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Journal articles on the topic 'Amphidinols'

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Author: Grafiati

Published: 25 May 2024

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1

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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2

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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3

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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4

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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5

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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6

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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7

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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8

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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9

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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10

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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11

Morsy, Nagy, Toshihiro Houdai, Shigeru Matsuoka, Nobuaki Matsumori, Seiji Adachi, Tohru Oishi, Michio Murata, Takashi Iwashita, and Tsuyoshi Fujita. "Structures of new amphidinols with truncated polyhydroxyl chain and their membrane-permeabilizing activities." Bioorganic & Medicinal Chemistry 14, no. 19 (October 2006): 6548–54. http://dx.doi.org/10.1016/j.bmc.2006.06.012.

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12

López-Rodríguez, Mercedes, Lorenzo López-Rosales, Giullia Diletta, María del Carmen Cerón-García, Elvira Navarro-López, Juan José Gallardo-Rodríguez, Ana Isabel Tristán, Ana Cristina Abreu, and Francisco García-Camacho. "The Isolation of Specialty Compounds from Amphidinium carterae Biomass by Two-Step Solid-Phase and Liquid-Liquid Extraction." Toxins 14, no. 9 (August 28, 2022): 593. http://dx.doi.org/10.3390/toxins14090593.

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The two main methods for partitioning crude methanolic extract from Amphidinium carterae biomass were compared. The objective was to obtain three enriched fractions containing amphidinols (APDs), carotenoids, and fatty acids. Since the most valuable bioproducts are APDs, their recovery was the principal goal. The first method consisted of a solid-phase extraction (SPE) in reverse phase that, for the first time, was optimized to fractionate organic methanolic extracts from Amphidinium carterae biomass using reverse-phase C18 as the adsorbent. The second method consisted of a two-step liquid-liquid extraction coupled with SPE and, alternatively, with solvent partitioning. The SPE method allowed the recovery of the biologically-active fraction (containing the APDs) by eluting with methanol (MeOH): water (H2O) (80:20 v/v). Alternatively, an APD purification strategy using solvent partitioning proved to be a better approach for providing APDs in a clear-cut way. When using n-butanol, APDs were obtained at a 70% concentration (w/w), whereas for the SPE method, the most concentrated fraction was only 18% (w/w). For the other fractions (carotenoids and fatty acids), a two-step liquid-liquid extraction (LLE) method coupled with the solvent partitioning method presented the best results.

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13

Yang, Xiao, Zhi Yan, Jingjing Chen, Derui Wang, and Ke Li. "Acute Toxicity of the Dinoflagellate Amphidinium carterae on Early Life Stages of Zebrafish (Danio rerio)." Toxics 11, no. 4 (April 13, 2023): 370. http://dx.doi.org/10.3390/toxics11040370.

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Dinoflagellates of the genus Amphidinium can produce a variety of polyketides, such as amphidinols (AMs), amphidinoketides, and amphidinin, that have hemolytic, cytotoxic, and fish mortality properties. AMs pose a significant threat to ecological function due to their membrane-disrupting and permeabilizing properties, as well as their hydrophobicity. Our research aims to investigate the disparate distribution of AMs between intracellular and extracellular environments, as well as the threat that AMs pose to aquatic organisms. As a result, AMs containing sulphate groups such as AM19 with lower bioactivity comprised the majority of A. carterae strain GY-H35, while AMs without sulphate groups such as AM18 with higher bioactivity displayed a higher proportion and hemolytic activity in the extracellular environment, suggesting that AMs may serve as allelochemicals. When the concentration of extracellular crude extracts of AMs reached 0.81 µg/mL in the solution, significant differences in zebrafish embryonic mortality and malformation were observed. Over 96 hpf, 0.25 μL/mL of AMs could cause significant pericardial edema, heart rate decrease, pectoral fin deformation, and spinal deformation in zebrafish larvae. Our findings emphasized the necessity of conducting systematic research on the differences between the intracellular and extracellular distribution of toxins to gain a more accurate understanding of their effects on humans and the environment.

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14

Molina-Miras, A., A. Morales-Amador, C. R. de Vera, L. López-Rosales, A. Sánchez-Mirón, M. L. Souto, J. J. Fernández, M. Norte, F. García-Camacho, and E. Molina-Grima. "A pilot-scale bioprocess to produce amphidinols from the marine microalga Amphidinium carterae: Isolation of a novel analogue." Algal Research 31 (April 2018): 87–98. http://dx.doi.org/10.1016/j.algal.2018.01.010.

