GC-MS analysis of penta- and tetra-cyclic triterpenes from resins of Pistacia species. Part I. Pistacia lentiscus var. Chia
A. N. Assimopoulou and V. P. Papageorgiou*
Organic Chemistry Laboratory, Department of Chemical Engineering, Aristotle University of
Thessaloniki, 541 24, Greece
Pistacia species contain oleoresins with bioactive triterpenes. In this study triterpenes, including minor components, were identified and quantified in both neutral and acidic fraction of Pistacia lentiscus var. Chia resin, grown exclusively in Chios island (Greece), collected traditionally, as well as by the use of stimulating agents (liquid collection). It was proved that these two resin samples were composed of several different minor triterpenes. In the traditional collection of the resin, 36 triterpenes were identified, 23 of which are new minor compounds (five in the acidic and eighteen in the neutral fraction). In the liquid collection resin eight compounds were identified in the acidic and 11 in the neutral fraction, while seven compounds were not contained in resin traditionally collected. The main triterpenes in both resin samples collected traditionally and by use of stimulating agents were in the following order: isomasticadienonic acid (24 and 22.5% w/w of triterpenic fraction respectively), masticadienonic acid (9.3 and 14.7% w/w of triterpenic fraction) and 28-norolean-17-en-3-one (19 and 36% w/w of triterpenic fraction respectively).The aim of this study was to compare the qualitative and quantitative composition of triterpenes in the resin samples collected using the traditional and new liquid techniques, and examine whether the collection technique influences the contained triterpenes in P. lentiscus var. Chia resin samples. Finally, since there is confusion on interpreting mass spectra of triterpenes we present an analytical review on the base peaks, main fragments and fragmentation mechanism/pattern of several skeleton penta- and tetracyclic triterpenes reported in P. lentiscus resin. Also, a biosynthetic route for triterpene skeletons contained in P. lentiscus resin was approached.
Keywords: triterpenes; Pistacia; Helicobacter pylori; oleanane; tirucallane; dammarane; varnishes; oleanolic acid; mass spectra;
mastic gum; terpenes; terpenoids; resin