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phenolic acids isolated from the fungus Schizophyllum commune exert analgesic activity by inhibiting voltage-gated sodium channels

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Chinese Journal of Natural Medicines 2016年第9期14卷 661-670页

作者： YAO Hui-Min WANG Gan LIU Ya-Ping RONG Ming-Qiang SHEN Chuan-Bin YAN Xiu-Wen LUO Xiao-Dong LAI Ren College of Life Sciences Nanjing Agricultural University Nanjing 210095 China Key Laboratory of Animal Models and Human Disease Mechanisms of Chinese Academy of Sciences & Yunnan Province Kunming Institute of Zoology Kunming 650223 China State Key Laboratory of Phytochemistry and Plant Resources in West China Kunming Institute of Botany Chinese Academy of Sciences Kunming 650204 China

The present study was designed to search for compounds with analgesic activity from the Schizophyllum commune(SC), which is widely consumed as edible and medicinal mushroom world. Thin layer chromatography(TLC), tosilica gel column chromatography, sephadex LH 20, and reverse-phase high performance liquid chromatography(RP-HPLC) were used to isolate and purify compounds from SC. Structural analysis of the isolated compounds was based on nuclear magnetic resonance(NMR). The effects of these compounds on voltage-gated sodium(NaV) channels were evaluated using patch clamp. The analgesic activity of these compounds was tested in two types of mouse pain models induced by noxious chemicals. Five phenolic acids identified from SC extracts in the present study included vanillic acid, m-hydroxybenzoic acid, o-hydroxybenzeneacetic acid, 3-hydroxy-5-methybenzoic acid, and p-hydroxybenzoic acid. They inhibited the activity of both tetrodotoxin-resistant(TTX-r) and tetrodotoxin-sensitive(TTX-s) NaV channels. All the compounds showed low selectivity on NaV channel subtypes. After intraperitoneal injection, three compounds of these compounds exerted analgesic activity in mice. In conclusion, phenolic acids identified in SC demonstrated analgesic activity, facilitating the mechanistic studies of SC in the treatment of neurasthenia.

关键词： Schizophyllum commune Sodium channel phenolic acids Pain

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Distribution of antioxidants and phenolic compounds in flour milling fractions from hard red winter wheat

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Grain & Oil Science and Technology 2024年第2期7卷 71-78页

作者： Lauren Renee Brewer Jittawan Kubola Sirithon Siriamornpun Yong-Cheng Shi Department of Grain Science and Industry Kansas State UniversityManhattanKS 66506USA Department of Food Innovation and Processing Faculty of Agricultural TechnologyBuriram Rajabhat UniversityBuriram 31000Thailand Research Unit of Thai Food innovation Department of Food Technology and NutritionMahasarakham UniversityMahasarakham 44000Thailand

Mature wheat kernels contain three main parts:endosperm,bran,and germ.Flour milling results in multiple streams that are chemically different;however,the distribution of antioxidants and phenolic compounds has not been well documented in terms of conventional milling by-product streams.In this study,multiple analytical methods were used to investigate antioxidant activity and phenolic compound compositions of hard red winter wheat(whole ground wheat),the parts of a wheat kernel(bran,flour,germ),and wheat by-product streams(mill feed,red dog,shorts)for the first time.For each mill stream,phenolic compounds(total,flavonoid,and anthocyanin contents)were determined and antioxidant activities were evaluated with 1,1-diphenyl-2-picrylhydrazyl(DPPH)radical-scavenging activity,ferric reducing/antioxidant power(FRAP),and total antioxidant capacity assays.Significant differences(Pphenolic concentrations among fractions of bran,flour,and germ milled from the same kernels and noted that germ accounts for the majority of antioxidant properties,whereas bran contains a substantial portion of phenolic compounds and anthocyanins.Mill feed was high in phenolic content(5.29 mg FAE/g),total antioxidant capacity(866 mg/g),and antioxidant activity(up to 75% DPPH inhibition and 20.26μmol FeSO_(4)/g).The comprehensive information on distribution of antioxidants and phenolic compounds provides insights for future human consumption of commonly produced co-products from flour milling,and for selecting and using different milling fractions to make foods with improved nutritional properties.

