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1. (Article ID: 10726)
Abe F, Yamauchi T
Cardenolide glycosides from the roots of Apocynum cannabinum
Chemical and Pharmaceutical Bulletin 42(10) (1994)
2028-2031
Steroidal constituents from the roots of Apocynum cannabinum L. were investigated. (20S)-, (20R)-18,20-Epoxycymarin and (20S)-18,20-epoxyapocannoside were isolated along with cannogenin, strophanthidin and cannogenol glycosides, including D-cymaroside, D-oleandroside, D-digitoxoside and D-digitaloside, and their glucosyl, cellobiosyl or gentiobiosyl glycosides. Two pregnanes, neridienone A and 6,7-didehydrocortexone, were obtained, accompanied with cardenolides.
6, neridienone A, Apocynum cannabinum, 18, 20-epoxystrophanthidin, cannogenin trioside, cardenolide, 7-didehydrocortexone
Publication DOI: 10.1248/cpb.42.2028Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Faculty of Pharmaceutical Sciences, Fukuoka University, Japan
Methods: 13C NMR, 1H NMR, FAB-MS, TLC, HPLC
The publication contains the following compound(s):
- Compound ID: 26677
|
b-D-Digp3Me-(1-3)-Subst
Subst = strophanthidin = SMILES C[C@]12CC[C@H]3[C@@H](CC{5}[C@@]4(O)[C@]3(C=O)CC{3}[C@H](O)C4){14}[C@@]1(O)CC[C@@H]2C5=CC(OC5)=O |
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Structure type: monomer
Trivial name: cymarin
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
40196, CBank-STR:491
- Compound ID: 26678
|
b-D-Digp-(1-3)-Subst
Subst = strophanthidin = SMILES C[C@]12CC[C@H]3[C@@H](CC{5}[C@@]4(O)[C@]3(C=O)CC{3}[C@H](O)C4){14}[C@@]1(O)CC[C@@H]2C5=CC(OC5)=O |
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Structure type: monomer
Trivial name: helveticoside
Compound class: saponin glycoside, triterpenoid glycoside
Reference(s) to other database(s): CCSD:
40197, CBank-STR:487
- Compound ID: 26679
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b-D-Glcp-(1-4)-b-D-Digp3Me-(1-3)-Subst
Subst = strophanthidin = SMILES C[C@]12CC[C@H]3[C@@H](CC{5}[C@@]4(O)[C@]3(C=O)CC{3}[C@H](O)C4){14}[C@@]1(O)CC[C@@H]2C5=CC(OC5)=O |
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Structure type: oligomer
Trivial name: k-strophanthin-β
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
40198, CBank-STR:2864
- Compound ID: 26680
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b-D-Digp3Me-(1-3)-Subst
Subst = cannogenin = SMILES C[C@]12CC[C@H]3[C@@H](CC[C@@]4([H])[C@]3(C=O)CC{3}[C@H](O)C4){14}[C@@]1(O)CC[C@@H]2C5=CC(OC5)=O |
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Structure type: monomer
Trivial name: apocannoside
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
40199, CBank-STR:489
- Compound ID: 26681
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b-D-Olip3Me-(1-3)-Subst
Subst = cannogenin = SMILES C[C@]12CC[C@H]3[C@@H](CC[C@@]4([H])[C@]3(C=O)CC{3}[C@H](O)C4){14}[C@@]1(O)CC[C@@H]2C5=CC(OC5)=O |
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Structure type: monomer
Trivial name: cynocannoside
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
40200, CBank-STR:1510
- Compound ID: 26682
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b-D-Glcp-(1-4)-b-D-Digp3Me-(1-3)-Subst
Subst = cannogenin = SMILES C[C@]12CC[C@H]3[C@@H](CC[C@@]4([H])[C@]3(C=O)CC{3}[C@H](O)C4){14}[C@@]1(O)CC[C@@H]2C5=CC(OC5)=O |
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Structure type: oligomer
Trivial name: apobioside
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
40201, CBank-STR:4399
- Compound ID: 26683
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b-D-Glcp-(1-4)-b-D-Fucp3Me-(1-3)-Subst
