Antinociceptive Action and Redox Properties of Citronellal, an Essential Oil Present in Lemongrass

Total Page:16

File Type:pdf, Size:1020Kb

Antinociceptive Action and Redox Properties of Citronellal, an Essential Oil Present in Lemongrass View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by Repositório Institucional da Universidade Federal de Sergipe JOURNAL OF MEDICINAL FOOD J Med Food 14 (6) 2011, 630–639 # Mary Ann Liebert, Inc. and Korean Society of Food Science and Nutrition DOI: 10.1089=jmf.2010.0125 Antinociceptive Action and Redox Properties of Citronellal, an Essential Oil Present in Lemongrass Lucindo Quintans-Ju´nior,1 Ricardo Fagundes da Rocha,2 Fernanda Freitas Caregnato,2 Jose´ Claudio Fonseca Moreira,2 Francilene Amaral da Silva,1 Adriano Antunes de Souza Arau´jo,1 Joa˜o Paulo Almeida dos Santos,1 Moˆnica Santos Melo,1 Damia˜o Pergentino de Sousa,1 Leonardo Rigoldi Bonjardim,1 and Daniel Pens Gelain1,2 1Department of Physiology, Federal University of Sergipe, Aracaju, Sergipe, Brazil. 2Center for Studies in Oxidative Stress, Federal University of Rio Grande do Sul, Porto Alegre, Rio Grande do Sul, Brazil. ABSTRACT Citronellal (CT) is a monoterpenoid and the major constituent of the mixture of terpenoids that give the citronella oil its lemon scent. Citronella oil is widely used around the world for various purposes and is mainly obtained from plants of the Cymbopogon genus, which are known as ‘‘lemongrass.’’ Considering these plants have been used worldwide for various medicinal purposes, the interest of researchers to understand the biological activities of monoterpenoids related to the Cymbopogon genus has been increasing. In the present work, we investigated the antinociceptive action and the redox properties of CT. Our results indicate that intraperitoneal injection of CT was effective in reducing nociceptive face-rubbing behavior in both phases of the formalin test, which was also naloxone-sensitive. CT also evoked antinociceptive response in the capsaicin and glutamate tests. The total radical-trapping antioxidant parameter and total antioxidant reactivity assays indicate that CT at doses of 0.1 and 1 mg=mL exerts a significant antioxidant activity, which is probably related to its ability to scavenge superoxide and nitric oxide, but not H2O2 or hydroxyl radicals, as evaluated separately by specific in vitro tests. These results show for the first time the antinociceptive potential of CT and indicate that the antioxidant properties of this compound may rely on its mechanism of biological actions because CT-containing natural products are used to treat various diseases related to oxidative stress and reactive species. KEY WORDS: antinociception citronellal free radicals oxidative stress INTRODUCTION The essential oils are natural products that exhibit vari- ous biological properties, such as analgesic,7 anticonvul- pidemiological studies have been suggested an in- sant,8 and anxiolytic9 effects. Those effects are attributed to verse correlation between the consumption of certain E the monoterpenes, which are the major chemical compo- natural products and the risk of degenerative diseases, can- nents of these essential oils. Citronellal (CT) is a monoter- cer, cardiovascular diseases, and chronic pain.1–4 The pres- pene product from plant secondary metabolism. It is ence of secondary metabolites with antioxidant activity or typically isolated as a non-racemic mixture of its R and S other redox-related properties is generally associated with enantiomers by steam distillation or solvent extraction from such properties, as many of the conditions in which these the oils of Corymbia citriodora Hill and Johnson (former natural products have been observed to exert a preven- Eucalyptus citriodora Hook), Cymbopogon nardus, Cym- tive=therapeutic action are strongly related to oxidative bopogon citratus, and Cymbopogon winterianus (‘‘Java stress and increased reactive species production.5,6 The in- citronella’’).8,10 It is also found in more than 50 other