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15

Cutignano, Adele, Genoveffa Nuzzo, Angela Sardo, and Angelo Fontana. "The Missing Piece in Biosynthesis of Amphidinols: First Evidence of Glycolate as a Starter Unit in New Polyketides from Amphidinium carterae." Marine Drugs 15, no. 6 (May 31, 2017): 157. http://dx.doi.org/10.3390/md15060157.

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16

Abreu, Ana Cristina, Alejandro Molina-Miras, Luis M. Aguilera-Sáez, Lorenzo López-Rosales, María del Carmen Cerón-García, Asterio Sánchez-Mirón, Lucía Olmo-García, et al. "Production of Amphidinols and Other Bioproducts of Interest by the Marine Microalga Amphidinium carterae Unraveled by Nuclear Magnetic Resonance Metabolomics Approach Coupled to Multivariate Data Analysis." Journal of Agricultural and Food Chemistry 67, no. 34 (August 15, 2019): 9667–82. http://dx.doi.org/10.1021/acs.jafc.9b02821.

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17

Morales-Amador, Adrián, Alejandro Molina-Miras, Lorenzo López-Rosales, Asterio Sánchez-Mirón, Francisco García-Camacho, María L. Souto, and José J. Fernández. "Isolation and Structural Elucidation of New Amphidinol Analogues from Amphidinium carterae Cultivated in a Pilot-Scale Photobioreactor." Marine Drugs 19, no. 8 (July 29, 2021): 432. http://dx.doi.org/10.3390/md19080432.

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The demand for valuable products from dinoflagellate biotechnology has increased remarkably in recent years due to their many prospective applications. However, there remain many challenges that need to be addressed in order to make dinoflagellate bioactives a commercial reality. In this article, we describe the technical feasibility of producing and recovering amphidinol analogues (AMs) excreted into a culture broth of Amphidinium carterae ACRN03, successfully cultured in an LED-illuminated pilot-scale (80 L) bubble column photobioreactor operated in fed-batch mode with a pulse feeding strategy. We report on the isolation of new structurally related AMs, amphidinol 24 (1, AM24), amphidinol 25 (2, AM25) and amphidinol 26 (3, AM26), from a singular fraction resulting from the downstream processing. Their planar structures were elucidated by extensive NMR and HRMS analysis, whereas the relative configuration of the C-32→C-47 bis-tetrahydropyran core was confirmed to be antipodal in accord with the recently revised configuration of AM3. The hemolytic activities of the new metabolites and other related derivatives were evaluated, and structure–activity conclusions were established. Their isolation was based on a straightforward and high-performance bioprocess that could be suitable for the commercial development of AMs or other high-value compounds from shear sensitive dinoflagellates.

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18

Grisin, Aleksandr, and P. Andrew Evans. "A highly convergent synthesis of the C1–C31 polyol domain of amphidinol 3 featuring a TST-RCM reaction: confirmation of the revised relative stereochemistry." Chemical Science 6, no. 11 (2015): 6407–12. http://dx.doi.org/10.1039/c5sc00814j.

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19

Wakamiya, Yuma, and Tohru Oishi. "Total Synthesis of Amphidinol 3." Journal of Synthetic Organic Chemistry, Japan 79, no. 7 (July 1, 2021): 664–72. http://dx.doi.org/10.5059/yukigoseikyokaishi.79.664.

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20

Haq, Saddef, Benjamin L. Oyler, Ernest Williams, Mohd M. Khan, David R. Goodlett, Tsvetan Bachvaroff, and Allen R. Place. "Investigating A Multi-Domain Polyketide Synthase in Amphidinium carterae." Marine Drugs 21, no. 8 (July 27, 2023): 425. http://dx.doi.org/10.3390/md21080425.

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Dinoflagellates are unicellular organisms that are implicated in harmful algal blooms (HABs) caused by potent toxins that are produced through polyketide synthase (PKS) pathways. However, the exact mechanisms of toxin synthesis are unknown due to a lack of genomic segregation of fat, toxins, and other PKS-based pathways. To better understand the underlying mechanisms, the actions and expression of the PKS proteins were investigated using the toxic dinoflagellate Amphidinium carterae as a model. Cerulenin, a known ketosynthase inhibitor, was shown to reduce acetate incorporation into all fat classes with the toxins amphidinol and sulpho-amphidinol. The mass spectrometry analysis of cerulenin-reacted synthetic peptides derived from ketosynthase domains of A. carterae multimodular PKS transcripts demonstrated a strong covalent bond that could be localized using collision-induced dissociation. One multi-modular PKS sequence present in all dinoflagellates surveyed to date was found to lack an AT domain in toxin-producing species, indicating trans-acting domains, and was shown by Western blotting to be post-transcriptionally processed. These results demonstrate how toxin synthesis in dinoflagellates can be differentiated from fat synthesis despite common underlying pathway.

