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Retention Indices for Frequently Reported Compounds of Plant Essential Oils
Retention Indices for Frequently Reported Compounds of Plant Essential Oils V. I. Babushok,a) P. J. Linstrom, and I. G. Zenkevichb) National Institute of Standards and Technology, Gaithersburg, Maryland 20899, USA (Received 1 August 2011; accepted 27 September 2011; published online 29 November 2011) Gas chromatographic retention indices were evaluated for 505 frequently reported plant essential oil components using a large retention index database. Retention data are presented for three types of commonly used stationary phases: dimethyl silicone (nonpolar), dimethyl sili- cone with 5% phenyl groups (slightly polar), and polyethylene glycol (polar) stationary phases. The evaluations are based on the treatment of multiple measurements with the number of data records ranging from about 5 to 800 per compound. Data analysis was limited to temperature programmed conditions. The data reported include the average and median values of retention index with standard deviations and confidence intervals. VC 2011 by the U.S. Secretary of Commerce on behalf of the United States. All rights reserved. [doi:10.1063/1.3653552] Key words: essential oils; gas chromatography; Kova´ts indices; linear indices; retention indices; identification; flavor; olfaction. CONTENTS 1. Introduction The practical applications of plant essential oils are very 1. Introduction................................ 1 diverse. They are used for the production of food, drugs, per- fumes, aromatherapy, and many other applications.1–4 The 2. Retention Indices ........................... 2 need for identification of essential oil components ranges 3. Retention Data Presentation and Discussion . 2 from product quality control to basic research. The identifi- 4. Summary.................................. 45 cation of unknown compounds remains a complex problem, in spite of great progress made in analytical techniques over 5. -
Detecting Traces of Methyl Eugenol in Essential Oils
Detecting traces of methyl eugenol in essential oils Ian Southwella,Mike Russellband Noel Daviesc Introduction Regulatory authorities are becoming more concerned about even low levels of suspected toxins in fl avour, fragrance and medicinal applications1. For example, allyl alkoxybenzenes (eg safrole, estragole (methyl chavicol), methyl eugenol), common constituents of many essential oils2,3, are of concern because high doses have caused cancer in rodents4-6. This concern is often exaggerated considering that: ► safety threshold doses some 1000 times less than the offending concentration recommended (eg IFRA Standards5) ► carcinogenesis is not always considered a threshold phenomenon7-9 ► the validity of dose extrapolation from rodents to humans is uncertain10-11 ► many complete essential oils also contain anti-carcinogenic congeners12-14 Hence reliable methods for the determination of trace quantities of allyl alkoxybenzenes in essential oils and formulated products are essential. Determinations Gas Chromatography using FID and MS detection Because of the absence of competing mass spectral ions illustrated the complexity of these essential oils and the from Melaleuca oil components, GCMS in SIM mode using diffi culties encountered in locating trace constituents. the m/z 178 ion (Varian Factor-Four VF-5ms, 30m x 0.25mm id, 0.25 μm fi lm) facilitated the determination of methyl Using tea tree oil, “Oil of Melaleuca, terpinen-4-ol type” as eugenol (Figure 2). a model, careful column selection for GC-FID (DB 1701 Length 60 m x 0.25 mm Dia x 0.25 μm fi lm (mid polarity) ) Such SIM traces, although excellent for determining analytes facilitated the separation and determination of methyl like methyl eugenol, give a false impression of the complexity eugenol to the ppm level (Figure 1). -
Chavicol, As a Larva-Growth Inhibitor, from Viburnum Japonicum Spreng
