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MOLECULES · 2019 ·Vol. 24 ·期 16 ·2906 · IF 3.06

Terpene Glycosides from Sanguisorba officinalis and Their Anti-Inflammatory Effects

Da-Le Guo,Jin-Feng Chen,Lu Tan,Meng-Ying Jin,Feng Ju,Zhi-Xing Cao,Fang Deng,Li-Na Wang,Yu-Cheng Gu,Yun Deng

Two new terpene glycosides (1–2) along with two known analogs (3–4) were obtained from the root ofSanguisorba officinalis,which is a common traditional Chinese medicine (TCM). Their structures were elucidated by nuclear magnetic resonance (NMR), electrospray ionization high resolution mass spectrometry (HRESIMS), and a hydrolysis reaction, as well as comparison of these data with the literature data. Compounds1–4exhibited anti-inflammatory propertiesin vitroby attenuating the production of inflammatory mediators, such as nitric oxide (NO) as well as tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6). An anti-inflammatory assay based on the zebrafish experimental platform indicated that compound1had good anti-inflammatory activity in vivo by not only regulating the distribution, but also by reducing the amount of the macrophages of the zebrafish exposed to copper sulfate.Keywords:terpene glycosides;structural elucidation;Sanguisorba officinalis;zebrafish;anti-inflammatory

CAS / MDL: 103-72-0
研究领域: 药理学 · 化学 · 生物学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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MOLECULES · 2021 ·Vol. 26 ·期 14 ·4300 · IF 4.412

Ferroptosis-Inhibitory Difference between Chebulagic Acid and Chebulinic Acid Indicates Beneficial Role of HHDP

Lin Yang,Yangping Liu,Wenhui Zhang,Yujie Hua,Ban Chen,Quanzhou Wu,Dongfeng Chen,Shuqin Liu,Xican Li

The search for a safe and effective inhibitor of ferroptosis, a recently described cell death pathway, has attracted increasing interest from scientists. Two hydrolyzable tannins, chebulagic acid and chebulinic acid, were selected for the study. Their optimized conformations were calculated using computational chemistry at the B3LYP-D3(BJ)/6-31G and B3LYP-D3(BJ)/6-311 + G(d,p) levels. The results suggested that (1) chebulagic acid presented a chair conformation, while chebulinic acid presented a skew-boat conformation; (2) the formation of chebulagic acid requires 762.1729 kcal/mol more molecular energy than chebulinic acid; and (3) the 3,6-HHDP (hexahydroxydiphenoyl) moiety was shown to be in an (R)- absolute stereoconfiguration. Subsequently, the ferroptosis inhibition of both tannins was determined using a erastin-treated bone marrow-derived mesenchymal stem cells (bmMSCs) model and compared to that of ferrostatin-1 (Fer-1). The relative inhibitory levels decreased in the following order: Fer-1 > chebulagic acid > chebulinic acid, as also revealed by the in vitro antioxidant assays. The UHPLC–ESI-Q-TOF-MS analysis suggested that, when treated with 16-(2-(14-carboxytetradecyl)-2-ethyl-4,4-dimethyl-3-oxazolidinyloxy free radicals, Fer-1 generated dimeric products, whereas the two acids did not. In conclusion, two hydrolyzable tannins, chebulagic acid and chebulinic acid, can act as natural ferroptosis inhibitors. Their ferroptosis inhibition is mediated by regular antioxidant pathways (ROS scavenging and iron chelation), rather than the redox-based catalytic recycling pathway exhibited by Fer-1. Through antioxidant pathways, the HHDP moiety in chebulagic acid enables ferroptosis-inhibitory action of hydrolyzable tannins.Keywords:ferroptosis-inhibition;ferrostatin-1;chebulagic acid;chebulinic acid;hydrolyzable tannin;HHDP

CAS / MDL: 1898-66-4
研究领域: 生物化学 · 细胞生物学 · 药理学
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WORLD JOURNAL OF GASTROENTEROLOGY · 2020 · IF 3.665

Antioxidant activity and hepatoprotective effect of 10 medicinal herbs on CCl4-induced liver injury in mice

