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Medicinal plants have always arised an interest because they usually have pharmacological effects, low toxicity and high safety. Herbal preparations can be used both for the prevention of certain diseases and for the treatment of chronic and slowly developing ones. At the same time, practically healthy people can also use them to improve their quality of life. The experience of using medicinal plants in traditional medicine in the North-West Caucasus (in particular, in the Republic of Adygea) contributed to their active study with the aim of introducing official scientific medicine into clinical practice.For the treatment, prevention and diagnosis of many diseases, the medications are widely used that have a sedative effect in various neurotic conditions and have a regulatory effect on the central nervous system, reducing excitatory processes, enhancing inhibitory processes or eliminating the consequences of stressful situations. In this regard, there is a need to expand the local raw material base of medicinal plants, which accumulate biologically active substances in high concentrations.The article provides data on the study of wild North Caucasian populations of medicinal plants (valerian officinalis, common hop, motherwort and peppermint), which are promising producers of biologically active compounds. The results obtained indicate the safety of the raw material, allow us to evaluate its quality and prove the promise of ongoing scientific research, which has not only theoretical but also practical significance for the purpose of creating drugs that have a sedative effect, as well as for processing without restrictions.

In a bushfire burning of plant material generates volatile phenolics that may be absorbed by berries and leaves of grapes in nearby vineyards. In grapes these phenolics form glycoconjugates and the undesirable sensory attributes of smoke-exposed grapes only develop post-fermentation in the wine making process, when the free phenolics are released. To reduce the financial losses from producing smoke-tainted wines, phenolic glycosides associated with smoke-taint in grapes are currently monitored in analytical laboratories. Here, we performed LC-MS analysis on extracts of diverse grape varieties of various geographic sites and with varying levels of smoke taint exposure. Discovery of smoke-taint biomarkers, based on untargeted analysis led to the identification of additional phenolic compounds that could contribute significantly to the smoke-tainted flavour of wine. A total of 73 differentially expressed metabolites were detected and LCMSMS analysis resulted in the structural assignment of 15 compounds, including guaiacol and syringol derivatives and novel glycoconguate intermediaries.

Phytochemical analyses of Swertia davidii Franch. extracts using column chromatography and semi-preparative HPLC were performed. Two novel phenolic glycosides named swertiosides A and B (compounds 1 and 2, respectively) were isolated and characterized. Four known phenolic glycosides were also extracted (compounds 3-6). The structural characteristics of these novel compounds were analyzed using 1D, 2D NMR, and HRMS. All six compounds have never been isolated from this particular plant species before this study. Subsequent assessment of bioactive properties suggested that compounds 1 and 2 exhibited moderate levels of cytotoxicity. [ABSTRACT FROM AUTHOR]

Primula veris (cowslip) is an important medicinal–aromatic plant used traditionally for its expectorant and anti-inflammatory properties, as well as a valuable horticultural plant with ornamental value and agroalimentary interest (edible flowers and leaves). With extensive illegal harvesting across northern Greece to date, the long-term survival of Greek cowslip wild-growing populations seems compromised. With the aim to characterize the phytochemical content of locally adapted native genotypes of P. veris subsp. veris, we examined samples from 13 wild-growing populations sourced from 8 mountain areas along a longitudinal gradient of northern Greece. Flowers, leaves, and roots were separately evaluated with HPLC-PDA-MS for their chemical content to select the genotypes associated with the best phytochemical traits. The flowers were found to contain mainly flavonoids, isorhamnetin, quercetin, and kaempferol triglycosides, with varied population contents, generally higher in northwestern population samples with a colder and more humid climate; however, all in line with the European Medicines Agency's (EMA) reports. The leaves were characterized by the prevalence of kaempferol and quercetin triglycosides, being generally higher than that of the flowers. In the roots, saponins were detected in relatively low percentages, and the phenolic glycosides were found up to nearly 2%. The results of this study suggest a potential specificity of the marginal Greek genotypes being at the edge of the species' native distribution range in Europe and Asia. The phytochemical characterization herein supports the domestication process of Greek native cowslip genotypes. In turn, this may alleviate the overharvesting pressure in wild populations, thus contributing to species conservation and offering an incentive for farmers to sustainably cultivate at local scales well-adapted indigenous genotypes of high value. [ABSTRACT FROM AUTHOR]

Plant-derived phytochemicals have recently drawn interest in the prevention and treatment of diabetes mellitus (DM). The seeds of Moringa oleifera Lam. are widely used in food and herbal medicine for their health-promoting properties against various diseases, including DM, but many of their effective constituents are still unknown. In this study, 6 new phenolic glycosides, moringaside B–G (1–6), together with 10 known phenolic glycosides (7–16) were isolated from M. oleifera seeds. The structures were elucidated by 1D and 2D NMR spectroscopy and high-resolution electrospray ionization mass spectrometry (HR-ESI-MS) data analysis. The absolute configurations of compounds 2 and 3 were determined by electronic circular dichroism (ECD) calculations. Compounds 2 and 3 especially are combined with a 1,3-dioxocyclopentane moiety at the rhamnose group, which are rarely reported in phenolic glycoside backbones. A biosynthetic pathway of 2 and 3 was assumed. Moreover, all the isolated compounds were evaluated for their inhibitory activities against α-glucosidase. Compounds 4 and 16 exhibited marked activities with IC50 values of 382.8 ± 1.42 and 301.4 ± 6.22 μM, and the acarbose was the positive control with an IC50 value of 324.1 ± 4.99 μM. Compound 16 revealed better activity than acarbose. [ABSTRACT FROM AUTHOR]

Fifteen phenolic constituents were isolated from the 80% ethanol extract of Kalimeris shimadae, including two phenolic glycosides (1, 2), six flavonoids (3–8), five phenylpropanoids (9–13), and two lignans (14, 15). Their structures were identified by spectroscopic analysis and comparison with literature data. Compound 1 was a new glucosyringic acid derivative, whereas compounds 2–14 were first discovered from K. shimadae. [ABSTRACT FROM AUTHOR]

