Data for: Dimeric and esterified sesquiterpenes from the Liverwort Chiastocaulon caledonicum
1D and 2D NMR spectra, UV-vis., IR, HREI-MS and polarimetry data of the new compounds : (+)-4α-ac... more 1D and 2D NMR spectra, UV-vis., IR, HREI-MS and polarimetry data of the new compounds : (+)-4α-acetoxy-gymnomitr-3(15)-ene (1), (+)-9α-acetoxy-gymnomitr-3(15)-ene (2), (-)-4-hydroxy-β-barbatene-9-cinnamate (3), (+)-1-oxo-gymnomitr-2β,15-diol (4), (+)-myltayl-5-one-4β-ol (8), chiastaucolin A (9) and chiastaucolin B (10) are shown in a single pdf file.
Effect of cyclic fatty acid monomers on fat absorption and transport depends on their positioning within the ingested triacylglycerols
Journal of Lipid Research, 1997
We investigated the intestinal digestion of cyclic fatty acid monomers (CFAM) isolated from heate... more We investigated the intestinal digestion of cyclic fatty acid monomers (CFAM) isolated from heated linseed oil and their effects upon fatty acid lymphatic transport and lipoprotein profile in lymph. These cyclic fatty acid monomers were acylated in specific positions in the glycerol backbone of triacylglycerols (sn-(1/3) position for the 1C oil, sn-2 position for the 2C oil and together in the sn-1,2, and 3 positions for the 3C oil) and administered intragastrically to lymph-canulated rats. Their lumenal digestibility was also assessed in vitro using a pancreatic lipase assay. The lipase activity was 1.9 to 6.6 less towards the triacylglycerols acylated with cyclic fatty acids compared to control. The lowest activity was with the 2C oil. In the hydrolytic products, the cyclic fatty acid contents were similar between the experimental groups. When absorbed as 2-monoacyl-sn-glycerol (2C oil), cyclic fatty acid monomers were better and unselectively recovered into the lymph than when absorbed as free fatty acids (1C oil). In that latter situation, the bulkier cyclic fatty acids (C6 and cis membered-ring CFAM) were transported into the lymph to a lesser extent. The appearance of the lymphatic chylomicrons was delayed in rats fed the 1C oil. Cyclic fatty acid monomers from the 2C oil only increased the lymphatic transport of saturated fatty acids (80%). Cyclic fatty acids from the 3C oil (absorbed as 2-monoacyl-sn-glycerol and free fatty acid) usually elicited intermediary effects. We conclude that the effects of cyclic fatty acid monomers upon the intestinal metabolism are greatly influenced by their positioning within the triacylglycerol and that the structure of the cyclic fatty acids influences their lymphatic recovery only when they are absorbed as free fatty acid.
This is the first chemical investigation of Chiastocaulon caledonicum, an endemic liverwort from ... more This is the first chemical investigation of Chiastocaulon caledonicum, an endemic liverwort from New Caledonia. We herein present the isolation of thirteen compounds including seven undescribed sesquiterpenoids, namely four barbatane-and three myltaylane-type sesquiterpenes. The structures of these compounds were elucidated based on the interpretation of their chemical and spectroscopic/spectrometric data. Chiastocaulins A and B are the first examples of dimers based on two myltaylane units. The chemotaxonomic importance and the biosynthesis of the chiastocaulin structure are discussed. Terpenoid dimers formed via a Diels-Alder cyclisation are thought to be specific to the Plagiochilaceae family.
The first chemotaxonomic study based on volatile components of Porella viridissima (Mitt.) Grolle... more The first chemotaxonomic study based on volatile components of Porella viridissima (Mitt.) Grolle is reported. The GC-MS analysis of ether extract was performed; ten santalane and five pinguisane-type sesquiterpenes were identified together with perrottetianal A as major diterpene. Most of detected santalane-type sesquiterpenes are reported for the first time in liverwort. P. viridissima was found to belong to the chemotype III (pinguisane/sacculatane) and shared chemical similarities with P. navicularis. Perrotettianal A was isolated and has shown strong cytotoxicity against ovarian cancer.
BackgroundDifferent parts of the treeCalophyllum inophyllumL. (nuts, leaves, roots, bark, fruits,... more BackgroundDifferent parts of the treeCalophyllum inophyllumL. (nuts, leaves, roots, bark, fruits, nut oil and resin) are used as traditional medicines and cosmetics in most of the Pacific Islands. The oil efficiency as a natural cure and in traditional cosmetics has been largely described throughout the South Pacific, which led us to investigateC. inophyllum’s chemical and genetic diversity. A correlative study of the nut resin and leaf DNA from three distinct archipelagos in the South Pacific was carried out in order to identify diversity patterns inC. inophyllumacross the South Pacific.MethodsCalophyllum inophyllumplants were sampled from French Polynesia, New Caledonia and Fiji. We extracted tamanu oil (nut oil) resin for chemo-diversity studies and sampled leaf tissues for genetic studies. We applied an analysis method designed for small quantities (at a microscale level), and used High Performance Liquid Chromatography (HPLC) to establish the chemo-diversity of tamanu oil resin...
