Synthesis and Analysis of Zingerone Analogues As Fruit Fly Attractants

Total Page:16

File Type:pdf, Size:1020Kb

Synthesis and Analysis of Zingerone Analogues As Fruit Fly Attractants Synthesis and Analysis of Zingerone Analogues as Fruit Fly Attractants By Benjamin L. Hanssen Department of Chemistry and Biomolecular Sciences Date of Submission: 9 October 2015 Declaration of Originality I, Benjamin L. Hanssen, declare that this work contains no material which has been accepted for the award of any other degree or diploma in any university or other tertiary institution and, to the best of my knowledge and belief, contains no material previously published or written by another person, except where due reference has been made in the text. Benjamin L. Hanssen Date ii Table of Contents Declaration of Originality .......................................................................................................... ii Acknowledgements ................................................................................................................... iv Table of Abbreviations ............................................................................................................... v Abstract ..................................................................................................................................... vi Chapter 1. Introduction .............................................................................................................. 1 1.1 Fruit Flies – Life Cycle and Economic Importance ......................................................... 1 1.2 Fruit Fly Control Methods................................................................................................ 3 1.2.1 Organophosphate Insecticides ................................................................................... 3 1.2.2 Alternative Control Methods: MT and MAT ............................................................ 3 1.3 The Chemical Basis of Lure Attraction ............................................................................ 5 1.4 Methyl Eugenol and Raspberry Ketone as Chemical Lures ............................................ 5 1.5 Lure Attractiveness .......................................................................................................... 6 1.5.1 Intrinsic Attractiveness .............................................................................................. 7 1.5.2 Volatility .................................................................................................................... 7 1.6 Chemical Lure and Receptor SAR Investigations ............................................................ 9 1.6.1 Methyl Eugenol Receptor .......................................................................................... 9 1.6.2 Raspberry Ketone Receptor .................................................................................... 10 1.7 Zingerone as a Chemical Lure ....................................................................................... 11 1.7.1 Reasons for Zingerone Attraction ........................................................................... 13 1.8 Implications of Zingerone for Fruit Fly Control ............................................................ 14 1.9 Aims and Scope of Study ............................................................................................... 14 Chapter 2. Experimental Methods ............................................................................................ 15 2.1 Synthesis of Zingerone Analogues ................................................................................. 15 2.2 Vapour Pressure Measurements ..................................................................................... 23 2.3 Biological Testing .......................................................................................................... 24 2.3.1 Electroantennography (EAG) .................................................................................. 24 2.3.2 Laboratory Cage Bioassays ..................................................................................... 25 Chapter 3. Results and Discussion ........................................................................................... 26 3.1 Selection and Synthesis of Zingerone Analogues .......................................................... 26 3.1.1 Selection of Zingerone Analogues .......................................................................... 26 3.1.2 Proposed Synthetic Methods ................................................................................... 29 3.1.3 Discussion of Synthetic Methods ............................................................................ 32 3.2 Vapour Pressure Measurements ..................................................................................... 40 3.3 Biological Testing .......................................................................................................... 47 3.3.1 Electroantennography (EAG) .................................................................................. 47 3.3.2 Laboratory Cage Bioassays ..................................................................................... 50 Chapter 4. Conclusions and Future Directions ......................................................................... 53 Chapter 5. References .............................................................................................................. 56 Appendix .................................................................................................................................. 