Статті в журналах: "Stilbenoidi"

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Kambiranda, Devaiah, Sheikh Basha, Stephen Stringer, James Obuya, and Janana Snowden. "Multi-year Quantitative Evaluation of Stilbenoids Levels Among Selected Muscadine Grape Cultivars." Molecules 24, no. 5 (March 11, 2019): 981. http://dx.doi.org/10.3390/molecules24050981.

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Stilbenoids such as t-piceid, t-resveratrol, ε-viniferins, and t-pterostilbene can differ significantly among grape cultivars and years due to variation in environmental conditions and subsequent stressors encountered during a year. This study evaluated diverse muscadine grape cultivars for their ability to consistently produce four major stilbenoids such as t-piceid, t-resveratrol, ε-viniferins, and t-pterostilbene irrespective of environmental changes that can impact their production. Berries from forty-two muscadine grape cultivars were collected for three years (2013, 2014, and 2015) to measure stilbenoids. Results showed significant differences in the composition of four stilbenoids among the muscadine cultivars. The highest level of stilbenoids was observed in ‘Fry Seedless’ (270.20 µg/g fresh weight) in each of the three consecutive years tested followed by ‘Pride’ (46.18 µg/g fresh weight) while ‘Doreen’ produced the lowest level of stilbenoids (1.73 µg/g fresh weight). Results demonstrated that certain muscadine grape cultivars consistently produced varied levels of the four major stilbenoids year after year. Based on the total content of stilbenoids, the 42 muscadine cultivars studied were grouped into three categories such as High, Medium and Low stilbenoid-containing cultivars. This information will help establish new vineyards with cultivars that are less prone to variations in environmental conditions and can consistently produce stilbenoid-rich muscadine grape berries with enhanced market value to promote consumer health.

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Pawlus, Alison D., Pierre Waffo-Téguo, Jonah Shaver, and Jean-Michel Mérillon. "Stilbenoid chemistry from wine and the genus Vitis, a review." OENO One 46, no. 2 (June 30, 2012): 57. http://dx.doi.org/10.20870/oeno-one.2012.46.2.1512.

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Stilbenoids are of great interest on account of their many promising biological activities, especially in regards to prevention and potential treatment of many chronic diseases associated with aging. The simple stilbenoid monomer, E-resveratrol, has received the most attention due to early in vitro and in vivo biological activities in anti-aging assays. Since Vitis vinifera, primarily in the form of wine, is a major dietary source of these compounds, there is a tremendous amount of research on resveratrol in wine and grapes. Relatively few biological studies have been performed on other stilbenoids from Vitis, primarily due to the lack of commercial sources of many of these compounds. The diverse stilbenoids from this economically important genus are an untapped source of health promoting compounds and because of this, numerous efforts for isolation, identification and quantification of additional stilbenoids have been ongoing. Additionally, due to their role as phytoalexins, stilbenoids play an important role in the defense against pathogens. Therefore, the compounds produced by highly resistant strains are of great interest for the development of resistant crops, natural spray reagents, and as new dietary supplements or pharmaceuticals. Since closely related species are likely to have similar metabolic pathways, a more thorough understanding of the chemical diversity of stilbenoids within Vitis is useful in this endeavor. In this review, we focus on stilbenoids found in the Vitis genus with the aim of aiding future stilbenoid chemistry, particularly in V. vinifera and wine. Additionally, we discuss the efforts to quantify stilbenoids in Vitis, with a focus on non-resveratrol stilbenoid compounds.

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Gajurel, Gaurav, Rokib Hasan, and Fabricio Medina-Bolivar. "Antioxidant Assessment of Prenylated Stilbenoid-Rich Extracts from Elicited Hairy Root Cultures of Three Cultivars of Peanut (Arachis hypogaea)." Molecules 26, no. 22 (November 10, 2021): 6778. http://dx.doi.org/10.3390/molecules26226778.

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Peanut produces prenylated stilbenoids upon biotic stress. However, the role of these compounds against oxidative stress have not been thoroughly elucidated. To this end, the antioxidant capacity of extracts enriched in prenylated stilbenoids and derivatives was studied. To produce these extracts, hairy root cultures of peanut cultivars Hull, Tifrunner, and Georgia Green were co-treated with methyl jasmonate, cyclodextrin, hydrogen peroxide, and magnesium chloride and then the stilbenoids were extracted from the culture medium. Among the three cultivars, higher levels of the stilbenoid derivatives arachidin-1 and arachidin-6 were detected in cultivar Tifrunner. Upon reaction with 2,2-diphenyl-1picrylhydrazyl, extracts from cultivar Tifrunner showed the highest antioxidant capacity with an IC50 of 6.004 µg/mL. Furthermore, these extracts had significantly higher antioxidant capacity at 6.25 µg/mL and 3.125 µg/mL when compared to extracts from cultivars Hull and Georgia Green. The stilbenoid-rich extracts from peanut hairy roots show high antioxidant capacity and merit further study as potential nutraceuticals to promote human health.

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Chai, Yuan-yuan, Fang Wang, Yan-li Li, Ke Liu, and Hui Xu. "Antioxidant Activities of Stilbenoids fromRheum emodiWall." Evidence-Based Complementary and Alternative Medicine 2012 (2012): 1–7. http://dx.doi.org/10.1155/2012/603678.

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Rheum emodiWall has been reported to possess protective effect in many inflammatory diseases and oxidative stress-related injuries. This study aims to investigate antioxidant power of stilbenoids fromR. emodiand then explore the material basis for its antioxidant potential. The most abundant stilbenoid piceatannol-4′-O-β-D-glucopyranoside (PICG) and its aglycon piceatannol (PICE) were isolated fromR. emodirhizome. Using well-accepted antioxidant chemicals as reference, antioxidant activity of these stilbenoids was examined by measuring DPPH and superoxide anion radical scavenging, ferric reducing power, and inhibition of lipid peroxidationin vitro. Both PICG and PICE displayed promising antioxidant activity in all the four assays. Comparisons among the tested compounds indicated that PICE has the most potent antioxidant activity and the presence of 3′-hydroxyl group may enhance antioxidant activity of stilbenoids. The antioxidative effect of PICE at the cellular level was further demonstrated on the model of hydrogen-peroxide-induced H9c2 rat cardiomyoblasts injury. Taking into account the rapidin vivometabolic transformation of PICG into PICE it can be inferred that the most abundant stilbenoid PICG may be an important constituent responsible for the antioxidant potential ofR. emodiand promising to be developed as an antioxidant agent for supplementary or therapeutic use.

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5

Rathore, Rajendra, and Jay K. Kochi. "Vicinal-diaryl interactions in stilbenoid hydrocarbons as observed in the through-space charge delocalization of their cation radicals." Canadian Journal of Chemistry 77, no. 5-6 (June 1, 1999): 913–21. http://dx.doi.org/10.1139/v99-081.