Subst = cannogenin = SMILES C[C@]12CC[C@H]3[C@@H](CC[C@@]4([H])[C@]3(C=O)CC{3}[C@H](O)C4){14}[C@@]1(O)CC[C@@H]2C5=CC(OC5)=O |
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Structure type: oligomer
; 733.3409 [M+Na]+
C36H54O14
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
40202, CBank-STR:5915
- Compound ID: 26684
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b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-b-D-Digp3Me-(1-3)-Subst
Subst = cannogenin = SMILES C[C@]12CC[C@H]3[C@@H](CC[C@@]4([H])[C@]3(C=O)CC{3}[C@H](O)C4){14}[C@@]1(O)CC[C@@H]2C5=CC(OC5)=O |
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Structure type: oligomer
; 879.3995 [M+Na]+
C42H64O18
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
40203, CBank-STR:7411
- Compound ID: 26685
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b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-b-D-Olip3Me-(1-3)-Subst
Subst = cannogenin = SMILES C[C@]12CC[C@H]3[C@@H](CC[C@@]4([H])[C@]3(C=O)CC{3}[C@H](O)C4){14}[C@@]1(O)CC[C@@H]2C5=CC(OC5)=O |
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Structure type: oligomer
; 879.400 [M+Na]+
C42H64O18
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
40204, CBank-STR:8400
- Compound ID: 26686
|
b-D-Glcp-(1-6)-b-D-Glcp-(1-4)-b-D-Digp3Me-(1-3)-Subst
Subst = cannogenin = SMILES C[C@]12CC[C@H]3[C@@H](CC[C@@]4([H])[C@]3(C=O)CC{3}[C@H](O)C4){14}[C@@]1(O)CC[C@@H]2C5=CC(OC5)=O |
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Structure type: oligomer
; 879.3988 [M+Na]+
C42H64O18
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
40205, CBank-STR:7412
- Compound ID: 26687
|
b-D-Glcp-(1-4)-b-D-Digp3Me-(1-3)-Subst
Subst = cannogenin = SMILES C[C@]12CC[C@H]3[C@@H](CC[C@@]4([H])[C@]3(C=O)CC{3}[C@H](O)C4){14}[C@@]1(O)CC[C@@H]2C5=CC(OC5)=O |
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Structure type: oligomer
; 719.3616 [M+Na]+
C36H56O13
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
40206, CBank-STR:2863
- Compound ID: 26688
|
b-D-Digp3Me-(1-3)-Subst
Subst = 20S-18,20-epoxystrophanthidin = SMILES O{14}[C@@]12[C@H](CC{5}[C@@]3(O)[C@]4(C=O)CC{3}[C@H](O)C3)[C@@H]4CC[C@@]15CO[C@]6(COC(C6)=O)[C@H]5CC2 |
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Structure type: monomer
; 587.2835 [M+Na]+
C30H44O10
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
40207, CBank-STR:494
- Compound ID: 26689
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b-D-Digp3Me-(1-3)-Subst
Subst = 20R-18,20-epoxystrophanthidin = SMILES O{14}[C@@]12[C@H](CC{5}[C@@]3(O)[C@]4(C=O)CC{3}[C@H](O)C3)[C@@H]4CC[C@@]15CO[C@@]6(COC(C6)=O)[C@H]5CC2 |
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Structure type: monomer
; 587.2835 [M+Na]+
C30H44O10
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
40208, CBank-STR:493
- Compound ID: 26690
|
b-D-Digp3Me-(1-3)-Subst
Subst = 20S-18,20-epoxycannogenin = SMILES O{14}[C@@]12[C@H](CC[C@@]3([H])[C@]4(C=O)CC{3}[C@H](O)C3)[C@@H]4CC[C@@]15CO[C@]6(COC(C6)=O)[C@H]5CC2 |
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Structure type: monomer
; 571.2887 [M+Na]+
C30H44O9
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
40209, CBank-STR:492
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2. (Article ID: 12470)
Melero CP, Medarde M, San Feliciano A
A short review on cardiotonic steroids and their aminoguanidine analogues
Molecules 5(1) (2000)
51-81
A short review on cardiotonic steroids and their analogues is presented. The natural, semisynthetic and synthetic derivatives, as well as their mechanism of action and structure-activity relationships are shown, with a special reference to aminoguanidine derivatives.
