ABSTRACT
This study induced biological stress in Sorbus pohuashanensis suspension cell(SPSC) with yeast extract(YE) as a bio-tic elicitor and isolated and identified secondary metabolites of triterpenoids produced under stress conditions. Twenty-six triterpenoids, including fifteen ursane-type triterpenoids(1-15), two 18,19-seco-ursane-type triterpenoids(16-17), four lupine-type triterpenoids(18-21), two cycloartane-type triterpenoids(22-23), and three squalene-type triterpenoids(24-26), were isolated and purified from the methanol extract of SPSC by chromatography on silica gel, MCI, Sephadex LH-20, and MPLC. Their structures were elucidated by spectroscopic analyses. All triterpenoids were isolated from SPSC for the first time and 22-O-acetyltripterygic acid A(1) was identified as a new compound. Selected compounds were evaluated for antifungal, antitumor, and anti-inflammatory activities, and compound 1 showed an inhibitory effect on NO production in LPS-induced RAW264.7 cells.
Subject(s)
Pentacyclic Triterpenes , Sorbus , Triterpenes , Animals , Mice , Sorbus/metabolism , Anti-Inflammatory Agents/pharmacology , Anti-Inflammatory Agents/metabolism , RAW 264.7 Cells , Molecular StructureABSTRACT
Thirty four compounds were identified in Sorbus torminalis (L.) fruit extracts of different maturity types by means of LC-DAD-MS (ESI+) fragmentation analysis. Both immature and mature fruits were rich in flavonoid glycosides esterified with hydroxycinnamic, phenolic and dicarboxylic acids along with benzoic, phenylpropanoic and cinnamoyl quinic acid derivatives with many of them being detected for the first time in Sorbus species and in literature. Extracts and fractions were tested for their antioxidant activity (DPPH, chemiluminescence, Rancimat assays) and the estimation of the phenolic content was carried out through Folin-Ciocalteu reagent. Ethyl acetate fraction exhibited the highest scavenging activity determined as EC50 = 1.58 ± 0.22 µg/mL and EC50 = 1.64 ± 0.24 µg/mL for immature and mature fruits respectively with the DPPH test. Chemiluminescence test indicated the same fraction having the strongest antioxidant activity with an IC50 0.41 ± 0.06 µg/mL and IC50 0.50 ± 0.02 µg/mL in both maturity types. The ethyl acetate fraction of the mature fruits is considered the most potent Aldose Reductase 2 (ALR2) inhibitor with 79% demonstrating the high nutritional value of Sorbus torminalis (L.) mature fruits as a defense mechanism against the onset of diabetes mellitus secondary complications leading to the utilization of the plant for nutritional and pharmaceutical purposes.
Subject(s)
Antioxidants , Fruit , Phytochemicals , Plant Extracts , Sorbus , Fruit/chemistry , Sorbus/chemistry , Antioxidants/pharmacology , Antioxidants/isolation & purification , Phytochemicals/pharmacology , Phytochemicals/isolation & purification , Plant Extracts/pharmacology , Plant Extracts/chemistry , Molecular Structure , Phenols/pharmacology , Phenols/isolation & purification , Phenols/analysis , Flavonoids/pharmacology , Flavonoids/isolation & purificationABSTRACT
Sorbus torminalis (L.) Crantz has a rich history of versatile applications spanning the fields of medicine and nutrition. It is noteworthy that the decoction obtained from S. torminalis leaves is a traditional treatment method against both diabetes and stomach disorders. Phytochemical profiling determined by HPLC/MS-MS. The effects of the extracts on cell viability were investigated using the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide) method against MDA-MB-231â cell line (human breast adenocarcinoma).The ethanol/water extract contained more concentration of total phenolic (91.41â mg gallic acid (GAE) equivalent /gr) and flavanoid (29.10â mg rutin (RE) equivalent/gr) in the tested extract (p<0.05). Resulting of HPLC analysis, the chemical constituents varied depending on the solvents and chlorogenic acid, hyperoside, isoquercetin, delphindin-3,5-diglucoside, procyanidin B2, epicatechin, neochlorogenic acid, 3,5-dicaffeoylquinic acid were identified in all extracts. Overall, ethanol, n-hexane and ethyl acetate extracts showed the highest inhibition for the tyrosinase enzyme. The effect of leaf extracts of S. torminalis on antimicrobial, biofilm inhibitory, and anticancer activities was examined. Based on outcomes of our study recognize this plant as a critical source of medically active chemicals for feasible phytopharmaceutical and nutraceutical applications, providing the first scientific insight into the detailed biological and chemical profiles of S. torminalis.