es- crease in reactive species production may result from mul- sential oils. Plants from the Cymbopogon genus are known tiple endogenous (i.e., aging, mitochondrial metabolism) under various names, the most popular being ‘‘lemongrass’’ and exogenous (smoke, ultraviolet radiation, pollution) and ‘‘citronella.’’11 Cymbopogon leaves are used as infusion factors and induce oxidative damage to biomolecules such as preparations for use as spices, medicinal and recreational DNA, proteins, and lipids. teas, soups, and curries.11 Other CT-containing plants, such as members of the genuses Eucalyptus, Melissa, Mentha, Manuscript received 11 May 2010. Revision accepted 3 August 2010. Allium, and Cinnamomum, among others, also present no- table nutritional value and are important food=spice sources Address correspondence to: Daniel Pens Gelain, Ph.D., Departamento de Bioquı´mica, 12 Universidade Federal do Rio Grande do Sul, Rua Ramiro Barcelos, 2600, anexo, CEP in different parts of the world. In Cymbopogon (lemongrass) 90035-003, Porto Alegre, RS, Brazil, E-mail: [email protected] and Melissa officinalis (balm), CT is considered a major 630 PROPERTIES OF CITRONELLAL 631 constituent of the leaves, contributing to a great extent of the thiol), hydrogen peroxide, adrenaline, catalase, and aromatic scent of these plants. The use of lemongrass in superoxide dismutase (SOD) were purchased from Sigma curries in Asia and in spices in Africa is also related to Chemical Co. (St. Louis, MO, USA). Trolox (6-hydroxy- prevention of food spoilage, and the preservative properties 2,5,7,8-tetramethylchroman-2-carboxylic acid) was pur- of these plants are probably related to their high content of chased from Aldrich Chemical Co. (Milwaukee, WI, USA). essential oils.13–16 Nonetheless, isolated properties of the Water was purified using a Milli-QÒ system from Millipore different essential oil components of these medicinal plants, (Milford, MA, USA). All other reagents used in this study such as CT, have been poorly studied. were of highest analytical or high-performance liquid CT is produced by many plants traditionally used to treat chromatography grade. For all in vivo experiments the fol- different conditions by widespread populations around the lowing agents were used: CT [(RS)-(Æ)-CT, 98% purity, world, such as South America and Asia.17–19 Although CT Dierberger, Barra Bonito, Brazil], morphine hydrochloride has been identified, purified, and chemically well defined, its (Unia˜o Quı´mica, Sa˜o Paulo, Brazil), naloxone hydrochlo- biological and antioxidant properties have been very poorly ride (Neoquı´mica, Anapolis, Brazil), 37% formaldehyde explored. For instance, plants of the Cymbopogon genus, (Vetec, Rio de Janeiro, Brazil), Tween 80 (polyoxyethylene- which are rich in mono-, di-, and triterpenes, are widely used sorbitan monolate), and capsaicin (Sigma). Vehicle for an- to treat different forms of pain.20–24 Holanda Pinto et al.25 imals was 1 drop of Tween 80 (0.2%) dissolved in 0.9% demonstrated the analgesic effect of the triterpenoid a,b- NaCl solution. In those protocols the agents were injected amyrin, a compound closely related to CT. Also, CT and intraperitoneally at a dose volume of 1 mL=10 g. The related monoterpenoids were reported to inhibit cytochrome physiologic solution used for in vivo tests was composed of 26 P-450 CYP2B1 and other dehydrogenases, indicating that 150 mM NaCl, 4 mM KCl, 2 mM CaCl2,1mM MgCl2, such compounds may exert a diverse array of biological 10 mM glucose, and 10 mM HEPES, adjusted to pH 7.4 with actions. NaOH. Pain is a complex, multidimensional experience espe- cially relevant to the orofacial region because the face and Formalin test mouth have a particular biological and psychological Orofacial nociception was induced in mice by subcuta- meaning for each individual. Many of the most common neous injection of 20 mL of 2% formalin into the right upper types of pain occur in the orofacial region, and most diffi- lip (perinasal area), using a 27-gauge needle.27,29 