Phytostilbenes as agrochemicals: biosynthesis, bioactivity, metabolic engineering and biotechnology

Jeandet, Philippe; Vannozzi, Alessandro; Sobarzo‐Sánchez, Eduardo; Uddin, Sahab; Bru, Roque; Martínez-Márquez, Ascensión; Clément, Christophe; Cordelier, Sylvain; Manayi, Azadeh; Nabavi, Seyed Fazel; Rasekhian, Mahsa; Batiha, Gaber El‐Saber; Khan, Haroon; Morkunas, Iwona; Belwal, Tarun; Jiang, Jingjie; Koffas, Mattheos

doi:10.1039/d0np00030b

Cited by 74 publications

(82 citation statements)

References 494 publications

(612 reference statements)

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“…The synthesis of resveratrol derivatives and their novel functional properties have been a research hotspot recently. Resveratrol (RE; 3,4ʹ,5 trihydroxystilbene) is a C6-C2-C6 stilbene natural phenolic compound with three hydroxyl groups [1] that is found in more than 70 plants and plays an important role in the defense against pathogens, infections, injury, and abiotic stress [1,2]. Resveratrol presents numerous therapeutic benefits, in-cluding anti-inflammatory, antioxidant, anti-platelet, anti-hyperlipidemia, immune-modulator, anti-carcinogenic, cardioprotective, vasorelaxant, and neuroprotective properties.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Short-Chain-Fatty-Acid Resveratrol Esters and Their Antioxidant Properties

et al. 2021

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To expand the applications and enhance the stability and bioactivity of resveratrol (RE), and to simultaneously include the potential health benefits of short chain fatty acids (SCFA) esters of RE were prepared by Steglich reactions with acetic, propionic, and butyric acids, respectively. RE and the esterified RE-SCFA products (including RAE, RPE, and RBE) were analyzed using nuclear magnetic resonance (NMR), Fourier-transform infrared (FTIR) spectroscopy, thermogravimetric analysis (TGA), differential thermal analysis (DTA), and liquid chromatography–mass spectrometry (LC–MS). The FTIR and 13C NMR spectra of the esterified products included ester-characteristic peaks at 1751 cm−1 and 171 ppm, respectively. Moreover, the peaks in the range of 1700 to 1600 cm−1 in the FTIR spectra of the esterified products indicated that the esterification of RE-SCFA was successful. The TGA results revealed that the RE-SCFA esters decomposed at lower temperatures than RE. The peaks in the LC–MS profiles of the esterified products indicated the formation of mono- and diesters, and the calculated monoester synthesis rates ranged between 45.81 and 49.64%. The RE esters inhibited the Cu2+-induced low-density lipoprotein oxidation reaction, exhibited antioxidant activity in bulk oil, and effectively inhibited the hydroxyl radical-induced DNA scission. Moreover, the RE-SCFA esters had better hydrogen peroxide scavenging activity than RE. Our results are the first in the literature to successfully including short chain fatty acids in the esters of resveratrol, and the products could be used as a functional food ingredient in processed foods or can be used as dietary supplements to promote health.

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Section: Introductionmentioning

confidence: 99%

Synthesis of Short-Chain-Fatty-Acid Resveratrol Esters and Their Antioxidant Properties

et al. 2021

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“…The phenylalanine is known as the primary substrate for the biosynthesis of flavonoids and stilbenes via the phenylpropanoid pathway in most plants such as grapes (Jeandet et al, 2021;Lu et al, 2021). The biosynthesis of resveratrol was achieved through a small branch of the phenylpropanoid pathway and is considered as a competitive extension of the branch of the flavonoids (Vannozzi et al, 2018;Andi et al, 2021;Jeandet et al, 2021). Upstream of the phenylpropanoid pathway, the expression levels of PAL, C4H, 4CL, and STS genes were closely related to the contents of resveratrol.…”

Section: Discussionmentioning

confidence: 99%

“…These transcripts might be involved in the metabolism of resveratrol. Furthermore, CHS, a key enzyme of the flavonoid pathway, is closely related to STS and also affects the resveratrol content, because both enzymes compete for the same substrate and control the entry points into the flavonoid and stilbene pathways, respectively (Andi et al, 2021;Jeandet et al, 2021).…”