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The conformational preference of vicinal or 1,2-phenyl groups is probed in two classes of ring-substituted 1,2-diphenylbicyclooctene (stilbenoid) hydrocarbons 1a-1d and 2a-2c. UV-vis spectroscopy reveals, and X-ray crystallography verifies, the intramolecular (edge-to-face) orientation for the phenyl-phenyl interaction in stilbenoids 1a-1d. Most importantly, when two pairs of ortho-methyl substituents are present, the cofacial phenyl groups in the stilbenoid donors are established by X-ray crystallography and spectrally observed in the cation radicals (2a+.-2c+.) by the appearance of new bands with strong absorptions in the near IR with λmax = 1100-1315 nm, analogous to those previously observed in intermolecular (aromatic) interactions of aromatic cation radicals.Key words: stilbenoid hydrocarbon, cation radical, aryl-aryl interaction.

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6

Billet, Kévin, Magdalena Anna Malinowska, Thibaut Munsch, Marianne Unlubayir, Sophie Adler, Guillaume Delanoue, and Arnaud Lanoue. "Semi-Targeted Metabolomics to Validate Biomarkers of Grape Downy Mildew Infection Under Field Conditions." Plants 9, no. 8 (August 10, 2020): 1008. http://dx.doi.org/10.3390/plants9081008.

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Grape downy mildew is a devastating disease worldwide and new molecular phenotyping tools are required to detect metabolic changes associated to plant disease symptoms. In this purpose, we used UPLC-DAD-MS-based semi-targeted metabolomics to screen downy mildew symptomatic leaves that expressed oil spots (6 dpi, days post-infection) and necrotic lesions (15 dpi) under natural infections in the field. Leaf extract analyses enabled the identification of 47 metabolites belonging to the primary metabolism including 6 amino acids and 1 organic acid, as well as an important diversity of specialized metabolites including 9 flavonols, 11 flavan-3-ols, 3 phenolic acids, and stilbenoids with various degree of polymerization (DP) including 4 stilbenoids DP1, 8 stilbenoids DP2, and 4 stilbenoids DP3. Principal component analysis (PCA) was applied as unsupervised multivariate statistical analysis method to reveal metabolic variables that were affected by the infection status. Univariate and multivariate statistics revealed 33 and 27 metabolites as relevant infection biomarkers at 6 and 15 dpi, respectively. Correlation-based networks highlighted a general decrease of flavonoid-related metabolites, whereas stilbenoid DP1 and DP2 concentrations increased upon downy mildew infection. Stilbenoids DP3 were identified only in necrotic lesions representing late biomarkers of downy mildew infection.

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7

Ball, Judith M., Fabricio Medina-Bolivar, Katelyn Defrates, Emily Hambleton, Megan E. Hurlburt, Lingling Fang, Tianhong Yang, et al. "Investigation of Stilbenoids as Potential Therapeutic Agents for Rotavirus Gastroenteritis." Advances in Virology 2015 (2015): 1–10. http://dx.doi.org/10.1155/2015/293524.

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Rotavirus (RV) infections cause severe diarrhea in infants and young children worldwide. Vaccines are available but cost prohibitive for many countries and only reduce severe symptoms. Vaccinated infants continue to shed infectious particles, and studies show decreased efficacy of the RV vaccines in tropical and subtropical countries where they are needed most. Continuing surveillance for new RV strains, assessment of vaccine efficacy, and development of cost effective antiviral drugs remain an important aspect of RV studies. This study was to determine the efficacy of antioxidant and anti-inflammatory stilbenoids to inhibit RV replication. Peanut (A. hypogaea) hairy root cultures were induced to produce stilbenoids, which were purified by high performance countercurrent chromatography (HPCCC) and analyzed by HPLC. HT29.f8 cells were infected with RV in the presence stilbenoids. Cell viability counts showed no cytotoxic effects on HT29.f8 cells. Viral infectivity titers were calculated and comparatively assessed to determine the effects of stilbenoid treatments. Two stilbenoids, trans-arachidin-1 and trans-arachidin-3, show a significant decrease in RV infectivity titers. Western blot analyses performed on the infected cell lysates complemented the infectivity titrations and indicated a significant decrease in viral replication. These studies show the therapeutic potential of the stilbenoids against RV replication.

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Böhme, Thomas, Mari Egeland, Marianne Lorentzen, Mohamed F. Mady, Michelle F. Solbakk, Krister S. Sæbø, and Kåre B. Jørgensen. "Regiospecific Photochemical Synthesis of Methylchrysenes." Molecules 28, no. 1 (December 28, 2022): 237. http://dx.doi.org/10.3390/molecules28010237.

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Methylated polycyclic aromatic hydrocarbons (PAHs) are suspected to be some of the toxic compounds in crude oil towards marine life and are needed as single compounds for environmental studies. 1-, 3- and 6-methylchrysene (3a,b,c) were prepared as single isomers by photochemical cyclization of the corresponding stilbenoids in the Mallory reaction using stoichiometric amounts of iodine in 82-88% yield. 2-methylchrysene (3d) was prepared by photochemical cyclization where the regioselectivity was controlled by elimination of an ortho-methoxy group under acidic oxygen free conditions in 72% yield. These conditions failed to form 4-methylchrysene from the corresponding stilbenoid. All stilbenoids were made from a common naphthyl Wittig salt and suitably substituted benzaldehydes. We have also demonstrated that methylchrysenes can be oxidized to the corresponding chrysenecarboxylic acids by KMnO4 in modest yields.

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9

Mattio, Luce Micaela, Giorgia Catinella, Sabrina Dallavalle, and Andrea Pinto. "Stilbenoids: A Natural Arsenal against Bacterial Pathogens." Antibiotics 9, no. 6 (June 18, 2020): 336. http://dx.doi.org/10.3390/antibiotics9060336.

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The escalating emergence of resistant bacterial strains is one of the most important threats to human health. With the increasing incidence of multi-drugs infections, there is an urgent need to restock our antibiotic arsenal. Natural products are an invaluable source of inspiration in drug design and development. One of the most widely distributed groups of natural products in the plant kingdom is represented by stilbenoids. Stilbenoids are synthesised by plants as means of protection against pathogens, whereby the potential antimicrobial activity of this class of natural compounds has attracted great interest in the last years. The purpose of this review is to provide an overview of recent achievements in the study of stilbenoids as antimicrobial agents, with particular emphasis on the sources, chemical structures, and the mechanism of action of the most promising natural compounds. Attention has been paid to the main structure modifications on the stilbenoid core that have expanded the antimicrobial activity with respect to the parent natural compounds, opening the possibility of their further development. The collected results highlight the therapeutic versatility of natural and synthetic resveratrol derivatives and provide a prospective insight into their potential development as antimicrobial agents.

