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(+)-Viroallosecurinine Sale

(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。

(+)-Viroallosecurinine Chemical Structure

Cas No.:1857-30-3

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5mg
¥4,950.00
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10mg
¥7,650.00
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Sample solution is provided at 25 µL, 10mM.

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产品描述

(+)-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.

Chemical Properties

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 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
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Research Update

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.