New Antineoplastic Naphthohydroquinones Attached to Labdane and Rearranged Diterpene Skeletons

New Antineoplastic Naphthohydroquinones Attached to Labdane and Rearranged Diterpene Skeletons

Terpenylquinones are mixed biogenesis primary or secondary metabolites widespread in Nature with many biological activities, including the antineoplastic cytotoxicity, that have inspired this work. Here, we present a cytotoxic structure-activity relationship of several diterpenylhydroquinone (DTHQ)...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Vol. 26; no. 2; p. 474
Main Authors: Hernández, Ángela P, Chamorro, Pablo, Rodríguez, Mª Lucena, Miguel Del Corral, José M, García, Pablo A, Francesch, Andrés, San Feliciano, Arturo, Castro, Mª Ángeles
Format: Journal Article
Language:English
Published: Switzerland MDPI AG 18-01-2021
MDPI
Subjects:
Acids
Bioactive compounds
Biocompatibility
Biomimetics
Cytotoxicity
Decalin
Decarboxylation
Diterpenes
Experiments
halimane
Isomers
labdane
Metabolites
rearranged diterpenes
Secondary metabolites
Stereochemistry
terpenylquinone
rearranged diterpenes
terpenylquinone
labdane
halimane
cytotoxicity
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Summary:Terpenylquinones are mixed biogenesis primary or secondary metabolites widespread in Nature with many biological activities, including the antineoplastic cytotoxicity, that have inspired this work. Here, we present a cytotoxic structure-activity relationship of several diterpenylhydroquinone (DTHQ) derivatives, obtained from the natural labdane diterpenoid myrceocommunic acid used as starting material. Different structural modifications, that changed the functionality and stereochemistry of the decalin, have been implemented on the bicyclic core through epoxidation, ozonolysis or decarboxylation, and through induction of biomimetic breaks and rearrangements of the diterpene skeleton. All the isomers generated were completely characterized by spectroscopic procedures. The resulting compounds have been tested in vitro on cultured cancer cells, showing their relevant antineoplastic cytotoxicity, with GI values in the μM and sub-μM range. The rearranged compound showed the best cytotoxic results, with GI at the submicromolar range, retaining the cytotoxicity level of the parent compounds. In this report, the versatility of the labdane skeleton for chemical transformation and the interest to continue using structural modifications to obtain new bioactive compounds are demonstrated.
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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules26020474