The recent discovery of the horizontal transfer of a toxin-neutralizing gene from plant to whitefly (Bemisia tabaci), a polyphagous insect, sparked a new area of study. In this forum, we discuss some potential biotechnological applications of this newly discovered knowledge in the coevolutionary arms race between plants and whitefly. [ABSTRACT FROM AUTHOR]

Four new phenolic glycosides lepidiumosides A–D (1–4) were isolated from the water extract of the seeds of Lepidium apetalum Willd. Their structures were determined by extensive spectroscopic (UV, IR, HR-ESI-MS, 1D and 2D NMR) analyses. In addition, these compounds were evaluated for their protective effects impaired by H2O2 in H9c2 cells, suggesting that compounds 1–4 exhibited protective effects against H2O2-induced cardiotoxicity. [ABSTRACT FROM AUTHOR]

The characteristics of high polarity and susceptibility to oxidation in phenolic glycosides increase the difficulty of their separation from natural products. In the present study, two new phenolic glycosides with similar structures were isolated from Castanopsis chinensis Hance using a combination of multistep CC and high-speed countercurrent chromatography. Preliminary separation of the target fractions was carried out by Sephadex LH-20 chromatography (100–0% EtOH in H2O). High-speed countercurrent chromatography with an optimized solvent system of N-Hexane/Ethyl acetate/Methanol/Water (1:6:3:4, v/v/v/v) with a satisfactory stationary phase retention and separation factor was used for further separation and purification of the phenolic glycosides. Consequently, two new phenolic glycoside compounds were obtained with purities of 93.0% and 95.7%. 1D-NMR and 2D-NMR spectroscopy, mass spectrometry, and optical rotation were employed to identify their structures, which were assigned as chinensin D and chinensin E. The antioxidant and α-glucosidase inhibitory activities of these two compounds were evaluated using a DPPH antioxidant assay and a α-glucosidase inhibitory assay. Both compounds showed good antioxidant activity with IC50 values of 54.5 ± 0.82 µg/mL and 52.5 ± 0.47 µg/mL. The α-glucosidase inhibitory activity of the compounds was poor. The successful isolation and structure identification of the two new compounds provides materials not only for a systematic isolation method of phenolic glycosides with similar structures, but also for the screening of antioxidants and enzyme inhibitors. [ABSTRACT FROM AUTHOR]

Five new glycosylated phenolic derivatives, rotundosides A-E (1-5), and three known glycosides (6-8) were isolated from the 95% alcohol extract of the bark of Ilex rotunda. Their structures were elucidated by extensive spectroscopic analysis and comparison with the literature data. All new compounds possessed a [5-O-(E)-caffeoyl]-β-D-apiofuranosyl-(1→6)-β-D-glucopyranosyl group. The anti-inflammatory properties of all isolated compounds were evaluated using a modified nitric oxide (NO) production in lipopolysaccharide (LPS)-induced leukemia cells in mouse macrophage (RAW264.7) method. Compound 8, dracunculifoside H, showed significant anti-inflammatory activity in vitro. [ABSTRACT FROM AUTHOR]

Acne vulgaris, typically caused by Cutibacterium acnes (C. acnes) involves chronic inflammation of the sebaceous follicles and is the most common skin disease, afflicting 85% of adolescents. We previously isolated 2 novel phenolic glycosides, 2-caffeoyl-3-hydroxy-3-methylbutyric 4′-β-D-glucopyranosyloxy-3′-hydroxybenzyl ester (citrulluside H [CH]) and 2-caffeoyl-3-hydroxy-3-methylbutyric 4′-β- d -glucopyranosyloxybenzyl ester (citrulluside T [CT]), from young fruits of watermelon (Citrullus lanatus). Both compounds suppressed UVB-induced photoaging in human fibroblasts by scavenging intracellular reactive oxygen species (ROS) and thus might be useful as natural skin care ingredients. In this study, we examined the inhibitory effects of these phenolic glycosides on C. acnes growth and C.acnes- induced inflammation. Neither phenolic glycoside inhibited the growth of C. acnes. However, they both significantly suppressed toll-like receptor (TLR) 1/2 or TLR2/6/nuclear factor κB (NF-κB) signaling in heat-killed C. acnes (hk- C. acnes) - stimulated RAW264.7 cells. Additionally, both phenolic glycosides decreased the expression of M1 macrophage biomarkers (cluster of differentiation [ CD ] 80, CD86, and inducible NO synthase [ iNOS ]), suggesting that they attenuate M1 macrophage activation. These results indicated that both CH and CT are potential therapeutic substances against C. acnes -induced skin inflammation. [ABSTRACT FROM AUTHOR]

Phytochemical studies on the fruits of Illicium verum Hook. f., also known as star anise (Magnoliaceae), resulted in the isolation of thirty-five compounds, including ten phenylpropanoids (1 – 10), eight phenolic glycosides (11 – 18), five benzoic acids (19 – 23), four flavonoids (24 – 27), four lignans (28 – 31), three organic acids (32 – 34), and one monoterpenoid (35). The structures of these metabolites were determined through NMR spectroscopy analysis and comparison with existing literature. This is the first confirmation of the presence of eight compounds (1 , 4 – 7 , 13 , 34 and 35) isolated from the family Magnoliaceae, one compound (11) from the genus Illicium , and three compounds (12 , 28 , 30) from I. verum. Furthermore, the taxonomic significance of these compounds was discussed. [Display omitted] • Thirty-five compounds were obtained from the fruits of this plant. • Eight compounds were isolated from the family Magnoliaceae for the first time. • One compound was new for the genus Illicium. • Three compounds were first confirmation from Illicium verum. [ABSTRACT FROM AUTHOR]

