Pinosylvin
(Synonyms: 赤松素) 目录号 : GC40861
A stilbene with diverse biological activities
Cas No.:22139-77-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Pinosylvin is a stilbene originally isolated from pine heartwood that has diverse biological activities. It activates sirtuin 1 (SIRT1) and induces glucose uptake in isolated rat L6 skeletal muscle myotubes. Pinosylvin reduces radial growth in a panel of 28 plant pathogenic fungi when used at a concentration of 100 μg/ml. It reduces expression of matrix metalloproteinase-2 (MMP-2), MMP-9, and membrane type 1-MMP in and inhibits migration of HT-1080 cells. Pinosylvin (10 mg/kg, i.p.) reduces the number of tumor nodules and lung tumor weight in a CT26 mouse xenograft model of metastatic colon cancer. It decreases hind paw volume and myeloperoxidase (MPO) activity in a rat model of adjuvant-induced arthritis. Pinosylvin also exhibits plant antifeedant activity against L. americanus (snowshoe hares).
| Cas No. | 22139-77-1 | SDF | |
| 别名 | 赤松素 | ||
| Canonical SMILES | OC1=CC(/C=C/C2=CC=CC=C2)=CC(O)=C1 | ||
| 分子式 | C14H12O2 | 分子量 | 212.2 |
| 溶解度 | DMF: 10mg/mL,DMF:PBS (pH 7.2) (1:50): 0.01mg/mL,DMSO: 10mg/mL,Ethanol: 20mg/mL,Ethanol:PBS (pH 7.2) (1:50): 0.01mg/mL | 储存条件 | 4°C, protect from light |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 4.7125 mL | 23.5627 mL | 47.1254 mL |
| 5 mM | 0.9425 mL | 4.7125 mL | 9.4251 mL |
| 10 mM | 0.4713 mL | 2.3563 mL | 4.7125 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Natural Sources and Pharmacological Properties of Pinosylvin
Plants (Basel) 2022 Jun 9;11(12):1541.PMID:35736692DOI:10.3390/plants11121541.
Pinosylvin (3,5-dihydroxy-trans-stilbene), a natural pre-infectious stilbenoid toxin, is a terpenoid polyphenol compound principally found in the Vitaceae family in the heartwood of Pinus spp. (e.g., Pinus sylvestris) and in pine leaf (Pinus densiflora). It provides defense mechanisms against pathogens and insects for many plants. Stilbenoids are mostly found in berries and fruits but can also be found in other types of plants, such as mosses and ferns. This review outlined prior research on Pinosylvin, including its sources, the technologies used for its extraction, purification, identification, and characterization, its biological and pharmacological properties, and its toxicity. The collected data on Pinosylvin was managed using different scientific research databases such as PubMed, SciFinder, SpringerLink, ScienceDirect, Wiley Online, Google Scholar, Web of Science, and Scopus. In this study, the findings focused on Pinosylvin to understand its pharmacological and biological activities as well as its chemical characterization to explore its potential therapeutic approaches for the development of novel drugs. This analysis demonstrated that Pinosylvin has beneficial effects for various therapeutic purposes such as antifungal, antibacterial, anticancer, anti-inflammatory, antioxidant, neuroprotective, anti-allergic, and other biological functions. It has shown numerous and diverse actions through its ability to block, interfere, and/or stimulate the major cellular targets responsible for several disorders.
Pinosylvin Shifts Macrophage Polarization to Support Resolution of Inflammation
Molecules 2021 May 8;26(9):2772.PMID:34066748DOI:10.3390/molecules26092772.
Pinosylvin is a natural stilbenoid found particularly in Scots pine. Stilbenoids are a group of phenolic compounds identified as protective agents against pathogens for many plants. Stilbenoids also possess health-promoting properties in humans; for instance, they are anti-inflammatory through their suppressing action on proinflammatory M1-type macrophage activation. Macrophages respond to environmental changes by polarizing towards proinflammatory M1 phenotype in infection and inflammatory diseases, or towards anti-inflammatory M2 phenotype, mediating resolution of inflammation and repair. In the present study, we investigated the effects of Pinosylvin on M2-type macrophage activation, aiming to test the hypothesis that Pinosylvin could polarize macrophages from M1 to M2 phenotype to support resolution of inflammation. We used lipopolysaccharide (LPS) to induce M1 phenotype and interleukin-4 (IL-4) to induce M2 phenotype in J774 murine and U937 human macrophages, and we measured expression of M1 and M2-markers. Interestingly, along with inhibiting the expression of M1-type markers, Pinosylvin had an enhancing effect on the M2-type activation, shown as an increased expression of arginase-1 (Arg-1) and mannose receptor C type 1 (MRC1) in murine macrophages, and C-C motif chemokine ligands 17 and 26 (CCL17 and CCL26) in human macrophages. In IL-4-treated macrophages, Pinosylvin enhanced PPAR-γ expression but had no effect on STAT6 phosphorylation. The results show, for the first time, that Pinosylvin shifts macrophage polarization from the pro-inflammatory M1 phenotype towards M2 phenotype, supporting resolution of inflammation and repair.
