Structure and Stereochemistry of Amphidinolide N Congeners from Marine Dinoflagellate &lt;i&gt;Amphidinium&lt;/i&gt; Species

Tsuda, Masashi; Akakabe, Mai; Minamida, Mika; Kumagai, Kazuaki; Tsuda, Masayuki; Konishi, Yuko; Tominaga, Akira; Fukushi, Eri; Kawabata, Jun

doi:10.1248/cpb.c20-00745

Cited by 6 publications

(4 citation statements)

References 26 publications

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“…disclosed their synthesis of 232 , Tsuda and coworkers published a new proposed structure for amphidinolide N on the basis of extensive NMR studies on both amphidinolide N itself and two closely related analogs (Scheme 39). [168] Interestingly, this new structure ( 233 ) is the C2,C10,C14,C15‐tetraepimer of the revised structure that Kobayashi disclosed in 2013 ( 208 ), [153] and exhibits the same configuration at C15 as des ‐epoxyamphidinolide N ( 232 ). Assuming that the overall conformation of these molecules is indeed critical for epoxidation as Trost proposed, the stereochemical differences between 208 , 232 , and 233 are notable, and may help explain why 232 was difficult to epoxidize.…”

Section: (−)‐Des‐epoxyamphidinolide Nmentioning

confidence: 91%

Total Synthesis in the Trost Laboratories: Selected Milestones From the Past Twenty Years

Mata¹,

Kalnmals

2021

Israel Journal of Chemistry

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Since the early days of his independent career, Prof. Barry M. Trost has maintained a keen interest in complex molecule synthesis. Over the past 55 years, Trost and coworkers have reported syntheses of more than 260 natural products, pharmaceuticals, and other complex biomolecules – a truly extraordinary feat and an incredible testament to Prof. Trost's inventiveness and ingenuity. Even more remarkably, Trost generated more than half of this output – as well as some of his most daring and ambitious syntheses – in just the past twenty years. This review provides a brief summary of all total syntheses from the Trost laboratories since 2000, as well as more detailed vignettes of sixteen particularly notable campaigns, including conquests of callipeltoside A, galanthamine and three related alkaloids, agelastatin A, terpestacin, pseudolaric acid B, ushikolide A, bryostatin 16, laulimalide, aeruginosin 98B, lasonolide A, perophoramidine, leustroducsin B, des‐epoxy‐amphidinolide N, bulleyanaline and three related alkaloids, and bryostatin 3.

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Section: (−)‐Des‐epoxyamphidinolide Nmentioning

confidence: 91%

Total Synthesis in the Trost Laboratories: Selected Milestones From the Past Twenty Years

Mata¹,

Kalnmals

2021

Israel Journal of Chemistry

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“…335 Two new amphidinolide N congeners 874 and 875 are potent cytotoxins isolated from Amphidinium sp. 336 A report of three new amphidiniols 876–878 has suggested that centrifugation to clarify the culture media is a stressor that prompts release of the compounds from the dinoflagellate into the surrounding liquid. 337 Karenia brevisulcata is a well-documented producer of potently toxic metabolites, with two new brevisulcenal-type sulfated esters 879 and 880 being sourced from a New Zealand isolate of the dinoflagellate.…”

Section: Marine Microorganisms and Phytoplanktonmentioning

confidence: 99%

Marine natural products

et al. 2023

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“…The most potent anticancer compounds identified to date are two macrolides (isocaribenolide-I and chlorohydrin-2) recently isolated from a free-living Amphidinium sp. (strain KCA09053) and found to possess high cytotoxic activity against human cervix adenocarcinoma cells [68]. Caribenolide I, isolated from a free-living Amphidinium sp., was found to possess cytotoxic activities towards human colon tumour cells [69].…”

Section: Anticancer Activitymentioning

confidence: 99%

Amphidinium spp. as a Source of Antimicrobial, Antifungal, and Anticancer Compounds

Orefice,

Balzano,

Romano

et al. 2023

Life

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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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Structure and Stereochemistry of Amphidinolide N Congeners from Marine Dinoflagellate <i>Amphidinium</i> Species

Cited by 6 publications

References 26 publications

Total Synthesis in the Trost Laboratories: Selected Milestones From the Past Twenty Years

Total Synthesis in the Trost Laboratories: Selected Milestones From the Past Twenty Years

Marine natural products

Amphidinium spp. as a Source of Antimicrobial, Antifungal, and Anticancer Compounds

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