Baykal T, Panayir T, Tasdemir D, Sticher O, Calis I "Triterpene saponins from Scabiosa rotata" -
Phytochemistry 48(5) (1998) 867-873
Four new allose-containing triterpenoid saponosides, scabriosides A, B, C and D were isolated from the roots of Scabiosa rotata. Their structures were established as 3-O-beta-D-xylopyranosyl-28-O-[beta-D-allopyranosyl (1-->6)-beta-D-glucopyranosyl]-pomolic acid, 3-O-[alpha-L-rhamnopyranosyl (1-->2)-beta-D-xylopyranosyl]-28-O-[beta-D-allopyranosyl (1-->6)-beta-D-glucopyranosyl]-pomolic acid, 3-O-[alpha-L-rhamnopyranosyl (1-->2)-alpha-L-arabinopyranosyl]-28-O-[beta-D-allopyranosyl (1-->6)-beta-D-glucopyranosyl]-pomolic acid, and 3-O-[beta-D-glucopyranosyl (1-->3)-alpha-L-rhamnopyranosyl (1-->2)-beta-D-xylopyranosyl]-28-O-[beta-D-allopyranosyl(1-->6) -beta-D-glucopyranosyl]-pomolic acid, respectively, by the help of spectral evidence (IR, 1D- and 2D-NMR, FAB-MS).
pomolic acid, Dipsacaceae, Scabiosa rotata, triterpenoid saponosides, Scabrioside A, Scabrioside B, Scabrioside C, Scabrioside D
NCBI PubMed ID: 9664710Publication DOI: 10.1016/s0031-9422(97)00982-5Journal NLM ID: 0151434Publisher: Elsevier
Correspondence: Calis I
Institutions: Swiss Federal Institute of Technology (ETH) Zürich, Department of Pharmacy, Zürich, Switzerland, Department of Pharmacognosy, Faculty of Pharmacy, Gazi University, Ankara, Turkey, Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University Ankara, Turkey
Methods: 13C NMR, 1H NMR, IR, FAB-MS, GC-MS, TLC, extraction, CC, HMBC, HMQC, COSY, optical rotatin measurement
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5. Compound ID: 28810
|
b-D-Allp-(1-6)-b-D-Glcp-(1-28)-+
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b-D-Glcp-(1-3)-a-L-Rhap-(1-2)-b-D-Xylp-(1-3)-Subst
Subst = pomolic acid = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H]){19}[C@](C)(O)[C@H](C)CC[C@@]({28}C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
; 1259 [M+Na]+
C59H96O27
Trivial name: scabrioside D
Compound class: triterpenoid glycoside
Contained glycoepitopes: IEDB_114701,IEDB_136105,IEDB_142488,IEDB_146664,IEDB_167188,IEDB_174332,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 11352
Baykal T, Panayir T, Tasdemir D, Sticher O, Calis I "Triterpene saponins from Scabiosa rotata" -
Phytochemistry 48(5) (1998) 867-873
Four new allose-containing triterpenoid saponosides, scabriosides A, B, C and D were isolated from the roots of Scabiosa rotata. Their structures were established as 3-O-beta-D-xylopyranosyl-28-O-[beta-D-allopyranosyl (1-->6)-beta-D-glucopyranosyl]-pomolic acid, 3-O-[alpha-L-rhamnopyranosyl (1-->2)-beta-D-xylopyranosyl]-28-O-[beta-D-allopyranosyl (1-->6)-beta-D-glucopyranosyl]-pomolic acid, 3-O-[alpha-L-rhamnopyranosyl (1-->2)-alpha-L-arabinopyranosyl]-28-O-[beta-D-allopyranosyl (1-->6)-beta-D-glucopyranosyl]-pomolic acid, and 3-O-[beta-D-glucopyranosyl (1-->3)-alpha-L-rhamnopyranosyl (1-->2)-beta-D-xylopyranosyl]-28-O-[beta-D-allopyranosyl(1-->6) -beta-D-glucopyranosyl]-pomolic acid, respectively, by the help of spectral evidence (IR, 1D- and 2D-NMR, FAB-MS).
