Relevant bibliographies by topics / Amphidinols

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Academic literature on the topic 'Amphidinols'

Author: Grafiati
Published: 25 May 2024

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Journal articles on the topic "Amphidinols"

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Molina-Miras, Alejandro, Alejandro Bueso-Sánchez, María del Carmen Cerón-García, Asterio Sánchez-Mirón, Antonio Contreras-Gómez, and Francisco García-Camacho. "Effect of Nitrogen, Phosphorous, and Light Colimitation on Amphidinol Production and Growth in the Marine Dinoflagellate Microalga Amphidinium carterae." Toxins 14, no. 9 (August 28, 2022): 594. http://dx.doi.org/10.3390/toxins14090594.

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The marine dinoflagellate microalga Amphidinium carterae is a source of amphidinols, a fascinating group of polyketide metabolites potentially useful in drug design. However, Amphidinium carterae grows slowly and produces these toxins in tiny amounts, representing a hurdle for large-scale production. Understanding dinoflagellate growth kinetics under different photobioreactor conditions is imperative for promoting the successful implementation of a full-scale integrated bioproduct production system. This study evaluates the feasibility of growing Amphidinium carterae under different ranges of nitrogen concentration (NO3− = 882–2646 µM), phosphorus concentration (PO33− = 181–529 µM), and light intensity (Y0 = 286–573 µE m−2 s−1) to produce amphidinols. A mathematical colimitation kinetic model based on the “cell quota” concept is developed to predict both algal growth and nutrient drawdown, assuming that all three variables (nitrogen, phosphorous and light) can simultaneously colimit microalgal growth. The model was applied to the semicontinuous culture of the marine microalgae Amphidinium carterae in an indoor LED-lit raceway photobioreactor. The results show that both growth and amphidinol production strongly depend on nutrient concentrations and light intensity. Nonetheless, it was possible to increase Amphidinium carterae growth while simultaneously promoting the overproduction of amphidinols. The proposed model adequately describes Amphidinium carterae growth, nitrate and phosphate concentrations, and intracellular nitrogen and phosphorus storage, and has therefore the potential to be extended to other systems used in dinoflagellate cultivation and the production of bioproducts obtained therein.
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Orefice, Ida, Sergio Balzano, Giovanna Romano, and Angela Sardo. "Amphidinium spp. as a Source of Antimicrobial, Antifungal, and Anticancer Compounds." Life 13, no. 11 (November 4, 2023): 2164. http://dx.doi.org/10.3390/life13112164.

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Dinoflagellates make up the second largest marine group of marine unicellular eukaryotes in the world ocean and comprise both heterotrophic and autotrophic species, encompassing a wide genetic and chemical diversity. They produce a plethora of secondary metabolites that can be toxic to other species and are mainly used against predators and competing species. Dinoflagellates are indeed often responsible for harmful algal bloom, where their toxic secondary metabolites can accumulate along the food chain, leading to significant damages to the ecosystem and human health. Secondary metabolites from dinoflagellates have been widely investigated for potential biomedical applications and have revealed multiple antimicrobial, antifungal, and anticancer properties. Species from the genus Amphidinium seem to be particularly interesting for the production of medically relevant compounds. The present review aims at summarising current knowledge on the diversity and the pharmaceutical properties of secondary metabolites from the genus Amphidinium. Specifically, Amphidinium spp. produce a range of polyketides possessing cytotoxic activities such as amphidinolides, caribenolides, amphidinins, and amphidinols. Potent antimicrobial properties against antibiotic-resistant bacterial strains have been observed for several amphidinins. Amphidinols revealed instead strong activities against infectious fungi such as Candida albicans and Aspergillus fumigatus. Finally, compounds such as amphidinolides, isocaribenolide-I, and chlorohydrin 2 revealed potent cytotoxic activities against different cancer cell lines. Overall, the wide variety of antimicrobial, antifungal, and anticancer properties of secondary metabolites from Amphidinium spp. make this genus a highly suitable candidate for future medical applications, spanning from cancer drugs to antimicrobial products that are alternatives to currently available antibiotic and antimycotic products.
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Martínez, Kevin A., Chiara Lauritano, Dana Druka, Giovanna Romano, Teresa Grohmann, Marcel Jaspars, Jesús Martín, et al. "Amphidinol 22, a New Cytotoxic and Antifungal Amphidinol from the Dinoflagellate Amphidinium carterae." Marine Drugs 17, no. 7 (June 27, 2019): 385. http://dx.doi.org/10.3390/md17070385.