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21

Chen, Kai, Zhengshuang Xu, and Tao Ye. "Total synthesis of amphidinins E, F and epi-amphidinin F." Organic Chemistry Frontiers 5, no. 4 (2018): 629–32. http://dx.doi.org/10.1039/c7qo00820a.

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22

Fürstner, Alois, Christophe Aïssa, Ricardo Riveiros, and Jacques Ragot. "Totalsynthese von Amphidinolid T4." Angewandte Chemie 114, no. 24 (December 16, 2002): 4958–60. http://dx.doi.org/10.1002/ange.200290041.

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23

Wakamiya, Yuma, Makoto Ebine, Nobuaki Matsumori, and Tohru Oishi. "Total Synthesis of Amphidinol 3: A General Strategy for Synthesizing Amphidinol Analogues and Structure–Activity Relationship Study." Journal of the American Chemical Society 142, no. 7 (January 27, 2020): 3472–78. http://dx.doi.org/10.1021/jacs.9b11789.

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24

Crimmins, Michael T., Timothy J. Martin, and Theodore A. Martinot. "Synthesis of the Bis-tetrahydropyran Core of Amphidinol 3." Organic Letters 12, no. 17 (September 3, 2010): 3890–93. http://dx.doi.org/10.1021/ol1015898.

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25

Bensoussan, Charlélie, Nicolas Rival, Gilles Hanquet, Françoise Colobert, Sébastien Reymond, and Janine Cossy. "Isolation, structural determination and synthetic approaches toward amphidinol 3." Natural Product Reports 31, no. 4 (2014): 468. http://dx.doi.org/10.1039/c3np70062c.

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26

de Vicente, Javier, John R. Huckins, and Scott D. Rychnovsky. "Synthesis of the C31–C67 Fragment of Amphidinol 3." Angewandte Chemie 118, no. 43 (November 6, 2006): 7416–20. http://dx.doi.org/10.1002/ange.200602742.

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27

de Vicente, Javier, John R. Huckins, and Scott D. Rychnovsky. "Synthesis of the C31–C67 Fragment of Amphidinol 3." Angewandte Chemie International Edition 45, no. 43 (November 6, 2006): 7258–62. http://dx.doi.org/10.1002/anie.200602742.

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28

Cossy, Janine, Tomoki Tsuchiya, Sébastien Reymond, Thomas Kreuzer, Françoise Colobert, and István Markó. "Convergent Synthesis of the C18-C30 Fragment of Amphidinol 3." Synlett 2009, no. 16 (September 3, 2009): 2706–10. http://dx.doi.org/10.1055/s-0029-1217754.

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29

Tsuruda, Takeshi, Makoto Ebine, Aya Umeda, and Tohru Oishi. "Stereoselective Synthesis of the C1–C29 Part of Amphidinol 3." Journal of Organic Chemistry 80, no. 2 (January 7, 2015): 859–71. http://dx.doi.org/10.1021/jo502322m.

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30

Manabe, Yoshiyuki, Makoto Ebine, Nobuaki Matsumori, Michio Murata, and Tohru Oishi. "Confirmation of the Absolute Configuration at C45 of Amphidinol 3." Journal of Natural Products 75, no. 11 (November 6, 2012): 2003–6. http://dx.doi.org/10.1021/np300604w.

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31

Houdai, Toshihiro, Nobuaki Matsumori, and Michio Murata. "Structure of Membrane-Bound Amphidinol 3 in Isotropic Small Bicelles." Organic Letters 10, no. 19 (October 2, 2008): 4191–94. http://dx.doi.org/10.1021/ol8016337.

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32

Rival, Nicolas, Damien Hazelard, Gilles Hanquet, Thomas Kreuzer, Charlelie Bensoussan, Sébastien Reymond, Janine Cossy, and Françoise Colobert. "Diastereoselective synthesis of the C17–C30 fragment of amphidinol 3." Organic & Biomolecular Chemistry 10, no. 47 (2012): 9418. http://dx.doi.org/10.1039/c2ob26641e.