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Pilati, Stefania, Giulia Malacarne, David Navarro-Payá, Gabriele Tomè, Laura Riscica, Valter Cavecchia, José Tomás Matus, Claudio Moser, and Enrico Blanzieri. "Vitis OneGenE: A Causality-Based Approach to Generate Gene Networks in Vitis vinifera Sheds Light on the Laccase and Dirigent Gene Families." Biomolecules 11, no. 12 (November 23, 2021): 1744. http://dx.doi.org/10.3390/biom11121744.

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The abundance of transcriptomic data and the development of causal inference methods have paved the way for gene network analyses in grapevine. Vitis OneGenE is a transcriptomic data mining tool that finds direct correlations between genes, thus producing association networks. As a proof of concept, the stilbene synthase gene regulatory network obtained with OneGenE has been compared with published co-expression analysis and experimental data, including cistrome data for MYB stilbenoid regulators. As a case study, the two secondary metabolism pathways of stilbenoids and lignin synthesis were explored. Several isoforms of laccase, peroxidase, and dirigent protein genes, putatively involved in the final oxidative oligomerization steps, were identified as specifically belonging to either one of these pathways. Manual curation of the predicted sequences exploiting the last available genome assembly, and the integration of phylogenetic and OneGenE analyses, identified a group of laccases exclusively present in grapevine and related to stilbenoids. Here we show how network analysis by OneGenE can accelerate knowledge discovery by suggesting new candidates for functional characterization and application in breeding programs.

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Treml, Leláková, Šmejkal, Paulíčková, Labuda, Granica, Havlík, Jankovská, Padrtová, and Hošek. "Antioxidant Activity of Selected Stilbenoid Derivatives in a Cellular Model System." Biomolecules 9, no. 9 (September 9, 2019): 468. http://dx.doi.org/10.3390/biom9090468.

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The stilbenoids, a group of naturally occurring phenolic compounds, are found in a variety of plants, including some berries that are used as food or for medicinal purposes. They are known to be beneficial for human health as anti-inflammatory, chemopreventive, and antioxidative agents. We have investigated a group of 19 stilbenoid substances in vitro using a cellular model of THP-1 macrophage-like cells and pyocyanin-induced oxidative stress to evaluate their antioxidant or pro-oxidant properties. Then we have determined any effects that they might have on the expression of the enzymes catalase, glutathione peroxidase, and heme oxygenase-1, and their effects on the activation of Nrf2. The experimental results showed that these stilbenoids could affect the formation of reactive oxygen species in a cellular model, producing either an antioxidative or pro-oxidative effect, depending on the structure pinostilbene (2) worked as a pro-oxidant and also decreased expression of catalase in the cell culture. Piceatannol (4) had shown reactive oxygen species (ROS) scavenging activity, whereas isorhapontigenin (18) had a mild direct antioxidant effect and activated Nrf2-antioxidant response element (ARE) system and elevated expression of Nrf2 and catalase. Their effects shown on cells in vitro warrant their further study in vivo.

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Kivimäki, Konsta, Tiina Leppänen, Mari Hämäläinen, Katriina Vuolteenaho, and Eeva Moilanen. "Pinosylvin Shifts Macrophage Polarization to Support Resolution of Inflammation." Molecules 26, no. 9 (May 8, 2021): 2772. http://dx.doi.org/10.3390/molecules26092772.

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Pinosylvin is a natural stilbenoid found particularly in Scots pine. Stilbenoids are a group of phenolic compounds identified as protective agents against pathogens for many plants. Stilbenoids also possess health-promoting properties in humans; for instance, they are anti-inflammatory through their suppressing action on proinflammatory M1-type macrophage activation. Macrophages respond to environmental changes by polarizing towards proinflammatory M1 phenotype in infection and inflammatory diseases, or towards anti-inflammatory M2 phenotype, mediating resolution of inflammation and repair. In the present study, we investigated the effects of pinosylvin on M2-type macrophage activation, aiming to test the hypothesis that pinosylvin could polarize macrophages from M1 to M2 phenotype to support resolution of inflammation. We used lipopolysaccharide (LPS) to induce M1 phenotype and interleukin-4 (IL-4) to induce M2 phenotype in J774 murine and U937 human macrophages, and we measured expression of M1 and M2-markers. Interestingly, along with inhibiting the expression of M1-type markers, pinosylvin had an enhancing effect on the M2-type activation, shown as an increased expression of arginase-1 (Arg-1) and mannose receptor C type 1 (MRC1) in murine macrophages, and C-C motif chemokine ligands 17 and 26 (CCL17 and CCL26) in human macrophages. In IL-4-treated macrophages, pinosylvin enhanced PPAR-γ expression but had no effect on STAT6 phosphorylation. The results show, for the first time, that pinosylvin shifts macrophage polarization from the pro-inflammatory M1 phenotype towards M2 phenotype, supporting resolution of inflammation and repair.

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Laavola, Mirka, Tiina Leppänen, Mari Hämäläinen, Katriina Vuolteenaho, Teemu Moilanen, Riina Nieminen, and Eeva Moilanen. "IL-6 in Osteoarthritis: Effects of Pine Stilbenoids." Molecules 24, no. 1 (December 29, 2018): 109. http://dx.doi.org/10.3390/molecules24010109.

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Interleukin-6 (IL-6) is involved in the pathogenesis of various inflammatory diseases, like rheumatoid arthritis (RA). In the present study, we investigated the role of IL-6 in osteoarthritis (OA) patients and the effects of the stilbenoids monomethyl pinosylvin and pinosylvin on the expression of the cartilage matrix components aggrecan and collagen II and the inflammatory cytokine IL-6 in human OA chondrocytes. Synovial fluid and plasma samples were obtained from 100 patients with severe OA [BMI 29.7 (8.3) kg/m2, age 72 (14) years, median (IQR); 62/38 females/males] undergoing total knee replacement surgery. IL-6 and matrix metalloproteinase (MMP) concentrations in synovial fluid and plasma were measured by immunoassay. The effects of pinosylvin on the expression of IL-6, aggrecan, and collagen II were studied in primary cultures of human OA chondrocytes. IL-6 levels in synovial fluid from OA patients [119.8 (193.5) pg/mL, median (IQR)] were significantly increased as compared to the plasma levels [3.1 (2.7) pg/mL, median (IQR)] and IL-6 levels in synovial fluid were associated with MMPs and radiographic disease severity. Natural stilbenoids monomethyl pinosylvin and pinosylvin increased aggrecan expression and suppressed IL-6 production in OA chondrocytes. The results propose that IL-6 is produced within OA joints and has an important role in the pathogenesis of OA. Stilbenoid compounds monomethyl pinosylvin and pinosylvin appeared to have disease-modifying potential in OA chondrocytes.

