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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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MOLECULAR BIOLOGY REPORTS · 2025 ·Vol. 52 ·期 1 ·1-13 · IF 2.8

Monotropein inhibits MMP9-mediated cardiac oxidative stress, inflammation, matrix degradation and apoptosis in a mouse and cell line models of septic cardiac injury

Wu Wanqi,Wang Jun,Wang Guanglu,Wang Feibiao,Yang Yue,Liu Zhijun,Song Qimei,Chen Si,Chen Huizhen

Background Sepsis can cause severe cardiac damage, and matrix metalloproteinase 9 (MMP9) is involved in the inflammatory response and tissue injury processes. Monotropein is a monoterpene glycoside with anti-inflammatory and antioxidant effects. This study aims to investigate whether monotropein can alleviate sepsis-induced cardiac injury by affecting the activity of MMP9. Methods and results The correlation between MMP9 and septic cardiac injury was explored using differential expression gene analysis from the GEO database and an in vitro lipopolysaccharide (LPS)-stimulated H9c2 cell model. In a cecal ligation and puncture (CLP)-induced mouse sepsis model, the effects of monotropein on myocardial cell apoptosis, inflammatory factor expression, and antioxidant enzyme levels were validated through drug administration. The results showed that MMP9 was significantly upregulated in sepsis patients. In the H9c2 cell model, LPS-induced MMP9 activity was positively correlated with cell damage. Inhibition of MMP9 alleviates LPS-induced myocardial matrix disruption and apoptosis. Monotropein exerts anti-matrix degradation and anti-apoptotic effects through MMP9 in LPS-induced H9c2 cells. Monotropein also reduced the expression of LPS-induced inflammatory factors (TNF-α, IL-1β, IL-6).In the mouse model, monotropein decreased oxidative stress damage (lower MDA levels, increased GSH, T-AOC, CAT enzyme activity), and improved cardiac injury by inhibiting myocardial cell apoptosis-related proteins (Bax, Bcl-2, and Caspase-3 activation). Conclusion Monotropein exerts a protective effect on septic cardiac injury by inhibiting MMP9 activity, reducing inflammatory response, and enhancing antioxidant capacity, thereby ameliorating myocardial cell damage and apoptosis. Graphical abstract

CAS / MDL: 5945-50-6
研究领域: 医学 · 药理学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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RSC Advances · 2018 ·Vol. 8 ·期 5 ·2459-2468 · IF 2.936

The similarity and variability of the iridoid glycoside profile and antioxidant capacity of aerial and underground parts of Lamiophlomis rotata according to UPLC-TOF-MS and multivariate analyses

Dan Zhang,Yun-ling Gao,Sheng Jiang,Yiwen Chen,Yi Zhang,Zheng Pan

Lamiophlomis rotata (L. rotata) is a Tibetan medicinal herb used for centuries that contains iridoid glycosides (IGs), which are pharmacologically active ingredients and can be used for quality control. The IG profiles of the underground and aerial parts of the plant were determined by UPLC-TOF-MS to evaluate the similarity and variability of the different herbal parts listed in the Chinese Pharmacopoeia. Twenty-six IGs were detected in the total ion current (TIC) profile of L. rotata, and twenty-two of these were identified by comparing the retention times and mass spectra of the compounds to those of authentic standards. Among these compounds, five IGs with the same molecular formula (C17H26O11) were identified for the first time by mass spectrometry based on their different hydroxyl group-substituted positions. The aerial part has a similar chemical profile to that of the roots. The difference between the two parts was determined by multivariate statistical analysis of the UPLC-TOF-MS data of 24 specimens. Sesamoside was explored as the most characteristic marker to distinguish the two parts of L. rotata. To further estimate the distinction between the two parts, the content of total IGs and the antioxidant capacity were investigated in samples from different locations. The aerial parts showed a high content of total IGs and high antioxidant capacity, although not higher than those of the roots. The results also suggest the dosage should be increased when the aerial parts are used as crude medicinal materials instead of the underground parts.

