54835-70-0Relevant articles and documents
A simple synthesis of four stereoisomers of roseoside and their inhibitory activity on leukotriene release from mice bone marrow-derived cultured mast cells
Yajima, Arata,Oono, Yutaka,Nakagawa, Ryusuke,Nukada, Tomoo,Yabuta, Goro
, p. 189 - 194 (2009)
Four stereoisomers of roseoside (vomifoliol glucosides) were synthesized using glucose as a chiral resolving reagent. The four synthetic stereoisomers exhibited inhibitory activity on leukotriene release from mouse bone marrow-derived cultured mast cells (BMCMC). The (6S)-isomers of roseoside were about twice as active as (6R)-isomers.
Characterization of caffeoylglucoside derivatives and hypouricemic activity of the ethyl acetate fraction from Aster glehni
Son, Min Jeoung,Jin, Changbae,Lee, Yong Sup,Lee, Jae Yeol,Kim, Hyoung Ja
, p. 503 - 512 (2015/05/06)
In the search for xanthine oxidase (XOD) inhibitors as anti-gout agents from natural products, various chromatographic separations of the ethyl acetate-soluble fraction of Aster glehni (AGEF) led to the isolation of five new caffeoylglucoside derivatives, namely 6′-O-caffeoyl-(6S,9R)-roseoside (1), 6′-O-caffeoylampelopsisionoside (2), 6′-O-caffeoylsonchuinoside C (3), 6′-O-caffeoyldihydrosyringin (4), and (2E)-2-methyl-but-2-ene-1,4-diol-6′-O-caffeoyl-1-O-β-glucopyranoside (glehnoside, 5), together with 13 known compounds. The absolute stereochemistry of the 6′-O-caffeoylsonchuinoside C (3) was established with the help of spectroscopic analyses, enzymatic hydrolysis, and Mosher's method, as well as in comparison with literature data. All isolated substances were determined for their inhibitory activities on uric acid production by the xanthine/XOD system. Among them, 4,5-O-dicaffeoylquinic acid methyl ester (12) showed the most potent inhibitory activity with an IC50 value of 2.6 ± 0.1 μM, which was comparable to that of allopurinol used as a positive control. Furthermore, hypouricemic effects of AGEF were assessed by measuring serum uric acid levels 3 h after potassium oxonate treatment (250 mg/kg, i.p.) to induce hyperuricemia in rats. When preadministered orally once a day at doses of 50, 100, and 300 mg/kg for 7 days, AGEF reduced the potassium oxonate-induced elevated serum uric acid level by 15.4, 39.8, and 32.3%, respectively. The results suggest that AGEF has the potential to be a new source of agents for the prevention and/or treatment of hyperuricemia and gout.
Synthesis of optically active vomifoliol and roseoside stereoisomers
Yamano, Yumiko,Ito, Masayoshi
, p. 541 - 546 (2007/10/03)
A synthesis of optically active vomifoliol stereoisomers 1-4 and their glucosides, roseoside stereoisomers 5-8, was accomplished via α-acetylenic alcohol 11a or 11b effectively prepared by an asymmetric transfer hydrogenation of α,β-acetylenic ketone 10. Simultaneous separation of these stereoisomers by HPLC was also perfomed.
Glycosidically Bound Norisoprenoids from Vitis vinifera Cv. Riesling Leaves
Skouroumounis, George K.,Winterhalter, Peter
, p. 1068 - 1072 (2007/10/02)
HRGC and HRGC-MS identifications of glycosidically bound Riesling leaf constituents were achieved after extraction with MeOH, Amberlite XAD-2 adsorption, and subsequent enzymatic hydrolysis of the glycoconjugates.Among the enzymatically liberated aglycons 23 bound C13 norisoprenoids were identified.With the aid of multilayer coil countercurrent chromatography (MLCCC) five major C13 glycosides were purified, and their structures were elucidated by high-field NMR, i.e., the β-D-glucopyranosides of vomifoliol, 4,5-dihydrovomifoliol, 3-hydroxy-5,6-epoxy-β-ionone, grasshopper ketone, and 3-oxo-megastigman-9-ol.The latter glucoside with a saturated megastigmane skeleton is reported here for the first time.In addition, the β-D-glucopyranosides of benzyl alcohol and raspberry ketone have been isolated.
