Compound Α-PINENE Data Collection Sheet (1/2)

Total Page:16

File Type:pdf, Size:1020Kb

Compound Α-PINENE Data Collection Sheet (1/2) Compound α-PINENE Data collection sheet (1/2) Classification GHS: H332: Harmful if inhaled (cat. 4), 1 ppm (in air, 23 °C) = 5.61 mg/m3 H319: Causes serious eye irritation (cat. 2) N°CAS 80-56-8 1 ppm (in air, 20 °C) = 5.66 mg/m3 MW=136.23 CLP: not included Organization Name ACGIH BAuA German IAQ AgBB ANSES AFS RWI (target value) RWII (adverse effects Risk Value Name 8-h TWA Occup. target value possible) for bicyclic NIK (=LCI) CLI (=LCI) OEL monoterpenes, model substance = α-pinene 112.12 56.06 (calculated for RWI=0.2 Risk Value (mg/m3) (calculated for 1.5 0.45 150 23°C) RWII=2.0 23°C) RWI=0.036 0.267 0.0803 Risk Value (ppm) 20 10 RWII=0.357 (calculated for (calculated for 25 (calculated for 23°C) 23°C) 23°C) Reference period Subacute Subacute Year 2008 2005 2003 1990 Key Study No information Järvisalo J, Vainio H: Acta Johard U, Larsson K, Löf A, Value derived Value taken No information available Pharmacologica et Eklund A: Controlled from AFS-OEL: × from the EU- available Toxicologica short-time terpene 0.01 INDEX Project 1980;46(1):32–36 exposure induces an increase of the macrophages and the mastcells in bronchoalveolar lavage fluids. Am J Ind Med 1993;23:793–799 Study type Inhalation study 8 volunt. inhalating 450 mg/m3 mixture of α- pinene, beta-pinene, delta- 3-carene (10:1:5). 4×3hrs, in 2 weeks. Elevated cell- concentrations in BAL after exposition, interpreted as acute alveolar cellular reaction / inflammation marker. Species Rat Man Duration of 6h/d, 5d/w for 8 weeks 4 × 3 hrs in 2 weeks exposure in key study Critical effect Study with turpentine 20 hrs after exposure (95% α-pinene). significant higher Enhanced activities of concentrations of alveolar drug biotransformation cell concentrations enzymes of liver (median pre-exposure 76 × microsomes: NADPH l06 cells/L -> 126 × l06 cytochrome c reductase cells/L), predominantly and 7-ethoxycoumarin due to macrophages (72 × deethylase, and l06 cells/L -> 121 × l06 microsomal content of cells/L). Also mast cells cytochrome P-450 increased: 1/10 -> 5/10 (increased 35–60% only visual fields. during first weeks). Increase in liver microsomal epoxide hydratase and UDPglucuronosyltransfer ase tended to adapt less. Result describes not an adverse effect per se, but influence of biotransformation of drugs is possible. Critical dose value 1,710 mg/m3 (300 ppm) LOAEL: 450 mg/m3 Adjusted critical ENAELinhal: 128 mg/m3 dose (23 ppm) Derived Exposition Target Value 56 mg/m3 (10 ppm) Single assessment No information given UFS 12 x UFH 10 x UFChildren factors (see table 2 = 1.875 mg/m3 R.8.6) -> RWII = 2 mg/m3 Other effects Odour thresholds, different values published: α-pinene 3.9 mg/m3 (+)α-pinene 23 mg/m3 (−)α-pinene 107 mg/m3 Confidence UFL used LOAEL; UFH intraspecies variability; UFA interspecies variability; UFS used subchronic study; UFD data deficiencies Compound α-PINENE Data collection sheet (2/2) Data from ECHA for NTP study with not Mersch-Sundermann Organization Name EU-INDEX Project Gminski et al. not specified α- specified α-pinene, CAS review pinene, CAS 80-56-8 80-56-8 Long term exposure systemic effects Risk Value Name IAQ proposed LCI Not appointed NOAEL general population inhalation DNEL Risk Value (mg/m3) 0.45 4 Not appointed 1.06 0.0803 0.714 0.187 Risk Value (ppm) Not appointed 50 (calculated for 23°C) (calculated for 23°C) (calculated for 23°C) Reference period Subchronic Subchronic 2012 (status ECHA- Year 2005 2007 2011 2006 Homepage) Key Study Falk Filipsson A: Short Animal study: Human inhalation study: NTP-Study 2005 NTP-Study term inha-lation Kasanen JP, Pasanen Gminski