Megastigmane, Benzyl and Phenethyl Alcohol Glycosides, and 4, 4'-Dimethoxy-β-truxinic Acid Catalpol Diester from the Leaves of Premna subscandens MERR

• Published in: Chemical & pharmaceutical bulletin Vol. 48; no. 4; pp. 542 - 546
• Main Authors: SUDO, Hirokazu, IDE, Toshinori, OTSUKA, Hideaki, HIRATA, Eiji, TAKUSHI, Anki, SHINZATO, Takakazu, TAKEDA, Yoshio
• Format: Journal Article
• Language: English
• Published: TOKYO The Pharmaceutical Society of Japan 2000; Pharmaceutical Soc Japan
• Subjects: 4, 4'-dimethoxy-β-truxinic acid catalpol ester; Acetylation; benzyl alcohol glycoside; Chemistry; Chemistry, Medicinal; Chemistry, Multidisciplinary; Cyclobutanes - chemistry; Cyclobutanes - isolation & purification; Cyclohexanols - chemistry; Cyclohexanols - isolation & purification; Furans - chemistry; Furans - isolation & purification; Glucosides - chemistry; Glucosides - isolation & purification; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; megastigmane glycoside; Models, Chemical; Pharmacology & Pharmacy; phenethyl alcohol glycoside; Physical Sciences; Plant Extracts - chemistry; Plant Leaves - chemistry; Premna subscandens; Science & Technology; Spectrometry, Mass, Fast Atom Bombardment; Verbenaceae; IRIDOID GLUCOSIDES; Verbenaceae; benzyl alcohol glycoside; phenethyl alcohol glycoside; 4,4 '-dimethoxy-beta-truxinic acid catalpol ester; megastigmane glycoside; Premna subscandens
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.48.542

Extensive isolation work on the n-BuOH-soluble fraction obtained from the leaves of Premna subscandens, collected on Ishigaki island, Okinawa, afforded six compounds. Two were identified as megastigmane glucosides, 7-(3, 5-dihydroxy-1, 1, 5-trimethylcyclohexylidene)-9-methylprop-8-enyl 9-O-β-ionol 9-O-β-D-glucopyranoside and 3-hydroxy-5, 6-epoxy-β-D-glucopyranoside. The structures of the remaining four new compounds were elucidated to be a 2'-O-β-D-apiofuranosyl derivative of 3-hydroxy-5, 6-epoxy-β-ionol 9-O-β-D-glucopyranoside, named premnaionoside, benzyl alcohol β-D-(2'-O-β-D-xylopyranosyl)glucopyranoside, phenethyl alcohol β-D-(2'-O-β-D-glucopyranosyl)glucopyranoside, and 4, 4'-dimethoxy-β-truxinic acid catalpol diester by spectroscopic analyses.