Agr. Biol. Chem., 40 (11), 2283•`2287, 1976 Chavicol, as a Larva-growth Inhibitor, from Viburnum japonicum Spreng. Hajime OHIGASHI and Koichi KOSHIMIZU Department of Food Science and Technology. Kyoto University, Kyoto Japan Received July 22, 1976 Chavicol was isolated as a drosophila larva-growth inhibitor from the leaves of Viburnum japonicum Spreng. The inhibitory activities of chavicol and its related compounds against drosophila larvae and adults were examined. To obtain biologically active substances assignable to allylic, terminal olefinic, a hydrox against insects from plants, we recently devised yl, an olefinic and 1, 4-di-substituted benzene a convenient bio-assay using drosophila larvae. ring protons, respectively. The double The assay is of great advantage to judge easily resonance experiment clarified that the protons the effects of compounds on the growth of the at ƒÂ 3.26 coupled with both the proton at ƒÂ insects at each stage from the larvae to the 5.7•`6.2 (with J=7Hz) and protons at ƒÂ 4.9•` adults. In the screening of plant extracts by this method, we found that the methanol ex tract of the leaves of Viburnum japonicum Spreng. inhibited remarkably the growth of the larvae. We report here the isolation, identification of the active component of V. japonicum, and also report the activities of the component and the related compounds against the adults as well as the larvae. An ethyl acetate-soluble part of the methanol extract was chromatographed on silicic acid- Celite 545 eluted with benzene of an increasing ratio of ethyl acetate. The larva-killing activi ty was found in a fraction eluted with 5% ethyl acetate in benzene. -
RIFM Fragrance Ingredient Safety Assessment, Anisyl Alcohol, CAS Registry T Number 105-13-5 A.M
Food and Chemical Toxicology 134 (2019) 110702 Contents lists available at ScienceDirect Food and Chemical Toxicology journal homepage: www.elsevier.com/locate/foodchemtox Short Review RIFM fragrance ingredient safety assessment, anisyl alcohol, CAS registry T number 105-13-5 A.M. Apia, D. Belsitob, S. Bisertaa, D. Botelhoa, M. Bruzec, G.A. Burton Jr.d, J. Buschmanne, M.A. Cancellieria, M.L. Daglif, M. Datea, W. Dekantg, C. Deodhara, A.D. Fryerh, S. Gadhiaa, L. Jonesa, K. Joshia, A. Lapczynskia, M. Lavellea, D.C. Liebleri, M. Naa, D. O'Briena, A. Patela, T.M. Penningj, G. Ritaccoa, F. Rodriguez-Roperoa, J. Rominea, N. Sadekara, D. Salvitoa, ∗ T.W. Schultzk, F. Siddiqia, I.G. Sipesl, G. Sullivana, , Y. Thakkara, Y. Tokuram, S. Tsanga a Research Institute for Fragrance Materials, Inc., 50 Tice Boulevard, Woodcliff Lake, NJ, 07677, USA b Member Expert Panel, Columbia University Medical Center, Department of Dermatology, 161 Fort Washington Ave., New York, NY, 10032, USA c Member Expert Panel, Malmo University Hospital, Department of Occupational & Environmental Dermatology, Sodra Forstadsgatan 101, Entrance 47, Malmo SE, 20502, Sweden d Member Expert Panel, School of Natural Resources & Environment, University of Michigan, Dana Building G110, 440 Church St., Ann Arbor, MI, 58109, USA e Member Expert Panel, Fraunhofer Institute for Toxicology and Experimental Medicine, Nikolai-Fuchs-Strasse 1, 30625, Hannover, Germany f Member Expert Panel, University of Sao Paulo, School of Veterinary Medicine and Animal Science, Department of Pathology, Av. Prof. dr. Orlando Marques de Paiva, 87, Sao Paulo, CEP 05508-900, Brazil g Member Expert Panel, University of Wuerzburg, Department of Toxicology, Versbacher Str. -
Piper Betle (L): Recent Review of Antibacterial and Antifungal Properties, Safety Profiles, and Commercial Applications
molecules Review Piper betle (L): Recent Review of Antibacterial and Antifungal Properties, Safety Profiles, and Commercial Applications Ni Made Dwi Mara Widyani Nayaka 1,* , Maria Malida Vernandes Sasadara 1 , Dwi Arymbhi Sanjaya 1 , Putu Era Sandhi Kusuma Yuda 1 , Ni Luh Kade Arman Anita Dewi 1 , Erna Cahyaningsih 1 and Rika Hartati 2 1 Department of Natural Medicine, Mahasaraswati University of Denpasar, Denpasar 80233, Indonesia; [email protected] (M.M.V.S.); [email protected] or [email protected] (D.A.S.); [email protected] (P.E.S.K.Y.); [email protected] (N.L.K.A.A.D.); [email protected] or [email protected] (E.C.) 2 Pharmaceutical Biology Department, Bandung Institute of Technology, Bandung 40132, Indonesia; [email protected] * Correspondence: [email protected] or [email protected] Abstract: Piper betle (L) is a popular medicinal plant in Asia. Plant leaves have been used as a tradi- tional medicine to treat various health conditions. It is highly abundant and inexpensive, therefore promoting further research and industrialization development, including in the food and pharma- ceutical industries. Articles published