Phenolic Constituents from Wendlandia tinctoria var. grandis (Roxb.) DC. Stem Deciphering Pharmacological Potentials against Oxidation,Hyperglycemia, and Diarrhea: Phyto-Pharmacological and Computational Approaches

Wendlandia tinctoria var. grandis (Roxb.) DC. (Family: Rubiaceae) is a semi-evergreen shrub distributed over tropical and subtropical Asia. The present research intended to explore the pharmacological potential of the stem extract of W. tinctoria, focusing on the antioxidant, hypoglycemic, and antidiarrheal properties, and to isolate various secondary metabolites as mediators of such activities. A total of eight phenolic compounds were isolated from the dichloromethane soluble fraction of the stem extract of this plant, which were characterized by electrospray ionization (ESI) mass spectrometric and ¹H NMR spectroscopic data as liquiritigenin (1), naringenin (2), apigenin (3), kaempferol (4), glabridin (5), ferulic acid (6), 4-hydroxybenzoic acid (7), and 4-hydroxybenzaldehyde (8). The dichloromethane soluble fraction exhibited the highest phenolic content (289.87 ± 0.47 mg of GAE/g of dried extract) and the highest scavenging activity (IC₅₀ = 18.83 ± 0.07 µg/mL) against the DPPH free radical. All of the isolated compounds, except 4-hydroxybenzaldehyde, exerted a higher antioxidant effect (IC₅₀ = 6.20 ± 0.10 to 16.11 ± 0.02 μg/mL) than the standard butylated hydroxytoluene (BHT) (IC₅₀ = 17.09 ± 0.01 μg/mL). Significant hypoglycemic and antidiarrheal activities of the methanolic crude extract at both doses (200 mg/kg bw and 400 mg/kg bw) were observed in a time-dependent manner. Furthermore, the computational modeling study supported the current in vitro and in vivo findings, and the isolated constituents had a higher or comparable binding affinity for glutathione reductase and urase oxidase enzymes, glucose transporter 3 (GLUT 3), and kappa-opioid receptor, inferring potential antioxidant, hypoglycemic, and antidiarrheal properties, respectively. This is the first report of all of these phenolic compounds being isolated from this plant species and even the first demonstration of the plant stem extract’s antioxidant, hypoglycemic, and antidiarrheal potentials. According to the current findings, the W. tinctoria stem could be a potential natural remedy for treating oxidative stress, hyperglycemia, and diarrhea. Nevertheless, further extensive investigation is crucial for thorough phytochemical screening and determining the precise mechanisms of action of the plant-derived bioactive metabolites against broad-spectrum molecular targets.     

Three New Pregnane Glycosides from Marsdenia tinctoria

Three new pregnane glycosides, tinctorosides A–C ( 1 – 3 , resp.), together with one known pregnane glycoside, stephanoside B ( 4 ), were isolated from the stems of Marsdenia tinctoria R. Br . (Asclepiadaceae). Their structures were elucidated by extensive spectral methods, especially 2D‐NMR experiments (¹H,¹H‐COSY, HSQC, HMBC, TOCSY, HSQC‐TOCSY, and ROESY), and chemical evidence.     

The chemical components of Coreopsis tinctoria Nutt. and their antioxidant,antidiabetic and antibacterial activities

Abstract

Seventeen compounds were isolated from the capitula of Coreopsis tinctoria Nutt. with various column chromatographic methods and semi-preparative HPLC. Their structures were identified by the spectroscopic data and comparison with literatures as 2′-hydroxy-4,4′-dimethoxy-chalcone; (1), isoliquiritigenin (2), eriodictyol (3), naringenin (4), maritimetin (5), butin (6), taxifolin (7), luteolin (8), 7,3′,4′-trihydroxyflavone (9), 8,3′,4′-trihydroxyflavone-7-O-β-d-glucoside (10), quercetin (11), quercetagitin-7-O-β-d-glucoside (12), quercetin-7-O-β-d-glucoside (13), 3,4-dihydroxybenzoic acid (14), caffeic acid (15), coreoside B (16), and myo-inositol (17). Compounds 1, 4, 9, 10 and 17 were isolated from C. tinctoria Nutt. for the first time. Compounds 7 and 12 possessed the highest antioxidant activity (IC₅₀?=?64.37 and 32.86?µg/ml, respectively) among the tested compounds (IC₅₀ value of positive control was 5.34?µg/ml). Compound 7 exhibited potent PTP1B enzymatic inhibition with an IC₅₀ value of 7.73?μg/ml (IC₅₀ value of positive control is 1.46?µg/ml). Furthermore, compound 5 showed strong antibacterial activity against the Gram-positive bacterium, S. aureus.     

