Monoterpenes in the Glandular Trichomes of Tomato Are Synthesized
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Molecular Regulation of Plant Monoterpene Biosynthesis in Relation to Fragrance
Molecular Regulation of Plant Monoterpene Biosynthesis In Relation To Fragrance Mazen K. El Tamer Promotor: Prof. Dr. A.G.J Voragen, hoogleraar in de Levensmiddelenchemie, Wageningen Universiteit Co-promotoren: Dr. ir. H.J Bouwmeester, senior onderzoeker, Business Unit Celcybernetica, Plant Research International Dr. ir. J.P Roozen, departement Agrotechnologie en Voedingswetenschappen, Wageningen Universiteit Promotiecommissie: Dr. M.C.R Franssen, Wageningen Universiteit Prof. Dr. J.H.A Kroeze, Wageningen Universiteit Prof. Dr. A.J van Tunen, Swammerdam Institute for Life Sciences, Universiteit van Amsterdam. Prof. Dr. R.G.F Visser, Wageningen Universiteit Mazen K. El Tamer Molecular Regulation Of Plant Monoterpene Biosynthesis In Relation To Fragrance Proefschrift ter verkrijging van de graad van doctor op gezag van de rector magnificus van Wageningen Universiteit, Prof. dr. ir. L. Speelman, in het openbaar te verdedigen op woensdag 27 november 2002 des namiddags te vier uur in de Aula Mazen K. El Tamer Molecular Regulation Of Plant Monoterpene Biosynthesis In Relation To Fragrance Proefschrift Wageningen Universiteit ISBN 90-5808-752-2 Cover and Invitation Design: Zeina K. El Tamer This thesis is dedicated to my Family & Friends Contents Abbreviations Chapter 1 General introduction and scope of the thesis 1 Chapter 2 Monoterpene biosynthesis in lemon (Citrus limon) cDNA isolation 21 and functional analysis of four monoterpene synthases Chapter 3 Domain swapping of Citrus limon monoterpene synthases: Impact 57 on enzymatic activity and -
Review Article a Review on Anti-Oxidative Herbs PL
INTERNATIONAL JOURNAL OF PHARMACEUTICAL AND CHEMICAL SCIENCES ISSN: 22775005 Review Article A Review on Anti-oxidative Herbs PL. Rajagopal1*, VB. Narayana Swamy2, SS. Kiron3 and KR. Sreejith4 1Department of Pharmacognosy, Academy of Pharmaceutical Sciences, Pariyaram Medical College, Kannur, Kerala, South India. 2Professor and Principal, Department of Pharmacognosy, Karaveli College of Pharmacy, Mangalore, Karnataka, South India. 3Department of Pharmacy Practice, Academy of Pharmaceutical Sciences, Pariyaram Medical College, Kannur, Kerala, South India. 4Department of Pharmaceutical Chemistry, Academy of Pharmaceutical Sciences, Pariyaram Medical College, Kannur, Kerala, South India. ABSTRACT Plants are valuable source of the therapeutic agents in the armory of modern medicine. The method of drug development from plant sources is based on a sequence of operation leading mainly toward the isolation of pure natural products. An antioxidant is a molecule that inhibits the oxidation of other molecules. Antioxidants have been investigated for the prevention of diseases such as cancer, coronary heart disease and even altitude sickness. The major sources of anti-oxidants are reported to be from the natural source, especially from plant source. Key words: Anti oxidant, Free radical, Medicinal Plants INTRODUCTION pharmacological studies to ascertain their Till date as such no set definition of the term therapeutic properties. (Bakru H.K. 1992). antioxidant exists. Scientists are still striving In this review an attempt has been made o hard to find out the role of particular dietary compile most of the Natural Herbs which supplements in body that have potent health possess ant oxidative property. Following are benefits. Since, different antioxidant the list of such medicinal herbs which are compounds found in diet considerably vary reported to be an antioxidant. -
Biosynthesis of Natural Products
63 2. Biosynthesis of Natural Products - Terpene Biosynthesis 2.1 Introduction Terpenes are a large and varied class of natural products, produced primarily by a wide variety of plants, insects, microoroganisms and animals. They are the major components of resin, and of turpentine produced from resin. The name "terpene" is derived from the word "turpentine". Terpenes are major biosynthetic building blocks within nearly every living creature. Steroids, for example, are derivatives of the triterpene squalene. When terpenes are modified, such as by oxidation or rearrangement of the carbon skeleton, the resulting compounds are generally referred to as terpenoids. Some authors will use the term terpene to include all terpenoids. Terpenoids are also known