pomolic acid, Dipsacaceae, Scabiosa rotata, triterpenoid saponosides, Scabrioside A, Scabrioside B, Scabrioside C, Scabrioside D
NCBI PubMed ID: 9664710Publication DOI: 10.1016/s0031-9422(97)00982-5Journal NLM ID: 0151434Publisher: Elsevier
Correspondence: Calis I
Institutions: Swiss Federal Institute of Technology (ETH) Zürich, Department of Pharmacy, Zürich, Switzerland, Department of Pharmacognosy, Faculty of Pharmacy, Gazi University, Ankara, Turkey, Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University Ankara, Turkey
Methods: 13C NMR, 1H NMR, IR, FAB-MS, GC-MS, TLC, extraction, CC, HMBC, HMQC, COSY, optical rotatin measurement
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6. Compound ID: 30678
|
b-D-Allp-(1-6)-b-D-Glcp-(1-9)-Subst7Me
Subst = 7,9,10-trixydroxy-3R-methyl-1H-3,4-dihydronaphtho-[2,3c]-pyran-1-one = SMILES C[C@@H]1Cc2cc3c{7}c(O)c{9}c(O)c3{10}c(O)c2C(=O)O1 |
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Structure type: monomer
; 621 [M+Na]+
C27H35O15
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 11856
Vilegas W, Dokkeddal AL, Piacente S, Rastrelli L, Pizza C "New naphthopyranone glycosides from Paepalanthus vellozioides and Paepalanthus latipes" -
Journal of Natural Products 62(5) (1999) 746-749
Three new compounds 3,4-dihydro-10-hydroxy-7-methoxy-3-(R)-methyl-1H-3,4-dihydronaphtho-[2,3c]-pyran-1-one-9-O-β-D-glucopyranoside (1), 3,4-dihydro-10-hydroxy-7-methoxy-3-(R)-methyl-1H-3,4-dihydronaphtho-[2,3c]-pyran-1-one-9-O-β-D-glucopyranosyl-(1→6)-glucopyranoside (2), and 3,4-dihydro-10-dihydroxy-7-methoxy-3-(R)-methyl-1H-3,4-dihydronaphtho-[2,3c]-pyran-1-one-9-O-β-D-allopyranosyl(1→6)glucopyranoside (3) were isolated from the leaves of Paepalanthus vellozioides and Paepalanthus latipes and characterized by spectrometric methods, mainly electrospray mass spectrometry and 1D and 2D NMR experiments. These unusual glycosylated dihydronaphthopyranones may serve as taxonomic markers of the genus Paepalanthus, since these compounds were not detected in other genera belonging to the Eriocaulaceae family.
naphthopyranone glycoside, Paepalanthus vellozioides, Paepalanthus latipes
NCBI PubMed ID: 10346959Publication DOI: 10.1021/np980082tJournal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: Pizza C
Institutions: niversidade Estadual Paulista, Instituto de Quimica de Araraquara, Caixa Postal 355, 14800−900 Araraquara, SP, Brazil, Università degli Studi di Salerno, Facoltà di Farmacia, Dipartimento di Scienze Farmaceutiche, Piazza V. Emanuele 9 - 84084, Penta di Fisciano (SA), Italy
Methods: 13C NMR, 1H NMR, GC-MS, TLC, enzymatic hydrolysis, ESI-MS, UV, optical rotation measurement, CD, TOCSY, DQF-COSY, HMBC, DEPT, HSQC, sulfuric acid hydrolysis
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7. Compound ID: 30790
Structure type: oligomer
Trivial name: martinoside
Compound class: phenylethanoid glycoside
The structure is contained in the following publication(s):
- Article ID: 11895
Takeda T, Narukawa Y, Hada N "Studies on the constituents of Leonotis nepetaefolia" -
Chemical and Pharmaceutical Bulletin 47(2) (1999) 284-286
Three antioxidative phenylethanoid glycosides and two new iridoid glycosides, along with three known iridoids were isolated from the African medicinal plant, Leonotis nepetaefolia R. BR. (Labiatae). The new iridoid glycosides were established as 10-O-(trans-3,4-dimethoxycinnamoyl)geniposidic acid and 10-O-(p-hydroxybenzoyl)geniposidic acid. Antioxidative activities of the compounds were measured by α,α-diphenyl-β-picrylhydrazyl (DPPH) method, and the three known phenylethanoid glycosides, acteoside, martynoside and lavandulifolioside showed strong antioxidative activity.
