Phenolic constituents of Sanguisorba officinalis and their Nrf2 agonistic effect / 药学学报

Thirty-one phenolic constituents were isolated and purified from the 95% ethanol extract of Sanguisorbae Radix by using various chromatographic techniques, including macroporous resin, silica gel, ODS, Sephadex LH-20 and semi-preparative HPLC. Their structures were elucidated by physicochemical properties, spectroscopic data (MS and NMR) and electronic circular dichroism (ECD) spectra, and identified as 3-methoxyl-2S,3S-epoxyflavanone (1a), 3-methoxyl-2R,3R-epoxyflavanone (1b), longifoin B (2), longifoin C (3), eriodictyol (4), naringenin (5), liquiritigenin (6), 5,3ʹ-dihydroxy-7,4ʹ-dimethoxyflavanone (7), naringenin-7-O-β-D-glucopyranoside (8), dihydroquercetin (9), dihydrokaempferol (10), (-)-garbanzol (11), (2R,3R)-4-methoxyl-distylin (12), kaempferol (13), quercetin (14), α,4,2′,4′-tetrahydroxydihydrochalcone (15), phloretin (16), (+)-catechin (17), ethyl (+)-cyanidan-3-ol-8-carboxylate (18), phyllocoumarin (19), methyl 3-methoxy-4,5-dihydroxybenzoate (20), 4,5-dimethoxy-3-hydroxybenzoic acid methyl ester (21), 3,4′-di-O-methylellagic acid (22), 3,4,3′-O-trimethylellagic acid (23), 3,3ʹ,4ʹ-O-trimethylellagic acid-4-O-β-D-xyloside (24), (3R)-thunberginol C (25), resveratrol (26), 1-hydroxypinoresinol (27), (7S,8S)-3-methoxy-3′,7-epoxy-8,4′-oxyneoligna-4,9,9′-triol (28), emodin-8-O-β-D-glucoside (29), phloracetophenone (30) and 4-(4′-hydroxyphenyl)-butan-2-one (31). Among them, compound 1a and 1b is a pair of new flavonoid enantiomers, compounds 2 and 3 are a pair of new epimers, while compounds 4, 5, 6, 9, 10, 13, 16 and 26 were obtained from S. officinalis for the first time, compounds 7, 8, 27, 30 and 31 were isolated for the first time from the S. officinalis genus, and compounds 11, 12, 15, 18, 19, 25, 28 and 29 were isolated for the first time from the Rosaceae. The antioxidant activities of compounds 1-24 were evaluated by activating the Nrf2 transcriptional pathway, which were measured by the dual-luciferase reporter gene assay in 293T cells. Compounds 4, 6-10, 12, 14, 17, 19, 20 and 22-24 showed significant Nrf2 agonistic effect compared with the control group at 25 μmol·L-1, which provided reference for the research of their antioxidant activity.

Phytochemical screening and evaluation of antioxidant, total phenolic and flavonoid contents in various weed plants associated with wheat crops

Abstract This study explores the antioxidant activity, phytochemical screening, total phenolic and flavonoids contents in the extracts of four locally available weeds plants namely Convolvulus arvensis, Chenopodium murale, Avena fatua and Phalaris minor with different solvents. The antioxidant activities of these extracts were determined via various in-vitro methods such as total antioxidant activity (TAA), reducing power (RP), DPPH (2,2-Diphenyl-1-Picrylhydrazyl) free radical scavenging and hydrogen peroxide scavenging assays. Phytochemical screening was performed both qualitatively as well as quantitatively. Total phenolic content (TPC) and total flavonoid content (TFC) were determined through Folin- Ciocalteu reagent and aluminium chloride methods respectively. Methanol-chloroform solvent showed the presence of a high amount of TPC in milligram of gallic acid equivalent per gram of dry weight (mg of GAE/g of DW) in the extracts of all weeds. Their descending sequence was Avena fatua (74.09) Phalaris minor (65.66) Chenopodium murale (64.04) Convolvulus arvensis (61.905), while, chloroform solvent found to be best solvent for the extraction of TFC. Methanol-chloroform solvent was also found to be best solvent for TAA (Total antioxidant activity assay) which showed values in milligram of ascorbic acid equivalent per gram of dry weight (mg of AAE /g of DW), for DPPH scavenging activity, reducing power (antioxidant activity) and hydrogen peroxide scavenging activity. Phytochemical screening indicated the presence of polyphenols, flavonoids, tannins, saponins, alkaloids and glycosides in these weeds.

Resumo Este estudo investiga a atividade antioxidante, a triagem fitoquímica, os teores de fenólicos totais e de flavonoides nos extratos de quatro plantas daninhas disponíveis localmente, quais sejam, Convolvulus arvensis, Chenopodium murale, Avena fatua e Phalaris minor com diferentes solventes. As atividades antioxidantes desses extratos foram determinadas por meio de vários métodos in vitro, tais como atividade antioxidante total (TAA), poder redutor (RP), sequestro de radicais livres DPPH (2,2-Difenil-1-Picril-hidrazil) e ensaios de sequestro de peróxido de hidrogênio. A triagem fitoquímica foi realizada tanto qualitativamente quanto quantitativamente. O teor de fenólicos totais (TPC) e o teor de flavonoides totais (TFC) foram determinados pelos métodos do reagente de Folin-Ciocalteu e do cloreto de alumínio, respectivamente. O solvente metanol-clorofórmio mostrou a presença de elevada quantidade de TPC em miligramas de ácido gálico equivalente por grama de peso seco (mg de GAE/g de DW) nos extratos de todas as plantas daninhas. Sua sequência descendente foi Avena fatua (74,09) Phalaris minor (65,66) Chenopodium murale (64,04) Convolvulus arvensis (61,905), enquanto o solvente clorofórmio foi o melhor solvente para a extração de TFC. O solvente metanol-clorofórmio também foi considerado o melhor solvente para AAT (ensaio de atividade antioxidante total), que apresentou valores em miligramas de equivalente de ácido ascórbico por grama de peso seco (mg de AAE/g de DW), para atividade sequestrante de DPPH, RP (atividade antioxidante) e atividade de sequestro de peróxido de hidrogênio. A triagem fitoquímica indicou a presença de polifenóis, flavonoides, taninos, saponinas, alcaloides e glicosídeos nessas plantas daninhas.