This vol- culties in the management of conditions related to acute and ume and percentage concentration of formalin were selected chronic orofacial pain arise from a lack of understanding of from our pilot studies that showed a pain-related biphasic its mechanisms.27 Free radicals, especially nitric oxide behavioral response (face-rubbing) of great intensity at (NO), are also involved in the control of processes related to periods of 0–5 minutes (first phase) and 15–40 minutes pain because such species evoke cell signaling cascades (second phase). Pain was quantified at those periods by related to modulation of neuropathic and inflammatory measuring the time (in seconds) that the animals spent face- pain.28 In the present work, we investigated the anti- rubbing in the injected area with their fore- or hindpaws.27 nociceptive effect of CT and its redox properties. To assess the effects of test drugs, groups of rats (n ¼ 8 per group) were pretreated systemically with vehicle (1 drop of Tween 80 [0.2%] in distilled water, the solvent for CT) or CT MATERIALS AND METHODS (50, 100, and 200 mg=kg, i.p.), 0.5 hours before the local Animals injection of formalin. Morphine (3 mg=kg, i.p.), administered 30 minutes before the algogen, was included as the positive Male Swiss mice (weighing 30–36 g) and male Wistar control. In separate experiments, the possible involvement of rats (weighing 230–260 g), 2–3 months of age, were used opioid mechanism was assessed in the antinociception pro- throughout this study. The animals were randomly housed in duced by CT or morphine with naloxone (1.5 mg=kg, i.p.), an appropriate cages at 22 Æ 28C on a 12-hour light=dark cycle opioid antagonist, injected simultaneously. (lights on 6:00 a.m. to 6:00 p.m.) with free access to food and water. All experiments were carried out between 9:00 Capsaicin test a.m. and 2:00 p.m. in a quiet room. Experimental protocols were approved by the Animal Care and Use Committee The orofacial pain was induced by capsaicin administra- (CEPA=UFS number 12=08) at the Federal University of tion. Mice (n ¼ 8) were injected with capsaicin (20 mL, Sergipe, Aracaju, Brazil.
Recommended publications
  • Effect of Alkali Carbonate/Bicarbonate on Citral Hydrogenation Over Pd/Carbon Molecular Sieves Catalysts in Aqueous Media
    Modern Research in Catalysis, 2016, 5, 1-10 Published Online January 2016 in SciRes. http://www.scirp.org/journal/mrc http://dx.doi.org/10.4236/mrc.2016.51001 Effect of Alkali Carbonate/Bicarbonate on Citral Hydrogenation over Pd/Carbon Molecular Sieves Catalysts in Aqueous Media Racharla Krishna, Chowdam Ramakrishna, Keshav Soni, Thakkallapalli Gopi, Gujarathi Swetha, Bijendra Saini, S. Chandra Shekar* Defense R & D Establishment, Gwalior, India Received 18 November 2015; accepted 5 January 2016; published 8 January 2016 Copyright © 2016 by authors and Scientific Research Publishing Inc. This work is licensed under the Creative Commons Attribution International License (CC BY). http://creativecommons.org/licenses/by/4.0/ Abstract The efficient citral hydrogenation was achieved in aqueous media using Pd/CMS and alkali addi- tives like K2CO3. The alkali concentrations, reaction temperature and the Pd metal content were optimized to enhance the citral hydrogenation under aqueous media. In the absence of alkali, ci- tral hydrogenation was low and addition of alkali promoted to ~92% hydrogenation without re- duction in the selectivity to citronellal. The alkali addition appears to be altered the palladium sites. The pore size distribution reveals that the pore size of these catalysts is in the range of 0.96 to 0.7 nm. The palladium active sites are also quite uniform based on the TPR data. The catalytic parameters are correlated well with the activity data. *Corresponding author. How to cite this paper: Krishna, R., Ramakrishna, C., Soni, K., Gopi, T., Swetha, G., Saini, B. and Shekar, S.C. (2016) Effect of Alkali Carbonate/Bicarbonate on Citral Hydrogenation over Pd/Carbon Molecular Sieves Catalysts in Aqueous Media.