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Due to the unique biodiversity and the physical-chemical properties of their environment, marine microorganisms have evolved defense and signaling compounds that often have no equivalent in terrestrial habitats. The aim of this study was to screen extracts of the dinoflagellate Amphidinium carterae for possible bioactivities (i.e., anticancer, anti-inflammatory, anti-diabetes, antibacterial and antifungal properties) and identify bioactive compounds. Anticancer activity was evaluated on human lung adenocarcinoma (A549), human skin melanoma (A2058), human hepatocellular carcinoma (HepG2), human breast adenocarcinoma (MCF7) and human pancreas carcinoma (MiaPaca-2) cell lines. Antimicrobial activities were evaluated against Gram-positive bacteria (Staphylococcus aureus MRSA and MSSA), Gram-negative bacteria (i.e., Escherichia coli and Klebsiella pneumoniae), Mycobacterium tuberculosis and the fungus Aspergillus fumigatus. The results indicated moderate biological activities against all the cancer cells lines and microorganisms tested. Bioassay-guided fractionation assisted by HRMS analysis allowed the detection of one new and two known amphidinols that are potentially responsible for the antifungal and cytotoxic activities observed. Further isolation, purification and structural elucidation led to a new amphidinol, named amphidinol 22. The planar structure of the new compound was determined by analysis of its HRMS and 1D and 2D NMR spectra. Its biological activity was evaluated, and it displayed both anticancer and antifungal activities.
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Wellkamp, Marvin, Francisco García-Camacho, Lorena M. Durán-Riveroll, Jan Tebben, Urban Tillmann, and Bernd Krock. "LC-MS/MS Method Development for the Discovery and Identification of Amphidinols Produced by Amphidinium." Marine Drugs 18, no. 10 (September 29, 2020): 497. http://dx.doi.org/10.3390/md18100497.

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Amphidinols are polyketides produced by dinoflagellates suspected of causing fish kills. Here, we demonstrate a liquid chromatography-tandem mass spectrometry (LC-MS/MS) method for the identification and quantification of amphidinols (AM). Novel AM were detected by neutral loss (NL) scan and then quantified together with known AM by selection reaction monitoring (SRM). With the new method, AM were detected in four of eight analyzed strains with a maximum of 3680 fg toxin content per cell. In total, sixteen novel AM were detected by NL scan and characterized via their fragmentation patterns. Of these, two substances are glycosylated forms. This is the first detection of glycosylated AM.
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Morsy, Nagy, Keiichi Konoki, Toshihiro Houdai, Nobuaki Matsumori, Tohru Oishi, Michio Murata, and Saburo Aimoto. "Roles of integral protein in membrane permeabilization by amphidinols." Biochimica et Biophysica Acta (BBA) - Biomembranes 1778, no. 6 (June 2008): 1453–59. http://dx.doi.org/10.1016/j.bbamem.2008.01.018.

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Cossy, Janine, Tomoki Tsuchiya, Laurent Ferrié, Sébastien Reymond, Thomas Kreuzer, Françoise Colobert, Pierre Jourdain, and István Markó. "Efficient Syntheses of the Polyene Fragments Present in Amphidinols." Synlett 2007, no. 14 (July 20, 2007): 2286–88. http://dx.doi.org/10.1055/s-2007-984910.

