Bioorganic research of Galactites tomentosa Moench. Honey extracts: enantiomeric purity of chiral marker 3-phenyllactic acid.

Thistle (Galactites tomentosa Moench.) honey organic extracts were obtained by headspace solid-phase microextraction (HS-SPME) and ultrasonic solvent extraction (USE) and analyzed by gas chromatography (GC-FID and GC-MS) for the first time. Most abundant headspace compounds were terpenes, particularly linalool derivatives (hotrienol was predominant with a range of 38.6-57.5%). 3-Phenyllactic acid dominated in the solvent extracts (77.4-86.4%) followed by minor percentages of other shikimate pathway derivatives. After determination of an adequate enantioseparation protocol on Chirallica PST-4 column, the honey solvent extracts were analyzed by high-performance liquid chromatography (HPLC). The chiral analysis revealed high enantiomeric excess (>95%) of (-)-3-phenyllactic acid in all samples. Therefore, previous findings of chemical markers of thistle honey were extended, providing new potential for advanced chemical fingerprinting (optical pure chemical marker).

Bioorganic diversity of rare Coriandrum sativum L. honey: unusual chromatographic profiles containing derivatives of linalool/oxygenated methoxybenzene.

The compounds responsible for highly individual aroma profile of Coriandrum sativum L. honey were isolated by headspace solid-phase microextraction (HS-SPME; used fibers: A: polydimethylsiloxane (PDMS)/divinylbenzene (DVB) and B: divinylbenzene/carboxen/polydimethylsiloxane), as well as ultrasonic solvent extraction (USE; used solvents: A: pentane/Et2 O 1 : 2 (v/v) and B: CH2 Cl2 ) and analyzed by gas chromatography (GC) and mass spectrometry (MS). Unusual chromatographic profiles were obtained containing derivatives of linalool/oxygenated methoxybenzene. trans-Linalool oxide (11.1%; 14.6%) dominated in the headspace, followed by other linalool derivatives (such as cis/trans-anhydrolinalool oxide (5.0%; 5.9%), isomers of lilac aldehyde/alcohol (14.9%; 13.8%) or p-menth-1-en-9-al (15.6%; 18.5%)), octanal, and several low-molecular-weight esters. The major compounds in the solvent extracts were oxygenated methoxybenzene derivatives such as 3,4,5-trimethoxybenzyl alcohol (26.3%; 24.7%), methyl syringate (23.8%; 11.7%), and 3,4-dimethoxybenzyl alcohol (5.6%; 13.9%). Another group of abundant compounds in the extracts were derivatives of linalool (e.g., (E)/(Z)-2,6-dimethylocta-2,7-diene-1,6-diol (17.8%; 16.1%)). Among the compounds identified, cis/trans-anhydrolinalool oxides and 3,4,5-trimethoxybenzyl alcohol can be useful as chemical markers of coriander honey.