Structure, Chemical Analysis, Biosynthesis, Metabolism, Molecular Engineering, and Biological Functions of Phytoalexins

Jeandet, Philippe

doi:10.3390/molecules23010061

Cited by 13 publications

(8 citation statements)

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“…e antibacterial activity of phytoalexins has largely been confined to isoflavonoids from Fabaceae, with one report of this activity of wyerone in comparison with other isoflavonoid phytoalexins [21] was published. Moreover, most of the antimicrobial activity studies focused on antifungal rather than antibacterial activity [3,4]. In the present study, we tried to explore more on this issue regarding three of these phytoalexins, wyerone, wyerone acid, and wyerone epoxide against five Gram-positive and two Gram-negative bacteria.…”

Section: Introductionmentioning

confidence: 99%

“…One example of the defense mechanisms is the accumulation of antimicrobial secondary metabolites, which are called the phytoalexins [1,2]. ese phytoalexins are synthesized by plants as a result of infections (fungal, bacterial, or viral) [3,4] or due to other forms of stress, which could be chemical elicitors (e.g., mercury salts, copper) or physical events like UV light [5]. Fabaceae plants usually synthesize certain isoflavonoid phytoalexins, but certain species accumulate nonisoflavanoid compounds instead of or in addition to isoflavanoid [6,7].…”

Section: Introductionmentioning

confidence: 99%

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Biogenetic Conversion of Wyerone and Dihydrowyerone into Wyerone Epoxide in Vicia faba Cotyledons and Screening of Antibacterial Activity

Al-Douri

Haddadin

Shakya

et al. 2018

Journal of Chemistry

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Background. Vicia faba is a plant that belongs to the family Fabaceae. Cotyledons of this plant produce compounds called phytoalexins as a result of fungal and bacterial infection or stress factors. The phytoalexins are furanoacetylenic compounds. They include wyerone, wyerol, wyerone acid, their dihydro derivatives, and wyerone epoxide. These compounds have antimicrobial activities mainly against fungi. Objective. The purpose of this study was to elucidate the biogenetic conversion of wyerone and dihydrowyerone to wyerone epoxide in V. faba and to investigate the antibacterial activities of some of these phytoalexins. Materials and Methods. Seeds of Vicia faba were used. Labelled wyerone and dihydrowyerone were obtained by treating CuCl2-induced cotyledons with sodium (2-14C) acetate and separated by TLC and HPLC. Labelled wyerone and dihydrowyerone were then applied to induced bean cotyledons to establish any possible interconversion to wyerone epoxide. Antibacterial activity of wyerone, wyerone acid, and wyerone epoxide was investigated by disc diffusion test against a panel of microorganisms. Zones of inhibition were reported. Results. The radiolabeling studies showed that 12.4% of 14C-wyerone, and 6.01% of 14C-dihydrowyerone were incorporated into wyerone epoxide. This indicates that wyerone epoxide was most probably derived from wyerone and dihydrowyerone. In addition, a new compound, 11-hydroxywyerone was isolated for the first time. Additionally, this study showed that wyerone, wyerone epoxide, and wyerone acid had no antibacterial activity against Gram-negative bacteria but were active against Gram-positive bacteria.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Biogenetic Conversion of Wyerone and Dihydrowyerone into Wyerone Epoxide in Vicia faba Cotyledons and Screening of Antibacterial Activity

Al-Douri

Haddadin

Shakya

et al. 2018

Journal of Chemistry

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“…Many of these compound groups are secondary metabolites, and plants have acquired the ability to produce a variety of antimicrobial secondary metabolites in their interactions with microorganisms. Phytoanticipin and phytoalexin are antimicrobial compounds that are synthesized inducibly or not, respectively, and the same compound may act as a phytoanticipin or phytoalexin depending on plant type and organs (VanEtten et al 1994 ; Morrissey and Osbourn 1999 ; Jeandet 2018 ).…”

Section: Introductionmentioning

confidence: 99%

Measurements of Antibacterial Activity of Seed Crude Extracts in Cultivated Rice and Wild Oryza Species

