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Pinoresinol Diglucoside
SEPARATION SCIENCE AND TECHNOLOGY · 2021 · IF 2.475

Preparation of a pinoresinol diglucoside imprinted polymer using metal organic frame as the matrix for extracting target compound from Eucommia ulmoides

Tian Haixi,Hui Li,Mao Lin,Li Kegang

Fabrication of a post-synthesis imprint modification method for metal-organic frameworks in order to improve its selectivity in the field of separation and analysis is of great interest. For this purpose, a pinoresinol diglucoside (PDG) imprinted polymer was attempted to graft on the surface of metal-organic frameworks MIL-101 to produce a new composite material named MIPs@ED-MIL-101. This modification procedure was monitored by using X-Ray Diffraction, fourier transforms infrared spectroscopy and scanning electron microscopy in the crystal structure, chemical groups and particles topography, respectively. Adsorption kinetics and thermodynamics behavior, rebinding selectivity and applicability in solid-phase extraction for this new material obtained were evaluated. The kinetics test indicated this composite material improved adsorption dynamics relative to the MIL-101, with a 28.6% decrease in adsorption equilibrium time. The adsorption capacity for the MIPs@ED-MIL-101 toward PDG was shown higher than that for the MIL-101 and nonimprint-modified material NIPs@ED-MIL-101 at the same substrate concentration when adsorption was carried out at 298 K in acetonitrile-H2O mixed solution (1:1, V/V). Freundlich model can best fit the isotherm data for the MIPs@ED-MIL-101, indicating site heterogeneity in this composite material and mean adsorption energy of 19.60 kJ mol-1 obtained by Dubinin–Radushkevich model fitting might imply chemical adsorption the main rebinding process. In addition, this imprint composite material could selectively bind template and be utilized as the adsorbent in solid-phase extraction to capture target compound from plant crude extract. This new material can also be reused many times with a slight decrease in adsorption capacity.

研究领域: 材料科学 · 分析化学 · 植物化学
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Frontiers in Pharmacology · 2021 · IF 5.811

Comparison of Pinoresinol and its Diglucoside on their ADME Properties and Vasorelaxant Effects on Phenylephrine-Induced Model

Pu Yiqiong,Cai Yiqing,Zhang Qi,Hou Tianling,Zhang Teng,Zhang Tong,Wang Bing

Pinoresinol (PINL) and pinoresinol diglucoside (PDG), two natural lignans found in Eucommia ulmoides Oliv. (Duzhong), have several pharmacological activities. However, there is no report available on their absorption, distribution, metabolism, and elimination (ADME) properties. Given the possible wide spectrum of their application in therapeutic areas, this area should be investigated. This work studied the in vitro ADME properties of PDG and PINL, including their kinetic solubility, permeability across monolayer cells (PAMPA), protein binding, and metabolic stabilities in liver microsomes. The in vivo pharmacokinetic study and in vitro vasorelaxant effects on isolated phenylephrine-induced aortic rings of PINL and PDG were also investigated. It was found that both of their kinetic solubility in PBS (pH 7.4) was greater than 100 μM, indicating that they are both soluble compounds. The permeability investigations (Peff) by PAMPA indicated that PINL had higher permeability than PDG (p < 0.05). Both components represented moderate plasma protein binding activities (average binding rate in human plasma: PINL 89.03%, PDG 45.21%) and low metabolic rate (t1/2 in human liver microsome: PINL 1509.5 min, PDG 1004.8 min). Furthermore, the results of pharmacokinetic studies indicated that PINL might be eliminated less quickly than PDG from the rat plasma, and its cumulative urinary excretion was much lower than that of PDG. The phenylephrine-induced aortic rings demonstrated concentration-dependent vasorelaxation in PDG, PINL, or their combination group. The vasorelaxant effects of PINL were more obvious than those of PDG, whereas the vasorelaxant effect of the combinations was significantly better than that of the single component (p < 0.05). The similarity or difference between PINL and its diglucoside in these pharmaceutical aspects may offer valuable insights into the further exploration of lignans and might contribute to relevant studies involving natural products with similar molecular structure and their glucosides.