from 2010 to 2020 were reviewed in detail to show recent updates on the antibacterial and antifungal properties of betel leaves. This current review showed that betel leaves extract, essential oil, preparations, and isolates could inhibit microbial growth and kill various Gram-negative and Gram-positive bacteria as well as fungal species, including those that Citation: Nayaka, N.M.D.M.W.; are multidrug-resistant and cause serious infectious diseases. P. betle leaves displayed high efficiency Sasadara, M.M.V.; Sanjaya, D.A.; on Gram-negative bacteria such as Escherichia coli and Pseudomonas aeruginosa, Gram-positive bacteria Yuda, P.E.S.K.; Dewi, N.L.K.A.A.; such as Staphylococcus aureus, and Candida albicans. -
Methyl Eugenol: Its Occurrence, Distribution, and Role in Nature, Especially in Relation to Insect Behavior and Pollination
Journal of Insect Science: Vol. 12 | Article 56 Tan and Nishida Methyl eugenol: Its occurrence, distribution, and role in nature, especially in relation to insect behavior and pollination Keng Hong Tan1a* and Ritsuo Nishida2b 1Tan Hak Heng, 20, Jalan Tan Jit Seng, 11200 Penang, Malaysia 2Laboratory of Chemical Ecology, Graduate School of Agriculture, Kyoto University, Kyoto, 606-8502, Japan Abstract This review discusses the occurrence and distribution (within a plant) of methyl eugenol in different plant species (> 450) from 80 families spanning many plant orders, as well as various roles this chemical plays in nature, especially in the interactions between tephritid fruit flies and plants. Keywords: allomone, attractant, Bactrocera, chemical ecology, floral fragrance, insect pollinators, plant–insect interactions, plant semiochemicals, sex pheromone, synomone, tephritid fruit flies Abbreviations: ME, methyl eugenol; RK, raspberry ketone Correspondence: a [email protected], b [email protected], *Corresponding author Editor: Todd Shelly was editor of this paper. Received: 28 April 2011, Accepted: 27 August 2011 Copyright : This is an open access paper. We use the Creative Commons Attribution 3.0 license that permits unrestricted use, provided that the paper is properly attributed. ISSN: 1536-2442 | Vol. 12, Number 56 Cite this paper as: Tan KH, Nishida R. 2012. Methyl eugenol: Its occurrence, distribution, and role in nature, especially in relation to insect behavior and pollination. Journal of Insect Science 12:56 available online: insectscience.org/12.56 Journal of Insect Science | www.insectscience.org 1 Journal of Insect Science: Vol. 12 | Article 56 Tan and Nishida 1. Introduction ME has been successfully used in: a) fruit fly surveys (Tan and Lee 1982) and quarantine Plants produce a huge array of chemicals, detection (see reviews by Metcalf and Metcalf numbering tens of thousands, primarily for 1992; Vargas et al. -
Ab Initio Chemical Safety Assessment
Ab initio chemical safety assessment : A workflow based on exposure considerations and non-animal methods Elisabet Berggren, Andrew White, Gladys Ouedraogo, Alicia Paini, Andrea-Nicole Richarz, Frédéric Y. Bois, Thomas Exner, Sofia Batista Leite, L. van Grunsven, Andrew P. Worth, et al. To cite this version: Elisabet Berggren, Andrew White, Gladys Ouedraogo, Alicia Paini, Andrea-Nicole Richarz, et al.. Ab initio chemical safety assessment : A workflow based on exposure considerations and non-animal meth- ods. Computational Toxicology, 2017, 4, pp.31-44. 10.1016/j.comtox.2017.10.001. ineris-01863939 HAL Id: ineris-01863939 https://hal-ineris.archives-ouvertes.fr/ineris-01863939 Submitted on 29 Aug 2018 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. Computational Toxicology 4 (2017) 31–44 Contents lists available at ScienceDirect Computational Toxicology journal homepage: www.elsevier.com/locate/comtox Ab initio chemical safety assessment: A workflow based on exposure MARK considerations and non-animal methods ⁎ Elisabet Berggrena, , Andrew Whiteb, -
(Myristica Fragrans Houtt) at Differ