关键词： Wheat Milling streams Antioxidants phenolic acids Flavonoid Anthocyanin

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Simultaneous detection of seven phenolic acids in Danshen injection using HPLC with ultraviolet detector

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Journal of Zhejiang University-Science B(Biomedicine & Biotechnology) 2008年第9期9卷 728-733页

作者： Jin-zhong XU, Jie SHEN, Yi-yu CHENG, Hai-bin QU (Department of Chinese Medicine Science and Engineering, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, China) Department of Chinese Medicine Science and Engineering College of Pharmaceutical Sciences Zhejiang University Hangzhou 310058 China.

A high-performance liquid chromatographic (HPLC) method with ultraviolet (UV) detector had been developed for simultaneous quantification of danshensu, protocatechuic aldehyde, caffeic acid, salvianolic acid D, rosmarinic acid, salvianolic acid B and salvianolic acid A in Danshen injection. According to the UV spectra of these components, three detection wavelengths have been selected as follows: 280 nm for danshensu and protocatechuic aldehyde, 326 nm for caffeic acid, salvianolic acid D and rosmarinic acid, 286 nm for salvianolic acid B and salvianolic acid A. The limit of detection (LOD) was improved to be in the range of 0.008~0.160 μg/ml. Moreover, excellent linear behavior over the investigated concentration range was observed, with R>0.999 for all the analytes.

关键词： High-performance liquid chromatography (HPLC) Danshen injection (DSI) phenolic acids Multi-wavelengths Quantification

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phenolic acids Content and Nutritional Quality of Conventional, Organic and Biodynamic Cultivations of the Tomato CXD271BIO Breeding Line (Solanum lycopersicum L.)

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Food and Nutrition Sciences 2016年第12期7卷 1112-1121页

作者： Laura D’Evoli Massimo Lucarini Josè Sánchez del Pulgar Altero Aguzzi Paolo Gabrielli Loretta Gambelli Ginevra Lombardi-Boccia CREA—Food and Nutrition Rome Italy

This study was undertaken to evaluate the influence of growing systems (conventional, organic and biodynamic performed with two types of manuring) on some nutritional traits of the tomato breeding line CXD271BIO (Solanum lycopersicum L.). Experimental fields were in the same geographical area and the cultivations were performed over five years. The content of macronutrients, minerals (Ca, K, Mg, P, Na), trace elements (Fe, Zn, Cu, Mn) and phenolic acids (chlorogenic, caffeic, p-coumaric and ferulic acids) was determined. The biodynamic A growing system showed the highest protein and carbohydrates content compared to the other growing systems. Data on minerals and trace elements content showed significant differences (mainly in Ca, Na, Fe and Zn content) between conventional and biodynamic tomatoes, whereas no major impact of the fertilization among organic and the two biodynamic growing systems was observed. Appreciable differences in phenolic acids biosynthesis were observed, with the year of harvest showing a marked effect especially on chlorogenic, p-cumaric and ferulic acids content. Conversely, the cultivation system did not show major influence. Principal Components Analysis (PCA), performed on mineral and phenolic acids content, substantiated the large effect of the year of harvest, also suggesting an effect of the conventional cultivation system.

关键词： Tomato Conventional Organic Biodynamic phenolic acids Minerals Trace Elements

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Use of Ultrasound Bath in the Extraction and Quantification of Ester-Linked phenolic acids in Tropical Forages

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American Journal of Analytical Chemistry 2011年第3期2卷 344-351页

作者： Mellina Damasceno Rachid Santos Aline de Paula Vitor Jailton da Costa Carneiro Domingos Savio Campos Paciullo Renato Camargo Matos Maria Auxiliadora Costa Matos NUPIS(Nucleo de Pesquisa em Instrumentacao e Separacao Analiticas) Departamento de QuimicaInstituto de Ciencias ExatasUniversidade Federal de Juiz de ForaJuiz de ForaBrazil EMBRAPA—Centro Nacional de Pesquisa de Gado de Leite(CNPGL) Juiz de ForaBrazil