Uso potencial de residuos agroindustriales como fuente de compuestos fenólicos con actividad biológica

Los compuestos fenólicos poseen propiedades bioactivas de interés en la Medicina. Investigaciones actuales se enfocan en la búsqueda de nuevas fuentes de este tipo de compuestos. Varios estudios se han propuesto recuperar, caracterizar e identificar compuestos fenólicos a partir de residuos agroindustriales buscando en ellos diversas actividades biológicas. La presente investigación se desarrolló con el objetivo de describir el uso potencial de residuos agroindustriales como una fuente de compuestos fenólicos con actividad biológica y su uso en la Medicina. Los residuos agroindustriales poseen un elevado potencial como novedosa fuente de compuestos fenólicos con actividad biológica, empleables en la farmacéutica, industria alimentaria y cosmética. Entre sus aplicaciones se encuentran las de antioxidante, antiinflamatorio, antimicrobiano y la actividad antiproliferativa. Varios de los residuos agroindustriales provienen de productos cultivables en Ecuador, de ahí que constituya una oportunidad a explotar en la industria nacional. Los estudios en Ecuador sobre el aprovechamiento de residuos agroindustriales se enfocan en la obtención de biocombustibles, bioplásticos y productos de alimentación animal, por lo que la búsqueda de compuestos bioactivos a partir de nuevas fuentes aún es un campo incipiente.

Phenolic compounds have bioactive properties of interest in Medicine. Current research focuses on the search for new sources of this type of compounds. Several studies have proposed recovering, characterizing and identifying phenolic compounds from agroindustrial waste, searching for various biological activities in them. The present research was developed with the objective of describing the potential use of agroindustrial waste as a source of phenolic compounds with biological activity and their use in Medicine. Agroindustrial waste has a high potential as a novel source of phenolic compounds with biological activity, which can be used in the pharmaceutical, food and cosmetic industries. Among its applications are antioxidant, anti-inflammatory, antimicrobial and antiproliferative activity. Several of the agroindustrial waste come from cultivable products in Ecuador, hence it constitutes an opportunity to be exploited in the national industry. Studies in Ecuador on the use of agroindustrial waste focus on obtaining biofuels, bioplastics and animal feed products, so the search for bioactive compounds from new sources is still an incipient field.

The effect of extraction methods on total phenolics and antioxidant activities in Caulerpa racemosa (Forsskal) J. Agardh extracts / Efecto de los métodos de extracción sobre los fenoles totales y las actividades antioxidantes de los extractos de Caulerpa racemosa (Forsskal) J. Agardh

Background: The edible green algae Caulerpa racemosa (Forsskal) J. Agardh (Caulerpaceae), also known as "sea grape", is an excellent source of phenolic compounds known for their activity to reduce free radicals. Objectives: The research aims to evaluate the total phenolic content and antioxidant activity of C. racemosa (70% ethanol extracts) obtained from different extraction methods, such as maceration, Soxhlet, and ultrasound. Methods: Total phenolics of the extracts were determined by the colorimetry method using the Folin-Ciocalteu reagent. Total phenol content was expressed as mg gallic acid equivalent (GAE) per g extract. The 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical was used to assess the antioxidant activity of the extracts. Results: the ethanol extract of C. racemosa obtained from the ultrasonic methods had the highest phenolic content (39.38 mg GAE/g) compared to other extraction methods (Soxhlet was 36.88 mg GAE/g and maceration was 22.05 mg GAE/g). The IC50 value against DPPH of the C. racemosa ethanol extracts using ultrasonic, Soxhlet, and maceration was 352.95, 365.73, and 375.84 µg/mL, respectively. Conclusions: the variation of the extraction methods affected the total phenolics content of C. racemosa ethanol extracts and their antioxidant activity. We reported here the potential of C. racemosa extracts as an antioxidant raw material from marine plants for medicinal, nutraceutical, cosmetics, and food products; however, more research is needed.

Antecedentes: El alga verde comestible Caulerpa racemosa (Forsskal) J. Agardh (Caulerpaceae), también conocida como "uva de mar", es una excelente fuente de compuestos fenólicos conocidos por su actividad para reducir los radicales libres. Objetivos: La investigación pretende evaluar el contenido fenólico total y la actividad antioxidante de C. racemosa (extractos de etanol al 70%) obtenidos a partir de diferentes métodos de extracción, como maceración, Soxhlet y ultrasonido. Métodos: Los fenoles totales de los extractos se determinaron por el método colorimétrico utilizando el reactivo de Folin-Ciocalteu. El contenido total de fenoles se expresó como mg de ácido gálico equivalente (GAE) por g de extracto. Para evaluar la actividad antioxidante de los extractos se utilizó el radical libre 2,2-difenil-1-picrilhidrazilo (DPPH). Resultados: el extracto etanólico de C. racemosa obtenido por ultrasonido presentó el mayor contenido fenólico (39,38 mg GAE/g) en comparación con otros métodos de extracción (Soxhlet fue de 36,88 mg GAE/g y maceración fue de 22,05 mg GAE/g). El valor IC50 frente a DPPH de los extractos etanólicos de C. racemosa mediante ultrasonido, Soxhlet y maceración fue de 352,95, 365,73 y 375,84 µg/mL, respectivamente. Conclusiones: la variación de los métodos de extracción afectó al contenido total de fenoles de los extractos etanólicos de C. racemosa y a su actividad antioxidante. Aquí reportamos el potencial de los extractos de C. racemosa como materia prima antioxidante a partir de plantas marinas para productos medicinales, nutracéuticos, cosméticos y alimenticios; sin embargo, se necesita más investigación.

