Structures of New and Known Cyanoglucosides from a North American Plant, Purshia tridentata DC

• Published in: Chemical & pharmaceutical bulletin Vol. 42; no. 11; pp. 2251 - 2255
• Main Authors: NAKANISHI, Tsutomu, NISHI, Masatoshi, SOMEKAWA, Midori, MURATA, Hiroko, MIZUNO, Mizuo, IINUMA, Munekazu, TANAKA, Toshiyuki, MURATA, Jin, LANG, Frank A., INADA, Akira
• Format: Journal Article
• Language: English
• Published: TOKYO The Pharmaceutical Society of Japan 1994; Pharmaceutical Soc Japan; Maruzen; Japan Science and Technology Agency
• Subjects: Analytical, structural and metabolic biochemistry; Biological and medical sciences; Carbohydrates; Chemistry; Chemistry, Medicinal; Chemistry, Multidisciplinary; cyanoglucoside; difference nuclear Overhauser effect spectrum; Fundamental and applied biological sciences. Psychology; Life Sciences & Biomedicine; menisdaurin; Miscellaneous; Other biological molecules; Pharmacology & Pharmacy; Physical Sciences; Purshia tridentata; purshianin; Rosaceae; Science & Technology; MENISDAURIN; CYANOGLUCOSIDE; ROSACEAE; PURSHIA TRIDENTATA; GLUCOSIDE; PURSHIANIN; DIFFERENCE NUCLEAR OVERHAUSER EFFECT SPECTRUM; Nitrile; Rosaceae; Alcohol; Dienic compound; Stem; Dicotyledones; Angiospermae; Absolute configuration; Plant origin; Isolation; Spermatophyta; Glycoside; Monocyclic compound; Structural analysis
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.42.2251

A new cyanoglucoside, purshianin (1), was isolated together with a known cyanoglucoside, menisdaurin (2a), from stems of Purshia tridentata DC. (Rosaceae) collected in Oregon, U.S.A. and the structure was established as (4S, 6S)-(Z)-6-(β-D-glucopyranosyloxy)-4-hydroxy-2-cyclohexene-Δ1, α-acetonitrile (1) based on chemical and spectral evidence. Notably, the absolute structure of 1 and the revised stereostructure (2), (4S, 6R)-(Z)-6-(β-D-glucopyranosyloxy)-4-hydroxy-2-cyclohexene-Δ1, α-acetonitrile for menisdaurin were decided based on combined studies of difference NOE spectra and Dreiding model inspection.