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Miliordos, Dimitrios Evangelos, Anastasios Alatzas, Nikolaos Kontoudakis, Angeliki Kouki, Marianne Unlubayir, Marin-Pierre Gémin, Alexandros Tako, Polydefkis Hatzopoulos, Arnaud Lanoue, and Yorgos Kotseridis. "Abscisic Acid and Chitosan Modulate Polyphenol Metabolism and Berry Qualities in the Domestic White-Colored Cultivar Savvatiano." Plants 11, no. 13 (June 22, 2022): 1648. http://dx.doi.org/10.3390/plants11131648.

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During the last decade, several studies demonstrated the effect of biostimulants on the transcriptional and metabolic profile of grape berries, suggesting their application as a useful viticultural practice to improve grape and wine quality. Herein, we investigated the impact of two biostimulants—abscisic acid (0.04% w/v and 0.08% w/v) and chitosan (0.3% w/v and 0.6% w/v)—on the polyphenol metabolism of the Greek grapevine cultivar, Savvatiano, in order to determine the impact of biostimulants’ application in the concentration of phenolic compounds. The applications were performed at the veraison stage and the impact on yield, berry quality traits, metabolome and gene expression was examined at three phenological stages (veraison, middle veraison and harvest) during the 2019 and 2020 vintages. Results showed that anthocyanins increased during veraison after treatment with chitosan and abscisic acid. Additionally, stilbenoids were recorded in higher amount following the chitosan and abscisic acid treatments at harvest. Both of the abscisic acid and chitosan applications induced the expression of genes involved in stilbenoids and anthocyanin biosynthesis and resulted in increased accumulation, regardless of the vintage. Alterations in other phenylpropanoid gene expression profiles and phenolic compound concentrations were observed as well. Nevertheless, they were mostly restricted to the first vintage. Therefore, the application of abscisic acid and chitosan on the Greek cultivar Savvatiano showed promising results to induce stilbenoid metabolism and potentially increase grape defense and quality traits.

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Bakrim, Saad, Hamza Machate, Taoufiq Benali, Nargis Sahib, Imane Jaouadi, Nasreddine El Omari, Sara Aboulaghras, et al. "Natural Sources and Pharmacological Properties of Pinosylvin." Plants 11, no. 12 (June 9, 2022): 1541. http://dx.doi.org/10.3390/plants11121541.

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Pinosylvin (3,5-dihydroxy-trans-stilbene), a natural pre-infectious stilbenoid toxin, is a terpenoid polyphenol compound principally found in the Vitaceae family in the heartwood of Pinus spp. (e.g., Pinus sylvestris) and in pine leaf (Pinus densiflora). It provides defense mechanisms against pathogens and insects for many plants. Stilbenoids are mostly found in berries and fruits but can also be found in other types of plants, such as mosses and ferns. This review outlined prior research on pinosylvin, including its sources, the technologies used for its extraction, purification, identification, and characterization, its biological and pharmacological properties, and its toxicity. The collected data on pinosylvin was managed using different scientific research databases such as PubMed, SciFinder, SpringerLink, ScienceDirect, Wiley Online, Google Scholar, Web of Science, and Scopus. In this study, the findings focused on pinosylvin to understand its pharmacological and biological activities as well as its chemical characterization to explore its potential therapeutic approaches for the development of novel drugs. This analysis demonstrated that pinosylvin has beneficial effects for various therapeutic purposes such as antifungal, antibacterial, anticancer, anti-inflammatory, antioxidant, neuroprotective, anti-allergic, and other biological functions. It has shown numerous and diverse actions through its ability to block, interfere, and/or stimulate the major cellular targets responsible for several disorders.

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Yang, Tony, Cayla Boycott, Katarzyna Lubecka, and Barbara Stefanska. "BRUNOL5 as a Novel Oncogene Is Epigenetically Regulated by Stilbenoids in Primary Liver Cancer Cells." Current Developments in Nutrition 5, Supplement_2 (June 2021): 287. http://dx.doi.org/10.1093/cdn/nzab036_029.

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Abstract Objectives We previously discovered that a novel gene, BRUNOL5, is hypomethylated at the promoter region and upregulated in patients with primary liver cancer. Since DNA hypomethylation was shown to underlie up-regulation of genes with oncogenic functions, BRUNOL5 could potentially act as an oncogene. Interestingly, certain dietary compounds such as polyphenols with a stilbenoid ring have been demonstrated by us and others to suppress hypomethylated cancer-driving genes. In the present study, we investigate BRUNOL5 oncogenic functions and the role of two stilbenoids, resveratrol (RSV) and pterostilbene (PTS), in BRUNOL5 transcriptional regulation. Methods Liver cancer cells, HepG2 and SkHep1, were treated with 15µM RSV or 10µM PTS for 9 days followed by the analysis of cell growth (trypan blue exclusion test), anchorage-independent growth (soft-agar assay), and invasiveness (Boyden chamber assay). The effect on BRUNOL5 promoter methylation and gene expression was assessed by pyrosequencing and QPCR, respectively. BRUNOL5 was then depleted in HepG2 cells using siRNA followed by RNA sequencing to establish gene expression profiles. Results BRUNOL5 was down-regulated by 95% in response to RSV and by 25–50% in response to PTS. This coincided with 10–15% hypermethylation of BRUNOL5 promoter. This effect on BRUNOL5 transcriptional regulation was associated with robust decrease in cell growth, anchorage independent growth and invasiveness. Interestingly, depletion of BRUNOL5 in HepG2 cells mimicked polyphenols’ anti-cancer effects. Further investigation by RNA sequencing in BRUNOL5-depleted cells established gene targets potentially regulated by BRUNOL5. We found 4,406 genes significantly differentially expressed in response to BRUNOL5 knockdown. The top downregulated genes included cancer-promoting genes such as FAIM2, AMOTL1, and MMP2; whereas tumor suppressor genes such as MT1G, CADH1, and ALDH1L1 were among genes with the highest upregulation. Conclusions Our findings demonstrate that BRUNOL5 is a novel target of stilbenoids and acts as an oncogene in liver cancer. RSV and PTS may exert their anti-cancer effects, at least partially, through BRUNOL5 downregulation. Funding Sources UBC VP Academic Award, CFI John. R. Evans Leaders Fund, and BC Knowledge Development Fund granted to BS

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Wen, Haichao, Zheng Fu, Yangji Wei, Xiaoxu Zhang, Liyan Ma, Liwei Gu, and Jingming Li. "Antioxidant Activity and Neuroprotective Activity of Stilbenoids in Rat Primary Cortex Neurons via the PI3K/Akt Signalling Pathway." Molecules 23, no. 9 (September 12, 2018): 2328. http://dx.doi.org/10.3390/molecules23092328.

