Phytochemical study of launaea arborescens (butt.) murb

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PHYTOCHEMICAL STUDY OF HALOPHILA STIPULACEA (FORSSKÁL) ASCHERS
Botanical and systematic description

The seagrass Halophila stipulacea is one of the marine species which have entered in the Mediterranean from the Red Sea since the opening of the Suez Canal in 1869. The first record of Halophila stipulacea in the Mediterranean Sea was in Greece in 1894. H. stipulacea developed extensive meadows in the Eastern Mediterranean basin and now is extending its distribution into the western basin, in ports and near ports, in Levantine Sea, southern Aegean, Greece, Malta, Sicily, and Tunisia. It occupied sublittoral sediments, sandy and muddy bottoms, intertidal 65 m, but mainly at depth of 30-45 m, mostly in harbours, or in their vicinity.
Halophila stipulacea is known by its grazing for invertebrates and fishes.
Taxon : Halophila stipulacea (Forsskal, 1775) Aschers .
Family/Order/Class/Phylum: Hydrocharitaceae/Hydrocharitales/Liliopsida/Magniliophyta
(Angiosperm).
Plants are dioecious with male and female flowers produced at each leaf node. Rhizomes are creeping, branched and fleshy, and roots appear solitary at each node of the rhizome, unbranched and thick with dense soft root hairs. Pairs of leaves are distributed on petioles along a rhizome, rooted in the sand. Leaves from 3-8 mm wide, ovate, not narrowing at the base, thin and hairy, margin spinulose. Petioles are from 3-15 mm long.

PHYSICO-CHEMICAL METHODS
Optical Activity ([α]D)

Optical rotations of the compounds, containing one or more asymmetric centers, were measured on a Jasco DIP 370 digital polarimeter. The compounds were dissolved in chloroform or methanol and the rotation α of the polarized light was measured in a cell of 1 ml of volume and 10 cm of length at room temperature. The line D (589 nm) of a sodium lamp was used as source of incidental light.

Infrared Spectrometry (IR)

IR spectra were recorded on a BIORAD FTS 155 FT-IR spectrophotometer controlled by BIORAD Win IR software. The samples were dissolved in chloroform and then deposed as film on KBr pastille.