Chemical and Biological Evaluation of Bakeries Produced from Golden Berries

This investigation was performed with the purpose of researching the influence of pizza containing dried golden berry fruits (DGBF) at different doses against carbon tetrachloride - induced hepatotoxicity in rats. The study shows phenols content of golden berry. 25 male rats were used in the biological investigation. Rats were divided into five groups (5 rats in group) the investigation was 12 weeks. The first group (negative group) was given a basal diet and the second group (G2, G3, G4, and G5) was injected intramuscularly with carbon tetrachloride 2 ml/kg BW (50% v/v in liquid paraffin) weekly to induce hepatotoxicity. After the injury, group G3, G4 and G5 fed on 50% basal diet supplemented with 50%pizza containing 5, 10 and 15% DGBF. Findings indicate that DGBF had a high antioxidant activity, total phenol, flavonoids, ascorbic acid and carotenoids content. Rats fed 50% pizza containing (5,10 and 15%) DGBF had a lower serum total cholesterol, LDL cholesterol, triglyceride, urea, uric acid, creatinine, GOT, GPT, MDA and SOD compared to rats fed simply the basal diet (positive control). The DGBF was added to the pizza with different proportions, and its sensory properties were evaluated, and all proportions were proper to the panelists, compared to the control. The findings of this work suggest that golden berries could be used to treat and prevent hepatotoxicity patients.

Total phenolic, monomeric anthocyanin content and antioxidant activity of Berberis commutata Eichler fruits / Contenido fenólico total, antocianinas monoméricas y actividad antioxidante de los frutos de Berberis commutata Eichler

Background: Berberis commutata Eichler is a berry that grows in the Peruvian Andes and has been consumed in the Andes of South America since ancient times. The edible fruits have an intense purple color and are rich in anthocyanins and phenolic compounds that are available from February until May each year. The color of the fruits is a soft purple dye for natural fibers, and many birds use them as food. Objective: This study quantified the total phenolic, monomeric anthocyanin content and antioxidant activity of Berberis commutata Eichler berries. Methods: The total phenolic content was determined by the Folin-Ciocalteu colorimetric assay. Monomeric anthocyanin content was determined by the method is pH differential, and the antioxidant activity was measured using the Brand-Williams method. Results: The total phenolic content was 7,490 ± 0.85 mg GAE/100g, and the monomeric anthocyanin content was 70 ± 0.03 mg/100g. The antioxidant activity of the berries showed a tendency to increase with B. commutata extract concentration; an EC50 of 0.91 mg/mL was calculated, indicating a high antioxidant power. Conclusion: Our results showed that B. commutata E. has both high total phenolic content and monomeric anthocyanins comparable to other superfruits and high antioxidant activity, which means that it is possible to use this berberis species as a functional food.

Introducción: Berberis commutata Eichleres una baya que crece en los Andes peruanos. Los frutos comestibles tienen un intenso color púrpura rico en antocianinas y componentes fenólicos que están disponibles desde febrero hasta mayo de cada año. El color de sus frutos se utiliza como un suave colorante púrpura para las fibras naturales y muchas aves los utilizan como alimento. Sin embargo, desde la antigüedad los frutos de esta especie han sido consumidas en los Andes de Sudamérica. Objetivo: Este estudio cuantificó el contenido fenólico total, antocianinas monoméricas y la actividad antioxidante usando el método del radical DPPH de las bayas de Berberis commutata Eichler. Método: El contenido fenólico total se midió a través del ensayo colorimétrico de Folin-Ciocalteu, el contenido de antocianinas monoméricas se determinó mediante el método del pH diferencial y la actividad antioxidante se midió con el método de Brand-Williams. Resultados: El contenido fenólico total fue de 7,490 ± 0.85 mg GAE/100g y el contenido de antocianinas monoméricas fue de 70 ± 0.03 mg/100g. La actividad antioxidante de las bayas mostró una tendencia a aumentar con la concentración del extracto de B. commutata, se calculó un EC50 de 0.91 mg/mL que indica un alto poder antioxidante. Conclusión: Nuestros resultados mostraron que B. commutata E. tiene tanto un alto contenido fenólico total, así como antocianinas monoméricas comparables con otras superfrutas y una elevada actividad antioxidante, lo que significa que es posible utilizar esta especie de berberis como alimento funcional.

Study of total antioxidant capacity of red raspberry (Rubus idaeous L. ) shoots. / Estudio de la capacidad antioxidante total de brotes de frambuesa roja (Rubus idaeous L. ).

Background: Today, cardiovascular, oncological, and neurodegenerative diseases are the main causes of death in the world, according to official World Health Organization (WHO) statistics. Antioxidants are used to treat and prevent these diseases. In order to develop optimal technology for obtaining drugs based on plant extracts with antioxidant action, it is necessary to determine the total antioxidant capacity of raspberry shoots. Objectives: The study aimed to determine the total antioxidant capacity of red raspberry shoots, study the content of biologically active substances (BAS), and the antioxidant activity of red raspberry shoot extracts obtained during subsequent exhaustive extraction. Methods: The number of phenolic compounds, catechins, flavonoids, and hydroxycinnamic acids was determined by a spectrophotometric analysis method, whereas organic acids were determined by the alkalimetric method in red raspberry shoot extracts; the antioxidant activity of obtained extracts was evaluated by potentiometric method. Results: The total antioxidant capacity of red raspberry shoots was 164.12 mmol-equiv./m dry weight, the sum of the total content of phenolic compounds was 24.40 mg gallic acid (GA)/mL, catechins ­ 21.36 mg epigallocatechin-3-O-gallate (EGCG)/mL, flavonoids ­ 0.77 mg rutin (R)/mL, hydroxycinnamic acids derivatives ­ 2.56 mg chlorogenic acid (ChA)/mL and organic acids ­ 1.88 mg citric acid (CA)/mL in red raspberry shoot extracts obtained during subsequent exhaustive extraction. The analysis showed that there is a very high positive correlation between antioxidant activity and total phenolic compounds, catechin, flavonoid, hydroxycinnamic acids derivatives, and organic acids content in red raspberry shoot extracts. Conclusions: Total red raspberry shoots' antioxidant capacity has been determined. The study results can be used to develop optimal technology for obtaining drugs based on the extract of red raspberry shoots, which has an antioxidant effect

