GAS CHROMATOGRAPHY – BIOCHEMICALS, NARCOTICS AND ESSENTIAL OILS Edited by Bekir Salih and Ömür Çelikbıçak Gas Chromatography – Biochemicals, Narcotics and Essential Oils Edited by Bekir Salih and Ömür Çelikbıçak Published by InTech Janeza Trdine 9, 51000 Rijeka, Croatia Copyright © 2012 InTech All chapters are Open Access distributed under the Creative Commons Attribution 3.0 license, which allows users to download, copy and build upon published articles even for commercial purposes, as long as the author and publisher are properly credited, which ensures maximum dissemination and a wider impact of our publications. After this work has been published by InTech, authors have the right to republish it, in whole or part, in any publication of which they are the author, and to make other personal use of the work. Any republication, referencing or personal use of the work must explicitly identify the original source. As for readers, this license allows users to download, copy and build upon published chapters even for commercial purposes, as long as the author and publisher are properly credited, which ensures maximum dissemination and a wider impact of our publications. Notice Statements and opinions expressed in the chapters are these of the individual contributors and not necessarily those of the editors or publisher. No responsibility is accepted for the accuracy of information contained in the published chapters. The publisher assumes no responsibility for any damage or injury to persons or property arising out of the use of any materials, instructions, methods or ideas contained in the book. Publishing Process Manager Daria Nahtigal Technical Editor Teodora Smiljanic Cover Designer InTech Design Team First published March, 2012 Printed in Croatia A free online edition of this book is available at www.intechopen.com Additional hard copies can be obtained from orders@intechweb.org Gas Chromatography – Biochemicals, Narcotics and Essential Oils, Edited by Bekir Salih and Ömür Çelikbıçak p. cm. ISBN 978-953-51-0295-3 Contents Preface IX Part 1 Biochemical Applications 1 Chapter 1 Gas Chromatography in Environmental Sciences and Evaluation of Bioremediation 3 Vladimir P. Beškoski, Gordana Gojgić-Cvijović, Branimir Jovančićević and Miroslav M. Vrvić Chapter 2 Comprehensive Two-Dimensional Gas Chromatography Coupled to Time-of-Flight Mass Spectrometry in Human Metabolomics 29 Petr Wojtowicz, Jitka Zrostlíková, Veronika Šťastná, Eva Dostálová, Lenka Žídková, Per Bruheim and Tomáš Adam Chapter 3 Urinary Olfactory Chemosignals in Lactating Females Show More Attractness to Male Root Voles (Microtus oeconomus) 51 Ping Sun, Xiangchao Cheng and Honghao Yu Chapter 4 Gas Chromathography as a Tool in Quorum Sensing Studies 67 Oscar Osorno, Leonardo Castellanos, Freddy A. Ramos and Catalina Arévalo‐Ferro Chapter 5 Application of Gas Chromatography in a Study of Marine Biogeochemistry 97 Luisa-Fernanda Espinosa, Silvio Pantoja and Jürgen Rullkötter Chapter 6 Fatty Acids Analysis of Photosynthetic Sulfur Bacteria by Gas Chromatography 117 María Teresa Núñez-Cardona Chapter 7 Gas Chromatography Results Interpretation: Absolute Amounts Versus Relative Percentages 139 G.M. Hon, S. Abel, C.M. Smuts, P. van Jaarsveld, M.S. Hassan, S.J. van Rensburg, R.T. Erasmus and T. Matsha VI Contents Part 2 Narcotics 161 Chapter 8 Chromatographic Methodologies for Analysis of Cocaine and Its Metabolites in Biological Matrices 163 Maria João Valente, Félix Carvalho, Maria de Lourdes Bastos, Márcia Carvalho and Paula Guedes de Pinho Chapter 9 Gas Chromatography in Forensic Chemistry: Cannabinoids Content in Marijuana Leaves (Cannabis sativa L.) from Colombia 195 N.M. Florian-Ramírez, W.F. Garzón-Méndez and F. Parada-Alfonso Part 3 Essential Oils 211 Chapter 10 Chemical Composition, Antioxidant and Antimicrobial Activities of Essential Oil of Warionia saharae from Oases of Morocco 213 K. Sellam, M. Ramchoun, C. Alem, Farid Khallouki B. El Moualij and L. El Rhaffari Chapter 11 Development and Validation of Analytical Methodology and Evaluation of the Impact of Culture Conditions and Collection Associated with the Seasonality in the Production of Essential Oil of Plectranthus amboinicus (Lour) Spreng 221 Fabíola B. Carneiro, Irinaldo D. Júnior, Pablo Q. Lopes and Rui O. Macêdo Preface Chromatography was gained more importance initially after discovered in the preparative chromatography using large amount of the sample for the separation all components properly and collect each in their pure forms. Recently analytical chromatography found many application areas. The purpose of preparative Analytical chromatography is done normally with smaller amounts of material and is for measuring the relative proportions of analytes