研究领域: 药理学 · 天然产物化学 · 药物代谢动力学
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TOXICOLOGY AND APPLIED PHARMACOLOGY · 2024 · IF 3.3

Pinoresinol diglucoside mitigates dexamethasone-induced osteoporosis and chondrodysplasia in zebrafish

Yuhua Zuo,Chao Chen,Fasheng Liu,Hongmei Hu,Si Dong,Qinyuan Shen,Junquan Zeng,Ling Huang,Xinjun Liao,Zigang Cao,Zilin Zhong,Huiqiang Lu,Jianjun Chen

Background The global increase in the aging population has led to a higher incidence of osteoporosis among the elderly. Objective This study aimed to evaluate the protective properties of pinoresinol diglucoside (PDG), an active constituent of Eucommia ulmoides , against dexamethasone-induced osteoporosis and chondrodysplasia. Methods A zebrafish model of osteoporosis was established by exposing larval zebrafish to dexamethasone. The impact of PDG on bone mineralization was assessed through alizarin red and calcein staining. Alkaline phosphatase activity was quantified to evaluate osteoblast function. The influence of PDG on chondrogenesis was estimated using alcian blue staining. Fluorescence imaging and motor behavior analysis were employed to assess the protective effect of PDG on the structure and function of dexamethasone-induced skeletal teratogenesis. qPCR determined the expression of osteogenesis and Wnt signaling-related genes. Molecular docking was used to assess the potential interactions between PDG and Wnt receptors. Results PDG significantly increased bone mineralization and corrected spinal curvature and cartilage malformations in the zebrafish model. Furthermore, PDG enhanced swimming abilities compared to the model group. PDG mitigated dexamethasone-induced skeletal abnormalities in zebrafish by upregulating Wnt signaling, showing potential interaction with Wnt receptors FZD2 and FZD5. Conclusion PDG mitigates dexamethasone-induced osteoporosis and chondrodysplasia by promoting bone formation and activating Wnt signaling.

CAS / MDL: 63902-38-5
研究领域: 药理学 · 生物学 · 医学 · 动物学 · 分子生物学
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Life Sciences in Space Research · 2025 · IF 2.8

Pinoresinol diglucoside alleviates hindlimb unloading-induced bone loss in mice

Ying-Ying Xuan,Liang Li,Yi Wu,Zhen-Long Wei,Mei Zhang,Min-Na Liu,Dong-Shuai Shen,Yu-Hai Gao,Cory J Xian,Hui-Ping Ma,Ke-Ming Chen

Microgravity-induced bone loss has long been a critical issue in space exploration. While countermeasures have been suggested, none have achieved the desired effects. Pinoresinol diglucoside (PDG), an effective constituent of the medicinal herb Eucommia ulmoidis Oliv, was reported to increase peak bone mass in growing rats and mitigate dexamethasone-induced osteoporosis. However, it is unknown if it affects microgravity-induced bone loss. Here, PDG effects were investigated in cultured rat calvarial osteoblasts exposed to simulated microgravity (SMG) and in hindlimb-unloaded mice. PDG (1 × 10 6 mol/L) prevented SMG-induced osteoblast osteogenesis reduction and oxidative stress (increased levels of oxidative markers and decreased activities of antioxidant enzymes). It alleviated cell proliferation suppression, apoptosis and cell cycle arrest. In hindlimb-suspended mice orally administrated with PDG for 21 days, unloading-induced reduction of femoral bone mineral density, deterioration of bone microstructure and strength, and reduction of osteogenic potential of bone marrow stromal cells were significantly reversed at three dosages tested. It alleviated unloading-induced bone loss (decreased serum bone formation marker but increased resorption marker levels), osteocyte apoptosis (changes in TUNEL staining and apoptosis marker expression), oxidative damages (increased serum 8-iso-PGF2α and 8-OHdG levels), inflammation (increased serum inflammatory cytokine levels), and increased bone resorption signal (bone and serum RANKL/OPG expression ratio). These results demonstrated that PDG effectively counteracted hindlimb unloading-induced bone loss by inhibiting osteocyte apoptosis, preventing oxidative stress and inflammation, preserving bone formation and inhibiting resorption. PDG is a good candidate to be further tested for its potential use in preventing spaceflight-induced bone loss and disuse osteoporosis.

