Antifungal and Antibacterial Chalcones from<i>Myrica serrata</i>

Gafner, Stefan; Wolfender, Jean‐Luc; Mavi, S.; Hostettmann, Kurt

doi:10.1055/s-2006-957804

Cited by 70 publications

(46 citation statements)

References 3 publications

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“…Among the compounds described here, four were previously identified in other Myricaceae species as follows: demethoxymatteucinol in Morella pensylvanica, a species with broad symbiont specificity, MyB, MyE, and MyD in Morella serrata, and MyB in Comptonia peregrina (both hosts with unknown symbiotic specificity) (19,64). The other compounds (MyA, MyP, uvangoletin, and demethoxymatteucinol-7-methyl ether) have been described only in M. gale among actinorhizal plants.…”

Section: Discussionmentioning

confidence: 76%

Differential Effects of Rare Specific Flavonoids on Compatible and Incompatible Strains in the Myrica gale - Frankia Actinorhizal Symbiosis

Popovici

Comte

Bagnarol

et al. 2010

Appl Environ Microbiol

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Plant secondary metabolites, and specifically phenolics, play important roles when plants interact with their environment and can act as weapons or positive signals during biotic interactions. One such interaction, the establishment of mutualistic nitrogen-fixing symbioses, typically involves phenolic-based recognition mechanisms between host plants and bacterial symbionts during the early stages of interaction. While these mechanisms are well studied in the rhizobia-legume symbiosis, little is known about the role of plant phenolics in the symbiosis between actinorhizal plants and Frankia genus strains. In this study, the responsiveness of Frankia strains to plant phenolics was correlated with their symbiotic compatibility. We used Myrica gale, a host species with narrow symbiont specificity, and a set of compatible and noncompatible Frankia strains. M. gale fruit exudate phenolics were extracted, and 8 dominant molecules were purified and identified as flavonoids by high-resolution spectroscopic techniques. Total fruit exudates, along with two purified dihydrochalcone molecules, induced modifications of bacterial growth and nitrogen fixation according to the symbiotic specificity of strains, enhancing compatible strains and inhibiting incompatible ones. Candidate genes involved in these effects were identified by a global transcriptomic approach using ACN14a strain whole-genome microarrays. Fruit exudates induced differential expression of 22 genes involved mostly in oxidative stress response and drug resistance, along with the overexpression of a whiB transcriptional regulator. This work provides evidence for the involvement of plant secondary metabolites in determining symbiotic specificity and expands our understanding of the mechanisms, leading to the establishment of actinorhizal symbioses.Over the course of evolution, plants have developed many strategies to adapt to their environment and manage their biotic interactions. The production of secondary metabolites is an important tool in many of these strategies. In particular, secondary metabolites are involved in plant-microbe interactions both as weapons in plant defense mechanisms and as early signals in mutualistic as well as pathogenic relationships (22). For example, sesquiterpenes and flavonoids are involved in the early steps of arbuscular mycorrhizal symbiosis (1, 62). Similarly, in the early stages of the rhizobia-legume symbiosis, recognition of host flavonoids enhances rhizospheric competitiveness and root colonization and is the basic mechanism through which rhizobia induce the transcription of nod genes, leading to root hair deformation and nodulation in the plant tissues (13,49,55).Actinorhizal symbiosis is a less well-known nitrogen-fixing interaction, resulting from the association between the actinobacterium Frankia and plants belonging to eight dicotyledonous families collectively called "actinorhizal": Betulaceae, Myricaceae, Rosaceae, Datiscaceae, Elaeagnaceae, Coriariaceae, Casuarinaceae, and Rhamnaceae (8). Due to the nitrogen-fixing...

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Section: Discussionmentioning

confidence: 76%

Differential Effects of Rare Specific Flavonoids on Compatible and Incompatible Strains in the Myrica gale - Frankia Actinorhizal Symbiosis

Popovici

Comte

Bagnarol

et al. 2010

Appl Environ Microbiol

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“…An uncommon feature is the additional C-methylation in 1 and 2; these compounds have been previously isolated from the leaves of this plant and reported to have antidiabetic properties (Resurreccion-Magno et al, 2005), antibacterial (Gafner, Wolfender, Mavi & Hostettmann, 1996), spasmolitic (Amor et al, 2005;Ghayur et al, 2006) properties, and inhibited prolyl endopeptidase (Amor, et al, 2004). This is the first report of the isolation of chalcone 3 from S. samarangense.…”