in a mixture after discovered some detectors which need very low amount of the analyte and have proper detection limits. In the late 2000, the really beneficial form of the gas chromatography called Two Dimensional Gas Chromatography (GCXGC) started to use for the different groups having different polarity of the volatile compounds under the gas chromatographic conditions in one batch. In this way, application area of Gas Chromatography expanded incredible extent. However, To parallel to the development of the new Gas Chromatographic techniques, development of new column material and production of capillary column in different long filled with viscous uniform liquid stationary phase using high technologies were supplied high chromatographic efficiency for the proper separation, and accurate and precise quantification of each compound in a mixture consist of thousands and thousands different components. The development of the chromatography showed enormous race and many sophisticated chromatographic methods were discovered for different analytes related to their volatility, molecular weight, and hydrophobicity, the specificity to the phases or functional groups of the phases used in the chromatographic techniques. In the past, mainly preparative chromatographic techniques were used but nowadays miniaturized and modern systems which required very low volume of samples such as nano liters and low concentration of the analytes from part per trillion (ppt) to part per million (ppm) are prominently important. To parallel to the development, new detection systems were also discovered in order to measure the analytes in the very low volume and with the most desired detection limits. At the academic side, many researchers know how they find their way to touch suitable method and useful chromatographic techniques to analyze their samples with high accuracy and precision by the proper chromatographic technique and its required X Preface tools such as column, phases and detectors. Nevertheless, the people who are working at the industry ask very sophisticated question about the real sample “which compounds and in which level of their concentrations are in the samples?”. To answer this question, there is no way to go out not to touch the chromatographic techniques. The one most useful chromatographic technique is the Gas Chromatography for the volatile compounds, both organic and organometallic which having volatility up to 300 o C. However, some of non-volatile compounds up to 300 o C could be derivatized and could be increase the volatility and make possible to analyze these compounds in Gas Chromatography. Using capillary column, two dimensional Gas Chromatography and some convenient detectors, around hundreds of compounds could be analyzed quantitatively and qualitatively in the same run. Today, hyphenated methods including Gas Chromatography-Mass Spectrometry (GC- MS) and Gas Chromatography-Atomic Spectrometry have been widely used for the detection and quantification of the organic molecules and also organometallic species. Especially Gas Chromatography-Mass spectrometry technique is the best for the identification of the finger prints of the organic molecules and their quantification at trace levels. This hyphenated technique does not need any reference material to identify the organic and organometallic species using chromatographic separation and mass spectrometric detection. Therefore, GC-MS system is a kind of most special and useful system among the other Gas Chromatographic Systems. After all these developments in Gas Chromatography and its hyphenated methods, these techniques have been finding many applications in various sample analysis in different real samples such as environmental, biological, foods, drugs, narcotics, plants, soils, sediments and the other samples. Using the information in the chapters, it may be possible to develop Gas Chromatographic procedures for different compounds in narcotics, metabolites of some drugs and the organic compounds, essential oils and their derivatized forms and the antioxidants by the readers of the book. Dr. Bekir Salih and Dr. Ömür Çelikbıçak Hacettepe University Department of Chemistry Ankara Turkey . GAS CHROMATOGRAPHY – BIOCHEMICALS, NARCOTICS AND ESSENTIAL OILS Edited by Bekir Salih and Ömür Çelikbıçak Gas Chromatography – Biochemicals, Narcotics and Essential. dispersion and water–oil emulsification, photooxidation, adsorption onto suspended Gas Chromatography – Biochemicals, Narcotics and Essential Oils 4 particulate materials, and oil–mineral. methods have high selectivity and compounds can be authenticated by Gas Chromatography – Biochemicals, Narcotics and Essential Oils 6 analysing retention times and unique mass spectra. GC-MS