A method was developed for the analysis of ester-linked phenolic acids in forage samples using extraction by an ultrasound-assisted treatment and quantification by HPLC with a UV-VIS detector. A reversed-phase C18 column was used for developing the method and the optimal condition was established with isocratic elution using acetonitrile/methanol/H3PO4 pH 2.08 (13:12.5:74.5) as the mobile phase. To reduce the time of sample processing, the extraction of ester-linked phenolic acids was studied using ultrasound bath and the results were then compared with those from an extraction usual using alkaline hydrolysis (20°C for 24 h). The method was valued through external and internal calibration. Internal calibration using o-coumaric acid as internal standard and m-coumaric acid as surrogate internal standard showed better results. The detection limits were of 0.09 and 0.04 mg●L-1 for p-coumaric and ferulic acids, respectively. The proposed method showed a good linear dynamic range (3.00 - 30.00 mg●L-1) for the analytes. The usefulness of the methodology was demonstrated by addition-recovery experiments using forage samples and values were in the 83 to 99% range. The extraction of ester-linked phenolic acids by 120 minutes of ultrasound bath was faster and more reproducible than alkaline hydrolysis (20°C for 24 h).

关键词： Ultrasound Bath phenolic acids Forage Internal Calibration

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Temperature and Acidified Solvent Effect on Total Anthocyanins and RP-HPLC phenolic acids Determination in Selected Spices

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Food and Nutrition Sciences 2016年第1期7卷 20-29页

作者： Sufyan H. Tashtoush Khalil I. Ereifej Hao Feng Taha M. Rababah Muhammad H. Al-U’datt Sana Gammoh Ghaid J. Al-Rabadi Department of Nutrition and Food Technology Faculty of Agriculture Jordan University of Science and Technology Irbid Jordan Department of Food Science and Human Nutrition University of Illinois Urbana-Champaign USA Department of Animal Production Faculty of Agriculture Mutah University Al-Karak Jordan

Total anthocyanins of spices (Syzygium aromaticum L., Coriadrum sativum L., Cuminum cyminum L., Zingiber officinale Rosc., Elettaria cardamomum, Curcuma longa, Rhus coriaria L., Cinnamomum zeylanicum Blume, Foeniculum vulgare Mill and Laurus nobilis L.) were determined using acidified (1% HCl) solvents (methanol, ethanol and acetone) at three temperatures (20℃, 40℃ and 60℃). Also phenolic acids were separated and identified by RP-HPLC. Results showed that sumac and cinnamon had the highest levels of anthocyanins, while for the acetone the cinnamon indicated the highest amount of anthocyanins when methanol and ethanol were used as extracting solvents at 20℃. At 40℃ using ethanol, sumac showed the highest level of anthocyanins whereas acetone solvent yielded the highest anthocyanin contents for cinnamon. At 60℃, cinnamon showed the highest level of anthocyanins when methanol and acetone were the solvents, while sumac had the highest anthocyanins level using ethanol as solvent. HPLC results showed ten phenolic acids found in those spices and varied in their concentrations. Gallic acid had the highest level (1642.3 mg/100g) (cloves). Gentisic acid had the lowest level (1.2 mg/100g) in ginger. Also sumac showed the highest level of chlorogenic acid (1528.7 mg/100g). Some acids were not found in some spices, for instance, benzoic acid was not found in coriander, cumin, ginger, green cardamom, cinnamon and sweet laurel.