as Isoprenoids. Terpenes and terpenoids are the primary constituents of the essential oils of many types of plants and flowers. Essential oils are used widely as natural flavor additives for food, as fragrances in perfumery, and in traditional and alternative medicines such as aromatherapy. Synthetic variations and derivatives of natural terpenes and terpenoids also greatly expand the variety of aromas used in perfumery and flavors used in food additives. Recent estimates suggest that over 30'000 different terpenes have been characterized from natural sources. Early on it was recognized that the majority of terpenoid natural products contain a multiple of 5C-atoms. Hemiterpenes consist of a single isoprene unit, whereas the monoterpenes include e.g.: Monoterpenes CH2OH CHO CH2OH OH Myrcens -
Use the Right Citrus-Based Cleaning Products to Avoid Corrosion Or Rust Bob Beckley, Project Leader
United States Department of Agriculture Facilities Forest Service Technology & Development Program March 2006 0673–2319–MTDC 7300/7100/5100/2400/2300 Use the Right Citrus-Based Cleaning Products to Avoid Corrosion or Rust Bob Beckley, Project Leader itrus-based cleaning products are commonly found in metal on their chain saws. The crew stopped using citrus-based residential and commercial settings. The ingredients in products because they believed citric acid was causing the these products vary widely (figure 1). While some of damage. However, the damage probably was caused by a C water-based citrus cleaning product. What To Look for in a Citrus-Based Cleaning Product The Material Safety Data Sheets (MSDSs) for chemical products list their ingredients. The MSDS for a citrus-based cleaner should list D-Limonene among the ingredients. D- Limonene is in the terpene family, which includes citrus and pine oils. Terpenes are generally not corrosive or harmful to metals or most plastics and polymers. Terpenes won’t cause rusting, pitting, etching, or staining. Citrus-based terpenes can dissolve heavy petroleum greases and residues in about 30 Figure 1—Citrus-based cleaners are commonly used in residential and minutes when they are used at ambient temperatures. commercial settings, but users often are unaware of the difference between citrus oil-based cleaning products and water-based products. A citrus oil-based cleaning product will not cause corrosion these products can cause corrosion or rust, others do not. The or rust. Such products are made from the oil found in the difference is based on the ingredients. Hundreds of cleaning orange peel, rather than the pulp and juice of the orange. -
(C5–C20) Emissions of Downy Birches
Atmos. Chem. Phys., 21, 8045–8066, 2021 https://doi.org/10.5194/acp-21-8045-2021 © Author(s) 2021. This work is distributed under the Creative Commons Attribution 4.0 License. Sesquiterpenes and oxygenated sesquiterpenes dominate the VOC (C5–C20) emissions of downy birches Heidi Hellén1, Arnaud P. Praplan1, Toni Tykkä1, Aku Helin1, Simon Schallhart1, Piia P. Schiestl-Aalto2,3,4, Jaana Bäck2,3, and Hannele Hakola1 1Atmospheric Composition Research Unit, Finnish Meteorological Institute, P.O. Box 503, 00101 Helsinki, Finland 2Institute for Atmospheric and Earth System Research/Forest Sciences, Helsinki, Finland 3Faculty of Agriculture and Forestry, University of Helsinki, Helsinki, Finland 4Department of Forest Ecology and Management, SLU, 901 83 Umeå, Sweden Correspondence: Heidi Hellén (heidi.hellen@fmi.fi) Received: 2 December 2020 – Discussion started: 16 December 2020 Revised: 23 March 2021 – Accepted: 28 April 2021 – Published: 26 May 2021 Abstract. Biogenic volatile organic compounds (BVOCs) 24 % and 17 % of the total SQT and OSQT emissions, re- emitted by the forests are known to have strong impacts in spectively. A stressed tree growing in a pot was also stud- the atmosphere. However, lots of missing reactivity is found, ied, and high emissions of α-farnesene and an unidentified especially in the forest air. Therefore better characterization SQT were detected together with high emissions of GLVs. of sources and identification/quantification of unknown re- Due to the relatively low volatility and the high reactivity of active compounds is needed. While isoprene and monoter- SQTs and OSQTs, downy birch emissions are expected to pene (MT) emissions of boreal needle trees have been studied have strong impacts on atmospheric chemistry, especially on quite intensively, there is much less knowledge on the emis- secondary organic aerosol (SOA) production. -