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Antioxidant activity and neuroprotective activity of three stilbenoids, namely, trans-4-hydroxystilbene (THS), trans-3,5,4′-trihydroxy-stilbene (resveratrol, RES), and trans-3′,4′,3,5-tetrahydroxy-stilbene (piceatannol, PIC), against β-amyloid (Aβ)-induced neurotoxicity in rat primary cortex neurons were evaluated. THS, RES, and PIC significantly scavenged DPPH• and •OH radicals. All three stilbenoids were able to inhibit Aβ neurotoxicity by decreasing intracellular reactive oxygen species (ROS) via the PI3K/Akt signalling pathway. Specifically, stilbenoids significantly promoted Akt phosphorylation; suppressed Bcl-2/Bax expression; and inhibited caspase-9, caspase-3, and PARP cleavage. Molecular docking between stilbenoids with Akt indicated that stilbenoids could form hydrogen bond interactions with the COOH-terminal region of Akt. Additionally, the neuroprotective activity of stilbenoids correlated with the number and position of hydroxyl groups. The lack of meta-dihydroxyl groups on THS did not affect its neuroprotective activity in comparison with RES, whereas the ortho-dihydroxyl moiety on PIC significantly enhanced neuroprotective activity. These results provide new insights into the correlation between the biological activity and chemical structure of stilbenoids.

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Jarosova, Veronika, Ondrej Vesely, Petr Marsik, Jose Jaimes, Karel Smejkal, Pavel Kloucek, and Jaroslav Havlik. "Metabolism of Stilbenoids by Human Faecal Microbiota." Molecules 24, no. 6 (March 23, 2019): 1155. http://dx.doi.org/10.3390/molecules24061155.

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Stilbenoids are dietary phenolics with notable biological effects on humans. Epidemiological, clinical, and nutritional studies from recent years have confirmed the significant biological effects of stilbenoids, such as oxidative stress protection and the prevention of degenerative diseases, including cancer, cardiovascular diseases, and neurodegenerative diseases. Stilbenoids are intensively metabolically transformed by colon microbiota, and their corresponding metabolites might show different or stronger biological activity than their parent molecules. The aim of the present study was to determine the metabolism of six stilbenoids (resveratrol, oxyresveratrol, piceatannol, thunalbene, batatasin III, and pinostilbene), mediated by colon microbiota. Stilbenoids were fermented in an in vitro faecal fermentation system using fresh faeces from five different donors as an inoculum. The samples of metabolized stilbenoids were collected at 0, 2, 4, 8, 24, and 48 h. Significant differences in the microbial transformation among stilbene derivatives were observed by liquid chromatography mass spectrometry (LC/MS). Four stilbenoids (resveratrol, oxyresveratrol, piceatannol and thunalbene) were metabolically transformed by double bond reduction, dihydroxylation, and demethylation, while batatasin III and pinostilbene were stable under conditions simulating the colon environment. Strong inter-individual differences in speed, intensity, and pathways of metabolism were observed among the faecal samples obtained from the donors.

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Meier, Herbert, and Matthias Lehmann. "Stilbenoide Dendrimere." Angewandte Chemie 110, no. 5 (March 2, 1998): 666–69. http://dx.doi.org/10.1002/(sici)1521-3757(19980302)110:5<666::aid-ange666>3.0.co;2-0.

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20

Mohammadhosseinpour, Sepideh, Alexx Weaver, Meenakshi Sudhakaran, Linh-Chi Ho, Tra Le, Andrea I. Doseff, and Fabricio Medina-Bolivar. "Arachidin-1, a Prenylated Stilbenoid from Peanut, Enhances the Anticancer Effects of Paclitaxel in Triple-Negative Breast Cancer Cells." Cancers 15, no. 2 (January 7, 2023): 399. http://dx.doi.org/10.3390/cancers15020399.

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Triple-negative breast cancer (TNBC) is one of the deadliest forms of breast cancer. Investigating alternative therapies to increase survival rates for this disease is essential. To this end, the cytotoxic effects of the prenylated stilbenoids arachidin-1 (A-1) and arachidin-3 (A-3), and non-prenylated resveratrol (RES) were evaluated in human TNBC cell lines as potential adjuvants for paclitaxel (Pac). A-1, alone or in combination with Pac, showed the highest cytotoxicity in TNBC cells. Apoptosis was further evaluated by measuring key apoptosis marker proteins, cell cycle arrest, and intracellular reactive oxygen species (ROS) generation. Furthermore, the cytotoxic effect of A-1 combined with Pac was also evaluated in a 3D spheroid TNBC model. The results showed that A-1 decreased the Pac IC50 approximately 2-fold in TNBC cells. The synergistic combination of A-1 and Pac arrested cells in G2/M phase and activated p53 expression. In addition, the combined treatment increased intracellular ROS generation and induced apoptosis. Importantly, the combination of A-1 with Pac inhibited TNBC spheroid growth. Our results demonstrated that A-1 in combination with Pac inhibited cell proliferation, induced apoptosis through mitochondrial oxidative stress, and reduced TNBC spheroid growth. These findings underscore the impactful effects of the prenylated stilbenoid A-1 as a novel adjuvant for Pac chemotherapy in TNBC treatment.

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21

Fang, Lingling, Tianhong Yang, and Fabricio Medina-Bolivar. "Production of Prenylated Stilbenoids in Hairy Root Cultures of Peanut (Arachis hypogaea) and Its Wild Relatives A. ipaensis and A. duranensis via an Optimized Elicitation Procedure." Molecules 25, no. 3 (January 24, 2020): 509. http://dx.doi.org/10.3390/molecules25030509.

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Prenylated stilbenoids are phenolic compounds produced in a small number of plants such as peanut (Arachis hypogaea) to counteract biotic and abiotic stresses. In addition to their role in plant defense, they exhibit biological activities with potential application in human health. Whereas non-prenylated stilbenoids such as resveratrol are commercially available, the availability of prenylated stilbenoids is limited. To this end, hairy root cultures of peanut were developed as an elicitor-controlled bioproduction platform for prenylated stilbenoids. An orthogonal array design approach led to the elucidation of an optimized elicitation procedure consisting of co-treatment of the hairy root cultures with 18 g/L methyl-β-cyclodextrin, 125 µM methyl jasmonate, 3 mM hydrogen peroxide (H2O2) and medium supplementation with additional 1 mM magnesium chloride. After 168-h of elicitor treatment, the combined yield of the prenylated stilbenoids arachidin-1, arachidin-2, arachidin-3 and arachidin-5 reached approximately 750 mg/L (equivalent to 107 mg/g DW). Moreover, hairy root cultures from the wild Arachis species A. duranensis and A. ipaensis were developed and shown to produce prenylated stilbenoids upon elicitor treatment. These wild Arachis hairy root lines may provide a platform to elucidate the biosynthetic origin of prenylated stilbenoids in peanut.