Subject(s)
Sorbus , Humans , Antioxidants/pharmacology , Ethanol , Flavonoids/pharmacology , Phytochemicals/pharmacology , Plant Extracts/pharmacology , Plant Extracts/analysis , Plant Leaves/chemistryABSTRACT
Plant polyphenols are characterized by a wide range of biological activities, including antioxidant properties, and have a high geroprotective potential. The purpose of this work was to investigate the effect of the extract of rowan berries (Sorbus aucuparia L.) on the lifespan and stress resistance of Drosophila melanogaster with the identification of possible mechanisms of its biological activity. It has been established that an ethanol extract of S. aucuparia berries, the main components of which are rutin and cyanidin-3-rutinoside, has a pronounced antioxidant activity in vitro. At the same time, treatment with rowan berry extract increased the resistance of D. melanogaster males to starvation, but reduced resistance to hyperthermia. In females, the extract reduced resistance to oxidative stress but increased resistance to hyperthermia. The effects of rowan berry extract on longevity depended both on its concentration and on the sex of fruit flies. In response to treatment with rowan berry extract, D. melanogaster males and females showed slight differences in the background level of expression of cellular stress response genes, including heat shock genes (hsp27, hsp68, and hsp83), oxidative stress resistance genes (hif1, nrf2, and sod1), circadian rhythm genes (clk and per), and the longevity gene sirt1, which may explain the differences in the observed effects.
Subject(s)
Antioxidants , Sorbus , Animals , Female , Male , Antioxidants/pharmacology , Antioxidants/metabolism , Sorbus/metabolism , Fruit/metabolism , Drosophila melanogaster/genetics , Drosophila melanogaster/metabolism , Plant Extracts/pharmacologyABSTRACT
In spite of its well-known nephrotoxicity, gentamicin is nonetheless routinely used in humans and animals. However, no adjuvant treatments have been implemented to mitigate this harmful effect. Given this concern, medicinal plants represent a significant reservoir of natural antioxidants that could potentially reduce the renal oxidative stress induced by gentamicin. Therefore, the main objective of this research was to investigate the nephroprotective properties of Cornus mas and Sorbus aucuparia fruits in an experimental model of nephrotoxicity. The 3-week study was performed on male Wistar rats, which were randomly divided into six experimental groups, being subcutaneously treated with 50 mg/kg gentamicin and orally given Cornus mas and Sorbus aucuparia extracts, in doses of 40 mg/kg and 10 mg/kg, respectively. Antioxidant therapy significantly improved the nitro-oxidative stress parameters as well as the specific renal biomarkers KIM-1 and iNAG, demonstrating a considerable renal tubular protective impact. These outcomes were reinforced by biochemical and histopathological enhancements. Nevertheless, neither of the tested extracts succeeded in substantially diminishing BUN levels. Additionally, CysC did not significantly decline following extracts treatment, suggesting that the remedies did not effectively protect renal glomeruli against gentamicin stress. Future studies are required in order to determine the underlying mechanisms of these berries.