R. Marutzky R. TDMS Number 2030203 exposure to turpentine: AL, Pasanen P, Keve-kordes S. Fuhrmann F. =TOX-81 Study toxicokinetics and Liesivuori J, Kosma VM, Burger W. Hauschke D. acute effects in men. Alarie Y: Stereospecifity Ebner W. Mersch- Occup Environ Med of the sensory irritation Sundermann V: 1996;53:100–105 receptor for Chemosensory irritations nonreactive chemicals and pulmonary effects of Falk A, Hagberg M, Löf illustrated by pinene acute exposure to emissions A, Wigaeus-Hjelm E, enantiomers. Arch from oriented strand board. Wang Z: Uptake, Toxicol 1998;72:514– Human & Experimental distribution and 523 Toxi-cology elimination of a-pinene 2011;30(9):1204–21 in man after exposure Human exposition by inhalation. Scand J study: Work Environ Health Falk Filipsson A: Short 1990;16:372–8 term inhalation exposure to turpentine: toxicokinetics and acute effects in men. Occup Environ Med 1996;53:100–105 Lowest OEL-value: Swedish OEL 150 mg/m3 Odour threshold: lowest 4 mg/m3 Study type 8 volunteers inhalated Animal study: 24 volunteers were exposed Animal Study: Animal Study: 450 mg/m3 turpentene: Short (30') exposure for 2hrs to oriented Subchronic Subchronic inhalation alpha-pinene, beta- (inhalation) and strandboard (OSB) inhalation study study pinene, delta-3-carene, measure-ment of emissions in an emission exposition at 25 ppm exposition at 25 ppm / 5:1:3 (1st study) or respiratory parameters. chamber at 3 points of time / 50 ppm / 100 ppm / 50 ppm / 100 ppm / 200 alpha-pinene alone Concentrations of (panels fresh, 2 and 8 weeks 200 ppm / 400 ppm. ppm / 400 ppm. (2nd study). Irritation alpha-pinene 100– old). Chemosensory 10 Animals per sex 10 Animals per sex and by alpha-pinene was 3,691 ppm. irritation, exhaled nitric and concentration concentration used. reported at 450 mg/m³ oxide (NO) concentration, used. but not at 225 mg/m³. eye blink frequency, lung Dis-comfort against function and subjective turpentene was perception of irritation reported, also airway (eyes, nose, throat) and resistance was olfactory perception were increased. Both studies: investigated. 1 Exposition for 2 hrs Species Man Mouse / man B6C3F1 Mice and B6C3F1 Mice and F344 F344 Rats Rats Duration of 1 Exposition for 2 hrs Animal study: 30 min 3 × 2 hrs (14 weeks according 96 days for mice (14 exposure in key to ECHA) weeks) study 90-day inhalation =test-type "90 days" study Critical effect Irritation / discomfort Animal study: OF1 and No effects found except of From ECHA- Significant effects (self-reported) and NIH/S male mice, 4 of odour perception. Summary: Male and (p<=0.05) Male rats, airway resistance each used per female mice at 100 moderate effects: experiment, expo-sure ppm: minimal to granular casts in kidney: time 30', measurement moderate hyperplasia accumulation of hyaline of lung functions by observed in the droplets starting at 25 body plethys-mograph. transitional ppm. Note: 9/10 animals Endpoint RD50 = 50% epithelium of the showed nephropaty in depression of urinary bladder. The control group (other respiratory rate NOAEL in male and effects). Female rats, by sensory irritation of female rats is 50 ppm minimal effects: chronic upper respiratory tract based on minimal to lung inflammation. Note: Human exposition moderate hyperplasia 4/10 in control group, study: 8 volunteers observed in the 5/9 at 400 ppm. Mice in exposed to 450 mg/m3 transitional both sexes, minimal to turpentene: α-pinene, epithelium of the moderate effects: beta-pinene, delta-3- urinary bladder in hyperplasia of carene, 5:1:3 (1st animals treated at transitional epithelium of study) or α-pinene 100 to 400 ppm urinary bladder starting alone (2nd study). at 100 ppm (13/20 Irritation by α-pinene mice). The effect is was