Xiao Meng,Guo-Yi Tang,Pin-He Liu,Chan-Juan Zhao,Qing Liu,Hua-Bin Li

BACKGROUND Many natural products confer health benefits against diverse diseases through their antioxidant activities. Carbon tetrachloride (CCl 4 ) is often used in animal experiments to study the effects of substances on liver injury and the related mechanisms of action, among which oxidative stress is a major pathogenic factor. AIM To compare antioxidant and hepatoprotective activities of ten herbs and identify and quantify phytochemicals for the one with strongest hepatoprotection. METHODS The antioxidant activity of ten medicinal herbs was determined by both ferric-reducing antioxidant power and Trolox equivalent antioxidant capacity assays. The total phenolic and flavonoid contents were determined by Folin–Ciocalteu method and aluminum chloride colorimetry, respectively. Their effects on CCl 4 -induced oxidative liver injury were evaluated and compared in a mouse model by administrating each water extract (0.15 g/mL, 10 mL/kg) once per day for seven consecutive days and a dose of CCl 4 solution in olive oil (8%, v/v, 10 mL/kg). The herb with the strongest hepatoprotective performance was analyzed for the detailed bioactive components by using high-performance liquid chromatography-electrospray ionization source-ion trap tandem mass spectrometry. RESULTS The results revealed that all tested herbs attenuated CCl 4 -induced oxidative liver injury; each resulted in significant decreases in levels of serum alanine transaminase, aspartate transaminase, alkaline phosphatase, and triacylglycerols. In addition, most herbs restored hepatic superoxide dismutase and catalase activities, glutathione levels, and reduced malondialdehyde levels. Sanguisorba officinalis ( S. officinalis ) L., Coptis chinensis Franch., and Pueraria lobata (Willd.) Ohwi root were the three most effective herbs, and S. officinalis L. exhibited the strongest hepatoprotective effect. Nine active components were identified in S. officinalis L. Gallic acid and (+)-catechin were quantified (7.86 ± 0.45 mg/g and 8.19 ± 0.57 mg/g dried weight, respectively). Furthermore, the tested herbs displayed a range of in vitro antioxidant activities proportional to their phenolic content; the strongest activities were also found for S. officinalis L. CONCLUSION This study is of value to assist the selection of more effective natural products for direct consumption and the development of nutraceuticals or therapeutics to manage oxidative stress-related diseases.

CAS / MDL: 8001-25-0
研究领域: 药理学 · 肝病学 · 天然产物化学
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NATURAL PRODUCT RESEARCH · 2020 · IF 2.158

Phenolic glycosides from Sanguisorba officinalis and their anti-inflammatory effects

Jin-feng Chen,Lu Tan,Feng Ju,Qi-xuan Kuang,Tian-long Yang,Fang Deng,Yu-cheng Gu,Li-shi Jiang,Yun Deng,Da-le Guo

Two new phenolic glycosides 7R,8R-threo-4,7,9,9'-tetrahydroxy-3-methoxy-8-O-4'-neolignan-3'-O-(3''-α-L-arabinofuranosyl)-β-D-glucopyranoside. (1), 4-(4'-hydroxyphenyl)-2-butanone-4''-O-(6-β-D-xylosyl)-β-D-glucopyranoside (2), along with two known related analogues 7R,8R-threo-4,7,9,9'-tetrahydroxy-3-methoxy-8-O-4'-neolignan-3'-O-β-D-glucopyranoside (3), 4-(4'-hydroxyphenyl)-2-butanone-4'-O-β-D-glucopyranoside (4) were obtained from the roots of Sanguisorba officinalis. Combined with acid hydrolysis derivatization, the absolute configurations of these new compounds were elucidated by comprehensive analyses of spectroscopic data including nuclear magnetic resonance (NMR), electrospray ionization high resolution mass (HRESIMS) as well as circular dichroism (CD). Compounds 1-4 exhibited anti-inflammatory properties in vitro by attenuating the production of inflammatory mediators, such as nitric oxide (NO) as well as tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6).

