Discovery of prenylated dihydrostilbenes in Glycyrrhiza uralensis leaves by UHPLC-MS using neutral loss scan

Stilbenes are a small family of polyphenolic secondary metabolites that can be found in several distantly related plant species. These compounds act as phytoalexins, playing a crucial role in plant defense against phytopathogens, as well as being involved in the adaptation of plants to abiotic environmental factors. Among stilbenes, trans-resveratrol is certainly the most popular and extensively studied for its health properties. In recent years, an increasing number of stilbene compounds were subjected to investigations concerning their bioactivity. This review presents the most updated knowledge of the stilbene biosynthetic pathway, also focusing on the role of several environmental factors in eliciting stilbenes biosynthesis. The effects of ultraviolet radiation, visible light, ultrasonication, mechanical stress, salt stress, drought, temperature, ozone, and biotic stress are reviewed in the context of enhancing stilbene biosynthesis, both in planta and in plant cell and organ cultures. This knowledge may shed some light on stilbene biological roles and represents a useful tool to increase the accumulation of these valuable compounds.

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“…(Euphorbiaceae) [135,136], Glycyrrhiza spp. [137][138][139][140], peanut [141][142][143][144][145][146], and mulberry [147].…”

Section: Prenylationmentioning

confidence: 99%

Impact of Environmental Factors on Stilbene Biosynthesis

Valletta

Iozia

Leonelli

2021

Plants

119

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“…The calculated ΔH and ΔG were 17.1 and 4.5 kcal mol −1 , respectively. Isobutene (56 Da) elimination has also been reported for prenylated compounds, 67 so it cannot be considered specific for a tert ‐butyl group.…”

Section: Resultsmentioning

confidence: 99%

Electrospray ionization tandem mass spectrometry of 4‐aryl‐3,4‐dihydrocoumarins

Dias,

Santos,

Filho

et al. 2024

J Mass Spectrom

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We have investigated the gas‐phase fragmentation reactions of 11 synthetic 4‐aryl‐3,4‐dihydrocoumarins by electrospray ionization tandem mass spectrometry (ESI‐MS/MS) on a quadrupole‐time‐of flight (Q‐TOF) hybrid mass spectrometer. We have also estimated thermochemical data for the protonated coumarins (precursor ion A) and product ion structures by computational chemistry at a B3LYP level of theory to establish the ion structures and to rationalize the fragmentation pathways. The most abundant ions in the product ion spectra of coumarins 1–11 resulted from C8H8O2, CO2, C4H4O3, C8H10O3, C8H8O2, and CH3OH eliminations through retro‐Diels–Alder (RDA) reactions, remote hydrogen rearrangements (β‐eliminations), and β‐lactone ring contraction. Although the investigated coumarins shared most of the fragmentation pathways, formation of a benzylic product ion and its corresponding tropylium ion was diagnostic of the substituents at ring C. The thermochemical data revealed that the nature and position of the substituents at ring C played a key role in the formation of this product ion and determined its relative intensity in the product ion spectrum. The results of this study contribute to knowledge of the gas‐phase ion chemistry of this important class of organic compounds.

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“…NLS mode has been employed in the screening of different metabolites, such as, identification of prenylated dihydrostilbenes in Glycyrrhiza uralensis Fisch. leaves [24], detection and quantification of sulfated flavonoids in plants [25], detection of diacylglycerols by 2,4-difluorophenyl isocyanate derivatization in cells [26] and of metabolites with carboxyl group by N,N-dimethylethylenediamine derivatization in plasma of smokers and non-smokers [27]. To the best of our knowledge, there are no studies about DEEMM derivatives detected with NLS mode.…”

Section: Introductionmentioning

confidence: 99%