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Keywords = terpenylquinones

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16 pages, 3086 KiB  
Article
New Antineoplastic Naphthohydroquinones Attached to Labdane and Rearranged Diterpene Skeletons
by Ángela P. Hernández, Pablo Chamorro, Mª Lucena Rodríguez, José M. Miguel del Corral, Pablo A. García, Andrés Francesch, Arturo San Feliciano and Mª Ángeles Castro
Molecules 2021, 26(2), 474; https://doi.org/10.3390/molecules26020474 - 18 Jan 2021
Cited by 4 | Viewed by 2327
Abstract
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 [...] Read more.
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 GI50 values in the μM and sub-μM range. The rearranged compound 8 showed the best cytotoxic results, with GI50 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. Full article
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17 pages, 2282 KiB  
Article
Anti-Herpetic, Anti-Dengue and Antineoplastic Activities of Simple and Heterocycle-Fused Derivatives of Terpenyl-1,4-Naphthoquinone and 1,4-Anthraquinone
by Vicky C. Roa-Linares, Yaneth Miranda-Brand, Verónica Tangarife-Castaño, Rodrigo Ochoa, Pablo A. García, Mª Ángeles Castro, Liliana Betancur-Galvis and Arturo San Feliciano
Molecules 2019, 24(7), 1279; https://doi.org/10.3390/molecules24071279 - 2 Apr 2019
Cited by 34 | Viewed by 4353
Abstract
Quinones are secondary metabolites of higher plants associated with many biological activities, including antiviral effects and cytotoxicity. In this study, the anti-herpetic and anti-dengue evaluation of 27 terpenyl-1,4-naphthoquinone (NQ), 1,4-anthraquinone (AQ) and heterocycle-fused quinone (HetQ) derivatives was done in vitro against Human Herpesvirus [...] Read more.
Quinones are secondary metabolites of higher plants associated with many biological activities, including antiviral effects and cytotoxicity. In this study, the anti-herpetic and anti-dengue evaluation of 27 terpenyl-1,4-naphthoquinone (NQ), 1,4-anthraquinone (AQ) and heterocycle-fused quinone (HetQ) derivatives was done in vitro against Human Herpesvirus (HHV) type 1 and 2, and Dengue virus serotype 2 (DENV-2). The cytotoxicity on HeLa and Jurkat tumor cell lines was also tested. Using plaque forming unit assays, cell viability assays and molecular docking, we found that NQ 4 was the best antiviral compound, while AQ 11 was the most active and selective molecule on the tested tumor cells. NQ 4 showed a fair antiviral activity against Herpesviruses (EC50: <0.4 µg/mL, <1.28 µM) and DENV-2 (1.6 µg/mL, 5.1 µM) on pre-infective stages. Additionally, NQ 4 disrupted the viral attachment of HHV-1 to Vero cells (EC50: 0.12 µg/mL, 0.38 µM) with a very high selectivity index (SI = 1728). The in silico analysis predicted that this quinone could bind to the prefusion form of the E glycoprotein of DENV-2. These findings demonstrate that NQ 4 is a potent and highly selective antiviral compound, while suggesting its ability to prevent Herpes and Dengue infections. Additionally, AQ 11 can be considered of interest as a leader for the design of new anticancer agents. Full article
(This article belongs to the Special Issue Application of Organic Synthesis to Bioactive Compounds)
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52 pages, 15525 KiB  
Review
Bioactive Prenyl- and Terpenyl-Quinones/Hydroquinones of Marine Origin
by Pablo A. García, Ángela P. Hernández, Arturo San Feliciano and Mª Ángeles Castro
Mar. Drugs 2018, 16(9), 292; https://doi.org/10.3390/md16090292 - 21 Aug 2018
Cited by 38 | Viewed by 7872
Abstract
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 [...] Read more.
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. Full article
(This article belongs to the Special Issue Progress on Marine Natural Products as Lead Compounds)
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16 pages, 149 KiB  
Article
Oxidative Degradations of the Side Chain of Unsaturated Ent-labdanes. Part II
by Luis Espinoza Catalán, Karen Catalán Marín, Héctor Carrasco Altamirano, Mauricio Cuellar Fritis and María Cristina Chamy
Molecules 2007, 12(12), 2605-2620; https://doi.org/10.3390/12122605 - 21 Dec 2007
Cited by 1 | Viewed by 9325
Abstract
A route for the degradation of the side chain of ent-labdane derivatives has beendevised, giving the useful synthon 2β,12-dihydroxy-13,14,15,16,17-pentanor-ent-labdane-8-one (8). The use of this compound in the preparation of terpenylquinone derivatives shallbe reported elsewhere. In addition we have synthesized the compound 2β,12-diacetoxy-8β,17-epoxy-13,14,15,16-tetranor-ent-labdane (10), [...] Read more.
A route for the degradation of the side chain of ent-labdane derivatives has beendevised, giving the useful synthon 2β,12-dihydroxy-13,14,15,16,17-pentanor-ent-labdane-8-one (8). The use of this compound in the preparation of terpenylquinone derivatives shallbe reported elsewhere. In addition we have synthesized the compound 2β,12-diacetoxy-8β,17-epoxy-13,14,15,16-tetranor-ent-labdane (10), which upon catalytic epoxide ringopening in alkaline or acid media gave rise in all cases to the formation of tricycliccompounds. Full article
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10 pages, 183 KiB  
Article
Oxidative Degradations of the Side Chain of Unsaturated Ent-labdanes. Part I.
by Luis Espinoza Catalán, Héctor Carrasco Altamirano, Mauricio Cuellar Fritis, Claudio Gallardo Araya and Karen Catalán Marín
Molecules 2007, 12(3), 318-327; https://doi.org/10.3390/12030318 - 6 Mar 2007
Cited by 4 | Viewed by 9484
Abstract
A selective route for the degradation of the unsaturated side chain of ent-labdanes has been devised, giving two useful synthons: 2β-acetoxy-14,15,17-trinor-ent-labdane-8,13- dione (5) and 2β-acetoxy-14,15-dinor-ent-labd-8(17)-en-13-one (7), the use of which for the preparation of terpenylquinone derivatives shall be reported elsewhere. Full article
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