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22

Aneklaphakij, Chaiwat, Phatthilakorn Chamnanpuen, Somnuk Bunsupa, and Veena Satitpatipan. "Recent Green Technologies in Natural Stilbenoids Production and Extraction: The Next Chapter in the Cosmetic Industry." Cosmetics 9, no. 5 (September 6, 2022): 91. http://dx.doi.org/10.3390/cosmetics9050091.

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Stilbenoids are well-known phytoalexins in the group of polyphenolic compounds. Because of their potent bioactivities, including antioxidant, antityrosinase, photoprotective, and antibacterial activities, stilbenoids are utilized as pharmaceutical active ingredient in cosmetic products. Thus, the demand for stilbenoids in the cosmetic industry is increasing. The main sources of stilbenoids are plants. Although plants are green and sustainable source materials, some of them do not allow a regular and constant supply due to seasonal and geographic reasons. Stilbenoids typically have been extracted by conventional organic solvent extraction, and then purified by separation techniques. This method is unfriendly to the environment and may deteriorate human health. Hence, the procedures called “green technologies” are focused on novel extraction methods and sustainable stilbenoids production by using biotechnology. In this review, the chemical structures together with the biosynthesis and current plant sources of resveratrol, oxyresveratrol, and piceatannol are described. Furthermore, recent natural deep eutectic solvents (NADES) for green extraction as well as plant cell cultures for the production of those stilbene compounds are updated.

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23

Meier, Herbert, and Matthias Lehmann. "Stilbenoid Dendrimers." Angewandte Chemie International Edition 37, no. 5 (March 16, 1998): 643–45. http://dx.doi.org/10.1002/(sici)1521-3773(19980316)37:5<643::aid-anie643>3.0.co;2-4.

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24

Meier, Herbert, Matthias Lehmann, and Ute Kolb. "Stilbenoid Dendrimers." Chemistry - A European Journal 6, no. 13 (July 3, 2000): 2462–69. http://dx.doi.org/10.1002/1521-3765(20000703)6:13<2462::aid-chem2462>3.0.co;2-a.

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25

Chichioco Hernandez, Christine L., Irene M. Villaseñor, Frank C. Schroeder, Henry Paulus, and Jon Clardy. "Stilbenoids fromHopea acuminata." Journal of Herbs, Spices & Medicinal Plants 22, no. 1 (January 2, 2016): 92–104. http://dx.doi.org/10.1080/10496475.2015.1042618.

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26

Yang, Xin-Zhou, Chun-Ping Tang, and Yang Ye. "Stilbenoids fromStemona japonica." Journal of Asian Natural Products Research 8, no. 1-2 (January 2006): 47–53. http://dx.doi.org/10.1080/10286020500382678.

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27

Waterman, Peter G. "Biochemistry of Stilbenoids." Biochemical Systematics and Ecology 23, no. 5 (July 1995): 579. http://dx.doi.org/10.1016/0305-1978(95)90006-3.

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28

Packter, N. M. "Biochemistry of stilbenoids." Biochemical Education 23, no. 3 (July 1995): 179. http://dx.doi.org/10.1016/0307-4412(95)90235-x.

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29

Basri, Dayang Fredalina, Lee Wee Xian, Nur Indah Abdul Shukor, and Jalifah Latip. "Bacteriostatic Antimicrobial Combination: Antagonistic Interaction between Epsilon-Viniferin and Vancomycin against Methicillin-ResistantStaphylococcus aureus." BioMed Research International 2014 (2014): 1–8. http://dx.doi.org/10.1155/2014/461756.

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Stilbenoids have been considered as an alternative phytotherapeutic treatment against methicillin-resistantStaphylococcus aureus(MRSA) infection. The combined effect ofε-viniferin and johorenol A with the standard antibiotics, vancomycin and linezolid, was assessed against MRSA ATCC 33591 and HUKM clinical isolate. The minimum inhibitory concentration (MIC) value of the individual tested compounds and the fractional inhibitory concentration index (FICI) value of the combined agents were, respectively, determined using microbroth dilution test and microdilution checkerboard (MDC) method. Only synergistic outcome from checkerboard test will be substantiated for its rate of bacterial killing using time-kill assay. The MIC value ofε-viniferin against ATCC 33591 and johorenol A against both strains was 0.05 mg/mL whereas HUKM strain was susceptible to 0.1 mg/mL ofε-viniferin. MDC study showed that only combination betweenε-viniferin and vancomycin was synergistic against ATCC 33591 (FICI 0.25) and HUKM (FICI 0.19). All the other combinations (ε-viniferin-linezolid, johorenol A-vancomycin, and johorenol A-linezolid) were either indifferent or additive against both strains. However, despite the FICI value showing synergistic effect forε-viniferin-vancomycin, TKA analysis displayed antagonistic interaction with bacteriostatic action against both strains. As conclusion,ε-viniferin can be considered as a bacteriostatic stilbenoid as it antagonized the bactericidal activity of vancomycin. These findings therefore disputed previous report thatε-viniferin acted in synergism with vancomycin but revealed that it targets similar site in close proximity to vancomycin’s action, possibly at the bacterial membrane protein. Hence, this combination has a huge potential to be further studied and developed as an alternative treatment in combating MRSA in future.

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30

Dávid, Csilla Zsuzsanna, Judit Hohmann, and Andrea Vasas. "Chemistry and Pharmacology of Cyperaceae Stilbenoids: A Review." Molecules 26, no. 9 (May 10, 2021): 2794. http://dx.doi.org/10.3390/molecules26092794.

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Cyperaceae is a cosmopolitan plant family with approx. 5000 species distributed worldwide. Several members of this family are used in traditional medicines for the treatment of different diseases. In the last few decades, constituents with great chemical diversity were isolated from sedges, and a wide range of biological activities were detected either for crude extracts or for pure compounds. Among the isolated compounds, phenolic derivatives are the most important, especially stilbenoids, and flavonoids. To date, more than 60 stilbenoids were isolated from 28 Cyperaceae species. Pharmacological investigation of Cyperaceae stilbenoids revealed that several compounds possess promising activities; mainly antiproliferative, antibacterial, antioxidant and anthelmintic effects. Isolation, synthesis and pharmacological investigation of stilbenes are increasing constantly. As Cyperaceae species are very good sources of a wide variety of stilbenes, and several of them occur in large amount worldwide, they are worthy for phytochemical and pharmacological investigations. Moreover, stilbenes are important from chemotaxonomical point of view, and they play a key role in plant defense mechanisms as well. This review summarizes the stilbenoids isolated from sedges, and their biological activities.