62 iii Acknowledgements I would like to thank my supervisors Ian Jamie, Joanne Jamie, Soo Jean Park, and Phil Taylor who have provided much support and guidance throughout this year. They have been an invaluable source of knowledge and given me great insight into what research can involve. Soo deserves special acknowledgement for her immeasurable help, especially at the beginning as I was settling in with the project and lab. I cannot imagine how much harder this year would have been without Soo’s support and practical experience and knowledge. I would also like to thank Chris McRae for the use of and fixing the DSC amongst other things, without which the vapour pressure work would have been that much more difficult. Thank you to my friends Gin and Nathan for their company in the lab, the discussions that made periods of setbacks and monotony bearable, and their support and encouragement to make it through the year. Last but not least, I thank my family for all their never-ending support and encouragement this year. iv Table of Abbreviations ADI Acceptable daily intake APVMA Australian Pesticide and Veterinary Medicines Authority ARfD Acute reference dose ATR-IR Attenuated total reflectance-infrared DCC N,N’-Dicyclohexylcarbodiimide DCM Dichloromethane DMAP 4-Dimethylaminopyridine DSC Differential scanning calorimetry EAG Electroantennography EI Electron ionisation GC-FID Gas chromatography-flame ionisation detector GC-MS Gas chromatography-mass spectrometry MAT Male annihilation technique MT Mass trapping NMR Nuclear magnetic resonance SAR Structure-activity relationship TLC Thin layer chromatography v Abstract Fruit fly species have a devastating impact on food production in Australia and other countries. With new restrictions on the use of certain organophosphate insecticides, other control methods, such as male annihilation technique (MAT), will be more important for crop protection. MAT depends on effective male lures to attract pest insects to toxicants. Zingerone is a natural product that is attractive to males of Bactrocera jarvisi, a species that responds only weakly to other lures. In a step towards more effective lures, a series of zingerone analogues were synthesised and characterised. Many analogues were synthesised by an Aldol-hydrogenation synthetic route. Volatility is considered an important factor in lure attraction and the measurement of the volatility of the analogues by differential scanning calorimetry showed that fluorinated compounds have a 7-10-fold greater vapour pressure than corresponding non- fluorinated compounds. Unexpectedly, the acetyl and formyl esters of zingerone were half as volatile as zingerone. Electroantennography experiments with B. tryoni and B. jarvisi indicated that fluorinated compounds generally produce a greater response and the two species have vastly different preferences for the methylenedioxy moiety. Limited laboratory cage bioassays conducted with B. tryoni indicated that some of the fluorinated compounds tended to elicit a positive response. vi Chapter 1. Introduction Fruit flies are a significant pest of horticultural crops, and of particular concern are those species that have an impact upon food production. The Queensland fruit fly (Bactrocera tryoni) is the most serious pest fruit fly species in Australia with a very wide variety of host crops, ranging from citrus to nuts, tomatoes, and stone fruits.1-3 This species of fruit fly is also known to infest at least 60 wild, non-commercial plants.1 B. tryoni is present across northern Australia from Broome to north-west Queensland and eastern Australia from Cape York to south of Sydney. It is also present intermittently in Adelaide and Victoria.1, 4 In Australia, Jarvis’ fruit fly (B. jarvisi) is a moderate pest fruit fly present from northern Australia to northern New South Wales.4-6 It is known to infest at least 83 wild and commercial hosts, of which mangoes are the most susceptible commercial crop.5-6 Recent restrictions on the use of insecticides to control fruit flies,2, 7-8 such as B. tryoni and B. jarvisi, means that other control methods will
Recommended publications
  • 6-Paradol and 6-Shogaol, the Pungent Compounds of Ginger
    International Journal of Molecular Sciences Article 6-Paradol and 6-Shogaol, the Pungent Compounds of Ginger, Promote Glucose Utilization in Adipocytes and Myotubes, and 6-Paradol Reduces Blood Glucose in High-Fat Diet-Fed Mice Chien-Kei Wei 1,†, Yi-Hong Tsai 1,†, Michal Korinek 1, Pei-Hsuan Hung 2, Mohamed El-Shazly 1,3, Yuan-Bin Cheng 1, Yang-Chang Wu 1,4,5,6, Tusty-Jiuan Hsieh 2,7,8,9,* and Fang-Rong Chang 1,7,9,* 1 Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807, Taiwan; [email protected] (C.-K.W.); [email protected] (Y.-H.T.); [email protected] (M.K.); [email protected] (M.E.-S.); [email protected] (Y.-B.C.); [email protected] (Y.-C.W.) 2 Graduate Institute of Medicine, College of Medicine, Kaohsiung Medical University, Kaohsiung 807, Taiwan; [email protected] 3 Department of Pharmacognosy and Natural Products Chemistry, Faculty of Pharmacy, Ain-Shams University, Cairo 11566, Egypt 4 School of Pharmacy, College of Pharmacy, China Medical University, Taichung 404, Taiwan 5 Chinese Medicine Research and Development Center, China Medical University Hospital, Taichung 404, Taiwan 6 Center for Molecular Medicine, China Medical University Hospital, Taichung 404, Taiwan 7 Department of Marine Biotechnology and Resources, College of Marine Sciences, National Sun Yat-sen University, Kaohsiung 804, Taiwan 8 Lipid Science and Aging Research Center, Kaohsiung Medical University, Kaohsiung 807, Taiwan 9 Research Center for Environmental Medicine, Kaohsiung Medical University, Kaohsiung 807, Taiwan * Correspondence: [email protected] (T.-J.H.); [email protected] (F.-R.C.); Tel.: +886-7-312-1101 (ext.