关键词： Spices Anthocyanins phenolic acids HPLC and Acidified Solvents

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Effects of phenolic acids on Growth and Activities of Membrane Protective Enzymes of Cucumber Seedlings

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Agricultural Sciences in China 2002年第8期1卷 900-904页

作者： WU Feng-zhi , HUANG Cai-hong and ZHAO Feng-yan(College of Horticulture, Northeast Agricultural University, Harbin 150030, P.R.China) College of Horticulture Northeast Agricultural University Harbin 150030 P.R. China

Two phenolic acids P-hydroxy benzoic acid and cinnamic acid were designated as four concentrations (0, 50 μmol/L, 100 μmol/L, 150 μmol/L) to investigate the effects of phenoic acids on the growth and the activities of membrane protective enzymes of cucumber seedlings. The results showed that both phenolic acids inhibited the seedlings growth. The inhibitory effects were increased with the concentration of phenolic acids increasing and the time of treatment prolonging. Seedlings treated with A150 (P-hydroxy benzoic acid, 150 μmol/L), B50 (cinnamic acid, 50 μmol/L), B100 (cinnamic acid, 100 μmol/L), B150 (cinnamic acid, 150 μmol/L) showed significantly shorter in plant height , smaller in leaf area. and lighter in fresh weight. The inhibitory effect of cinnamic acid was comparatively stronger than that of P-hydroxy benzoic acid. For protective enzymes system, compared to control , the POD activity increased at all concentrations of P-hydroxy benzoic acid during the treatment but increased at first then decreased before increased again at last at all concentrations of cinnamic acid .In the case of CAT, its activity increased at first, then decreased, and increased again at lower concentrations of phenolic acids. However, at higher concentrations the activities decreased at first, then increased a little, decreased continuously at last. In addition, the treatments of phenolic acids led to an increase then a decreaseof SOD activity and an increase of MDA content in the seedlings. All above indicated the accumulating of free radicalsand destruction of protective enzymes at higher concentrations of phenolic acids.

关键词： Cucumber phenolic acids Protective enzymes activities

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Guanxinning tablet inhibits the interaction between leukocyte integrin Mac-1 and platelet GPIbαfor antithrombosis without increased bleeding risk

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Chinese Journal of Natural Medicines 2022年第8期20卷 589-600页

作者： YANG Qin-Qin FANG Ming-Sun TU Jue MA Quan-Xin SHEN Li-Ye XU Yan-Yun CHEN Jie CHEN Min-Li Academy of Chinese Medicine&Institute of Comparative Medicine Zhejiang Chinese Medical UniversityHangzhou 310053China Department of Experimental Animals Zhejiang Academy of Traditional Chinese MedicineHangzhou 310007China Department of Vasculocardiology the First Affiliated Hospital of Zhejiang Chinese Medicine UniversityHangzhou 310006China

Recent studies have showed that thrombosis is closely related to leucocytes involved in immunity.Interfering with the binding of leukocyte integrin Mac-1 and platelet GPIbαcan inhibit thrombosis without affecting physiological coagulation.Mac-1-GPIbαis proposed as a potential safety target for antithrombotic agents.Guanxinning tablet(GXNT)is an oral Chinese patent medicine used for the treatment of angina pectoris,which contains phenolic acid active ingredients,such as salvianolic acids,ferulic acid,chlorogenic acid,caffeic acid,rosmarinic acid,tanshinol,and protocatechualdehyde.Our previous studies demonstrated that GXN exhibited significant antithrombotic effects,and clinical studies suggested that it did not increase bleeding risk.In addition,GXN exerted a significantly regulatory effect on immune inflammation.In the current study,we intended to evaluate the effects of GXN on bleeding events and explore the safety antithrombotic mechanism of GXN based on leukocyte-platelet interaction.First,we established a gastric ulcer model induced by acetic acid in rats and found that GXN not only did not increase the degree of gastrointestinal bleeding when gastric ulcer occurred,but also had a certain promoting effect on the healing of gastric ulcer.Second,in vitroexperiments showed that after pretreatment with GXN and activation by phorbol 12-myristate-13-acetate(PMA),the adhesion and aggregation of leukocytes with human platelets were reduced.It was also found that GXN reduced the expression and activation of Mac-1 in leucocytes,and inhibited platelet activation due to leukocyte engagement via Mac-1.Overall,the results suggest that GXN may be a safe antithrombotic agent,and its low bleeding risk mechanism is probably related to inhibited leukocyte-platelet aggregation and its interaction target Mac-1-GPIbα.