CAS / MDL: 128-37-0 1898-66-4
研究领域: 药用植物学 · 中药化学 · 质量控制
✓ 已验证 产品关联 DOI PubMed 高影响因子
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MOLECULES · 2023 ·Vol. 28 ·期 21 ·7274 · IF 4.6

Monoterpenoid Glycosides from the Leaves of Ligustrum robustum and Their Bioactivities (II)

Shi-Hui Lu,Xiu-Xia Li,Hao-Jiang Zuo,Wei-Neng Li,Jia-Ping Pan,Jing Huang

Ligustrum robustumhas been not only used as a heat-clearing and detoxicating functional tea (Ku-Ding-Cha) but also consumed as a hypotensive, anti-diabetic, and weight-reducing folk medicine. From the leaves ofL. robustum, ten new monoterpenoid glycosides named ligurobustosides T10(1a), T11(1b), T12(2a), T13(2b), T14(3a), T15(3b), F1(4b), T16(5a), T17(5b), and E1(6b), together with five known ones (4a,6a,7,8a,8b), were separated and identified using the spectroscopic method and chemical method in this research. The results of biological tests exhibited that the fatty acid synthase (FAS) inhibitory action of compound5(IC50: 4.38 ± 0.11 μM) was as strong as orlistat (IC50: 4.46 ± 0.13 μM), a positive control; the α-glucosidase inhibitory actions of compounds1–4and7–8, and the α-amylase inhibitory actions of compounds1–8were medium; the ABTS radical scavenging capacities of compounds1–3and5–8(IC50: 6.27 ± 0.23 ~ 8.59 ± 0.09 μM) were stronger thanl-(+)-ascorbic acid (IC50: 10.06 ± 0.19 μM) served as a positive control. This research offered a theoretical foundation for the leaves ofL. robustumto prevent diabetes and its complications.Keywords:Ligustrum robustum;monoterpenoid glycoside;FAS;α-glucosidase;antioxidant;anti-diabetes

CAS / MDL: 28752-68-3
研究领域: 植物化学 · 药理学 · 天然产物研究
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JOURNAL OF SEPARATION SCIENCE · 2017 ·Vol. 40 ·期 21 ·4160-4167 · IF 2.557

Screening, separation, and evaluation of xanthine oxidase inhibitors from Paeonia lactiflora using chromatography combined with a multi-mode microplate reader

Jing Wang,Dongfang Shi,Meizhu Zheng,Bing Ma,Jing Cui,Chunming Liu,Chengyu Liu

Natural products have become one of the most important resources for discovering novel xanthine oxidase inhibitors, which are commonly employed in the treatment of hyperuricemia and gout. However, to date, few reports exist regarding the use of monoterpene glycosides as xanthine oxidase inhibitors. Thus, we herein report the use of ultrafiltration coupled with liquid chromatography in the screening of monoterpene glycoside xanthine oxidase inhibitors from the extract of Paeonia lactiflora ( P. lactiflora ), and both high-performance counter-current chromatography and medium-pressure liquid chromatography were employed to separate the main constituents. Furthermore, the xanthine oxidase inhibitory activities and the mechanisms of inhibition of the isolated compounds were evaluated using a multi-mode microplate reader by Molecular Devices. As a result, three monoterpene glycosides were separated by combined high-performance counter-current chromatography and medium-pressure liquid chromatography in purities of 90.4, 98.0, and 86.3%, as determined by liquid chromatography. These three compounds were identified as albiflorin, paeoniflorin, and 1- O -β-ᴅ-glucopyranosyl-8- O -benzoylpaeonisuffrone by electrospray ionization tandem mass spectrometry, and albiflorin and paeoniflorin were screened as potential xanthine oxidase inhibitors by ultrafiltration with liquid chromatography. The evaluation results of xanthine oxidase inhibitory activity corresponded with the screening results, as only albiflorin and paeoniflorin exhibited xanthine oxidase inhibitory activity.