Subject(s)
Cornus , Renal Insufficiency , Sorbus , Rats , Humans , Animals , Antioxidants/pharmacology , Antioxidants/chemistry , Rats, Wistar , Cornus/chemistry , Gentamicins/toxicity , Sorbus/chemistry , Oxidative Stress , Plant Extracts/pharmacology , Plant Extracts/chemistry , BiomarkersABSTRACT
Osteoarthritis (OA) is a widespread joint disease that affects millions of people worldwide. Conventional treatments for OA, including non-steroidal anti-inflammatory drugs (NSAIDs) and steroids, have a risk of various adverse events, including liver, gastrointestinal, cardiovascular, and kidney disease, which are unsatisfactory in their effectiveness. In this study, Sorbus commixta Hedl. Stem extracts (SCE) were evaluated in animal models as potential inhibitors for the progression of OA. Sorbus commixta Hedl., which was found to have substantial anti-inflammatory and antioxidant activities in earlier investigations, has shown potential as a candidate for OA treatment. To mimic human OA symptoms, male rats were injected using sodium iodoacetate (MIA) in their knee joints. SCE significantly reduced MIA-induced weight-bearing loss in rats after the MIA injection and alleviated cartilage degradation and subchondral bone injury caused by MIA. In addition, SCE administration reduced levels of TNF-α and IL-1ß such as pro-inflammatory cytokines in serum, as well as the levels of matrix metalloproteinases (MMPs) such as MMP-1, -3, -8 and -13 in the joint cartilage. SCE significantly inhibited the writhing responses in acetic acid-administered mice and was used to quantify pain. In lipopolysaccharide (LPS)-activated RAW264.7, SCE suppressed NO production and reduced the expression of TNF-α, PGE2, IL-6, IL-1ß, MMP1, MMP3, MMP8, and MMP-13. Our study showed that SCE alleviated inflammation and cartilage degradation in arthritis through its anti-inflammatory activities on multiple targets.
Subject(s)
Cartilage, Articular , Osteoarthritis , Sorbus , Humans , Male , Animals , Mice , Rats , Arthralgia/drug therapy , Anti-Inflammatory Agents/pharmacology , Pain/drug therapy , Osteoarthritis/chemically induced , Osteoarthritis/drug therapy , Models, TheoreticalABSTRACT
We studied the effect of an anthocyanin-containing complex from the fruits of S. aucuparia L. on doxorubicin-induced genotoxicity in bone marrow cells of C57BL/6 mice. The complex reduced the genotoxic effect doxorubicin in metaphase plates of bone marrow cells in 24, 48 h, and 10 days after the administration of the cytostatic. The mean number of single fragments and the fraction of cells with gaps and aberrant metaphases also decreased.
Subject(s)
Sorbus , Animals , Mice , Anthocyanins/pharmacology , Fruit , Mice, Inbred C57BL , Plant Extracts/pharmacologyABSTRACT
Plant stress memory can provide the benefits of enhanced protection against additional stress exposure. Here, we aimed to explore the responses of recurrent and non-recurrent yeast extract (YE) stresses in Sorbus pohuashanensis suspension cells (SPSCs) at metabolomics and transcriptional levels. Biochemical analyses showed that the cell wall integrity and antioxidation capacity of SPSCs in the pretreated group were evidently improved. Metabolic analysis showed that there were 39 significantly altered metabolites in the pretreated group compared to the non-pretreated group. Based on the transcriptome analysis, 219 differentially expressed genes were obtained, which were highly enriched in plant-pathogen interaction, circadian rhythm-plant, oxidative phosphorylation, and phenylpropanoid biosynthesis. Furthermore, the correlation analysis of the transcriptome and metabolome data revealed that phenylpropanoid biosynthesis involved in the production of biphenyl phytoalexins may play a critical role in the memory response of SPSC to YE, and the key memory genes were also identified, including PAL1, BIS1, and BIS3. Collectively, the above results demonstrated that the memory responses of SPSC to YE were significant in almost all levels, which would be helpful for better understanding the adaptation mechanisms of medicinal plants in response to biotic stress, and laid a biotechnological foundation to accumulate favorable antimicrobial drug candidates from plant suspension cells.
