Results 81 to 90 of about 155 (104)
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Convergent Synthesis of the C18-C30 Fragment of Amphidinol 3
Synlett, 2009The C18-C30 fragment of amphidinol 3 has been synthesized in a convergent fashion by employing two asymmetric Sharpless dihydroxylations, a Julia-Kocienski olefination and a Wittig reaction as the key steps.
Janine Cossy +5 more
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Tetrahedron, 2005
Amphidinols are a unique dinoflagellate metabolite with potent antifungal activity. We examined membrane permeabilizing action by amphidinol analogues with structural variations in polyhydroxy and polyene moieties. Consequently, the polyene and polyhydroxy moieties turned out to play important roles in binding to lipid bilayer membrane and in forming ...
Masayuki Satake +2 more
exaly +2 more sources
Amphidinols are a unique dinoflagellate metabolite with potent antifungal activity. We examined membrane permeabilizing action by amphidinol analogues with structural variations in polyhydroxy and polyene moieties. Consequently, the polyene and polyhydroxy moieties turned out to play important roles in binding to lipid bilayer membrane and in forming ...
Masayuki Satake +2 more
exaly +2 more sources
Stereoselective Synthesis of the C31−C40/C43−C52 Unit of Amphidinol 3
The Journal of Organic Chemistry, 2009A concise synthesis of a tetrahydropyran ring system corresponding to the C31-C40 and C43-C52 units of amphidinol 3 is described. Successive chemoselective reactions, i.e., cross-metathesis to differentiate the iodoolefin from the terminal olefin and Sharpless asymmetric dihydroxylation on the resulting E-olefin, resulted in expeditious synthesis of an
Mitsunori, Kanemoto +2 more
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Development of an Access Route to the C31−C52 Central Core of Amphidinol 3
Organic Letters, 2007[reaction: see text] An asymmetric synthesis of the heavily oxygenated inner sector of amphidinol 3 constituted of C31-C52 is described. The successful pathway highlights construction of the pair of identical tetrahydropyran subunits from a common intermediate.
Matthew W, Bedore +2 more
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Toxicon, 2007
The cytotoxicity of lingshuiol, a novel polyhydroxy compound with a linear carbon-chain isolated from the cultured marine dinoflagellate Amphidinium sp., and that of amphidinol 2 (AM2) was compared with hepatocytes. Both lingshuiol and AM2 were toxic to primary rat hepatocytes with IC(50) values of 0.21 and 6.4muM, respectively.
Xin-Ming, Qi +5 more
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The cytotoxicity of lingshuiol, a novel polyhydroxy compound with a linear carbon-chain isolated from the cultured marine dinoflagellate Amphidinium sp., and that of amphidinol 2 (AM2) was compared with hepatocytes. Both lingshuiol and AM2 were toxic to primary rat hepatocytes with IC(50) values of 0.21 and 6.4muM, respectively.
Xin-Ming, Qi +5 more
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Total Synthesis of Amphidinol 3
Journal of Synthetic Organic Chemistry, Japan, 2021Yuma Wakamiya, Tohru Oishi
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Diastereoselective synthesis of the C14–C29 fragment of amphidinol.
Organic & biomolecular chemistry, 2014An efficient stereoselective synthesis of the C14–C29 fragment highlighting a coupling reaction between a 1,3-dithiane derivative and an α-branched aldehyde was realized. This highly convergent synthesis involved two chiral pools, L-malic acid and (+)-camphorsulfonic acid, which are the starting compounds to control the six stereogenic centers present ...
Nicolas, Rival +5 more
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Structure and Biosynthesis of Amphidinol 17, a Hemolytic Compound from Amphidinium carterae
Journal of Natural Products, 2010Amphidinol 17 (AM17; 1), a novel amphidinol, has been isolated from a Bahamas strain of Amphidinium carterae. This new congener contains the signature hairpin region and a Delta(6) polyene arm, whereas the polyol arm is distinct from those of other amphidinols.
Yanhui, Meng +4 more
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Algal amphidinols, an alternative to sulfites in the fight against Brettanomyces bruxellensis
LWT - Food Science and TechnologyThis study evaluated the biocidal activity of a microalgal extract from Amphidinium carterae under oenological conditions to limit Brettanomyces bruxellensis development in red wines over 150 days. Viable and culturable cell concentrations were analyzed during this period.
Abry, Chloé +5 more
exaly +2 more sources
Membrane permeabilizing action of amphidinol 3 and theonellamide A in raft-forming lipid mixtures
Zeitschrift für Naturforschung C, 2016Abstract Amphidinol 3 (AM3) and theonellamide A (TNM-A) are potent antifungal compounds produced by the dinoflagellate Amphidinium klebsii and the sponge Theonella spp., respectively. Both of these metabolites have been demonstrated to interact with membrane lipids ultimately resulting in a compromised bilayer integrity.
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