Studies on Monoterpene Glucosides. XII. Biosynthesis of Gentianaceous Secoiridoid Glucosides

Biosynthesis significance of iridoids in chemosystematics

“…21 Incorporation of 7-3 H-loganin (17) into secologanin (18) and into strictosidine (19) in Catharanthus roseus (Apocynaceae) corroborates that secologanin was formed via loganin 22 . In other studies on the subject it has been shown that secoiridoids are formed through this biosynthetic route 3,25,26 . The iridolactone gibboside (20) is biosynthetized in Patrinia gibbosa from the 10 27 .…”

Chemotaxonomy and pharmacology of Gentianaceae

“…6.1 shown as mevalonolactone) to Swertia caroliniensis gave incorporation into gentiopicroside (7; Coscia & Guarnaccia, 1967). Inouye et al (1967Inouye et al ( , 1970 simultaneously showed incorporation of mevalonolactone into 7 in Gentiana triflora and into sweroside (5) and swertiamarin (6) in Swertia japonica. Since the incorporation into 5 was ten times higher than that into 6, the former was suggested to be a precursor of the latter.…”

Chromatographic Evaluation and Characterization of Components of Gentian Root Extract Used as Food Additives

“…The EtOAc, n-BuOH, and water extracts, which contained aromatic compounds as assessed by HPLC, were separately chromatographed using YMC gel ODS-AQ, Sephadex LH-20, and/or Chromatorex ODS with methanol (MeOH) [or ethanol (EtOH)]-H 2 O in stepwise gradient mode. The fractions showing similar HPLC patterns were combined and further purified by column chromatography, to afford loganic acid 7-(2′-hydroxy-3′-O-β-D-glucopyranosyl)benzoate (1), together with 5-hydroxymethyl-2-furfural (2), 12) furan-2-carboxylic acid (3), 13) 2,3-dihydroxybenzoic acid (4), 14) gentiopicroside (5), 5) isovitexin (6), 15) gentisin 7-O-primeveroside (7), 7) isogentisin 3-O-primeveroside (8), 16) a mixture of gentisin (9) and isogentisin (10), 4) vanillic acid (11), 17) loganic acid (12), 4) sweroside (13), 15) 6′-O-glucosylgentiopicroside (14), 16) and swartiajaposide D (15). 18) The n-hexane extract was dissolved in acetone and subjected to preparative TLC to give anofinic acid (16) and 2-methoxyanofinic acid (17), 4) The known compounds were identified by direct comparison with authentic specimens or by spectral comparison with data reported in the literature (Fig.…”

“…20) Since gentiopicroside (5) was detected as the main constituent and amarogentin could not be detected owing to its level being below the detection limit, gentiopicroside (5) was considered the primary contributor to the bitter taste of the gentian root. Previously, amarogentin was reported to be one of the main bitter components of gentian 2,6) ; however, its content decreases over the cultivation period.…”

“…3) Previously, phytochemical studies of this drug revealed the presence of bitter secoiridoid glycosides, including gentiopicroside, swertiamarin, and amarogentin, [4][5][6] xanthones, 7) phenolic acids, 8) flavonoids, 9) and triterpenoids. 10,11) Notably, water or ethanolic extract of the gentian root and rhizome is used to impart a bitter taste to liqueurs.…”