Primula veris (cowslip) is an important medicinal–aromatic plant used traditionally for its expectorant and anti-inflammatory properties, as well as a valuable horticultural plant with ornamental value and agroalimentary interest (edible flowers and leaves). With extensive illegal harvesting across northern Greece to date, the long-term survival of Greek cowslip wild-growing populations seems compromised. With the aim to characterize the phytochemical content of locally adapted native genotypes of P. veris subsp. veris, we examined samples from 13 wild-growing populations sourced from 8 mountain areas along a longitudinal gradient of northern Greece. Flowers, leaves, and roots were separately evaluated with HPLC-PDA-MS for their chemical content to select the genotypes associated with the best phytochemical traits. The flowers were found to contain mainly flavonoids, isorhamnetin, quercetin, and kaempferol triglycosides, with varied population contents, generally higher in northwestern population samples with a colder and more humid climate; however, all in line with the European Medicines Agency’s (EMA) reports. The leaves were characterized by the prevalence of kaempferol and quercetin triglycosides, being generally higher than that of the flowers. In the roots, saponins were detected in relatively low percentages, and the phenolic glycosides were found up to nearly 2%. The results of this study suggest a potential specificity of the marginal Greek genotypes being at the edge of the species’ native distribution range in Europe and Asia. The phytochemical characterization herein supports the domestication process of Greek native cowslip genotypes. In turn, this may alleviate the overharvesting pressure in wild populations, thus contributing to species conservation and offering an incentive for farmers to sustainably cultivate at local scales well-adapted indigenous genotypes of high value.

Plant-derived phytochemicals have recently drawn interest in the prevention and treatment of diabetes mellitus (DM). The seeds of Moringa oleifera Lam. are widely used in food and herbal medicine for their health-promoting properties against various diseases, including DM, but many of their effective constituents are still unknown. In this study, 6 new phenolic glycosides, moringaside B–G (1–6), together with 10 known phenolic glycosides (7–16) were isolated from M. oleifera seeds. The structures were elucidated by 1D and 2D NMR spectroscopy and high-resolution electrospray ionization mass spectrometry (HR-ESI-MS) data analysis. The absolute configurations of compounds 2 and 3 were determined by electronic circular dichroism (ECD) calculations. Compounds 2 and 3 especially are combined with a 1,3-dioxocyclopentane moiety at the rhamnose group, which are rarely reported in phenolic glycoside backbones. A biosynthetic pathway of 2 and 3 was assumed. Moreover, all the isolated compounds were evaluated for their inhibitory activities against α-glucosidase. Compounds 4 and 16 exhibited marked activities with IC50 values of 382.8 ± 1.42 and 301.4 ± 6.22 μM, and the acarbose was the positive control with an IC50 value of 324.1 ± 4.99 μM. Compound 16 revealed better activity than acarbose.

Nine compounds, five phenolic glycosides (1, 2, 4–6), three phenylpropanoids (7–9), and a furanone glycoside (3), were isolated from aqueous soluble extract of the dried roots of Anemone chinensis Bunge. The structures of new compounds (1–4) were elucidated by comprehensive spectroscopic data analysis as well as chemical evidence. Pulsatillanin A (1) demonstrated significant antioxidant effects through scavenging free radical in DPPH assay, and relieved the oxidative stress in LPS-induced RAW 264.7 cells by reducing ROS production, enhancing antioxidant enzyme SOD activity, replenishing depleted GSH in a dose-dependent manner. Western blot analysis revealed that 1 showed antioxidant activity via activating Nrf2 signaling pathway. [ABSTRACT FROM AUTHOR]

Six new phenolic glycosides (1-6) and thirteen known compounds (7-19) were isolated from the roots of Scrophularia ningpoensis. Their structures were determined through comprehensive analyses of the physicochemical properties and spectroscopic data (1D NMR, 2D NMR, and HR-ESI-MS). The anti-inflammatory potential of all compounds was evaluated by determining their ability to inhibit lipopolysaccharide (LPS) induced NO production in RAW 264.7 macrophage cells. In addition, the cytotoxicity of all compounds on HepG2, 4T1 and A549 cell lines was also evaluated., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier B.V. All rights reserved.)

Phenolic glycosides are the important bioactive molecules, and their bioavailability can be influenced by enzyme hydrolysis, such as β-glucosidases (EC3.2.1.21) and other glycosyl hydrolases (GHs). Wood rotting fungi possess a superfamily of GHs, but little attention has been paid to the GHs and their potential applications in biotransformation of phenolic glycosides. In this study, two GH3 gene family members of Trametes trogii S0301, mainly expressed in the carbon sources conversion stage were cloned, and TtBgl3 coded by T_trogii _12914 showed β-glucosidase activity toward 4-nitrophenyl β-D-glucopyranoside (p NPG). The recombinant TtBgl3 preferred an intermediately neutral optimum pH with >80% of the maximum activity at pH 5.0–7.0 and was stable at a wide range of pH (5.0–10.0). Phenolic glycosides transformation experiments showed that TtBgl3 was a dual-activity enzyme with both activities of aryl-β-D-glucosidase and β-glucuronidase, and could hydrolyze the β-glucoside/glucuronide bond of phenolic glycosides. Under optimized conditions, the recombinant TtBgl3 had much higher transformation efficiency toward the β-glucoside bond of gastrodin, esculin and daidzin than β-glucuronide bond of baicalin, with the transformation rate of 100 and 50%, respectively. Our homology modeling, molecular docking, and mutational analysis demonstrated that His85 and Lys467 in the acceptor-binding pocket of TtBgl3 were the potential active sites. The point mutation of His85 and Lys467 leads to the significantly impaired catalytic activity toward p NPG and also the weak transformation efficiency toward gastrodin. These findings provide insights for the identification of novel GH3 β-glucosidases from T. trogii and other wood-rotting fungi. Furthermore, TtBgl3 might be applied as green and efficient biological catalysts in the deglycosylation of diverse phenolics to produce bioactive glycosides for drug discovery in the future. [ABSTRACT FROM AUTHOR]

