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Peyssonnosides A–B, unusual diterpene glycosides with a sterically encumbered cyclopropane motif : structure elucidation using an integrated spectroscopic and computational workflow

Khatri Chhetri Bhuwan, Lavoie Serge, Sweeney-Jones Anne Marie, Mojib Nazia, Raghavan Vijay, Gagaring Kerstin, Dale Brandon, McNamara Case W., Soapi Katy, Quave Cassandra L., Polavarapu Prasad L. et Kubanek Julia. (2019). Peyssonnosides A–B, unusual diterpene glycosides with a sterically encumbered cyclopropane motif : structure elucidation using an integrated spectroscopic and computational workflow. The Journal of Organic Chemistry, 84, (13), p. 8531-8541.

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URL officielle: http://dx.doi.org/doi:10.1021/acs.joc.9b00884

Résumé

Two sulfated diterpene glycosides featuring a highly substituted and sterically encumbered cyclopropane ring have been isolated from the marine red alga Peyssonnelia sp. Combination of a wide array of 2D NMR spectroscopic experiments, in a systematic structure elucidation workflow, revealed that peyssonnosides A–B (1–2) represent a new class of diterpene glycosides with a tetracyclo [7.5.0.01,10.05,9] tetradecane architecture. A salient feature of this workflow is the unique application of quantitative interproton distances obtained from the rotating frame Overhauser effect spectroscopy (ROESY) NMR experiment, wherein the β-d-glucose moiety of 1 was used as an internal probe to unequivocally determine the absolute configuration, which was also supported by optical rotatory dispersion (ORD). Peyssonnoside A (1) exhibited promising activity against liver stage Plasmodium berghei and moderate antimethicillin-resistant Staphylococcus aureus (MRSA) activity, with no cytotoxicity against human keratinocytes. Additionally, 1 showed strong growth inhibition of the marine fungus Dendryphiella salina indicating an antifungal ecological role in its natural environment. The high natural abundance and novel carbon skeleton of 1 suggests a rare terpene cyclase machinery, exemplifying the chemical diversity in this phylogenetically distinct marine red alga.

Type de document:Article publié dans une revue avec comité d'évaluation
ISSN:0022-3263
Volume:84
Numéro:13
Pages:p. 8531-8541
Version évaluée par les pairs:Oui
Date:2019
Identifiant unique:10.1021/acs.joc.9b00884
Sujets:Sciences naturelles et génie > Sciences naturelles > Chimie
Département, module, service et unité de recherche:Départements et modules > Département des sciences fondamentales
Mots-clés:Red alga, diterpene glycoside, antiplasmodial, cyclopropane
Déposé le:01 sept. 2021 18:26
Dernière modification:01 sept. 2021 18:26
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