    [Show full text]
  • Isolation and Characterization of Natural
    ABSTRACT OF THE DISSERTATION ISOLATION AND CHARACTERIZATION OF NATURAL PRODUCTS FROM GINGER AND ALLIUM URSINUM BY HOU WU Dissertation Director: Dr. Chi-Tang Ho Phenolic compounds from natural sources are receiving increasing attention recent years since they were reported to have a remarkable spectrum of biological activities including antioxidant, anti-inflammatory and anti-carcinogenic activities. They may have many health benefits and can be considered possible chemo- preventive agents against cancer. In this research, we attempted to isolate and characterize phenolic compounds from two food sources: ginger and Allium ursinum. Solvent extraction and a series of column chromatography methods were used for isolation of compounds, while structures were elucidated by integration of data from MS, 1H-NMR, 13C-NMR, HMBC and HMQC. Antioxidant activities were evaluated by DPPH method and anti- inflammatory activities were assessed by nitric oxide production model. Ginger is one of most widely used spices. It has a long history of medicinal use dating back 2500 years. Although there have been many reports concerning ii chemical constituents and some biological activities of ginger, most works used ginger extracts or focused on gingerols to study the biological activities of ginger. We suggest that the bioactivities of shogaols are also very important since shogaols are more stable than gingerols and a considerable amount of gingerols will be converted to shogaols in ginger products. In present work, eight phenolic compounds were isolated and identified from ginger extract. They included 6-gingerol, 8-gingerol, 10- gingerol, 6-shogaol, 8—shogaols, 10-shogaol, 6-paradol and 1-dehydro-6-gingerdione. DPPH study showed that 6-shogaol had a comparable antioxidant activity compared with 6-gingerol, the 50% DPPH scavenge concentrations of both compounds were 21 µM.
    [Show full text]
  • Ginger, the Genus Zingiber {P. N. Ravindran}
    Ginger The Genus Zingiber Ginger The Genus Zingiber Edited by P.N. Ravindran and K. Nirmal Babu Medicinal and Aromatic Plants — Industrial Profiles CRC PRESS Boca Raton London New York Washington, D.C. Library of Congress Cataloging-in-Publication Data Ginger : the genus Zingiber / edited by P.N. Ravindran, K. Nirmal Babu. p. cm.—(Medicinal and aromatic plants—industrial profiles; v. 41) Includes bibliographical references (p. ). ISBN 0-415-32468-8 (alk. Paper) 1. Ginger. I. Ravindran, P.N. II. Nirmal Babu, K. III. Series. SB304.G56 2004 633.8'3—dc22 2004055370 This book contains information obtained from authentic and highly regarded sources. Reprinted material is quoted with permission, and sources are indicated. A wide variety of references are listed. Reasonable efforts have been made to publish reliable data and information, but the author and the publisher cannot assume responsibility for the validity of all materials or for the consequences of their use. Neither this book nor any part may be reproduced or transmitted in any form or by any means, electronic or mechanical, including photocopying, microfilming, and recording, or by any information storage or retrieval system, without prior permission in writing from the publisher. All rights reserved. Authorization to photocopy items for internal or personal use, or the personal or internal use of specific clients, may be granted by CRC Press, provided that $1.50 per page photocopied is paid directly to Copyright Clearance Center, 222 Rosewood Drive, Danvers, MA 01923 USA. The fee code for users of the Transactional Reporting Service is ISBN 0-415-32468-8/05/$0.00+$1.50.