Contexto: Hoy en día, las enfermedades cardiovasculares, oncológicas y neurodegenerativas son las principales causas de muerte en el mundo según estadísticas oficiales de la Organización Mundial de la Salud OMS. Los antioxidantes se utilizan para tratar y prevenir estas enfermedades. Para desarrollar una tecnología óptima para la obtención de fármacos a base de extractos de plantas con acción antioxidante, es necesario determinar la capacidad antioxidante total de los brotes de frambuesa.Objetivos: El estudio tuvo como objetivo determinar la capacidad antioxidante total de los brotes de frambuesa roja, estudiar el contenido de sustancias biológicamente activas (SBA) y la actividad antioxidante de los extractos de brotes de frambuesa roja obtenidos mediante extracción exhaustiva. Métodos: La cantidad de compuestos fenólicos, catequinas, flavonoides y ácidos hidroxicinámicos se determinó por método de análisis espectrofotométrico, mientras que los ácidos orgánicos por método alcalimétrico en extractos de brotes de frambuesa roja; La actividad antioxidante de los extractos obtenidos se evaluó por método potenciométrico. Resultados: La capacidad antioxidante total de los brotes de frambuesa roja fue de 164.12 mmol-equiv./m de peso seco, la suma del contenido total de compuestos fenólicos fue de 24.40 mg gálico ácido (GA)/mL, catequinas ­ 21.36 mg epigalocatequina-3-O-galato (EGCG)/mL, flavonoides ­ 0.77 mg rutina (R)/mL, derivados de ácidos hidroxicinámicos ­ 2.56 mg clorogénico ácido (ChA)/mL y ácidos orgánicos ­ 1.88 mg cítrico ácido (CA)/mL en extractos de brotes de frambuesa roja obtenidos durante extracción exhaustiva. La correlación analizada mostró que existe una correlación positiva entre la actividad antioxidante y el contenido de compuestos fenólicos totales, catequinas, flavonoides, derivados de ácidos hidroxicinámicos y ácidos orgánicos en extractos de brotes de frambuesa roja. Conclusiones: Gracias a nuestros resultados se ha determinado la capacidad antioxidante total de los brotes de frambuesa roja. Los resultados del estudio se pueden utilizar para desarrollar una tecnología óptima para la obtención de fármacos basados en el extracto de brotes de frambuesa roja, que tiene un efecto antioxidante

In Vitro Investigation of Antioxidant and Antidiabetic Properties of Phenolic-Rich Extract from Stingless Bee Honey (Heterotrigona itama)

@#Introduction: The increase of Type 2 diabetes mellitus has prompted numerous research toward finding an alternative to manage the disease through the oxidant-antioxidant balance, mainly through bioactive compounds in natural products. This study explored the antioxidant and antidiabetic properties of phenolic-rich extract (PRE) from Stingless bee honey (SBH) (Heterotrigona itama) as therapeutic agent to restore the redox balance. Methods: The total phenolic content (TPC), total flavonoid content (TFC) and antioxidant assays of PRE and SBH, were determined to provide preliminary insight into the sample’s antioxidant properties, followed by high-performance liquid chromatography analysis of PRE. The antidiabetic potential of PRE and SBH were determined based on their inhibition against α-amylase and α-glucosidase enzymes. The cytotoxicity analysis of PRE was conducted on 3T3-L1 adipocytes and L6 muscle cells before the glucose uptake and cellular antioxidant analyses were performed on both cell lines, respectively. Results: PRE yielded higher TPC, TFC and antioxidant activities than SBH. The phytochemical profile of PRE comprises gallic acid, myricetin, kaempferol, epicatechin, chlorogenic acid, quercetin, syringic acid, and cinnamic acid. The results from carbohydrate enzymatic inhibitory assays collectively suggested that PRE exhibited more robust antidiabetic activities than SBH. PRE showed good glucose uptake stimulating and reactive oxygen species scavenging effects in those cell lines. Conclusion: Overall, PRE from SBH showed higher carbohydrate enzymatic inhibition, glucose uptake, and protection against intracellular oxidative stress, primarily due to its high antioxidant content and may serve as an alternative therapeutic agent for managing T2DM.

Establishment of A Quality Control Method for Simultaneous Determination of Multiple Active Components in Uygur Medicine of Nymphaeae Flos / 中国实验方剂学杂志

ObjectiveTo develop a quality control method for the simultaneous determination of multiple active components in Nymphaeae Flos aiming at the problems of the single index for quality control and the relatively low overall quality control level. MethodUltra performance liquid chromatography-quadrupole-time-of-flight mass spectrometry（UPLC-Q-TOF-MS/MS）was used to identify and select the index components for quality control with the mobile phase of 0.1% formic acid aqueous solution（A）-acetonitrile（B）for gradient elution （0-2 min， 3%-8%B； 2-4 min， 8%-10%B； 4-13 min， 10%-15%B； 13-19 min， 15%-20%B； 19-26 min， 20%-45%B） at a flow rate of 0.4 mL·min-1， detection wavelength of 350 nm， electrospray ionization（ESI）， negative ion scanning mode， ion source temperature of 120 ℃， scanning range of m/z 100-1 200， transmit collision energy of 6 eV for low-energy scanning and 25-50 eV for high-energy scanning. High performance liquid chromatography（HPLC）was used to establish the quality control method for the simultaneous determination of multi-index components with the mobile phase of 0.2% phosphoric acid aqueous solution（A）-acetonitrile（B） for gradient elution（0-30 min， 12%-15%B； 30-60 min， 15%-22%B； 60-90 min， 22%-40%B）and detection wavelength of 350 nm. The preparation method of the test solution for content determination was refluxing extraction for 60 min with 80 times the amount of 70% methanol. ResultBy comparing the retention time， ultraviolet absorption characteristics， MS and MS/MS spectrometric signals in the samples with the reference substances， 8 active components with high contents， including brevifolincarboxylic acid， ellagic acid， rutin， nicotiflorin， astragalin， quercetin， quercetin-3-methylether and kaempferol， were identified qualitatively from Nymphaeae Flos， which were selected as the index components for quality control. Under the established HPLC conditions， the above 8 components could be well separated（resolution>1.5）， and showed good linearity（r=0.999 9）between the concentration ranges of 1.99-99.6， 1.76-176， 1.52-75.8， 3.60-180， 0.964-96.4， 1.18-118， 1.94-96.8， 1.04-104 mg·L-1 and the peak areas， respectively. The detection limits of them were 10-49 μg·L-1， and the limits of quantitation were 34-164 μg·L-1. The average recoveries were 97.12%-103.1% with the relative standard deviations （RSDs） were 1.1%-2.2%. ConclusionA quality control method for simultaneous determination of the multiple active components in Nymphaeae Flos have been developed， which is simple， accurate and reproducible， and it can provide a scientific basis for the formulation of quality standard of this herb and lay a research foundation for the transformation of Uygur hospital preparations containing Nymphaeae Flos into new drugs.