Journal of Pharmacognosy and Phytochemistry 2016; 5(6): 371-376 E-ISSN: 2278-4136 Physical characterization and essential oil properties of P-ISSN: 2349-8234 JPP 2016; 5(6): 371-376 West Sumatra mace and nutmeg seed (Myristica Received: 09-09-2016 Accepted: 10-10-2016 fragrans Houtt) at different ages at harvest Mimbar Ari Saputro PT. Indesso Aroma, Jl.Alternatif Mimbar Ari Saputro, Nuri Andarwulan and Didah Nur Faridah Cibubur, KM. 9, Cileungsi, West Java, Indonesia Abstract Nuri Andarwulan Myristica fragrans Houtt) is the most important species for spice and nutmeg oil in international trade. (a) Department of Food Science The raw materials in nutmeg oil production consist of mace, young seed, medium seed, and old seed. The and Technology, Faculty of nutmeg seed was classified according to the harvesting age. The physical properties of nutmeg mace and Agricultural Engineering and seeds were determined at different moisture content of samples. The mean length and width of seeds Technology, Bogor Agricultural were (1.45, 1.56, and 2.34 cm) and (1.02, 1.77, and 2.02 cm), respectively. The mean weight of seeds University, Darmaga Campus were 0.77, 1.67, and 2.71 gram. The percentages of oil yield were 19.51, 8.91, 6.35, and 5.04, IPB, Bogor, Indonesia respectively. The mean of specific gravity, refractive index and optical rotation of oils were (0.919, (b) Southeast Asia Food and o o o o Agricultural Science and 0.902, 0.923, and 0.930), (1.487, 1.481, 1,486, and 1.487), and (+6.07 , +7.51 , +6.61 , and +6.58 ), Technology Center, Jl. -
Distribution of Trans-Anethole and Estragole in Fennel (Foeniculum
Available online at www.notulaebiologicae.ro Print ISSN 2067-3205; Electronic 2067-3264 Notulae Scientia Biologicae Not Sci Biol, 2011, 3(1):79-86 Distribution of Trans-Anethole and Estragole in Fennel (Foeniculum vulgare Mill) of Callus Induced from Different Seedling Parts and Fruits Abd El-Moneim Mohamed Radwan AFIFY1 , Hossam Saad EL-BELTAGI1 , Anwer Abd El-aziz HAMMAMA1 , Mahassen Mohamed SIDKY2 , Omneya Farouk Ahmed MOSTAFA2 1Cairo University, Faculty of Agriculture, Department of Biochemistry, P. Box 12613, Gamma st, Giza, Cairo- Egypt; [email protected] 2Horticulture Research Institute, ARC, Giza, Egypt Abstract In the present study, seeds from local cultivar of fennel were germinated on Murashige and Skoog medium (MS) without plant growth regulators. Different types of explants from the growing seedling such as cotyledonal leaves, hypocotyls, epicotyls and roots were cultured on MS medium, contained different concentrations of 2,4-dichlorophenoxyacetic acid (2,4-D) either alone or with kinetin. Differential responses in the essential oil constituents were observed in the induction and development of callus. The major components of essential oils includes estragole, trans-anethole, limonene and fenchone were studied under different conditions to find out the best methods which could be used to reduce the amount of estragole (not favorite for human consumption) and increase the amount of trans-anethole. Keywords: 2,4-dichlorophenoxyacetic acid (2, 4-D), estragole, fennel, Foeniculum vulgare, kinetin, trans-anethole Introduction essential oil of bitter fennel fruits (Bernath et al., 1996; Fennel is a plant belonging to the Umbelliferae (Api- Venskutonis et al., 1996). These, along with some other aceae) family, known and used by humans since antiquity. -
Assessment of Antimicrobial Activity, Mode of Action and Volatile Compounds of Etlingera Pavieana Essential Oil
molecules Article Assessment of Antimicrobial Activity, Mode of Action and Volatile Compounds of Etlingera pavieana Essential Oil Porawan Naksang 1 , Sasitorn Tongchitpakdee 1, Kanjana Thumanu 2, Maria Jose Oruna-Concha 3, Keshavan Niranjan 3 and Chitsiri Rachtanapun 1,4,* 1 Department of Food Science and Technology, Faculty of Agro-Industry, Kasetsart University, Bangkok 10900, Thailand; [email protected] (P.N.); [email protected] (S.T.) 2 Synchrotron Light Research Institute (Public Organization), Nakhon Ratchasima 30000, Thailand; [email protected] 3 Department of Food and Nutritional Sciences, University of Reading, Whiteknights, Reading RG6 6AP, UK; [email protected] (M.J.O.-C.); [email protected] (K.N.) 4 Center for Advanced Studied Agriculture and Food, Kasetsart University, Bangkok 10900, Thailand * Correspondence: [email protected]; Tel.: +66-2562-5000 (ext. 5206) Academic Editors: Francesca Mancianti and Satyajit Sarker Received: 25 May 2020; Accepted: 13 July 2020; Published: 16 July 2020 Abstract: Etlingera pavieana (Pierre ex Gagnep.) R.M.S. is a rhizomatous plant in the Zingiberaceae family which could be freshly eaten, used as a condiment or as a traditional remedy. Our work investigated the chemical composition and antimicrobial activity of the E. pavieana essential oils extracted from the rhizome (EOEP). We extracted the EOEP from the rhizome by hydrodistillation and analyzed the chemical composition by headspace solid-phase microextraction coupled with gas chromatography/mass spectrometry (HS-SPME-GC/MS). A total of 22 volatile compounds were identified where trans-anethole (78.54%) and estragole (19.36%) were the major components in the EOEP. -