Phenolic glycosides are the important bioactive molecules, and their bioavailability can be influenced by enzyme hydrolysis, such as β-glucosidases (EC3.2.1.21) and other glycosyl hydrolases (GHs). Wood rotting fungi possess a superfamily of GHs, but little attention has been paid to the GHs and their potential applications in biotransformation of phenolic glycosides. In this study, two GH3 gene family members of Trametes trogii S0301, mainly expressed in the carbon sources conversion stage were cloned, and TtBgl3 coded by T_trogii_12914 showed β-glucosidase activity toward 4-nitrophenyl β-D-glucopyranoside (pNPG). The recombinant TtBgl3 preferred an intermediately neutral optimum pH with >80% of the maximum activity at pH 5.0–7.0 and was stable at a wide range of pH (5.0–10.0). Phenolic glycosides transformation experiments showed that TtBgl3 was a dual-activity enzyme with both activities of aryl-β-D-glucosidase and β-glucuronidase, and could hydrolyze the β-glucoside/glucuronide bond of phenolic glycosides. Under optimized conditions, the recombinant TtBgl3 had much higher transformation efficiency toward the β-glucoside bond of gastrodin, esculin and daidzin than β-glucuronide bond of baicalin, with the transformation rate of 100 and 50%, respectively. Our homology modeling, molecular docking, and mutational analysis demonstrated that His85 and Lys467 in the acceptor-binding pocket of TtBgl3 were the potential active sites. The point mutation of His85 and Lys467 leads to the significantly impaired catalytic activity toward pNPG and also the weak transformation efficiency toward gastrodin. These findings provide insights for the identification of novel GH3 β-glucosidases from T. trogii and other wood-rotting fungi. Furthermore, TtBgl3 might be applied as green and efficient biological catalysts in the deglycosylation of diverse phenolics to produce bioactive glycosides for drug discovery in the future.

In this study, we conducted a comprehensive investigation into a GH3 family β-glucosidase (BGL) from the wild-type strain of Oenococcus oeni and its mutated counterpart from the acid-tolerant mutant strain. Our analysis revealed the mutant BGL's remarkable capacity to adapt to wine-related stress conditions, including heightened tolerance to low pH, elevated ethanol concentrations, and metal ions. Additionally, the mutant BGL exhibited superior hydrolytic activity towards various substrates. Through de novo modeling, we identified specific amino acid mutations responsible for its resilience to low pH and high ethanol environments. In simulated wine conditions, the mutant BGL outperformed both wild-type and commercial BGLs, efficiently releasing terpene and phenolic aglycones from glycosides in wine grapes. These findings not only expand our understanding of O. oeni BGLs but also highlight their potential in enhancing wine production. The mutant BGL's enhanced adaptation to wine stress conditions opens promising avenue for improving wine quality and flavor. [Display omitted] • Mutant BGL showed superior low-pH and high-ethanol tolerance than wild-type BGL. • Mutant BGL had better hydrolysis abilities to various substrates than wild-type BGL. • Mutant BGL showed higher activity in presence of some reagents than wild-type BGL. • Enhanced pH/ethanol tolerance may be related to BGL mutation-induced stability. • Mutated BGL exhibits superior ability to release terpene aglycones under wine stress. [ABSTRACT FROM AUTHOR]

The characteristics of high polarity and susceptibility to oxidation in phenolic glycosides increase the difficulty of their separation from natural products. In the present study, two new phenolic glycosides with similar structures were isolated from Castanopsis chinensis Hance using a combination of multistep CC and high-speed countercurrent chromatography. Preliminary separation of the target fractions was carried out by Sephadex LH-20 chromatography (100–0% EtOH in H2O). High-speed countercurrent chromatography with an optimized solvent system of N-Hexane/Ethyl acetate/Methanol/Water (1:6:3:4, v/v/v/v) with a satisfactory stationary phase retention and separation factor was used for further separation and purification of the phenolic glycosides. Consequently, two new phenolic glycoside compounds were obtained with purities of 93.0% and 95.7%. 1D-NMR and 2D-NMR spectroscopy, mass spectrometry, and optical rotation were employed to identify their structures, which were assigned as chinensin D and chinensin E. The antioxidant and α-glucosidase inhibitory activities of these two compounds were evaluated using a DPPH antioxidant assay and a α-glucosidase inhibitory assay. Both compounds showed good antioxidant activity with IC50 values of 54.5 ± 0.82 µg/mL and 52.5 ± 0.47 µg/mL. The α-glucosidase inhibitory activity of the compounds was poor. The successful isolation and structure identification of the two new compounds provides materials not only for a systematic isolation method of phenolic glycosides with similar structures, but also for the screening of antioxidants and enzyme inhibitors.

Two new phenolic glycosides 7R,8R-threo-4,7,9,9'-tetrahydroxy-3-methoxy-8-O-4'-neolignan-3'-O-(3''-α-L-arabinofuranosyl)-β-D-glucopyranoside. (1), 4-(4'-hydroxyphenyl)-2-butanone-4''-O-(6-β-D-xylosyl)-β-D-glucopyranoside (2), along with two known related analogues 7R,8R-threo-4,7,9,9'-tetrahydroxy-3-methoxy-8-O-4'-neolignan-3'-O-β-D-glucopyranoside (3), 4-(4'-hydroxyphenyl)-2-butanone-4'-O-β-D-glucopyranoside (4) were obtained from the roots of Sanguisorba officinalis. Combined with acid hydrolysis derivatization, the absolute configurations of these new compounds were elucidated by comprehensive analyses of spectroscopic data including nuclear magnetic resonance (NMR), electrospray ionization high resolution mass (HRESIMS) as well as circular dichroism (CD). Compounds 1-4 exhibited anti-inflammatory properties in vitro by attenuating the production of inflammatory mediators, such as nitric oxide (NO) as well as tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6). [ABSTRACT FROM AUTHOR]