Section: Discussionmentioning

confidence: 99%

“…Transcriptome analysis provides an insight into the PAL, 4CL, and STS expression profiles showing that the concentration of their transcripts increased from veraison to maturity, as well as the content of resveratrol also increases in the grape (Gatto et al, 2008). Meanwhile, the competition between STS and chalcone synthase (CHS) for the same substrates is the factor that affects the accumulation of resveratrol (Jeandet et al, 1995;Gatto et al, 2008;Yin et al, 2016;Lu et al, 2021).…”

Section: Introductionmentioning

confidence: 99%

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Transcriptomic and Weighted Gene Co-expression Correlation Network Analysis Reveal Resveratrol Biosynthesis Mechanisms Caused by Bud Sport in Grape Berry

Feng

Zhou

et al. 2021

Front. Plant Sci.

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Resveratrol is a natural polyphenol compound produced in response to biotic and abiotic stresses in grape berries. However, changes in resveratrol caused by bud sport in grapes are scarcely reported. In this study, trans-resveratrol and cis-resveratrol were identified and quantified in the grape berries of ‘Summer Black’ and its bud sport ‘Nantaihutezao’ from the veraison to ripening stages using ultra performance liquid chromatography-high resolution tandem mass spectrometry (UPLC-HRMS). We found that bud sport accumulates the trans-resveratrol earlier and increases the contents of cis-resveratrol in the earlier stages but decreases its contents in the later stages. Simultaneously, we used RNA-Seq to identify 51 transcripts involved in the stilbene pathways. In particular, we further identified 124 and 19 transcripts that negatively correlated with the contents of trans-resveratrol and cis-resveratrol, respectively, and four transcripts encoding F3'5'H that positively correlated with the contents of trans-resveratrol by weighted gene co-expression network analysis (WGCNA). These transcripts may play important roles in relation to the synergistic regulation of metabolisms of resveratrol. The results of this study can provide a theoretical basis for the genetic improvement of grapes.

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“…Furthermore, piceatannol exerts positive effects on human dermal cells by inhibiting melanogenesis and promoting collagen synthesis, and these effects are more pronounced than those of resveratrol (Matsui et al, 2010 ; Seyed et al, 2016 ). Other stilbene derivatives also reportedly exhibit a variety of biological activities (Jeandet et al, 2021 ).…”

Section: Introductionmentioning

confidence: 99%

Diversity and characteristics of culturable endophytic bacteria from Passiflora edulis seeds

Ishida

Furuya

2021

MicrobiologyOpen

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Defense compounds generally inhibit microbial colonization of plants. In this study, we examined the presence of endophytes in Passiflora edulis seeds that accumulate resveratrol and piceatannol at extremely high levels as defense compounds. Interestingly, although no microbial colonies appeared on an agar growth medium from the cut or homogenized seeds, colonies were generated from cut seedlings derived from the seeds. A total of 19 bacterial strains were isolated, of which 15 were classified as Gram‐positive. As we hypothesized that extremely high levels of piceatannol in the seeds would inhibit the growth of endophytes cultured directly from the seeds, we examined the antimicrobial activity of this compound against the isolated bacteria. Piceatannol exerted bacteriostatic rather than bactericidal effects on most of the bacteria tested. These results suggest that the bacteria remain static in the seeds due to the presence of piceatannol and are transmitted to the seedlings during the germination process, enabling colonies to be established from the seedlings on the agar medium. We also investigated the biocatalytic activity of the isolated bacteria toward resveratrol and piceatannol. One bacterium, Brevibacterium sp. PE28‐2, converted resveratrol and piceatannol to their respective derivatives. This strain is the first endophyte shown to exhibit such activity.

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Phytostilbenes as agrochemicals: biosynthesis, bioactivity, metabolic engineering and biotechnology

Abstract: Although constituting a limited chemical family, phytostilbenes represent an emblematic group of molecules among natural compounds.

Cited by 74 publications

References 494 publications

Synthesis of Short-Chain-Fatty-Acid Resveratrol Esters and Their Antioxidant Properties

Synthesis of Short-Chain-Fatty-Acid Resveratrol Esters and Their Antioxidant Properties

Transcriptomic and Weighted Gene Co-expression Correlation Network Analysis Reveal Resveratrol Biosynthesis Mechanisms Caused by Bud Sport in Grape Berry

Diversity and characteristics of culturable endophytic bacteria from Passiflora edulis seeds

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