    [Show full text]
  • AOAC SMPR® 2017.012 Standard Method Performance Requirements
    AOAC SMPR® 2017.012 Cosmetic Act §201(ff) [U.S.C. 321 (ff)]. Dietary ingredients are conventionally presented as powders or liquids. Dietary supplement.—A product containing a dietary ingredient Standard Method Performance Requirements intended for ingestion to supplement the diet. Dietary supplements (SMPRs) for Quantitation of Select Nonvolatile containing dietary ingredients are commonly marketed as tablets, Ginger Constituents capsules, softgels, tinctures, or other finished dosage forms. Limit of quantitation (LOQ).—The minimum content of analyte in a given matrix that can be reliably and precisely quantitated in Intended Use: Control of Incoming Ingredients and agreement with the requirements set forth in this SMPR. Finished Products Repeatability.—Statistical variation in the analytical outcome arising when the maximum control over the analytical methodology 1 Purpose is afforded. Replicate analyses are performed by the same operator AOAC SMPRs describe the minimum recommended within a short time period using the same instrumentation. performance characteristics to be used during the evaluation of a Expressed as the repeatability standard deviation (SDr) or % method. The evaluation may be an on-site verification, a single- repeatability relative standard deviation (%RSDr). laboratory validation, or a multi-site collaborative study. SMPRs Reproducibility.—Statistical variation in the analytical outcome are written and adopted by AOAC stakeholder panels composed influenced by typical laboratory variables. Replicate analyses are of representatives from industry, regulatory organizations, contract conducted on different days by different operators using different laboratories, test kit manufacturers, and academic institutions. sets of equipment, occasionally in different physical locations. AOAC SMPRs are used by AOAC expert review panels in their Expressed as the reproducibility standard deviation (SDR) or % evaluation of validation study data for methods being considered reproducibility relative standard deviation (%RSDR).
    [Show full text]
  • Tert-Butyldimethylsilyl Ether-Protected Zingerone a 1-L Round Botto
    Saha et al Supplemental Information (Synthetic Experimental) tert-Butyldimethylsilyl ether-protected Zingerone A 1-L round bottom flask was charged with zingerone (10 g, 51.5 mmol) and the solid was subsequently dissolved in dry methylene chloride (400 mL) with stirring at room temperature. To this mixture was added imidazole (7.01 g, 103.0 mmol) and the reaction stirred for ½ hour. To the reaction was then added tert-butyldimethylsilyl chloride (7.76 g, 51.5 mmol) in one portion and the reaction was left to stir overnight under an atmosphere of N2 (g). The reaction was quenched by the addition of a saturated ammonium chloride solution (250 mL) and the aqueous layer was extracted with methylene chloride (2 x 100 mL). The combined organic layers were then washed with water (1 x 200 mL) and a saturated brine solution (2 x 200 mL). The organic layer was then dried over Na2SO4, decanted, and the excess solvent removed in vacuo. The crude oil was purified by column chromatography (silica gel; eluent: Methylene chloride) to yield the 16.75 g of pure product as a colorless oil (99% yield). 1H NMR (400 MHz, CDCl3): δ 0.12 (6H, s, Si-CH3), 0.97 (9H, s, C-(CH3)3), 2.10 (3H, s, O=C-CH3), 2.71 (2H, ddd, J = 2.0, 6.3, and 9.3 Hz, -CH2-), 2.80 (2H, dt, J = 2.0 and 5.1 Hz, -CH2-), 3.76 (3H, s, -OCH3), 6.59 (1H, dd, J = 2.1 and 8.0 Hz, ArH), 6.65 (1H, d, J = 2.1 Hz, ArH), 6.72 (1H, d, J = 8.0 Hz, ArH); 13 C NMR (75 MHz, CDCl3) δ -4.44, 18.64, 25.94, 29.74, 30.39, 45.67, 55.72, 112.60, 120.44, + 120.98, 134.62, 143.45, 150.95, 208.51; HRMS (ESI+) calcd for C17H29O3Si [M+H ]: 309.18800, found: 309.18830.