    [Show full text]
  • Redalyc.Degradation of Citronellol, Citronellal and Citronellyl Acetate By
    Electronic Journal of Biotechnology E-ISSN: 0717-3458 [email protected] Pontificia Universidad Católica de Valparaíso Chile Tozoni, Daniela; Zacaria, Jucimar; Vanderlinde, Regina; Longaray Delamare, Ana Paula; Echeverrigaray, Sergio Degradation of citronellol, citronellal and citronellyl acetate by Pseudomonas mendocina IBPse 105 Electronic Journal of Biotechnology, vol. 13, núm. 2, marzo, 2010, pp. 1-7 Pontificia Universidad Católica de Valparaíso Valparaíso, Chile Available in: http://www.redalyc.org/articulo.oa?id=173313806002 How to cite Complete issue Scientific Information System More information about this article Network of Scientific Journals from Latin America, the Caribbean, Spain and Portugal Journal's homepage in redalyc.org Non-profit academic project, developed under the open access initiative Electronic Journal of Biotechnology ISSN: 0717-3458 Vol.13 No.2, Issue of March 15, 2010 © 2010 by Pontificia Universidad Católica de Valparaíso -- Chile Received April 24, 2009 / Accepted November 6, 2009 DOI: 10.2225/vol13-issue2-fulltext-8 RESEARCH ARTICLE Degradation of citronellol, citronellal and citronellyl acetate by Pseudomonas mendocina IBPse 105 Daniela Tozoni Instituto de Biotecnologia Universidade de Caxias do Sul R. Francisco G. Vargas 1130 Caxias do Sul, RS, Brazil Jucimar Zacaria Instituto de Biotecnologia Universidade de Caxias do Sul R. Francisco G. Vargas 1130 Caxias do Sul, RS, Brazil Regina Vanderlinde Instituto de Biotecnologia Universidade de Caxias do Sul R. Francisco G. Vargas 1130 Caxias do Sul, RS, Brazil Ana Paula Longaray Delamare Universidade de Caxias do Sul R. Francisco G. Vargas 1130 Caxias do Sul, RS, Brazil Sergio Echeverrigaray* Universidade de Caxias do Sul R. Francisco G. Vargas 1130 Caxias do Sul, RS, Brazil E-mail: [email protected] Financial support: COREDES/FAPERGS, and D.
    [Show full text]
  • Effect of Thidiazuron on Terpene Volatile Constituents And
    molecules Article Effect of Thidiazuron on Terpene Volatile Constituents and Terpenoid Biosynthesis Pathway Gene Expression of Shine Muscat (Vitis labrusca × V. vinifera) Grape Berries 1, 1, 1 2 Wu Wang y, Muhammad Khalil-Ur-Rehman y, Ling-Ling Wei , Niels J. Nieuwenhuizen , Huan Zheng 1,* and Jian-Min Tao 1,* 1 College of Horticulture, Nanjing Agricultural University, Nanjing 210095, China; [email protected] (W.W.); [email protected] (M.K.-U.-R.); [email protected] (L.-L.W.) 2 The New Zealand Institute for Plant and Food Research Ltd. (PFR), Private Bag 92169, Auckland 1142, New Zealand; [email protected] * Correspondence: [email protected] (H.Z.); [email protected] (J.-M.T.); Tel.: +86-150-7784-8993 (H.Z.); +86-139-0516-0976 (J.-M.T.) These authors contributed equally in this work. y Received: 14 April 2020; Accepted: 26 May 2020; Published: 2 June 2020 Abstract: Volatile compounds are considered to be essential for the flavor and aroma quality of grapes. Thidiazuron (TDZ) is a commonly used growth regulator in grape cultivation that stimulates larger berries and prevents fruit drop. This study was conducted to investigate the effect of TDZ on the production of aroma volatiles and to identify the key genes involved in the terpene biosynthesis pathways that are affected by this compound. Treatment with TDZ had a negative effect on the concentration of volatile compounds, especially on monoterpenes, which likely impacts the sensory characteristics of the fruit. The expression analysis of genes related to the monoterpenoid biosynthesis pathways confirmed that treatment with TDZ negatively regulated the key genes DXS1, DXS3, DXR, HDR, VvPNGer and VvPNlinNer1.