antioxidative activity, phenylethanoid glycoside, Labiatae, Leonotis nepetaefolia, acylated geniposidic acid
Publication DOI: 10.1248/cpb.47.284Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Kyoritsu College of Pharmacy, Tokyo, Japan
Methods: 13C NMR, 1H NMR, FAB-MS, TLC, HPLC, alkaline hydrolysis, UV, optical rotation measurement, antioxidant activities, HMBC, HR-FAB-MS
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8. Compound ID: 32662
|
b-D-Allp6Ac-(1-2)-b-D-Glcp6Ac-(1-7)-Subst4'Me
Subst = isoscutellarein = SMILES O=C(C1=C({8}C(O)={7}C(O){6}C={5}C1O)O2)C=C2C3=CC={54}C(O)C=C3 |
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Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 12619
Rodríguez-Lyon ML, Diaz-Lanza AM, Bernabé M, Villaescusa-Castillo L "Flavone glycosides containing acetylated sugars from Sideritis hyssopifolia" -
Magnetic Resonance in Chemistry 38(8) (2000) 684-687
From the aerial parts of Sideritis hyssopifolia one new and three known flavone glycosides were isolated and identified by chemical and spectral methods as 4′-O-methylisoscutellarein-7-O-[6′′′-O-acetyl-β-D-allopyranosyl-(1→2)]-6′′-O-acetyl-β-D-glucopyranoside, hypolaetin 7-O-[6′′′-O-acetyl-β-D-allopyranosyl-(1→2)]-β-D-glucopyranoside, hypolaetin 7-O-[6′′′-O-acetyl-β-D-allopyranosyl-(1→2)]-6′′-O-acetyl-β-D-glucopyranoside and isoscutellarein-7-O-[6′′′-O-acetyl-β-D-allopyranosyl-(1→2)]-β-D-glucopyranoside.
NMR; 1H NMR; 13C NMR; 2D NMR; flavone glycosides; Sideritis hyssopifolia; Lamiaceae
Publication DOI: 10.1002/1097-458X(200008)38:8<684::AID-MRC683>3.0.CO;2-GJournal NLM ID: 9882600Publisher: Wiley Heyden
Correspondence: Díaz-Lanza AM
Institutions: Laboratorio de Farmacognosia, Departamento de Farmacología, Facultad de Farmacia, Universidad de Alcalá de Henares, Alcalá de Henares, Spain, Departamento de Química Orgánica Biológica, Instituto de Química Orgánica General (CSIC), Madrid, Spain
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, ESI-MS, HPLC, extraction, HR-ESI-MS, evaporation, centrifugation
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9. Compound ID: 32663
|
b-D-Allp6Ac-(1-2)-b-D-Glcp-(1-7)-Subst
Subst = hypolaetin = SMILES O=c1cc(-c2cc{54}c(O){53}c(O)c2)oc2{8}c(O){7}c(O)c{5}c(O)c12 |
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Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 12619
Rodríguez-Lyon ML, Diaz-Lanza AM, Bernabé M, Villaescusa-Castillo L "Flavone glycosides containing acetylated sugars from Sideritis hyssopifolia" -
Magnetic Resonance in Chemistry 38(8) (2000) 684-687
From the aerial parts of Sideritis hyssopifolia one new and three known flavone glycosides were isolated and identified by chemical and spectral methods as 4′-O-methylisoscutellarein-7-O-[6′′′-O-acetyl-β-D-allopyranosyl-(1→2)]-6′′-O-acetyl-β-D-glucopyranoside, hypolaetin 7-O-[6′′′-O-acetyl-β-D-allopyranosyl-(1→2)]-β-D-glucopyranoside, hypolaetin 7-O-[6′′′-O-acetyl-β-D-allopyranosyl-(1→2)]-6′′-O-acetyl-β-D-glucopyranoside and isoscutellarein-7-O-[6′′′-O-acetyl-β-D-allopyranosyl-(1→2)]-β-D-glucopyranoside.