Betel-Like-Scented Piper Plants As Diverse Sources of Industrial and Medicinal Aromatic Chemicals
Chiang Mai J. Sci. 2014; 41(5.1) 1171 Chiang Mai J. Sci. 2014; 41(5.1) : 1171-1181 http://epg.science.cmu.ac.th/ejournal/ Contributed Paper Betel-like-scented Piper Plants as Diverse Sources of Industrial and Medicinal Aromatic Chemicals Arisa Sanubol [a], Arunrat Chaveerach*[a], Runglawan Sudmoon [a], Tawatchai Tanee [b], Kowit Noikotr [c] and Chattong Chuachan [d] [a] Department of Biology, Faculty of Science, Khon Kaen University, Khon Kaen 40002, Thailand. [b] Faculty of Environment and Resource Studies, Mahasarakham University, Mahasarakham 44000, Thailand. [c] Department of Biology, Faculty of Science, Ramkhamhaeng University, Bangkok 10240, Thailand. [d] Garden and Development Department, Queen Sirikit Botanic Garden, The Botanical Garden Organization, Chiang Mai 50180, Thailand. *Author for correspondence; e-mail: [email protected] Received: 21 May 2013 Accepted: 10 August 2013 ABSTRACT Piper betle (Piperaceae) or betel leaf, known locally as “Phlu” has been used by people in Thailand for chewing for a long time. Additionally, the leaves are used for traditional remedies and folk customs, such as for weddings and housewarming ceremonies. More recently, the aromatic oil industry has used the leaves for oil distillation. Moreover, the oils are used in several household products. Over the past 12 years of our research on Piper species, we found that among the more than 43 species recorded, there are some plants other than P. betle that possess a betel-like scent, viz. P. betloides, P. crocatum, P. maculaphyllum, P. rubroglandulosum, P. semiimmersum, P. submultinerve, P. tricolor, and P. yinkiangense. As it was expected that these plants would contain similar useful chemicals, their extracts were screened for the chemical contents by GC-MS. -
Eugenol and Isoeugenol, Characteristic Aromatic Constituents of Spices, Are Biosynthesized Via Reduction of a Coniferyl Alcohol Ester
Eugenol and isoeugenol, characteristic aromatic constituents of spices, are biosynthesized via reduction of a coniferyl alcohol ester Takao Koeduka*†, Eyal Fridman*†‡, David R. Gang†§, Daniel G. Vassa˜ o¶, Brenda L. Jackson§, Christine M. Kishʈ, Irina Orlovaʈ, Snejina M. Spassova**, Norman G. Lewis¶, Joseph P. Noel**, Thomas J. Baiga**, Natalia Dudarevaʈ, and Eran Pichersky*†† *Department of Molecular, Cellular, and Developmental Biology, University of Michigan, 830 North University Street, Ann Arbor, MI 48109-1048; §Department of Plant Sciences and Institute for Biomedical Science and Biotechnology, University of Arizona, Tucson, AZ 85721-0036; ¶Institute of Biological Chemistry, Washington State University, Pullman, WA 99164-6340; ʈDepartment of Horticulture and Landscape Architecture, Purdue University, West Lafayette, IN 47907; and **Howard Hughes Medical Institute, Jack H. Skirball Chemical Biology and Proteomics Laboratory, The Salk Institute for Biological Studies, 10010 North Torrey Pines Road, La Jolla, CA 92037 Communicated by Anthony R. Cashmore, University of Pennsylvania, Philadelphia, PA, May 5, 2006 (received for review March 31, 2006) Phenylpropenes such as chavicol, t-anol, eugenol, and isoeugenol are produced by plants as defense compounds against animals and microorganisms and as floral attractants of pollinators. Moreover, humans have used phenylpropenes since antiquity for food pres- ervation and flavoring and as medicinal agents. Previous research suggested that the phenylpropenes are synthesized in plants from substituted phenylpropenols, although the identity of the en- zymes and the nature of the reaction mechanism involved in this transformation have remained obscure. We show here that glan- dular trichomes of sweet basil (Ocimum basilicum), which synthe- size and accumulate phenylpropenes, possess an enzyme that can use coniferyl acetate and NADPH to form eugenol.