reported at 450 concentration-dependent mg/m³ but not at 225 (200 ppm: 20/20 mice) mg/m³. Discomfort against turpentene was reported, also airway resistance was increased. Both studies: 1 Exposition for 2 hrs Critical dose value LOAEL: 450 mg/m3 Animal study: RD50 Concentration of α-pinene in NOAEL: 225 mg/m3 1080 ppm (9 g /m3) the chamber: 1.1–2.2 Human exposition mg/m3. α-pinene was a study: LOAEL: 450 leading component of the mg/m3 OSB-emission, TVOC was OEL: 150 mg/m3 4.9–8.9 mg/m3. The results Odour threshold: 4 represent a NOAEL for OSB- mg/m3 emissions, including an α- pinene TVOC-proportion of 16–25%. Adjusted critical IAQ exposure limit: Animal study: 4.5 dose 0.45 mg × m−3 mg/m3 Human exposition study: 4.5 mg/m3 OEL:3.75 mg/m3 Odour threshold:no adjustment, 4 mg/m3 Single assessment UFL 10 x UFS10 x UFH Animal study: RD50 x factors (see table 10 = 1000 0.03 = reasonable OEL, R.8.6) then UFS24/6 x UFH 10 = 40 Human exposition study: UFS10 x UFH 10 = 100 OEL: UFS24/6 x UFH 10 = 40 Other effects Odour thresholds: (+)α- Odour thresholds, pinene 12 mg/m3 (2.1 different values ppm), (−)α-pinene 18 published: α-pinene mg/m3 (3.3 ppm) range 4–25 mg/m3 Reaction of (+)α-pinene with ozone amplifies irritative effect: Wolkoff P, Clausen PA, Wilkins CK, Nielsen GD: Formation of strong airway irritants in terpene/ozone mixtures. Indoor Air 2000;10:82–91 (ASTM mouse bioassay: 56 ppm at 21°C= 316 mg/m³ -> 30% lower respiration rate for mixture) Confidence UFL Used LOAEL; UFH Intraspecies variability; UFA interspecies variability; UFS Used subchronic study; UFD data deficiencies Compound α-PINENE Factsheet Parameter Note Comments Value / descriptor EU-LCI Value and Status EU-LCI value 1 Mass/volume [µg/m³] 2500 EU-LCI status 2 Draft / Final Final Year when the EU-LCI value has been EU-LCI year of issue 3 2012 issued General Information CLP-INDEX-Nr. 4 INDEX EC-Nr. 5 EINECS – ELINCS - NLP 201-291-9 CAS-Nr.
Recommended publications
  • Topical Toxicity of Essential Oils to the German Cockroach (Dictyoptera: Blattellidae)
    HOUSEHOLD AND STRUCTURAL INSECTS Topical Toxicity of Essential Oils to the German Cockroach (Dictyoptera: Blattellidae) 1,2 1 3 ALICIA K. PHILLIPS, ARTHUR G. APPEL, AND STEVEN R. SIMS J. Econ. Entomol. 103(2): 448Ð459 (2010); DOI: 10.1603/EC09192 ABSTRACT The toxicity of 12 essential oil components [carvacrol, 1,8-cineole, trans-cinnamalde- Downloaded from https://academic.oup.com/jee/article/103/2/448/2199422 by guest on 28 September 2021 hyde, citronellic acid, eugenol, geraniol, S-(Ϫ)-limonene, (Ϫ)-linalool, (Ϫ)-menthone, (ϩ)-␣- pinene, (Ϫ)-␤-pinene, and thymol] to adult male; adult female; gravid female; and large, medium, and small nymphs of the German cockroach, Blattella germanica (L.) (Dictyoptera: Blattellidae), was determined. Thymol was the most toxic essential oil component to adult males, gravid females, and medium nymphs, with LD50 values of 0.07, 0.12, and 0.06 mg per cockroach, respectively. trans- Cinnamaldehyde was the most toxic essential oil component to adult females, large nymphs, and small ϩ ␣ nymphs, with LD50 values of 0.19, 0.12, and 0.04 mg per cockroach, respectively. ( )- -Pinene was the least toxic essential oil component to all stages of the German cockroach. The most frequently occurring susceptibility ranking for the stages was small nymphs Ͼ medium nymphs Ͼ adult males Ͼ large nymphs Ͼ gravid females Ͼ adult females. Adult females were the least susceptible to the essential oils, so they will be the determining factor when considering a rate for Þeld application. Toxicity was positively correlated with essential oil component density and boiling point; however, there was no signiÞcant correlation between toxicity and lipophilicity.