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Morsy, Nagy, Toshihiro Houdai, Keiichi Konoki, Nobuaki Matsumori, Tohru Oishi, and Michio Murata. "Effects of lipid constituents on membrane-permeabilizing activity of amphidinols." Bioorganic & Medicinal Chemistry 16, no. 6 (March 15, 2008): 3084–90. http://dx.doi.org/10.1016/j.bmc.2007.12.029.

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Durán-Riveroll, Lorena M., Jannik Weber, and Bernd Krock. "First Identification of Amphidinols from Mexican Strains and New Analogs." Toxins 15, no. 2 (February 16, 2023): 163. http://dx.doi.org/10.3390/toxins15020163.

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The genus Amphidinium has been the subject of recent attention due to the production of polyketide metabolites. Some of these compounds have shown significant bioactivities and could be related to species interactions in the natural benthic microenvironment. Among these compounds, amphidinols (AMs) are suspected to be related to fish kills and probably implicated in ciguatera symptoms associated with the occurrence of benthic harmful algal blooms (bHABs). Here, we present the first report of a variety of AMs produced by cultured strains from several species from the Mexican Pacific, the Gulf of California, and the Gulf of Mexico. Through ultra-high performance liquid chromatography coupled with tandem mass spectrometry (UHPLC-MS/MS), ten previously known AMs (AM02, -04, -05, -06, -07, -09, -11, -14, -15, and -17), four recently reported AMs (N7, N8/N9, N12, and N13), and three new variants (U1, U2, and U3) were identified. Of the twelve analyzed Amphidinium cultures, five were not AM producers, and the cell quotas of the remaining seven strains ranged from close to nondetectable to a maximum of 1694 fg cell−1, with many intermediate levels in between. The cultures from the Mexican North Pacific coast produced AMs in a higher quantity and variety than those from worldwide locations. This is the first study of AMs from Mexican Amphidinium strains, and our results confirm the relevance of continuing the investigation of the genus bioactive metabolites.
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Houdai, Toshihiro, Shigeru Matsuoka, Nagy Morsy, Nobuaki Matsumori, Masayuki Satake, and Michio Murata. "Hairpin conformation of amphidinols possibly accounting for potent membrane permeabilizing activities." Tetrahedron 61, no. 11 (March 2005): 2795–802. http://dx.doi.org/10.1016/j.tet.2005.01.069.

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Houdai, Toshihiro, Shigeru Matsuoka, Michio Murata, Masayuki Satake, Sayo Ota, Yasukatsu Oshima, and Lesley L. Rhodes. "Acetate labeling patterns of dinoflagellate polyketides, amphidinols 2, 3 and 4." Tetrahedron 57, no. 26 (June 2001): 5551–55. http://dx.doi.org/10.1016/s0040-4020(01)00481-1.

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Dissertations / Theses on the topic "Amphidinols"

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Peltekis, Alexandra. "Le plaste des diatomées : centre énergétique et cible des interactions allélopathiques." Electronic Thesis or Diss., Sorbonne université, 2020. https://accesdistant.sorbonne-universite.fr/login?url=https://theses-intra.sorbonne-universite.fr/2020SORUS174.pdf.

