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Angelica is a large genus of plants belonging to the Apiaceae family that includes about 100 species of biennial or perennial herbs. Several species of this genus are extensively used in various traditional medicines and, despite their content in toxic furanocoumarins, also as food. In this study, the chemical composition of the essential oil (EO) from aerial flowering parts of Angelica sylvestris L., a plant distributed in Europe, North and Central Asia, collected in the Isle of Skey (Scotland), was analyzed by GC and GC-MS. No one report has been previously published on this accession. The result showed the presence of a large quantity of monoterpene hydrocarbons with limonene (51.89%), by far, as the most abundant component. Other metabolites present in lesser quantity were β -pinene (4.61%), α- pinene (3.54%), and thymol (3.33%). Considerations with respect to all the other EOs of A. sylvestris taxa, studied so far, were carried out.

Aims: The aims of this article were to select fungal species with high tolerance and high growth rate in mediums supplemented with limonene and citrus essential oils (CEOs), and to test the bioconversion capability of the chosen isolates for the bioproduction of aroma compounds., Methods and Results: Based on the use of predictive mycology, 21 of 29 isolates were selected after assaying R-(+)-limonene and CEO tolerance (10 g l -1 ). With a dendrogram divisive coefficient of 0·937, the subcluster two with isolates Aspergillus niger LBM 055, Penicillium sp. LBM 150, Penicillium sp. LBM 151 and Penicillium sp. LBM 154 gathered the highest tolerance and mycelia growth speed. Ultrastructural analysis indicated that culture media containing limonene had no visible toxic activity that could promote morphological changes in the fungal cell wall. The biomass of A. niger LBM055 was distinctive in liquid media supplemented with R-(+)-limonene (0·57 ± 0·07 g) and it was selected to prove bioconversion capacity, under static and agitated conditions, and converted up to 98% of limonene, yielding a wide variety of products that were quantified by GC-FID. It was obtained at molecular weights less than limonene (64-100%), between limonene and α-terpineol (12-72%) and greater than α-terpineol (2-48%)., Conclusions: Aspergillus niger LBM 055, Penicillium sp. LBM 150, Penicillium sp. LBM 151 and Penicillium sp. LBM 154 showed to the highest tolerance and growth rate in mediums supplemented with R-(+)-limonene and orange and lemon essential oils. Particularly, A. niger LBM055, showed limonene bioconversion capability and produced different molecular weights compounds such us α-terpineol., Significance and Impact of the Study: Different bioproducts can be obtained by changing operative condition with the same fungus, and this bioprocess aspect is a significant approach to be adopted on industrial scale leading to the creation of new natural flavours and fragrance compositions., (© 2020 The Society for Applied Microbiology.)

The aim of this study was to determine, first, the chemical composition of Aloysia polystachya (Griseb) Moldenke essential oil, from leaves harvested in central Chile; and second, its antioxidant and cytotoxic activity. Eight compounds were identified via gas chromatography-mass spectrometry (GC-MS) analyses, with the most representative being R -carvone (91.03%), R -limonene (4.10%), and dihydrocarvone (1.07%). For Aloysia polystachya essential oil, antioxidant assays (2,2-diphenyl-1-picrylhydrazyl (DPPH), H 2 O 2 , ferric reducing antioxidant power (FRAP), and total reactive antioxidant potential (TRAP)) showed good antioxidant activity compared to commercial antioxidant controls; and anti-proliferative assays against three human cancer cell lines (colon, HT-29; prostate, PC-3; and breast, MCF-7) determined an IC 50 of 5.85, 6.74, and 9.53 µg/mL, and selectivity indices of 4.75, 4.12, and 2.92 for HT-29, PC-3, and MCF-7, respectively. We also report on assays with CCD 841 CoN (colon epithelial). Overall, results from this study may represent, in the near future, developments for natural-based cancer treatments.