    [Show full text]
  • Emission and Abundance of Biogenic Volatile Organic Compounds in Wind-Throw Areas of Upland Spruce Forests in Bavaria Benjamin S
    Technische Universität München Wissenschaftszentrum Weihenstephan für Ernährung, Landnutzung und Umwelt Lehrstuhl für Atmosphärische Umweltforschung Emission and abundance of biogenic volatile organic compounds in wind-throw areas of upland spruce forests in Bavaria Benjamin S. J. Wolpert Vollständiger Abdruck der von der Fakultät Wissenschaftszentrum Weihenstephan für Ernährung, Landnutzung und Umwelt der Technischen Universität München zur Erlangung des akademischen Grades eines Doktors der Naturwissenschaften (Dr. rer. nat.) genehmigten Dissertation. Vorsitzender: Univ.-Prof. Dr. Reinhard Schopf Prüfer der Dissertation: 1. Univ.-Prof. Hans Peter Schmid, Ph.D. 2. Univ.-Prof. Dr. Annette Menzel 3. Prof. Jose Fuentes, Ph.D., Pennsylvania State University, USA (nur schriftliche Beurteilung) Die Dissertation wurde am 02.05.2012 bei der Technischen Universität München eingereicht und durch die Fakultät Wissenschaftszentrum Weihenstephan für Ernährung, Landnutzung und Umwelt am 07.09.2012 angenommen. Table of contents 1. Introduction ............................................................................. 1 1.1. Motivation ................................................................................................... 1 1.2. Biogenic volatile organic compounds .......................................................... 2 1.3. Monoterpenoids .......................................................................................... 3 1.4. Functional relationship of monoterpenes and plants ................................... 5 1.4.1.
    [Show full text]
  • DIFFERENCES in Terpenoid Levels Between Plant Species Are Known To
    GENETICS OF TEP.PENES I. GENE CONTROL OF MONOTERPENE LEVELS IN PINUS MONTICOLA DOUGL. JAMES W. HANOVER Geneticist, Forestry Sciences Laboratory, lntermountain Forest and Range Experiment Station, U.S. Department of Agriculture, Moscow, Idaho * Receivedi o.v.6 1.INTRODUCTION DIFFERENCESin terpenoid levels between plant species are known to exist but little is known about their genetic bases. The terpenes have been used extensively in biochemical systematic studies in Pinus (Mirov, 1958, 1961; Williams and Bannister, 1962; Forde, 1964), Eucalyptus (Baker and Smith, 1920; Penfold and Morrison, 1927), Cup ressacee (Erdtman, 1958),andmany other plant families and genera (Alston and Turner, 1963).Thesestudies were usually based upon the assumption that variation within a species is relatively small. Although this may be valid in some cases, Bannister et al. (1962)andothers have shown that the level of terpenes can vary with geographic origin within a species. Recent data on tree-to-tree variability in the monoterpenes of Pinus ponderosa Laws. show that such variation can be relatively large (Smith, 1964). Results of similar work in our laboratory with western white pine (Pinus monticola Dougi.) also revealed substantial qualitative and quantitative variation in the cortex monoterpenes between trees. In order to provide a basis for the use of terpenes for comparative biochemical studies, an understanding of both their variability and mode of inheritance is essential. The objective of the present study is to demonstrate the degree to which levels of six monoterpene compounds are gene-controlled in western white pine. Interrelations among the terpenes and between terpenes and growth are also considered, 2.MATERIALS AND METHODS Thematerials for this study are of three types: (i) parents—as clonal lines of grafts, () F1 progeny from crosses between the ortets (parents) represented by the clones, and () S1 progeny of the parent trees.