    [Show full text]
  • Efficient Production of the Flavoring Agent Zingerone and of Both (R)- and (S)-Zingerols Via Green Fungal Biocatalysis
    Int. J. Mol. Sci. 2014, 15, 22042-22058; doi:10.3390/ijms151222042 OPEN ACCESS International Journal of Molecular Sciences ISSN 1422-0067 www.mdpi.com/journal/ijms Article Efficient Production of the Flavoring Agent Zingerone and of both (R)- and (S)-Zingerols via Green Fungal Biocatalysis. Comparative Antifungal Activities between Enantiomers Laura A. Svetaz 1, Melina G. Di Liberto 1, María M. Zanardi 2, Alejandra G. Suárez 2 and Susana A. Zacchino 1,* 1 Pharmacognosy Area, School of Biochemical and Pharmaceutical Sciences, National University of Rosario, Suipacha 531, 2000 Rosario, Argentina; E-Mails: [email protected] (L.A.S.); [email protected] (M.G.D.L.) 2 Institute of Chemistry Rosario (IQUIR)-CONICET, School of Biochemical and Pharmaceutical Sciences, National University of Rosario, Suipacha 531, 2000 Rosario, Argentina; E-Mails: [email protected] (M.M.Z.); [email protected] (A.G.S.) * Author to whom correspondence should be addressed; E-Mail: [email protected]; Tel./Fax: +54-341-4375315. External Editor: James H. Clark Received: 8 October 2014; in revised form: 11 November 2014 / Accepted: 12 November 2014 / Published: 1 December 2014 Abstract: Zingerone (1) and both chiral forms of zingerol (2) were obtained from dehydrozingerone (3) by biotransformation with filamentous fungi. The bioconversion of 3 with A. fumigatus, G. candidum or R. oryzae allowed the production of 1 as the sole product at 8 h and in 81%–90% at 72 h. In turn, A. flavus, A. niger, C. echinulata, M. circinelloides and P. citrinum produced 1 at 8 h, but at 72 h alcohol 2 was obtained as the major product (74%–99%).
    [Show full text]
  • 6-Paradol, a Vital Compound of Medicinal Significance: a Concise Report
    International Journal of Research and Review Vol.7; Issue: 10; October 2020 Website: www.ijrrjournal.com Review Article E-ISSN: 2349-9788; P-ISSN: 2454-2237 6-Paradol, a Vital Compound of Medicinal Significance: A Concise Report Seba M C, Anatt Treesa Mathew, Sheeja Rekha, Prasobh G R Department of Pharmaceutical Chemistry, Sree Krishna College of Pharmacy and Research Centre, Parassala, Kerala, India Corresponding Author: Seba M C ABSTRACT aromatic spice which extends a special flavor and zest to our food. Ginger is the Herbal medicines have been preferred for underground rhizome of the ginger plant. the treatment of numerous disorders in the This perennial herb is largely grown as both world since a very early age owing to easily a spice and a condiment. [1] Besides, being available and fewer side effect. Ginger is a used to give beautiful aroma to Indian food, traditional medicine, having some active [2] ginger is also used as a potent medicine. ingredients used for the treatment of It has always been appreciated for its aroma, numerous diseases. During recent research culinary, and, above all, distinct medicinal on ginger, various ingredients like properties. zingerone, shogaol, and paradol have been It is widely known to treat a number obtained from it. Paradols are phenolic of different diseases throughout the world. It ketones which are structurally related to is due to varied phytochemistry of ginger gingerols and shogaols. Zingerone which is that it has large health benefits. It contains also known as 0-paradol, is a paradol various minerals and vitamins as well as analogue and the major pungent component enzymes like zingibain, a proteolytic of ginger.