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33

Rival, Nicolas, Gilles Hanquet, Charlelie Bensoussan, Sébastien Reymond, Janine Cossy, and Françoise Colobert. "Diastereoselective synthesis of the C14–C29 fragment of amphidinol 3." Organic & Biomolecular Chemistry 11, no. 39 (2013): 6829. http://dx.doi.org/10.1039/c3ob41569d.

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34

Murata, Michio, Respati T. Swasono, Mitsunori Kanemoto, and Tohru Oishi. "Structural Reevaluations of Amphidinol 3, a Potent Antifungal Compound from Dinoflagellate." HETEROCYCLES 82, no. 2 (2010): 1359. http://dx.doi.org/10.3987/com-10-s(e)86.

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35

Meng, Yanhui, Ryan M. Van Wagoner, Ian Misner, Carmelo Tomas, and Jeffrey L. C. Wright. "Structure and Biosynthesis of Amphidinol 17, a Hemolytic Compound fromAmphidinium carterae⊥." Journal of Natural Products 73, no. 3 (March 26, 2010): 409–15. http://dx.doi.org/10.1021/np900616q.

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36

Hicks, Jacqueline D., Eric M. Flamme, and William R. Roush. "Synthesis of the C(43)−C(67) Fragment of Amphidinol 3." Organic Letters 7, no. 24 (November 2005): 5509–12. http://dx.doi.org/10.1021/ol052322j.

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37

Bensoussan, Charlelie, Nicolas Rival, Gilles Hanquet, Francoise Colobert, Sebastien Reymond, and Janine Cossy. "ChemInform Abstract: Isolation, Structural Determination, and Synthetic Approaches Toward Amphidinol 3." ChemInform 45, no. 30 (July 10, 2014): no. http://dx.doi.org/10.1002/chin.201430244.

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38

Murata, Michio, Shigeru Matsuoka, Nobuaki Matsumori, Gopal K. Paul, and Kazuo Tachibana. "Absolute Configuration of Amphidinol 3, the First Complete Structure Determination from Amphidinol Homologues: Application of a New Configuration Analysis Based on Carbon−Hydrogen Spin-Coupling Constants." Journal of the American Chemical Society 121, no. 4 (February 1999): 870–71. http://dx.doi.org/10.1021/ja983655x.

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39

Espiritu, Rafael A. "Membrane permeabilizing action of amphidinol 3 and theonellamide A in raft-forming lipid mixtures." Zeitschrift für Naturforschung C 72, no. 1-2 (January 26, 2017): 43–48. http://dx.doi.org/10.1515/znc-2016-0043.

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Abstract 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. In this report, the activity of AM3 and TNM-A in ternary lipid mixtures composed of 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (POPC):brain sphingomyelin:cholesterol at a mole ratio of 1:1:1 or 3:1:1 exhibiting lipid rafts coexistence is presented. It was found that AM3 has a more extensive membrane permeabilizing activity compared with TNM-A in these membrane mimics, which was almost complete at 15 μM. The extent of their activity nevertheless is similar to the previously reported binary system of POPC and cholesterol, suggesting that phase separation has neither beneficial nor detrimental effects in their ability to disrupt the lipid bilayer.

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40

Espiritu, Rafael Atillo, Nobuaki Matsumori, Masashi Tsuda, and Michio Murata. "Direct and Stereospecific Interaction of Amphidinol 3 with Sterol in Lipid Bilayers." Biochemistry 53, no. 20 (May 12, 2014): 3287–93. http://dx.doi.org/10.1021/bi5002932.

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41

Kanemoto, Mitsunori, Michio Murata, and Tohru Oishi. "Stereoselective Synthesis of the C31−C40/C43−C52 Unit of Amphidinol 3." Journal of Organic Chemistry 74, no. 22 (November 20, 2009): 8810–13. http://dx.doi.org/10.1021/jo901793f.

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42

Ebine, Makoto, Mitsunori Kanemoto, Yoshiyuki Manabe, Yosuke Konno, Ken Sakai, Nobuaki Matsumori, Michio Murata, and Tohru Oishi. "Synthesis and Structure Revision of the C43–C67 Part of Amphidinol 3." Organic Letters 15, no. 11 (May 21, 2013): 2846–49. http://dx.doi.org/10.1021/ol401176a.

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43

Wakamiya, Yuma, Makoto Ebine, Mariko Murayama, Hiroyuki Omizu, Nobuaki Matsumori, Michio Murata, and Tohru Oishi. "Synthesis and Stereochemical Revision of the C31-C67 Fragment of Amphidinol 3." Angewandte Chemie 130, no. 21 (April 27, 2018): 6168–72. http://dx.doi.org/10.1002/ange.201712167.

