6-Carboxydihydroresveratrol 3-O-β-glucopyranoside — A novel natural product from the Cretaceous relict Metasequoia glyptostroboides

• Published in: Fitoterapia Vol. 95; pp. 109 - 114
• Main Authors: Nguyen, Xuan Hong Thy, Juvik, Ole Johan, Øvstedal, Dag Olav, Fossen, Torgils
• Format: Journal Article
• Language: English
• Published: Netherlands Elsevier B.V 01.06.2014
• Subjects: 2D NMR; 6-Carboxydihydroresveratrol 3-glucoside; Bibenzyl; Biological Assay; Biological Products; Biphenyl Compounds - pharmacology; Cupressaceae - chemistry; Free Radical Scavengers - chemistry; Free Radical Scavengers - isolation & purification; Free Radical Scavengers - pharmacology; Glucosides - chemistry; Glucosides - isolation & purification; Glucosides - pharmacology; Lipoxygenase Inhibitors - chemistry; Lipoxygenase Inhibitors - isolation & purification; Lipoxygenase Inhibitors - pharmacology; Magnetic Resonance Spectroscopy; Mass Spectrometry; Metasequoia glyptostroboides; Molecular Structure; Picrates - pharmacology; Plant Leaves - chemistry; Plants, Medicinal; Stilbenes - chemistry; Stilbenes - isolation & purification; Stilbenes - pharmacology; Trees; Bibenzyl; 6-Carboxydihydroresveratrol 3-glucoside; 2D NMR; Metasequoia glyptostroboides
• ISSN: 0367-326X; 1873-6971
• DOI: 10.1016/j.fitote.2014.03.001

Metasequoia glyptostroboides, a tree native to China, is described as a living fossil and has existed for millions of years. The oldest fossils recorded have been dated to the late Cretaceous era. During the time of its existence, the molecular defence system of the tree has apparently resisted millions of generations of pathogens, which encouraged search for novel natural product from this source. Eight compounds have been characterised from needles of M. glyptostroboides, including the novel natural product 6-carboxydihydroresveratrol 3-O-β-glucopyranoside. The structure determinations were based on extensive use of 2D NMR spectroscopic techniques and high-resolution mass spectrometry. Eight compounds including the novel natural product 6-carboxydihydroresveratrol 3-O-β-glucopyranoside was characterised from needles of Metasequoia glyptostroboides. [Display omitted]