The syntheses of three highly unsaturated marine lipid hydrocarbons

Holmeide, Anne Kristin; Skattebøl, Lars; Sydnes, Magne O.

doi:10.1039/b101889m

Cited by 26 publications

(15 citation statements)

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“…Spectral data were in agreement with those previously reported [17]. (13) was prepared by reduction of 9 with NaBH 4 according to the literature [20]. (10).…”

Section: E6z9z12z15z-octadecapentaenal (9)supporting

confidence: 81%

“…The vinyl ketone 1 attracted our interest as part of an ongoing project utilizing the polyunsaturated fatty acids eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) as starting materials for the OPEN ACCESS syntheses of compounds containing several methylene interrupted Z double bonds [3][4][5][6][7][8][9][10][11][12][13][14][15][16][17]. A key reaction in this respect is the oxidative degradation of EPA and DHA to aldehydes by way of the corresponding iodolactones.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of All-Z-1,6,9,12,15-Octadecapenten-3-one, A Vinyl Ketone Polyunsaturated Marine Natural Product Isolated from Callysponga sp.

2014

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“…Spectral data were in agreement with those previously reported [17]. (13) was prepared by reduction of 9 with NaBH 4 according to the literature [20]. (10).…”

Section: E6z9z12z15z-octadecapentaenal (9)supporting

confidence: 81%

Section: Introductionmentioning

confidence: 99%

Synthesis of All-Z-1,6,9,12,15-Octadecapenten-3-one, A Vinyl Ketone Polyunsaturated Marine Natural Product Isolated from Callysponga sp.

2014

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“…Metabolites 923-926, found in Japanese populations of L. okamurai [192,204,779,780], are considered to be biosynthetic precursors of various C 15 non-terpenoid metabolites found in Laurencia species. Their synthesis was reported by the Yamada group in 1981 and 1986 [204,780], while another synthesis of laurencenyne (926) and its (E)-isomer 925 was later achieved by Holmeide et al starting from eicosapentaenoic acid [781]. A Japanese L. nipponica population afforded a mixture of optical isomers ((6R,7R) and (6S,7S)) of (E)-(942) and (Z)-laurediol (943), along with their diacetates 945 and 946, respectively [738].…”

Section: Linear Acetogeninsmentioning

confidence: 96%

The Laurencia Paradox: An Endless Source of Chemodiversity

Harizani

Iοannou

Roussis

2016

Progress in the Chemistry of Organic Natural Products

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Nature, the most prolific source of biological and chemical diversity, has provided mankind with treatments for health problems since ancient times and continues to be the most promising reservoir of bioactive chemicals for the development of modern drugs. In addition to the terrestrial organisms that still remain a promising source of new bioactive metabolites, the marine environment, covering approximately 70% of the Earth's surface and containing a largely unexplored biodiversity, offers an enormous resource for the discovery of novel compounds. According to the MarinLit database, more than 27,000 metabolites from marine macro- and microorganisms have been isolated to date providing material and key structures for the development of new products in the pharmaceutical, food, cosmeceutical, chemical, and agrochemical sectors. Algae, which thrive in the euphotic zone, were among the first marine organisms that were investigated as sources of food, nutritional supplements, soil fertilizers, and bioactive metabolites.Red algae of the genus Laurencia are accepted unanimously as one of the richest sources of new secondary metabolites. Their cosmopolitan distribution, along with the chemical variation influenced to a significant degree by environmental and genetic factors, have resulted in an endless parade of metabolites, often featuring multiple halogenation sites.The present contribution, covering the literature until August 2015, offers a comprehensive view of the chemical wealth and the taxonomic problems currently impeding chemical and biological investigations of the genus Laurencia. Since mollusks feeding on Laurencia are, in many cases, bioaccumulating, and utilize algal metabolites as chemical weaponry against natural enemies, metabolites of postulated dietary origin of sea hares that feed on Laurencia species are also included in the present review. Altogether, 1047 secondary metabolites, often featuring new carbocyclic skeletons, have been included.The chapter addresses: (1) the "Laurencia complex", the botanical description and the growth and population dynamics of the genus, as well as its chemical diversity and ecological relations; (2) the secondary metabolites, which are organized according to their chemical structures and are classified into sesquiterpenes, diterpenes, triterpenes, acetogenins, indoles, aromatic compounds, steroids, and miscellaneous compounds, as well as their sources of isolation which are depicted in tabulated form, and (3) the biological activity organized according to the biological target and the ecological functions of Laurencia metabolites.

