Isotopologue Profiling of Triterpene Formation under Physiological Conditions. Biosynthesis of Lupeol-3-(3′-R-hydroxy)-stearate in Pentalinon andrieuxii

Abstract

The biosynthesis of lupeol-3-(3'R-hydroxy)-stearate (procrim b, 1) was investigated in the Mexican medicinal plant Pentalinon andrieuxii by (13)CO2 pulse-chase experiments. NMR analyses revealed positional enrichments of (13)C2-isotopologues in both the triterpenoid and the hydroxystearate moieties of 1. Five of the six isoprene units reflected a pattern with [1,2-(13)C2]- and [3,5-(13)C2]-isotopologues from the respective C5-precursors, IPP and DMAPP, whereas one isoprene unit in the ring E of 1 showed only the [3,5-(13)C2]-connectivity of the original C5-precursor, due to rearrangement of the dammarenyl cation intermediate during the cyclization process. The presence of (13)C2-isotopologues was indicative of [(13)C2]acetyl-CoA being the precursor units in the formation of the fatty acid moiety and of the triterpene via the mevalonate route. The observed labeling pattern was in agreement with a chair-chair-chair-boat conformation of the (S)-2,3-oxidosqualene precursor during the cyclization process, suggesting that the lupeol synthase from P. andrieuxii is of the same type as that from Olea europea and Taraxacum officinale, but different from that of Arabidopsis thaliana. The study shows that (13)CO2 pulse-chase experiments are powerful in elucidating, under in vivo conditions and in a single experiment, the biosynthesis of complex plant products including higher terpenes.

Spatio‐Temporal Variation of Terpenoids in Wild Plants of Pentalinon andrieuxii

“…) has stimulated an interest for understanding its biosynthetic origin. Initial attempts to incorporate labeled precursors into the sesquiterpenoid carbon have resulted in the isolation of labeled terpenoids but not of labeled UA , emphasizing the importance of learning more about the production dynamics of UA during plant development. The results of this investigation showed that, while UA could not be detected in root tissue during the first stage of plant development ( Fig.…”

Metabolic cross-talk between pathways of terpenoid backbone biosynthesis in spike lavender

“…However, metabolic cross-talk between the two pathways of terpenoid backbone biosynthesis is well documented (Bartram et al, 2006;Opitz et al, 2014;Peña-Rodríguez et al 2014;Rodriguez-Concepción and Boronat, 2015;Skorupinska-Tudek et al, 2008) (Figure 1). Therefore, the relative contribution of each pathway to the biosynthesis of the various classes of terpenes or even of a specific plant terpenoid remains uncertain and could depend on the given plant species or environmental conditions (Vranová et al, 2013).…”

Antimicrobial effects of the ginsenoside Rh2 on monospecies and multispecies cariogenic biofilms

“…Triterpene is formed from squalene via cyclization process involving the tail condensation of farnesol, which has been confirmed to have antibiofilm activity (Pena‐Rodriguez et al . ). Horev et al .…”

“…Ginseng extract ginsenosides are derived from a series of triterpenoid saponins compounds (Qu et al 2011). Triterpene is formed from squalene via cyclization process involving the tail condensation of farnesol, which has been confirmed to have antibiofilm activity (Pena-Rodriguez et al 2014). Horev et al (2015) reported that topical application of farnesol-loaded nanoparticles impeded biofilm formation by Streptococcus mutans and distinctly attenuated the virulence of this species in vivo and in vitro.…”