Phenolic glycosides from the stems and twigs of Strychnos cathayensis and their biological activities / 药学学报

Fourteen compounds were isolated from the n-butanol fraction of the 95% aqueous ethanol extract of the stems and twigs of Strychnos cathayensis by D101 macroporous resin, silica gel, ODS, Sephadex LH-20 column chromatography, and semipreparative RP-HPLC. Their structures were elucidated as ethyl 4-O-β-D-allopyranosyl-vanillate (1), n-butyl 4-O-β-D-allopyranosyl-vanillate (2), n-butyl 4-O-(6′-O-syringoyl)-β-D-allopyranosyl-vanillate (3), n-butyl 4-O-(6′-O-vanilloyl)-β-D-allopyranosyl-vanillate (4), n-butyl 4-O-(6′-O-syringoyl)-β-D-glucopyranosyl-vanillate (5), n-butyl 4-O-α-L-rhamnopyranosyl-syringate (6), methyl 3-methoxy-4-(β-D-allopyranosyloxy) benzoate (7), pseudolaroside B (8), butyl syringate (9), glucosyringic acid (10), methyl syringate (11), methyl 4-hydroxy-3-methoxybenzoate (12), clemochinenoside C (13), and clemoarmanoside A (14), respectively, on the basis of spectroscopic data interpretation and by comparison with literature information. Compounds 1-6 are artificial products of phenolic acid esterified by ethanol or n-butanol. It is noted that the precursors (4-O-(6′-O-syringoyl)-β-D-allopyranosyl-vanillic acid and 4-O-(6′-O-vanilloyl)-β-D-allopyranosyl-vanillic acid) of compounds 3 and 4 are new compounds. The hepatoprotective, anti-inflammatory, antioxidant and cytotoxic activities of compounds 1-13 were evaluated in vitro at a concentration of 10 μmol·L-1. Compounds 1, 2 and 6-10 exhibited potential hepatic protection effects with cell survival rates ranging from 53.6% to 55.5% (acetaminophen, 45.4% at 8 mmol·L-1). Compound 4 demonstrated anti-inflammatory activity with nitric oxide inhibitory rate of 74.6%. Compounds 3 and 5 showed potential antioxidant activities with malondialdehyde inhibitory rates of 53.2% and 56.1%, respectively.

Comparison of growth and quality of wild and cultivated Artemisia stolonifera / 中国中药杂志

This paper aims to compare the difference of growth and quality between wild and cultivated Artemisia stolonifera, thereby providing references for further development and utilization of A. stolonifera. The wild and cultivated A. stolonifera from different altitudes were collected, and the agronomic characters, moxa yield, volatile components, flavonoids, and phenolic acids were determined. The results showed that the cultivated species were taller and stronger, with more leaves and branches, than the wild species. The moxa yield and combustion quality of wild products were higher than those of cultivated products. The content of main volatile components in cultivated products was higher than that in wild products. The content of flavonoids and phenolic acids in wild products was higher than that in cultivated products. At high altitude, the ignition performance, combustion persistence, comprehensive combustion performance, and heat release during combustion of the wild and cultivated A. stolonifera. were optimal. At middle altitude, the content of main characteristic volatile components and flavone phenolic acids in the leaves of the cultivated and wild A. stolonifera were the highest. At low altitude, the combustion quality and the content of the above components of the cultivated A. stolonifera decrease significantly. Considering the combustion quality and the content of the internal components of the leaf lint, the middle and high altitude areas are suitable for the artificial cultivation of A. stolonifera.

Effects of shading intensity on growth and quality of Artemisia stolonifera / 中国中药杂志

The purpose of this study was to analyze the effects of shading intensity on the growth, yield, and quality of Artemisia stolonifera so as to provide references for the artificial cultivation of A. stolonifera. The seedlings of A. stolonifera with consistent growth underwent shading treatment at four shading intensity levels(0, 55%, 85%, and 95%) with different layers of black shading nets. The agronomic indexes, yield, moxa yield, total ash, quality characteristics of moxa during combustion and pyrolysis, main volatile components, flavonoids, and phenolic acids were measured. The results showed that under shading conditions, the stem diameter, leaf width, 5-leaf spacing, branch number, and yield of A. stolonifera decreased significantly, while the plant height, leaf length, leaf number, chlorophyll content, and moxa yield increased first and then decreased with the increase in shading intensity. The burning performance of moxa under natural light was better than that under moderate and severe shading conditions. The content of eucalyptol first increased and then decreased with the increase in shading intensity. The humulene content was negatively correlated with shading intensity. Other major volatile components showed no significant difference under various shading conditions. The content of neochlorogenic acid, cryptochlorogenic acid, isoschaftoside, and isochlorogenic acid B was positively correlated with shading intensity, while the content of chlorogenic acid, isochlorogenic acid A, and isochlorogenic acid C decreased first and then increased with the increase in shading intensity. To sum up, A. stolonifera is a light-loving plant, and shading can greatly reduce the yield, the content of internal components, and the burning performance of moxa. It is the main reason why A. stolonifera is mainly distributed in the forest edge, open forest, roadside, and wasteland grass in the middle and high mountains in the wild. For artificial domestication and cultivation of A. stolonifera, it is better to select plots with sufficient light.