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31

Vesely, Ondrej, Simona Baldovska, and Adriana Kolesarova. "Enhancing Bioavailability of Nutraceutically Used Resveratrol and Other Stilbenoids." Nutrients 13, no. 9 (September 2, 2021): 3095. http://dx.doi.org/10.3390/nu13093095.

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Stilbenoids are interesting natural compounds with pleiotropic in vitro and in vivo activity. Their well-documented biological properties include anti-inflammatory effects, anticancer effects, effects on longevity, and many others. Therefore, they are nowadays commonly found in foods and dietary supplements, and used as a part of treatment strategy in various types of diseases. Bioactivity of stilbenoids strongly depends on different types of factors such as dosage, food composition, and synergistic effects with other plant secondary metabolites such as polyphenols or vitamins. In this review, we summarize the existing in vitro, in vivo, and clinical data from published studies addressing the optimization of bioavailability of stilbenoids. Stilbenoids face low bioavailability due to their chemical structure. This can be improved by the use of novel drug delivery systems or enhancers, which are discussed in this review. Current in vitro and in vivo evidence suggests that both approaches are very promising and increase the absorption of the original substance by several times. However, data from more clinical trials are required.

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32

Ewald, Philipp, Ulf Delker, and Peter Winterhalter. "Quantification of stilbenoids in grapevine canes and grape cluster stems with a focus on long-term storage effects on stilbenoid concentration in grapevine canes." Food Research International 100 (October 2017): 326–31. http://dx.doi.org/10.1016/j.foodres.2017.08.003.

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33

Johnsen, Peter Riber, Cecilia Pinna, Luce Mattio, Mathilde Bech Strube, Mattia Di Nunzio, Stefania Iametti, Sabrina Dallavalle, Andrea Pinto, and Hanne Frøkiær. "Investigation of the Effects of Monomeric and Dimeric Stilbenoids on Bacteria-Induced Cytokines and LPS-Induced ROS Formation in Bone Marrow-Derived Dendritic Cells." International Journal of Molecular Sciences 24, no. 3 (February 1, 2023): 2731. http://dx.doi.org/10.3390/ijms24032731.

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Stilbenoids are anti-inflammatory and antioxidant compounds, with resveratrol being the most investigated molecule in this class. However, the actions of most other stilbenoids are much less studied. This study compares five monomeric (resveratrol, piceatannol, pterostilbene, pinostilbene, and trimethoxy-resveratrol) and two dimeric (dehydro-δ-viniferin and trans-δ-viniferin) stilbenoids for their capability to modulate the production of bacteria-induced cytokines (IL-12, IL-10, and TNF-α), as well as lipopolysaccharide (LPS)-induced reactive oxygen species (ROS), in murine bone marrow-derived dendritic cells. All monomeric species showed dose-dependent inhibition of E. coli-induced IL-12 and TNF-α, whereas only resveratrol and piceatannol inhibited IL-10 production. All monomers, except trimethoxy-resveratrol, inhibited L. acidophilus-induced IL-12, IL-10, and TNF-α production. The dimer dehydro-δ-viniferin remarkably enhanced L. acidophilus-induced IL-12 production. The contrasting effect of resveratrol and dehydro-δ-viniferin on IL-12 production was due, at least in part, to a divergent inactivation of the mitogen-activated protein kinases by the two stilbenoids. Despite having moderate to high total antioxidant activity, dehydro-δ-viniferin was a weak inhibitor of LPS-induced ROS formation. Conversely, resveratrol and piceatannol potently inhibited LPS-induced ROS formation. Methylated monomers showed a decreased antioxidant capacity compared to resveratrol, also depending on the methylation site. In summary, the immune-modulating effect of the stilbenoids depends on both specific structural features of tested compounds and the stimulating bacteria.

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34

Rätsep, Reelika, Kadri Karp, Mariana Maante-Kuljus, Alar Aluvee, Hedi Kaldmäe, and Rajeev Bhat. "Recovery of Polyphenols from Vineyard Pruning Wastes—Shoots and Cane of Hybrid Grapevine (Vitis sp.) Cultivars." Antioxidants 10, no. 7 (June 30, 2021): 1059. http://dx.doi.org/10.3390/antiox10071059.

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Grapevine shoots and canes represent a significant amount of biomass, considered as a waste in viticulture. In cooler climates, grapevines are pruned in the autumn (October) and spring (March) due to harsh winter conditions (e.g., snow, low temperatures), and large amounts of biomass are produced at these different pruning times. This work was undertaken in order to investigate the potential of vineyard pruning waste for recovery of polyphenolic compounds for biomass valorization. Qualitative and quantitative analyses of grapevine shoot and cane polyphenols, including flavonoids and stilbenoids were performed using UHPLC MS/MS method. The results revealed the flavonols (quercetin) to be the most abundant compounds in shoots among all the three cultivars screened (Zilga, Hasansky Sladky, Rondo). Stilbenoids (ε-viniferin) dominated in the canes, while increased level of flavonols with lower contents of stilbenoids was detected in the endo-dormant canes, and higher amounts of flavanols and stilbenoids were recorded in eco-dormant canes. In conclusion, the content of polyphenols in grapevine shoots and canes differed among the cultivars and dormancy phases. The results generated from the present study contribute to the sustainable and environmentally friendly viticulture practice via valorization of vineyard pruning wastes.

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35

Komaikul, Jukrapun, Supachoke Mangmool, Waraporn Putalun, and Tharita Kitisripanya. "Preparation of Readily-to-Use Stilbenoids Extract from Morus alba Callus Using a Natural Deep Eutectic Solvent." Cosmetics 8, no. 3 (September 19, 2021): 91. http://dx.doi.org/10.3390/cosmetics8030091.

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The consumer and cosmetic industries have recently placed a greater emphasis on ecofriendly solvents for botanical extraction, including natural deep eutectic solvents (NADES). In this study, NADES were prepared for Morus alba callus extraction. The efficiency of extraction from the NADES and methanol was investigated by comparison of the stilbenoids yield and anti-melanogenesis activity. Prior to testing the irritability of a suitable NADES on the reconstructed human epidermis (RhE), the effect of the selected NADES on stilbenoids stability was determined. The results showed that the highest yields of stilbenoids were obtained from choline chloride-glycerol mixtures (Ch1G2) and methanol extracts, with no significant difference in yields (5.06 ± 0.05 and 6.32 ± 0.40 mg/g callus dry weight, respectively). The NADES extracts of M. alba callus showed comparable anti-melanogenesis activity compared to methanol. In term of stability, stilbenoids in Ch1G2 remained stable after six months of storage at 4 °C except resveratrol. Furthermore, Ch1G2 had no irritation effect on RhE. Thus, based on the findings of this study, Ch1G2 is an intriguing green solvent alternative for the extraction of M. alba callus and may be advantageous for the preparation of skin-lightening cosmetics.