Lejeuneaceae is the largest family of liverworts in the world. Through the analyses of the chemic... more Lejeuneaceae is the largest family of liverworts in the world. Through the analyses of the chemical composition of some species, it has been demonstrated that they may represent an important source of original and bioactive molecules. None of the 146 species that occur in New Caledonia has been studied yet. Here we describe the terpenoid content of twelve New Caledonian species, including two endemics. We describe here, for the first time, the presence of frullanolide in the Lejeuneaceae, occurring as a major compound in the extract from Colura leratii, and a rarely observed santalene derivative from Acrolejeunea securifolia subsp. caledonica. These analyses also highlight species that probably contain original structures, such as Schiffneriolejeunea tumida var. hasskarliana, Cheilolejeunea spp and Thysananthus retusus. The results obtained here also confirm several previous hypotheses about the chemosystematics of the Lejeuneaceae. For example, lepidozene can be considered as a che...
Volatile components of seven Frullania species (Frullaniaceae) from New Caledonia, including five... more Volatile components of seven Frullania species (Frullaniaceae) from New Caledonia, including five endemic species ( F. bella, F. scalaris, F. mammillosa, F. cornuta and F. falsicornuta), were analyzed by GC-MS in order to index these plants to known chemotypes. Constituents detected in these Frullania species were mainly sesquiterpenes, as well as the bibenzyl dihydrognetin, and the flavonoid naringinin-5,7,4'-trimethyl ether. These compositions allowed an indexation of Frullania species from New Caledonia to cyclocolorenone, sesquiterpene lactone and bibenzyl chemotypes. In addition, qualitative intraspecies variations of chemical composition were very important and made indexation to known chemotypes very tricky. Moreover, two of the endemic liverworts did not possess any biomarker that linked to a known chemotype.
The aim of this study is to increase the phytochemical knowledge of South American bryophytes, pa... more The aim of this study is to increase the phytochemical knowledge of South American bryophytes, particularly from those of the southern tip of the continent, due to the uniqueness of its poorly known bryoflora. Thirty-two specimens were analyzed using GC-MS technique. Most of the molecules found in the present bryophyte species belong to sesquiterpenes. In general, liverworts resulted to be richer in terpenoid compounds, while mosses in n-alkanes. Oplopanone, trans- chrysanthenyl acetate and 6,7-secoeudesm-7(11)-en-6-al are compounds here newly reported to the bryophytes. α-Ylangene and α-herbertenol are new to hornworts, while α-herbertenol and n-heneicosane are new to mosses.
The leaf, wood and bark oils of three species of Myodocarpus, M. viellardii Brongn. & Gris, M. fr... more The leaf, wood and bark oils of three species of Myodocarpus, M. viellardii Brongn. & Gris, M. fraxinifolius Brongn. & Gris and M. lanceolatus Dubard & R. Viguier have been examined. From the wood oil of M. viellardii the major components were α-pinene (22.4%) and a monoterpene methyl ester, methyl myodocarpate (methyl 3,7-dimethylbicyclo [4,1,0]hept-3-ene-7-carboxylate) (61%), based on the δ-3-carene skeleton. Also present in lesser amounts was the corresponding acid, myodocarpic acid (3,7-dimethylbicyclo[4,1,0]hept-3-ene-7-carboxilic acid) and the corresponding alcohol, myodocarpol (3,7-dimethylbicyclo[4,1,0]hept-3-en-7-yl) methanol), in lesser (<3%) amounts. The bark oil contained β-caryophyllene (13.8%) and a series of long chain fatty alcohols, dodecanol, tetradecanol, hexadecanol, octadecanol and octadec-9-en-1-ol in amounts of 1.4–15% (all but octadecanol >11%). The leaf oil of this species produced a sesquiterpenic oil with the principal components being β-caryophyllen...
The New Caledonian endemic Treubia isignensis var. isignensis, which is known as a morphologicall... more The New Caledonian endemic Treubia isignensis var. isignensis, which is known as a morphologically primitive liverwort, was extracted with diethyl ether and the crude extract analyzed by TLC and GC/MS. The species is chemically very primitive because it produces only maaliane-, eudesmane-, aristolane and gorgonane sesquiterpene hydrocarbons, which are significant chemical marker of the species; neither oxygenated terpenoids nor aromatic compounds were detected.
The volatile components obtained by hydrodistillation of leaves of C. neocaledonica Dummer, C. su... more The volatile components obtained by hydrodistillation of leaves of C. neocaledonica Dummer, C. sulcata (Parlatore) Schlechter and N. pancheri (Carrière) de Laubenfels from New Caledonia were investigated for the first time by a combination of GC and GC–MS analysis, and compared with the heartwood oil compositions of the three species. The essential oils from C. sulcata and C. neocaledonica leaves contain a majority of monoterpenes while the leaf oil of N. pancheri is characterized by a high level of sesquiterpenoids. On the basis of the sesquiterpenoid composition of the wood- and leaf oils, N. pancheri is closely related to both New Caledonian Callitris spp. However, C. sulcata and C. neocaledonica oils remain distinct from N. pancheri and the Australian Callitris oils by the presence of compounds biosynthetically related to the bisabolyl cation, mainly barbatenes and thujopsene.
Analogs of glutamic acid were synthesized through the asymmetric Michael reaction using chiral ac... more Analogs of glutamic acid were synthesized through the asymmetric Michael reaction using chiral acyclic -enaminoesters and various Michael acceptors. The influence of the alkoxy group of the enaminoesters and also the nature of the olefins in the presence or not of zinc chloride on yield and enantioselectivity are explored.
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