The new compounds vaccinisides A–C (1–3) were isolated from leaves of Vaccinium vitis-idaea (Ericaceae) and identified using chemical transformations; UV, IR, and NMR spectroscopy; and mass spectrometry as 2′ ,6′-di-O-caffeylarbutin (1), quercetin-3-O-[2′′-O-(3′′′-hydroxy-3′′′-methylglutaroyl)]-α-L-rhamnopyranoside (2), and quercetin-3-O-[2′′-O-(3′′′-hydroxy-3′′′-methylglutaroyl)-4′′-O-(3′′′′-hydroxy-3′′′′-methylglutaroyl)]-α-L-rhamnopyranoside (3). [ABSTRACT FROM AUTHOR]

Abstract Phytochemical studies on MeOH extract of stems of Euphorbia griffithii led to the isolation of one new hydrolyzable tannin dimer, corilagiffithiin (1) and one new galloyl-glucoside (2), alongside six known ones (3–8). Their structures and absolute configurations were determined by in depth spectroscopic analyses and comparison of their 1D NMR and MS data with literature reported values. Configurations of sugar moieties were determined by acidic hydrolysis and subsequent GC analysis of their corresponding trimethylsilylated l-cysteine adduct. At a concentration of 50 μM, compounds 1–3 showed no anti-inflammatory activities. Graphic Abstract

In a bushfire burning of plant material generates volatile phenolics that may be absorbed by berries and leaves of grapes in nearby vineyards. In grapes these phenolics form glycoconjugates and the undesirable sensory attributes of smoke-exposed grapes only develop post-fermentation in the wine making process, when the free phenolics are released. To reduce the financial losses from producing smoke-tainted wines, phenolic glycosides associated with smoke-taint in grapes are currently monitored in analytical laboratories. Here, we performed LC-MS analysis on extracts of diverse grape varieties of various geographic sites and with varying levels of smoke taint exposure. Discovery of smoke-taint biomarkers, based on untargeted analysis led to the identification of additional phenolic compounds that could contribute significantly to the smoke-tainted flavour of wine. A total of 73 differentially expressed metabolites were detected and LCMSMS analysis resulted in the structural assignment of 15 compounds, including guaiacol and syringol derivatives and novel glycoconguate intermediaries., Competing Interests: The authors declare the following financial interests/personal relationships which may be considered as potential competing interests: Priyanka Reddy reports article publishing charges was provided by Agriculture Victoria. Priyanka Reddy reports a relationship with Agriculture Victoria that includes: employment. There are no conflicts of interest. If there are other authors, they declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (© 2024 The Authors.)

Background: Prolonged exposure to UV radiation disrupts the oxidative stress defense systems; in the absence of adequate reactive oxygen species (ROS)‐scavenging mechanisms, the ROS produced cause oxidative damage to DNA, proteins, carbohydrates, and lipids. Thus, ROS elimination can protect against photoaging and possibly skin cancer. We recently isolated two novel phenolic glycosides (citrulluside H and citrulluside T) with antioxidative activity from young watermelon (Citrullus lanatus) fruits. In the present study, we evaluated the protective effect of these compounds against UV‐B–induced photodamage in normal human dermal fibroblasts (NHDFs). Methods: NHDFs were exposed to UV‐B irradiation at 25 mJ/cm2. Matrix metalloproteinase (MMP)‐1 and MMP‐3 mRNA levels were measured by quantitative real‐time PCR. MMP protein expression, as well as MAPK and NF‐κB signaling, was investigated by Western blot analysis. Activation protein‐1 (AP‐1) transcriptional activity was determined using a luciferase reporter assay. Intracellular ROS levels were measured using the CellROX™ Deep Red Reagent. Results: Citrulluside H and citrulluside T significantly downregulated the protein and mRNA expression of MMP‐1 and MMP‐3, which are associated with the onset of skin wrinkle formation. Importantly, inhibition of UV‐B–induced MMP expression in NHDFs by citrulluside H and citrulluside T was primarily due to the attenuation of MAPK/AP‐1 and NF‐κB signaling via scavenging of the generated ROS. Conclusion: Our findings delineated both citrulluside H and citrulluside T as potential agents for alleviating UV‐induced skin photoaging. [ABSTRACT FROM AUTHOR]

A phytochemical study of the stems of Homalium stenophyllum Merr. & Chun led to the isolation of two new phenolic glycosides (1 and 2) and three known compounds (3–5). The molecular structures of these isolated new phenolic glycosides (1 and 2) were unambiguously established on the basis of comprehensive spectroscopic methods. All the isolated new compounds were evaluated for their cytotoxicities against three human cancer cell lines: HeLa, A-549, and MCF-7 in vitro. [ABSTRACT FROM AUTHOR]

Seventeen phenolic glycosides were isolated from the Nitraria sibirica. Their structures were identified by the spectroscopic data and comparison with literatures as isovanillyl alcohol-7-O-β-d-glucopyranoside (1), benzyl β-primeveroside (2), benzyl-O-β-d-glucopyranoside (3), 1-O-β-d-glucopyranosyl-4-(8-hydroxyethyl)-2-methoxyphenyl (4), dehydrosyringin (5), trans-ferulic acid-4-O-β-d-glucoside (6), cis-ferulic acid 4-O-β-d-glucopyranoside (7), glucosyringic acid (8), 1-O-feruloyl-β-d-glucoside (9), sachaloside VII (10), (3S, 5R, 6R, 7E, 9S)-megastigmane-7-ene-3-hydroxy-5,6-epoxy-9-O-β-d-glucopyranoside(11), 3-hydroxy-4,5-dimethoxybenzyl alcohol (12), pinoresinol 4-O-β-d-glucopyranoside (13), eucommin A (14), isoeucommin A (15), acanthoside (16), liriodendrin (17). All these compounds except compound 13 were isolated from the Nitraria genus for the first time. In bioactivity assays for all compounds, the compounds 8 and 15 were exhibited strong antioxidant activity (IC50 = 18.11 and 16.29 μM respectively), while compounds 3 and 11 were exhibited strong PTP1B enzymatic inhibition (IC50 = 6.97 and 11.76 μM, respectively). Furthermore, the compounds 10 and 17 were presented strong inhibitory capacities against Candida albicans (14.5 and 13.5 mm, respectively). [ABSTRACT FROM AUTHOR]

