Noduliprevenone: A Novel Heterodimeric Chromanone with Cancer Chemopreventive Potential

Pontius, Alexander; Krick, Anja; Kehraus, Stefan; Foegen, Silke E.; Müller, Michael; Klimo, Karin; Gerhäuser, Clarissa; König, Gabriele M.

doi:10.1002/chem.200801574

Cited by 33 publications

(27 citation statements)

References 27 publications

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“…From the fungus Nodulisporium sp., a further endophyte of a Mediterranean alga, we obtained the heterodimeric polyketide noduliprevenone ( Fig. 13; Pontius et al 2008b). This natural product possesses an unprecedented structure consisting of two uniquely modified xanthone-derived units.…”

Section: Cytotoxic and Chemopreventive Compounds From Marine-derived mentioning

confidence: 99%

Fungal metabolites: structural diversity as incentive for anticancer drug development

et al. 2010

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Natural products play an important role in the development of anticancer drugs. To date, predominantly metabolites from plants and bacteria served as lead structures for anticancer agents. Fungal metabolites and derivatives thereof are much less investigated for their potential in cancer therapy. There are, however, some promising candidates derived from fungi in clinical phases I and II studies. This review gives an overview on the role of natural products in cancer therapy and summarises some of the latest results of our group in this area.

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Section: Cytotoxic and Chemopreventive Compounds From Marine-derived mentioning

confidence: 99%

Fungal metabolites: structural diversity as incentive for anticancer drug development

et al. 2010

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“…[106][107][108]120, and 121 were assayed for cancer chemopreventive activity through modulating drug-metabolizing enzymes, including cytochrome P-450 1A (CYP1A) and quinone reductase (QR). As a result, 98 outstood as the most active inhibitor of CYP1A with an IC 50 value of 3.0 μM, and 106 required a concentration of 5.3 μM to double the specific activity of QR Pontius et al 2008bPontius et al , 2008c Plasmodium falciparum with an IC 50 value of 0.5 μg/mL (1.4 μM), and 114 inhibited Trypanosoma cruzi with an IC 50 value of 1.5 μg/mL (3.8 μM) (Pontius et al 2008a). …”

Section: Structure and Bioactivity Polyketidesmentioning

confidence: 99%

Mycochemistry of marine algicolous fungi

Wang

2016

Fungal Diversity

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Marine algicolous fungi refer to the fungi inhabiting or associated with marine algae, which have attracted a great attention for natural product researchers due to their chemical diversity and biological activity during the past two decades. Up to the end of 2014, a total of 366 new natural products, including polyketides, terpenoids, polyketide-terpenoids, peptides, alkaloids, and shikimate derivatives, have been characterized from them. Among these metabolites, 240 compounds feature cytotoxic, antibacterial, antifungal, antimicroalgal, zooplankton-toxic, antiprotozoal, antioxidative, enzyme-modulatory, and/or some other activities. This review gives a comprehensive coverage of both chemical and biological aspects of the secondary metabolites from marine algicolous fungi.

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“…Eugenitol (2,8-dimethyl-5,7-dihydroxy-chromone) and eugenitine (2,6-dimethyl-5-hydroxy-7-methoxy-chromone), which are important constituents of clove oil, were reported to behave as carcinogenesis inhibitors thanks to their remarkable antioxidant capacity. Noduliprevenone, extracted from marine fungus, is a heterodimeric chromanone reported to act as a cancer chemopreventive agent via modulation of the xenobiotic metabolism [83]. A new chromone derivative isolated from a marine fungus, 2-(hydroxymethyl)-8-methoxy-3-methyl-4H-chromen-4-one (chromanone A), showed to act as a promising inhibitor of several carcinogen metabolising enzymes [70].…”

Section: Chromones As Bioactive Agentsmentioning

confidence: 99%

Bioactive Chromone Derivatives – Structural Diversity

Machado¹,

Marques

2010

CBC

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Chromones (1-benzopyran-4-ones) and chromone derivatives are naturally occurring compounds ubiquitously found in the plant kingdom, and therefore present in representative amounts in a normal human diet. These phytochemicals possess a wide spectrum of biological activities -such as anti-inflammatory, antifungal, antimicrobial, antiviral, antitumour and anticancer -mainly due to their well-recognised antioxidant properties, which stem from their ability to neutralise active forms of oxygen and to cut off free radical processes.Since oxidative stress is known to be the basis for numerous severe pathologies, from cardiovascular and neurodegenerative disorders to cancer, the development of effective antioxidant agents from natural origin (namely dietary constituents) has been the object of vigorous research in the last decade, in view of establishing novel chemopreventive strategies against such diseases which are nowadays the main cause of death worldwide. In fact, the chromone moiety is an important element of pharmacophores of many biologically active molecules displaying diverse medicinal applications.These potential health benefits arising from the antioxidant activity of chromone derivatives are ruled by strict structureactivity/structure-property relationships, which, apart from determining their biological action, modulate their systemic distribution and bioavailability in sites of oxidation within the cell.The present work aims at reviewing the main reported studies on the cytoprotective and anticancer activities of chromone derivatives, with particular emphasis on the effect of their structural features and conformational behaviour on activity, which is the basis of a tailored design of novel chromone-based antioxidants for chemopreventive and chemotherapeutic use.

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Noduliprevenone: A Novel Heterodimeric Chromanone with Cancer Chemopreventive Potential

Cited by 33 publications

References 27 publications

Fungal metabolites: structural diversity as incentive for anticancer drug development

Fungal metabolites: structural diversity as incentive for anticancer drug development

Mycochemistry of marine algicolous fungi

Bioactive Chromone Derivatives – Structural Diversity

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