Secoisolariciresinol
(Synonyms: (+)-开环异落叶松脂素) 目录号 : GC37616
A lignan with diverse biological activities
Cas No.:29388-59-8
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
(–)-Secoisolariciresinol is a lignan that has been found in flaxseed and has diverse biological activities.1,2,3 It scavenges DPPH radicals (IC50 = 13.7 ?g/ml in a cell-free assay).1 (–)-Secoisolariciresinol (0.1-100 ?M) stimulates IgM production in HB4C5 hybridoma cells.2 It induces estrogen receptor-dependent gene expression in a reporter assay, as well as stimulates proliferation of MCF-7 human breast cancer cells, in a concentration-dependent manner. (–)-Secoisolariciresinol (5.8 mg/kg, p.o.) reduces weight gain and serum adiponectin levels in a mouse model of obesity induced by a high-fat diet (HFD).3
1.Rao, J.M., Tiwari, A.K., Kumar, U.S., et al.(-)-Secoisolariciresinol as an antioxidant obtained from a new natural source namely Stereopermum personatum(2002) 2.Sugahara, T., Yamauchi, S., Nishimoto, S., et al.The structure-activity relationships of flaxseed lignan, secoisolariciresinolInterdisciplinary Studies on Environmental Chemistry263-268(2008) 3.Tominaga, S., Nishi, K., Nishimoto, S., et al.(–)-Secoisolariciresinol attenuates high-fat diet-induced obesity in C57BL/6 miceFood Funct.3(1)76-82(2012)
| Cas No. | 29388-59-8 | SDF | |
| 别名 | (+)-开环异落叶松脂素 | ||
| Canonical SMILES | COC1=C(O)C=CC(C[C@@H](CO)[C@H](CO)CC2=CC(OC)=C(O)C=C2)=C1 | ||
| 分子式 | C20H26O6 | 分子量 | 362.42 |
| 溶解度 | DMSO: 10 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 | 2.7592 mL | 13.7961 mL | 27.5923 mL |
| 5 mM | 0.5518 mL | 2.7592 mL | 5.5185 mL |
| 10 mM | 0.2759 mL | 1.3796 mL | 2.7592 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.
Dietary Flaxseed as a Strategy for Improving Human Health
Nutrients 2019 May 25;11(5):1171.PMID:31130604DOI:10.3390/nu11051171.
Flaxseed is a rich source of the omega-3 fatty acid, alpha linolenic acid, the lignan Secoisolariciresinol diglucoside and fiber. These compounds provide bioactivity of value to the health of animals and humans through their anti-inflammatory action, anti-oxidative capacity and lipid modulating properties. The characteristics of ingesting flaxseed or its bioactive components are discussed in this article. The benefits of administering flaxseed or the individual bioactive components on health and disease are also discussed in this review. Specifically, the current evidence on the benefits or limitations of dietary flaxseed in a variety of cardiovascular diseases, cancer, gastro-intestinal health and brain development and function, as well as hormonal status in menopausal women, are comprehensive topics for discussion.
The legitimacy of using dietary supplement diglycoside Secoisolariciresinol (SDG) from flaxseed in cancer
Rocz Panstw Zakl Hig 2021;72(1):9-20.PMID:33882661DOI:10.32394/rpzh.2021.0144.
Linseed, commonly known as flaxseed, is a fibre-rich food product. According to the recent study prepared by the American Institute for Cancer Research (AICR), an adequate intake of dietary fiber contributes to reducing the risk of colorectal cancer. In addition, the flaxseed and the oil extracted from it are considered to be food products with a high content of anti-inflammatory, unsaturated α-linolenic acid (ALA). However, the authors of the most recent scientific research have assigned the anticancer significance of flax seeds to plant lignan - Secoisolariciresinol diglycoside (SDG), of which flaxseed is the main food source. This article provides a review of the world scientific literature together with an assessment of the validity of dietary supplementation with SDG from flaxseeds in cancer and during chemotherapeutic treatment. The paper also presents the European Food Safety Authority (EFSA) and the US Food and Drug Administration (FDA) view on dietary supplementation with flax seeds and its lignans. Additionally, selected dietary supplements available on the Polish market containing SDGs, linseed oil or linseed were analysed, together with a description of their intended use suggested by the manufacturers.
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-derived metabolite, enterolactone, attenuates atopic dermatitis by suppressing Th2 immune response
Int Immunopharmacol 2022 Oct;111:109039.PMID:35914449DOI:10.1016/j.intimp.2022.109039.
Atopic dermatitis (AD) is a severe inflammatory skin disease caused by a combination of genetic, immune, and environmental factors. Intestinal microbiome disorders and changes in the immune microenvironment are associated with AD. We observed that gut bacterial metabolite enterolactone (ENL) was significantly reduced in AD model mice. Notably, patients with early childhood-onset AD exhibited decreased sera ENL level compared to the healthy controls, and the ENL level was negatively correlated with the SCORAD index. Secoisolariciresinol-diglycoside (SDG) is a natural dietary lignan of flaxseeds that can be converted by intestinal bacteria to ENL. Repeated applications of 2,4-dinitrochlorobenzene (DNCB) were performed on the ear and dorsal skin of mice to induce AD-like symptoms and skin lesions. Oral administration of SDG significantly decreased serum IgE levels and limited skin inflammation in the DNCB-induced AD mice. In addition, SDG treatment strongly limited the Th2 responses in AD mice. Moreover, we demonstrated that the IL-4 production was significantly suppressed by ENL under Th2 polarization conditions via the JAK-STAT6 signaling pathway in a concentration-dependent manner. We concluded that SDG and its derived metabolite ENL ameliorated AD development by reducing the Th2 immune response. These results suggested that SDG and ENL might be exploited as potential therapeutic candidates for AD treatment.