New tricyclic and tetracyclic pyranocoumarins with an unprecedented C-4 substituent. Structure elucidation of tamanolide, tamanolide D and tamanolide P from Calophyllum inophyllum of French Polynesia.

Three new pyranocoumarin derivatives, tamanolide (1), tamanolide D (2) and tamanolide P (3), were isolated from the almond seeds of Calophyllum inophyllum L. (Clusiaceae) grown in French Polynesia. These compounds, having an unprecedented C-4 isobutyl substituent, have been characterized as a new class of pyranocoumarins called tamanolides. Their structures were elucidated on the basis of 1D and 2D NMR techniques (COSY, NOESY, HSQC and HMBC) in association with MS (HR-ESI-MS) data analysis.

Structures of cadinane- and guaiane-type sesquiterpenoids from Enterospermum madagascariensis (Baill.) Homolle.

Three new cadinane- and guaiane-type sesquiterpenoids, 2-hydroxy-10-epi-zonarene 1, 2, 15-dihydroxycalamenene 2 and guaia-4, 6-dien-3-one 3, were isolated from the wood of Enterospermum madagascariensis (Rubiaceae) grown in Madagascar. Their structures were established from concerted application of 2D NMR techniques including gs-COSY, gs-HMQC, gs-HMBC and NOESY.

Structures of new secofriedelane and friedelane acids from Calophyllum inophyllum of French Polynesia.

Three new friedelane-type triterpenoids, 3,4-secofriedelan-3,28-dioic acid (1), 27-hydroxyacetate canophyllic acid (2) and 3-oxo-27-hydroxyacetate friedelan-28-oic acid (3), were isolated from the leaves of Calophyllum inophyllum (Clusiaceae) grown in French Polynesia. Their structures were established by the concerted application of 2D NMR techniques including gs-COSY, gs-HMQC and gs-HMBC.

[Study of the antimicrobial action of various essential oils extracted from Malagasy plants. II: Lauraceae]. / Contribution à l'étude de l'action antimicrobienne de quelques huiles essentielles extraites de plantes malgaches. II: Les lauracees.

The microbial growth inhibitory properties of some Lauraceae essential oils, Laurus nobilis, Cinnamomum zeylanicum (cinnamon) and Ravensara anisata were studied by the determination of their respective M.I.C. (Minimal Inhibitory Concentration). Five bacterial strains, one fungi and two yeasts were used to evaluate the essential oils inhibitory capacities. These vegetable extracts, with decrease activity, were range also: C. zeylanicum--bark greater than R. anisata--bark greater than C. zeylanicum--leaves greater than L. nobilis greater than R. anisata--leaves. The essential oils extracted from cinnamon and R. anisata--bark were very interesting by their antifungic activities.

[Antibacterial action of essential oils extracted from Madagascar plants]. / Contribution à l'étude de l'action antibactérienne de quelques huiles essentielles extraites de plantes malgaches.

The following aromatherapy study reports the antimicrobial activity of eight Malagasy essential oils by the determination of their respective M.I.C. (Minimal Inhibitory Concentration) on enteropathogenic and spoilage bacteria strains. The aromatic plants used were taken from the Labiatae family (Thymus vulgaris, Ocimum gratissimum), the Myrtaceae family (Eugenia caryophyllata, Melaleuca viridiflora) and the Compositae (Helichrysum lavanduloides, H. bracteiferum, H. gymnocephalum, Psiadia altissima). Their inhibitory effect were tested on eight referied strains commonly used for antibiotic measurements and also on twelve others enteropathogenic bacteria strains. The results showed that three oils from Thymus vulgaris, Ocimum gratissimum and Eugenia caryophyllata were particularly efficient with a large spectra action. We noticed that the essential oil of Melaleuca viridiflora had also a high inhibitory effect especially on Gram positive bacteria.

Determination of sterol and triterpene alcohol acetates in natural products by reversed-phase liquid chromatography and gas chromatography-mass spectrometry.

A partial separation of nine sterol acetates and seven triterpene alcohol acetates by reversed-phase liquid chromatography is described. Good results are obtained using acetonitrile-water (90:10, v/v) as mobile phase with an UV detector at 205 nm. The variation in sterol sensitivity shows that this technique is not suitable for quantitative analyses. A combination of this technique for the fractionation of the natural sterol mixture, gas-liquid chromatography for quantitation and gas chromatography-mass spectrometry for identification is necessary for the determination of sterol compounds contained in natural products. An example of the separation, identification and quantitation of sterol acetates from sunflower seed oil is given.

Fatty acid composition of seed oils from sixAdansonia species with particular reference to cyclopropane and cyclopropene acids.

The oil content of sixAdansonia species (Bombacaceae family) of Madagascar (Adansonia grandidieri, A. za, A. digitata, A. fony, A. madagascariensis andA. suarenzensis) and Africa (A. digitata) ranges from 8 to 46%. All the oils give a positive response to the Halphen test. Malvalic, sterculic and dihydrosterculic acids were detected using gas liquid chromatography-mass spectrometry (GLC-MS). Epoxy or hydroxy fatty acids were not found in these oils. Fatty acid composition was determined by GLC using glass capillary columns coated with BDS and Carbowax 20 M. Results obtained for cyclopropenic fatty acids (CPEFA) were compared to those given by glass capillary GLC after derivatization with silver nitrate in methanol, by hydrogen bromide titration and by proton magnetic resonance (PMR). Good agreement was observed for the results given by the various methods. Malvalic acid content ranges from 3 to 28%, sterculic acid from 1 to 8% and dihydrosterculic acid from 1.5 to 5.1%. Odd-numbered fatty acids (Pentadecanoic and hepatadecanoic) were also observed in minute amounts (0.1-1.1%). Among the normal fatty acids, we observed mainly palmitic (21-46%), oleic (15-40%) and linoleic (12-32%). The relationship between fatty acid composition andAdansonia species is discussed.