    [Show full text]
  • Citronellol Cas No
    SUMMARY OF DATA FOR CHEMICAL SELECTION -CITRONELLOL CAS NO. 106-22-9 BASIS OF NOMINATION TO THE CSWG The nomination of citronellol to the CSWG is based on high production volume, widespread human exposure, and an unknown potential for adverse health effects from long-term administration. Citronellol came to the attention of the CSPG because of information supplied by the Food and Drug Administration (FDA) from a review of “GRAS” substances used as spices and food additives. According to the FDA data, citronellol is found in 17 different spices. It is also a common flavoring in beverages and foods and is one of the most widely used fragrance materials, having the sweet aroma of rose. Occupational exposure to citronellol in the United States is significant, estimated to be over 160,000 workers in 62 industries. Citronellol is present in high concentrations in citronella, geranium, and rose oils, accounting for additional human exposure. It is also closely related to citronellal and seven esters also having “GRAS” status. SELECTION STATUS ACTION BY CSWG : 7/16/97 Studies requested : - Metabolism studies - Mechanistic studies to include examination of the role of α 2u -globulin in transport - Carcinogenicity - In vitro cytogenetic analysis - In vivo micronucleus assay Priority : Moderate Rationale/Remarks : - High production levels - Widespread exposure as an ingredient in natural products - Lack of chronic toxicity data - Test in parallel with linalool INPUT FROM GOVERNMENT AGENCIES/INDUSTRY Dr. Dan Benz, Center for Food Safety and Applied Nutrition (CFSAN), Food and Drug Administration (FDA) and Dr. Ed Matthews (formerly with CFSAN) provided information on citronellol from FDA’s Priority-Based Assessment of Food Additives (PAFA) database.
    [Show full text]
  • Biochemistry of Terpenes and Recent Advances in Plant Protection
    International Journal of Molecular Sciences Review Biochemistry of Terpenes and Recent Advances in Plant Protection Vincent Ninkuu , Lin Zhang, Jianpei Yan, Zhenchao Fu, Tengfeng Yang and Hongmei Zeng * State Key Laboratory for Biology of Plant Diseases and Insect Pests, Institute of Plant Protection, Chinese Academy of Agricultural Sciences (IPP_CAAS), Beijing 100193, China; [email protected] (V.N.); [email protected] (L.Z.); [email protected] (J.Y.); [email protected] (Z.F.); [email protected] (T.Y.) * Correspondence: [email protected]; Tel.: +86-10-82109562 Abstract: Biodiversity is adversely affected by the growing levels of synthetic chemicals released into the environment due to agricultural activities. This has been the driving force for embracing sustainable agriculture. Plant secondary metabolites offer promising alternatives for protecting plants against microbes, feeding herbivores, and weeds. Terpenes are the largest among PSMs and have been extensively studied for their potential as antimicrobial, insecticidal, and weed control agents. They also attract natural enemies of pests and beneficial insects, such as pollinators and dispersers. However, most of these research findings are shelved and fail to pass beyond the laboratory and greenhouse stages. This review provides an overview of terpenes, types, biosynthesis, and their roles in protecting plants against microbial pathogens, insect pests, and weeds to rekindle the debate on using terpenes for the development of environmentally friendly biopesticides and herbicides. Keywords: terpenes; biosynthesis; phytoalexin; insecticidal; allelopathy Citation: Ninkuu, V.; Zhang, L.; Yan, J.; Fu, Z.; Yang, T.; Zeng, H. Biochemistry of Terpenes and Recent 1. Introduction Advances in Plant Protection. Int. J. Plants and a multitude of pathogenic microbes are in a constant battle for supremacy.
    [Show full text]
  • Citronella & Citronella Oil Profile New York State Integrated Pest Management Cornell Cooperative Extension Program
    http://hdl.handle.net/1813/56119 Citronella & Citronella Oil Profile New York State Integrated Pest Management Cornell Cooperative Extension Program Citronella & Citronella Oil Profile Active Ingredient Eligible for Minimum Risk Pesticide Use Brian P. Baker, Jennifer A. Grant, and Raksha Malakar-Kuenen1 New York State Integrated Pest Management, Cornell University, Geneva NY Active Ingredient Name: Citronella and U.S. EPA PC Code: 021901 Citronella oil CA DPR Chem Code: 143 Active Components: Citronellal, citronellol, geraniol, camphene, pinene, dipenthene, Other Names: Oil of citronella limonene, linalool and borneol Other Codes: EINECS: 289-753-6 (Ceylon), 294- CAS Registry #: 8000-29-1 954-7 (Java), FEMA: 2308 Summary: Citronella oil is derived from two perennial grasses of the Cymbopongon species. As a pesti- cide, the essential oil is primarily used as a mosquito repellent, but also has other insecticidal, acaricidal and herbicidal activity. It is not considered harmful to humans and pets but may cause skin irritation. Citronella can be toxic to pollinators. Pesticidal Uses: Repellent of mosquitoes and other biting insects; herbicide. Formulations and Combinations: Citronella may be used with other essential oils and botanical insecti- cides. Those eligible for exemption include cinnamon oil, clove oil, eugenol, lemongrass oil, and cinnamon oil. Registered products may contain the botanical neem. Paraffin, beeswax and other waxes may be added when used in insect repellent candles. Citronella in incense sticks may be combined with various wood powders, binders and other incense base ingredients. Gel formulations are made with vegetable gums, such as guar, tragacanth and gum arabic. Wetting agents and surfactants—including sodium lauryl sulfate, glycerol and gelatin—may also be used as formulants in exempt products.
