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In Scienze E Tecnologie Farmaceutiche Ciclo XXIV

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In Scienze E Tecnologie Farmaceutiche Ciclo XXIV Università degli Studi di Cagliari DOTTORATO DI RICERCA In Scienze e Tecnologie Farmaceutiche Ciclo XXIV TITOLO TESI Isolamento e caratterizzazione chimico-strutturale di metaboliti secondari dal genere Ononis e Seseli. Settore scientifico disciplinari di afferenza Chimica farmaceutica (CHIM O8) Presentata da: Dott.ssa Anna Rita Saba Coordinatore Dottorato Prof. Elias Maccioni Tutor/Relatore Dott.ssa Laura Casu Dott. Marco Leonti Esame finale anno accademico 2010 – 2011 Ai miei cari Indice analitico SUMMARY ............................................................................................1 RIASSUNTO...........................................................................................3 1. INTRODUZIONE ...............................................................................5 1.1. Uso delle piante nella medicina popolare .............................................5 Bibliografia ......................................................................................11 2. IL GENERE ONONIS ........................................................................13 2.1. Sistematica .................................................................................13 2.1.1 Introduzione.............................................................................13 2.1.2 Caratteristiche del genere Ononis .................................................13 2.1.3 Distribuzione in Italia..................................................................14 2.2. Fitochimica del genere Ononis ...................................................14 2.2.1 I flavonoidi...............................................................................14 2.2.1.1 Struttura e proprietà chimico-fisiche...........................................14 2.2.1.2 Distribuzione e funzione nelle piante ..........................................16 2.2.1.3 Attività farmacologiche e terapeutiche........................................19 2.2.2 I resorcinoli ..............................................................................22 2.2.2.1 Introduzione ..........................................................................22 2.2.2.2 Attività biologica .....................................................................28 2.2.3 Le isocumarine..........................................................................29 Bibliografia ......................................................................................32 3. ONONIS NATRIX L..........................................................................36 3.1. Caratteristiche della pianta ........................................................36 3.2. Luogo di raccolta.........................................................................37 3.3. Risultati fitochimici dell’Ononis natrix L.....................................38 3.4. Estrazione e isolamento .............................................................40 3.4.1 Frazionamento dell’estrattto diclorometanico ................................40 3.5. Delucidazione delle strutture note isolate dall’Ononis natrix L .46 3.5.1 2’,4’-dihydroxy-dihydrochalcone ..................................................46 3.5.2 2’,4’-dihydroxy-6’-methoxydihydrochalcone...................................49 3.5.3 2’,6’-dihydroxy-4’-methoxydihydrochalcone...................................52 3.5.4 2’,6’-dihydroxy-4,4’-dimethoxydihydrochalcone .............................55 3.5.5 2’,4-dimethoxy-4’,6’-dihydroxydihydrochalcone .............................58 3.5.6 2’,4’-dihydroxy-4-methoxydihydrochalcone ...................................61 3.5.7 2’,4’-dihydroxychalcone ..............................................................63 3.5.8 5,7-dihydroxy-6-methoxyflavanone ..............................................66 3.5.9 7-hydroxyflavanone....................................................................69 3.5.10 7-hydroxy-8-methoxyflavanone..................................................72 3.5.11 5,7-dihydroxyflavanone.............................................................75 3.5.12 5-methoxy-7-hydroxyflavanone..................................................78 3.5.13 7-hydroxy-8-methoxyflavone .....................................................80 3.5.14 5,7-dihydroxy-6-methoxyflavone ................................................83 3.6. Delucidazione delle strutture nuove isolate dall’Ononis natrix L........................................................................................86 3.6.1 Composto 15 .............................................................................86 3.6.2 Composto 16 .............................................................................95 3.6.3 Composto 17 ...........................................................................103 3.7. Risultati biologici sui composti isolati dall’Ononis natrix L ......110 3.7.1 Screening biologico preliminare..................................................110 3.7.2 Risultati biologici .....................................................................111 Bibliografia .....................................................................................114 4. IL GENERE SESELI .........................................................................117 4.1. Sistematica ...............................................................................117 4.1.1 Introduzione...........................................................................117 4.1.2 Caratteristiche del genere Seseli.................................................118 4.1.3 Distribuzione in Italia................................................................118 4.2. Fitochimica del genere Seseli....................................................119 4.2.1 Le cumarine ...........................................................................119 4.2.1.1 Struttura e proprietà chimico-fisiche.........................................119 4.2.1.2 Distribuzione e funzione nelle piante ........................................121 4.2.1.3 Le cumarine nel genere Seseli..................................................122 4.2.1.4 Attività farmacologiche e terapeutiche......................................126 4.2.2 I cromoni ...............................................................................127 4.2.3 Finilpropanoidi .......................................................................128 4.2.4 Lignani ..................................................................................129 4.2.5 Terpeni..................................................................................130 4.2.6 Sesquiterpeni .........................................................................131 4.2.7 Poliacetileni ...........................................................................133 4.2.7.1 I poliacetileni nel genere Seseli ................................................134 Bibliografia ....................................................................................137 5. SESELI PRAECOX........................................................................142 5.1. Caratteristiche della pianta ......................................................142 5.2. Luogo di raccolta.......................................................................143 5.3. Risultati fitochimici della Seseli praecox ..................................144 5.4. Estrazione e isolamento ...........................................................147 5.4.1 Frazionamento dell’estratto diclorometanico...............................147 5.5. Delucidazione delle strutture note isolate dalla Seseli praecox .....................................................................................151 5.5.1 9-(acetyloxy)8,8-dimethyl-2-oxo-9,10-dihydro-2H,8H-pyrano[2,3-f] chromen-10-yl (Z)-2-methyl-2-butenoate ...........................................151 5.5.2 9-(acetyloxy)8,8-dimethyl-2-oxo-9,10-dihydro-2H,8H-pyrano[2,3-f] chromen-10-yl-3-methylbutenoate ...................................................155 5.5.3 9-(acetyloxy)8,8-dimethyl-2-oxo-9,10-dihydro-2H,8H-pyrano[2,3-f] chromen-10-yl-2-methylbutenoate ...................................................159 5.5.4 9-(acetyloxy)8,8-dimethyl-2-oxo-9,10-dihydro-2H,8H-pyrano[2,3-f] chromen-10-yl-2-methylpropanoate .................................................163 5.5.5 9,10-dihydroxy-8,8-dimethyl-9,10-dihydro-2H,8H-pyrano[2,3-f] chromen-2-one ..............................................................................167 5.5.6 Phellopterina..........................................................................170 5.5.7 Bergaptene ............................................................................173 5.5.8 Imperatorina ..........................................................................176 5.5.9 Isoimperatorina ......................................................................179 5.5.10 4-(2,3-dihydroxy-3-methylbutoxy)-7H-furo[3,2-g]chromen-7-one..182 5.5.11 7-methoxy-5-[(3-methyl-2-butenyl)oxy]-2H-chromen-2-one .........184 5.5.12 Peucenin-7-methyl ether ........................................................187 5.5.13 Falcarinolo............................................................................189 5.5.14 Falcarindiolo .........................................................................192 5.5.15 5-hydroxy-6-(2-Z-butenyl-3-hydroxymethyl)-7-methoxy-2- methylchromone ............................................................................195 5.6. Delucidazione della nuova struttura isolata dalla Seseli praecox .....................................................................................198 5.6.1 Composto 15 ..........................................................................198
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