Subject(s)
Sorbus , Sorbus/genetics , Sorbus/metabolism , Plant Cells/metabolism , Secondary Metabolism/genetics , Antioxidants/metabolismABSTRACT
BACKGROUND: The 39-item ROwan Foot Pain Assessment Questionnaire (ROFPAQ) has affective, cognitive, and sensory dimensions to evaluate chronic foot pain. However, to date, the ROFPAQ has only been validated in English and Spanish versions. A simplified Chinese version of ROFPAQ is still not available, even though China has a large population of patients with foot pain. OBJECTIVE: This study's aim was to translate the ROFPAQ into a Chinese version and assess its reliability and validity in Chinese patients with chronic foot pain. STUDY DESIGN: A cross-sectional, multicenter descriptive study. SETTING: This study took place at the Chinese PLA General Hospital, PLA Strategic Support Force Characteristic Medical Center and Wenzhou integrated traditional Chinese and Western Medicine Hospital Affiliated to Zhejiang traditional Chinese Medicine University. METHODS: The ROFPAQ-C (Chinese) was developed by a forward/backward translation protocol and cross-cultural adaptation from the United Kingdom to China, and from English to Chinese Putonghua. A total of 194 patients from 3 centers with chronic foot pain were recruited for test-retest measures from July 2020 though September 2021. RESULTS: Adequate internal consistencies (Cronbach's Alpha) in 3 domains ranged from 0.875 to 0.799 for the cognitive, from 0.795 to 0.629 for the affective, and from 0.801 to 0.811 for the sensory, as well as for the total score from 0.880 to 0.815. Adequate test-retest reliability by intraclass correlation coefficient (ICC) were shown in the cognitive 0.712 (95% CI 0.636 to 0.775), the affective 0.929 (95% CI 0.906 to 0.946), the sensory 0.753 (95% CI 0.685 to 0.808), and the total score 0.932 (95% CI 0.910 to 0.948). Adequate item-total correlations were shown for the cognitive from 0.848 to 0.825, the affective from 0.918 to 0.908, and the sensory from 0.943 to 0.855. LIMITATIONS: The original ROFPAQ with 39 items was developed from a podiatry department of the health care national service of the United Kingdom. CONCLUSIONS: The ROFPAQ-C can be used as a valid and reliable tool for chronic foot pain in the Chinese population.
Subject(s)
Chronic Pain , Foot Diseases , Sorbus , China , Cross-Sectional Studies , Humans , Pain Measurement/methods , Polyesters , Psychometrics , Reproducibility of Results , Surveys and QuestionnairesABSTRACT
Firstly, the antioxidant capacity of total flavonoids that was extracted from Sorbus pohuashanensis (Hance) Hedl was determined by ABTS+·radical-scavenging method, and MTT assay was used to mensurate the anti-tumor activity of total flavonoids In Vitro. Subsequently, the extraction conditions of flavonoids were optimized by the response surface methodology, the antioxidant activity was investigated simultaneously. Furthermore, the anti-tumor activity mechanism of flavonoids was simulated by molecular docking software. The antioxidant activity of flavonoids was correlated with the content in the process of optimizing the extraction condition. Moreover, The MTT assay revealed that SPF inhibited the activity of four sorts of cancer cells and positively correlated with the concentration of total flavonoids. And the experimental data demonstrated its anticancer activity was better at high concentrations. Finally, its anti-tumor activity was found that may be related to small molecules from flavonoids bind the apoptotic proteins Caspase-3, Caspase-8, and Caspase-9. The study could provide a theoretical basis for further pharmacodynamic research of Sorbus pohuashanensis (Hance) Hedl flavonoids, and improved a valuable attribute to Sorbus pohuashanensis (Hance) Hedl.
Subject(s)
Sorbus , Antioxidants/pharmacology , Flavonoids/pharmacology , Molecular Docking Simulation , Plant Extracts/pharmacologyABSTRACT
This paper studies the effect of different ultrasonic parameters on the yield of extraction and antioxidant activity of selected phenolic compounds from Sorbus intermedia berries. The sonication was carried out in two modes: continuous and pulse. In the pulse mode, the samples were sonicated with the following processor settings: 1 s on-2 s off. The effective ultrasonic processor times were 5, 10, and 15 min, and the total extraction times were 15, 30, and 45 min. The results showed that the duty cycle significantly affected the antioxidant activity of the extracts and the yield of chlorogenic acid, rutin, and total flavonoids. Compared to the continuous mode, the pulse ultrasound increased the extraction yield of rutin by 5-27%, chlorogenic acid by 12-29%, and total flavonoids by 8-42%. The effect of the duty cycle on the extraction yield was dependent on the intensity and duration of the ultrasound treatment. The mechanism of the influence of the pulsed ultrasound field on the extraction process has been elucidated. This research clearly demonstrated the superiority of pulsed ultrasound-assisted extraction for production of antioxidants from Sorbus intermedia berries.