    [Show full text]
  • Analgesic-Like Activity of Essential Oils Constituents
    Molecules 2011, 16, 2233-2252; doi:10.3390/molecules16032233 OPEN ACCESS molecules ISSN 1420-3049 www.mdpi.com/journal/molecules Review Analgesic-like Activity of Essential Oils Constituents Damião Pergentino de Sousa Department of Physiology, Federal University of Sergipe, CEP 49100-000, São Cristóvão, SE, Brazil; E-Mail: [email protected] Received: 4 January 2011; in revised form: 10 February 2011 / Accepted: 4 March 2011 / Published: 7 March 2011 Abstract: Research on neuroactive drugs is a pharmaceutical sector of high interest and growth. The discovery of efficient drugs that can relieve pain is a subject of research in the pharmaceutical industry and academic field because pain is a symptom of many diseases. This review will summarize results on the discovery of essential oil constituents with analgesic-like activity from the chemical and pharmacological perspectives. Overall, 43 bioactive compounds were selected in nociception models. Among them, 62.8% were monoterpenes, 18.6% sesquiterpenes and other constituents represented 18.6%. The data show the potential of this group of natural product chemicals as analgesic drugs that may be useful for therapeutic purposes. Keywords: analgesic; antinociceptive; essential oils; terpenes; natural products 1. Introduction Pain is defined as an unpleasant sensory and emotional experience associated with actual or potential tissue damage, or described in terms of such damage [1]. It is a sensation described as a multidimensional experience, in which several components are involved: motivational, emotional, sensory-discriminative, affective, and cognitive aspects [2]. Perception of pain and response to analgesic drugs are complex processes that involve multiple biochemical pathways. Each of these pathways is influenced by significant genetic factors that may modify pain perception and/or response to analgesics.
    [Show full text]
  • Degradation of Citronellol, Citronellal and Citronellyl Acetate by Pseudomonas Mendocina Ibpse 105
    Electronic Journal of Biotechnology ISSN: 0717-3458 Vol.13 No.2, Issue of March 15, 2010 © 2010 by Pontificia Universidad Católica de Valparaíso -- Chile Received April 24, 2009 / Accepted November 6, 2009 DOI: 10.2225/vol13-issue2-fulltext-8 RESEARCH ARTICLE Degradation of citronellol, citronellal and citronellyl acetate by Pseudomonas mendocina IBPse 105 Daniela Tozoni Instituto de Biotecnologia Universidade de Caxias do Sul R. Francisco G. Vargas 1130 Caxias do Sul, RS, Brazil Jucimar Zacaria Instituto de Biotecnologia Universidade de Caxias do Sul R. Francisco G. Vargas 1130 Caxias do Sul, RS, Brazil Regina Vanderlinde Instituto de Biotecnologia Universidade de Caxias do Sul R. Francisco G. Vargas 1130 Caxias do Sul, RS, Brazil Ana Paula Longaray Delamare Universidade de Caxias do Sul R. Francisco G. Vargas 1130 Caxias do Sul, RS, Brazil Sergio Echeverrigaray* Universidade de Caxias do Sul R. Francisco G. Vargas 1130 Caxias do Sul, RS, Brazil E-mail: [email protected] Financial support: COREDES/FAPERGS, and D. Tozoni held a CAPES scholarship during the development of this work. Keywords: biodegradation, citronellol catabolism, monoterpenes degradation, P. mendocina. Abbreviations: GC-MS: gas chromatography-mass spectrometry The purpose of this work was to stud the Terpenes or terpenoids are widespread in nature, and are biodegradation of citronellol, citronellal and citronellyl the most important component of the essential oil of many acetate by a soil Pseudomonas mendocina strain (IBPse higher plants (Loza-Tavera, 1999). These compounds are 105) isolated from a Cymbopogon windelandi field. This characterized by methyl-branched molecular structures strain efficiently used citronellol, citronellal, citronellyl derived from isoprene. Monoterpenes and their oxygenated acetate and myrcene as sole source of carbon, but was forms consist of two isoprene units (C10), and can be cyclic not able to grow on other 15 monoterpenoids evaluated.