Yoshida

Nosaka-T

Yoshikawa

et al. 2022

Rice

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Seeds are continuously exposed to a wide variety of microorganisms in the soil. In addition, seeds contain large amounts of carbon and nitrogen sources that support initial growth after germination. Thus, seeds in the soil can easily promote microbial growth, and seeds are susceptible to decay. Therefore, seed defense against microorganisms is important for plant survival. Seed-microbe interactions are also important issues from the perspective of food production, in seed quality and shelf life. However, seed-microbe interactions remain largely unexplored. In this study, we established a simple and rapid assay system for the antibacterial activity of rice seed crude extracts by colorimetric quantification methods by the reduction of tetrazolium compound. Using this experimental system, the diversity of effects of rice seed extracts on microbial growth was analyzed using Escherichia coli as a bacterial model. We used collections of cultivated rice, comprising 50 accessions of Japanese landraces, 52 accessions of world rice core collections, and of 30 wild Oryza accessions. Furthermore, we attempted to find genetic factors responsible for the diversity by genome-wide association analysis. Our results demonstrate that this experimental system can easily analyze the effects of seed extracts on bacterial growth. It also suggests that there are various compounds in rice seeds that affect microbial growth. Overall, this experimental system can be used to clarify the chemical entities and genetic control of seed-microbe interactions and will open the door for understanding the diverse seed-microbe interactions through metabolites.

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“…OGs, as a prebiotic, promote gut health and exhibit some biological activities, such as antitumor, immunoregulation, and antibacterial activities. − Therefore, OGs, as a functional food and drug molecule, are beneficial to human health. Meanwhile, OGs, as a classic damage-associated molecular pattern, elicit a wide array of defense responses and regulate plant growth and development. , Recently, the regulation and mechanism of OGs have become research hot spots in the plant immunity field. − Therefore, OGs could be the most potent plant elicitors for protecting plants from pests and diseases in the future.…”

Section: Introductionmentioning

confidence: 99%

A Highly Efficient Biocatalytic Conversion of Renewable Pectic Polysaccharide Biomass into Bioactive Oligogalacturonides

Yang

Tan

et al. 2021

ACS Food Sci. Technol.

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The quest for an efficient biodegradation of pectic polysaccharides into sustainable oligogalacturonide (OG) products for a recent bioactivity study and application is currently underway. This study reported highly efficient degradation of pectin into OGs (DP2–DP10) by a polygalacturonase (i.e., AnPG28A from Aspergillus niger). The activity of AnPG28A toward low-methoxyl pectin reached 42897 units/mL, and the protein concentration was 7.7 g/L after 96 h, the highest of the reported values. For further processing of commercial pectins to produce OGs, the physicochemical properties of different kinds of commercial pectins on the market were characterized. The preparation of high-purity OG standards (DP2–DP7) was achieved with polygalacturonic acid as a substrate by high-performance liquid chromatography, which helps the preparation of OG, its usage, and the study of its functional characteristics. Moreover, further OG production pilot experiments were performed on the basis of a response surface methodology. The OG yield was approximately 65% on the pilot scale. AnPG28A has many advantages, such as easy, inexpensive preparation, greenness, and excellent catalytic activity. The high yield and quality of OGs and the sustainability and eco-friendly process support the forthcoming commercialization of the biocatalytic transformation of pectin into high-value-added OGs.

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Structure, Chemical Analysis, Biosynthesis, Metabolism, Molecular Engineering, and Biological Functions of Phytoalexins

Abstract: Plants in their natural environment are facing large numbers of pathogenic microorganisms, mainly fungi and bacteria.[…]

Cited by 13 publications

References 13 publications

Biogenetic Conversion of Wyerone and Dihydrowyerone into Wyerone Epoxide in Vicia faba Cotyledons and Screening of Antibacterial Activity

Biogenetic Conversion of Wyerone and Dihydrowyerone into Wyerone Epoxide in Vicia faba Cotyledons and Screening of Antibacterial Activity

Measurements of Antibacterial Activity of Seed Crude Extracts in Cultivated Rice and Wild Oryza Species

A Highly Efficient Biocatalytic Conversion of Renewable Pectic Polysaccharide Biomass into Bioactive Oligogalacturonides

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