You may be able to access through {InstitutionName}. Six oxygenated monoterpenes were produced and identified by GC–MS.

Google Scholar, Yilmaz BS, Özbek H (2018) Investigation of the anti-inflammatory, hypoglycemic activity and median lethal dose (LD50) level of limoene in mice and rats. (A) Organic species measured by GC×GC with x axis first dimension retention in n-alkane based index and y axis second dimension retention in time (RT2). And yet, exactly what’s contained in these frequent precursors to black holes remains an open question. ↵3Present address: Department of Civil and Environmental Engineering, Virginia Polytechnic Institute and State University, Blacksburg, VA 24061. You have to login with your ACS ID befor you can login with your Mendeley account. 4) could be explained by the dehydrogenation of cis-dihydrocarvone to carvone which is reduced in a stereoselective manner in cis- and trans-carveol.

Allured Publishing Co., Carol Stream, Shibamoto T (1987) Capillary gas chromatography in essential oil analysis. This article is a PNAS Direct Submission. Cutan Ocul Toxicol 38(3):290–293, Günther J, Schneider I, Krämer A (2019) Carvone prevents and alleviates hepatic steatosis in rat model with nonalcoholic fatty liver disease. Historical data from summertime Centreville, AL show that significant decreases in NOx levels have occurred in the past 15 y, with associated decreases of OA, consistent with the trend in the relationship between MTSOA and oxidized NOx reported here (20). The sample volume injected was 1 µL (1% diluted in hexane).

Abou El-Hamd H. Mohamed, Naglaa S. Mohamed, Ahmed R. Hamed, Mohamed-Elamir F. Hegazy. Although individual MTSOA species present strong and different diurnal cycles reflecting their unique formation chemistry (examples shown in Fig. Get article recommendations from ACS based on references in your Mendeley library.

In addition to carvone, trans-carveol, cis-carveol and p-mentha-trans-2,8-dienol already formed in the absence of S. cerevisiae, three additional derivatives were biosynthesized, α-terpineol (2.75%), trans-limonene oxide (1.70%) and linalool (1.17%) (Fig. Google Scholar, Shah BB, Mehta AA (2018) In vitro evaluation of antioxidant activity of d-limonene. S2), total MTSOA mass had a relatively “flat” diurnal pattern during the SOAS field campaign, with the average at ∼3 µg⋅m−3 for the month of June (Fig.


Following the same protocol in the presence of these two yeasts, eight and seven secondary metabolites were formed, respectively. Mar Drugs 16(2):62–76, PubMed Central  In this work we identify monoterpenes as the major OA source in the summertime southeastern US from a molecular-level and measurement-based perspective. Unusual Reagent Control of Diastereoselectivity in the 1,2-Addition of Hard Carbon Nucleophiles to C6-Heteroatom Substituted Cyclohexenones.

Atmospheric aerosol is a highly variable and complex mixture largely composed of organic species derived from anthropogenic and biogenic emissions (1⇓–3). Michel Kenne Tchimene, Christopher O. Okunji, Maurice Mmaduakolam Iwu, Victor Kuete. Good agreement (except for 06/19–06/22, shown in gray symbols) suggests the sum of speciated anthropogenic POA and SOA accounts for most Cfossil mass and the remaining OA are dominated by modern carbon. The similarity in the environmental conditions (20, 21), gas and particle tracers (Table S2), monoterpenes/isoprene ratios (Fig. We estimated speciated fossil carbon (Cfossil) mass based on anthropogenic POA and SOA mass measured by GC×GC and compare with 14C-measured Cfossil in OA (Fig.

Laboratory chamber studies of α-pinene oxidation were also conducted with CIMS measurements.

2B), 30 of which were associated with monoterpene NO3 oxidation (18). oxygenated monoterpenes might contribute to heat stress resis-tance (Copolovici et al., 2005), temperature history effects as observed for isoprene can be expected for monoterpenes as well. Monoterpene Hydroperoxides with Trypanocidal Activity from Chenopodium ambrosioides. Xu et al. analyzed data; and H.Z. Black dashed line represents total primary RO2 production rate, assuming 60% RO2 yield from monoterpene ozonolysis.

We start this study of bioconversion of (R)-limonene by his oxidation with air oxygen. Detailed description of this measurement can be found in previous studies (18, 23, 30).

4D) are also listed in Table S3.

Without of any fungi, 88.09% of (R)-limonene was transformed into six oxygenated monoterpenes (alcohols (56.32%) and ketones (31.77%).

After seven days only 11.91% of (R)-limonene were not oxidized, hence the sensitivity of limonene to this kind of contact.

performed research; N.M.K., S.R.S., and S.V.H. Injecting monoterpenes in excess of O3 allowed simultaneous hydroxyl radical (OH) oxidation of monoterpenes to occur because OH is a product from monoterpene ozonolysis. Chem Eur J 24(51):13607–13615, Morikawa H, Yamaguchi JI, Sugimura SI, Minamoto M, Gorou Y, Morinaga H, Motokucho S (2019) Systematic synthetic study of four diastereomerically distinct limonene-1,2-diols and their correspondin cyclic carbonates.

