Lipids, Lipophilic Components and Essential Oils from Plant Sources
Shakhnoza S. Azimova, Anna I. Glushenkova Editors Lipids, Lipophilic Components and Essential Oils from Plant Sources
Editors Shakhnoza S. Azimova (Ed.) S.Yu. Yunusov Institute of the Chemistry of Plant Substances of the Academy of Sciences of the Anna I. Glushenkova (Co-Editor) S.Yu. Yunusov Institute of the Chemistry of Plant Substances of the Academy of Sciences of the ISBN: 978-0-85729-322-0 e-isbn: 978-0-85729-323-7 DOI: 10.1007/978-0-85729-323-7 ISBN Bundle 978-0-85729-324-4 Springer New York Dordrecht Heidelberg London Library of Congress Control Number: 2011934766 # Springer ScienceþBusiness Media, LLC 2012 All rights reserved. This work may not be translated or copied in whole or in part without the written permission of the publisher (Springer ScienceþBusiness Media, LLC, 233 Spring Street, New York, NY 10013, USA), except for brief excerpts in connection with reviews or scholarly analysis. Use in connection with any form of information storage and retrieval, electronic adaptation, computer software, or by similar or dissimilar methodology now known or hereafter developed is forbidden. The use in this publication of trade names, trademarks, service marks, and similar terms, even if they are not identified as such, is not to be taken as an expression of opinion as to whether or not they are subject to proprietary rights. Printed on acid-free paper Springer is part of Springer ScienceþBusiness Media (www.springer.com)
Preface Lipids and lipophilic components are vital for the functioning of a live organisms. They represent a large group of organic compounds produced by microorganisms, mushrooms, plants, sea organisms, and animals Lipids are fats and fat-like substances, which differ in chemical composition, structure, and by physiological and biochemical function. Lipids are not, or poorly, soluble in water but are soluble in typical solvents: benzine, benzene, chloroform, carbon tetrachloride, acetone, diethyl ether, petroleum ether, and hot alcohols. Lipids are divided into the following categories: 1. Simple lipids: These contain esters of higher fatty acids and some alcohols. This group includes neutral fats, representing esters of fatty acids and glycerine, and waxes. 2. Complex lipids: Their molecules contain, apart from alcohol and fatty acid, derivatives of phosphoric or sulfuric acid, nitrogenous bases, and some saccharides. This group includes phospholipids, cerebrosides, and glycolipids. 3. Other lipids: These are compounds with cyclic structures. This group includes glycerine esters of alicyclic macromolecular acids, alicyclic alcohols or sterols and their esters, and also alcohols, containing cyclic β-ionone, higher hydrocarbons, and others. Lipids are insoluble in water; hence, they are a part of the main structural elements of protoplasm. Lipids and lipid protein complexes provide the building of superficial membranes of cells and cell organs: nucleus, mitochondria, ribosomes et al. Being in the composition of membranes, lipids take part in the process of active transportation of ions and molecules through membranes. Also, neutral lipids are sources of energy. Characteristic components of essential oils are terpenes, which differ from fatty oils, becouse they do not contain glycerides of fatty acids. Some of the essential oils contain saturated and unsaturated aliphatic, aromatic, terpene, sesquiterpene, monoand bicyclic hydrocarbons, and their oxygen derivatives alcohols, aldehydes, ketones, esters, ethers of acids, lactones, and oxides and also heterocyclic compounds. Fatty and essential oils have been known for a long time. In ancient Egypt, plant oils were used not only in food but in medicine, cosmetics, and essential oils in perfumery. Many scientists have taken part in research of lipids and essential oils: Claude- Joseph Geoffroy, C.W. Scheele, M.E. Chevreul, J.J.E. Poutet, A.M. Zaitsev, S.A. Fokin, A. M. Goldovskii, G.V. Pigulevskii, K.P. Kardishev, S.L. Ivanov, Gildich, Kaufmann, Coleman, Alen, Karta, Datton, Hofman, Brokenhoff, Yakobashvili, Voitsechovich, Shlyapnikov, Basher, Wulfson, and others. Moreover, studies on v
vi Preface the composition and structure of lipids, lipophilic components and essential oils have been carried out by scientists of the Yunusov Institute of Plant Substances of the Academy of Sciences of the since 1961. They studied lipids and the lipophilic components of vegetative and generative organs of more than 1.500 plants. Essential oils are located in the flowers and leaves of plants and citrus fruits. More generally in plants, lipids are most often concentrated in the seeds and fruits. Quantities and composition of lipids, lipophilic components and essential oils vary widely and depend on the region where the plant grows, type of plant, environmental conditions, level of salt in soil, etc. In animals and fishes fat concentrates in and under the skin and in fatty tissues or in tissues surrounding internal organs, and participates extremely actively in the vital functioning of the organism (heart, kidney, intestines, etc.). Glycerides of fatty acids and phospholipids are in the brain and nervous tissues. Lipids, lipophilic components and essential oils are widely used in the food industry, pharmacy, engineering, perfumery and cosmetics, for the production of lacquers and pigments, etc. In this work, lipids, lipophilic components and essential oils are characterized based on the plant families where they were found. In creating this handbook, special attention was paid to Russian literature that is often not readily available to international scientists. This reference work is aimed at wide use by researchers and specialists working with lipids and essential oils in bioorganic chemistry, medicine, the food industry, pharmacy, fragrances, cosmetics, agriculture, and other industries.
Editorial Management Team Editor-in-Chief Shakhnoza S. Azimova Sciences of the Co-Editor Anna I. Glushenkova Sciences of the Assistent Editor Valentina I. Vinogradova Sciences of the vii
Table of Contents 1 Apiaceae... 1 2 Araliaceae... 29 3 Asteraceae... 37 4 Boraginaceae... 145 5 Cruciferae (Brassicaceae)... 173 6 Cucurbitaceae Juss.... 283 7 Ericaceae Juss. (Vacciniaceae S. F. Gray)... 325 8 Euphorbiaceae... 357 9 Lamiaceae... 389 10 Leguminosae... 549 11 Malvaceae... 609 12 Onagraceae... 637 13 Ranunculaceae Juss. (Coptaceae A. et D. Löve; Paeoniaceae Rudolphi)... 647 14 Rhamnaceae Juss.... 693 15 Rosaceae Juss.... 701 16 Rutaceae Juss.... 783 17 Salicaceae Mirb.... 861 18 Solanaceae... 873 Index of Compounds... 927 Index of Organisms... 961 ix
Authors D. T. Asilbekova Apiaceae; Araliaceae; Lamiaceae; Solanacea N. P. Bekker Cruciferae (Brassicaceae); Cucurbitaceae Juss.; Ericaceae Juss.; Ranunculaceae Juss.; Rhamnaceae Juss.; Rosaceae Juss.; Rutaceae Juss.; Salicaceae Mirb. T. V. Chernenko Malvacea A. I. Glushenkova Euphorbiaceae; Leguminosae N. T. Ul chenko Asteraceae; Boraginaceae; Onagraceae xi