New cytotoxic furoquinones obtained from terpenyl-1,4-naphthoquinones and 1,4-anthracenediones

Corral, José M. Miguel del; Castro, M. Angeles; Oliveira, Alaı́de Braga de; Gualberto, Simone Andrade; Cuevas, Carmen; Feliciano, Arturo San

doi:10.1016/j.bmc.2006.06.053

Cited by 35 publications

(18 citation statements)

References 31 publications

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“…Plant-originated naphthoquinones have been widely used against various human tumours and parasitic diseases in some parts of Asia and South America (Etkin, 2008; Babula et al , 2009). Although the curing mechanism of naphthoquinones is not clear, their accompanying cytotoxic effect has been attributed to the 1,4-naphthoquinone nucleus (Miguel del Corral et al , 2006). Additional observed effects of naphthoquinones include antiviral (Perez-Sacau et al , 2003; Tandon et al , 2004), molluscicidal (Silva et al , 2005), anti-inflammatory, antiplatelet, antiallergic (Lien et al , 1996), antimalarial (Likhitwitayawuid et al , 1998; Biot et al , 2004), antileishmanial (Mantyla et al , 2004), antibacterial, antifungal (Tandon et al , 2004, 2005, 2008), and antiproliferative (Shchekotikhin et al , 2004; Tandon et al , 2004) activities.…”

Section: Discussionmentioning

confidence: 99%

“…Plumbagin was also reported to be a potent inhibitor of the NF-kappaB activation pathway, enhancing apoptosis and suppression of cellular proliferation in human cancer cell lines treated with inflammatory agents (Sandur et al , 2006). Furthermore, many DNA modifications can be attributed to quinonoid compounds, including intercalation, alkylation, induction of strand breaks (nicking), and inhibition of DNA-related enzymes such as topoisomerases (Miguel del Corral et al , 2006). …”

Section: Introductionmentioning

confidence: 99%

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Induced production of antifungal naphthoquinones in the pitchers of the carnivorous plant Nepenthes khasiana

Eilenberg

Pnini-Cohen

Rahamim

et al. 2009

Journal of Experimental Botany

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Nepenthes spp. are carnivorous plants that have developed insect capturing traps, evolved by specific modification of the leaf tips, and are able to utilize insect degradation products as nutritional precursors. A chitin-induced antifungal ability, based on the production and secretion to the trap liquid of droserone and 5-O-methyldroserone, is described here. Such specific secretion uniquely occurred when chitin injection was used as the eliciting agent and probably reflects a certain kind of defence mechanism that has been evolved for protecting the carnivory-based provision of nutritional precursors. The pitcher liquid containing droserone and 5-O-methyldroserone at 3:1 or 4:1 molar ratio, as well as the purified naphthoquinones, exerted an antifungal effect on a wide range of plant and human fungal pathogens. When tested against Candida and Aspergillus spp., the concentrations required for achieving inhibitory and fungicidal effects were significantly lower than those causing cytotoxicity in cells of the human embryonic kidney cell line, 293T. These naturally secreted 1,4-naphthoquinone derivatives, that are assumed to act via semiquinone enhancement of free radical production, may offer a new lead to develop alternative antifungal drugs with reduced selectable pressure for potentially evolved resistance.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Induced production of antifungal naphthoquinones in the pitchers of the carnivorous plant Nepenthes khasiana

Eilenberg

Pnini-Cohen

Rahamim

et al. 2009

Journal of Experimental Botany

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“…[211] Analogous derivatives may be obtained with 1,4-naphthoquinones. Fieser and Wieghard condensed myrcene with 1,4-naphthoquinone in order to get compounds related to Vitamin K. [221] Nevertheless none of the proposed substances show passable activity in comparison to natural compounds.…”

Section: Quinones As Dienophilesmentioning

confidence: 99%

“…Several families of myrcenyl quinones/hydroquinones have been synthesized by Castro, Gordaliza, and Molinari with interesting antitumoral properties against a wide variety of cell culture lines. [211][212][213][214][215][216][217][218][219][220] The usual procedure to obtain terpenylhydroquinones is based on the Diels-Alder reaction between myrcene and p-benzoquinone in the presence of BF 3 ·OEt 2 (Scheme 20). Higher amounts of Lewis acids cause a cyclization of the myrcenyl side chain, or an oxidation of the cycloadduct occurs in the presence of MnO 2 .…”

Section: Quinones As Dienophilesmentioning

confidence: 99%

Myrcene as a Natural Base Chemical in Sustainable Chemistry: A Critical Review

2009

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Currently, a shift towards chemical products derived from renewable, biological feedstocks is observed more and more. However, substantial differences with traditional feedstocks, such as their "hyperfunctionalization," ethical problems caused by competition with foods, and problems with a constant qualitative/quantitative availability of the natural products, occasionally complicate the large-scale market entry of renewable resources. In this context the vast family of terpenes is often not taken into consideration, although the terpenes have been known for hundreds of years as components of essential oils obtained from leaves, flowers, and fruits of many plants. The simple acyclic monoterpenes, particularly the industrially available myrcene, provide a classical chemistry similar to unsaturated hydrocarbons already known from oil and gas. Hence, this Review is aimed at reviving myrcene as a renewable compound suitable for sustainable chemistry in the area of fine chemicals. The versatility of the unsaturated C(10)-hydrocarbon myrcene, leading to products with several different areas of application, is pointed out.

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“…Terpenylquinones have been described from some marine organisms and display several biological activities, including cytotoxicity and anti-inflammatory effect [8]. New hybrid compounds containing terpene and quinone moieties have been prepared and some of them present relevant biological effects including cytotoxicity [9,10] and antifungal effect [11].…”

Section: Introductionmentioning

confidence: 99%

Diterpenylquinone Hybrids: Synthesis and Assessment of Gastroprotective Mechanisms of Action in Human Cells

et al. 2013

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A modern approach in the search for new bioactive molecules is the synthesis of novel chemical entities combining molecules of different biosynthetic origin presenting biological effects as single compounds. Gastroprotective compounds from South American medicinal plants, namely quinones and diterpenes, were used as building blocks to obtain hybrid diterpenylquinones. Starting from the labdane diterpene junicedric acid and two isomers, as well as from three quinones, including lapachol, 18 hybrid molecules were synthesized. Six of them are described for the first time. The potential gastroprotective mechanisms of action of the compounds were assessed in dose-response experiments using human gastric epithelial cells (AGS) and human lung fibroblasts (MRC-5). The following studies were carried out: stimulation of cell proliferation, cytoprotection against sodium taurocholate (NaT)-induced damage, synthesis of PGE 2 and total reduced sulfhydryl (GSH) content. The antioxidant capacity of the compounds was determined on the inhibition of the lipoperoxidation in human erythrocyte membranes. Hybrid compounds presented activities different from those shown by the starting compounds, supporting the potential of this approach in the search for new bioactive molecules. The effects might be modulated by selective modification in the terpene or quinone moieties of the new molecules. Structure-activity relationships are discussed.

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New cytotoxic furoquinones obtained from terpenyl-1,4-naphthoquinones and 1,4-anthracenediones

Cited by 35 publications

References 31 publications

Induced production of antifungal naphthoquinones in the pitchers of the carnivorous plant Nepenthes khasiana

Induced production of antifungal naphthoquinones in the pitchers of the carnivorous plant Nepenthes khasiana

Myrcene as a Natural Base Chemical in Sustainable Chemistry: A Critical Review

Diterpenylquinone Hybrids: Synthesis and Assessment of Gastroprotective Mechanisms of Action in Human Cells

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