Monoterpene, benzyl and 3,4-dihydroxyphenethyl glycosides from Magnolia thailandica

Abstract

A new monoterpene glucoside, (3S,6S)-6,7-dihydroxy-6,7-dihydrolinaloyl 6-O-β-d-glucopyranoside, along with two new aromatic glycosides, benzyl O-α-l-rhamnopyranosyl-(1 → 2)-β-d-glucopyranoside and 3,4-dihydroxyphenethyl O-α-l-rhamnopyranosyl-(1 → 2)-[α-l-rhamnopyranosyl−(1 → 3)]-β-d-glucopyranoside were isolated from Magnolia thailandica. Additionally, 29 known compounds, (3S,6R)-6,7-dihydroxy-6,7-dihydrolinaloyl 6-O-β-d-glucopyranoside, benzyl O-β-d-glucopyranoside, benzyl O-β-d-apiofuranosyl-(1 → 2)-β-d-glucopyranoside, icariside F2, benzyl O-β-d-apiofuranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 3)]-β-d-glucopyranoside, vanillic acid β-d-glucopyranosyl ester, 3-​hydroxy-​4,​5-​dimethoxyphenyl-​β-​D-​glucopyranoside, 3,4,5-trimethoxyphenyl-β-d-apiofuranosyl-(1 → 6)-β-d-glucopyranoside, icariside D2, 2-hydroxy-5-(2-hydroxyethyl)phenyl β-d-glucopyranoside, decaffeoylverbascoside, verbascoside, isoverbascoside, crassifolioside, isocrassifolioside, echinacoside, 2′-rhamnoechinacoside, syringin, syringinoside, isosyringinoside, icariside E5, (+)-pinoresinol-β-d-glucopyranoside, isoeucommin A, (+)-syringaresinol O-β-d-glucopyranoside, kaempferol 3-O-rutinoside, kaempferol 3-O-α-l-rhamnopyranosyl-(1 → 2)-[α-l-rhamnopyranosyl-(1 → 6)]-β-d-glucopyranoside, rutin, (6S,9S)-roseoside, and citroside A were identified. The structure elucidation of these compounds was based on analyses of physical and spectroscopic data including 1D and 2D NMR experiments.