Introduction: Liver cirrhosis and its complication - hepatocellular carcinoma (HCC) - have been associated with increased exhaled limonene. It is currently unclear whether this increase is more strongly associated with the presence of HCC or with the severity of liver dysfunction., Methods: We compared the exhaled breath of 40 controls, 32 cirrhotic patients, and 12 cirrhotic patients with HCC using the Breath Biopsy platform. Breath samples were analyzed by thermal desorption-gas chromatography-mass spectrometry. Limonene levels were compared between the groups and correlated to bilirubin, albumin, prothrombin time international normalized ratio, and alanine aminotransferase., Results: Breath limonene concentration was significantly elevated in subjects with cirrhosis-induced HCC (M: 82.1 ng/L, interquartile range [IQR]: 16.33-199.32 ng/L) and cirrhosis (M: 32.6 ng/L, IQR: 6.55-123.07 ng/L) compared with controls (M: 6.2 ng/L, IQR: 2.62-9.57 ng/L) (P value = 0.0005 and 0.0001, respectively) with no significant difference between 2 diseased groups (P value = 0.37). Levels of exhaled limonene correlated with serum bilirubin (R = 0.25, P value = 0.0016, r = 0.51), albumin (R = 0.58, P value = 5.3e-8, r = -0.76), and international normalized ratio (R = 0.29, P value = 0.0003, r = 0.51), but not with alanine aminotransferase (R = 0.01, P value = 0.36, r = 0.19)., Discussion: Exhaled limonene levels are primarily affected by the presence of cirrhosis through reduced liver functional capacity, as indicated by limonene correlation with blood metrics of impaired hepatic clearance and protein synthesis capacity, without further alterations observed in subjects with HCC. This suggests that exhaled limonene is a potential non-invasive marker of liver metabolic capacity (see Visual abstract, Supplementary Digital Content 1, http://links.lww.com/CTG/A388).

The aim of the present study was to develop a method based on gas chromatography-tandem mass spectrometry (GC-MS/MS) to determine and quantify the d-limonene in mouse plasma and tissue samples. This new method was validated for the quantification of d-limonene with the linearity ranges 1.0-1000.0 ng/mL (r 2  > 0.9952) for plasma samples and 5.0-5000.0 ng/g (r 2  > 0.9940) for tissue samples. The intra- and inter-day assay of precisions in plasma and tissues were <13.4% and the accuracies were within 91.1-105.8%. In the oral/inhalation administration pharmacokinetics and tissue distribution studies, the main pharmacokinetic parameters were the peak concentration = (97.150 ± 34.450)/(4336.415 ± 1142.418) ng/mL, the area under the curve = (162.828± 27.447)/(2085.721 ± 547.787) h ng/mL and the half-life = (3.196 ± 0.825)/(0.989 ± 0.095) h. The tissue distribution of d-limonene in mice after oral/inhalation administration demonstrated a decreasing tendency in different tissues (liver > kidney > heart > lung > spleen)., (© 2019 John Wiley & Sons, Ltd.)

Enantioseparation of limonene-based bicyclic 1,3-aminoalcohols and 1,3,5- and 1,3,6-aminodiols was performed by normal-phase high-performance liquid chromatographic and supercritical fluid chromatographic (SFC) methods on polysaccharide-based chiral stationary phases. The effects of the composition of the mobile phase, the column temperature and the structures of the analytes and chiral selectors on retention and selectivity were investigated by normal-phase LC and SFC technique. Thermodynamic parameters derived from selectivity-temperature-dependence studies were found to be dependent on the chromatographic method applied, the nature of the chiral selector and the structural details of the analytes. Enantiorecognition in most cases was enthalpically driven but an unusual temperature behavior was also observed: decreased retention times were accompanied by improved separation factors with increasing temperature, i.e. some entropically driven separations were also observed. The elution sequence was determined in all cases. The separation of the stereoisomers was optimized in both chromatographic modalities., (© 2019 John Wiley & Sons, Ltd.)

Asthma is a common chronic disease. Exposure to limonene is commonplace because it may be used in the manufacture of personal care products and household cleaners. We investigated the influence of limonene on asthma in a population-based sample of approximately 3000 Canadians. During the Canada Health Measures Survey, carried out between 2012 and 2013, participants were asked if they wheezed or had a diagnosis of asthma, and underwent spirometry and measurement of the fraction of exhaled nitric oxide (FeNO). These variables were tested for an association with limonene concentrations measured in their household air samples, using linear regression analysis A 100% increase in air limonene concentration was associated with an approximate 17% adjusted relative increase wheezing with an odds ratio of 1.17 (95%CI 1.16, 1.18). The percent change in FeNO for a 100% increase in limonene was twice as large for children, 2.89% (95% CI 1.88, 4.43) compared to adults, 1.44% (95%CI 1.16, 1.79). Among boys, the odds ratio was 1.50 (95%CI 1.48, 1.52) between a 100% increase in limonene and a diagnosis of asthma. This study provides evidence that household exposure to limonene may increase the prevalence of asthma in the general population., (Crown Copyright © 2018. Published by Elsevier Ltd. All rights reserved.)