Total synthesis of janadolide

Ojima, Daisuke; Mine, Hitomi; Iwasaki, Arihiro; Suenaga, Kiyotake

doi:10.1016/j.tetlet.2018.02.034

Cited by 9 publications

(5 citation statements)

References 28 publications

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“…Intriguingly, janadolide is another reported cyclic polyketide−peptide with potent antitrypanosomal activity and no cytotoxicity against human cells [ 38 ]. The compound has been totally synthesized through lithiation of vinyl iodide, its addition to a Weinreb amide with a tert -butyl group and stereoselective 1,2-reduction, and finally macrolactamization [ 53 ]. Recently, other researchers synthesized the same compound and small library (18a–h) of its simplified analogues via an enantioselective (−)-B-chlorodiisopinocampheylborane-mediated reduction and a B-alkyl Suzuki reaction.…”

Section: Discussionmentioning

confidence: 99%

Potentials of marine natural products against malaria, leishmaniasis, and trypanosomiasis parasites: a review of recent articles

et al. 2021

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Background Malaria and neglected communicable protozoa parasitic diseases, such as leishmaniasis, and trypanosomiasis, are among the otherwise called diseases for neglected communities, which are habitual in underprivileged populations in developing tropical and subtropical regions of Africa, Asia, and the Americas. Some of the currently available therapeutic drugs have some limitations such as toxicity and questionable efficacy and long treatment period, which have encouraged resistance. These have prompted many researchers to focus on finding new drugs that are safe, effective, and affordable from marine environments. The aim of this review was to show the diversity, structural scaffolds, in-vitro or in-vivo efficacy, and recent progress made in the discovery/isolation of marine natural products (MNPs) with potent bioactivity against malaria, leishmaniasis, and trypanosomiasis. Main text We searched PubMed and Google scholar using Boolean Operators (AND, OR, and NOT) and the combination of related terms for articles on marine natural products (MNPs) discovery published only in English language from January 2016 to June 2020. Twenty nine articles reported the isolation, identification and antiparasitic activity of the isolated compounds from marine environment. A total of 125 compounds were reported to have been isolated, out of which 45 were newly isolated compounds. These compounds were all isolated from bacteria, a fungus, sponges, algae, a bryozoan, cnidarians and soft corals. In recent years, great progress is being made on anti-malarial drug discovery from marine organisms with the isolation of these potent compounds. Comparably, some of these promising antikinetoplastid MNPs have potency better or similar to conventional drugs and could be developed as both antileishmanial and antitrypanosomal drugs. However, very few of these MNPs have a pharmaceutical destiny due to lack of the following: sustainable production of the bioactive compounds, standard efficient screening methods, knowledge of the mechanism of action, partnerships between researchers and pharmaceutical industries. Conclusions It is crystal clear that marine organisms are a rich source of antiparasitic compounds, such as alkaloids, terpenoids, peptides, polyketides, terpene, coumarins, steroids, fatty acid derivatives, and lactones. The current and future technological innovation in natural products drug discovery will bolster the drug armamentarium for malaria and neglected tropical diseases.

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Section: Discussionmentioning

confidence: 99%

Potentials of marine natural products against malaria, leishmaniasis, and trypanosomiasis parasites: a review of recent articles

et al. 2021

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“…Remarkably, it was found that 24 was more effective than suramin (IC 50 value of 1.2 µM), a commonly used therapeutic drug [150]. Two years after its discovery, janadolide (24) was synthetized by Ojima et al [230]. Moreover, a des-tert-butyl analogue of 24 was also reported but with reduced activity against T. b. brucei [231].…”

Section: Trypanosomiasismentioning

confidence: 99%

Therapeutic Potential of Marine-Derived Cyclic Peptides as Antiparasitic Agents

Ribeiro,

Costa,

Pinto

et al. 2023

Marine Drugs

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Parasitic diseases still compromise human health. Some of the currently available therapeutic drugs have limitations considering their adverse effects, questionable efficacy, and long treatment, which have encouraged drug resistance. There is an urgent need to find new, safe, effective, and affordable antiparasitic drugs. Marine-derived cyclic peptides have been increasingly screened as candidates for developing new drugs. Therefore, in this review, a systematic analysis of the scientific literature was performed and 25 marine-derived cyclic peptides with antiparasitic activity (1–25) were found. Antimalarial activity is the most reported (51%), followed by antileishmanial (27%) and antitrypanosomal (20%) activities. Some compounds showed promising antiparasitic activity at the nM scale, being active against various parasites. The mechanisms of action and targets for some of the compounds have been investigated, revealing different strategies against parasites.

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“…Compound 72 showed potent antitrypanosomal activity with an IC 50 value of 47 nM, without cytotoxicity against human cells [ 210 ]. The steps of the total synthesis of 72 were due to the macrolactamization of the proline moiety and fatty acid moiety manifested by the amide bond, as seen in Scheme 2 [ 227 ]. Kurahyne B ( 74 ), a new kurahyne analog, has been separated from the marine cyanobacterium Okeania sp.…”

Section: Total Synthesis and Stereochemical Determination Of Marine Cyanobacteria Bioactive Compoundsmentioning

confidence: 99%

Cyanobacteria—From the Oceans to the Potential Biotechnological and Biomedical Applications

et al. 2021

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Cyanobacteria are photosynthetic prokaryotic organisms which represent a significant source of novel, bioactive, secondary metabolites, and they are also considered an abundant source of bioactive compounds/drugs, such as dolastatin, cryptophycin 1, curacin toyocamycin, phytoalexin, cyanovirin-N and phycocyanin. Some of these compounds have displayed promising results in successful Phase I, II, III and IV clinical trials. Additionally, the cyanobacterial compounds applied to medical research have demonstrated an exciting future with great potential to be developed into new medicines. Most of these compounds have exhibited strong pharmacological activities, including neurotoxicity, cytotoxicity and antiviral activity against HCMV, HSV-1, HHV-6 and HIV-1, so these metabolites could be promising candidates for COVID-19 treatment. Therefore, the effective large-scale production of natural marine products through synthesis is important for resolving the existing issues associated with chemical isolation, including small yields, and may be necessary to better investigate their biological activities. Herein, we highlight the total synthesized and stereochemical determinations of the cyanobacterial bioactive compounds. Furthermore, this review primarily focuses on the biotechnological applications of cyanobacteria, including applications as cosmetics, food supplements, and the nanobiotechnological applications of cyanobacterial bioactive compounds in potential medicinal applications for various human diseases are discussed.

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Total synthesis of janadolide

Cited by 9 publications

References 28 publications

Potentials of marine natural products against malaria, leishmaniasis, and trypanosomiasis parasites: a review of recent articles

Potentials of marine natural products against malaria, leishmaniasis, and trypanosomiasis parasites: a review of recent articles

Therapeutic Potential of Marine-Derived Cyclic Peptides as Antiparasitic Agents

Cyanobacteria—From the Oceans to the Potential Biotechnological and Biomedical Applications

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