    [Show full text]
  • Determination of Terpenoid Content in Pine by Organic Solvent Extraction and Fast-Gc Analysis
    ORIGINAL RESEARCH published: 25 January 2016 doi: 10.3389/fenrg.2016.00002 Determination of Terpenoid Content in Pine by Organic Solvent Extraction and Fast-GC Analysis Anne E. Harman-Ware1* , Robert Sykes1 , Gary F. Peter2 and Mark Davis1 1 National Bioenergy Center, National Renewable Energy Laboratory, Golden, CO, USA, 2 School of Forest Resources and Conservation, University of Florida, Gainesville, FL, USA Terpenoids, naturally occurring compounds derived from isoprene units present in pine oleoresin, are a valuable source of chemicals used in solvents, fragrances, flavors, and have shown potential use as a biofuel. This paper describes a method to extract and analyze the terpenoids present in loblolly pine saplings and pine lighter wood. Various extraction solvents were tested over different times and temperatures. Samples were analyzed by pyrolysis-molecular beam mass spectrometry before and after extractions to monitor the extraction efficiency. The pyrolysis studies indicated that the optimal extraction method used a 1:1 hexane/acetone solvent system at 22°C for 1 h. Extracts from the hexane/acetone experiments were analyzed using a low thermal mass modular accelerated column heater for fast-GC/FID analysis. The most abundant terpenoids from Edited by: the pine samples were quantified, using standard curves, and included the monoter- Subba Rao Chaganti, University of Windsor, Canada penes, α- and β-pinene, camphene, and δ-carene. Sesquiterpenes analyzed included Reviewed by: caryophyllene, humulene, and α-bisabolene. Diterpenoid resin acids were quantified in Yu-Shen Cheng, derivatized extractions, including pimaric, isopimaric, levopimaric, palustric, dehydroabi- National Yunlin University of Science and Technology, Taiwan etic, abietic, and neoabietic acids.
    [Show full text]
  • Catàleg E-Liquids ENG.Indd
    our aromas Composition What are E-liquids? The cannabis aromas (cannabis terpenes profiles) of Cali Terpenes are from botanical origin, 100% pure, E-liquids, e-juice or food grade, toxic-free and GMO-free. vaping liquids are liquid mixtures intended to be vaporized in electronic cigarettes and the main objective of e-liquids is to offer an alternative to smokers, as it’s proven 100% faithful aroma to be 95% healthier www.caliterpenes.com than smoking. of each strain e-liquids catalog our e-liquids Composition Our e-liquids are composed exclusively of propylene glycol (PG), vegetable glycerin (VG) and food grade cannabis aromas of botanical origin. What is CBD? For its minimum vegetable glycerin content is the healthiest e-liquid on the market. CBD (or Cannabidiol) is one of the non-psychoactive components of cannabis and hemp. CBD acts on our High quality formulation, in collaboration endocannabinoid system with the doctor Mariano Garcia de Palau. and stimulates the natural response of the body against stress or pain. THC NIC VIT.E FREE FREE FREE CBD contained in our E-liquids is produced under Follow us: Do not Do not Do not GMP standard, with approximately 99,8% purity. contain contain contain @caliterpenes @cali_terpenes THC Nicotine Vit E @caliterpenes @caliterpenes E-LIQUID WITH TERPENES Available formats: • 10ml - 0 mg CBD Flavor Flavor Flavor Flavor Flavor • 50ml - 0 mg CBD Sweet / Blueberries / Pine Citric / Fresh / Sweet Sweet / Citric / Peppery Earthy / Deep / Pungent Diesel / Citric / Herbal Main terpenes Main terpenes Main terpenes Main terpenes Main terpenes Enjoy the taste of Terpinolene, Caryophyllene, Beta-Ocimene, Caryophyllene, Myrcene, L-alpha-Pinene, Caryophyllene, d-Limonene, Myrcene, Myrcene, Caryophyllene, d-Limonene, Caryophyllene, Myrcene, Limonene, Linalool, Myrcene, Beta-Pinene, D-Limonene, Alpha- D-Limonene, L-beta-Pinene, L-beta-Pinene, Linalool, L-alpha-Pinene, D-Alpha-Pinene, Alpha-Pinene, Beta-Pinene.