CAS / MDL: 315-30-0 69-93-2 69-89-6
研究领域: 天然产物化学 · 药物化学 · 生物化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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MOLECULES · 2022 ·Vol. 27 ·期 12 ·3709 · IF 4.927

Monoterpenoid Glycosides from the Leaves of Ligustrum robustum and Their Bioactivities

Shi-Hui Lu,Jing Huang,Hao-Jiang Zuo,Zhong-Bo Zhou,Cai-Yan Yang,Zu-Liang Huang

The leaves ofLigustrum robustumhave been applied as Ku-Ding-Cha, a functional tea to clear heat, remove toxins, and treat obesity and diabetes, in Southwest China. The phytochemical research on the leaves ofL. robustumled to the isolation and identification of eight new monoterpenoid glycosides (1–8) and three known monoterpenoid glycosides (9–11). Compounds1–11were tested for the inhibitory activities on fatty acid synthase (FAS),α-glucosidase,α-amylase, and the antioxidant effects. Compound2showed stronger FAS inhibitory activity (IC50: 2.36 ± 0.10 μM) than the positive control orlistat (IC50: 4.46 ± 0.13 μM), while compounds1,2,5and11displayed more potent ABTS radical scavenging activity (IC50: 6.91 ± 0.10~9.41 ± 0.22 μM) than the positive control L-(+)-ascorbic acid (IC50: 10.06 ± 0.19 μM). This study provided a theoretical basis for the leaves ofL. robustumas a functional tea to treat obesity.Keywords:Ligustrum robustum;monoterpenoid glycoside;FAS;α-glucosidase;antioxidant;anti-obesity;hypoglycemic

CAS / MDL: 28752-68-3
研究领域: 植物化学 · 药理学 · 生物活性研究
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CHEMISTRY & BIODIVERSITY · 2022 ·Vol. 19 ·期 5 ·e202100936 · IF 2.745

Iridoid Glycosides from Phlomis Medicinalis Diels: Optimized Extraction and Hemostasis Evaluation

Sitong Lu,Zhaoyu Zhang,Youling Liang,Qingkun Zhong,Guangfa Li,Zhang Hu

Phlomis medicinalis Diels, an important perennial herbal plant unique to the Qinghai-Tibet Plateau, is often used as Tibetan Materia Medicine Radix Phlomii for the treatment of cold, cough, and convergence trauma. In order to efficiently extract the iridoid glycosides from P. medicinalis , an ultrasound-assisted deep eutectic solvent extraction technique was employed. The main parameters influencing the extraction process were studied through single-factor tests and the extraction was optimized by using response surface methodology. The hemostasis activity of total iridoid glycosides (TIG) from P. medicinalis was evaluated in vitro and in mice. The optimization results revealed that the optimal process parameters were liquid-solid ratio 20 : 1, choline chloride-lactic acid concentration 79 %, and sonication time 34 min, under which a TIG extraction yield of 20.73 % was obtained. Meanwhile, high-performance liquid chromatography-photodiode array/mass spectrometry (HPLC-PDA/MS) was employed to characterize the optimized extract and indicated that TIG from P. medicinalis mainly consisted of sixteen reported iridoid glycosides with a total content of 91.22 %. The experimental results in vivo and in vitro indicated that TIG from P. medicinalis had strong hemostasis activities, which may be achieved by increasing the fibrinogen levels. Therefore, the ultrasound-assisted deep eutectic solvent extraction is an effective method to extract iridoid glycosides from P. medicinalis and they will be promising candidates to be developed for medical hemostasis agents. Graphical

CAS / MDL: 24512-63-8
研究领域: 药用植物学 · 天然产物化学 · 药物开发
✓ 已验证 产品关联 DOI PubMed 高影响因子
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FOOD CHEMISTRY · 2024 · IF 8.5

Effect of temperature regulation on microbial community, volatile flavours, amino acid profiles, and iridoid glycosides during noni (Morinda citrifolia L.) fruit fermentation

Chao Zhang,Chunhe Gu,Mengrui Wang,Junxia Chen,Haode Chang,Ziqing Chang,Junping Zhou,Mingzhe Yue,Wenjing Zhang,Quanmiao Zhang,Zhen Feng

Noni fruit has an unpleasant flavour but is highly bioactive. Therefore, it is necessary to clarify the effect of temperature regulation on quality of fermented noni fruit. In the present study, the formation of flavours, amino acid profiles, and iridoid glycosides during noni fruit fermentation at different temperatures were investigated. We initially found that different temperatures affected core microbial communities. The general evolutionary trends of Acetobacter and Gluconobacter were influenced by different temperatures. Furthermore, high temperature helped maintain low octanoic and hexanoic acids. Subsequently, we found that high temperature improved total amino acids and iridoid glycosides. The correlation network analysis revealed that bacterial communities impacted the quality (volatile flavours, amino acid profiles, and iridoid glycosides) of fermented noni fruit. Overall, altering the temperature induced variations in microbial communities and quality during the noni fruit fermentation process. These results are instrumental in the pursuit of quality control in natural fermentation processes.