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Une des principales forces qui façonnent la dynamique et la structure des communautés phytoplanctoniques est l'inhibition directe du métabolisme des concurrents grâce à l'utilisation de métabolites secondaires. Mais notre compréhension de ce phénomène, appelé allélopathie, reste limitée. La photosynthèse est une sonde idéale pour étudier les interactions allélopathiques entre microalgues marines, car elle en est une des cibles principales. Nous avons validé une approche nouvelle, permettant de disséquer les activités photosynthétiques de chaque microalgue au sein d’un mélange, permettant de dévoiler des interactions allélopathiques ciblant la photosynthèse. Cette thèse se concentre sur le plaste des diatomées, qui, au-delà d’être le centre énergétique de la cellule, s’avèrent aussi être la cible des composés allélochimiques libérés par leurs compétiteurs. Cette approche méthodologique a permis de montrer l’inhibition de l’activité photosynthétique de la diatomée T. pseudonana par des composés allélochimiques libérés par le dinoflagellé A. carterae. Cette inhibition implique la dissipation du gradient électrochimique de proton généré à travers les thylacoïdes, probablement par des molécules de type amphidinols formant des pores sur les membranes biologiques. Au cours de deux collaborations, nous avons montré deux autres interactions allélopathiques ciblant le plaste des diatomées : le rôle des quinolones libérées par des bactéries, sur les chaînes de transport d’électron photosynthétique et respiratoire de la diatomée P. tricornutum, les effets du filtrat du dinoflagellé A. minutum sur les membranes cytoplasmiques et chloroplastiques de la diatomée C. muelleri
One of the major forces that shape the dynamics and structure of phytoplankton communities is the direct inhibition of the metabolism of competitors thanks to the use of secondary metabolites. But our understanding of this phenomenon, called allelopathy, remains limited. Photosynthesis is an ideal probe to study allelopathic interactions between marine microalgae, simply because it is one of the main targets. We have validated a new approach allowing to dissect the photosynthetic activities of each microalgae within a mixture, allowing to reveal allelopathic interactions affecting photosynthesis. This thesis focuses on diatoms plastid which, beyond being the energetic center of the cell, also proves to be a specific target of the allelochemical compounds released by their competitors.This methodological approach made it possible to demonstrate the inhibition of the photosynthetic activity of the diatom T. pseudonana by allelochemical compounds released by the dinoflagellate A. carterae. This inhibition involves the dissipation of the electrochemical proton gradient across the thylakoids, probably by amphidinol-like molecules forming pores on biological membranes. We were also able to show two other allelopathic interactions targeting the plastid of diatoms: the role of alkyl-quinolones, released by bacteria, on the photosynthetic and respiratory electron transport chains of the diatom P. tricornutum, and the effects of the filtrate of the dinoflagellate A. minutum on the cytoplasmic and plastid membranes of the diatom C. muelleri
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Chang, Shuh-Kuen. "Studies toward the total synthesis of amphidinol 3." Columbus, Ohio : Ohio State University, 2006. http://rave.ohiolink.edu/etdc/view?acc%5Fnum=osu1150261354.

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Liesener, Florian Peter. "Studien zur Totalsynthese von Amphidinolid H2." [S.l.] : [s.n.], 2006. http://deposit.ddb.de/cgi-bin/dokserv?idn=979900492.

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Jannsen, Ulrike. "Studien zur Totalsynthese von Amphidinolid H2." [S.l.] : [s.n.], 2006. http://deposit.ddb.de/cgi-bin/dokserv?idn=982609957.

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Bedore, Matthew William. "Synthesis of Key Fragments Contained in the Framework of Amphidinol 3." The Ohio State University, 2008. http://rave.ohiolink.edu/etdc/view?acc_num=osu1211485773.

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Karumudi, B. "Synthetic studies toward eupomatilone-6, 4-O-β-D-galactosyl maltose and amphidinol-3." Thesis(Ph.D.), CSIR-National Chemical Laboratory, Pune, 2008. http://dspace.ncl.res.in:8080/xmlui/handle/20.500.12252/2661.

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Grisin, Aleksandr. "Diastereoselective synthesis of syn-1,3-polyols and studies towards the C1-C31 and C32-C52 fragments of amphidinol 3." Thesis, University of Liverpool, 2012. http://livrepository.liverpool.ac.uk/10373/.