Two new phenolic amides from Allium chinense / 中草药·英文版

OBJECTIVE@#To isolate the phenolic amides from the dried bulbs of Allium chinense and investigate their myocardium protective activities.@*METHODS@#The chemical constituents were isolated and purified by combining with silica gel column, Sephadex LH-20 column, HPLC and other chromatography techniques. Their structures were elucidated by NMR techniques and mass spectrometry. The isolated compounds were evaluated to determine their protective effect for myocardium cells in vitro.@*RESULTS@#Two new phenolic amides, namely, alichinemide I ( 1) and alichinemide II ( 2), and six konwn amides were isolated from the dried bulbs of A. chinense. The structures of compounds 3- 8 were identified as 3-indolcarbaldehyde ( 3), 1-(2-aminophenyl)urea ( 4), 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid ( 5), N-trans-feruloyltyramine ( 6), N-trans-p-coumaroyltyramine ( 7), and N-(3,4-dimethoxyphenethyl) acetamide ( 8). Compound 3 (50 μmol/L) showed significant inhibitory effect on the damage of H9c2 myocardial cells induced by H2O2in vitro.@*CONCLUSION@#Compounds 1 and 2 were new phenolic amides. Compound 3 could be one of the potential myocardium protective constituents of A. chinense.

In silico screening of Annona Muricata L. Leaf constituents and derivatives towards selected targets of Type 2 Diabetes Mellitus

BACKGROUND@#Type 2 diabetes mellitus, or T2DM, is one of the world's most chronic health problems that is linked to numerous deaths and high health care expenses. 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1), protein-tyrosine phosphatase 1B (PTP1B) and mono-ADP-ribosyl transferase sirtuin-6 (SIRT6) were among the novel proteins and focus targets of diabetes research. Annona muricata is a commonly used natural remedy for several illnesses, including type 2 diabetes mellitus. However, most of these traditional claims have received few molecular evaluations.@*OBJECTIVES@#This investigated the phytoconstituents and derivatives of the leaves of A. muricata by evaluating their binding profiles towards selected novel T2DM-related protein targets through in silico methods.@*METHODOLOGY@#This study screened the potential lead compounds from the leaves of A. muricata by evaluating the binding energies of the parent compounds and derivatives with the targets compared to the native ligands and known substrates through molecular docking simulations. Additionally, pharmacokinetic, physicochemical properties, and binding interactions were also assessed using several software programs and online databases.@*RESULTS@#Out of the 8 selected parent compounds of Annona muricata, a total of 672 derivatives were designed, tested, and compared against the controls for at least one of the three protein targets. Among these, 280 derivatives exhibited more negative binding energies than controls in each protein target.@*CONCLUSION@#The designed derivatives can be synthesized and further investigated for potential biological effects towards 11β-HSD1, PTP1B, and SIRT6 through in vitro and in vivo experiments.

Chemical constituents and their α-glucosidase inhibitory activities of seeds of Moringa oleifera / 中国中药杂志

The chemical constituents of the seeds of Moringa oleifera were isolated and purified by using Sephadex LH-20, Toyo-pearl HW-40F, silica gel, ODS, and MCI column chromatography. The structures of compounds were identified by high-resolution mass spectrometry, ~1H-NMR, ~(13)C-NMR, HMQC, HMBC, and ~1H-~1H COSY, as well as physicochemical properties of compounds and literature data. Twelve compounds were isolated from 30% ethanol fraction of the seeds of M. oleifera and identified as ethyl-4-O-α-L-rhamnosyl-α-L-rhamnoside(1), ethyl-3-O-α-L-rhamnosyl-α-L-rhamnoside(2),(4-hydroxybenzyl)ethyl carbamate(3),(4-aminophenyl)acetic acid(4), ethyl-α-L-rhamnoside(5), methyl-α-L-rhamnoside(6), moringapyranosyl(7), 2-[4-(α-L-rhamnosyl)phenyl]methyl acetate(8), niaziridin(9), 5-hydroxymethyl furfural(10), 4-hydroxybenzeneacetamide(11), and 4-hydroxybenzoic acid(12). Among them, compounds 1 and 2 are two new compounds, compound 3 is a new natural product, and compounds 4-5 were yielded from Moringa plant for the first time. All compounds were evaluated for α-glucosidase inhibitory activity in vitro. Compound 10 showed excellent inhibitory activity with IC_(50) of 210 μg·mL~(-1).

Chemical composition and antioxidant activity of different parts of Prunella vulgaris by UPLC-Q-TOF-MS/MS and UPLC / 中国中药杂志