NMR; 1H NMR; 13C NMR; 2D NMR; flavone glycosides; Sideritis hyssopifolia; Lamiaceae
Publication DOI: 10.1002/1097-458X(200008)38:8<684::AID-MRC683>3.0.CO;2-GJournal NLM ID: 9882600Publisher: Wiley Heyden
Correspondence: Díaz-Lanza AM
Institutions: Laboratorio de Farmacognosia, Departamento de Farmacología, Facultad de Farmacia, Universidad de Alcalá de Henares, Alcalá de Henares, Spain, Departamento de Química Orgánica Biológica, Instituto de Química Orgánica General (CSIC), Madrid, Spain
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, ESI-MS, HPLC, extraction, HR-ESI-MS, evaporation, centrifugation
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10. Compound ID: 32664
|
b-D-Allp6Ac-(1-2)-b-D-Glcp6Ac-(1-7)-Subst
Subst = hypolaetin = SMILES O=c1cc(-c2cc{54}c(O){53}c(O)c2)oc2{8}c(O){7}c(O)c{5}c(O)c12 |
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Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 12619
Rodríguez-Lyon ML, Diaz-Lanza AM, Bernabé M, Villaescusa-Castillo L "Flavone glycosides containing acetylated sugars from Sideritis hyssopifolia" -
Magnetic Resonance in Chemistry 38(8) (2000) 684-687
From the aerial parts of Sideritis hyssopifolia one new and three known flavone glycosides were isolated and identified by chemical and spectral methods as 4′-O-methylisoscutellarein-7-O-[6′′′-O-acetyl-β-D-allopyranosyl-(1→2)]-6′′-O-acetyl-β-D-glucopyranoside, hypolaetin 7-O-[6′′′-O-acetyl-β-D-allopyranosyl-(1→2)]-β-D-glucopyranoside, hypolaetin 7-O-[6′′′-O-acetyl-β-D-allopyranosyl-(1→2)]-6′′-O-acetyl-β-D-glucopyranoside and isoscutellarein-7-O-[6′′′-O-acetyl-β-D-allopyranosyl-(1→2)]-β-D-glucopyranoside.
NMR; 1H NMR; 13C NMR; 2D NMR; flavone glycosides; Sideritis hyssopifolia; Lamiaceae
Publication DOI: 10.1002/1097-458X(200008)38:8<684::AID-MRC683>3.0.CO;2-GJournal NLM ID: 9882600Publisher: Wiley Heyden
Correspondence: Díaz-Lanza AM
Institutions: Laboratorio de Farmacognosia, Departamento de Farmacología, Facultad de Farmacia, Universidad de Alcalá de Henares, Alcalá de Henares, Spain, Departamento de Química Orgánica Biológica, Instituto de Química Orgánica General (CSIC), Madrid, Spain
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, ESI-MS, HPLC, extraction, HR-ESI-MS, evaporation, centrifugation
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11. Compound ID: 32665
|
b-D-Allp6Ac-(1-2)-b-D-Glcp-(1-7)-Subst
Subst = isoscutellarein = SMILES O=C(C1=C({8}C(O)={7}C(O){6}C={5}C1O)O2)C=C2C3=CC={54}C(O)C=C3 |
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Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 12619
Rodríguez-Lyon ML, Diaz-Lanza AM, Bernabé M, Villaescusa-Castillo L "Flavone glycosides containing acetylated sugars from Sideritis hyssopifolia" -
Magnetic Resonance in Chemistry 38(8) (2000) 684-687
From the aerial parts of Sideritis hyssopifolia one new and three known flavone glycosides were isolated and identified by chemical and spectral methods as 4′-O-methylisoscutellarein-7-O-[6′′′-O-acetyl-β-D-allopyranosyl-(1→2)]-6′′-O-acetyl-β-D-glucopyranoside, hypolaetin 7-O-[6′′′-O-acetyl-β-D-allopyranosyl-(1→2)]-β-D-glucopyranoside, hypolaetin 7-O-[6′′′-O-acetyl-β-D-allopyranosyl-(1→2)]-6′′-O-acetyl-β-D-glucopyranoside and isoscutellarein-7-O-[6′′′-O-acetyl-β-D-allopyranosyl-(1→2)]-β-D-glucopyranoside.