    [Show full text]
  • LXIV.-The Pungent P?*Inciples of Ginger. Part I. a New Ketone, Zingerone (4-Hydroxy-3-Methoxy- Phenylethyl Methyl Ketone) Occurring in Ginger
    View Article Online / Journal Homepage / Table of Contents for this issue NOMURA : THE PUNGENT PRINCIPLES OB GINGER. PART I. 769 LXIV.-The Pungent P?*inciples of Ginger. Part I. A New Ketone, Zingerone (4-Hydroxy-3-methoxy- phenylethyl Methyl Ketone) occurring in Ginger. By HIROSHINOMURA. THRESHassigned the name '' gingerol " to the pungent principle of ginger, and Garnett and Grier (Piitarm. J., 1907, [iv], 25, 118) claimed to have isolated it. However, no account of an investiga- tion of its composition .and constitution is to be found in the literature, and the present work was undertaken to determine the constitution of the pungent principle. The new ketone, to which the name " zingerone" is assigned, was obtained by extracting ginger with ether, followed by the treatment deecribed on p. 770, and was proved to have the formula CllH1403. It yields monobenzoyl and monoacetyl derivatives, and the existence of one methoxyl group in it was proved. The methyl derivative, CI2Hl6O3,is readily converted into its oxime, C12H170,N, by hydroxylamine, which points to the presence of one carbonyl group. When the methyl derivative is oxidised with potassium permanganate in alkaline solution, veratric acid is obtained, and therefore the new ketone must be a 1 :3: 4- derivative of benzene. Since sodium hydrogen sulphite combines with the new ketone and with its methyl derivative and the latter is oxidisable with diffi- culty by an ammoniacal solution of silver nitrate, the group, CO-CH,, appears to exist in both compounds. If this is the case, the constitutional formula of the methyl derivative must be either Published on 01 January 1917.
    [Show full text]
  • Background and Fitness for Purpose for Ginger
    AOAC Stakeholder Panel on Dietary Supplements: Background and Fitness for Purpose for Ginger Anton Bzhelyansky AOAC 2016 Annual Meeting – Dallas, TX, USA SPDS September 16, 2016 Ginger Plant The ginger plant is a herbaceous perennial grown as an annual crop. The plant is erect, has many fibrous roots, aerial shoots (pseudostem) with leaves, and the underground stem (rhizome). Ginger (Zingiber officinale Roscoe) is a sterile, reed-like plant with a pungenttd and aromati tihic rhizome on whi hihitlifch it relies for vege ttitative propagation. The plant is a cultigen, that is, it is only known from cultivation. Its wild origins are not known with certainty but are believed to be India or South-East Asia. Ginger rhizome, known as Rhizoma Zingiberis in pharmacy is used in several traditional systems of medicine, including Traditional Chinese Medicine, Ayurveda and Western herbal medicine. Its traditional uses cover a great variety of complaints including dyspepsia, flatulence and colic, nausea and vomiting, colds and flu, migraine, as well as muscular and rheumatic disorders. Wohlmuth, H 2008, 'Phytochemistry and pharmacology of plants from the ginger family, Zingiberaceae', PhD thesis, Southern Cross University, Lismore, NSW. Ginger Rhizome Production, Processing and Chemical Composition Ginger Production* Ginger is one of the earliest important species grown in the Western hemisphere reported to be a native of Southeast Asia. Gingqger requires a warm tem perature (29-35 degree Celsius) and a humid climate for growth. It also requires a distinctive pattern of rainfall of at least 150 to 200 cm during the growing period and no rainfall a month prior to harvest.
    [Show full text]
  • Zingiber Officinale Roscoe
    foods Review Bioactive Compounds and Bioactivities of Ginger (Zingiber officinale Roscoe) Qian-Qian Mao 1, Xiao-Yu Xu 1, Shi-Yu Cao 1, Ren-You Gan 2,* , Harold Corke 2, Trust Beta 3,4 and Hua-Bin Li 1,* 1 Guangdong Provincial Key Laboratory of Food, Nutrition and Health, Department of Nutrition, School of Public Health, Sun Yat-sen University, Guangzhou 510080, China; [email protected] (Q.-Q.M.); [email protected] (X.-Y.X.); [email protected] (S.-Y.C.) 2 Department of Food Science & Technology, School of Agriculture and Biology, Shanghai Jiao Tong University, Shanghai 200240, China; [email protected] 3 Department of Food & Human Nutritional Sciences, University of Manitoba, Winnipeg, MB R3T 2N2, Canada; [email protected] 4 Richardson Centre for Functional Foods and Nutraceuticals, University of Manitoba, Winnipeg, MB R3T 2N2, Canada * Correspondence: [email protected] (R.-Y.G.); [email protected] (H.-B.L.); Tel.: +86-21-3420-8517 (R.-Y.G.); +86-20-873-323-91 (H.-B.L.) Received: 12 May 2019; Accepted: 28 May 2019; Published: 30 May 2019 Abstract: Ginger (Zingiber officinale Roscoe) is a common and widely used spice. It is rich in various chemical constituents, including phenolic compounds, terpenes, polysaccharides, lipids, organic acids, and raw fibers. The health benefits of ginger are mainly attributed to its phenolic compounds, such as gingerols and shogaols. Accumulated investigations have demonstrated that ginger possesses multiple biological activities, including antioxidant, anti-inflammatory, antimicrobial, anticancer, neuroprotective, cardiovascular protective, respiratory protective, antiobesity, antidiabetic, antinausea, and antiemetic activities.