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44

Yadav, Jhillu S., Yerragorla Gopalarao, Dandekar Chandrakanth, and Basi V. Subba Reddy. "Stereoselective Synthesis of the C(1) - C(28) Fragment of Amphidinol 3." Helvetica Chimica Acta 99, no. 6 (June 2016): 436–46. http://dx.doi.org/10.1002/hlca.201500281.

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Wakamiya, Yuma, Makoto Ebine, Mariko Murayama, Hiroyuki Omizu, Nobuaki Matsumori, Michio Murata, and Tohru Oishi. "Synthesis and Stereochemical Revision of the C31-C67 Fragment of Amphidinol 3." Angewandte Chemie International Edition 57, no. 21 (April 27, 2018): 6060–64. http://dx.doi.org/10.1002/anie.201712167.

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46

Murata, Michio, Shigeru Matsuoka, Nobuaki Matsumori, Gopal K. Paul, and Kazuo Tachibana. "ChemInform Abstract: Absolute Configuration of Amphidinol 3 (I), the First Complete Structure Determination from Amphidinol Homologues: Application of a New Configuration Analysis Based on Carbon-Hydrogen Spin-Coupling Constants." ChemInform 30, no. 25 (June 15, 2010): no. http://dx.doi.org/10.1002/chin.199925207.

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47

Barone, Maria Elena, Elliot Murphy, Rachel Parkes, Gerard T. A. Fleming, Floriana Campanile, Olivier P. Thomas, and Nicolas Touzet. "Antibacterial Activity and Amphidinol Profiling of the Marine Dinoflagellate Amphidinium carterae (Subclade III)." International Journal of Molecular Sciences 22, no. 22 (November 11, 2021): 12196. http://dx.doi.org/10.3390/ijms222212196.

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Abstract:

Microalgae have received growing interest for their capacity to produce bioactive metabolites. This study aimed at characterising the antimicrobial potential of the marine dinoflagellate Amphidinium carterae strain LACW11, isolated from the west of Ireland. Amphidinolides have been identified as cytotoxic polyoxygenated polyketides produced by several Amphidinium species. Phylogenetic inference assigned our strain to Amphidinium carterae subclade III, along with isolates interspersed in different geographic regions. A two-stage extraction and fractionation process of the biomass was carried out. Extracts obtained after stage-1 were tested for bioactivity against bacterial ATCC strains of Staphylococcus aureus, Enterococcus faecalis, Escherichia coli and Pseudomonas aeruginosa. The stage-2 solid phase extraction provided 16 fractions, which were tested against S. aureus and E. faecalis. Fractions I, J and K yielded minimum inhibitory concentrations between 16 μg/mL and 256 μg/mL for both Gram-positive. A targeted metabolomic approach using UHPLC-HRMS/MS analysis applied on fractions G to J evidenced the presence of amphidinol type compounds AM-A, AM-B, AM-22 and a new derivative dehydroAM-A, with characteristic masses of m/z 1361, 1463, 1667 and 1343, respectively. Combining the results of the biological assays with the targeted metabolomic approach, we could conclude that AM-A and the new derivative dehydroAM-A are responsible for the detected antimicrobial bioactivity.

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Oishi, Tohru, Tomoyuki Koge, and Makoto Ebine. "Synthesis of an Analog of Amphidinol 3 Corresponding to the C31–C67 Section." HETEROCYCLES 96, no. 7 (2018): 1197. http://dx.doi.org/10.3987/com-18-13927.

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Houdai, Toshihiro, Shigeru Matsuoka, Nobuaki Matsumori, and Michio Murata. "Membrane-permeabilizing activities of amphidinol 3, polyene-polyhydroxy antifungal from a marine dinoflagellate." Biochimica et Biophysica Acta (BBA) - Biomembranes 1667, no. 1 (November 2004): 91–100. http://dx.doi.org/10.1016/j.bbamem.2004.09.002.

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Colobert, Françoise, Thomas Kreuzer, Janine Cossy, Sébastien Reymond, Tomoki Tsuchiya, Laurent Ferrié, Istvan Marko, and Pierre Jourdain. "Stereoselective Synthesis of the C(53)-C(67) Polyene Fragment of Amphidinol 3." Synlett 2007, no. 15 (September 2007): 2351–54. http://dx.doi.org/10.1055/s-2007-985601.

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