One‐step multiple component isolation from the oil of Crinitaria tatarica (Less.) Sojak by preparative capillary gas chromatography with characterization by spectroscopic and spectrometric techniques and evaluation of biological activity

Abstract

Gas chromatographic analysis revealed that the oil of Crinitaria tatarica was rich in sabinene (32.1%), β-pinene (8.8%), and two unknown (M+200) compounds (I) and (II) (21.4% and 3.4%). One-step multiple fractionation of the oil and separation of two unknown constituents were performed using preparative capillary gas chromatography connected to preparative fraction collector system. This combination allowed separation and recover of sufficient quantities of two unknown compounds with high purity from complex oil matrix. Separation conditions (column temperature, cooling temperature, flow rate, injection volume, cut time) were optimized to achieve the best isolation and successful collection. The target compounds were separated from the oil using a HP Innowax (Walt & Jennings Scientific, Wilmington, DE, USA) preparative capillary column in rapid one-step manner with 95.0% purity. Trapping of the isolated compounds in collector system was facilitated by cooling with liquid nitrogen. Structure determination was accomplished by spectral analysis including ultraviolet, nuclear magnetic rezonance, and high-resolution electrospray ionization mass spectrometry. Z- (I) and E-artemidin (II) were isolated for the first time from this species. Crinitaria tatarica oil and Z- (I) and E-artemidin (II) were evaluated for biological activity.

Evolution and status of preparative gas chromatography as a green sample-preparation technique

“…In 2012, Ozek et al [30] performed a one-step multiple fractionation of Crinitaria tatarica oil and separation of two unknown constituents (Z-and E-artemidin) isolated from this species for the first time (Fig. 2).…”

“…Prep-GC methods were also used for the collection of enantiomeric pure components exploiting derivatized cyclodextrins as chiral selectors [13]. Often, a prep-GC analysis precedes a 1 H nuclear magnetic resonance (NMR) [19,22,25,27,28,30,35,37] and 14 C and 13 C analysis [29,33]. Codina et al [22] isolated three pharmaceutical impurities (A, B and C), further characterized by means of 1D and 2D NMR experiments.…”

“…Prep-GC methods were recently employed for various purposes, such as the isolation of structural isomers present in complex mixtures [27,37]:  pure substances in the fields of flavor and fragrance [26,28,30,31,35,36] and the environment [21,24,27];  impurities in pharmaceutical products [22]; and,  trace amounts of essential oil components for the assessment of organoleptic properties [23,25,30]. Prep-GC methods were also used for the collection of enantiomeric pure components exploiting derivatized cyclodextrins as chiral selectors [13].…”

“…Sample introduction in a prep-GC system is commonly carried out in splitless mode [19,23,30,31,37] or in large-volume conditions by means of a programmed temperature vaporization (PTV) injector [22,29,46], both often in multi-injection mode. In conventional GC analysis, splitless mode is commonly exploited to allow the introduction of diluted samples to meet the detector sensitivity, while, in prep-GC, the goal is the introduction of greater amounts of sample.…”

“…Since 2010, reviews, mainly based on packed columns [15] or generally on natural-product isolation [16], books [17][18][19] and applications of prep-GC in different fields have been reported using capillary columns [20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37], directly connected to a preparative station or exploiting a heart-cut step with a Deans switch (DS) device at the end of the GC column to allow switching between detector and sample collector [19,27,28,31,[35][36][37]. Furthermore, at least four patents were published in PCGC [38][39][40][41].…”