NMR; 1H NMR; 13C NMR; 2D NMR; flavone glycosides; Sideritis hyssopifolia; Lamiaceae
Publication DOI: 10.1002/1097-458X(200008)38:8<684::AID-MRC683>3.0.CO;2-GJournal NLM ID: 9882600Publisher: Wiley Heyden
Correspondence: Díaz-Lanza AM
Institutions: Laboratorio de Farmacognosia, Departamento de Farmacología, Facultad de Farmacia, Universidad de Alcalá de Henares, Alcalá de Henares, Spain, Departamento de Química Orgánica Biológica, Instituto de Química Orgánica General (CSIC), Madrid, Spain
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, ESI-MS, HPLC, extraction, HR-ESI-MS, evaporation, centrifugation
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12. Compound ID: 33222
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b-D-Allp-(1-4)-b-D-Olip3Me-(1-4)-b-D-Digp-(1-4)-b-D-Digp-(1-4)-b-D-Digp-(1-3)-Subst
Subst = 15β-hydroxylineolon = SMILES CC([C@@H]1C{15}[C@@H](O){14}[C@]2(O){8}[C@]3(O)CC=C4C{3}[C@@H](O)CC[C@]4(C)[C@@]3([H])C{12}[C@@H](O)[C@]12C)=O |
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Structure type: oligomer
Compound class: glycoside, triterpenoid glycoside
The structure is contained in the following publication(s):
- Article ID: 12815
Warashina T, Noro T "Steroidal glycosides from the aerial part of Asclepias incarnata" -
Phytochemistry 53(4) (2000) 485-498
The aerial part of Asclepias incarnata afforded 34 pregnane glycosides. These were confirmed to have lineolon, isolineolon, ikemagenin, 12-O-nicotinoyllineolon, deacylmetaplexigenin, metaplexigenin, rostratamine, 12-O-acetyllineolon, 15β-hydroxylineolon and 15β-hydroxyisolineolon moieties as their aglycones, and 2,6-dideoxyhexopyranose, glucopyranose and allopyranose as the corresponding sugar constituents. Their structures were determined using both spectroscopic and chemical methods.
2, Asclepiadaceae, pregnane glycoside, 6-dideoxyhexopyranose, Asclepias incarnata
NCBI PubMed ID: 10731028Publication DOI: 10.1016/s0031-9422(99)00560-9Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Institute for Environmental Sciences, University of Shizuoka, Shizuoka, Japan
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, ESI-MS, acid hydrolysis, HPLC, extraction, CC, HR-ESI-MS, evaporation, centrifugation
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13. Compound ID: 33294
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b-D-Allp-(1-4)-b-D-Olip3Me-(1-4)-b-D-Digp3Me-(1-4)-b-D-Olip3Me-(1-4)-b-D-Olip3Me-(1-4)-b-D-Olip-(1-3)-Subst
Subst = 15β-hydroxylineolon = SMILES CC([C@@H]1C{15}[C@@H](O){14}[C@]2(O){8}[C@]3(O)CC=C4C{3}[C@@H](O)CC[C@]4(C)[C@@]3([H])C{12}[C@@H](O)[C@]12C)=O |
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Structure type: oligomer
Compound class: glycoside
The structure is contained in the following publication(s):
- Article ID: 12817
Warashina T, Noro T "Steroidal glycosides from the aerial part of Asclepias incarnata L. II." -
Chemical and Pharmaceutical Bulletin 48(1) (2000) 99-107
Thirty new steroidal glycosides were obtained from the aerial part of Asclepias incarnata L. (Asclepiadaceae). These glycosides were confirmed to have lineolon, isolineolon, 12-O-acetyllineolon, 12-O-(Z)-cin-namoyllineolon, metaplexigenin, 15β-hydroxylineolon, 15β-hydroxyisolineolon, 16α-hydroxyisolineolon, 12-O-tigloyl-16α-hydroxyisolineolon as the aglycone and 2, 6-dideoxyhexoprranose as the sugar sequence by spectroscopic methods and chemical evidence.
2, Asclepiadaceae, 6-dideoxyhexopyranose, Asclepias incarnata, pregnane glycosice
NCBI PubMed ID: 10705484Publication DOI: 10.1248/cpb.48.99Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Institute for Environmental Sciences, University of Shizuoka, Shizuoka, Japan
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, ESI-MS, acid hydrolysis, HPLC, extraction, CC, HR-ESI-MS, evaporation, centrifugation
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