Subject(s)
Sorbus , Antioxidants , Chlorogenic Acid , Flavonoids , Phenols , Plant Extracts , Rutin , UltrasonicsABSTRACT
Sorbus pohuashanensis (Hance) Hedl. is a potential horticulture and medicinal plant, but its genomic and genetic backgrounds remain unknown. Here, we sequence and assemble the S. pohuashanensis reference genome using PacBio long reads. Based on the new reference genome, we resequence a core collection of 22 Sorbus spp. samples, which are divided into 2 groups (G1 and G2) based on phylogenetic and PCA analyses. These phylogenetic clusters are highly consistent with their classification based on leaf shape. Natural hybridization between the G1 and G2 groups is evidenced by a sample (R21) with a highly heterozygous genotype. Nucleotide diversity (π) analysis shows that G1 has a higher diversity than G2 and that G2 originated from G1. During the evolution process, the gene families involved in photosynthesis pathways expanded and the gene families involved in energy consumption contracted. RNA-seq data suggests that flavonoid biosynthesis and heat-shock protein (HSP)-heat-shock factor (HSF) pathways play important roles in protection against sunburn. This study provides new insights into the evolution of Sorbus spp. genomes. In addition, the genomic resources, and the identified genetic variations, especially those related to stress resistance, will help future efforts to produce and breed Sorbus spp.
Subject(s)
Sorbus , Sunburn , Phylogeny , Plant Breeding , Plant Leaves/genetics , Sorbus/genetics , Transcriptome/geneticsABSTRACT
Environment stress can promote the synthesis and accumulation of a series of secondary metabolites, which are important quality factors in medicinal plants. However, the data related to metabolites is often too large, making it difficult to screen quickly, accurately and comprehensively various differential compounds. In this study, a high-throughput screening method for differential secondary metabolites produced by medicinal plants under environmental stress has been developed based on ultrahigh performance liquid chromatography-quadrupole time-of-flight mass spectrometry (UHPLC-QTOF) and automatic data analysis strategy. This work uses Sorbus pohuashanensis cells with biotic stress (Harpin protein) and abiotic stress (Cd2+ ) as potential environmental stress factors. The results showed that S. pohuashanensis cells could rapidly respond to both Harpin protein and Cd2+ within 24 h, and a significant positive correlation was observed between their concentration (within a certain range) and induction time. The proposed screening method can automatically screen the bulk UHPLC-QTOF metabolic data for differential compounds with high-throughput, and also perform preliminary identification of their possible structures. The screening results indicated that the stress response of S. pohuashanensis cells to Cd2+ was significantly higher than that of Harpin protein, and all of them could produce a series of biphenyls, terpenes, and other phytoalexins with stress-resistance and physiological functional properties. Overall, the screening method provides an efficient and powerful tool to study the response mechanisms of plants to environmental stress, to improve the resistance of medicinal plants and also to select and breed high-quality Chinese medicinal plants.
Subject(s)
Sorbus , Chromatography, High Pressure Liquid , High-Throughput Screening Assays , Mass Spectrometry , Stress, PhysiologicalABSTRACT
Sorbus aucuparia L. is a source of edible fruits appreciated for their nutritional and medicinal properties. In this work some bioactivity mechanisms were evaluated, which might be connected with the traditional application of rowanberries in cardiovascular complications of diabetes. With the use of a panel of chemical and biological in vitro models the rowanberry extracts were proved to significantly inhibit the formation of advanced glycation end products, neutralise multiple oxidants generated in vivo, increase the non-enzymatic antioxidant capacity of human plasma and protect plasma components (proteins and lipids) against oxidative/nitrative damage at in vivo-relevant levels (1-5 µg/mL). Moreover, the extracts were found safe in cytotoxicity tests on the peripheral blood mononuclear cells. The comprehensive phytochemical profiling of the extracts (RP/HILIC-UHPLC-PDA-ESI-MS3, HPLC-PDA, and UV-spectrophotometric methods) led to the identification of 51 phenolics, including caffeic and ferulic acids pseudodepsides (34 compounds, prevailing isomers of chlorogenic acid and cynarin, total content up to 269.4 mg/g), flavonols (mostly quercetin glycosides, up to 5.8 mg/g), flavan-3-ol derivatives (proanthocyanidin oligomers and polymers, up to 17.0 mg/g), and simple phenolic acids. The experiments on model constituents of the extracts and correlation studies were used to evaluate contribution of polyphenols to the observed effects. Taking into account the possible additive and synergistic effects, the co-occurrence of various compounds was indicated as partly responsible for biological activity of the fruits. Considering both the composition and activity parameters, the methanol-water (1:1, v/v) extract and its concentrated phenolic fractions appeared to be the most advantageous for biological application.