Prunellae Spica is the dried spica of Prunella vulgaris belonging to Labiatae and it is widely used in pharmaceutical and general health fields. As a traditional Chinese medicine cultivated on a large scale, it produces a large amount of non-medicinal parts, which are discarded because they are not effectively used. To analyze the chemical constituents in the different samples from spica, seed, stem, and leaf of P. vulgaris, and explore the application value and development prospect of these parts, this study used ultrahigh performance liquid chromatography-tandem quadrupoles time of flight mass spectrometry(UPLC-Q-TOF-MS/MS) to detect chemical constituents in different parts of P. vulgaris. As a result, 117 compounds were detected. Among them, 87 compounds were identified, including 32 phenolic acids, 8 flavonoids, and 45 triterpenoid saponins. Some new triterpenoid saponins containing the sugar chain with 4-6 sugar units were found. Further, multivariate statistical analysis was conducted on BPI chromatographic peaks of multiple batches of different parts, and the results showed that spica had the most abundant chemical constituents, including salviaflaside and linolenic acid highly contained in the seed and phenolic acids, flavonoids, and triterpenoid saponins in the stem and leaf. In general, the constituents in the spica were composed of those in the seed, stem, and leaf. UPLC was used to determine the content of 6 phenolic acids(danshensu, protocatechuic acid, protocatechuic aldehyde, caffeic acid, salviaflaside, and rosmarinic acid) in different parts. The content of other phenolic acids in the seed was generally lower than that in the spica except that of salviaflaside. The content of salviaflaside in the spica was higher than that in the stem and leaf, but the content of other phenolic acids in the spica was not significantly different from that in the stem. The content of protocatechuic aldehyde and caffeic acid in the spica was lower than that in the leaf. DPPH free radical scavenging method was used to detect the antioxidant activity of four parts, and there was no significant difference in the antioxidant activity between the spica and the stem and leaf, but that was significantly higher than the seed. Moreover, the antioxidant activity of these parts was correlated with the content of total phenolic acids. Based on the above findings, the stem and leaf of P. vulgaris have potential application value. Considering the traditional medication rule, it is feasible to use the whole plant as a medicine. Alternatively, salviaflaside, occurring in the seed, can be used as a marker compound for the quality evaluation of Prunellae Spica, if only using spica as the medicinal part of P. vulgaris, as described in the Chinese Pharmacopoeia(2020 edition).

Heterocyclic compounds and phenolic glycosides from flowers of Dendrobium officinale / 中国中药杂志

Eight heterocyclic compounds and twelve phenolic glycosides were separated from the water extract of Dendrobium officinale flowers through chromatographic techniques, such as Diaion HP-20 macroporous adsorption resin column chromatography(CC), silica gel CC, ODS CC, Sephadex LH-20 CC, and preparative high performance liquid chromatography(PHPLC). According to the spectroscopic analyses(MS, ~1H-NMR, and ~(13)C-NMR) and optical rotation data, the compounds were identified as dendrofurfural A(1), 2'-deoxyadenosine(2), 4-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl] butanoic acid(3), 4-[2-formyl-5-(methoxymethyl)-1H-pyrrol-1-yl] butanoic acid(4), 1-(2-hydroxyethyl)-5-(methoxymethyl)-1H-pyrrole-2-carbaldehyde(5), 5-(methoxymethyl)-1H-pyrrole-2-carbaldehyde(6), methyl 5-(hydroxymethyl)-furan-2-carboxylate(7),(S)-5-hydroxymethyl-5H-furan-2-one(8), 2-methoxyphenyl-1-O-β-D-glucopyranoside(9), arbutin(10), isotachioside(11), 2,6-dimethoxy-4-hydroxyphenol-1-O-β-D-glucopyranoside(12), orcinol glucoside(13), tachioside(14), gastrodin(15), 4-O-β-D-glucopyranosylvanillyl alcohol(16), 2,6-dimethoxy-4-hydroxymethylphenol-1-O-β-D-glucopyranoside(17), icariside D_2(18), 4-formylphenyl-β-D-glucopyranoside(19), and vanillin-4-O-β-D-glucopyranoside(20). Among them, compound 1 is a new furfural benzyl alcohol condensate, with the skeleton first found in Dendrobium. Compounds 2-9, 11, 13, and 19 are reported from Dendrobium for the first time, and compounds 14 and 18 are reported for the first time from D. officinale. Compounds 11 and 14 showed moderate DPPH radical scavenging capacity, and compounds 11-14 demonstrated potent ABTS radical scavenging capacity, possessing antioxidant activity.

Neuroprotective effects of Longxue Tongluo Capsule on ischemic stroke rats revealed by LC-MS/MS-based metabolomics approach / 中草药·英文版

OBJECTIVE@#The present study aimed to evaluate the therapeutic effect and explore the underlying mechanisms of Longxue Tongluo Capsule (LTC) on ischemic stroke rats.@*METHODS@#Twenty-six rats were randomly divided into four groups, including sham group, sham + LTC group, MCAO group, and MCAO + LTC group. Ischemic stroke rats were simulated by middle cerebral artery occlusion (MCAO), and LTC treatment group were orally administrated with 300 mg/kg of LTC once daily for seven consecutive days. LTC therapy was validated in terms of neurobehavioral abnormality evaluation, cerebral infarct area, and histological assessments. The plasma metabolome comparisons amongst different groups were conducted by UHPLC-Q Exactive MS in combination with subsequent multivariate statistical analysis, aiming to finding the molecules in respond to the surgery or LTC treatment.@*RESULTS@#Intragastric administration of LTC significantly decreased not only the neurobehavioral abnormality scores but also the cerebral infarct area of MCAO rats. The interstitial edema, atrophy, and pyknosis of glial and neuronal cells occurred in the infarcted area, core area, and marginal area of cerebral cortex were improved after LTC treatment. A total of 13 potential biomarkers were observed, and Youden index of 11 biomarkers such as LysoPC, SM, and PE were more than 0.7, which were involved in neuroprotective process. The correlation and pathway analysis showed that LTC was beneficial to ischemic stroke rats via regulating glycerophospholipid and sphingolipid metabolism, together with nicotinate and nicotinamide metabolism. Heatmap and ternary analysis indicated the synergistic effect of carbohydrates and lipids may be induced by flavonoid intake from LTC.@*CONCLUSION@#The present study could provide evidence that metabolomics, as systematic approach, revealed its capacity to evaluate the holistic efficacy of TCM, and investigate the molecular mechanism underlying the clinical treatment of LTC on ischemic stroke.