Two new phenolic glycosides (1-2), along with six existing compounds (3-8), were isolated from the ethanolic extract of Ilex pubescens roots, a traditional folk medicine. These structures were determined using HR-ESI-MS, IR, UV, and NMR (including 1 D, 2 D-NMR). The anti-inflammatory activities of three phenolic glycosides (1-3) were evaluated in the human HepG2 cell lines. The results showed that compound 3 could induce P-gp and BCRP expression through the Nrf2-mediated pathway. [ABSTRACT FROM AUTHOR]

The phytochemical investigation of the stems of Homalium stenophyllum afforded seven new phenolic glycosides (1−5 and 8−9) and two known compounds (6 and 7). Their structures were elucidated by comprehensive analyses of NMR spectroscopic, mass spectrometric data and chemical hydrolysis. Additionally, their anti-inflammatory activities against the NO production in LPS-induced macrophages were evaluated. [ABSTRACT FROM AUTHOR]

Phenolic compounds in pig diets, originating either from feed ingredients or additives, may occur as glycosides, that is conjugated to sugar moieties. Upon ingestion, their bioavailability and functionality depend on hydrolysis of the glycosidic bond by endogenous or microbial glycosidases. Hence, it is essential to map the glycosidase activities towards phenolic glycosides present along gut. Therefore, the activity of three key glycosidases, that is α‐glucosidase (αGLU), β‐glucosidase (βGLU) and β‐galactosidase (βGAL), was quantified in small intestinal mucosa and digesta of piglets at different gastrointestinal sites (stomach, three parts of small intestine, caecum and colon) and at different ages around weaning (10 days before and 0, 2, 5, 14 and 28 days after weaning). Activity assays were performed with p‐nitrophenyl glycosides at neutral pH. The αGLU activities in mucosa and digesta were low (overall means 1.4 and 60 U respectively) as compared to βGLU (15.2 and 199 U) and βGAL (23.4 and 298 U; p <.001). Moreover, αGLU activity in mucosa was unaffected by age. Conversely, βGLU and βGAL activities dropped significantly after weaning. Minimal levels, ranging between 18% and 54% of the pre‐weaning values, were reached at 5 days post‐weaning. Similarly, in small intestinal digesta, reductions from 60% up to 90% were observed for the three enzyme activities on day five post‐weaning as compared to pre‐weaning levels. In caecal contents, activities were lowest at 14 days post‐weaning, while in stomach and colon no clear weaning‐induced effects were observed. Our data suggest that weaning affects the glycosidase activity in mucosa (mainly endogenous origin) and digesta (primarily bacterial origin) with the most pronounced effects occurring 5 days post‐weaning. Moreover, differences in activities exist between different glycosidases and between gut locations. These insights can facilitate the prediction of the fate of existing and newly synthetized glycosides after oral ingestion in piglets. [ABSTRACT FROM AUTHOR]

SUMMARY: The salicinoids are anti‐herbivore phenolic glycosides unique to the Salicaceae (Populus and Salix). They consist of a salicyl alcohol glucoside core, which is usually further acylated with benzoic, cinnamic or phenolic acids. While salicinoid structures are well known, their biosynthesis remains enigmatic. Recently, two enzymes from poplar, salicyl alcohol benzoyl transferase and benzyl alcohol benzoyl transferase, were shown to catalyze the production of salicyl benzoate, a predicted potential intermediate in salicinoid biosynthesis. Here, we used transcriptomics and co‐expression analysis with these two genes to identify two UDP‐glucose‐dependent glycosyltransferases (UGT71L1 and UGT78M1) as candidate enzymes in this pathway. Both recombinant enzymes accepted only salicyl benzoate, salicylaldehyde and 2‐hydroxycinnamic acid as glucose acceptors. Knocking out the UGT71L1 gene by CRISPR/Cas9 in poplar hairy root cultures led to the complete loss of salicortin, tremulacin and tremuloidin, and a partial reduction of salicin content. This demonstrated that UGT71L1 is required for synthesis of the major salicinoids, and suggested that an additional route can lead to salicin. CRISPR/Cas9 knockouts for UGT78M1 were not successful, and its in vivo role thus remains to be determined. Although it has a similar substrate preference and predicted structure as UGT71L1, it appears not to contribute to the synthesis of salicortin, tremulacin and tremuloidin, at least in roots. The demonstration of UGT71L1 as an enzyme of salicinoid biosynthesis will open up new avenues for the elucidation of this pathway. Significance Statement: The salicinoids are bioactive and ecologically significant phenolics glycosides found in poplars and willows. Here, we identify two salicyl benzoate UDP‐glycosyltransferases and use CRISPR/Cas9 knockouts in transgenic poplar hairy roots to demonstrate that one of these enzymes is essential for salicinoid biosynthesis. [ABSTRACT FROM AUTHOR]

Transformed hairy root cultures have become an alternative for the biosynthesis of plant secondary metabolites with biological activities. In this present work, the effects of liquid Murashige and Skoog (MS) and Gamborg B5 (B5) medium on kinetic behavior, biomass and phenolic metabolite production were analyzed in Turbinicarpus lophophoroides (Werderm.) Buxb. & Backeb. hairy root cultures. Liquid MS medium showed the highest biomass production (13.67 g L−1 dry weight) after 77 d of culture. For B5 medium, highest biomass was achieved sooner, at day 56, but with lower total biomass (8.10 g L−1 dry weight). After isolation, structural elucidation of the major compound present in T. lophophoroides hairy roots was determined by nuclear magnetic resonance and mass spectral analysis. As a result, a ferulic acid derivative (feruloyl-glucoside) was isolated from T. lophophoroides hairy roots and reported for the first time. Quantitative analysis indicated that feruloyl-glucoside was the major phenolic metabolite at 56 d of growth in MS medium (2.7267 ± 0.041 mg g−1 dry weight L−1) and at 7 and 35 d in B5 medium (2.6328 ± 0.108 and 2.4372 ± 0.026 mg g−1 dry weight L−1, respectively). The feruloyl-glucoside was not detected in untransformed roots (control). The present results suggested the potential of T. lophophoroides hairy roots culture for the production of this phenolic glycoside. [ABSTRACT FROM AUTHOR]