Subject(s)
Sorbus , Fruit , Humans , Leukocytes, Mononuclear , Oxidative Stress , Phytochemicals/pharmacology , Plant Extracts/pharmacologyABSTRACT
Recent trends in the food industry combined with novel methods in agriculture could transform rowan into a valuable raw material with potential technological applications. Thus, the aim of this research was to investigate the content of bioactive compounds in its fruits and to assess the color and antioxidant stability of the extracts prepared from such fruits during various thermal treatments and at different pH and ionic strength values. Various spectrophotometric methods, HPLC, and capillary electrophoresis were used to quantify the concentrations of bioactive compounds-polyphenols, carotenoids, organic acids, and to assess antioxidant activity and color. The results show that rowan berries contain circa 1.34-1.47 g/100 g of polyphenols among which include catechin, epicatechin, ferulic acid methyl ester, procyanidin B1, etc.; ca 21.65 mg/100 g of carotenoids including zeaxanthin, ß-cryptoxanthin, all-trans-ß-carotene, and various organic acids such as malic, citric, and succinic, which result in a high antioxidant activity of 5.8 mmol TE/100 g. Results also showed that antioxidant activity exhibited high stability when the extract was subjected to various thermal treatments, pHs, and ionic strengths, while color was mainly impacted negatively when a temperature of 100 °C was employed. This data confirms the technological potential of this traditional, yet often overlooked species.
Subject(s)
Antioxidants/chemistry , Fruit/chemistry , Pigments, Biological/chemistry , Plant Extracts/chemistry , Sorbus/chemistry , Hydrogen-Ion Concentration , Osmolar Concentration , Polyphenols/chemistryABSTRACT
Two novel sulfur-containing dibenzofurans, sorbusins A (1) and B (2), two unprecedented biphenyl glycosides, 2'-hydroxyaucuparin 2'-O-É-L-rhamnoside (3) and noraucuparin 5-O-É-L-rhamnoside (4), and four known analogues (5-8), were isolated from Sorbus pohuashanensis suspension cell induced by yeast extract. Their structures were elucidated based on spectroscopic analyses and quantum calculation of 13C NMR data. Structurally, compound 1 possessed a rare naturally occurring benzothiazole moiety and represents the first example of thiazole fused dibenzofuran. A plausible biosynthetic pathway for the sulfur-containing dibenzofurans is proposed. These dibenzofuran and biphenyl phytoalexins were evaluated for their antimicrobial activities against pathogenic fungi and drug-resistant bacteria. Compound 7 exhibited significant antibacterial activity against methicinllin-resistant Staphylococcus aureus with an MIC value of 3.13 µg/mL.
Subject(s)
Anti-Infective Agents/pharmacology , Dibenzofurans/pharmacology , Glycosides/pharmacology , Sesquiterpenes/pharmacology , Sorbus/chemistry , Anti-Infective Agents/isolation & purification , Dibenzofurans/isolation & purification , Glycosides/isolation & purification , Microbial Sensitivity Tests , Molecular Structure , Phytochemicals/isolation & purification , Phytochemicals/pharmacology , Sesquiterpenes/isolation & purification , PhytoalexinsABSTRACT
Plants have a memory function for the environmental stress they have suffered. When they are subjected to repeated environmental stress, they can quickly and better activate the response and adaptation mechanism to environmental stress, thus realizing long-term stable reproduction. However, most of the relevant studies are applied to crops and Arabidopsis thaliana rather than medicinal plants about the improvement of plant growth status and the effect on phytoalexin biosynthesis. In this study, yeast extract(YE) was used as an elicitor to simulate biotic stress, and the changes in biomass and the content of some secondary metabolites were measured by giving repeated stresses to Sorbus aucuparia suspension cell(SASC). The results showed that the accumulation levels of biomass and some secondary metabolites in SASC subjected to repeated stress are significantly increased at some time points compared with single stress. A phenomenon that SASC can memorize biotic stress is confirmed in this study and influences phytoalexin accumulation in SASC. Furthermore, the work laid the groundwork for research into the transgenerational stress memory mechanism of medicinal plant.
