Anhydrosecoisolariciresinol
目录号 : GC35357
Anhydrosecoisolariciresinol 主要源于 Wedelia biflora，具有抗癌活性。Anhydrosecoisolariciresinol 抑制人乳腺癌细胞系 MCF-7 和 MDA-MB-231 的生长。
Cas No.:29388-33-8
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Anhydrosecoisolariciresinol is from the flower of Wedelia biflora, has anti-tumor activities[1].Anhydrosecoisolariciresinol decreases the growth of human breast cancer MCF-7 and MDA-MB-231 cell lines[2].
[1]. Thu NT, et al. Six new phenolic glycosides and a new ceramide from the flowers of Wedelia biflora and their cytotoxicity against some cancer cell lines. Nat Prod Commun. 2013 Mar;8(3):367-72. [2]. Lehraiki A, et al. Extraction of lignans from flaxseed and evaluation of their biological effects on breast cancer MCF-7 and MDA-MB-231 cell lines. J Med Food. 2010 Aug;13(4):834-41.
| Cas No. | 29388-33-8 | SDF | |
| Canonical SMILES | COC1=C(O)C=CC(C[C@@H]2[C@H](COC2)CC3=CC(OC)=C(O)C=C3)=C1 | ||
| 分子式 | C20H24O5 | 分子量 | 344.4 |
| 溶解度 | Soluble in DMSO | 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 | 2.9036 mL | 14.518 mL | 29.036 mL |
| 5 mM | 0.5807 mL | 2.9036 mL | 5.8072 mL |
| 10 mM | 0.2904 mL | 1.4518 mL | 2.9036 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。
Bacterial conversion of secoisolariciresinol and Anhydrosecoisolariciresinol
J Appl Microbiol 2009 Jul;107(1):308-17.PMID:19302311DOI:10.1111/j.1365-2672.2009.04209.x.
Aims: It has been investigated whether secoisolariciresinol (SECO) and Anhydrosecoisolariciresinol (AHS), an acid degradation product of SECO, could be fermented in a similar way, and to a similar extent, by members of the intestinal microbiota. Methods and results: AHS and SECO were demethylated by Peptostreptococcus productus, Eubacterium limosum and Clostridium methoxybenzovorans. These bacteria have been identified as members of the human intestinal flora or closely related species. Demethylated AHS and demethylated SECO were purified by preparative RP-HPLC, and subsequently subjected to fermentation with Eggerthella lenta, Clostridium scindens and Clostridium hiranonis. Eggerthella lenta efficiently dehydroxylated demethylated SECO to enterodiol, whereas the other bacteria showed no dehydroxylation activity. Conclusions: The conversion of the diol structure of SECO into the furan ring in AHS did not influence the demethylation capability of the tested bacteria. The results also showed that the extent of dehydroxylation of demethylated AHS was much lower than that of demethylated SECO. Significance and impact of the study: Plant lignans are converted into bioactive mammalian lignans by the human intestinal bacteria. This study showed that the modification of plant lignans resulted in the formation a new type of mammalian lignan.
Micropropagation and Production of Health Promoting Lignans in Linum usitatissimum
Plants (Basel) 2020 Jun 9;9(6):728.PMID:32526854DOI:10.3390/plants9060728.
Linum usitatissimum commonly known as flax or linseed is an important medicinal plant, produces medicinally potent lignans, used in the treatment of several human diseases. Lignans limited production in the natural plants does not meet the increasing market demand. This study was conducted to establish an easy and rapid method for the in vitro micropropagation and production of potent lignans and antioxidant secondary metabolites in linseed. The results indicated that hypocotyl explants under the effects of thidiazuron (TDZ: 0.5 mg/L) + kinetin (Kn: 0.5 mg/L) in the basal growth media, resulted in the optimal shoot organogenesis parameters (shoot induction frequency: 86.87%, number of shoots: 6.3 ± 0.36 and shoots length: 6.5 ± 0.54 cm), in 4 weeks. Further, TDZ supplementation in the culture media efficiently activated the antioxidant system in the in vitro raised shoots, wherein maximum production of total phenolic content, TPC (34.33 ± 0.20 mg of GAE/g DW); total flavonoid content, TFC (8.99 ± 0.02 mg of QE/g DW); DPPH free radical scavenging activity (92.7 ± 1.32%); phenylalanine ammonia-lyase activity, PAL (8.99 ± 0.02 U/g FW); and superoxide dismutase expression, SOD (3.62 ± 0.01 nM/min/mg FW) were observed in the shoot cultures raised in presence of TDZ: 0.5 mg/L + Kn: 0.5 mg/L. Nonetheless, considerable levels of pharmacologically active lignans such as secoisolariciresinol (SECO: 23.13-37.10 mg/g DW), secoisolariciresinol diglucoside (SDG: 3.32-3.86 mg/g DW) and Anhydrosecoisolariciresinol diglucoside (ANHSECO: 5.15-7.94 mg/g DW) were accumulated in the regenerated shoots. This protocol can be scaled up for the commercial production of linseed to meet the market demands for lignans.
