Steroidal compounds in the roots of Asclepias tuberosa were investigated and 17α-hydroxyandrosta-4,6,15-trien-3-one 17-O-α-L-arabinopyranosyl-(1→6)-β-D-glucopyranoside, termed ascandroside, was isolated from the CHCl3-soluble fraction. Among five doubly-linked cardenolide glycosides, two were identified as 3'-spiro-linked thiazolidinone (4) and S-oxythiazolidinone derivatives (5) of Δ5-calotropin. The stereochemistry at the C-3' in these two cardenolides is discussed. 3'-O-β-D-glucopyranosyl-Δ5-calotropin (3) was also isolated along with Δ5-calotropin and its 3'-acetate. Nine glycosides of uzarigenin, coroglaucigenin and corotoxigenin were identified.
Asclepias tuberosa, androstane bioside, thiazolidinone-linked Δ5-calotropin, pleurisy root
NCBI PubMed ID: 10923828Publication DOI: 10.1248/cpb.48.991Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Correspondence: abefumi@fukuoka-u.ac.jp
Institutions: Faculty of Pharmaceutical Sciences, Fukuoka University, Fukuoka, Japan
Methods: 13C NMR, 1H NMR, IR, acid hydrolysis, GC, HPLC, UV, extraction, optical rotation measurement, CC, melting point determination, derivatization, HR-FAB-MS