CAS / MDL: 103-72-0
研究领域: 药理学 · 化学 · 植物科学
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Food & Function · 2019 ·Vol. 10 ·期 11 ·7142-7151 · IF 3.241

Structural characterization and in vitro–in vivo evaluation of effect of a polysaccharide from Sanguisorba officinalis on acute kidney injury

Wenwen Zhao,Xi Zeng,Fancheng Meng,Xiaolin Bi,Dahai Xu,Xiuping Chen,Qiu Li,Yantao Han

We report here an acidic polysaccharide, namely RSP-3, which ameliorates acute kidney injury and is obtained from Sanguisorba officinalis. We extracted and purified two polysaccharides from this herb based on the acidity and screened them for their effect in regulating the immunological activity of macrophages. Among them, RSP-3 exhibited significant anti-inflammatory activity against lipopolysaccharide (LPS)-stimulated macrophages by decreasing TNF-α and IL-6 levels. Subsequently, we found that RSP-3 suppressed ER stress, reduced ROS production and blocked NF-κBp65 translocation. After fully characterizing RSP-3 with a series of analytical technologies, we tested its anti-acute kidney injury (AKI) effect in vivo. In a murine AKI model induced by LPS, treatment with RSP-3 effectively ameliorated renal function. Besides, it decreased the levels of TNF-α and IL-6 in serum and reduced macrophage infiltration in injured kidney tissue. In sum, RSP-3, with a significant protective effect against AKI by showing anti-inflammatory activity, may become a meaningful drug candidate for treatment of AKI.

研究领域: 药理学 · 免疫学 · 分子生物学 · 肾病学
✓ 已验证 DOI PubMed 高影响因子
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Frontiers in Molecular Biosciences · 2022 · IF 6.113

Investigation of Tannins Transformation in Sanguisorbae Radix Over Carbonizing by Stir-Frying

Wei Gu,Hao Wang,Man Su,Yiwei Wang,Fei Xu,Qinglian Hu,Xuyi Cai,Jinyun Song,Huangjin Tong,Yuerong Qian,Hongyu Zhao,Jun Chen

Carbonizing by stir-frying (CSF) is the most common technology in botanical folk medicines to enhance the convergence, hemostasis, and antidiarrheal effects. Sanguisorbae Radix (SR), a well-known herbal medicine in China, has extensive therapeutic functions, while charred SR is known as an additional product obtained from SR after CSF. In this study, mass spectrometry was used to investigate the effect of charring on tannins transformation of SR. The findings showed that the content level of tannins in SR decreased significantly after carbonizing process, while their three categories, gallotannins, ellagitannins, and procyanidins, had downward trends in general. Moreover, CSF also induced the polyphenol in SR to release relevant monomers from its origins. Significant amount of hydrolyzable tannins were detected by mass spectrometry, including gallotannins and ellagitannins, suggesting that hydrolysis during CSF yielded gallic and ellagic acid and their derivatives, in addition to sugar moieties. Subsequently, gallic and ellagic acid can further polymerize to form sanguisorbic acid dilactone. The amount of proanthocyanidins, the oligomers of catechin, including procyanidin, procyanidin C2, procyanidin B3, and 3-O-galloylprocyanidin B3, decreased to form catechin and its derivatives, which may further degrade to protocatechualdehyde. Quantitative analysis illustrated that the amount of gallic, pyrogallic, and ellagic acid and methyl gallate, the essential effectors in SR, significantly increased after CSF, with increased ratios of 1.36, 4.28, 10.33, and 4.79, respectively. In contrast, the contents of cathechin and epigallocatechin dropped remarkably with increased ratios of 0.04 and 0.02. Tannins exhibit moderate absorption, while their relevant monomers have a higher bioavailability. Therefore, CSF is proved here to be an effective technique to the release of active monomers from the original polyphenol precursor. This study explored the mechanism by which tannins are transformed upon CSF of SR.

CAS / MDL: 970-74-1
研究领域: 药用植物学 · 分析化学 · 中药学
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NEW JOURNAL OF CHEMISTRY · 2023 · IF 3.3

Preparation and performance of xylan-based Sanguisorba officinalis L. polyphenol preservative films

Zhuorui Zhang,Yunkai Yan,Jinyang Wang,Jianxi Song,Guiquan Jiang

Xylan-based preservative films were prepared using xylan, chitosan, citric acid and Sanguisorba officinalis L. polyphenols (SOPs) as main components. According to the trend of change in the physical properties of the films, the optimal composition was found to be: 1% xylan, 0.9% chitosan, 0.26% citric acid, and 0.15% SOPs. The effects of SOP content on the films were also determined. The results showed that incorporation of SOPs decreased the TS and EAB of the film and improved the water vapor barrier performance of the film. Scanning electron microscopy, contact angle measurements and thermogravimetric analysis showed that incorporation of SOPs enhanced the compactness, hydrophobicity and thermal stability of the films. Moreover, the films exhibited excellent antibacterial activities in the presence of SOPs. Compared to the polyethylene film, the film delayed spoilage bacteria growth during refrigerated storage of pork, effectively prolonging its shelf life to at least 10 days at 4 °C. In summary, xylan-based SOP preservative films meet the requirements for food packaging materials and have good prospects for use in this field.

