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Nwjlfk F”K{Kk Funs”Kky; Yfyr Ukjk;.K Feffkyk Fo”Ofo|Ky; Dkes”Ojuxj] Njhkaxk&846008 Nwjlfk F”K{Kk Funs”Kky; Laiknd Eamy

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Nwjlfk F”K{Kk Funs”Kky; Yfyr Ukjk;.K Feffkyk Fo”Ofo|Ky; Dkes”Ojuxj] Njhkaxk&846008 Nwjlfk F”K{Kk Funs”Kky; Laiknd Eamy M.Sc. CHEMISTRY OF NATURAL PRODUCTS M.Sc. Chemistry Paper-XIV CHE-114 nwjLFk f”k{kk funs”kky; yfyr ukjk;.k fefFkyk fo”ofo|ky; dkes”ojuxj] njHkaxk&846008 nwjLFk f”k{kk funs”kky; laiknd eaMy 1. izks- ljnkj vjfoUn flag % funs”kd] nwjLFk f”k{kk funs”kky;] y- uk- fefFkyk fo”ofo|ky;] njHkaxk 2. MkW- vkj- ds- pkS/kjh % jlk;u”kkL= foHkkx] y- uk- fefFkyk fo”ofo|ky;] njHkaxk 3. çks- ds- ds- >k % jlk;u”kkL= foHkkx] y- uk- fefFkyk fo”ofo|ky;] njHkaxk 4. MkW- “kaHkq çlkn % lgk;d funs”kd] nwjLFk f”k{kk funs”kky;] y- uk- fefFkyk fo”ofo|ky;] njHkaxk ys[kd ,oa leUo;d çks- ds- ds- >k Dr. Shambhu Prasad-Co-ordinator, DDE, LNMU, Darbhanga fç;&Nk=Xk.k nwj f”k{kk C;wjks&fo”ofo|ky; vuqnku vk;ksx] ubZ fnYyh ls ekU;rk çkIr ,oa laLrqr ,e- ,l- lh- ¼nwjLFk ekè;e½ ikB~;Øe ds fy, ge gkÆnd vkHkkj izdV djrs gSaA bl Lo&vfèkxe ikB~; lkexzh dks lqyHk djkrs gq, gesa vrho izlUurk gks jgh gS fd Nk=x.k ds fy, ;g lkexzh izkekf.kd vkSj mikns; gksxhA (Chemistry of Natural Products) uked ;g vè;;u lkexzh vc vkids le{k gSA ¼çks- ljnkj vjfoUn flag½ funs”kd izdk”ku o’kZ 2019 nwjLFk ikB~;Øe lEcU/kh lHkh izdkj dh tkudkjh gsrq nwjLFk f”k{kk funs”kky;] y- uk- fEkfFkyk ;wfuoflZVh] dkes”ojuxj] njHkaxk ¼fcgkj½&846008 ls laidZ fd;k tk ldrk gSA bl laLdj.k dk izdk”ku funs”kd] nwjLFk f”k{kk funs”kky;] yfyr ukjk;.k fefFkyk ;wfuoflZVh] njHkaxk gsrq esllZ y{eh ifCyds”kal çk- fy- fnYyh }kjk fd;k x;kA DLN-3419-148.50-CHEM NATURAL PROD CHE114 C— Typeset at : Atharva Writers, Delhi Printed at : nwjLFk f'k{kk funs'kky; yfyr ukjk;.k fEkfFkyk fo'ofo|ky;] dkes’ojuxj] njHkaxk&846004 ¼fcgkj½ Qksu ,oa QSSSSDl % 06272 & 246506] osclkbZV % www.ddelnmu.ac.in, bZ&esy % [email protected] ekuuh; dqyifr y- uk- fe- fo'ofo|ky; fç; fo|kFkhZ nwjLFk f’k{kk funs’kky;] yfyr ukjk;.k fefFkyk fo’ofo|ky; }kjk fodflr rFkk fofHkUu fudk;ksa ls vuq’kaflr Lo&vf/kxe lkexzh dks lqyHk djkrs gq, vrho çlUurk gks jgh gSA fo’okl gS fd nwjLFk f’k{kk ç.kkyh ds ek/;e ls mikf/k çkIr djus okys fo|kÆFk;ksa dks fcuk fdlh cká lgk;rk ds fo”k;&oLrq dks xzká djus esa fdlh çdkj dh dksbZ dfBukbZ ugha gksxhA ge vk’kk djrs gSa fd ikB~;&lkexzh ds :i esa ;g iqLrd vkids fy, mi;ksxh fl) gksxhA çks- ¼MkW-½ ,l- ds- flag dqyifr CONTENTS Chapters Page No. 1. Terpenoids and Carotenoids 1 2. Alkaloids 101 3. Vitamins 118 4. Steroids and Hormones 136 5. Rotenoids and Porphyrins 170 Terpenoids and CHAPTER – 1 Carotenoids TERPENOIDS AND NOTES CAROTENOIDS STRUCTURE 1.1 Learning Objectives 1.2 Introduction 1.3 Isolation of Monoterpenes and Sesquiterpenes 1.4 General Methods of Determining Structure 1.5 Monoterpenes 1.6 Monocyclic Monoterpenes 1.7 Bicyclic Monoterpenes 1.8 Sesquiterpenes 1.9 Acyclic Sesquiterpenes 1.10 Monocyclic Sesquiterpenes 1.11 Bicyclic Sesquiterpenes 1.12 Diterpenes 1.13 Carotenes 1.14 Summary 1.15 Review Questions 1.16 Further Readings 1.1 LEARNING OBJECTIVES After studying the chapter, students will be able to: zzTo definition the Diterpenes & Carotenes zzTo discuss the Monocyclic Monoterpenes zzTo describe the General Methods of Determining Structure zzThe understand the Monoterpenes & Monocyclic Monoterpenes 1.2 INTRODUCTION The terpenes form a group of compounds the majority of which occur in the plant kingdom; a few terpenes have been obtained from other sources. The simpler mono- and sesquicentennial are the chief constituents of the essential oils; these are the volatile oils obtained from the Self-Instructional Material 1 Chemistry of Natural sap and tissues of certain plants and trees. The essential oils have been used in perfumery Products from the earliest times. The di- and triterpenes, which are not steam volatile, are obtained from plant and tree gums and resins. The tetraterpenes form a group of compounds known as the caro tenoids, and it is usual to treat these as a separate group. Rubber is the most NOTES important polyterpene. Most natural terpene hydrocarbons have the molecular formula {C5H8)n, and the value of n is used as a basis of classification. Thus we have the following classes {these have already been mentioned above): {i) Monoterpenes, C10H16 {ii) Sesquiterpenes, C15H24 {iii) Diterpenes, C20H32 {iv) Triterpenes, C30H48 (v) Tetraterpenes, C40H64 (these are the