ABSTRACT
Ten phenanthrenes, two organic acids, one organic acid ester and one flavonoid were isolated from the aerial part of Juncus setchuensis by various chromatographic techniques usingsilica gel, polyamide, Sephadex LH-20 as solid phases, and preparative HPLC. Their structures were identified by MS and NMR spectroscopic data as effusol(1), juncusol(2), juncuenin D(3), dehydroeffusol(4), dehydrojuncusol(5), juncuenin B(6),dehydrojuncuenin B(7), 2-methoxyl-7-hydroxyl-1-methyl-5-vinyl phenanthrene(8), 2-hydroxyl-7-carboxy-1-methyl-5-vinyl-9,10-dihydrophenanthrene(9), 2-hydroxyl-7-carboxyl-1-methyl-5-vinylphenanthrene(10), luteolin(11), vanillic acid(12), daphnetin(13), p-coumaric acid(14), respectively. Compound 13 was isolated from the genus Juncus for the first time and compounds 5, 8-12 were isolated from J. setchuensis for the first time. The elevated plus-maze(EPM) was used to evaluate the anxiolytic activity of compounds 6 and 7. Compound 6 at 5 mg•kg⁻¹ and 10 mg•kg⁻¹ showed anxiolytic activity as well as compound 7 at 10 mg•kg⁻¹ and 20 mg•kg⁻¹.
ABSTRACT
Objective: To study the phenanthrenes from the pith of Juncus setchuensis. Methods: The compounds were separated and purified by column chromatographies amd their structures were elucidated by physicochemical properties and spectroscopic methods. Results: Five compounds were isolated from the 95% ethanol extract from the pith of J. setchuensis, their structures were determined as 8-hydroxymethyl-2-hydroxy-1-methyl-5-vinyl-9, 10-dihydrophenanthrene (1), 4-ethenyl-9, 10-dihydro-1, 8-dimethyl-2, 7-phenan-threnediol (2), effusol (3), dehydroeffusol (4), and 4-ethenyl-9, 10-dihydro-7-hydroxy-8-methyl-1-phenanthrenecarboxylic acid (5). Conclusion: Compound 1 is a new compound without literature report, named 8-hydroxymethyl-2-hydroxy-1-methyl-5-vinyl-9, 10-dihydrophenanthrene.
ABSTRACT
Objective: To rapidly recognize and identify phenanthrenes in Juncus effusus and J. setchuensis. Methods: HPLC-ESI-MS method was used to investigate the ESI-MS characteristics of those phenanthrenes, to screen, and to identify phenanthrenes in J. effusus and J. setchuensis. Results: Under negative mode, phenanthrenes were inclined to loss two hydrogens, which presumably caused by the cyclization of vinyl and aromatic ring; Furthermore, the loss of C=O could be also observed. Fragmentation pathway of phenanthrenes in ESI as a negative ion mode was summarized. Twenty-one phenanthrenes were rapidly detected from the extracts of J. effusus and J. setchuensis. Among them, six compounds were accurately identified by comparison with reference substances; The structures of five compounds were inferred according to their MS spectrum and polarity. Conclusion: HPLC-ESI-MS provides not only a new technique for the rapid identification of phenanthrenes from complex matrix, but also an effective method for the target separation of constituents in Chinese materia medica.