Fisher Aquat Life 26(2):131–139, Bai J, Zheng Y, Wang G, Liu P (2016) Protective effect of d-limomene against oxidative stress-induced cell damage in human lens epithelial cells via the p38 pathway.

It also continues the bioconversion of some derivatives already obtained from the chemical oxidation (Fig. ↵5Present address: Tofwerk AG, CH-3600 Thun, Switzerland. The first approach estimates contributions from specific sources assuming that the measured molecular markers have the same gas/particle partitioning and production yields from precursors in the atmosphere and in laboratory studies and are conserved in the atmosphere. Chemical composition and antimicrobial activity of crude, aqueous, ethanol extracts and essential oils of Continuous 4-h fine particulate matter (PM1) samples were collected throughout the field campaign and analyzed off-line by thermal desorption and derivatization with 2D gas chromatography (GC×GC) coupled to a high-resolution time-of-flight mass spectrometer (HTOF-MS) with dual ionization.

Author contributions: H.Z., L.D.Y., and A.H.G.

Highly Oxygenated Monoterpenes from Chenopodium ambrosioides The second-largest source contributor to total OA mass is isoprene oxidation. Here, we provide comprehensive molecular characterization of atmospheric organic aerosol samples from the southeastern United States by combining state-of-the-art high-resolution mass spectrometry techniques.

Qiu-Hong Wu, Chun-Mei Liu, Yan-Jun Chen, Kun Gao. 2D, the total characterized OA (r2 = 0.77, n = 113) and MTSOA (r2 = 0.80, n = 113) both correlate strongly with total PM1 OA mass measured by AMS. A number of non-nitrogen-containing C6–C10 species were observed in both the field measurements and chamber studies, supporting their relation to monoterpene oxidation.

The organic layer was dried over Na2SO4. E-mail:  [email protected].

A mixture of 750 μL of (R)-limonene and 75 mL of the culture medium PDB (Potato Dextrose Broth) was stirred at room temperature for 7 days. S3), the 4-h data from 1200–1600 hours and 1600–2000 hours are analyzed as daytime samples and those from 2000–0000 hours and 0000–0400 hours as nighttime samples.

Synergistic Antibacterial Activity of the Essential Oil of Aguaribay (Schinus molle L.). In principle, MTSOA formation is directly determined by (i) rates of initial RO2 production (or other intermediate products) from monoterpene oxidation and (ii) effectiveness of converting RO2 into MTSOA through multiple pathways. The disappearance of cis-dihydrocarvone, the decrease in the proportion of carvone and the increase in proportion of trans-carveol and cis-carveol by comparison to the negative control (Fig. For this work, CIMS measurements using iodide as reagent ions determine that the oxidized chemical formulae with C6–C10 range and suitable H and O numbers (one degree of double bond equivalence is allowed) are MTSOA (96 species).

2) showed that limonene was bioconverted into alcohols (53.16%) and ketones (32.45%) and an epoxide (12.37%) in the presence of T. harzianum.

BFSZU 19:317–331, Smitha MS, Singh S, Singh R (2017) Microbial biotransformation: a process for chemical alterations.

(C) Comparison of Cfossil mass (1σ) speciated in this work with that measured by 14C (r2 = 0.54).

The ratio of fragmentation MTSOA (C4–C9) to functionalization MTSOA (C10) (frag./func.

Chenopodium ambrosioides Chemical formulae with 5 or fewer and 11 or more carbons measured by CIMS that appeared in both field and α-pinene chamber experiments were not considered as MTSOA as they are not distinguishable from possible isoprene or other oxidation products in ambient samples.

2F). Google Scholar, Lasarte-Cia A, LozanoT Pérez-González M, Gorraiz M, Iribarren K, Hervás-Stubbs S, Sarobe P, Rabal O, Cuadrado-Tejedor M, García-Osta A, Casares N, Lasarte JJ (2018) Immunomodulatory properties of carvone inhalation and its effects on contextual fear memory in mice.

Initial conditions and other details of laboratory experiments are provided in Detailed Experimental Procedure. The spectroscopic analysis of the compounds is achieved by comparison with their counterparts with the help of the NBS75K.L spectral bank and WILLEY275.L. The purpose of these experiments was to generate a relatively large “library” of MTSOA species but which does not include all likely MTSOA species for the ambient samples.

During the summertime Southern Oxidant and Aerosol Study (SOAS) campaign in the southeastern US, the AMS–PMF-resolved isoprene secondary OA (SOA) combined with biomass burning OA together account for about 30% of total fine OA mass (16, 17). Leaves in Rats. The authors declare no conflict of interest.

OA molecular-level measurements. In addition, α-pinene ozonolysis chamber experiments were conducted at University of Washington with on-line measurements by CIMS. This article contains supporting information online at

Looking at the structure of the compounds formed by the bioconversion of limonene by T. harzianum we fancy that this yeast catalyzes the formation of some products such as trans-limonene oxide, piperitenone and perillic alcohol.

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