Structures of eremophilane-type sesquiterpene glucosides, alticolosides A–G, from the Far Eastern endemic Ligularia alticola Worosch. (March 2015)

• Record Type: Journal Article
• Authors: Silchenko, Alexandra S.; Kalinovsky, Anatoly I.; Ponomarenko, Ludmila P.; Avilov, Sergey A.; Andryjaschenko, Pelageya V.; Dmitrenok, Pavel S.; Gorovoy, Peter G.; Kim, Natalia Yu.; Stonik, Valentin A.
• Is Part Of: Phytochemistry. Volume 111(2015:Mar.)
• Page Start: 169
• Page End: 176
• Publication Date: 2015-03
• Subjects: Ligularia alticola -- Sesquiterpene eremophilane-type glycosides -- Alticolosides -- NMR; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2014.11.003
• Languages: English
• ISSNs: 0031-9422

Abstract

Graphical abstract: Highlights: We first investigated the chemical constituents from the aerial parts of Far Eastern endemic plant Ligularia alticola Woroch. Seven sesquiterpene eremophilane-type glucosides have been isolated and their structures elucidated. Six compounds were novel and five of them contained aglycones having new chemical structures including stereostructures. Abstract: Seven eremophilane-type sesquiterpene glucosides, alticolosides A–G, have been isolated from aerial parts of the endemic Far Eastern species Ligularia alticola Worosch. (Family Asteraceae) along with two known compounds, monoterpenoid glycoside (4S)-α-terpineol 8- O -β-d -glucopyranoside and norditerpenoid glycoside 7(8)-dihydro-β-ionone 3- O -β-d -glucopyranoside. Alticoloside D was identified with the earlier known 8- O -(β-d -glucopyranosyl)-2-oxo-eremophila-1(10), 8, 11-triene, but the stereostructure of the latter was revised on the basis of ROESY and CD data. All the glycosides are derivatives of new eremophilane-type aglycones, differing from known eremophilanes in details of planar and/or stereo structures except for the aglycone of alticoloside E.