Spinonin, a novel glycoside from Ononis spinosa subsp. leiosperma.
The roots of Ononis spinosa subsp. leiosperma (Leguminosae) afforded a new glycoside, spinonin (1), possessing a novel skeleton, in addition to the known isoflavonoid glycoside, ononin [7beta-(glucosyloxy)formononetin] (2) and the known pterocarpan, 7-demethoxy-7-D-(glucosyloxy)homopterocarpin (3). The structure of the new isolate was elucidated by spectral methods including 1H and 13C NMR, COSY, APT, HETCOR, HMBC, NOESY, CD, FABMS, HRMS, EIMS, CIMS, and some chemical reactions. Spinonin was inactive against a number of human cancer cell lines and HIV-1 reverse transcriptase. The compounds 1 and 3 showed weak activity against Pseudomonas aeruginosa, whereas 2 was active against beta-hemolytic Streptococcus.
Kirmizigül
S
S
Department of Organic Chemistry, Faculty of Science, Ege University, Izmir, Turkey.
Gören
N
N
Yang
S W
SW
Cordell
G A
GA
Bozok-Johansson
C
C
D000107:Acetylation; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D054303:HIV Reverse Transcriptase / Q000378:metabolism*; D006801:Humans; D006868:Hydrolysis; D008745:Methylation; D008826:Microbial Sensitivity Tests; D010636:Phenols / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018894:Reverse Transcriptase Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D014407:Tumor Cells, Cultured
D000900:Anti-Bacterial Agents; D000972:Antineoplastic Agents, Phytogenic; D005960:Glucosides; D010636:Phenols; D018894:Reverse Transcriptase Inhibitors; C106017:spinonin; D054303:HIV Reverse Transcriptase