Chemistry and chemotaxonomy of Pterophyten. LXII Ingredients of Arachniodes maximowiczii Ohwi.

Abstract

Two new ent-rosane type norditerpenes, ar-maximic acid (I) and ar-maximol (II), were isolated from the fronds of Arachniodes maximowiczii OHWI, and were shown to have the structures of 2-hydroxy-19-nor-ent-rosa-1, 3, 5(10), 15(16)-tetraene 18-oic acid (I) and 2, 18-dihydroxy-19-nor-ent-rosa-1, 3, 5(10), 15(16)-tetraene (II) by chemical, spectroscopic and X-ray crystallographic methods. In addition, six glycosides of acyclic terpenes were isolated, and their structures were elucidated as 3(S)-linalool O-β-D-glucopyranoside (III), 3(S)-linalool O-β-D-(6'-O-β-L-fucopyranosyl)glucopyranoside (IV), 13-hydroxygeranyllinalool 13-O-β-D-(6'-O-β-L-fucopyranosyl)glucopyranoside (V), 13-hydroxygeranyllinalool 3, 13-O-β-D-diglucopyranoside (VI), 13-methoxygeranyllinalool O-β-D-glucopyranoside (VII) and 15-methoxy-3, 7, 11, 15-tetramethylhexadeca-1, 6(E), 10(E), 13(E)-tetraene O-β-D-glucopyranoside (VIII), mainly by spectroscopic methods. Compounds VII and VIII, obtained as an inseparable mixture may be artefacts. Maltol and maltol β-D-glucoside were also isolated.