Secoisolariciresinol diglucoside (SDG)
(Synonyms: (R,R)-亚麻木酚素; (R,R)-SDG; (R,R)-LGM2605) 目录号 : GC34020
A lignan with diverse biological activities
Cas No.:158932-33-3
Sample solution is provided at 25 µL, 10mM.
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- Purity: >99.00%
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Secoisolariciresinol diglucoside (SDG) is a lignan that has been found in flaxseed with antioxidant, antiproliferative, antidiabetic, and cardioprotective biological activities.1,2,3,4,5,6 It scavenges 2,2-diphenyl-1-picrylhydrazyl radicals (IC50 = 78.9 μg/ml) in a cell-free assay and dose-dependently inhibits the growth of SW480 human colon cancer cells in vitro.2,3 Dietary administration of SDG reduces the number of proliferating tumor cells in an MCF-7 human breast cancer mouse xenograft model in the presence of circulating estrogen.4 It also increases insulin and decreases glucose serum levels in rats with diabetes induced by streptozotocin when administered at a dose of 20 mg/kg.5 SDG (20 mg/kg per day) decreases infarct size in rats with myocardial infarction induced by permanent occlusion of the left anterior descending coronary artery.6
1.Imran, M., Ahmad, N., Anjum, F.M., et al.Potential protective properties of flax lignan secoisolariciresinol diglucosideNutr. J.14:71(2015) 2.Moree, S.S., and Rajesha, J.Investigation of in vitro and in vivo antioxidant potential of secoisolariciresinol diglucosideMol. Cell Biochem.373(1-2)179-187(2013) 3.Ayella, A., Lim, S., Jiang, Y., et al.Cytostatic inhibition of cancer cell growth by lignan secoisolariciresinol diglucosideNutr. Res.30(11)762-769(2010) 4.Truan, J.S., Chen, J.-M., and Thompson, L.U.Comparative effects of sesame seed lignan and flaxseed lignan in reducing the growth of human breast tumors (MCF-7) at high levels of circulating estrogen in athymic miceNutr. Cancer64(1)65-71(2012) 5.Moree, S.S., Kavishankar, G.B., and Rajesha, J.Antidiabetic effect of secoisolariciresinol diglucoside in streptozotocin-induced diabetic ratsPhytomedicine20(3-4)237-245(2013) 6.Penumathsa, S.V., Koneru, S., Zhan, L., et al.Secoisolariciresinol diglucoside induces neovascularization-mediated cardioprotection against ischemia-reperfusion injury in hypercholesterolemic myocardiumJ. Mol. Cell. Cardiol.44(1)170-179(2008)
| Cas No. | 158932-33-3 | SDF | |
| 别名 | (R,R)-亚麻木酚素; (R,R)-SDG; (R,R)-LGM2605 | ||
| Canonical SMILES | COC1=C(O)C=CC(C[C@@H](CO[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)CO)[C@@](CO[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)CO)([H])CC4=CC(OC)=C(O)C=C4)=C1 | ||
| 分子式 | C32H46O16 | 分子量 | 686.7 |
| 溶解度 | Water : ≥ 100 mg/mL (145.62 mM) | 储存条件 | Store at -20°C |
| 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 | 1.4562 mL | 7.2812 mL | 14.5624 mL |
| 5 mM | 0.2912 mL | 1.4562 mL | 2.9125 mL |
| 10 mM | 0.1456 mL | 0.7281 mL | 1.4562 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。
Secoisolariciresinol Diglucoside of Flaxseed and Its Metabolites: Biosynthesis and Potential for Nutraceuticals
Front Genet 2018 Dec 12;9:641.PMID:30619466DOI:10.3389/fgene.2018.00641.