Pinosylvin exacerbates LPS-induced apoptosis via ALOX 15 upregulation in leukocytes
BMB Rep 2018 Jun;51(6):302-307.PMID:29555013DOI:10.5483/bmbrep.2018.51.6.024.
Pinosylvin is known to have anti-inflammatory activity in endothelial cells. In this study, we found that Pinosylvin had a pro-apoptotic activity in lipopolysaccharide (LPS)-preconditioned leukocytes. This finding suggests that Pinosylvin has an effect on the resolution of inflammation. To understand the detailed mechanism, we examined if Pinosylvin enhances cyclooxygenase (COX) or lipoxygenase (LOX) activity in THP-1 and U937 cells. LOX activity was found to be markedly increased by Pinosylvin, whereas COX activity was not altered. Furthermore, we found that Pinosylvin enhanced both levels of ALOX 15 mRNA and protein, implying that LOX activity, elevated by Pinosylvin, is attributed to upregulation of ALOX 15 expression. From this cell signaling study, Pinosylvin appeared to promote phosphorylations of ERK and JNK. ERK or JNK inhibitors were found to attenuate ALOX 15 expression and LPS-induced apoptosis promoted by Pinosylvin. In conclusion, Pinosylvin enhances the apoptosis of LPSpreconditioned leukocytes by up-regulating ALOX 15 expression through ERK and JNK. These findings suggest that Pinosylvin may induce the resolution of inflammation. [BMB Reports 2018; 51(6): 302-307].
Pinosylvin enhances leukemia cell death via down-regulation of AMPKα expression
Phytother Res 2018 Oct;32(10):2097-2104.PMID:30027566DOI:10.1002/ptr.6156.
Resveratrol at high concentrations (50-100 μmol/L) is known to induce cell death in leukemia cells. Here, we investigated whether Pinosylvin, a resveratrol analogue, induced cell death in leukemia cells. Cell death was found to be markedly elevated by 50- to 100-μmol/L Pinosylvin in THP-1 and U937 cells. It was also shown that Pinosylvin induced caspase-3 activation, flip-flop of phosphatidylserine, LC3-II accumulation, LC3 puncta, and p62 degradation in both THP-1 and U937 cells. These data indicate that pinosylvin-induced cell death may occur through apoptosis and autophagy. In addition, we showed that Pinosylvin down-regulates AMP-activated protein kinase α1 (AMPKα1) in leukemia cells. Therefore, we correlated AMPKα1 down-regulation and leukemia cell death. AMPKα1 inhibition appeared to decrease pinosylvin-induced apoptosis and autophagy in leukemia cells, implying that AMPK is a key regulator of leukemia cell death. Moreover, we found that both pinosylvin-induced autophagy and apoptotic progress were reduced in AMPKα1-overexpressed leukemia cells, when compared with vector-transfected cells. Cell death was elevated by AMPKα1 overexpression, whereas pinosylvin-induced cell death was markedly decreased by caspase-3 inhibitors or autophagy inhibitors. These results suggest that pinosylvin-induced depletion of AMPKα1 enhances cell death via apoptosis and autophagy in leukemia cells.
Efficient biosynthesis of Pinosylvin from lignin-derived cinnamic acid by metabolic engineering of Escherichia coli
Biotechnol Biofuels Bioprod 2022 Dec 12;15(1):136.PMID:36503554DOI:10.1186/s13068-022-02236-5.
Background: The conversion of lignin-derived aromatic monomers into valuable chemicals has promising potential to improve the economic competitiveness of biomass biorefineries. Pinosylvin is an attractive pharmaceutical with multiple promising biological activities. Results: Herein, Escherichia coli was engineered to convert the lignin-derived standard model monomer cinnamic acid into Pinosylvin by introducing two novel enzymes from the wood plant: stilbene synthase from Pinus pinea (PpSTS) and 4-Coumarate-CoA ligase from Populus trichocarpa (Ptr4CL4). The expression of Ptr4CL4 drastically improved the production of Pinosylvin (42.5 ± 1.1 mg/L), achieving values 15.7-fold higher than that of Ptr4CL5 (another 4-Coumarate-CoA ligase from Populus trichocarpa) in the absence of cerulenin. By adjusting the expression strategy, the optimized engineered strain produced Pinosylvin at 153.7 ± 2.2 mg/L with an extremely high yield of 1.20 ± 0.02 mg/mg cinnamic acid in the presence of cerulenin, which is 83.9% ± 1.17 of the theoretical yield. This is the highest reported Pinosylvin yield directly from cinnamic acid to date. Conclusion: Our work highlights the feasibility of microbial production of Pinosylvin from cinnamic acid and paves the way for converting lignin-related aromatics to valuable chemicals.