研究领域: 食品科学 · 微生物学 · 生物化学
✓ 已验证 DOI PubMed 高影响因子
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Chinese Medicine · 2024 ·Vol. 19 ·期 1 ·1-19 · IF 5.3

Total iridoid glycoside extract of Lamiophlomis rotata (Benth) Kudo accelerates diabetic wound healing by the NRF2/COX2 axis

Geng Xiaoyu,Wang Ying,Li Huan,Song Liang,Luo Chen,Gu Xiaojie,Zhong Haixin,Chen Huilin,Chen Xinzhu,Wang Jianwei,Pan Zheng

Background Lamiophlomis rotata (Benth.) Kudo ( L. rotata ), the oral Traditional Tibetan herbal medicine, is adopted for treating knife and gun wounds for a long time. As previously demonstrated, total iridoid glycoside extract of L. rotata (IGLR) induced polarization of M2 macrophage to speed up wound healing. In diabetic wounds, high levels inflammatory and chemotactic factors are usually related to high reactive oxygen species (ROS) levels. As a ROS target gene, nuclear factor erythroid 2-related factor 2 (NRF2), influences the differentiation of monocytes to M1/M2 macrophages. Fortunately, iridoid glycosides are naturally occurring active compounds that can be used as the oxygen radical scavenger. Nevertheless, the influence of IGLR in diabetic wound healing and its associated mechanism is largely unclear. Materials and methods With macrophages and dermal fibroblasts in vitro, as well as a thickness excision model of db/db mouse in vivo, the role of IGLR in diabetic wound healing and the probable mechanism of the action were investigated. Results Our results showed that IGLR suppressed oxidative distress and inflammation partly through the NRF2/cyclooxygenase2 (COX2) signaling pathway in vitro . The intercellular communication between macrophages and dermal fibroblasts was investigated by the conditioned medium (CM) of IGLR treatment cells. The CM increased the transcription and translation of collagen I (COL1A1) and alpha smooth muscle actin (α-SMA) within fibroblasts. With diabetic wound mice, the data demonstrated IGLR activated the NRF2/KEAP1 signaling and the downstream targets of the pathway, inhibited COX2/PEG2 signaling and decreased the interaction inflammatory targets of the axis, like interleukin-1beta (IL-1β), interleukin 6 (IL-6), apoptosis-associated speck-like protein (ASC), cysteinyl aspartate specific proteinase1 (caspase1) and NOD-like receptor-containing protein 3 (NLRP3).In addition, the deposition of COL1A1, and the level of α-SMA, and Transforming growth factor-β1 (TGF-β1) obviously elevated, whereas that of pro-inflammatory factors reduced in the diabetic wound tissue with IGLR treatment. Conclusion IGLR suppressed oxidative distress and inflammation mainly through NRF2/COX2 axis, thus promoting paracrine and accelerating wound healing in diabetes mice. Graphical Abstract

CAS / MDL: 93572-42-0
研究领域: 药理学 · 分子生物学 · 传统医学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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Arabian Journal of Chemistry · 2021 · IF 5.165

Ultrasound-assisted extraction of four groups of Osmanthus fragrans fruit: Optimization, UPLC-Orbitrap-MS/MS characterization and anti-inflammatory activity evaluation

Weizhuo Tang,Shuang Li,Miaomiao Wang,Bin Wang

In this study, simultaneous optimization of ultrasound-assistant extraction (UAE) of four representative groups of Osmanthus fragrans (OF) fruit was firstly performed using the response surface methodology (RSM). Subsequently, qualitative and quantitative analysis of irioid glycosides from the optimized OF fruit extract was performed using UPLC-ESI-Orbitrap-MS/MS. A total of 13 irioid glycosides were tentatively identified, of which six compounds were identified for the first time. Finally, the anti-inflammatory activity of the optimized OF var. aurantiacus Makino (OFA) fruit extract was evaluated based on a CuSO 4 -induced zebra fish model. The biological results demonstrated that OFA fruit extract at a concentration of 5 μg/mL could significantly reduce the number of macrophages, but no significant activities were observed at high concentrations (10 and 50 μg/mL). These results suggest that OF fruit has the promise as a functional additive in food for health promotion.

