Claude Moulis

Two tetrahydroquinoline alkaloids from Galipea officinalis

Abstract Two tetrahydroquinoline alkaloids have been isolated from the bark of Galipea officinalis Hancock. Their structures have been established by spectroscopic methods. The compounds were named angustureine (1,2,3,4-tetrahydro-2(n-pentyl)-1-methylquinoline) and galipeine (2-[(3′-hydroxy-4′-methoxy-phenylethyl)]-2,3,4-tetrahydro-1-methylquinoline).

Direct characterization of isoquinoline alkaloids in a crude plant extract by ion-pair liquid chromatography–electrospray ionization tandem mass spectrometry: example of Eschscholtzia californica

An ion-pair HPLC-ESI-MS-MS method has been developed for the direct and rapid characterization of isoquinoline alkaloids in a crudely purified extract of the aerial parts of Eschscholtzia californica (Papaveraceae). This plant was chosen because of its increasing use in pharmaceutical industries and because its well known alkaloid composition allows the optimization of the experimental procedure through an on-line analytical sequence. Thus, 14 isoquinoline alkaloids of different types were detected and characterized. The identities of these compounds were confirmed unambigously by their fragmentation and UV spectra obtained by LC-diode-array detection. Various experiments including tandem mass spectrometry and in-orifice collision induced dissociation were performed and prove that MS-MS is a very efficient technique to identify these compounds. An explanation for each isoquinoline alkaloid type MS-MS fragmentation pattern is proposed and indicates similar neutral and/or radical losses. The order of the fragmentation depended on the type of compound but the lost fragments were similar.

Analysis of minor flavonoids in Piper hostmannianum var. berbicense using liquid chromatography coupled with atmospheric pressure chemical ionization mass spectrometry.

The fragmentations of hydroxylated flavanones, chalcones and dihydrochalcones were investigated by direct loop injection using an ion trap mass spectrometry equipped with atmospheric pressure chemical ionization (APCI) probe. Some of them have been isolated from the leaves of Piper hostmannianum var. berbicense and standards were used to confirm their fragmentation behaviour. In negative ion mode, fragmentations of these three types of flavonoids revealed specific diagnostic ions which allowed us to identify aglycones in a crude plant extract. The major fragment ion obtained in MS/MS experiment for methoxylated chalcones is the neutral loss of a methyl radical whereas a H(2)O molecule is lost in the case of methoxylated dihydrochalcones. Methoxylated chalcones and flavanones isomers could be differentiated by the relative intensity ratio of [M-H-CH(3)]*(-) and [M-H-C(2)H(2)O](-) ions. Based on UV and MS data, a decision tree that includes UV lambda(max) absorptions and MS/MS diagnostic ions was built in order to obtain structural information of unknown compounds present in the extract. This tree was used to identify flavonoids in the ethyl acetate extract of P. hostmannianum var. berbicense leaves after analysis by high-performance liquid chromatography-diode array detection-atmospheric pressure chemical ionization ion trap multistage mass spectrometry. A total of 11 flavonoids were tentatively characterized based on the MS fragmentations pattern observed in MS(n) experiments.

An antioxidant sinapic acid ester isolated from Iberis amara

The isolation of 6-O-sinapoyl sucrose (1) from Iberis amara seeds and an evaluation of its antioxidative properties in comparison with sinapic acid and ascorbic acid are reported.

Molluscicidal and radical scavenging activity of quinones from the root bark of Caryopteris x clandonensis.

In the search for new molluscicidal natural products, the activity of the chloroform extract of the root barks of Caryopteris x clandonensis was tested. The LC(100) was <5 ppm. The fractionation and purification of the extract afforded 15-deoxyfuerstione, fuerstione and alpha-caryopterone as the main compounds. These compounds were tested against the snail Bulinus truncatus, an intermediate host snail of a schistosomiasis parasite and showed strong molluscicidal activity with LC(100)<4 ppm. In addition, they were found to have potent radical scavenging properties on superoxide radical.

Constituents of Pilocarpus trachylophus

Four flavonoids, two terpenoids and a mixture of three polyprenols have been isolated from the leaves of Pilocarpus trachylophus.

Three furano-diterpenes from the bark of Croton campestris

Abstract Three furano-diterpenes have been isolated from the dichloromethane extract of Croton campestris St Hil. roots. Their structures have been established by spectroscopic methods. The compounds were named velamone (ent-15,16-epoxy-2-oxo-3,13(16),14-clerodatrien), velamolone (ent-15,16-epoxy-20-hydroxy-2-oxo-3,13(16),14-clerodatrien) and velamolone acetate (ent-15,16-epoxy-20-acetoxy-2-oxo-3,13(16),14-clerodatrien).

Essential oil of leaves of Croton campestris St. Hilaire, its secretory elements, and its biological activity.

Abstract The structure of the secretory tissues and the essential oil of the leaves of Croton campestris St Hil. were studied. The oil isolated by hydrodistillation was analyzed by GC and GC/MS and was found to contain 75 components accounting for 92.9% of the total oil, with the major components being caryophyllene oxide (29.9%) and humulene oxide II (8.0%). Growth inhibitory activity of the active compounds in solution was evaluated by measuring Minimal Inhibitory Concentration using a broth micro-method. The Minimal Inhibitory Concentration of the leaf oil was 1.56 µg/mL for Staphylococcus aureus, 6.25 µg/mL for Enterrococcus hirae and 6.25 µg/mL for Candida albicans.

Anatomical study of secondary tuberized roots of Harpagophytum procumbens DC and quantification of harpagoside by high-performance liquid chromatography method.

Aim and Background: A botanical study is conducted to provide a standard diagnostic tool. In order to improve the quality assurance of the secondary tuberized roots of Harpagophytum procumbens, derived extract and phytomedicine, a simple, rapid, and accurate high-performance liquid chromatography (HPLC) method was developed to assess the harpagoside. Material and Mehods: This HPLC assay was performed on a reversedphase C18 column with methanol and water (50/50–V/V) as the mobile phase with a flow rate of 1.5 mL/min and using a monitoring wavelength at 278 nm. Results and Conclusion: This method was successfully applied to quantify these bioactive iridoid in an aqueous extract of H. procumbens and in its related phytomedicine “harpagophyton”. The result demonstrated that the quantification of harpagoside, indicating that the quality control of the bioactive ingredient in H. procumbens, derived extract and phytomedicine, is critical to ensure its clinical benefits.

Synthesis and Extraction of Pentalongin, A Naphthoquinoid From Mitracarpus Scaber

Abstract This paper describes an efficient synthetic route to pentalongin (1H-naphtho[2,3-c]pyran-5,10-dione), a naphthoquinoid isolated from the aerial parts of Mitracarpus scaber, and to the structurally-related compound psychorubrin(3-hydroxy-1H-3, 4-dihydronaphtho[2,3-c]pyran-5,10-dione).