Secoisolariciresinol diglucoside (SDG), found mainly in flaxseed, is one of the essential lignans. SDG, as well as the beneficial fatty acid composition and high fiber content, has made flaxseed an important source of functional food or nutraceutical ingredients. Various studies have shown that SDG offers several health benefits, including protective effects against cardiovascular diseases, diabetes, cancer, and mental stress. These health benefits have been attributed to the antioxidant properties of SDG. Additionally, SDG metabolites, namely mammalian lignans, enterodiol and enterolactone, have shown promising effects against cancer. Therefore, understanding the biosynthetic pathway of SDG and its molecular mechanisms is a key to enable the production of new flaxseed cultivars rich in nutraceutical content. The present review highlights studies on the different health benefits of SDG, as well as lignan biosynthesis in flaxseed and genes involved in the biosynthetic pathway. Since SDG, the predominant lignan in flaxseed, is a glycosylated lignan, we also focus on studies investigating the genes involved in secoisolariciresinol glycosylation. These genes can be used to produce new cultivars with a novel level of glycosylation or lignan composition to maximize the yields of lignans with a therapeutic or protective potential.
Secoisolariciresinol diglucoside (SDG) Isolated from Flaxseed, an Alternative to ACE Inhibitors in the Treatment of Hypertension
Int J Angiol 2013 Dec;22(4):235-8.PMID:24436618DOI:10.1055/s-0033-1351687.
Secoisolariciresionol diglucoside (SDG) is a plant lignan isolated from flaxseed and is phytoestrogen. SDG is a potent and long-acting hypotensive agent. Plant phytoestrogens have inhibitory effects on angiotensin-converting enzyme (ACE). The hypotensive effects of SDG, a phytoestrogen, may be mediated through inhibition of ACE. The objective of this study was to investigate if SDG-induced hypotension is mediated through inhibition of ACE. The Sprague Dawley male rats were anesthetized and trachea was cannulated. The right jugular vein was cannulated to administer the drug and the carotid artery was cannulated to record arterial pressures using PIOEZ-1 miniature model transducer (Becton, Dickinson and Company, Franklin Lakes, NJ) and Beckman dynograph (Beckman Instruments, Inc., Schiller Park, IL). The effects of angiotensin I (0.2 µg/kg, intravenously [IV]) in the absence and presence of SDG (10 mg/kg, IV), and SDG alone on systolic, diastolic, and mean arterial pressures were measured before and after 15, 30, and 60 minutes of drug administration. SDG decreased the systolic, diastolic, and mean arterial pressure by 37, 47, and 43%, respectively, at 15 minutes and 18.8, 21.2, and 20.3%, respectively, at 60 minutes. Angiotensin I increased the arterial pressure. SDG decreased angiotensin I-induced rise in the systolic, diastolic, and mean arterial pressures by 60, 58, and 51%, respectively, at 15 minutes and 48, 46, and 30%, respectively, at 60 minutes. The data suggest that SDG reduced the angiotensin I-induced rise in the arterial pressures and hence SDG is a potent ACE inhibitor.
Secoisolariciresinol Diglucoside Improves Ovarian Reserve in Aging Mouse by Inhibiting Oxidative Stress
Front Mol Biosci 2022 Jan 4;8:806412.PMID:35059437DOI:10.3389/fmolb.2021.806412.
Ovarian reserve is a key factor in the reproductive function of the ovaries. Ovarian aging is characterized by a gradual decline in the quantity and quality of follicles. The underlying mechanism of ovarian aging is complex and age-related oxidative stress is considered one of the most likely factors. Secoisolariciresinol diglucoside (SDG) has been shown to have good scavenging ability against reactive oxygen species (ROS) which slowly accumulates in ovarian tissues. However, it is unknown whether SDG had beneficial effects on aging ovaries. In this study, we used 37-week-old female C57BL/6J mouse as a natural reproductive aging model to evaluate the role of SDG in ovarian aging. SDG (7 and 70 mg/kg) intragastric administration was performed in the mice daily. After 8 weeks, the effects of SDG on aging ovaries were evaluated by counting the number of follicles and the expression of follicle-stimulating hormone receptors (FSHR) in the ovary. The mechanism of SDG on the aging ovaries was further explored through ovarian metabolomics. It was found that SDG can effectively increase the number of growing follicles and increase the expression of the FSHR protein. The metabolomics results showed that the ovaries in the SDG intervention group achieved better uptake and transport of nutrients, including amino acids and glucose that are necessary for the development of oocytes. At the same time, the ovaries of the SDG intervention group showed that the drug reduced ROS generation. Additionally, we found that ovarian telomere length and ovarian mitochondrial DNA copy number that are highly susceptible to ROS damage and are also related to aging. The results showed that SDG can significantly increase mitochondrial DNA copy number and slow down the process of telomere shortening. These data indicate that SDG improves ovarian reserve by inhibiting oxidative stress.