CAS / MDL: 67-68-5
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PLoS One · 2015 ·Vol. 10 ·期 9 ·e0137066 · IF 3.234

Bioconversion of Pinoresinol Diglucoside and Pinoresinol from Substrates in the Phenylpropanoid Pathway by Resting Cells of Phomopsis sp.XP-8

Yan Zhang,Junling Shi,Laping Liu,Zhenhong Gao,Jinxin Che,Dongyan Shao,Yanlin Liu

Pinoresinol diglucoside (PDG) and pinoresinol (Pin) are normally produced by plant cells via the phenylpropanoid pathway. This study reveals the existence of a related pathway in Phomopsis sp. XP-8, a PDG-producing fungal strain isolated from the bark of the Tu-chung tree ( Eucommiaulmoides Oliv.). After addition of 0.15 g/L glucose to Phomopsis sp. XP-8, PDG and Pin formed when phenylalanine, tyrosine, leucine, cinnamic acid, and p -coumaric acid were used as the substrates respectively. No PDG formed in the absence of glucose, but Pin was detected after addition of all these substrates except leucine. In all systems in the presence of glucose, production of PDG and/or Pin and the accumulation of phenylalanine, cinnamic acid, or p -coumaric acid correlated directly with added substrate in a time- and substrate concentration- dependent manner. After analysis of products produced after addition of each substrate, the mass flow sequence for PDG and Pin biosynthesis was defined as: glucose to phenylalanine, phenylalanine to cinnamic acid, then to p -coumaric acid, and finally to Pin or PDG. During the bioconversion, the activities of four key enzymes in the phenylpropanoid pathway were also determined and correlated with accumulation of their corresponding products. PDG production by Phomopsis sp. exhibits greater efficiency and cost effectiveness than the currently-used plant-based system and will pave the way for large scale production of PDG and/or Pin for medical applications.

研究领域: 微生物学 · 生物化学 · 药理学
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APPLIED MICROBIOLOGY AND BIOTECHNOLOGY · 2015 ·Vol. 99 ·期 11 ·4629-4643 · IF 3.337

Production of pinoresinol diglucoside, pinoresinol monoglucoside, and pinoresinol by Phomopsis sp. XP-8 using mung bean and its major components

Zhang Yan,Shi Junling,Gao Zhenhong,Yangwu Ruiming,Jiang Huanshi,Che Jinxin,Liu Yanlin

Phomopsis sp. XP-8 is an endophytic fungus that has the ability to produce pinoresinol diglucoside (PDG) in vitro and thus has potential application for the biosynthesis of PDG independent of plants. When cultivated in mung bean medium, PDG production was significantly improved and pinoresinol monoglucoside (PMG) and pinoresinol (Pin) were also found in the culture medium. In this experiment, starch, protein, and polysaccharides were isolated from mung beans and separately used as the sole substrate in order to explore the mechanism of fermentation and identify the major substrates that attributed to the biotransformation of PDG, PMG, and Pin. The production of PDG, PMG, and Pin was monitored using high-performance liquid chromatography (HPLC) and confirmed using HPLC-MS. Activities of related enzymes, including phenylalanine ammonia-lyase (PAL), trans-cinnamate 4-hydroxylase (C4H), and 4-coumarate-CoA ligase (4CL) were analyzed and tracked during the cultivation. The reaction system contained the compounds isolated from mung bean in the designed amount. Accumulation of phenylalanine, cinnamic acid, p-coumaric acid, PDG, PMG, and Pin and the activities of PAL, C4H, and 4CL were measured during the bioconversion. PMG was found only when mung bean polysaccharide was analyzed, while production of PDG and Pin were found when both polysaccharide and starch were analyzed. After examining the monosaccharide composition of the mung bean polysaccharide and the effect of the different monosaccharides had on the production of PMG, PDG, and Pin, galactose in mung bean polysaccharide proved to be the major factor that stimulates the production of PMG.

研究领域: 微生物学 · 生物化学 · 天然产物化学
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