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Abstract:

A pregnane triglycoside containing a new genin 3β,14β-dihydroxy-21-methoxy-5β-pregnan-20-one has been isolated from the dried roots of Mandevilla pentlandiana. Chemical and spectroscopic evidence for the glycoside are consistent with the structure 3β,14β-dihydroxy-21-methoxy-5β-pregnan-20-one-3-O- β-d-diginopyranosyl-(1→4)- O-β-d-cymaropyranosyl-(1→4)-O-β-d-cymaropyranoside. It is noteworthy that 3β,14β, 21-trihydroxy 5β-pregnan-20-one, biosynthetically related to the genin of this glycoside, has been proved to be a precursor of cardenolides, also produced by this plant. © 1993.

Registro:

Documento: Artículo
Título:A pregnane glycoside from the roots of Mandevilla pentlandiana
Autor:Cabrera, G.; Seldes, A.M.; Gros, E.G.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellon 2, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Palabras clave:3β,14β-dihydroxy-21-methoxy-5β-pregnan-20-one; 3β,14β-dihydroxy-21-methoxy-5β-pregnan-20-one-3-O-β-d-diginopyranosyl- (1→4)-O-β- d-cymaropyranosyl-(1→4) -O-β-d-cymaropyranoside.; Apocynaceae; glycoside; Mandevilla pentlandiana; glycoside; pregnane derivative; article; carbohydrate analysis; chemical structure; chemistry; isolation and purification; molecular genetics; nuclear magnetic resonance spectroscopy; plant; Carbohydrate Sequence; Glycosides; Magnetic Resonance Spectroscopy; Molecular Sequence Data; Molecular Structure; Plants; Pregnanes; Support, Non-U.S. Gov't
Año:1992
Volumen:32
Número:1
Página de inicio:171
Página de fin:173
DOI: http://dx.doi.org/10.1016/0031-9422(92)80126-Y
Título revista:Phytochemistry
Título revista abreviado:Phytochemistry
ISSN:00319422
CODEN:PYTCA
CAS:Glycosides; Pregnanes
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00319422_v32_n1_p171_Cabrera

Referencias:

  • Reichstein, (1967) Naturwissenschaften, 54, p. 53
  • Yamauchi, (1985) Yakugaku Zasshi, 105, p. 695
  • Cabrera, Palermo, Seldes, Gros, Oberti, (1991) Phytochemistry, 30, p. 1239
  • Allgeier, Struktur der Drebyssobiose, Lilacinobiose und Viminose: Desoxyzucker, 45. Mitteilung (1968) Helvetica Chimica Acta, 51, p. 668
  • Nakagawa, Hayashi, Mitsuhashi, (1983) Chem. Pharm. Bull., 31, p. 2244
  • Tsukamoto, Hayashi, Mitsuhashi, (1985) Tetrahedron, 41, p. 927
  • Tsukamoto, Hayashi, Mitsuhashi, Snyckers, Fourie, (1985) Chem. Pharm. Bull., 33, p. 4807
  • Tsukamoto, Hayashi, Kaneko, Mitsuhashi, Snyckers, Fourie, Studies on the constituents of Asclepiadaceae plants. Part 67. Further studies on glycosides with a novel sugar chain containing a pair of optically isomeric sugars, D- and L-cymarose, from Cynanchum africanum (1988) Journal of the Chemical Society, Perkin Transactions 1, p. 2625
  • Zhang, Zhou, Hayashi, Kaneko, (1988) Phytochemistry, 27, p. 2935
  • Robien, Kopp, Schabl, Schwarz, (1987) Prog. NMR Spectrosc., 19, p. 131
  • Robinski, Tewalt, Sneden, Maquiroside A, a New Cytotoxic Cardiac Glycoside from Maquira calophylla (1987) Journal of Natural Products, 50, p. 211
  • Roush, Brown, (1983) J. Org. Chem., 48, p. 5093
  • Shashkov, Lipkind, Knirel, Kochetkov, Stereochemical factors determining the effects of glycosylation on the13C chemical shifts in carbohydrates (1988) Magnetic Resonance in Chemistry, 26, p. 735
  • Neszmelyi, Tori, Lukacs, Use of carbon-13 spin?lattice relaxation times for sugar sequence determination in steroidal oligosaccharides (1977) Journal of the Chemical Society, Chemical Communications, p. 613
  • Maier, (1985) Ph.D. Thesis. Facultad Ciencias Exactas y Naturales, Universidad de Buenos Aires
  • Kasai, Sakuma, Kawanish, Shoji, Constituents of Chinese Crude Drug"Wujiapi". VI. Studies on the Aglycones of Steroidal Glycosides of Bei-Wujiapi (2) (1972) CHEMICAL & PHARMACEUTICAL BULLETIN, 20, p. 1869
  • Tshesche, Becker, Hombach, (1968) Z. Naturforsch., 23 b, p. 1615
  • Bigler, (1983) J. Magn. Reson., 55, p. 468
  • Rangaswami, Reichstein, (1949) Helv. Chim. Acta, 32, p. 939
  • Sauer, Weiss, Reichstein, Die Glykoside der Samen vonDregea volubilis (L.) BENTH.ex HOOK. 2. Mitt. Isolierung weiterer Drevogenine Glykoside und Aglykone, 277. Mitteilung (1966) Helvetica Chimica Acta, 49, p. 1625
  • Ohno, Nishiyama, Nagase, (1979) Tetrahedron Letters, p. 4405

Citas:

---------- APA ----------
Cabrera, G., Seldes, A.M. & Gros, E.G. (1992) . A pregnane glycoside from the roots of Mandevilla pentlandiana. Phytochemistry, 32(1), 171-173.
http://dx.doi.org/10.1016/0031-9422(92)80126-Y
---------- CHICAGO ----------
Cabrera, G., Seldes, A.M., Gros, E.G. "A pregnane glycoside from the roots of Mandevilla pentlandiana" . Phytochemistry 32, no. 1 (1992) : 171-173.
http://dx.doi.org/10.1016/0031-9422(92)80126-Y
---------- MLA ----------
Cabrera, G., Seldes, A.M., Gros, E.G. "A pregnane glycoside from the roots of Mandevilla pentlandiana" . Phytochemistry, vol. 32, no. 1, 1992, pp. 171-173.
http://dx.doi.org/10.1016/0031-9422(92)80126-Y
---------- VANCOUVER ----------
Cabrera, G., Seldes, A.M., Gros, E.G. A pregnane glycoside from the roots of Mandevilla pentlandiana. Phytochemistry. 1992;32(1):171-173.
http://dx.doi.org/10.1016/0031-9422(92)80126-Y