Comparative study on the antioxidant activities of extracts of Coreopsis tinctoria flowering tops from Kunlun Mountains,Xinjiang, north-western China

Coreopsis tinctoria flowering tops (CTFs) from the Kunlun Mountains in Xinjing (north-western China) have been used for tea production for about a century. This study aims to assess the antioxidant activities and total phenolic, flavonoid and proanthocyanidin contents of various solvent extracts of CTF. CTF was extracted using n-hexane, chloroform, ethyl acetate, n-butanol, 75% aqueous ethanol (AEE) and water. The antioxidant activities of the CTF extracts were investigated through DPPH, ABTS, ^*OH, ^*O₂^? , total antioxidant capacity and reducing power assays. The results showed that n-butanol extract showed the highest contents of total phenols and flavonoids, with DPPH, ABTS and ^*OH radical-scavenging activities with IC₅₀ values of 134, 90.72 and 13.8 μg mL^? 1, respectively. The AEE demonstrated the strongest DPPH and ABTS radical-scavenging activities, with IC₅₀ values of 103 and 75.16 μg mL^? 1, respectively. Given its high antioxidant effect, CTF is a good source of natural antioxidants or functional food materials.     

Chemical characteristics of different parts of Coreopsis tinctoria in China using microwave‐assisted extraction and high‐performance liquid chromatography followed by chemometric analysis

Coreopsis tinctoria, also called “snow chrysanthemum” in China, is a flower tea material that has been reported to possess excellent pharmacological properties such as antioxidant and antidiabetic activities. The chemical characteristics of different parts (flowers, buds, seeds, stems, and leaves) of C. tinctoria were investigated based on microwave‐assisted extraction and the simultaneous determination of 13 major active compounds by high‐performance liquid chromatography, including taxifolin‐7‐O‐glucoside, chlorogenic acid, (R/S)‐flavanomarein, isocoreopsin, quercetagetin‐7‐O‐glucoside, isookanin, 5,7,3′,5′‐tetrahydroxyflavanone‐7‐O‐glucoside, marein, 3,5‐dicaffeoylquinic acid, coreopsin, okanin, 5,7,3′,5′‐tetrahydroxyflavanone, and N¹,N⁵,N¹⁰,N¹⁴‐tetra‐p‐coumaroylspermine. Chemometric analysis based on the contents of investigated compounds from 13 samples showed that C. tinctoria and the related flower tea materials, Chrysanthemum morifolium cv “Hangju” and “Gongju,” were in different clusters, and different parts (flowers, buds, seeds, stems, and leaves) of C. tinctoria were obviously different. This study is helpful for the quality control and pharmacological evaluation of different parts from C. tinctoria and its related products.     

Phytochemical constituents and chemosystematic significance of Chrozophora tinctoria (L.) Raf

Twelve compounds were isolated from Chrozophora tinctoria (L.) Raf. They were identified as kaempferol, kaempferol 3-O-β-glucopyranoside, kaempferol 3-O-(6″-α-rhamnopyranosyl)-β-glucopyranoside, quercetin, quercetin 3-O-β-glucopyranoside, quercetin 3-O-(6″-α-rhamnopyranosyl)-β-glucopyranoside, apigenin, apigenin 7-O-β-glucopyranoside, acacetin, gallic acid, methyl gallate and β-sitosterol-3-O-β-glucopyranoside. Their structures were elucidated by chemical and spectral methods. Furthermore, chemosystematics of the isolated compounds is briefly discussed. It was indicated that C. tinctoria is the only species of Chrozophora that has the capability to synthesis kaempferol aglycone and their glycosides, and the finding is supported by its distinct morphological and anatomical aspects.     

