(+)-Viroallosecurinine
(Synonyms: 别一叶萩碱) 目录号 : GC34439(+)-Viroallosecurinine从Securinegavirosa中分离的一种细胞毒性生物碱,抑制Ps.Aeruginosa和Staph.aureus,MIC为0.48μg/mL。具有抗菌活性。
Cas No.:1857-30-3
Sample solution is provided at 25 µL, 10mM.
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(+)-Viroallosecurinine, isolated from Securinega virosa as a cytotoxic alkaloid, exhibits a MIC of 0.48 μg/mL for Ps. Aeruginosa and Staph. aureus[1]. Antibacterial activity[1].
[1]. Mensah JL, et al. Antibacterial activity of the leaves of Phyllanthus discoideus. J Ethnopharmacol. 1990 Feb;28(1):129-33.
Cas No. | 1857-30-3 | SDF | |
别名 | 别一叶萩碱 | ||
Canonical SMILES | O=C(O1)C=C2[C@]13[C@](CCCC4)([H])N4[C@H](C3)C=C2 | ||
分子式 | C13H15NO2 | 分子量 | 217.26 |
溶解度 | Soluble in DMSO | 储存条件 | Store at -20°C |
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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 | |||
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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,
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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。
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Diastereoselective synthesis of allosecurinine and viroallosecurinine from menisdaurilide
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.
Biosynthetically Inspired Syntheses of Secu'amamine A and Fluvirosaones A and B
Presented here is a concise synthesis of secu'amamine A, and fluvirosaones A and B from readily available allosecurinine and viroallosecurinine. The key C2-enamine derivative of (viro)allosecurinine, the presumed biosynthetic precursors of these natural products, was accessed, for the first time, by a VO(acac)2 -mediated regioselective Polonovski reaction. Formal hydration and 1,2-amine shift of this pluripotent enamine compound afforded secu'amamine A. Formal oxidative [3+2] cycloaddition reaction between this enamine and TMS-substituted methallyl iodide reagent paved the way to the precursors of fluvirosaones A and B. The relative stereochemistry at the C2 position of these advanced intermediates governs the fate of 1,2-amine shift leading to fluvirosaones A and B. The syntheses of potential biosynthetic precursors and investigations of their chemical reactivities have provided insights regarding the biogenesis of these natural products.
Cytotoxic principles of Securinega virosa: virosecurinine and viroallosecurinine and related derivatives
Virosecurinine (1) and viroallosecurinine (2) were isolated as two cytotoxic alkaloids from the leaves of Securinega virosa. A comparison of the cytotoxicity of 1 and several of its derivatives indicates that an alpha,beta- and a gamma,delta-unsaturated lactone located in a strained ring system, such as rings -B, -C, and -D of 1, is structurally required for significant cytotoxicity.
[DETERMINATION OF SECURININE AND ITS STEREOISOMERS IN PLANTS OF THE SECURINEGA SPECIES, AND ISOLATION OF VIROALLOSECURININE AND VIROSINE]
Antibacterial and Antifungal Alkaloids from Asian Angiosperms: Distribution, Mechanisms of Action, Structure-Activity, and Clinical Potentials
The emergence of multidrug-resistant bacteria and fungi requires the development of antibiotics and antifungal agents. This review identified natural products isolated from Asian angiosperms with antibacterial and/or antifungal activities and analyzed their distribution, molecular weights, solubility, and modes of action. All data in this review were compiled from Google Scholar, PubMed, Science Direct, Web of Science, ChemSpider, PubChem, and a library search from 1979 to 2022. One hundred and forty-one antibacterial and/or antifungal alkaloids were identified during this period, mainly from basal angiosperms. The most active alkaloids are mainly planar, amphiphilic, with a molecular mass between 200 and 400 g/mol, and a polar surface area of about 50 ?2, and target DNA and/or topoisomerase as well as the cytoplasmic membrane. 8-Acetylnorchelerythrine, cryptolepine, 8-hydroxydihydrochelerythrine, 6-methoxydihydrosanguinarine, 2'-nortiliacorinine, pendulamine A and B, rhetsisine, sampangine, tiliacorine, tryptanthrin, tylophorinine, vallesamine, and viroallosecurinine yielded MIC ≤ 1 ?g/mL and are candidates for the development of lead molecules.