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36

Akinwumi, Bolanle, Kimberly-Ann Bordun, and Hope Anderson. "Biological Activities of Stilbenoids." International Journal of Molecular Sciences 19, no. 3 (March 9, 2018): 792. http://dx.doi.org/10.3390/ijms19030792.

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37

Zidorn, Christian, Sandra Grass, Ernst P. Ellmerer, Karl-Hans Ongania, and Hermann Stuppner. "Stilbenoids from Tragopogon orientalis." Phytochemistry 67, no. 19 (October 2006): 2182–88. http://dx.doi.org/10.1016/j.phytochem.2006.06.031.

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38

Yang, X. Z., C. P. Tang, C. Q. Ke, and Y. Ye. "Stilbenoids from Stemona sessilifolia." Journal of Asian Natural Products Research 9, no. 3 (May 1, 2007): 261–66. http://dx.doi.org/10.1080/10286020600604310.

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39

Zhang, Ya-Zhong, Guo-Bing Xu, and Tong Zhang. "Antifungal stilbenoids fromStemona japonica." Journal of Asian Natural Products Research 10, no. 7 (July 2008): 634–39. http://dx.doi.org/10.1080/10286020802133555.

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40

Baba, Kimiye, Tadashi Kido, Masahiko Taniguchi, and Mitsugi Kozawaqa. "Stilbenoids from Cassia garrettiana." Phytochemistry 36, no. 6 (August 1994): 1509–13. http://dx.doi.org/10.1016/s0031-9422(00)89752-6.

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41

Pacher, T., C. Seger, D. Engelmeier, S. Vajrodaya, O. Hofer, and H. Greger. "Antifungal Stilbenoids fromStemona collinsae." Journal of Natural Products 65, no. 6 (June 2002): 820–27. http://dx.doi.org/10.1021/np0105073.

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42

Bai, Li, Tomoko Kato, Keiko Inoue, Masae Yamaki, and Shuzo Takagi. "Stilbenoids from Bletilla striata." Phytochemistry 33, no. 6 (August 1993): 1481–83. http://dx.doi.org/10.1016/0031-9422(93)85115-8.

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43

Bai, Li, Masae Yamaki, and Shuzo Takagi. "Stilbenoids from Pleione bulbocodioides." Phytochemistry 42, no. 3 (June 1996): 853–56. http://dx.doi.org/10.1016/0031-9422(95)00068-2.

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44

Kimura, Mutsumi, Hirotoshi Narikawa, Kazuchika Ohta, Kenji Hanabusa, Hirofusa Shirai, and Nagao Kobayashi. "Star-Shaped Stilbenoid Phthalocyanines." Chemistry of Materials 14, no. 6 (June 2002): 2711–17. http://dx.doi.org/10.1021/cm020222r.

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45

MEIER, H., and M. LEHMANN. "ChemInform Abstract: Stilbenoid Dendrimers." ChemInform 29, no. 26 (June 21, 2010): no. http://dx.doi.org/10.1002/chin.199826122.

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46

Tarbeeva, Darya V., Evgeny A. Pislyagin, Ekaterina S. Menchinskaya, Dmitrii V. Berdyshev, Anatoliy I. Kalinovskiy, Valeria P. Grigorchuk, Natalia P. Mishchenko, Dmitry L. Aminin, and Sergey A. Fedoreyev. "Polyphenolic Compounds from Lespedeza bicolor Protect Neuronal Cells from Oxidative Stress." Antioxidants 11, no. 4 (April 3, 2022): 709. http://dx.doi.org/10.3390/antiox11040709.

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Pterocarpans and related polyphenolics are known as promising neuroprotective agents. We used models of rotenone-, paraquat-, and 6-hydroxydopamine-induced neurotoxicity to study the neuroprotective activity of polyphenolic compounds from Lespedeza bicolor and their effects on mitochondrial membrane potential. We isolated 11 polyphenolic compounds: a novel coumestan lespebicoumestan A (10) and a novel stilbenoid 5’-isoprenylbicoloketon (11) as well as three previously known pterocarpans, two pterocarpens, one coumestan, one stilbenoid, and a dimeric flavonoid. Pterocarpans 3 and 6, stilbenoid 5, and dimeric flavonoid 8 significantly increased the percentage of living cells after treatment with paraquat (PQ), but only pterocarpan 6 slightly decreased the ROS level in PQ-treated cells. Pterocarpan 3 and stilbenoid 5 were shown to effectively increase mitochondrial membrane potential in PQ-treated cells. We showed that pterocarpans 2 and 3, containing a 3’-methyl-3’-isohexenylpyran ring; pterocarpens 4 and 9, with a double bond between C-6a and C-11a; and coumestan 10 significantly increased the percentage of living cells by decreasing ROS levels in 6-OHDA-treated cells, which is in accordance with their rather high activity in DPPH• and FRAP tests. Compounds 9 and 10 effectively increased the percentage of living cells after treatment with rotenone but did not significantly decrease ROS levels.

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47

Polunin, K. E., P. N. Kolotilov, V. M. Voitova, A. V. Larin, and I. A. Polunina. "Adsorption of stilbenoids on silica." Protection of Metals and Physical Chemistry of Surfaces 46, no. 1 (January 2010): 64–70. http://dx.doi.org/10.1134/s2070205110010090.

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48

Bai, Li, Noriko Masukawa, Masae Yamaki, and Shuzo Takagi. "Four stilbenoids from Pleione bulbocodioides." Phytochemistry 48, no. 2 (May 1998): 327–31. http://dx.doi.org/10.1016/s0031-9422(97)01110-2.

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49

Kang, Yun-Yao, Yan-Bei Tu, Chao Zhu, Xue-Fei Meng, Yang Yan, Chuan-Hai Wu, and Yan-Fang Li. "Two new stilbenoids fromBletilla striata." Journal of Asian Natural Products Research 21, no. 12 (December 26, 2018): 1170–76. http://dx.doi.org/10.1080/10286020.2018.1526787.

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50

Liu, Xin-Qiao, Qiao-Yu Yuan, and Yuan-Qiang Guo. "Two new stilbenoids fromPleione bulbocodioides." Journal of Asian Natural Products Research 11, no. 2 (February 2009): 116–21. http://dx.doi.org/10.1080/10286020802573370.

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