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Investigation of the electrophilic reactivity of the biologically active marine sesquiterpenoid onchidal and model compounds.

ABSTRACT: The structure of the sesquiterpene onchidal (6), a component of the defensive secretion of the shell-less mollusc Onchidella binneyi, contains a masked ?,?-unsaturated 1,4-dialdehyde moiety, the presence of which has been proposed to be the cause of the feeding deterrent activity exhibited by the mollusc. We have found onchidal acts as an electrophile, reacting rapidly with the model nucleophile n-pentylamine forming diastereomeric aminated pyrrole adducts. Somewhat surprisingly, no reaction was observed between onchidal and n-pentanethiol. Structurally simplified n-pentyl 11-13 and cyclohexylmethyl 15-17 analogues of onchidal were prepared and demonstrated similar amine-selective reactivity. Onchidal and analogues reacted with the model protein lysozyme, forming covalent adducts and leading to protein cross-linking. These results provide preliminary evidence supporting the molecular mechanism of biological activity exhibited by onchidal.

SUBMITTER: Cadelis MM

PROVIDER: S-EPMC6122400 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

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Investigation of the electrophilic reactivity of the biologically active marine sesquiterpenoid onchidal and model compounds.

Cadelis Melissa M MM Copp Brent R BR

Beilstein journal of organic chemistry 20180824

The structure of the sesquiterpene onchidal (6), a component of the defensive secretion of the shell-less mollusc Onchidella binneyi, contains a masked α,β-unsaturated 1,4-dialdehyde moiety, the presence of which has been proposed to be the cause of the feeding deterrent activity exhibited by the mollusc. We have found onchidal acts as an electrophile, reacting rapidly with the model nucleophile n-pentylamine forming diastereomeric aminated pyrrole adducts. Somewhat surprisi ...[more]

PMID: 30202476

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Project description:Despite the progress made in immunization and drug development, so far there are no prophylactic vaccines and effective therapies for many viral infections, including infections caused by coronaviruses. In this regard, the search for new antiviral substances continues to be relevant, and the enormous potential of marine resources are a stimulus for the study of marine compounds with antiviral activity in experiments and clinical trials. The highly pathogenic human coronaviruses-severe acute respiratory syndrome-related coronavirus (SARS-CoV), Middle East respiratory syndrome coronavirus (MERS-CoV), severe acute respiratory syndrome-related coronavirus 2 (SARS-CoV-2) remain a serious threat to human health. In this review, the authors hope to bring the attention of researchers to the use of biologically active substances of marine origin as potential broad-spectrum antiviral agents targeting common cellular pathways and various stages of the life cycle of different viruses, including coronaviruses. The review has been compiled using references from major databases such as Web of Science, PubMed, Scopus, Elsevier, Springer and Google Scholar (up to June 2020) and keywords such as 'coronaviruses', 'marine organisms', 'biologically active substances', 'antiviral drugs', 'SARS-CoV', 'MERS-CoV', 'SARS-CoV-2', '3CLpro', 'TMPRSS2', 'ACE2'. After obtaining all reports from the databases, the papers were carefully analysed in order to find data related to the topic of this review (98 references). Biologically active substances of marine origin, such as flavonoids, phlorotannins, alkaloids, terpenoids, peptides, lectins, polysaccharides, lipids and others substances, can affect coronaviruses at the stages of penetration and entry of the viral particle into the cell, replication of the viral nucleic acid and release of the virion from the cell; they also can act on the host's cellular targets. These natural compounds could be a vital resource in the fight against coronaviruses.

Dataset Information

Investigation of the electrophilic reactivity of the biologically active marine sesquiterpenoid onchidal and model compounds.

Publications

Investigation of the electrophilic reactivity of the biologically active marine sesquiterpenoid onchidal and model compounds.

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