Prokinetic and Laxative Effects of Chrozophora tinctoria Whole Plant Extract

Chrozophora tinctoria (Euphorbiaceae) has been used as an emetic, anthelminthic, and cathartic agent in traditional medicine. We used gas chromatography-mass spectrometry (GC-MS) to characterize the composition of ethyl acetate (EAC) and dichloromethane (DCMC) fractions from the whole Chrozophora tinctoria plant. EAC and DCMC fractions were evaluated for acetylcholinesterase (AChE) inhibitory activity and acute toxicity. Their effects on intestinal propulsive movement and spasmogenic activity of the gastrointestinal tract (GIT) muscle were also assessed. The compounds detected in both fractions were mostly fatty acids, with about seven compounds in EAC and 10 in DCMC. These included pharmacologically active compounds such as imipramine, used to treat depression, or hexadecanoic acid methyl ester, an antioxidant. Both EAC and DCMC fractions inhibited acetylcholinesterase (AChE) activity with IC₅₀ values of 10 µg and 130 µg, respectively. Both the fractions were found to be toxic in a dose-dependent manner, inducing emesis at 0.5 g or higher and lethargy and mortality from 3–5 g upwards. Similarly, both of the fractions showed laxative activity in metronidazole- and loperamide-induced constipation models. EAC relaxed the intestinal muscle at a lower dose (1 mg/mL) than DCMC. Similarly, the EAC extract showed a significant relaxation effect (EC₅₀ = 0.67 ± 0.15 mg/mL) on KCL-induced contraction in rabbit jejunum as compared to DCMC (EC₅₀ = 5.04 ± 0.05 mg/kg). The present study strongly supports the folklore that this valuable plant is a cathartic agent. Further work is required to isolate and validate the bioactive compounds that act as diarrheal agents in Chrozophora tinctoria.     

昆仑雪菊中黄酮类化合物提取与纯化

用超声法提取昆仑雪菊中黄酮类化合物,通过大孔树脂对提取液进行纯化,纯化物经聚酰胺层析柱梯度洗脱得到初步分离物,通过颜色反应和紫外光谱扫描进行定性分析。设计正交实验得到超声法提取的最佳工艺条件是65%乙醇、料液比为1∶40、超声时间60 min,此条件下提取3次,总黄酮得率可达132.6 mg/g。通过聚酰胺柱层析法分离出五个组分,初步判断它们属于不同的黄酮类物质。超声法提取总黄酮,提取率较高,聚酰胺树脂对黄酮类化合物的分离效果较好。     

Extraction and Fractionation of Prokinetic Phytochemicals from Chrozophora tinctoria and Their Bioactivities

Chrozophora tinctoria is an annual plant of the family Euphorbiaceae, traditionally used as a laxative, a cathartic and an emetic. A methanolic extract of Chrozophora tinctoria (MEC) whole plant and an n-butanol fraction of Chrozophora tinctoria (NBFC) were analyzed by gas chromatography–mass spectrometry (GC-MS) to detect the phytochemicals. MEC and NBFC were tested for in vitro anti acetylcholinesterase (AChE) potential. The effect of both samples on intestinal propulsive movement and spasmolytic activity in the gastrointestinal tract (GIT) was also studied. About twelve compounds in MEC and three compounds in NBFC were tentatively identified through GC-MS. Some of them are compounds with known therapeutic activity, such as toluene; imipramine; undecane; 14-methyl-pentadecanoic acid methyl ester; and hexadecanoic acid. Both NBFC and MEC samples were checked for acute toxicity and were found to be highly toxic in a dose-dependent manner, causing diarrhea and emesis at 1 g/kg concentration in pigeons, with the highest lethargy and mortality above 3 g/kg. Both the samples of Chrozophora tinctoria revealed significant (p ≤ 0.01) laxative activity against metronidazole (7 mg/kg) and loperamide hydrochloride (4 mg/kg)-induced constipation. NBFC (81.18 ± 2.5%) and MEC (68.28 ± 2.4%) significantly increased charcoal meal intestinal transit compared to distal water (41.15 ± 4.3%). NBFC exhibited a significant relaxant effect (EC₅₀ = 3.40 ± 0.20 mg/mL) in spontaneous rabbit jejunum as compared to MEC (EC₅₀ = 4.34 ± 0.68 mg/kg). Similarly, the impact of NBFC on KCl-induced contraction was more significant than that of MEC (EC₅₀ values of 7.22 ± 0.06 mg/mL and 7.47 ± 0.57 mg/mL, respectively). The present study scientifically validates the folk use of Chrozophora tinctoria in the management of gastrointestinal diseases such as constipation. Further work is needed to isolate the phytochemicals that act as diarrheal agents in Chrozophora tinctoria.