Peroxidase 4-Based Enzymatic Synthesis of Stilbene Oligomers in Methyl Jasmonate-Elicited Grapevine Cell Suspensions.

Stilbenes are specialized metabolites that are particularly abundant in species. Although the biosynthetic pathways of stilbenes have been well-characterized, the role of specific peroxidases in stilbene oligomerization remains to be investigated. In this study, we used grapevine cell cultures to characterize the functional role of peroxidase 4 (VvPRX4) in the production of resveratrol oligomers after elicitation with methyl jasmonate (MeJA).

Optimize, Modulate, and Scale-up Resveratrol and Resveratrol Dimers Bioproduction in L. Cell Suspension from Flasks to 20 L Bioreactor.

Resveratrol and its oligomers are biologically active compounds. This work brings new insights for the bioproduction of -resveratrol with three dimers, pallidol, -ε-viniferin, and -δ-viniferin, in cell suspension of . Conditions of elicitation by methyl jasmonate were optimized for the production of stilbenes using statistical design of experiment.

Cytotoxicity of Labruscol, a New Resveratrol Dimer Produced by Grapevine Cell Suspensions, on Human Skin Melanoma Cancer Cell Line HT-144.

A new resveratrol dimer () called labruscol, has been purified by centrifugal partition chromatography of a crude ethyl acetate stilbene extract obtained from elicited grapevine cell suspensions of L. cultured in a 14-liter stirred bioreactor. One dimensional (1D) and two dimensional (2D) nuclear magnetic resonance (NMR) analyses including ¹H, C, heteronuclear single-quantum correlation HSQC), heteronuclear multiple bond correlation (HMBC), and correlation spectroscopy (COSY) as well as high-resolution electrospray ionisation mass spectrometry (HR-ESI-MS) were used to characterize this compound and to unambiguously identify it as a new stilbene dimer, though its relative stereochemistry remained unsolved.

Anti-Cancer Activity of Resveratrol and Derivatives Produced by Grapevine Cell Suspensions in a 14 L Stirred Bioreactor.

In the present study, resveratrol and various oligomeric derivatives were obtained from a 14 L bioreactor culture of elicited grapevine cell suspensions (Vitis labrusca L.). The crude ethyl acetate stilbene extract obtained from the culture medium was fractionated by centrifugal partition chromatography (CPC) using a gradient elution method and the major stilbenes contained in the fractions were subsequently identified by using a C-NMR-based dereplication procedure and further 2D NMR analyses including HSQC, HMBC, and COSY.

Enhanced Stilbene Production and Excretion in Vitis vinifera cv Pinot Noir Hairy Root Cultures.

Stilbenes are defense molecules produced by grapevine in response to stresses including various elicitors and signal molecules. Together with their prominent role in planta, stilbenes have been the center of much attention in recent decades due to their pharmaceutical properties. With the aim of setting up a cost-effective and high purity production of resveratrol derivatives, hairy root lines were established from cv Pinot Noir 40024 to study the organ-specific production of various stilbenes.

C NMR and LC-MS Profiling of Stilbenes from Elicited Grapevine Hairy Root Cultures.

Resveratrol and related oligostilbenes are defense molecules produced by grapevine in response to stresses including various elicitors or signal molecules. Together with their prominent role in planta, these compounds have been the center of much attention in recent decades due to their pharmacological properties. The cost-effective production of resveratrol derivatives such as viniferins or more structurally complex stilbene oligomers remains a challenging task.

Modulation of phytoalexin biosynthesis in engineered plants for disease resistance.

Phytoalexins are antimicrobial substances of low molecular weight produced by plants in response to infection or stress, which form part of their active defense mechanisms. Starting in the 1950's, research on phytoalexins has begun with biochemistry and bio-organic chemistry, resulting in the determination of their structure, their biological activity as well as mechanisms of their synthesis and their catabolism by microorganisms. Elucidation of the biosynthesis of numerous phytoalexins has permitted the use of molecular biology tools for the exploration of the genes encoding enzymes of their synthesis pathways and their regulators.

Engineering microbial cells for the biosynthesis of natural compounds of pharmaceutical significance.

Microbes constitute important platforms for the biosynthesis of numerous molecules of pharmaceutical interest such as antitumor, anticancer, antiviral, antihypertensive, antiparasitic, antioxidant, immunological agents, and antibiotics as well as hormones, belonging to various chemical families, for instance, terpenoids, alkaloids, polyphenols, polyketides, amines, and proteins. Engineering microbial factories offers rich opportunities for the production of natural products that are too complex for cost-effective chemical synthesis and whose extraction from their originating plants needs the use of many solvents. Recent progresses that have been made since the millennium beginning with metabolic engineering of microorganisms for the biosynthesis of natural products of pharmaceutical significance will be reviewed.

Metabolic engineering of yeast and plants for the production of the biologically active hydroxystilbene, resveratrol.

Resveratrol, a stilbenic compound deriving from the phenyalanine/polymalonate route, being stilbene synthase the last and key enzyme of this pathway, recently has become the focus of a number of studies in medicine and plant physiology. Increased demand for this molecule for nutraceutical, cosmetic and possibly pharmaceutic uses, makes its production a necessity. In this context, the use of biotechnology through recombinant microorganisms and plants is particularly promising.

Biosynthesis, metabolism, molecular engineering, and biological functions of stilbene phytoalexins in plants.

Stilbenic compounds recently have become the focus of a number of studies in medicine and plant physiology as well as have emerged as promising molecules that potentially affect human health. Stilbenes are relatively simple compounds synthesized by plants and deriving from the phenyalanine/polymalonate route, the last and key enzyme of this pathway being stilbene synthase. Here, we review the biological significance of stilbenes in plants together with their biosynthesis pathway and their metabolism both by fungi and in planta.

Bioproduction of resveratrol and stilbene derivatives by plant cells and microorganisms.

Trans-resveratrol is a phenolic plant compound that has been recognized for its benefits on human health. Currently, increasing demand for trans-resveratrol for nutraceutical, cosmetic, and putatively pharmaceutic uses makes its production from sustainable sourcing a necessity. In this context, the use of biotechnology through recombinant microorganisms and plant cell suspensions is particularly promising because it represents a reliable alternative method of trans-resveratrol production under controlled conditions.