Subject(s)
Sorbus , Cells, Cultured , Secondary Metabolism , Stress, PhysiologicalABSTRACT
Eight natural biphenyl-type phytoalexins exhibiting antifungal effect were isolated from the leaves of Sorbus pohuashanensis, which invaded by Alternaria tenuissi, and their growth inhibition rate towards A. tenuissi were 50.3 %, 54.0 %, 66.4 %, 58.8 %, 48.5 %, 51.0 %, 33.3 %, and 37.0 %, respectively. In vivo activity assay verified the protective effect of these natural biphenyls on tobacco leaves. The observation of mycelial morphology revealed that these compounds possessed adverse effects on mycelial growth of A. tenuissi. Subsequently, the most potent active compounds, 3',4',5'-trimethoxy[1,1'-biphenyl]-4-ol (3) and 3,4,4',5-tetramethoxy-1,1'-biphenyl (4), were conducted to the further antifungal evaluation and showed significant activity against the other four crop pathogens, Fusarium graminearum, Helminthosporium maydis, Sclerotinia sclerotiorum, and Exserohilum turcicum. Further, the structure-activity relationships and biosynthesis of these compounds were speculated in this work.
Subject(s)
Alternaria/drug effects , Antifungal Agents/pharmacology , Biphenyl Compounds/pharmacology , Sorbus/chemistry , Alternaria/growth & development , Alternaria/pathogenicity , Antifungal Agents/chemistry , Antifungal Agents/isolation & purification , Ascomycota/drug effects , Ascomycota/pathogenicity , Biphenyl Compounds/chemistry , Biphenyl Compounds/isolation & purification , Bipolaris/drug effects , Bipolaris/pathogenicity , Fusarium/drug effects , Fusarium/pathogenicity , Microbial Sensitivity Tests , Molecular Structure , Plant Extracts , Plant Leaves/chemistryABSTRACT
The fruits of Sorbus pohuashanensis Hedl. (S. pohuashanensis) are rich in polyphenols with many beneficial effects such as anti-inflammatory, anti-tussive, anti-asthmatic and anti-cancer. In this study, five polyphenols, including three phenolic acids and two flavonoids, were successfully prepared from the fruits of S. pohuashanensis by high-speed counter-current chromatography (HSCCC) using different solvent systems for the first time. Ethyl acetate-n-butanol-water (3.5:1.5:5, v/v) was screened as the two-phase system to separate neochlorogenic acid (1), chlorogenic acid (2), quercetin 3-O-(6â³-α-L-rhamnopyranosyl-4'â³-α-L-rhamnopyranosyl)-ß-D-glucopyranoside (3) and rutin (5). N-hexane-ethyl acetate-methanol-water (1:3:1:3.5, v/v) was first utilized to isolate 3,5-O-dicaffeoylquinic acid (4). The purities of all these compounds were above 95%. In addition, their chemical structures were identified by mass spectrometer (MS), nuclear magnetic resonance (NMR) or the standards. These results indicated that HSCCC was an effective method to separate polyphenols compounds from the fruits of S. pohuashanensis.
Subject(s)
Fruit/chemistry , Plant Extracts/chemistry , Polyphenols , Sorbus/chemistry , Chromatography, High Pressure Liquid , Polyphenols/analysis , Polyphenols/isolation & purificationABSTRACT
Plants have a memory function for the environmental stress they have suffered. When they are subjected to repeated environmental stress, they can quickly and better activate the response and adaptation mechanism to environmental stress, thus realizing long-term stable reproduction. However, most of the relevant studies are applied to crops and Arabidopsis thaliana rather than medicinal plants about the improvement of plant growth status and the effect on phytoalexin biosynthesis. In this study, yeast extract(YE) was used as an elicitor to simulate biotic stress, and the changes in biomass and the content of some secondary metabolites were measured by giving repeated stresses to Sorbus aucuparia suspension cell(SASC). The results showed that the accumulation levels of biomass and some secondary metabolites in SASC subjected to repeated stress are significantly increased at some time points compared with single stress. A phenomenon that SASC can memorize biotic stress is confirmed in this study and influences phytoalexin accumulation in SASC. Furthermore, the work laid the groundwork for research into the transgenerational stress memory mechanism of medicinal plant.