    [Show full text]
  • Vanilloids Hamper Caenorhabditis Elegans Response to Noxious Heat
    bioRxiv preprint doi: https://doi.org/10.1101/2020.09.10.291237; this version posted September 11, 2020. The copyright holder for this preprint (which was not certified by peer review) is the author/funder. All rights reserved. No reuse allowed without permission. Vanilloids Hamper Caenorhabditis elegans Response to Noxious Heat Bruno Nkambeu1,2, Jennifer Ben Salem1,2,3 and Francis Beaudry1,2* 1- Groupe de Recherche en Pharmacologie Animal du Québec (GREPAQ), Département de Biomédecine Vétérinaire, Faculté de Médecine Vétérinaire, Université de Montréal, Saint-Hyacinthe, Québec, Canada 2- Centre de recherche sur le cerveau et l’apprentissage (CIRCA), Université de Montréal, Montréal, Québec, Canada 3- Institut des Maladies Métaboliques et Cardiovasculaires, INSERM UMR1048, Université de Toulouse, France *Corresponding author: Francis Beaudry, Ph.D. Professor of analytical pharmacology Département de Biomédecine Vétérinaire Faculté de Médecine Vétérinaire Université de Montréal 3200 Sicotte Saint-Hyacinthe, QC Canada J2S 2M2 Email: [email protected] Keywords: Caenorhabditis elegans, Eugenol, Vanillin, Zingerone, Vanilloids, Nociception, Transient receptor potential cation channel 1 bioRxiv preprint doi: https://doi.org/10.1101/2020.09.10.291237; this version posted September 11, 2020. The copyright holder for this preprint (which was not certified by peer review) is the author/funder. All rights reserved. No reuse allowed without permission. Abstract Eugenol, a known vanilloid, was frequently used in dentistry as a local analgesic in addition, antibacterial and neuroprotective effects were also reported. Eugenol, capsaicin and many vanilloids are interacting with the transient receptor potential vanilloid 1 (TRPV1) in mammals and are activated by noxious heat. The pharmacological manipulation of the TRPV1 has been shown to have therapeutic value.
    [Show full text]
  • EAFUS: a Food Additive Database
    U. S. Food and Drug Administration Center for Food Safety and Applied Nutrition Office of Premarket Approval EAFUS: A Food Additive Database This is an informational database maintained by the U.S. Food and Drug Administration (FDA) Center for Food Safety and Applied Nutrition (CFSAN) under an ongoing program known as the Priority-based Assessment of Food Additives (PAFA). It contains administrative, chemical and toxicological information on over 2000 substances directly added to food, including substances regulated by the U.S. Food and Drug Administration (FDA) as direct, "secondary" direct, and color additives, and Generally Recognized As Safe (GRAS) and prior-sanctioned substances. In addition, the database contains only administrative and chemical information on less than 1000 such substances. The more than 3000 total substances together comprise an inventory often referred to as "Everything" Added to Food in the United States (EAFUS). This list of substances contains ingredients added directly to food that FDA has either approved as food additives or listed or affirmed as GRAS. Nevertheless, it contains only a partial list of all food ingredients that may in fact be lawfully added to food, because under federal law some ingredients may be added to food under a GRAS determination made independently from the FDA. The list contains many, but not all, of the substances subject to independent GRAS determinations. The list below is an alphabetical inventory representing only five of 196 fields in FDA/CFSAN's PAFA database. To obtain the entire database, including abstractions of over 7,000 toxicology studies performed on substances added to food as well as a search engine to locate desired information, order Food Additives: Toxicology, Regulation, and Properties, available in CD-ROM format from CRC Press.
    [Show full text]