Recurvosides A - E, new polyhydroxylated steroidal saponins from Nolina recurvata stems

A series of five new polyhydroxylated steroidal saponins, named recurvosides A - E, were isolated from the stems of Nolina recurvata (Agavaceae). Their structures were determined through detailed interpretation of various spectra, including two-dimensional (2D) NMR, and by acid-catalized hydrolysis....

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Published inTetrahedron Vol. 51; no. 8; pp. 2281 - 2292
Main Authors Takaashi, Yoko, Mimaki, Yoshihiro, Kuroda, Minpei, Sashida, Yutaka, Nikaido, Tamotsu, Ohmoto, Taichi
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 20.02.1995
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
GLYCOSIDES
CYCLIC-AMP PHOSPHODIESTERASE
OLIGOSACCHARIDES
BULBS
TRITERPENOID SAPONINS
NMR-SPECTROSCOPY
INHIBITORS
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Summary:A series of five new polyhydroxylated steroidal saponins, named recurvosides A - E, were isolated from the stems of Nolina recurvata (Agavaceae). Their structures were determined through detailed interpretation of various spectra, including two-dimensional (2D) NMR, and by acid-catalized hydrolysis. Among them, recurvoside E was revealed to be very unique in structure being a trisdesmoside with a β- d-fructofuranose as the monosaccharide component attached to the C-21 hydroxyl group of the aglycone. The isolated saponins were evaluated for inhibitory activity on cAMP phosphodiesterase as a primary screening test to find new biologically active compounds. The structures of recurvosides A ( 1) – E ( 5) were determined by extensive 2D NMR analysis and hydrolysis.
ISSN:0040-4020
1464-5416
DOI:10.1016/0040-4020(94)01098-K