Medically Useful Plant Terpenoids: Biosynthesis, Occurrence, and Mechanism of Action
molecules Review Medically Useful Plant Terpenoids: Biosynthesis, Occurrence, and Mechanism of Action Matthew E. Bergman 1 , Benjamin Davis 1 and Michael A. Phillips 1,2,* 1 Department of Cellular and Systems Biology, University of Toronto, Toronto, ON M5S 3G5, Canada; [email protected] (M.E.B.); [email protected] (B.D.) 2 Department of Biology, University of Toronto–Mississauga, Mississauga, ON L5L 1C6, Canada * Correspondence: [email protected]; Tel.: +1-905-569-4848 Academic Editors: Ewa Swiezewska, Liliana Surmacz and Bernhard Loll Received: 3 October 2019; Accepted: 30 October 2019; Published: 1 November 2019 Abstract: Specialized plant terpenoids have found fortuitous uses in medicine due to their evolutionary and biochemical selection for biological activity in animals. However, these highly functionalized natural products are produced through complex biosynthetic pathways for which we have a complete understanding in only a few cases. Here we review some of the most effective and promising plant terpenoids that are currently used in medicine and medical research and provide updates on their biosynthesis, natural occurrence, and mechanism of action in the body. This includes pharmacologically useful plastidic terpenoids such as p-menthane monoterpenoids, cannabinoids, paclitaxel (taxol®), and ingenol mebutate which are derived from the 2-C-methyl-d-erythritol-4-phosphate (MEP) pathway, as well as cytosolic terpenoids such as thapsigargin and artemisinin produced through the mevalonate (MVA) pathway. We further provide a review of the MEP and MVA precursor pathways which supply the carbon skeletons for the downstream transformations yielding these medically significant natural products. Keywords: isoprenoids; plant natural products; terpenoid biosynthesis; medicinal plants; terpene synthases; cytochrome P450s 1. -
A Terpene for Everyone Maximizing Your Cannabis Experience Author: Caitlin Nelson | Editors: Erica Freeman & Amanda Woods
A Terpene for Everyone Maximizing your Cannabis Experience Author: Caitlin Nelson | Editors: Erica Freeman & Amanda Woods Let’s take a moment to re-hash our topic—terpenes! The essential oils that create the familiar scent that fills your nose when you open your jar of Sour Diesel, and maybe even makes your mouth water. (Just a little, not drooling status or anything) The compounds are inhaled through the nose, and transported to the hypothalamus in the limbic brain, which controls heart rate, blood pressure, hunger, and thirst. Terpene test results are broken down by each terpene as a percentage of the total terpene profile (i.e., some percentage out of 100%). There are hundreds of terpenes and countless combinations; each combination carrying a unique set of characteristics working to unlock your bodies cannabinoid receptors like a key. An “herban” legend rumors that eating a Mango before smoking cannabis would get you “more high”. This sounds like a delicious myth and current research suggest there is some truth to this after all. It turns out that Mangos contain a high percentage of the compound β-Myrcene, which “…has been shown to allow more absorption of cannabinoids by the brain, by changing the permeability of cell membranes. Eating a fresh mango 45 minutes before smoking could increase the effects”, Steep Hill Lab states. (buys stock in Mangos) β–Myrcene gets its name from a medicinal shrub from Brazil, the Myrcia sphaerocarpa, which contains very high amounts of β–Myrcene. According to many sources, extracts of the roots have been used there to treat hypertension, diabetes, diarrhea and dysentery. -
Leaf and Flower Volatile Oil Components of Two Thyme Taxa Origanum Onites L