Section: Resultsmentioning

confidence: 80%

Cytotoxic chalcones and antioxidants from the fruits of Syzygium samarangense (Wax Jambu)

et al. 2008

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Bioassay-guided fractionation of the methanolic extracts of the pulp and seeds of the fruits of Syzygium samarangense Merr. & Perry (Blume) led to the identification of four cytotoxic compounds and eight antioxidants on the basis of HPLC-PDA analysis, MS, and various NMR spectroscopic techniques. Three C-methylated chalcones, 2′,4′-dihydroxy-3′,5′-dimethyl-6′-methoxychalcone (1), 2′,4′-dihydroxy-3′-methyl-6′-methoxychalcone (stercurensin, 2), and 2′,4′-dihydroxy-6′-methoxychalcone (cardamonin, 3), were isolated and displayed cytotoxic activity (IC 50 = 10, 35, and 35 μM, respectively) against the SW-480 human colon cancer cell line. Also a number of known antioxidants were obtained including six quercetin glycosides: reynoutrin (4), hyperin (5), myricitrin (6), quercitrin (7), quercetin (9), and guaijaverin (10), one flavanone: (S)-pinocembrin (8), and two phenolic acids: gallic acid (11) and ellagic acid (12).

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“…Chalcone has been found to exert toxicity against 5 fungal pathogens (Colletotrichum falcatum, Curvularia pallescens, Ceratocystis paradoxa, Fusarium moniliforme, Periconia atropurpurea and Ustilago scitaminea), being even more active than commercial fungicides (Rao et al, 1994). Two natural chalcones isolated from the leaves of Myrica serrata, 2',4'-dihydroxy-3',5'-dimethyl-6'-methoxychalcone and stercurensin, showed a strong inhibitory effect on the growth of Cladosporium cucumerinum, a fungus that typically affects cucumber (Gafner et al, 1996). The 2',4'-dihydroxy-3'-methoxychalcone and the 2',4'-dihydroxychalcone isolated from Zuccagnia punctata (Fabaceae) were found to be active against the pathogenic fungi Phomopsis longicolla, Alternaria alternate, Fusarium equiseti, F. graminearum, F. verticillioides, Colletotrichum truncatum and Sclerotium bataticola, and if used at the concentration of 6.25 µg/mL completely inhibited the growth of P. longicolla and C. truncatum (Svetaz et al, 2004;Jimenez et al, 2014).…”

Section: Fungicidesmentioning

confidence: 99%

Biological Activities and Novel Applications of Chalcones

et al. 2016

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-This review provides information on the biological activities of chalcones (whether natural or synthetic derivatives) on different organisms, as well as an overview of the functions and possible new applications of these plant secondary metabolites on crop protection, as eco-friendly pesticides and weed control agents. Naturally occurring chalcones have been used in traditional medicine for many years; however, recent scientific advances have shown that these molecules have a broad range of biological activities in a variety of organisms. A review on the major sources of chalcones and the main molecular events involved in the modes of action of these natural products is achieved. Chalcones are molecules with a broad spectrum of biological activities, which are of great interest in agriculture to control weeds and unwanted pests.Keywords: mode of action, secondary metabolites, crop protection, pesticide, fungicide, antiviral, phytotoxicity. RESUMO -Esta avaliação fornece informações sobre as atividades biológicas de chalconas (quer derivados naturais ou sintéticos) em diferentes organismos, bem como uma visão geral das funções e eventuais novas aplicações desses metabólitos secundários de plantas em proteção de cultivos e pesticidas orgânicos e para controlar as plantas daninhas. Durante muitos anos têm sido utilizadas na medicina tradicional chalconas de ocorrência natural; no entanto, os recentes avanços científicos têm mostrado que essas moléculas têm vasta gama de atividades biológicas em uma variedade de organismos. Este estudo permite ter uma ideia das principais fontes de chalconas e dos eventos moleculares envolvidos nos principais mecanismos de ação desses produtos naturais. As chalconas são moléculas com um largo espectro de atividade biológica, de grande interesse na agricultura para controlar plantas daninhas e pragas indesejadas.Palavras-chave: modo de ação, metabólitos secundários, proteção de cultivos, pesticida, fungicida, antiviral, fitotoxicidade.

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Antifungal and Antibacterial Chalcones fromMyrica serrata

Cited by 70 publications

References 3 publications

Differential Effects of Rare Specific Flavonoids on Compatible and Incompatible Strains in the Myrica gale - Frankia Actinorhizal Symbiosis

Differential Effects of Rare Specific Flavonoids on Compatible and Incompatible Strains in the Myrica gale - Frankia Actinorhizal Symbiosis

Cytotoxic chalcones and antioxidants from the fruits of Syzygium samarangense (Wax Jambu)

Biological Activities and Novel Applications of Chalcones

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