    [Show full text]
  • Living Polymerization of Renewable Vinyl Monomers Into Bio-Based Polymers
    Polymer Journal (2015) 47, 527–536 & 2015 The Society of Polymer Science, Japan (SPSJ) All rights reserved 0032-3896/15 www.nature.com/pj FOCUS REVIEW Controlled/living polymerization of renewable vinyl monomers into bio-based polymers Kotaro Satoh1,2 In this focused review, I present an overview of our recent research on bio-based polymers produced by the controlled/living polymerization of naturally occurring or derived renewable monomers, such as terpenes, phenylpropanoids and itaconic derivatives. The judicious choice of initiating system, which was borrowed from conventional petrochemical monomers, not only allowed the polymerization to proceed efficiently but also produced well-defined controlled/living polymers from these renewable monomers. We were able to find several controlled/living systems for renewable monomers that resulted in novel bio-based polymers, including a cycloolefin polymer, an AAB alternating copolymer with an end-to-end sequence, a phenolic and high-Tg alternating styrenic copolymer, and an acrylic thermoplastic elastomer. Polymer Journal (2015) 47, 527–536; doi:10.1038/pj.2015.31; published online 13 May 2015 INTRODUCTION aliphatic olefins and styrenes,22,23 whereas the latter applies to most Bio-based polymers are attractive materials from the standpoints of unsaturated compounds bearing C = Cbonds.24–38 Controlled/living being environmentally benign and sustainable. They are usually radical polymerization can precisely control the molecular weights and derived from renewable bio-based feedstocks, such as starches, plant the terminal groups of numerous monomers and has opened a new oils and microbiota, as an alternative to traditional polymers from field of precision polymer synthesis that has been applied to the fossil resources.1 Most of the bio-based polymers produced in the production of a wide variety of functional materials based on 1990s were polyesters prepared via condensation or ring-opening controlled polymer structures.
    [Show full text]
  • Importance of Secondary Organic Aerosol Formation of Α-Pinene, Limonene, and M-Cresol Comparing Day- and Nighttime Radical Chemistry
    Atmos. Chem. Phys., 21, 8479–8498, 2021 https://doi.org/10.5194/acp-21-8479-2021 © Author(s) 2021. This work is distributed under the Creative Commons Attribution 4.0 License. Importance of secondary organic aerosol formation of α-pinene, limonene, and m-cresol comparing day- and nighttime radical chemistry Anke Mutzel1,a, Yanli Zhang1,2, Olaf Böge1, Maria Rodigast1,b, Agata Kolodziejczyk3,1, Xinming Wang2, and Hartmut Herrmann1 1Leibniz Institute for Tropospheric Research (TROPOS), Atmospheric Chemistry Department (ACD), Permoserstr. 15, 04318 Leipzig, Germany 2State Key Laboratory of Organic Geochemistry and Guangdong Key Laboratory of Environmental Protection and Resources Utilization, Guangzhou Institute of Geochemistry, Chinese Academy of Sciences, Guangzhou 510640, China 3Institute of Physical Chemistry of the Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland anow at: Eurofins Institute Dr. Appelt Leipzig, Täubchenweg 28, 04318 Leipzig bnow at: Indulor Chemie GmbH & Co. KG Produktionsgesellschaft Bitterfeld, 06749 Bitterfeld-Wolfen, Germany Correspondence: Anke Mutzel ([email protected]) and Hartmut Herrmann ([email protected]) Received: 19 November 2019 – Discussion started: 29 January 2020 Revised: 11 March 2021 – Accepted: 6 April 2021 – Published: 4 June 2021 Abstract. The oxidation of biogenic and anthropogenic com- which originated from α-pinene varied between 2 and 80 % pounds leads to the formation of secondary organic aerosol as a function of RH. mass (SOA). The present study aims to investigate α-pinene, Furthermore, SOA from α-pinene revealed pinonic acid as limonene, and m-cresol with regards to their SOA formation the most important particle-phase constituent under day- and potential dependent on relative humidity (RH) under night- nighttime conditions with a fraction of 1–4 %.
    [Show full text]
  • Limonene and (+)-Α-Pinene on Bacterial Cells
    biomolecules Article The Mode of Action of Cyclic Monoterpenes (−)-Limonene and (+)-α-Pinene on Bacterial Cells Olga E. Melkina 1, Vladimir A. Plyuta 2 , Inessa A. Khmel 2 and Gennadii B. Zavilgelsky 1,* 1 State Research Institute of Genetics and Selection of Industrial Microorganisms of the National Research Centre “Kurchatov Institute”, Kurchatov Genomic Center, 117545 Moscow, Russia; [email protected] 2 Institute of Molecular Genetics of the National Research Center “Kurchatov Institute”, 123182 Moscow, Russia; [email protected] (V.A.P.); [email protected] (I.A.K.) * Correspondence: [email protected] Abstract: A broad spectrum of volatile organic compounds’ (VOCs’) biological activities has attracted significant scientific interest, but their mechanisms of action remain little understood. The mechanism of action of two VOCs—the cyclic monoterpenes (−)-limonene and (+)-α-pinene—on bacteria was studied in this work. We used genetically engineered Escherichia coli bioluminescent strains harboring stress-responsive promoters (responsive to oxidative stress, DNA damage, SOS response, protein damage, heatshock, membrane damage) fused to the luxCDABE genes of Photorhabdus luminescens. We showed that (−)-limonene induces the PkatG and PsoxS promoters due to the formation of reactive oxygen species and, as a result, causes damage to DNA (SOSresponse), proteins (heat shock), and membrane (increases its permeability). The experimental data indicate that the action of (−)- limonene at high concentrations and prolonged incubation time makes degrading processes in cells irreversible. The effect of (+)-α-pinene is much weaker: it induces only heat shock in the bacteria. Moreover, we showed for the first time that (−)-limonene completely inhibits the DnaKJE–ClpB bichaperone-dependent refolding of heat-inactivated bacterial luciferase in both E.
