A fresh look at natural tropolonoids

Bentley, Ronald

doi:10.1039/b711474e

Cited by 161 publications

(129 citation statements)

References 156 publications

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“…16 In general, the natural and synthetic tropolones have been reported to show antibacterial, antifungal, insecticidal, antiviral and antitumor activities, as well as inhibiting enzymes such as aminoglycoside-2 00 -O-adenyltransferase, 17 metalloprotease 18 and HIV-1 reverse transcriptase-associated ribonuclease H. 19 The inhibitory mechanisms of tropolones were thought to reflect their ability to form a complex with divalent cations. 20 Among these compounds, hinokitiol and its related synthetic derivatives have been reported to show antimalarial activity, whereas the synthetic benzotropolone derivatives 15,21,22 and a dihydrotroplone antibiotic, cordytropolone, 23 have also been reported to show moderate or weak antimalarial activities in vitro. However, this paper represents the first report of the antimalarial activity of carboxytropolones, such as puberulic acid.…”

Section: Discussionmentioning

confidence: 99%

In vitro and in vivo antimalarial activity of puberulic acid and its new analogs, viticolins A–C, produced by Penicillium sp. FKI-4410

et al. 2010

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In the course of screening for antimalarial agents, five tropolone compounds were isolated from the culture broth of Penicillium sp. FKI-4410. Two were known compounds, puberulic acid and stipitatic acid. Three were new analogs of puberulic acid, designated viticolins A-C. Among them, puberulic acid exhibited potent antimalarial inhibition, with IC 50 values of 0.01 lg ml À1 against chloroquine-sensitive and -resistant Plasmodium falciparum strains in vitro. Furthermore, puberulic acid showed weak cytotoxicity against human MRC-5 cells, with an IC 50 value of 57.2 lg ml À1 . The compound also demonstrated a therapeutic effect in vivo, which compared well against the currently used antimalarial drugs, and thus shows promise as a leading candidate for development into a new antimalarial compound.

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Section: Discussionmentioning

confidence: 99%

In vitro and in vivo antimalarial activity of puberulic acid and its new analogs, viticolins A–C, produced by Penicillium sp. FKI-4410

et al. 2010

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“…secondary) metabolites, many of which are named after the Thuja genus. For example, thujaplicins are ring-expanded monoterpenoids with strong antifungal properties that provide heartwood rot resistance (DeBell et al, 1999;Daniels and Russell, 2007;Bentley, 2008). Thujic acid and related lignans serve a similar function, making the wood of T. plicata highly suitable for outdoor use (Taylor et al, 2006;Morris and Stirling, 2012).…”

Section: Discussionmentioning

confidence: 99%

Identification of Genes in Thuja plicata Foliar Terpenoid Defenses

et al. 2013

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Thuja plicata (western redcedar) is a long-lived conifer species whose foliage is rarely affected by disease or insect pests, but can be severely damaged by ungulate browsing. Deterrence to browsing correlates with high foliar levels of terpenoids, in particular the monoterpenoid α-thujone. Here, we set out to identify genes whose products may be involved in the production of α-thujone and other terpenoids in this species. First, we generated a foliar transcriptome database from which to draw candidate genes. Second, we mapped the storage of thujones and other terpenoids to foliar glands. Third, we used global expression profiling to identify more than 600 genes that are expressed at high levels in foliage with glands, but can either not be detected or are expressed at low levels in a natural variant lacking foliar glands. Fourth, we used in situ RNA hybridization to map the expression of a putative monoterpene synthase to the epithelium of glands and used enzyme assays with recombinant protein of the same gene to show that it produces sabinene, the monoterpene precursor of α-thujone. Finally, we identified candidate genes with predicted enzymatic functions for the conversion of sabinene to α-thujone. Taken together, this approach generated both general resources and detailed functional characterization in the identification of genes of foliar terpenoid biosynthesis in T. plicata.

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“…4,5 Given the case, an effective approach would become available en route to functionalized benzocycloheptenes, 6 which are embedded as a structural motif in some biologically active natural products ( Figure 1). 7 Herein, we report an affirmative answer to this scenario, opening a route to highly substituted benzocycloheptenes.…”

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confidence: 93%