CAS / MDL: 7664-38-2
研究领域: 药理学 · 分析化学 · 食品科学
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FITOTERAPIA · 2019 · IF 2.431

Pharmacokinetic of gastrodigenin rhamnopyranoside from Moringa seeds in rodents

Wenjing Li,Congyong Sun,Wenwen Deng,Yingkun Liu,Michael Adu-Frimpong,Jiangnan Yu,Ximing Xu

Gastrodigenin rhamnopyranoside (GR) is a hepatoprotective compound that exists in Moringa oleifera seeds. However, the UPLC-MS/MS method for the determination of GR ( in-vitro / in-vivo ) is lacking clarification. Herein, this study established the UPLC-MS/MS technique, which was effective and sensitive for the investigation of the pharmacokinetics and biodistribution of GR in rats and mice. The separation was achieved with a Shim-pack XR-ODS III C 18 column (2.0 × 75 mm, 1.6 μm) at 40 °C, while the mobile phase (Acetonitrile/0.1% Formic acid =12:82, v /v) was at an eluting rate of 0.2 mL/min. The Multiple Reaction Monitoring (MRM) was selected for quantification, i.e. , m / z [M + HCOO] − 314.9 → 269 for GR and m/z [M + HCOO] - 182.85 → 137 for Tyrosol as the internal standard. The calibration curves were linearly ranged from 10 to 2500 ng/mL ( r  ≥ 0.999) with a lower-limit-of-quantification (LLOQ) of 10 ng/mL in the various biological samples (plasma, liver, heart, lung, spleen, brain, kidney). The intra- and inter-day precision was within 5%, while accuracy ranged from −11.4% - 8.33%. Recovery and matrix effect were with 80.32 to 101.31% and 90.36 to 103.76%, respectively, in a reasonable range. After oral and intravenous administration, GR was detected within 3 h but decreased rapidly in plasma, indicating fast elimination. Also, GR was quickly distributed in the various tissues, particularly in the kidney and spleen. The results demonstrated that the established UPLC-MS/MS method was highly linear, precise and accurate with the potential to be used for the quantitative analysis of GR in-vivo .

研究领域: 药理学 · 分析化学 · 生物医学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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JOURNAL OF CHROMATOGRAPHY A · 2017 · IF 3.981

Water-compatible micron-sized monodisperse molecularly imprinted beads for selective extraction of five iridoid glycosides from Cornus officinalis fructus

Wenhua Ji,Tao Wang,Wei Liu,Feng Liu,Lanping Guo,Yanling Geng,Xiao Wang

An efficient, accurate and sensitive method for the determination of five iridoid glycosides (IGs) in Cornus officinalis fructus using molecularly imprinted solid phase extraction (MISPE) coupled with high performance liquid chromatography (HPLC) has been developed. Water-compatible molecularly imprinted beads (MIBs) were synthesized by precipitation polymerization, using alkenyl glycosides glucose as the hydrophilic functional monomer. Scanning electron microscopy showed that the MIBs had a narrow particle size distribution, with diameters in the range 7.5–9.3   μm. The special molecular recognition by the MIBs of IGs in aqueous media was verified by static adsorption, kinetic adsorption, and selectivity experiments. The newly prepared MIBs were used as sorbents in solid phase extraction (SPE) for the selective recognition of five IGs (loganin, morroniside, loganic acid, 7- O -ethyl-morroniside and 7- O -methyl morroniside) in Cornus officinalis fructus. When optimized, the MISPE-HPLC method had good linearity (0.02–100   mg   g −1 ), with correlation coefficient ( R )   ≥   0.994. Recoveries at three spiked levels were in the range 80.0%–94.0%. Because of its excellent specificity and hydrophilicity, SPE based on monodisperse MIBs provides a promising pretreatment strategy for the analysis of active components in natural products, especially for the quality control of traditional Chinese medicines.

CAS / MDL: 78-67-1 110-26-9
研究领域: 分析化学 · 药学 · 中药学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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