carotenoids). (vi) Polyterpenes, (C5H8)n In addition to the terpene hydrocarbons, there are the oxygenated derivatives of each class which also occur naturally, and these are mainly alcohols, aldehydes or ketones. The term terpene was originally reserved for those hydrocarbons of molecular formula C10H16, but by common usage, the term now includes all compounds of the formula (C5H8)n. There is, however, a tendency to call the whole group terpenoids instead of terpenes, and to restrict the name terpene to the compounds C10H16. The thermal decomposition of almost all terpenes gives isoprene as one of the products, and this led to the suggestion that the skeleton structures of all naturally occurring terpenes can be built up of isoprene units; this is known as the isoprene rule, and was first pointed out by Wallach (1887). Thus the divisibility into isoprene units may be regarded as a necessary condition to be satisfied by the structure of any plant-synthesised terpene. Furthermore, Ingold (1925) pointed out that the isoprene units in natural terpenes were joined “head to tail” (the head being the branched end of isoprene). This divisibility into isoprene units, and their head to tail union, may conveniently be referred to as the special isoprene rule. It should be noted, however, that this rule, which has proved very useful, can only be used as a guiding principle and not as a fixed rule. Several exceptions to it occur among the simpler terpenes, e.g., lavandulol is composed of two isoprene units which are not joined head to tail; also, the carotenoids are joined tail to tail at their centre. CH3 CH1 CH3 C=CH.CH2.CH—C CH 3 CH3 CH2=C—CH=CH2 CH2OH lavandulol isoprene The carbon skeletons of open-chain monoterpenes and sesquiterpenes are: C C CCCCCCCC head tail head tail C C C CCCCCCC CCCCC 2 Self-Instructional Material Monocyclic terpenes contain a six-membered ring, and in this connection Ingold (1921) Terpenoids and pointed out that a gem-dialkyl group tends to render the cyclohexane ring unstable. Hence, Carotenoids in closing the open chain to a cyclo hexane ring, use of this “gem-dialkyl rule” limits the number of possible structures. Thus the monoterpene open chain can give rise to only one possibility for a monocyclic monoterpene, viz., the p-cyrnene structure. This is shown in the NOTES following structures, the acyclic structure being written in the conventional “ ring shape “. C C C C C C C C C C C C C C C C C C C C acyclic structure p-cymene structure All natural monocyclic monoterpenes are derivatives of p-cyrnene. Bicyclic monoterpenes contain a six-membered ring and a three-, four or five-memberedring. Ingold (1921) also pointed out that cyclopropane and cyclobutane rings require the introduction of a gem-dimethyl group to render them sufficiently stable to be capable of occurrence in nature. Thus closure of the 10C open chain gives three possible bicyclic structures; all three types are known. C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C If we use these ideas with the sesquiterpene acyclic structure, then we find that only three monocyclic and three bicyclic structures are possible (not all are known; see the sesquiterpenes). C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C Self-Instructional Material 3 Chemistry of Natural Recently some furano-terpenes have been isolated, e.g., dendrolasin, which is believed Products to have the following structure (Quilico et al., 1957); it contains three isoprene units joined head to tail. CH2.CH2.CH=C.CH2.CH2.CH=CMe2 NOTES O Me The carotenoids are yellow or orange pigments which are widely distributed in plants and animals. Chlorophyll is always associated with the carotenoids carotene and lutein; the carotenoids act as photo sensitisers in conjunction with chlorophyll. When chlorophyll is absent, e.g., in fungi, then the carotenoids are mainly responsible for colour. Cltro tenoids are also known as lipochromes or chromolipids because they are fat-soluble pigments. They give a deep blue colour with concentrated sulphuric acid and with a chloroform solution of antimony trichloride (the Carr-Price reaction); this Carr-Price reaction is the basis of one method of the quantitative estimation of carotenoids. Some carotenoids are hydro carbons; these are known as the carotenes, other carotenoids are oxygenated derivatives of the carotenes; these are the xanthophylls. There are also acids, the carotenoid acids, and esters, the xanthophyll esters.
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