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“…Inhibitors 1 and 2 were identified as (6Z,9Z,12Z,15Z)-1,6,9,12,15-henicosapentaene 15 (HEP, Figure 1) and (6Z,9Z,12Z,15Z,18Z)--1,6,9,12,15,18-henicosahexaene 14 (HEH, Figure 1), respectively, by their spectral data, 16 compared with the literature data. [17][18][19][20] Stereostructures of double bonds of 1 and 2 were deduced to be all Z configurations from the 13 C NMR data (δ 25.63-25.64 for 1; δ 25.52-25.64 for 2) for the allylic positions in 1,4-pentadiene moieties of them. Pfeffer et al 21 reported that the 13 C NMR data of δ 25.7, 30.5, and 35.7 for the allylic positions in 1,4-pentadiene moieties of polyunsaturated fatty acid residues were assigned as Z,Z-, Z,E-, and E,E-isomers, respectively.…”

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confidence: 99%

Lipoxygenase inhibitors derived from marine macroalgae

Kurihara

Kagawa

Konno

et al. 2014

Bioorganic & Medicinal Chemistry Letters

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The solvent extracts from the algae Sargassum thunbergii (Sargassaceae) and Odonthalia corymbifera (Rhodomelaceae) were subjected to soybean lipoxygenase inhibitory screening. Two hydrophobic inhibitors were obtained from the extracts of S. thunbergii through inhibitory assay-guided fractionation. The inhibitors were identified as known exo-methylenic alkapolyenes (6Z,9Z,12Z,15Z)-1,6,9,12,15-henicosapentaene (1) and (6Z,9Z,12Z,15Z,18Z)- 1,6,9,12,15,18-henicosahexaene (2). The alkapolyenes 1 and 2 showed higher inhibitory activity than the known inhibitor nordihydroguaiaretic acid (NDGA). Pheophytin a (3) was obtained from the extract of O.corymbifera. The inhibitor 3 also showed higher inhibitory activity than NDGA. This is the first report on lipoxygenase inhibition of exo-methylenic alkapolyenes and a chlorophyll a-related substance. Many studies have been carried out on highly unsaturated fatty acids, leukotrienes, and LOX activity originated from macroalgae, 6-9 whereas a few studies were performed on LOX inhibitors. 10,11 During our screening of enzyme inhibitors derived from algal extracts, we disclosed potent LOX inhibitory activity of the extracts from the brown alga Sargassum thunbergii and the red alga Odonthalia corymbifera. In the present study, we isolated two exo-methylenic alkapolyenes from S. thunbergii and a chlorophyll a-related substance from O. corymbifera.S. thunbergii (2.85 kg, air-dried) was collected at the coast of Otobe, south-western Hokkaido, Japan. Fresh alga washed with tap water was extracted with MeOH-water (9:1, v/v) for a week. LOX inhibitory activity was assayed by a modified absorptiometry method 12-14 for the extract and at a series of separation steps. An ethyl acetate-soluble fraction (8.46 g) partitioned from the extract (69.5 g) was chromatographed on silica gel column with hexane-EtOAc (3:1, v/v) as eluent. Further chromatography was employed on silica gel column with n-hexane-EtOAc (19:1, v/v). The active fraction was twice separated on preparative thin-layer chromatography with n-hexane-EtOAc (3:1, v/v) and 100% hexane as developing solvent to afford inhibitors 1 (7.9 mg, 2.8 ppm yield) and 2 (2.8 mg, 1.1 ppm yield). Inhibitors 1 and 2were identified as (6Z,9Z,12Z,15Z)-1,6,9,12,15-henicosapentaene 15 (HEP, Figure 1) and (6Z,9Z,12Z,15Z,18Z)--1,6,9,12,15,18-henicosahexaene 14 (HEH, Figure 1), respectively, by their spectral data, 16 compared with the literature data. [17][18][19][20] Stereostructures of double bonds of 1 and 2 were deduced to be all Z configurations from the 13 C NMR data (δ 25.63-25.64 for 1; δ 25.52-25.64 for 2) for the allylic positions in 1,4-pentadiene moieties of them. Pfeffer et al. 21 reported that the 13 C NMR data of δ 25.7, 30.5, and 35.7 for the allylic positions in 1,4-pentadiene moieties of polyunsaturated fatty acid residues were assigned as Z,Z-, Z,E-, and E,E-isomers, respectively. HEP (1) and HEH (2) inhibited soybean LOX in concentration-dependent manners (Figure 2). The IC 50 values of 1 and 2 were calculated 40 µM and 5...

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The syntheses of three highly unsaturated marine lipid hydrocarbons

Cited by 26 publications

References 9 publications

Synthesis of All-Z-1,6,9,12,15-Octadecapenten-3-one, A Vinyl Ketone Polyunsaturated Marine Natural Product Isolated from Callysponga sp.

Synthesis of All-Z-1,6,9,12,15-Octadecapenten-3-one, A Vinyl Ketone Polyunsaturated Marine Natural Product Isolated from Callysponga sp.

The Laurencia Paradox: An Endless Source of Chemodiversity

Lipoxygenase inhibitors derived from marine macroalgae

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