CAS / MDL: 9012-76-4
研究领域: 食品科学 · 材料科学 · 生物技术
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JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS · 2018 · IF 2.831

Rapid identification of urokinase plasminogen activator inhibitors from Traditional Chinese Medicines based on ultrafiltration, LC–MS and in silico docking

Li Li,Jing Kong,Chun-hua Yao,Xiu-feng Liu,Ji-hua Liu

The urokinase plasminogen activator (uPA) is regarded as the crucial trigger for plasmin generation, which is involved in several diseases especially for neoplasm metastasis. In this study, an efficient approach integrating ultrafiltration, LC/MS, bioassay and in silico docking, was proposed for rapidly detecting uPA ligands from Traditional Chinese Medicines (TCMs). Forty-two TCMs were initially assessed, and as illustrative case studies, Galla Chinensis and Sanguisorbae Radix, which appeared significant inhibitory activities on uPA, were chosen to develpe and verify the strategy. A total of seven uPA ligands were successfully detected and identified. Two of them, pentagalloylglucose and 28- O - β - d -glucopyranosyl pomolic acid, were demonstrated to be potential inhibitors, with IC 50 at 1.639 μM and 37.82 μM repectively. Furthermore, a combinatorial compound library screening combined with in silico docking assay, was revealed that ursolic acid (IC 50  = 2.623 μM) was also speculated to be a potent parent structure for inhibition of uPA. This approach offers a multidimensional perspective to discover uPA-binding leading compounds from TCMs or other complex mixtures, which would provide an efficient route for drug discovery.

CAS / MDL: 64-18-6
研究领域: 药理学 · 生物化学 · 中药学 · 药物发现
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INDUSTRIAL CROPS AND PRODUCTS · 2019 · IF 4.191

Insecticidal and antifungal activities of Rheum palmatum L. anthraquinones and structurally related compounds

Xiao-Fei Shang,Zhong-Min Zhao,Jun-Cai Li,Guan-Zhou Yang,Ying-Qian Liu,Li-Xia Dai,Zhi-Jun Zhang,Zhi-Gang Yang,Xiao-Lou Miao,Cheng-Jie Yang,Ji-Yu Zhang

As a well-known herb worldwide, rhubarb presents a wide range of pharmacological activities. In our studies, Rheum palmatum L. extracts and five isolated anthraquinones possessed insecticidal activity. The acetone extract (yield, 8.84%), which contained the highest amount of compounds (82.87 mg/g), showed stronger insecticidal activity than did the aqueous extract (yield, 37.17%) and the ethanol extract (yield, 36.92%). Notable amounts of compounds were also found in water extract residues (18.2 mg/g). Among the isolated quinones and structurally related compounds, emodin exhibited the highest insecticidal activity (LC 50  = 84.30 μg/mL) against Nilarparvata lugens ; and very moderate activity against Mythimna separata (LC 50  = 548.74 μg/mL). The LC 50 values of positive agent toosendanin against two insects were 89.34 and 418.24 μg/mL, respectively. Moreover, emodin exhibited significant AChE and GST inhibitory activities (with respective IC 50 values of 11.36 and 4.18 μg/mL). Plumbagin exhibited stronger and broader antifungal activity against eight phytopathogenic fungi (with EC 50 values ranging from 2.84 to 10.53 μg/mL) compared to a commercial fungicide, azoxystrobin (EC 50 ranging from 20.40 to >100.00 μg/mL). Plumbagin significantly damaged the cell and mitochondrial membrane systems, changed the morphology, triggered the release of cellular contents and generate reactive oxygen species in Rhizoctonia solani mycelia. This study laid the foundation for the future development of emodin and plumbagin as alternative, environmentally friendly bioinsecticide and biofungicide, respectively. Rhubarb and its residues can be used as renewable sources of anthraquinone-based products.

研究领域: 药理学 · 植物科学 · 害虫管理 · 真菌生物学
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