Cutillo, Francesca (2006) Chemistry and phytotoxicity of secondary metabolites from Mediterranean plants. [Tesi di dottorato] (Unpublished)

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Item Type: Tesi di dottorato
Language: English
Title: Chemistry and phytotoxicity of secondary metabolites from Mediterranean plants
Creators:
CreatorsEmail
Cutillo, FrancescaUNSPECIFIED
Date: 2006
Date Type: Publication
Number of Pages: 174
Institution: Università degli Studi di Napoli Federico II
Department: Chimica organica e biochimica
PHD name: Scienze chimiche
PHD cycle: 18
PHD Coordinator:
nameemail
Lanzetta, RosaUNSPECIFIED
Tutor:
nameemail
Della Greca, MarinaUNSPECIFIED
Date: 2006
Number of Pages: 174
Uncontrolled Keywords: Allelopathy, Purification techniques, Spectroscopic analysis
MIUR S.S.D.: Area 03 - Scienze chimiche > CHIM/06 - Chimica organica
Date Deposited: 30 Jul 2008
Last Modified: 30 Apr 2014 19:24
URI: http://www.fedoa.unina.it/id/eprint/993

Abstract

[ENGLISH] During the three years of my PhD studies, three Mediterranean plants have been analysed, Brassica fruticulosa, Chenopodium album and Malva silvestris. The metabolites obtained by infusion and by using a new extraction procedure, have been purified by different chromatographic techniques (CC, TLC, HLPC, DCCC), while their structural characterisation has been performed by spectroscopic and spectrometric techniques (1H and 13C NMR, UV, IR, CD, ESI MS, MALDI MS, GC MS). The investigation of the three Mediterranean plants has led to the identification of: seven lignans, four neolignans, five sesquilignans, one dilignan, eight C-13 nor-terpenes, three degraded carotenoids, two monoterpenes, one sesquiterpene, one diterpene, nineteen phenol derivatives, one triptammine, one benzaldeid derivative, three allenes and eight cinnamic amides. Among them, thirteen compounds have been isolated for the first time. Absolute stereochemistry of some compounds has been defined through the application of Mosher’s method. Some of the isolated compounds have been tested on seeds of standard plants [Lactuca sativa L (lettuce), Lycopersicon esculentum M. (tomato), Allium cepa L. (onion)] to evaluate their biological activity. The results reported have shown a strong inhibiting effect of many lignans, which inhibit germination and growth of the standard species down to 1 nM concentration. At these concentrations commercial herbicides are usually inactive. Such a potent bioactivity for very diluted solution of lignans suggests further in vitro and in fields investigations, to fully evaluate the potential use of these molecules as natural herbicides. In this thesis the use of FTICR mass spectrometry is also described. In a research project of a nine-months Marie Curie fellowship, this technique has been employed for studying the charge states distribution of Calmodulin and modalities of interaction of the protein in a biological environment. / [ITALIANO] Tre piante spontanee dell’area Mediterranea, Brassica fruticulosa, Chenopodium album e Malva silvestris, sono state sottoposte ad indagine sistematica, allo scopo di definire la natura e le caratteristiche chimiche dei metaboliti secondari prodotti dai tre organismi vegetali. I metaboliti, ottenuti dalle tre piante mediante metodiche infusive ed estrattive, sono stati purificati attraverso tecniche cromatografiche (CC, TLC, DCCC, HPLC) e caratterizzati mediante spettroscopia (UV, IR, 1H-NMR, 13C-NMR, CD) e spettrometria di massa (GC-MS, MALDI-MS, ESI-MS). Sono stati in tal modo isolati: sette lignani, quattro neolignani, cinque sesquilignani, un dilignano, otto C-13 nor-terpeni, tre carotenoidi degradati, due monoterpeni, un sesquiterpene, un diterpene, diciannove derivati fenolici, un derivato triptamminico e uno benzaldeidico, tre alleni e otto ammidi cinnamiche. Tredici di questi composti sono stati isolati per la prima volta. Molti dei metaboliti isolati sono stati sottoposti a saggi di fitotossicità su organismi vegetali di riferimento, allo scopo di definirne l’eventuale bioattività. Fra tutti, i composti aventi una struttura di tipo lignanico, hanno mostrato un’intensa attività inibente la germinazione delle specie vegetali testate. E’ inoltre riportato lo studio della modalità di interazione della Calmodulina con il peptide RS20, realizzato durante un periodo speso presso l’Università di Warwick (UK). Tale analisi è stata svolta adoperando uno spettrometro di massa FTICR accoppiato ad una sorgente ESI.

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