CAS 17575-20-1

Lanatosido A

Descripción:

Lanatosido A es un glucósido cardíaco derivado de las hojas de la planta Digitalis lanata, comúnmente conocida como dedalera lanosa. Se caracteriza por su capacidad para aumentar la fuerza de contracción del miocardio, lo que lo hace útil en el tratamiento de ciertas afecciones cardíacas, particularmente la insuficiencia cardíaca y la fibrilación auricular. El compuesto presenta un núcleo esteroide con un anillo de lactona y múltiples moieties de azúcar, que contribuyen a su actividad farmacológica. Lanatosido A exhibe una potencia relativamente alta y tiene una ventana terapéutica estrecha, lo que requiere un monitoreo cuidadoso de los niveles séricos durante el tratamiento para evitar toxicidad. Su mecanismo de acción implica la inhibición de la bomba Na+/K+ ATPasa, lo que lleva a un aumento de las concentraciones intracelulares de sodio y calcio, lo que mejora la contractilidad cardíaca. Además, se conoce que Lanatosido A tiene efectos secundarios potenciales, incluidos trastornos gastrointestinales y arritmias, particularmente en casos de sobredosis. Al igual que con otros glucósidos cardíacos, es importante considerar factores específicos del paciente al prescribir este medicamento.

Fórmula: C₄₉H₇₆O₁₉

InChI: InChI=1/C49H76O19/c1-22-43(66-38-18-33(53)44(23(2)61-38)67-39-19-34(63-25(4)51)45(24(3)62-39)68-46-42(57)41(56)40(55)35(20-50)65-46)32(52)17-37(60-22)64-28-9-12-47(5)27(16-28)7-8-31-30(47)10-13-48(6)29(11-14-49(31,48)58)26-15-36(54)59-21-26/h15,22-24,27-35,37-46,50,52-53,55-58H,7-14,16-21H2,1-6H3/t22-,23-,24?,27-,28+,29-,30+,31-,32+,33+,34+,35-,37+,38+,39+,40-,41+,42-,43-,44-,45-,46+,47+,48-,49+/m1/s1

Clave InChI: InChIKey=YFGQJKBUXPKSAW-YSTAXILLSA-N

SMILES: O[C@@]12[C@]3([C@@]([C@]4(C)[C@](CC3)(C[C@@H](O[C@H]5C[C@H](O)[C@H](O[C@H]6C[C@H](O)[C@H](O[C@H]7C[C@H](OC(C)=O)[C@H](O[C@@H]8O[C@H](CO)[C@@H](O)[C@H](O)[C@H]8O)[C@@H](C)O7)[C@@H](C)O6)[C@@H](C)O5)CC4)[H])(CC[C@]1(C)[C@H](CC2)C=9COC(=O)C9)[H])[H]

Sinónimos:

• (3beta,5beta)-3-{[beta-D-glucopyranosyl-(1->4)-(5xi)-3-O-acetyl-2,6-dideoxy-beta-D-erythro-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl]oxy}-14-hydroxycard-20(22)-enolide
• (3β,5β)-3-[(O-β-<span class="text-smallcaps">D</smallcap>-Glucopyranosyl-(1→4)-O-3-O-acetyl-2,6-dideoxy-β-<smallcap>D</smallcap>-ribo-hexopyranosyl-(1→4)-O-2,6-dideoxy-β-<smallcap>D</smallcap>-ribo-hexopyranosyl-(1→4)-2,6-dideoxy-β-<smallcap>D</span>-ribo-hexopyranosyl)oxy]-14-hydroxycard-20(22)-enolide
• 20(22),5Beta-Cardenolid-3Beta,14Beta-Diol 3Beta-(O-Beta-D-Glucopyranosyl-(1->4)-O-Beta-D-[3-O-Acetyldigitoxopyranosyl]-1(1->4)O-Beta-D-Digitoxopyranosyl-(1->4)-O-Beta-D-Digitoxopyranoside)
• 3-{[hexopyranosyl-(1->4)-3-O-acetyl-2,6-dideoxyhexopyranosyl-(1->4)-2,6-dideoxyhexopyranosyl-(1->4)-2,6-dideoxyhexopyranosyl]oxy}-14-hydroxycard-20(22)-enolide
• 5β-Card-20(22)-enolide, 3β-[[O-[O-(O-glucosyldigitoxosyl)digitoxosyl]digitoxosyl]oxy]-14-hydroxy-, acetate
• Adigal
• Card-20(22)-enolide, 3-[(O-β-<span class="text-smallcaps">D</smallcap>-glucopyranosyl-(1→4)-O-3-O-acetyl-2,6-dideoxy-β-<smallcap>D</smallcap>-ribo-hexopyranosyl-(1→4)-O-2,6-dideoxy-β-<smallcap>D</smallcap>-ribo-hexopyranosyl-(1→4)-2,6-dideoxy-β-<smallcap>D</span>-ribo-hexopyranosyl)oxy]-14-hydroxy-, (3β,5β)-
• Digilanida
• Digilanide A
• Digitoxigenin+2Digitoxose+Acetyl-Digilanidobose
• Lanatosid A
• NSC 7532
• (3β,5β)-3-[(O-β-D-Glucopyranosyl-(1→4)-O-3-O-acetyl-2,6-dideoxy-β-D-ribo-hexopyranosyl-(1→4)-O-2,6-dideoxy-β-D-ribo-hexopyranosyl-(1→4)-2,6-dideoxy-β-D-ribo-hexopyranosyl)oxy]-14-hydroxycard-20(22)-enolide
• Lanatoside A

Lanatoside A

CAS: 17575-20-1

Lanatoside A is a cardiac glycoside found in the plant "Lantana camara" and other plants of the family Verbenaceae. Lanatoside A is structurally characterized by an oxygenated hydroxyl group at C-3, which is present in the natural compound secoisolariciresinol. It has been shown to have inhibitory effects on enzymes involved in congestive heart failure such as myosin light chain kinase and serine/threonine protein kinase. Lanatoside A also has been shown to have immunomodulatory properties and may be beneficial for autoimmune diseases such as rheumatoid arthritis. The enzyme activities are inhibited by lanatosides at low pH values (pH 5-6) but not at high pH values (pH 7-8).

Pureza: Min. 95%

Ref: 3D-FL137799