Bio-inspired dimerisation of prenylated quinones directed towards the synthesis of the meroterpenoid natural products, the scabellones

Chan, Sy; Pullar, Michael A.; Khalil, Iman M.; Allouche, Emmanuelle M. D.; Barker, David; Copp, Brent R.

doi:10.1016/j.tetlet.2015.02.024

Cited by 12 publications

(10 citation statements)

References 15 publications

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“…The eighteen new tunicate-derived natural products presented in this review is the second lowest annual count since 2002. The metabolites reported included a meroterpenoid 1317, 934 940 Noteworthy were the isolation, structure elucidation, synthesis and biological evaluation of eudistidines A 1333 and B 1334 (Eudistoma sp., Palau). 940 A fourstep condensation/cyclisation reaction sequence afforded both natural products, allowing conrmation of their structures.…”

Section: Molluscsmentioning

confidence: 99%

Marine natural products

et al. 2017

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Covering: 2015. Previous review: Nat. Prod. Rep., 2016, 33, 382-431This review covers the literature published in 2015 for marine natural products (MNPs), with 1220 citations (792 for the period January to December 2015) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1340 in 429 papers for 2015), together with the relevant biological activities, source organisms and country of origin. Reviews, biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.

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Section: Molluscsmentioning

confidence: 99%

Marine natural products

et al. 2017

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“…The direct conversion of prenylated hydroquinones to naphthoquinones is uncommon and presents a novel approach to the synthesis of this important group of compounds. To the best of our knowledge there is only a single report describing the formation of a naphthoquinone as a side-product in the synthesis of chromenes from prenylated quinones [12]. Naphthoquinones are typically synthesized by Diels-Alder reactions between p -benzoquinones and dienes or by the prenylation of halogenated naphthoquinone moieties [13,14,15].…”

Section: Resultsmentioning

confidence: 99%

Semi-Synthesis and Evaluation of Sargahydroquinoic Acid Derivatives as Potential Antimalarial Agents

et al. 2019

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Background: Malaria continues to present a major health problem, especially in developing countries. The development of new antimalarial drugs to counter drug resistance and ensure a steady supply of new treatment options is therefore an important area of research. Meroditerpenes have previously been shown to exhibit antiplasmodial activity against a chloroquinone sensitive strain of Plasmodium falciparum (D10). In this study we explored the antiplasmodial activity of several semi-synthetic analogs of sargahydroquinoic acid. Methods: Sargahydroquinoic acid was isolated from the marine brown alga, Sargassum incisifolium and converted, semi-synthetically, to several analogs. The natural products, together with their synthetic derivatives were evaluated for their activity against the FCR-3 strain of Plasmodium falciparum as well as MDA-MB-231 breast cancer cells. Results: Sarganaphthoquinoic acid and sargaquinoic acid showed the most promising antiplasmodial activity and low cytotoxicity. Conclusions: Synthetic modification of the natural product, sargahydroquinoic acid, resulted in the discovery of a highly selective antiplasmodial compound, sarganaphthoquinoic acid.

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“…Scabellone A ( 20 ) contained a 5-substituted chromenol fragment, while the others contained a benzo[ c ]chromene-7,10-dione scaffold, which was particularly rare among natural products [ 13 ]. In terms of biogenesis, it seemed reasonably that they proceeded via dimerization of 2-geranyl-6-methoxybenzoquinone and/or 2-geranyl-6-methoxyhydroquinone, and in fact, the same authors performed a biomimetic dimerization synthesis of scabellones A and B starting from 2-geranyl-6-methoxyhydroquinone with oxygen in pyridine [ 14 ].…”

Section: Meroterpenoids With Open-chain and Cyclic Monoterpenoidsmentioning

confidence: 99%

“…Not only BQ meroterpenoids have been identified from marine organisms, but there are also diverse NQ derivatives. One simple example of this kind is scabellone E ( 48 ) ( Figure 6 ), a NQ derivative that was first obtained during the biomimetic cyclization of 2-geranyl-6-methoxyhydroquinone, and which was identified later as a natural compound in the extract of A. scabellum [ 14 ].…”

Section: Meroterpenoids With Open-chain and Cyclic Monoterpenoidsmentioning

confidence: 99%

Bioactive Prenyl- and Terpenyl-Quinones/Hydroquinones of Marine Origin †

et al. 2018

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The sea is a rich source of biological active compounds, among which terpenyl-quinones/hydroquinones constitute a family of secondary metabolites with diverse pharmacological properties. The chemical diversity and bioactivity of those isolated from marine organisms in the last 10 years are summarized in this review. Aspects related to synthetic approaches towards the preparation of improved bioactive analogues from inactive terpenoids are also outlined.

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Bio-inspired dimerisation of prenylated quinones directed towards the synthesis of the meroterpenoid natural products, the scabellones

Cited by 12 publications

References 15 publications

Marine natural products

Marine natural products

Semi-Synthesis and Evaluation of Sargahydroquinoic Acid Derivatives as Potential Antimalarial Agents

Bioactive Prenyl- and Terpenyl-Quinones/Hydroquinones of Marine Origin †

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