Two new phenolic glycosides, named lanatusosides C (1) and D (2), together with four known compounds (3-6), were isolated from the seeds of Citrullus lanatus. Among them, compounds 3 and 4 were isolated from Cucurbitaceae for the first time, and compound 5 was reported from this plant for the first time. Their structures were elucidated by means of extensive spectral analysis, including HR-ESI-MS, 1H and 13C NMR techniques. The isolated new compounds were evaluated for cytotoxic activity against HepG2 cell line, of which compound 1 demonstrated weak cytotoxicity against the tested cell line. [ABSTRACT FROM AUTHOR]

Phytochemical studies on MeOH extract of stems of Euphorbia griffithii led to the isolation of one new hydrolyzable tannin dimer, corilagiffithiin (1) and one new galloyl-glucoside (2), alongside six known ones (3–8). Their structures and absolute configurations were determined by in depth spectroscopic analyses and comparison of their 1D NMR and MS data with literature reported values. Configurations of sugar moieties were determined by acidic hydrolysis and subsequent GC analysis of their corresponding trimethylsilylated l-cysteine adduct. At a concentration of 50 μM, compounds 1–3 showed no anti-inflammatory activities. [ABSTRACT FROM AUTHOR]

Adult and juvenile herbivores of the same species can use divergent feeding strategies, and thus may inhabit and consume different parts of the plant. Because the expression of chemical defences often differs between host plant tissues, this variation may result in disparate performance outcomes for adult and juvenile conspecifics that feed on distinct dietary substrates.The goal of this study was to evaluate how host range may differ between adults and juveniles in a generalist herbivore. We addressed the impacts of among‐ and within‐plant defence variation using the wood‐feeding Asian longhorned beetle (Anoplophora glabripennis) and three host plants having a range of putative resistance.Impacts of host plants on adult and offspring performance were assessed using a series of controlled bioassays. We evaluated adult‐feeding and egg‐laying behaviours in choice and no‐choice experiments using the different hosts, and subsequent offspring establishment. We then evaluated host plant chemical composition related to nutrition and defence.Different plants had strong impacts on adult performance, but these patterns did not extend to effects on offspring. Females were capable of developing eggs when provided Acer rubrum, but not Populus deltoides or Populus tomentosa. Females that produced eggs by feeding on A. rubrum, however, deposited eggs into all three plant species. Larvae hatched and consumed tissues in all three hosts. The differences between adult and juvenile utilization of Populus spp. were reflected in markedly higher salicinoid phenolic concentrations in bark (>2% dw), while wood had trace quantities.Our results demonstrate that plant resistance mechanisms can differentially act upon adult and juvenile life stages of a polyphagous herbivore when there is differential expression of chemical defences among plant tissue types. Anoplophora glabripennis has been a globally successful invader due in part to its broad host range, and our results suggest a mechanism that permits the beetle to exploit marginally resistant plants. This study has implications for how host range differs between insect feeding stages, which is particularly important for invasive, polyphagous species encountering novel food sources. [ABSTRACT FROM AUTHOR]

Six undescribed compounds, including three phenolic glycosides (1 – 3) and three indole alkaloids (4 – 6), together with ten known alkaloids (7 – 16) and three known phenolic glycosides (17 – 19), were isolated from 70% EtOH aqueous extracts of the roots and rhizomes of Clematis chinensis Osbeck. The structures were elucidated by NMR, HRESIMS and X-ray diffraction spectroscopies. The anti-inflammatory activity of these compounds was evaluated, and twelve compounds showed significant inhibitory activity against TNF-α with an inhibition ratio from 47.87% to 94.70% at a dose of 10 μM. Compound 7 exhibited significant inhibitory activity against TNF-α and IL-6 with IC 50 values of 3.99 μM and 2.24 μM, respectively. Compound 8 displayed potent anti-inflammatory activity against mouse ear edema induced by croton oil. A mechanistic study suggested that compounds 7 and 8 decreased the activation of the NF-κB signaling pathway to reduce the secretion of inflammatory factors in LPS-induced RAW 264.7 cells. Six undescribed compounds together with thirteen known ones were isolated from Clematis chinensis. Mechanistic study suggested that compounds 7 and 8 could decrease the activation of NF-κB signaling pathway. [Display omitted] • Six undescribed compounds were isolated from the Clematis chinensis. • Twelve compounds showed inhibitory activity against TNF-α. • Three compounds exhibited potent inhibitory activity on NO. • Compounds 7 and 8 could decrease the activation of NF-κB signaling pathway. [ABSTRACT FROM AUTHOR]

Objective: To find the genuine structure with anti-acetylcholinesterase (anti-AChE) from the phenolic glycosides abundant in Leonurus japonicus (Lamiaceae). The assay for anti-AChE activity is often used to lead anti-Alzheimer's drugs. Methods: The five phenolic glycosides, tiliroside, leonurusoside C, 2‴-syringoylrutin, rutin, and lavanduliofolioside were isolated from L. japonicus. The activities of the glycosides were relatively low. Seven compounds including p-coumaric acid, caffeic acid, hydroxytyrosol, salidroside, syringic acid, kaempferol, and quercetin, which are produced by the hydrolysis of the five glycosides, were also assayed for anti-AChE activity. Results: Of those seven compounds, the five compounds other than salidroside and syringic acid exhibited potent anti-AChE activities. In particular, the IC50s of caffeic acid and quercetin were (1.05 ± 0.19) and (3.58 ± 0.02) μg/mL, respectively. Rutin was the most abundant flavonoid in the extract (9.18 mg/g as measured by HPLC). Conclusion: The substances with potent anti-AChE were caffeic acid, quercetin, p-coumaric acid, kaempferol, and hydroxytyrosol that can be produced from their glycosides.

