Haralambos E. Katerinopoulos
Professor of Organic Chemistry
Tel: +30 2810 545026
Fax: +30 2810 545001
E-mail:
kater@chemistry.uoc.gr
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http://www.chemistry.uoc.gr/katerinopoulosEducation
1 POST-GRADUATE
Analysis of natural products from plants from the floral of Crete Rosmarιnus officinalis L, Origanum dictamnus L και Cistus creticus ssp. creticus (L) Greuter et Burdet and elucidation of the structure of a new component of the essential oil of C. creticusCreticus
Georgia Pagona
005pagona July 2005
The subject of this thesis is the study of the components of the essential oils from three species namely, Rosmarinus officinalis L., Origanum dictamnus L. and Cistus creticus ssp. creticus (L.) Greuter et Burdet which are common plants of the flora of Crete. The essential oils contain substances, which originate via the secondary metabolism of plants, and are used for the interaction of the plants with their environment. These components are vital for some basic functions of the plants such as reproduction and protection from insects and parasites. Exploitation of these properties could lead to safer and more environmentally friendly methods for crop protection. The first part of this thesis includes the analysis of the components of the essential oils from the aforementioned plants, the determination of their chemical structure and the classification of each essential oil according to the area of origin. The essential oil, as well as a number of extracts of Rosmarinus officinalis L. in solvents of increasing polarity, were isolated and their components identified and tested by N.AG.R.E.F. (Plant Protection Institute-Heraklion), as biological agents in pest control. In the second part, the elucidation of the structure of a new compound, isolated from the essential oil of the resin from Cistus creticus ssp. creticus (L.) Greuter et Burdet, is presented. This component was initially identified as a labdane analog, namely, 1,1,4a,6-tetramethyl-5-methylene-1,2,3,4,4α,5,8,8α-octahydronaphthalene. Based on the data from one- and two-dimensional NMR spectroscopy the structure of the compound was redefined as that of an eremophilene isomer with the IUPAC name 1,2,3,4,6,7,8,8aoctahydro- 1,8a-dimethyl-7-(1-methylethenyl)naphthalene.How to view this document Display the whole document in one of the following formats.Portable Document Format 1681716 bytes.You are granted permission for the non-commercial reproduction, distribution, display, and performance of this document in any format, BUT this permission is only for a period of 45 (forty-five) days from the most recent time that you verified that this document is still available from the University of Crete under terms that include this permission. All other rights are reserved by the author(s).
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2 POST-GRADUATE
Synthetic Approaches towards the Drimane Sesquiterpenes cis- and trans-1,1,4α,6-tetramethyl-5-methylene-1,2,3,4,4α,5,8,8α-octahydronaphthalenes .
Konstantinos Hatzellis
2002hatzellis July 2002
Labdanum (Cistus creticus, ssp creticus L., Greuter et Burdet) is a perennial shrub that grows in the Mediterranean area, especially in Crete. During the hot summer days its leaves secrete a thick, aromatic resin, called by the locals “ladano”. One of the components isolated from the essential oil of the resin was assigned the structure of a drimane type sesquiterpene namely 1,1,4a,6-tetramethyl-5-methylene-1,2,3,4,4a,5,8,8a-octahydro-napthalene (figure 1). Given that the stereochemistry of the fusion of the decalin ring had not been specified, the aims of the present project were twofold: a) The design of a flexible synthetic pathway towards the target molecules, which upon simple synthetic deviations would lead to both cis / trans isomers. b) The total synthesis of both targets and the comparison of their spectral profiles with those of the natural product. During this project the first target was attained and the second one was realized to the point of total synthesis of the cis isomer in 85% purity. Comparison of spectroscopic data of the synthesized cis-isomer with those from the literature on the trans analog as well as the natural product, indicates that the latter has a different structure than either the cis or trans isomers.How to view this document Display the whole document in one of the following formats. Portable Document Format 2360141 bytes.(compressed on disk, will be sent uncompressed) You are granted permission for the non-commercial reproduction, distribution, display, and performance of this document in any format, BUT this permission is only for a period of 45 (forty-five) days from the most recent time that you verified that this document is still available from the University of Crete under terms that include this permission. All other rights are reserved by the author(s).
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