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Diastereoselective Synthesis of syn-1,3-Polyols The stereoselective construction of polyacetate 1,3-diols has attracted considerable attention due to the ubiquity of this motif in complex biologically active polyene macrolides (amphotericin B, RK-397, mycoticin, candidin). We have developed a highly stereoselective bismuth(III)-mediated two-component hemiacetal/oxa-conjugate addition reaction, which directly provides syn-1,3-diols in the form of cyclic acetals having an adjacent electron-withdrawing group in the form of aldehydes and ketones. The scope and limitations of this transformation were examined and culminated with the synthesis of the C18-C28 fragment of antibiotic RK-397. Studies towards the C1-C31 and C32-C52 Fragments of Amphidinol 3 Temporary-tethered reactions provide an important strategy for target- directed synthesis, since they circumvent the problems encountered with entropically unfavorable reactions. The temporary silicon-tethered ring-closing metathesis (TST- RCM) allows for the highly (Z)-selective coupling of mixed silaketals in the formation of the medium sized rings. The latter compounds can undergo a substrate controlled stereoselective electrophilic functionalisation, for example, hydroboration, dihydroxylation or epoxidation, and produce polyoxygenated motifs that are present in many biologically important natural products. In the course of these studies we have developed a highly convergent asymmetric synthesis of the C1-C31 polyol fragment of amphidinol 3, where the TST-RCM/hydroboration reaction is successfully employed for the efficient coupling ii of the C16-C23 and C24-C30 units of the natural product with concomitant introduction of the crucial propionate-type C23-C24 stereocentres. In the final part of thesis the investigation of the stereoselective dihydroxylation reaction of mixed syn and anti eight-membered cyclic silaketals was carried out. The resulting oxygenated products can be efficiently transformed via an intramolecular cyclisation of δ-hydroxy epoxides into the highly substituted syn- and anti-tetrahydropyrans (THPs), a strategy that could also have application in related natural products, for example, ladder polyether polyketides. The merit of the developed methodology was highlighted in the asymmetric synthesis of the common C31(52)-C39(44) THP fragment of amphidinol 3, which could be ultimately used in the bidirectional route towards the bis-THP segment of the natural product.
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Cusak, Alen. "Temporary silicon-tethered ring-closing metathesis approach to polyketide fragments : Asymmetric synthesis of the C1-C30 fragments of amphidinol 3." Thesis, University of Liverpool, 2009. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.511068.

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Ferrié, Laurent. "Developpement de métathèses d'oléfines chimiosélectives : application à la synthèse de produits naturels biologiquement actifs." Paris 6, 2008. http://www.theses.fr/2008PA066043.

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Durant la dernière décennie, la métathèse d’oléfines catalysée par les métaux de transition est devenue l’une des plus puissantes transformations organométalliques, permettant la formation de liaisons carbone-carbone en synthèse organique. En particulier, les réactions de fermeture de cycle par métathèse ou de métathèse croisée ont été très largement étudiées. Grâce au développement de catalyseurs robustes au ruthénium par Grubbs et al. , la métathèse est devenue un puissant outil dans la synthèse totale de produits naturels biologiquement actifs. En particulier les macrolactones, que l’ont peut synthétiser par création d’une liaison C-O ou d’une liaison C-C, sont un type de produit naturel biologiquement actif souvent rencontré dans la nature. Les synthèses de la spongidepsine, du leucascandrolide A et du collétodiol ont été réalisées en utilisant des réactions de métathèse d’oléfine comme étape-clé, ce qui a permis d’accéder facilement et rapidement à ces macrolactones. Le développement de métathèses d’oléfine chimiosélectives entre des 1,3-diènes et des oléfines partenaires a pu un donner un accès rapide à des diènes fonctionnalisés. Il a été montré en particulier que les réactions utilisant les diènamides étaient plus chimiosélectives que les esters dièniques. Cette réaction chimiosélective a été utilisé dans la synthèse du fragment polyènique de l’amphidinol. De même, ce type de réaction a pu conduire rapidement à la synthèse d’α-hydroxybutyrolactones, comme la muricatacine ou l’iso-cladospolide B. Les métathèses d’oléfines utilisant des diènamides se révèlent être alors une méthode de choix dans la synthèse de produits naturels contenant des motifs polyèniques.
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Jannsen, Ulrike [Verfasser]. "Studien zur Totalsynthese von Amphidinolid H2 / von Ulrike Jannsen." 2006. http://d-nb.info/982609957/34.

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