关键词： Thrombosis Guanxinning tablet phenolic acids Integrin Mac-1 Glycoprotein Ibα

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Liquid laccase production by Phomopsis liquidambari B3accelerated phenolic acids degradation in long-term cropping soil of peanut

Liquid laccase production by Phomopsis liquidambari B3accele...

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2014年第七届中国模式真菌研讨会

作者：周俊 Li Kang Hong-Wei Wang Teng Yang Chuan-Chao Dai Jiangsu Engineering and Technology Research Center for Industrialization of Microbial Resources Jiangsu Key Laboratory for Microbes and Functional GenomicsCollege of Life SciencesNanjing Normal University

Food waste and wheat straw are waste products that pollute the environment.But if we make full use of them,they will be the resources which improve laccase production by the endophytic fungus Phomopsis liquidambari B3.We cultured P.liquidambari B3 in medium containing food waste and wheat straw as the main nitrogen and carbon sources,respectively.The fermentation products with high laccase activity were put into the continuously cropped soil of peanut.The results show that laccase significantly(pphenolic acids in soil compare with other treatments.Analysis of denaturing gradient gel electrophoresis(DGGE) profiles show that bacterial and fungal community structure of rhizosphere soil were significantly affected by changes in phenolic acids concentration.The decrease of phenolic acids and increase in dominant microorganisms resulted in the promotion of peanut seeding growth and nodulation.This technology provides a new idea for bioremediation of the continuous cropping soil,and helps to realize waste disposal and environment protection.

关键词： Food waste Wheat straw Phomopsis liquidambari B3 Laccase phenolic acids Continuous cropping obstacle

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Changes in the root system of the herbaceous peony and soil properties under different years of continuous planting and replanting

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Horticultural Plant Journal 2023年第4期9卷 801-810页

作者： Anqi Xie Limin Sun Dongliang Zhang Yang Li Zemiao Liu Xue Li Xia Sun College of Horticulture State Key Laboratory of Crop BiologyShandong Agricultural UniversityTai'anShandong 271018China College of Forestry Shandong Agricultural UniversityTai'anShandong 271018China

The herbaceous peony(Paeonia lactiflora Pall.)has high ornamental value.Replanting problems occur when seedlings are replanted into previous holes.We studied the root system and soil environment of the'Dongjingnvlang'variety under a continuous planting regime of one,four,and seven years,and a replanting regime of one and four years.Under the condition of continuous planting,with the increase of number of years,pH,ammonium nitrogen,and nitrate nitrogen decreased in the rhizosphere and non-rhizosphere soils,whereas organic matter,available phosphorus and potassium,enzyme activities,and the number of bacteria,fungi,and actinomycetes increased.Under the condition of replanting,with the increase of number of years,fungi and actinomycetes in both soils increased,while pH,organic matter,nutrients,enzyme activities,and bacterial number decreased.pH,organic matter,nutrient content,enzyme activity and the number of bacterial were lower in soil replanted for four years,whereas the abundance of fungi and actinomycetes was higher,altering the soil from“bacterial high-fertility”to“fungal low-fertility”with increasing years of replanting.The activity of antioxidant enzymes and MDA content in roots of peony in replanting were higher than those in continuous planting,while the content of osmotic regulatory substances in replanting was lower than that in continuous planting.The results showed that there were no obvious adverse factors in soil during seven years of continuous planting,and herbaceous peony could maintain normal growth and development.However,soils after four years of replanting were not suitable for herbaceous peony growth.Benzoic acid increased with years of replanting,which potentially caused replanting problems.This study provides a theoretical basis for understanding the mechanism of replanting problems in the herbaceous peony.

关键词： Herbaceous peony Replanting problems Continuous planting Soil environment phenolic acids Paeoniflorin

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