    [Show full text]
  • Lawrence Berkeley National Laboratory Recent Work
    Lawrence Berkeley National Laboratory Recent Work Title HYDROCARBONS FROM PLANTS: BIOSYNTHESIS AND UTILIZATION Permalink https://escholarship.org/uc/item/7ss0z1rc Authors Taylor, S.E. Calvin, M. Publication Date 1986-09-01 eScholarship.org Powered by the California Digital Library University of California LBL-22294 Preprint ~.~ ITlI Lawrence Berkeley Laboratory Ii:II UNIVERSITY OF CALIFORNIA ·5' ~)' nr~i Elv[:DCHEMICAL BIODYNAMICS DIVISION '~-r L/, '\!HE!\·~CE NO' 1 B 1986 Submitted to Comments on Agricultural and Food Chemistry DOGU:''! ;:NTS SECTiON HYDROCARBONS FROM PLANTS: BIOSYNTHESIS AND UTILIZATION S.E. Taylor and M. Calvin September 1986 Prepared for the U.S. Department of Energy under Contract DE-AC03-76SF00098 , , DISCLAIMER ,.'," This document was prepared as an account of work sponsored by the United States Government. While this document is believed to contain correct information, neither the United States Government nor any agency thereof, nor the Regents of the University of California, nor any of their employees, makes any warranty, express or implied, or assumes any legal responsibility for the accuracy, completeness, or usefulness of any information, apparatus, product, or process disclosed, or represents that its use would not infringe privately owned rights. Reference herein to any specific commercial product, process, or service by its trade name, trademark, manufacturer, or otherwise, does not necessarily constitute or imply its endorsement, recommendation, or favoring by the United States Government or any agency thereof, or the Regents of the University of California. The view~ and opinions of aut~ors expressed herein do not necessarily state or reflect those of the United States Government or any agency thereof or the Regents of the University of California.
    [Show full text]
  • Characterization of the Substrate Specificity of Squalene- Hopene
    Characterization of the substrate specificity of squalene - hopene cyclases (SHCs) Untersuchungen zur Substratspezifität von Squalen -Hopen Zyklasen (SHCs) Von der Fakultät 3: Chemie der Universität Stuttgart zur Erlangung der Würde eines Doktors der Naturwissenschaften (Dr. rer. nat.) genehmigte Abhandlung Vorgelegt von Miriam Seitz aus Rastatt Hauptberichter: Prof. Dr. Bernhard Hauer Mitberichter: Prof. Dr. Bernd Plietker Vorsitzende: Prof. Dr. Cosima Stubenrauch Tag der mündlichen Prüfung: 6. Februar 2013 Institut für Technische Biochemie der Universität Stuttgart 2012 Die vorliegende Arbeit entstand auf Anregung und unter Anleitung von Herrn Prof. Dr. Bernhard Hauer in der Zeit von Oktober 2009 bis Dezember 2012 am Institut für technische Biochemie an der Universität Stuttgart. Im Rahmen dieser Dissertation wurden folgende Publikationen vorab veröffentlicht: “Substrate specificity of a novel squalene-hopene cyclase from Zymomonas mobilis ”; M. Seitz, J. Klebensberger, S. Siebenhaller, M. Breuer, G. Siedenburg, D. Jendrossek, B. Hauer; J. Mol. Cat. B: Enzymatic 2012 (84) 72 –77. “Activation -Independent Cyclization of Monoterpenoids” ; G. Siedenburg, D. Jendrossek, M. Breuer, B. Juhl, J. Pleiss, M. Seitz, J. Klebensberger, B. Hauer; Appl. Environ. Microbiol. 2012 (78) 1055 –1062. “Synthesis of Heterocyclic Terpenoids by Promiscuous Squalene-Hopene Cyclases” ; M. Seitz, P.-O. Syrén, L. Steiner, J.Klebensberger, B. M. Nestl, B. Hauer; ChemBioChem 2013 (14) 436-439. “Squalene hopene cyclases: highly promiscuous and evolvable catalysts
    [Show full text]
  • Natural Products Assessed in Animal Models for Orofacial Pain – A