INTRODUCTION
CHAPTER 1: LITERATURE DATA
1. ASTERACEAE FAMILY
1.1 General introduction
1.2 Morphological and characteristics of Asteraceae
1.3 Importance of Asteraceae family
1.4 The tribe Cichorieae (synonym: Lactuceae)
1.5 Metabolites isolated from Lactuceae
1.6 Distribution of sesquiterpenoids subtypes in the genera of the Chicorieae
1.7 Major sesquiterpenoids isolated from some genera of Cichorieae
1.8 Major terpenoids isolated from some genera of Cichorieae (Lactuceae)
1.9 Major phenolic compounds isolated from some genera of Cichorieae (Lactuceae)
1.10 Description of the genus Launaea cassini (zollicoferia Dc)
1.10.1 Secondary metabolites isolated from the genus Launaea
1.10.2 Launaea nudicaulis (Hook).F
1.10.3 Launaea spinosa (Forssk)
1.10.4 Launaea residifolia (L.) Kunteze
1.10.5 Launaea asplenifolia (Hook)
1.10.6 Launaea mucronata (Forssk)
1.10.7 Launaea tenuiloba (Boiss)
1.10.8 Biological activities in plants of the genus Launaea
1.11 Marine phanerogams (seagrasses)
1.11.1 Taxonomy and distribution
1.11.2 Importance of seagrasses
1.11.3 Chemical investigations of seagrasses
1.12 Hydrocharitaceae family
1.12.1 The genus Halophila
1.12.2 Scientific classification
1.12.3 Selected species of Halophila
1.12.4 Secondary metabolites isolated from the genus Halophila
CHAPTER 2: STUDY OF TERPENOIDS AND FLAVONOIDS
2. TERPENOIDS
2.1 Introduction
2.2 Biosynthesis
2.3 Sesquiterpenoids
2.3.1 Germacranes and elemanes
2.3.2 Eudesmanes (selinanes)
2.3.3 Guaianes
2.4 Sesquiterpene lactones
2.5 Biological activities of sesquiterpene lactones
2.6 Triterpenoids
2.6.1 Biogenesis of triterpenes
2.6.2 Toxic activities of triterpenoids
2.7 Polyphenolic compounds
2.7.1 Flavonoids
2.7.2 Structure variation of flavonoids
2.7.3 Biosynthesis of flavonoids
2.7.4 Biological activities of flavonoids
CHAPTER 3: PHYTOCHEMICAL STUDY OF LAUNAEA ARBORESCENS (BUTT.) MURB
3.1 Botanical systematic and description
3.2 Collection of the material
3.3 Chemical investigation of Launaea arborescens: Extraction- purification
3.3.1 Aerial parts
3.3.2 Roots
3.4 Structural elucidation of isolated compounds
3.4.1 Triterpenoids structures
3.4.1.1 Structure elucidation of compound 292
3.4.1.2 Structure elucidation of compound 293.
3.4.1.3 Structure elucidation of compound 294
3.4.1.4 Structure elucidation of compound 295
3.4.1.5 Structure elucidation of compound 296
3.4.1.6 Structure elucidation of compound 297.
3.4.1.7 Structure elucidation of compound 298
3.4.1.8 Structure elucidation of compound 299
3.4.1.9 Structure elucidation of compound 300 and 301
3.4.1.10 Structure elucidation of compound 302
3.4.1.11 Structure elucidation of compound 303
3.4.1.12 Structure elucidation of compound 304
3.4.2 Sesquiterpenoids structures
3.4.2.1 Structure elucidation of guaianolide compounds
3.4.2.1.1 Compound 305
3.4.2.1.2 Compound 306
3.4.2.2 Related guaianolides structures: 307, 308, 309, 310 and 311
3.4.2.2.1 Compound 307
3.4.2.2.2 Compound 308.
3.4.2.2.3 Compound 309
3.4.2.2.4 Compound 310
3.4.2.2.5 Compound 311
3.4.2.2.6 Determination of the absolute configuration of compound 311
3.4.2.3 Structure elucidation of eudesmanolide compounds.
3.4.2.3.1 Compound 312
3.4.2.3.2 Compound 313
3.4.2.4 Structure elucidation of the germacranolide compounds
3.4.2.4.1 Compound 314
3.4.2.4.2 Compound 315
3.4.2.5 Related germacranolide structures: 316, 317 and 318
3.4.2.5.1 Compound 316
3.4.2.5.2 Compound 317.
3.4.2.5.3 Compound 318
3.5 Biological act ivit ies of new isolated compounds
CHAPTER 4: PHYTOCHEMICAL STUDY OF HALOPHILA STIPULACEA (FORSSKÁL) ASCHERS
4.1 Botanical systematic and description
4.2 Collection of the material, extraction and purification
4.3 Structural elucidation of isolated flavonoid compounds
4.3.1 Compound 322
4.3.2 Compound 323
4.3.3 Compound 324 and 325
4.3.4 Compound 326
4.3.5 Compound 327
4.3.6 Compound 328
4.3.7 Compound 286 and 287
CONCLUSION
CHAPTER 5: EXPERIMENTAL PART
5.1 Plants material
5.2 Chromatographic methods of analysis (analytical and preparative)
5.2.1 Thin layer Chromatography (TLC)
5.2.2 Column Chromatography
5.2.2.1 Adsorption chromatography
5.2.2.2 Size Exclusion Chromatography (SEC)
5.2.2.3 High Pressure Liquid Chromatography (HPLC)
5.3 Physico-chemical methods
5.3.1 Optical Activity ([α] D)
5.3.2 Infrared Spectrometry (IR)
5.3.3 Mass Spectroscopy (MS)
5.3.4 Nuclear Magnetique Resonance Spectroscopy (NMR)
5.4 Chemical methods
5.4.1 Hydrolysis of compound 311
5.4.2 Preparation of the ester derivative of compound 311a
5.4.3 Preparation of the Moscher esters derivative of compound311a
5.4.3.1 Compound 311c
5.4.3.2 Compound 311d
5.4.4 Preparation of the model Moscher esters
5.4.4.1 Compound Ia
5.4.4.2 Compound Ib
5.4.4.3 Compound IIa
5.4.4.4 Compound IIb
5.4.5 Hydrolysis of compound 311
5.5 Biological assays
5.6 Extraction and purification of Launaea arborescens
5.6.1 Aerial parts
5.6.2 Roots
5.7 Extraction and purification of Halophila stipulacea
5.8 Physical constants and spectral data of the isolated compounds
5.8.1 Triterpenoids
5.8.2 Sesquiterpenoids
5.8.3 Mosher derivatives
5.8.4 Flavonoids
5.8.5 Syphonosides
REFERENCES