    [Show full text]
  • Chemical Composition and Antimicrobial Activity of Essential Oils Obtained from Leaves and Flowers of Salvia Hydrangea DC. Ex Be
    www.nature.com/scientificreports OPEN Chemical composition and antimicrobial activity of essential oils obtained from leaves and fowers of Salvia hydrangea DC. ex Benth. Mansureh Ghavam 1*, Maria Letizia Manca 2, Maria Manconi2 & Gianluigi Bacchetta2,3 The majority of essential oils obtained from vascular plants have been demonstrated to be efective in treating fungal and bacterial infections. Among others, Salvia hydrangea is an endemic half-shrub belonging to the Lamiaceae family that has been widely used from ancient times in Iranian traditional medicine. The aim of this study was to compare the composition and antimicrobial properties of essential oils obtained from leaves or fowers of this plant, collected from the Daran region of Iran during June 2018. The oils were obtained using Clevenger apparatus, their composition was evaluated by means of gas chromatography/mass spectrometry (GC/MS) and the antimicrobial properties were assayed by measuring inhibition halos, minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC). The yield of leaf oil was ~ 0.25% and that of fower oil was ~ 0.28%. Oil composition was afected by the part of the plants used: the most abundant bioactives contained in leaf essential oil were (+)-spathulenol (16.07%), 1,8-cineole (13.96%), trans-caryophyllene (9.58%), β-pinene (8.91%) and β-eudesmol (5.33%) and those in fower essential oil were caryophyllene oxide (35.47%), 1,8-cineole (9.54%), trans-caryophyllene (6.36%), β-eudesmol (4.11%), caryophyllenol-II (3.46%) and camphor (3.33%). Both the oils showed a signifcant inhibitory and lethal efect on the Gram-negative bacteria Pseudomonas aeruginosa (MIC ~ 16 µg/mL), Shigella dysenteriae and Klebsiella pneumoniae (MIC ~ 62 µg/mL).
    [Show full text]
  • Pinene and Limonene SOA Yields
    Atmos. Chem. Phys. Discuss., 8, 15595–15664, 2008 Atmospheric www.atmos-chem-phys-discuss.net/8/15595/2008/ Chemistry ACPD © Author(s) 2008. This work is distributed under and Physics 8, 15595–15664, 2008 the Creative Commons Attribution 3.0 License. Discussions α This discussion paper is/has been under review for the journal Atmospheric Chemistry -pinene and and Physics (ACP). Please refer to the corresponding final paper in ACP if available. limonene SOA yields H. Saathoff et al. Temperature dependence of yields of Title Page secondary organic aerosols from the Abstract Introduction ozonolysis of α-pinene and limonene Conclusions References Tables Figures H. Saathoff1, K.-H. Naumann1, O. Mohler¨ 1, A.˚ M. Jonsson2, M. Hallquist2, 3 3 3 1 A. Kiendler-Scharr , Th. F. Mentel , R. Tillmann , and U. Schurath J I 1Institute for Meteorology and Climate Research, Forschungszentrum Karlsruhe, J I Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany 2 Dept. of Chemistry, Atmospheric Science, Univ. of Gothenburg 412 96 Goteborg,¨ Sweden Back Close 3Institute of Chemistry and Dynamics of the Geosphere 2, Forschungszentrum Julich,¨ 52425 Julich,¨ Germany Full Screen / Esc Received: 15 July 2008 – Accepted: 16 July 2008 – Published: 15 August 2008 Printer-friendly Version Correspondence to: H. Saathoff (harald.saathoff@imk.fzk.de) Interactive Discussion Published by Copernicus Publications on behalf of the European Geosciences Union. 15595 Abstract ACPD Secondary organic aerosol (SOA) formation has been investigated as a function of temperature and humidity for the ozone-initiated reaction of the two monoterpenes 8, 15595–15664, 2008 α-pinene (243–313 K) and limonene (253–313 K) using the 84.5 m3 aerosol chamber 5 AIDA.