Hydrolysis kinetics of secoisolariciresinol diglucoside oligomers from flaxseed
J Agric Food Chem 2008 Nov 12;56(21):10041-7.PMID:18925741DOI:10.1021/jf8020656.
Flaxseed is the richest dietary source of the lignan secoisolariciresinol diglucoside (SDG) and contains the largest amount of SDG oligomers, which are often hydrolyzed to break the ester linkages for the release of SDG and the glycosidic bonds for the release of secoisolariciresinol (SECO). The alkaline hydrolysis reaction kinetics of SDG oligomers from flaxseed and the acid hydrolysis process of SDG and other glucosides were investigated. For the kinetic modeling, a pseudo-first-order reaction was assumed. The results showed that the alkaline hydrolysis of SDG oligomers followed first-order reaction kinetics under mild alkaline hydrolytic conditions and that the concentration of sodium hydroxide had a strong influence on the activation energy of the alkaline hydrolysis of SDG oligomers. The results also indicated that the main acid hydrolysates of SDG included secoisolariciresinol monoglucoside (SMG), SECO, and Anhydrosecoisolariciresinol (anhydro-SECO) and that the extent and the main hydrolysates of the acid hydrolysis reaction depended on the acid concentration, hydrolysis temperature, and time. In addition, the production and change of p-coumaric acid glucoside, ferulic acid glucoside and their methyl esters and p-coumaric acid, ferulic acid, and their methyl esters during the process of hydrolysis was also investigated.
Detection of novel metabolites of flaxseed lignans in vitro and in vivo
Mol Nutr Food Res 2016 Jul;60(7):1590-601.PMID:26873880DOI:10.1002/mnfr.201500773.
Scope: This study aimed to improve the knowledge of secoisolariciresinol diglucoside (SDG) transformation by human gut microbiota. Methods and results: SDG-supplemented microbiota cultures were inoculated with the feces of five subjects. The same volunteers received a flaxseed supplement for 7 days. SDG metabolites in cultures, feces, and urine were monitored by LC-ESI-QTOF and LC-DAD. In all cultures, SDG was deglycosylated to secoisolariciresinol (SECO) within 12 h. SECO underwent successive dehydroxylations and demethylations yielding enterodiol (4-18% conversion) and enterolactone (0.2-6%) after 24 h. Novel intermediates related to SECO, matairesinol (MATA), and Anhydrosecoisolariciresinol (AHS) were identified in fecal cultures. These metabolites were also found after flaxseed consumption in feces and urine (in approximate amounts between 0.01-47.03 μg/g and 0.01-13.49 μg/mL, respectively) in their native form and/or modified by phase II human enzymes (glucuronide, sulfate and sulfoglucuronide conjugates). Conclusions: Derivatives of MATA and AHS are described for the first time as intermediates of SDG biotransformation by intestinal bacteria, providing a more comprehensive knowledge of lignan intestinal metabolism. The transformations observed in vitro seem to occur in vivo as well. The detection in urine of SDG intermediates indicates their gut absorption, opening new perspectives on the study of their systemic biological effects.
Structural Modifications of a Flaxseed Lignan in Pursuit of Higher Liposolubility: Evaluation of the Antioxidant and Permeability Properties of the Resulting Derivatives
J Agric Food Chem 2019 Dec 26;67(51):14152-14159.PMID:31747278DOI:10.1021/acs.jafc.9b06264.
While lignans and their biogenetic precursors can have various health benefits, the poor liposolubilities of such phenolic systems have restricted their application as antioxidants in the food industry. The research reported here was aimed at addressing these matters through derivatizing certain forms of such compounds and then assessing their properties as potential nutraceuticals. In particular, crude flaxseed lignan was purified to afford secoisolariciresinol diglucoside (SDG, 1) that was then subjected to structural modification. By such means, the SDG long-chain fatty acid esters 4-9 and 11-13, the fully acetylated SDG 10, secoisolariciresinol (SECO, 2), and Anhydrosecoisolariciresinol (ASECO, 14) were obtained. The antioxidant activities of these derivatives were determined while their permeability properties were evaluated. Such studies revealed that certain SDG derivatives possessing useful liposolubilities also retained their antioxidative properties, as well as being capable of permeating Caco-2 cell monolayers while being nontoxic to them. SDG fatty acid esters 4-9 and 11-13 could be developed into emulsifiers with enhanced health benefits, especially considering their improved antioxidative (ca. <11 000 μmol Trolox/g) and permeability properties. This study thus highlights strategies for the structural modification of SDG so as to generate derivatives with superior properties in terms of their utility in the food and pharmaceutical industries.