Glucuronic acid metabolites of phenolic acids target AKT-PH domain to improve glucose metabolism / 中草药·英文版

OBJECTIVE@#Phenolic acids widely exist in the human diet and exert beneficial effects such as improving glucose metabolism. It is not clear whether phenolic acids or their metabolites play a major role in vivo. In this study, caffeic acid (CA) and ferulic acid (FA), the two most ingested phenolic acids, and their glucuronic acid metabolites, caffeic-4'-O-glucuronide (CA4G) and ferulic-4'-O-glucuronide (FA4G), were investigated.@*METHODS@#Three insulin resistance models in vitro were established by using TNF-α, insulin and palmitic acid (PA) in HepG2 cells, respectively. We compared the effects of FA, FA4G, CA and CA4G on glucose metabolism in these models by measuring the glucose consumption levels. The potential targets and related pathways were predicted by network pharmacology. Fluorescence quenching measurement was used to analyze the binding between the compounds and the predicted target. To investigate the binding mode, molecular docking was performed. Then, we performed membrane recruitment assays of the AKT pleckstrin homology (PH) domain with the help of the PH-GFP plasmid. AKT enzymatic activity was determined to compare the effects between the metabolites with their parent compounds. Finally, the downstream signaling pathway of AKT was investigated by Western blot analysis.@*RESULTS@#The results showed that CA4G and FA4G were more potent than their parent compounds in increasing glucose consumption. AKT was predicted to be the key target of CA4G and FA4G by network pharmacology analysis. The fluorescence quenching test confirmed the more potent binding to AKT of the two metabolites compared to their parent compounds. The molecular docking results indicated that the carbonyl group in the glucuronic acid structure of CA4G and FA4G might bind to the PH domain of AKT at the key Arg-25 site. CA4G and FA4G inhibited the translocation of the AKT PH domain to the membrane, while increasing the activity of AKT. Western blot analysis demonstrated that the metabolites could increase the phosphorylation of AKT and downstream glycogen synthase kinase 3β in the AKT signaling pathway to increase glucose consumption.@*CONCLUSION@#In conclusion, our results suggested that the metabolites of phenolic acids, which contain glucuronic acid, are the key active substances and that they activate AKT by targeting the PH domain, thus improving glucose metabolism.

Antioxidant potential and α-glucosidase inhibitory activity of onion (Allium cepa L. ) peel and bulb extracts / Atividade antioxidante e potencial inibidor de glucosidase de extratos de casca e bulbo de cebola (Allium cepa) preparados por etanol e água

Abstract Allium cepa L. is a commonly consumed vegetable that belongs to the Amaryllidaceae family and contains nutrients and antioxidants in ample amounts. In spite of the valuable food applications of onion bulb, its peel and outer fleshy layers are generally regarded as waste and exploration of their nutritional and therapeutic potential is still in progress with a very slow progression rate. The present study was designed with the purpose of doing a comparative analysis of the antioxidant potential of two parts of Allium cepa, i.g., bulb (edible part) and outer fleshy layers and dry peels (inedible part). Moreover, the inhibitory effect of the onion bulb and peel extracts on rat intestinal α-glucosidase and pancreatic α-amylase of porcine was also evaluated. The antioxidant potential of onion peel and bulb extracts were evaluated using 2,2-diphenyl- 1-picryl hydrazyl (DPPH), ferric-reducing antioxidant power assay (FRAP), 2,2'-azino-bis- 3-ethylbenzothiazoline-6-sulfonic acid (ABTS) radical scavenging assay, H2O2 radical scavenging activity and Fe2+ chelating activity. Total flavonoids and phenolic content of ethanolic extract of onion peel were significantly greater as compared to that of onion bulb. Ethanolic extract of onion peel also presented better antioxidant and free-radical scavenging activity as compared to the ethanolic extract of bulb, while the aqueous extract of bulb presented weakest antioxidative potential. Onion peel extract's α-glucosidase inhibition potential was also correlated with their phenolic and flavonoid contents. The current findings presented onion peel as a possible source of antioxidative agents and phenolic compounds that might be beneficial against development of various common chronic diseases that might have an association with oxidative stress. Besides, outer dry layers and fleshy peels of onion exhibited higher phenolic content and antioxidant activities, compared to the inner bulb. The information obtained by the present study can be useful in promoting the use of vegetable parts other than the edible mesocarp for several future food applications, rather than these being wasted.

Resumo Allium cepa pertence à família Liliaceae e é rica em nutrientes e antioxidantes. Apesar das expressivas aplicações alimentares do bulbo da cebola, sua casca e outras camadas externas são geralmente consideradas resíduos, e seu potencial nutricional e terapêutico ainda é pouco explorado. O presente estudo foi delineado com o objetivo de investigar comparativamente o potencial antioxidante de duas partes de Allium cepa, por exemplo o bulbo (parte comestível) e camadas externas e cascas secas (parte não comestível). Além disso, o efeito inibitório dos extratos do bulbo de cebola e casca sobre a α-glucosidase intestinal de ratos e α-amilase pancreática suína também foi avaliado. O potencial antioxidante dos extratos da casca de cebola e bulbo foi avaliado utilizando-se 2,2-difenil-1-picrilhidrazil (DPPH), método de poder antioxidante de redução do ferro (FRAP), método 2,2'-azino-bis-3-etilbenzotiazolina-6-ácido sulfônico (ABTS) de eliminação de radicais, atividade de eliminação de radicais H2O2 e atividade quelante do Fe2+. Os flavonoides totais e os teores fenólicos do extrato de etanol da casca de cebola foram significativamente maiores quando comparados ao do bulbo. O extrato de etanol da casca de cebola também apresentou melhor atividade antioxidante e eliminação de radicais livres quando comparado ao extrato de etanol do bulbo, enquanto o extrato aquoso de bulbo apresentou menor potencial antioxidante. O potencial de inibição da α-glicosidase dos extratos de casca de cebola correlacionou-se com seus teores fenólicos e de flavonoides. Os resultados encontrados identificaram que a casca de cebola é uma possível fonte de agentes antioxidantes e compostos fenólicos que podem ser benéficos contra o desenvolvimento de várias doenças crônicas que estão associadas ao estresse oxidativo. Além disso, as camadas externas secas e as cascas da cebola exibiram maior conteúdo fenólico e atividades antioxidantes, em comparação com o bulbo interno. As informações obtidas pelo presente estudo podem promover o uso de outras partes vegetais além do mesocarpo comestível para futuras aplicações em alimentos, ao invés de serem desperdiçadas.