    [Show full text]
  • Gallstones' J
    Gut, 1979, 20, 312-317 Gut: first published as 10.1136/gut.20.4.312 on 1 April 1979. Downloaded from Clinical trial Rowachol - a possible treatment for cholesterol gallstones' J. DORAN, M. R. B. KEIGHLEY, AND G. D. BELL From the University Department of Therapeutics, City Hospital, Nottingham, and the University Department of Surgery, General Hospital, Birmingham SUMMARY It has been claimed that Rowachol, a proprietary choleretic, is occasionally successful in the treatment of gallstones. In gallstone patients we have examined its effect on the lipid composi- tion of (1) samples of fasting gall bladder bile obtained at the time of cholecystectomy, and (2) T-tube bile on the tenth post-operative day. In a dose of two capsules, three times a day for only 48 hours, Rowachol significantly lowered the cholesterol solubility of both gall bladder (p < 0001) and T-tube bile (p < 005). Rowachol in a dose of one capsule three times a day for 48 hours did not alter bile composition, while four capsules four times a day for a similar period caused a significant (p < 0-05) deterioration in biliary lipid composition. The possible mechanisms ofaction of Rowachol and their therapeutic implications are discussed. The bile of patients with cholesterol gallstones is purified plant essential oils-for example, 1-menthol frequently saturated with cholesterol (Admirand and from Mentha piperidis, the peppermint plant or Small, 1968). It has been shown that chenodeoxy- 1-cineol from eucalyptus leaves. This particular cholic acid (CDCA) enhances the cholesterol combination of terpenes was chosen by the manu- of human bile and in suitable facturer in it a solubility patients because, the rat, was shown to have http://gut.bmj.com/ promotes dissolution of cholesterol gallstones larger and more sustained choleretic effect than (Bell et al., 1972; Danzinger et al., 1972; Thistle and equimolar quantities of any of its individual con- Hofmann, 1973; Iser et al., 1975; Thistle et al., stituents (Morsdorf, 1966).
    [Show full text]
  • Monoterpenes and Their Derivatives—Recent Development in Biological and Medical Applications
    International Journal of Molecular Sciences Review Monoterpenes and Their Derivatives—Recent Development in Biological and Medical Applications Mariola Zieli ´nska-Błajet* and Joanna Feder-Kubis * Faculty of Chemistry, Wrocław University of Science and Technology, Wybrze˙zeWyspia´nskiego 27, 50-370 Wrocław, Poland * Correspondence: [email protected] (M.Z.-B.); [email protected] (J.F.-K.); Tel.: +48-71-320-2975 (J.F.-K.); Fax: +48-71-328-0475 (J.F.-K.) Received: 29 August 2020; Accepted: 23 September 2020; Published: 25 September 2020 Abstract: Monoterpenes, comprising hydrocarbons, are the largest class of plant secondary metabolites and are commonly found in essential oils. Monoterpenes and their derivatives are key ingredients in the design and production of new biologically active compounds. This review focuses on selected aliphatic, monocyclic, and bicyclic monoterpenes like geraniol, thymol, myrtenal, pinene, camphor, borneol, and their modified structures. The compounds in question play a pivotal role in biological and medical applications. The review also discusses anti-inflammatory, antimicrobial, anticonvulsant, analgesic, antiviral, anticancer, antituberculosis, and antioxidant biological activities exhibited by monoterpenes and their derivatives. Particular attention is paid to the link between biological activity and the effect of structural modification of monoterpenes and monoterpenoids, as well as the introduction of various functionalized moieties into the molecules in question. Keywords: geraniol; thymol; myrtenal; pinene; camphor; borneol; biological activity; antiviral activity; analgesic activity; anti-inflammatory activity 1. Introduction Plants have been used for medical purposes for centuries. As such, they have been studied scientifically and traded commercially. Monoterpenes belong to a large and diverse group of naturally occurring compounds.
    [Show full text]