Avrupa Bilim ve Teknoloji Dergisi European Journal of Science and Technology Sayı 17, S. 346-350, Aralık 2019 No. 17, pp. 346-350, December 2019 © Telif hakkı EJOSAT’a aittir Copyright © 2019 EJOSAT Araştırma Makalesi www.ejosat.com ISSN:2148-2683 Research Article Leaf and Flower Volatile Oil Components of Two Thyme Taxa Origanum onites L. and Thymbra spicata var. spicata L. in Turkey Ayşe Gül Sarıkaya1* 1 Bursa Technical University, Faculty of Forestry, Bursa-Turkey (ORCID: 0000-0002-0641-4445) (İlk Geliş Tarihi 10 Eylül 2019 ve Kabul Tarihi 14 Ekim 2019) (DOI: 10.31590/ejosat.618187) ATIF/REFERENCE: Sarıkaya, A. (2019). Leaf and Flower Volatile Oil Components of Two Thyme Taxa Origanum onites L. and Thymbra spicata var. spicata L. in Turkey. Avrupa Bilim ve Teknoloji Dergisi, (17), 346-350. Abstract Medicinal and aromatic plants have a special importance with volatile oil components. Lamiaceae family members are important in pharmacology and perfumery industry because they contain volatile and aromatic oil. Origanum onites L. and Thymbra spicata var. spicata L. are the most widely used and most exported species. The volatile components of the leaves and flowers of Origanum onites L. and Thymbra spicata var. spicata taxa were determined by Headspace Solid Phase Microextraction (HS-SPME) technique combined with gas chromatography/mass spectrometry (GC / MS). 33 different components of Origanum onites were identified and the main components were p-cymene (11.45%), γ-terpinene (11.89%), linalool (14.35%), thymol (20.03%) and carvacrol (26.91%), respectively. For Thymbra spicata var. spicata L., 36 different compounds were identified and the main components were p-cymene (11.72%), γ-terpinene (10.96%), linalool (13.44%), thymol (18.92%) and carvacrol (27.34%), respectively. -
Isoprene Rule Revisited 242:2 R9–R22 Endocrinology REVIEW Terpenes, Hormones and Life: Isoprene Rule Revisited
242 2 Journal of S G Hillier and R Lathe Isoprene rule revisited 242:2 R9–R22 Endocrinology REVIEW Terpenes, hormones and life: isoprene rule revisited Stephen G Hillier1 and Richard Lathe2 1Medical Research Council Centre for Reproductive Health, University of Edinburgh, The Queen’s Medical Research Institute, Edinburgh, UK 2Division of Infection and Pathway Medicine, University of Edinburgh Medical School, Edinburgh, UK Correspondence should be addressed to S G Hillier or R Lathe: [email protected] or [email protected] Abstract The year 2019 marks the 80th anniversary of the 1939 Nobel Prize in Chemistry awarded Key Words to Leopold Ruzicka (1887–1976) for work on higher terpene molecular structures, including f isoprene the first chemical synthesis of male sex hormones. Arguably his crowning achievement f terpene was the ‘biogenetic isoprene rule’, which helped to unravel the complexities of terpenoid f steroid biosynthesis. The rule declares terpenoids to be enzymatically cyclized products of f evolution substrate alkene chains containing a characteristic number of linear, head-to-tail f great oxidation event condensed, C5 isoprene units. The number of repeat isoprene units dictates the type of f Ruzicka terpene produced (i.e., 2, monoterpene; 3, sesquiterpene; 4, diterpene, etc.). In the case of triterpenes, six C5 isoprene units combine into C30 squalene, which is cyclized into one of the signature carbon skeletons from which myriad downstream triterpenoid structures are derived, including sterols and steroids. Ruzicka also had a keen interest in the origin of life, but the pivotal role of terpenoids has generally been overshadowed by nucleobases, amino acids, and sugars. -
Camphene, A3-Carene, Limonene, and Ot=Terpinene
Environ. Sci. Technol. 1999, 33,4029-4033 The hydrocarbon emissions are typically divided into two Thermal Degradation of Terpenes: categories: (a) the condensed hydrocarbons of higher molecular weight that are responsible in part for the blue- Camphene, A3-Carene, Limonene, haze plume characteristic of dryer emissions and (b) the and ot=Terpinene lower molecular weight hydrocarbons (C+&), generally referred to as volatile hydrocarbons. Both nongaseous (condensed) and gaseous (volatile) hydrocarbons emitted GERALD W. MCGRAW,*,+ by wood dryers have been analyzed by a number of workers RICHARD W. HEMINGWAY,* LEONARD L. INGRAM, JR.,s (2-s). In general, the nongaseous fraction consists of a CATHERINE S. CANADY,’ AND mixture of resin acids and fatty acids and their esters as well WILLIAM B. MCGRAW+ as some sesquiterpenoid compounds and undefined oxida- tion products. The gaseous fraction is primarily made up of of Chemistry, Louisiana College, monoterpenes present in the wood and some of their Pineuille, Louisiana 71359, Southern Research Station, USDA Forest Service, 2500 Shreveport Highway, oxidation products. Comparatively little is known about the Pineuille, Louisiana 71360, and Forest Products Lab, yields, structures, and biological properties of oxidation Department of Forest Products, Mississippi State University, products of monoterpenes. Mississippi State, Mississippi 39762-9820 Cronn et al. (3) studied the gaseous emissions from a number of veneer dryers at mills in the northwest and southern U.S. From a plywood veneer dryer in the southern U.S. using a mixture of loblolly and shortleaf pines, it was Emissions from wood dryers have been of some concern found that terpenes accounted for 98.9% of the total gaseous for a number of years, and recent policy changes by the hydrocarbon emissions. -