structure-activity relationships, digitalis glycosides analogues, inotropic activity, Na+, K+-ATPase, aminoguanidine analogues
Publication DOI: 10.3390/50100051Journal NLM ID: 100964009Publisher: Basel, Switzerland: MDPI
Correspondence: medarde
gugu.usal.es
Institutions: Departamento de Química Farmacéutica, Facultad de Farmacia, Salamanca, Spain
The publication contains the following compound(s):
- Compound ID: 32361
Structure type: monomer
Compound class: glycoside
- Compound ID: 32362
|
b-D-Glcp-(1-4)-b-D-Glcp-(1-4)-b-D-Digp3Me-(1-3)-Subst
Subst = digitalis-like aglycon |
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Structure type: oligomer
Compound class: glycoside
- Compound ID: 32363
|
b-D-Glcp-(1-6)-b-D-Glcp-(1-4)-b-D-Digp3Me-(1-3)-Subst
Subst = digitalis-like aglycon |
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Structure type: oligomer
Compound class: glycoside
- Compound ID: 22306
|
b-D-Digp-(1-4)-b-D-Digp-(1-4)-b-D-Digp-(1-3)-Subst
Subst = digoxigenin = SMILES O=C1OCC([C@H]2CC{14}[C@]3(O)[C@]4([H])CC[C@]5([H])C{3}[C@@H](O)CC[C@]5(C)[C@@]4([H])C{12}[C@@H](O)[C@]23C)=C1 |
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Structure type: oligomer
Trivial name: digoxin
Compound class: saponin glycoside, glycoside, triterpenoid glycoside, cardiac glycoside
Reference(s) to other database(s): CCSD:
3412, CBank-STR:3871, GenDB:MK530410
- Compound ID: 32354
|
b-D-Digp4Me-(1-4)-b-D-Digp-(1-4)-b-D-Digp-(1-3)-Subst
Subst = digoxigenin = SMILES O=C1OCC([C@H]2CC{14}[C@]3(O)[C@]4([H])CC[C@]5([H])C{3}[C@@H](O)CC[C@]5(C)[C@@]4([H])C{12}[C@@H](O)[C@]23C)=C1 |
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Structure type: oligomer
Trivial name: methyldigoxin
Compound class: glycoside, cardiac glycoside
- Compound ID: 32355
|
a-L-Rhap-(1-3)-Subst
Subst = ouabagenin = SMILES O{3}[C@H]1C{1}[C@@H](O)[C@]2({23}CO)[C@@H]3[C@H]({14}[C@@]4(O)CC[C@H](C5=CC(OC5)=O)[C@@]4(C)C{11}[C@H]3O)CC{5}[C@]2(O)C1 |
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Structure type: oligomer
Trivial name: ouabain
Compound class: glycoside
- Compound ID: 32356
|
b-D-Glcp-(1-4)-a-L-Rhap-(1-3)-Subst
Subst = hellebrigenin = SMILES O{3}[C@H]1CC[C@]2(C=O)[C@H]3CC[C@]4(C)[C@@H](C5=COC(C=C5)=O)CC{14}[C@]4(O)[C@@H]3CC{5}[C@]2(O)C1 |
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Structure type: oligomer
Trivial name: hellebrine
Compound class: glycoside
- Compound ID: 32357
|
b-D-Glcp-(1-4)-b-D-Digp3Ac-(1-3)-Subst
Subst = digitoxigenin = SMILES O{3}[C@H]1CC[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@H](C(CO5)=CC5=O)CC{14}[C@]4(O)[C@]3([H])CC[C@@]([H])2C1 |
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Structure type: oligomer
Compound class: glycoside
- Compound ID: 32358
|
b-D-Glcp-(1-4)-b-D-Digp3Me-(1-3)-Subst
Subst = acovenosigenin = SMILES O{3}[C@H]1C{1}[C@H](O)[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@H](C(CO5)=CC5=O)CC{14}[C@]4(O)[C@]3([H])CC[C@@]([H])2C1 |
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Structure type: oligomer
Trivial name: acobioside A
Compound class: glycoside
- Compound ID: 32359
|
b-D-Glcp-(1-6)-b-D-Glcp-(1-4)-b-D-Digp3Me-(1-3)-Subst14Ac
Subst = acovenosigenin = SMILES O{3}[C@H]1C{1}[C@H](O)[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@H](C(CO5)=CC5=O)CC{14}[C@]4(O)[C@]3([H])CC[C@@]([H])2C1 |
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Structure type: oligomer
Trivial name: 14-O-acetylacovenioside C
Compound class: glycoside
- Compound ID: 32360
Structure type: monomer
Compound class: glycoside
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