Sensitive monitoring of monoterpene metabolites in human urine using two-step derivatisation and positive chemical ionisation-tandem mass spectrometry

R-Limonene metabolism in humans and metabolite kinetics after oral administration

“…The internal standard substance (-)-D 4 -menthol [D 4 -MNT; 1,2,6,6-2 H 4 -(-)-5-methyl-2-(1-methylethyl)-cyclohexanol; 98 %] was obtained from Cambridge Isotope Laboratories, Inc. (Andover, MA, USA). Limonene-8,9-diol [(2RS)-2-[(1R)-4-methyl-3-cyclohexene-1-yl]-propan-1,2-diol; >99 %], 13 CD 2 -perillic acid [(4S)-4-(1-methylethenyl-2-13 C-2,2-2 H 2 )-1-cyclohexene-1-carboxylic acid; 99 %; isotopic purity: 90 %; 13 CD 2 -PA), 13 CD 3 -(1S,2S,4R)-limonene-1,2-diol [(1S,2S,4R)-9-13 C 2 H 3 -1-methyl-4-(1-methylethenyl)-cyclohexane-1,2-diol; 99 %; isotopic purity: 99 % 13 C; 99.5 % 2 H; 13 CD 3 -LMN-1,2-OH]; 13 CD 3 -(1S,2S,4R)-limonene-1,2-diol [(1R,2R,4R)-9-13 C 2 H 3 -1-methyl-4-(1-methylethenyl)-cyclohexane-1,2-diol; 99 %; isotopic purity: 99 % 13 C; 99.5 % 2 H; 13 CD 3 -(1R,2R,4R)-LMN-1,2-OH], and 13 CD 3 -limonene-8,9-diol [(2RS)-9-13 C 2 H 3 -2-[(1R)-4-methyl-3-cyclohexene-1-yl]-propane-1,2-diol; 99 %; isotopic purity: 99 % 13 C; 99.5 % 2 H; 13 CD 3 -LMN-8,9-OH] were synthesised as described earlier (Schmidt et al 2013). Dichloromethane (>99 %; DCM), acetonitrile (>99 %), isooctane (>99 %), and aqueous hydrochloric acid (HCl; 25 %, p.a.)…”

“…The urine samples were analysed according to our previously published procedure (Schmidt et al 2013). Following this procedure, the urine samples were enzymatically hydrolysed for 12 h with β-glucuronidase/arylsulphatase, acidified with HCl, and extracted by solid-supported liquid-liquid extraction (SSLLE) using dichloromethane (DCM).…”

“…After silylation with BSTFA and TSIM, the extracts were analysed by gas chromatography coupled with positive chemical ionisation tandem mass spectrometry (GC-PCI-MS/MS). Detailed information on analysis and calibration as well as reliability data is given in Schmidt et al (2013). For blood analysis, the standard procedure was modified with regard to sample preparation as described in Schmidt and Göen (2016).…”

Development and Validation of a Stability-Indicating Method for Perillyl Alcohol Incorporated in Poly(lactide-co-glycolide) Nanoparticles and Stress Degradation Studies

“…The most common technique used is the gas chromatography coupled to mass spectrometry (GC-MS) for both biological matrices such as plasma and urine, and non-biological matrices such as the volatile fraction of plant extracts. [19][20][21][22][23][24] Methods by liquid chromatography (LC) techniques are also described in the literature, such as liquid chromatography-diode array detection (LC-DAD), [25][26][27][28][29] liquid chromatographyelectrochemical detection (LC-ECD) 30 and liquid chromatography-fluorescence detection (LC-FLD). 31 These papers are devoted to describing chromatographic methods for analytical and bioanalytical quantification of POH, and none of these cases comprise a degradation behavior study.…”

Monocyclic and bicyclic monoterpenes in air of German daycare centers and human biomonitoring in visiting children, the LUPE 3 study

“…For αPN, mono-hydroxylated structures such as cis-and trans-verbenol (cVER and tVER) are predominant metabolites (Eriksson and Levin, 1990;Ishida et al, 1981;Southwell et al, 1980), however for LMN, cis-and trans-carveol (cCAR and tCAR) as well as perillyl alcohol (POH) are minor ones ( Fig. 1) (Schmidt et al, 2013). Unlike LMN and αPN, the human metabolism of CRN is still poorly explored.…”