A Genomic Approach to Characterization of the Citrus Terpene Synthase Gene Family
Genetics and Molecular Biology, 30, 3 (suppl), 832-840 (2007) Copyright by the Brazilian Society of Genetics. Printed in Brazil www.sbg.org.br Research Article A genomic approach to characterization of the Citrus terpene synthase gene family Marcelo Carnier Dornelas and Paulo Mazzafera Departamento de Fisiologia Vegetal, Instituto de Biologia, Universidade Estadual de Campinas, Campinas, SP, Brazil. Abstract Terpenes are a very large and structurally diverse group of secondary metabolites which are abundant in many es- sential oils, resins and floral scents. Additionally, some terpenes have roles as phytoalexins in plant-pathogen rela- tionships, allelopathic inhibitors in plant-plant interactions, or as airborne molecules of plant-herbivore multitrophic signaling. Thus the elucidation of the biochemistry and molecular genetics of terpenoid biosynthesis has paramount importance in any crop species. With this aim, we searched the CitEST database for clusters of expressed sequence tags (ESTs) coding for terpene synthases. Herein is a report on the identification and in silico characterization of 49 putative members of the terpene synthase family in diverse Citrus species. The expression patterns and the possible physiological roles of the identified sequences are also discussed. Key words: secondary metabolism, flavor, aroma, plant protection, terpene synthesis. Received: July 21, 2006; Accepted: April 2, 2007. Introduction respectively. Polyterpenes are all terpenes containing more Terpenes are found widely distributed in the plant than eight isoprene units, which include all natural rubbers kingdom, from lichens and algae to higher plants. Although (Goodwin, 1967; Croteau et al., 2000). terpenes cover a wide range of compounds with diverse Elucidation of the biochemistry and molecular genet- structure, the word terpene has been frequently associated ics of terpenoid biosynthesis has made rapid progress in re- with essential oils, which are volatile compounds belong- cent years (Rohdich et al., 2005). -
Terpene Esters from Natural Products: Synthesis and Evaluation of Cytotoxic Activity
Anais da Academia Brasileira de Ciências (2017) 89(3): 1369-1379 (Annals of the Brazilian Academy of Sciences) Printed version ISSN 0001-3765 / Online version ISSN 1678-2690 http://dx.doi.org/10.1590/0001-3765201720160780 www.scielo.br/aabc | www.fb.com/aabcjournal Terpene Esters from Natural Products: Synthesis and Evaluation of Cytotoxic Activity MAURICIO M. VICTOR1,2, JORGE M. DAVID1,2, MARIA C.K. SAKUKUMA1,2, LETÍCIA V. COSTA-LOTUFO3,4, ANDREA F. MOURA3 and ANA J. ARAÚJO3,5 1Instituto de Química, Universidade Federal da Bahia, Depto de Química Orgânica, Rua Barão do Jeremoabo, s/n, Campus de Ondina, Ondina, 40170-115 Salvador, BA, Brazil 2Instituto Nacional de Ciência e Tecnologia/INCT de Energia e Ambiente,Universidade Federal da Bahia/UFBA, Rua Barão de Geremoabo, 147, Campus de Ondina, 40170-290 Salvador, BA, Brazil 3Departamento de Fisiologia e Farmacologia, Universidade Federal do Ceará, Centro de Ciências da Saúde, Av. Coronel Nunes de Melo, 1127, Rodolfo Teófilo, 60430-270 Fortaleza, CE, Brazil 4Departamento de Farmacologia, Universidade de São Paulo, Av. Professor Lineu Prestes, 1524, Cidade Universitária, Butantã, 05508-900 São Paulo, SP, Brazil 5Universidade Federal do Piauí, Av. São Sebastião, 2819, São Benedito, Campus Ministro Reis Velloso, 64202-020 Parnaíba, PB, Brazil Manuscript received on November 16, 2016; accepted for publication on February 22, 2017 ABSTRACT Natural steroids and triterpenes such as β-sitosterol, stigmasterol, lupeol, ursolic and betulinic acids were transformed into its hexanoic and oleic esters, to evaluate the influence of chemical modification towards the cytotoxic activities against tumor cells. The derivatives were evaluated against five tumor cell lines [OVCAR-8 (ovarian carcinoma); SF-295 (glioblastoma); HCT-116 (colon adenocarcinoma); HL-60 (leukemia); and PC-3 (prostate carcinoma)] and the results showed only betulinic acid hexyl ester exhibits cytotoxic potential activity.