Allosecurinine
(Synonyms: 别一叶萩碱,Phyllochrysine) 目录号 : GC39304
Allosecurinine (Phyllochrysine) is a Securinega alkaloid isolated from M.indica and M.discoidea with antifungal activity.
Cas No.:884-68-4
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
Allosecurinine (Phyllochrysine) is a Securinega alkaloid isolated from M.indica and M.discoidea with antifungal activity.
[1] A K Singh, et al. Mycobiology. 2007 Jun;35(2):62-4.
| Cas No. | 884-68-4 | SDF | |
| 别名 | 别一叶萩碱,Phyllochrysine | ||
| Canonical SMILES | O=C(O1)C=C2[C@@]13[C@@](CCCC4)([H])N4[C@](C3)([H])C=C2 | ||
| 分子式 | C13H15NO2 | 分子量 | 217.26 |
| 溶解度 | DMSO: 125 mg/mL (575.35 mM) | 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 | 4.6028 mL | 23.0139 mL | 46.0278 mL |
| 5 mM | 0.9206 mL | 4.6028 mL | 9.2056 mL |
| 10 mM | 0.4603 mL | 2.3014 mL | 4.6028 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。
Diastereoselective synthesis of Allosecurinine and viroallosecurinine from menisdaurilide
J Org Chem 2008 Oct 3;73(19):7657-62.PMID:18781804DOI:10.1021/jo801470u.
A new and versatile synthetic route to Securinega alkaloids is reported. The first synthesis of Allosecurinine has been accomplished in seven steps and 40% yield, starting from (+)-menisdaurilide, using a vinylogous Mannich reaction as the key transformation. Similarly, viroallosecurinine has been synthesized from (-)-menisdaurilide.
Total syntheses of (±)-securinine and (±)- Allosecurinine
Org Lett 2012 Sep 7;14(17):4531-3.PMID:22913575DOI:10.1021/ol3020072.
Total syntheses of (±)-securinine and (±)-allosecurinine that employ a tandem rhodium carbenoid-initiated Claisen/α-ketol rearrangement sequence as a key step are described.
Antifungal Activity of an Alkaloid Allosecurinine against Some Fungi
Mycobiology 2007 Jun;35(2):62-4.PMID:24015071DOI:10.4489/MYCO.2007.35.2.062.
An Allosecurinine alkaloid was assayed against spore germination of some saprophytic and pathogenic fungi e.g., Alternaria alternata, A. solani, A. brassicicola, A. brassicae, Curvularia lunata, C. pallescens, C. maculans, Curvularia species, Colletotrichum species, C. musae, C. gloeosporioides, Erysiphe pisi, Fusarium udum, Helminthosporium echinoclova, H. pennisetti, H. spiciferum, and Heterosporium sp. It inhibited mild spore germination of all the fungi tested. Curvularia lunata, Curvularia sp., Collectotrichum sp., C. musae and Heterosporium sp. were most sensitive as complete inhibition of spore germination was observed at very low concentrations.
Synthesis, biological activity and mechanism of action of novel Allosecurinine derivatives as potential antitumor agents
Bioorg Med Chem 2023 Mar 15;82:117234.PMID:36906964DOI:10.1016/j.bmc.2023.117234.
Cancer with low survival rates is the second main cause of death among all diseases in the world and consequently, effective antineoplastic agents are urgently needed. Allosecurinine is a plant-derived indolicidine securinega alkaloid shown bioactivity. The object of this study is to investigate synthetic Allosecurinine derivatives with considerable anticancer capacity against nine human cancer cell lines as well as mechanism of action. We synthesized twenty-three novel Allosecurinine derivatives and evaluated their antitumor activity against nine cancer cell lines for 72 h by MTT and CCK8 assays. FCM was applied to analyze the apoptosis, mitochondrial membrane potential, DNA content, ROS production, CD11b expression. Western blot was selected to analyze the protein expression. Structure-activity relationships were established and potential anticancer lead BA-3 which induced differentiation of leukemia cells towards granulocytosis at low concentration and apoptosis at high concentration was identified. Mechanism studies showed that mitochondrial pathway mediated apoptosis within cancer cells with cell cycle blocking was induced by BA-3. In addition, western blot assays revealed that BA-3 induced expression of the proapoptotic factor Bax, p21 and reduced the levels of antiapoptotic protein such as Bcl-2, XIAP, YAP1, PARP, STAT3, p-STAT3, and c-Myc. Collectively, BA-3 was a lead compound for oncotherapy at least in part, through the STAT3 pathway. These results were an important step in further studies on allosecurinine-based antitumor agent development.
Proposed biogenetic origin of secu'amamine A from Allosecurinine: a model study to support the intermediacy of the putative aziridinium ion
Org Lett 2006 Aug 3;8(16):3569-71.PMID:16869662DOI:10.1021/ol061391a.
[reaction: see text] A model study to support the intermediacy of the aziridinium ion in the proposed biogenetic origin of secu'amamine A from Allosecurinine is described.