Chromone and Flavonoid Alkaloids: Occurrence and Bioactivity

Khadem, Shahriar; Marles, Robin J.

doi:10.3390/molecules17010191

Cited by 171 publications

(101 citation statements)

References 45 publications

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“…A similar conclusion can be drawn from the scavenging effects presented by several phenolic compounds and flavonoids [29,33,34]. Chromone 12c proved to be the most active derivative, with IC 50 of 0.29 ± 0.02 and 0.30 ± 0.04 mM, in the absence and in the presence of NaHCO 3 25 mM, respectively (Table 3).…”

Section: Ros and Rns Scavenging Activity Studiessupporting

confidence: 76%

Novel chromone and xanthone derivatives: Synthesis and ROS/RNS scavenging activities

Proença

Albuquerque

Ribeiro

et al. 2016

European Journal of Medicinal Chemistry

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a b s t r a c tChromones and xanthones are oxygen-containing heterocyclic compounds acknowledged by their antioxidant properties. In an effort to develop novel agents with improved activity, a series of compounds belonging to these chemical classes were prepared. Their syntheses involve the condensation of appropriate 2-methyl-4H-chromen-4-ones, obtained via Baker-Venkataraman rearrangement, with (E)-3-(3,4-dimethoxyphenyl)acrylaldehyde to provide the corresponding 2-[(1E,3E)-4-(3,4-dimethoxyphenyl)buta-1,3-dien-1-yl]-4H-chromen-4-ones. Subsequent electrocyclization and oxidation of these compounds led to the synthesis of 1-aryl-9H-xanthen-9-ones. After cleavage of the protecting groups, hydroxylated chromones and xanthones were assessed as scavenging agents against both reactive oxygen species (ROS) [superoxide radical (O 2 -), hydrogen peroxide (H 2 O 2 ), hypochlorous acid (HOCl), singlet oxygen ( 1 O 2 ), and peroxyl radical (ROO )] and reactive nitrogen species (RNS) [nitric oxide ( NO) and peroxynitrite anion (ONOO À )]. Generally, all the tested new hydroxylated chromones and xanthones exhibited scavenger effects dependent on the concentration, with IC 50 values found in the micromolar range. Some of them were shown to have improved scavenging activity when compared with previously reported analogues, allowing the inference of preliminary conclusions on the structure eactivity relationship.

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Section: Ros and Rns Scavenging Activity Studiessupporting

confidence: 76%

Novel chromone and xanthone derivatives: Synthesis and ROS/RNS scavenging activities

Proença

Albuquerque

Ribeiro

et al. 2016

European Journal of Medicinal Chemistry

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“…Rohitukine is a chromane alkaloid ( Figure 11) with anti-inflammatory, immunomodulatory and antitumor properties first characterized as a secondary metabolite of a few tropical plants, Amoora rohituka (=Aphanamixis polystachya) and Dysoxylum binectariferum (Meliaceae), Schumanniophyton (Tetrastigma) magnificum and Schumanniophyton (Assidora) problematicum (Rubiaceae) [319]. This compound has been recently reported as a fermentation product of endophytic strains of F. proliferatum, F. oxysporum and F. solani from D. binectariferum [320,321], and F. fujikuroi from A. rohituka [321].…”

Section: Other Alkaloidsmentioning

confidence: 99%

Plant Bioactive Metabolites and Drugs Produced by Endophytic Fungi of Spermatophyta

2015

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Abstract:It is known that plant-based ethnomedicine represented the foundation of modern pharmacology and that many pharmaceuticals are derived from compounds occurring in plant extracts. This track still stimulates a worldwide investigational activity aimed at identifying novel bioactive products of plant origin. However, the discovery that endophytic fungi are able to produce many plant-derived drugs has disclosed new horizons for their availability and production on a large scale by the pharmaceutical industry. In fact, following the path traced by the blockbuster drug taxol, an increasing number of valuable compounds originally characterized as secondary metabolites of plant species belonging to the Spermatophyta have been reported as fermentation products of endophytic fungal strains. Aspects concerning sources and bioactive properties of these compounds are reviewed in this paper.

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“…Most alkaloids are classifi ed chemically according to the nitrogen-containing ring system (pyrrolidine, piperidine etc.) and their biosynthetic origin, amino acids, amines, alcamides, cyanogenic glycosides, and glucosinolates [Winks & Schimmer, 1999;Paiva et al, 2010;Khadem & Marles, 2012]. Alkaloids have traditionally been of great interest because of their pronounced physiological and medicinal properties (for example, caffeine, nicotine, morphine, atropine, quinine).…”

Section: Nitrogen-containing Compoundsmentioning

confidence: 99%

“…Alkaloids have traditionally been of great interest because of their pronounced physiological and medicinal properties (for example, caffeine, nicotine, morphine, atropine, quinine). Alkaloids are usually classifi ed by their common molecular precursors, such as pyridine (coniine derived from Conium maculatum which is extremely toxic and nicotine, an essential alkaloid from Nicotiana tabacum which is present in a number of other plants belonging to the families Lycopodiaceae, Crassulaceae, Leguminosae, Chepopodiaceae and Compositeae), tropane group (atropine, cocaine), isoquinoline (morphine, codeine), purine (caffeine), and steroids (solanine) [Angelova et al, 2010;Khadem & Marles, 2012]. Most alkaloids are very toxic and, therefore, have the potential function in the chemical defense against herbivores and microorganisms.…”

Section: Nitrogen-containing Compoundsmentioning

confidence: 99%

Current Approaches for Enhanced Expression of Secondary Metabolites as Bioactive Compounds in Plants for Agronomic and Human Health Purposes

Jiménez-García¹,

Vazquez-Cruz²,

Guevara-González³

et al. 2013

Pol. J. Food Nutr. Sci.

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The study of secondary metabolism in plants is an important source for the discovery of bioactive compounds with a wide range of applications. Today these bioactive compounds derived from plants are important drugs such as antibiotics, and agrochemicals substitutes, they also have been economically important as fl avors and fragrances, dyes and pigments, and food preservatives. Many of the drugs sold today are synthetic modifi cations of naturally obtained substances. There is no rigid scheme for classifying secondary metabolites, but they can be divided into different groups based on their chemical components, function and biosynthesis: terpenoids and steroids, fatty acid-derived substances and polyketides, alkaloids, phenolic compounds, non-ribosomal polypeptides and enzyme cofactors. The increasing commercial importance of these chemical compounds has resulted in a great interest in secondary metabolism, particularly the possibility of altering the production of bioactive plant metabolites by means of tissue culture technology and metabolomics. In today's world the use of bioactive compounds derived from plants plays an important role in pharmaceutical applications. This review presents information about these metabolites and their applications as well as their importance in agronomy and bioactive effects on human health as nutraceuticals. This review includes also the new tendencies to produce these bioactive compounds under different stresses conditions such as biotic and abiotic stress that could be included in production systems.

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Chromone and Flavonoid Alkaloids: Occurrence and Bioactivity

Cited by 171 publications

References 45 publications

Novel chromone and xanthone derivatives: Synthesis and ROS/RNS scavenging activities

Novel chromone and xanthone derivatives: Synthesis and ROS/RNS scavenging activities

Plant Bioactive Metabolites and Drugs Produced by Endophytic Fungi of Spermatophyta

Current Approaches for Enhanced Expression of Secondary Metabolites as Bioactive Compounds in Plants for Agronomic and Human Health Purposes

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