A new phenolic glycoside named salicyltomenside (1), with five similar compounds, salicyltremuloidin (2), tremuloidin (3), isograndidentatin A (4), siebolside B (5), and salicin (6) were isolated from Populus tomentosa Carr. Additionally, salicyltremuloidin (2) was obtained from the plant for the first time. Structure of the new compound was determined using spectroscopic methods including ESI-MS and 1D- and 2D-NMR. Others were elucidated through ¹H and 13C NMR spectra and comparison with literature data. Notably, salicyltomenside (1) and salicyltremuloidin (2) were structural isomers. [ABSTRACT FROM AUTHOR]

Phytochemical investigation of Cissus quadrangularis stems led to the isolation of one new phenolic glycoside (1) and two new lignan glycosides (7 & 8) along with twelve known compounds (2-6 & 9-15). Their chemical structures were determined on the basis of extensive spectroscopic analysis using 1D, 2D NMR, and mass spectrometric analysis. Among the known compounds, 4-6, 9 and 12 were isolated for the first time from the genus Cissus whereas compounds 10, 11 and 13 for the first time from this plant. [ABSTRACT FROM AUTHOR]

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Induction of plant chemical defenses in response to insect feeding may be localized to the site of damage or expressed systemically, mediated by signal transduction throughout the plant. Such systemic induction processes have been widely investigated in plants with single stems, but rarely in clonal plants comprised of multiple ramets with vascular connections. For a clonal tree species such as trembling aspen (Populus tremuloides Michx), integration of induced defense within clones could be adaptive, as clones are spatially extensive and susceptible to outbreak herbivores. We used pairs of aspen saplings with shared roots, replicated from three genotypes, to determine whether defense-induction signals are communicated within clones. One ramet in each pair was subjected to a damage treatment (feeding by Lymantria dispar, followed by mechanical damage), and subsequent changes in leaf defensive chemistry were measured in both ramets. Responses to damage varied by defense type: condensed tannins (CTs) increased in damaged ramets but not in connected undamaged ramets, whereas salicinoid phenolic glycosides (SPGs) were not induced in any ramets. Genotypes varied in their levels of CTs, but not in their levels of SPGs, and responded similarly to damage treatment. These results suggest that, even with both vascular and volatile information available, young aspen ramets do not induce defenses based on signals or metabolites from other ramets. Thus, unlike other clonal plant species, aspen do not appear to coordinate defense induction within clones. Lack of coordinated early induction in aspen may be related to the function of CTs in tolerance, rather than resistance. [ABSTRACT FROM AUTHOR]

Four new phenolic glycosides (1-4), together with 12 known ones (5-16), were isolated from the essential oil extraction waste of Lavandula angustifolia. Their structures were unequivocally determined by extensive spectroscopic analysis (1D and 2D NMR, HR-ESI-MS, UV, and optical rotation), chemical method, and comparison with data reported in the literature. The antioxidant activities of all compounds and new compounds' influence on melanin content in B16 melanoma cells were examined, which indicated that compounds 1, 8, 13 had a certain degree of DPPH free radical scavenging activities, while only compound 2 could increase the melanin content with a dose-dependent manner. [ABSTRACT FROM AUTHOR]

The review systematizes data about chemical composition of bark, leaves, inflorescences, and sprouts of different species of Salix L. The closest attention is payed to investigations of Salix, which has been recently carried out in our country and abroad. For every group of biologically active substances described in Salix there are data about suppressed types of pharmacological activity.

The roots of Polygala tenuifolia Wild (Polygalaceae), which is among the most important components of traditional Chinese herbal medicine, have been widely used for over 1000 years to treat a variety of diseases. In the current investigation of secondary metabolites with anti-inflammatory properties from Korean medicinal plants, a phytochemical constituent study led to the isolation of 15 compounds (1–15) from the roots of P. tenuifolia via a combination of chromatographic methods. Their structures were determined by means of spectroscopic data such as nuclear magnetic resonance (NMR), 1D- and 2D-NMR, and liquid chromatography-mass spectrometry (LC-MS). As the obtained results, the isolated compounds were divided into two groups—phenolic glycosides (1–9) and triterpenoid saponins (10–15). The anti-inflammatory effects of crude extracts, fractions, and isolated compounds were investigated on the production of the pro-inflammatory cytokines interleukin (IL)-12 p40, IL-6, and tumour necrosis factor-α in lipopolysaccharide-stimulated bone marrow-derived dendritic cells. The IC50 values, ranging from 0.08 ± 0.01 to 21.05 ± 0.40 μM, indicated potent inhibitory effects of the isolated compounds on the production of all three pro-inflammatory cytokines. In particular, compounds 3–12, 14, and 15 showed promising anti-inflammatory activity. These results suggest that phenolic and triterpenoid saponins from P. tenuifolia may be excellent anti-inflammatory agents.

The root of Rhodiola imbricata, a Trans Himalayan food crop is known for its antioxidant and adaptogenic properties. Four new compounds (7, 11, 12 and 15) together with known phenolic glycosides (10, 13–14, 16–19) and other phenolics (1–6, 8–9) were isolated from the ethyl acetate extract of the roots of R. imbricata. The structures of isolated molecules were established by spectroscopic techniques (ESI-HRMS, 1D and 2D NMR) and chemical methods. The compounds were evaluated for their antioxidant (radical scavenging, MTT antioxidant, linoleic acid peroxidation and reducing power assay) and anticancer activities against A-549 and MCF-7 cancer cell lines.