    Revista Brasileira de Farmacognosia 27 (2017) 124–134 ww w.elsevier.com/locate/bjp Review Natural products assessed in animal models for orofacial pain – a systematic review a,b a,c a a Pollyana S. Siqueira-Lima , Juliane C. Silva , Jullyana S.S. Quintans , Angelo R. Antoniolli , a a a b,c Saravanan Shanmugam , Rosana S.S. Barreto , Márcio R.V. Santos , Jackson R.G.S. Almeida , d e a,∗ Leonardo R. Bonjardim , Irwin R.A. Menezes , Lucindo J. Quintans-Júnior a Laboratório de Neurociências e Ensaios Farmacológicos, Universidade Federal de Sergipe, São Cristóvão, SE, Brazil b Departamento de Farmácia, Universidade Estadual de Feira de Santana, Feira de Santana, BA, Brazil c Colegiado de Ciências Farmacêuticas, Universidade Federal do Vale do São Francisco, Petrolina, PE, Brazil d Faculdade de Odontologia de Baurú, Universidade de São Paulo, Baurú, SP, Brazil e Departamento de Quimica-Biologica, Federal University of Cariri, Crato, CE, Brazil a b s t r a c t a r t i c l e i n f o Article history: Orofacial pain is related to tissues of the head, face, neck and all the intraoral structures; it is rather debil- Received 10 February 2016 itating to the patient and also difficult to treat. There are relatively few studies dedicated to the use of Accepted 27 June 2016 natural products to alleviate orofacial pain in preclinical experiment models (performed in experimen- tal animals which provide support for clinical trials). Main objectives of the present systematic review Keywords: summarize the studies on natural products assessed in animal models for orofacial pain seeking to give Medicinal plants evidence to future development of new pharmaceutical products to manage the orofacial pain.
    [Show full text]
  • Conversion of (±)-Citronellal and Its Derivatives to (-)-Menthol Using Bifunctional Nickel Zeolite Catalysts
    Conversion of (±)-Citronellal and Its Derivatives …… (Indri Badria Adilina) CONVERSION OF (±)-CITRONELLAL AND ITS DERIVATIVES TO (-)-MENTHOL USING BIFUNCTIONAL NICKEL ZEOLITE CATALYSTS (Konversi (±)-Citronellal dan Turunannya Menjadi (-)-Mentol Menggunakan Katalis Nikel Zeolit Dwi-Fungsi) Indri Badria Adilina, Ralentri Pertiwi and Anny Sulaswatty Research Centre for Chemistry-Indonesian Institute of Sciences Puspiptek Area Serpong, Tangerang 15314, Indonesia e-mail: [email protected] Naskah diterima 19 September 2014, revisi akhir 6 April 2015 dan disetujui untuk diterbitkan 16 April 2015 ABSTRAK. (±)-Citronellal and its derivatives were converted to (-)-menthol by a one-pot reaction system using zeolite based nickel catalysts. The catalysts were prepared by immobilization of nickel on natural zeolite (NZ) or synthetic zeolite (ZSM- 5) by a simple cation exchange method. Calcination and hydrogen treatment procedures were able to significantly increase the surface area and pore volume of NZ based catalysts whereas negligible changes in the properties were observed for that of ZSM-5. Catalytic reactions were carried out at 70ºC by stirring the mixture in the air for cyclization of (±)-citronellal to (±)-isopulegol followed by hydrogenation towards the desired (-)-menthol at 2 Mpa of H2 pressure. The Ni/NZ catalyst was able to convert a (±)-citronellal derivative yielding 9% (-)-menthol (36% selectivity) with conversion up to 24%, whereas Ni/ZSM5 catalyst directly converted 65% (±)-citronellal to give 4% menthol (6% selectivity). These zeolite based catalysts are therefore potential materials for the conversion of biomass feed stock to value-added chemicals. Keywords: citronellal, citronella oil, menthol, nickel catalyst, zeolite ABSTRACT. (±)-Sitronelal dan turunannya telah dikonversi menjadi (-)-mentol dalam sistem reaksi one-pot menggunakan katalis nikel berbasis zeolit.
    [Show full text]