Secoisolariciresinol diglucoside induces pyroptosis by activating caspase-1 to cleave GSDMD in colorectal cancer cells
Drug Dev Res 2022 Aug;83(5):1152-1166.PMID:35472101DOI:10.1002/ddr.21939.
Secoisolariciresinol diglucoside (SDG) is the main component of lignans with various biological activities, including anticancer activity. However, whether SDG has obvious anticancer effects on colorectal cancer (CRC) is unclear. Pyroptosis, a form of programmed cell death, has received increasing attention in cancer-related research. In this study, we aimed to test the anticancer properties and relatecd functional mechanisms of SDG. we found that SDG not only inhibited the cell viability of HCT116 cells, but also induced HCT116 cells to swell with apparent large bubbles, which are typical signs of pyroptosis. Furthermore, SDG induced cell pyroptosis by enhancing cleavage of the N-terminal fragment of gasdermin D (GSDMD) in CRC cells, accompanied by increased caspase-1 cleavage. Consistent with this, SDG-induced GSDMD-N-terminal fragment cleavage and pyroptosis were reduced by siRNA-mediated silencing of caspase-1 or treatment with the specific caspase-1 inhibitor VX-765 treatment, suggesting that active caspase-1 further induces pyroptosis. A mechanistic study showed that SDG induced reactive oxygen species (ROS) accumulation and inhibits phosphatidylinositol 3-kinase (PI3K) phosphorylation and increases pyroptosis, while increasing GSDMD and caspase-1 cleavage and enhancing expression of BCL2-associated X (BAX), which could be rescued by the ROS scavenger (NAC), suggesting that SDG-induced GSDME-dependent pyroptosis is related to the ROS/PI3K/AKT/BAX-mitochondrial apoptotic pathway. In vivo results showed that SDG significantly inhibited tumor growth and induced pyroptosis in the HCT116-CRC nude mouse model. In conclusion, our findings suggest that the anticancer activity of SDG in CRC is associated with the induction of GSDMD-dependent pyroptosis by SDG through the generation of ROS/P13K/AKT/BAK-mitochondrail apoptosis pathway, providing insights into SDG in its potential new application in cancer treatment.
Potential protective properties of flax lignan secoisolariciresinol diglucoside
Nutr J 2015 Jul 28;14:71.PMID:26215288DOI:10.1186/s12937-015-0059-3.
Lignans are a group of phytonutrients which are widely distributed in the plant kingdom. Flaxseed is the richest source of providing lignan precursor such as Secoisolariciresinol diglucoside (SDG). This article reviews the studies relevant to experimental models in animals and humans demonstrating the possible nutraceutical actions of SDG to prevent and alleviate lifestyle-related diseases. A local and international web-based literature review for this project was carried out to provide information relating to the study. The major key word "SDG" was selected to gather information using the electronic databases pertaining to the current state of flaxseed lignans composition, bioactive compounds, metabolism and to find out their role in terms of chemopreventive action. The extraction methods vary from simple to complex depending on separation, fractionation, identification and detection of the analytes. The majority of studies demonstrate that SDG interferes with the development of different types of diseases like cardiovascular, diabetic, lupus nephritis, bone, kidney, menopause, reproduction, mental stress, immunity, atherosclerosis, hemopoietic, liver necrosis and urinary disorders due to its various biological properties including anti-inflammatory, antioxidant, antimutagenic, antimicrobial, antiobesity, antihypolipidemic and neuroprotective effects. Moreover, SDG has a defending mediator against various cancers by modulating multiple cell signaling pathways. As discussed in this review, SDG has shown therapeutic potential against a number of human diseases and can be recommended for discerning consumers.