芦荟宁 | 38412-46-3

• 物质功能分类: 分析化学 - 标准品 - 分析标准品
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 芦荟宁
• 英文名称: 6-(2'-O-β-D-glucopyranosyl-4'-hydroxy-6'-methylphenyl)-4-methoxy-2-pyrone
• 英文别名: aloenin A；aloenin；6-[4-hydroxy-2-methyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-4-methoxypyran-2-one
• CAS: 38412-46-3
• 化学式: C₁₉H₂₂O₁₀
• 分子量: 410.378
• InChiKey: KFJNVVJUICKJEQ-LQDZTQBFSA-N

物化性质

• 熔点：
  145℃
• 沸点：
  787.8±60.0 °C(Predicted)
• 密度：
  1.56

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  155
• 氢给体数：
  5
• 氢受体数：
  10

安全信息

• WGK Germany：
  3

制备方法与用途

生物活性方面，Aloenin（Aloenin A）是一类从芦荟中分离出的蒽醌类化合物。它能够有效清除过氧自由基，并对β-分泌酶(BACE)具有中等抑制活性。

化学性质上，Aloenin 为绿色粉末状物质，可溶于甲醇、乙醇和DMSO等多种有机溶剂。这种化合物来源于百合科植物斑纹芦荟（Aloe vera L. var. chinensis (Haw.) Berger）的叶片。

在应用方面，芦荟宁能够抑制胃液分泌，并且适用于含量测定、鉴定以及药理实验等研究中。

反应信息

• 作为反应物：
  描述：

  芦荟宁 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 生成 6-(2,4-diacetoxy-6-methyl-phenyl)-4-methoxy-pyran-2-one
  参考文献：
  名称：

  Anthraquinone, anthrone and phenylpyrone components of Aloe nyeriensis var. kedongensis leaf exudate

  摘要：

  The leaf exudate of Aloe nyeriensis var. kedongensis yielded six compounds which were identified on the basis of spectral data and inter-conversions as two groups of three allied compounds. These were (a) 4-methoxy-6-(2'',4''-dihydroxy-6''-methylphenyl)-pyran-2-one, its 2''-O-.beta.-D-glucopyranoside (aloenin) and the 2"-O-p-coumaroyl ester of aloenin, (b) the anthracene derivatives 1,2,8-trihydroxy-6-methylanthraquinone (nataloe-emodin), its 2-O-.beta.-D-glucopyranosyl ester and the corresponding 10-C-.beta.-D-glucopyranoside nataloin.

  DOI：

  10.1016/s0031-9422(00)84578-1

文献信息

• Pyrone polyketides synthesized by a type III polyketide synthase from Drosophyllum lusitanicum
  作者：Aphacha Jindaprasert、Karin Springob、Jürgen Schmidt、Wanchai De-Eknamkul、Toni M. Kutchan

  DOI：10.1016/j.phytochem.2008.03.013

  日期：2008.12

  To isolate cDNAs involved in the biosynthesis of acetate-derived naphthoquinones in Drosophyllum lusitanicum, an expressed sequence tag analysis was performed. RNA from callus cultures was used to create a cDNA library from which 2004 expressed sequence tags were generated. One cDNA with similarity to known type III polyketicle synthases was isolated as full-length sequence and termed DluHKS. The translated polypepticle sequence of DIuHKS showed 51-67% identity with other plant type III PKSs. Recombinant DIuHKS expressed in Escherichia coli accepted acetyl-coenzyme A (CoA) as starter and carried out sequential decarboxylative condensations with malonyl-CoA yielding ot-pyrones from three to six acetate units. However, naphthalenes, the expected products, were not isolated. Since the main compound produced by DIuHKS is a hexaketicle ot-pyrone, and the naphthoquinones in D. lusitanicum are composed of six acetate units, we propose that the enzyme provides the backbone of these secondary metabolites. An involvement of accessory proteins in this biosynthetic pathway is discussed. (c) 2008 Elsevier Ltd. All rights reserved.
• Anthraquinone, anthrone and phenylpyrone components of Aloe nyeriensis var. kedongensis leaf exudate
  作者：John M. Conner、Alexander I. Gray、Tom Reynolds、Peter G. Waterman

  DOI：10.1016/s0031-9422(00)84578-1

  日期：——

  The leaf exudate of Aloe nyeriensis var. kedongensis yielded six compounds which were identified on the basis of spectral data and inter-conversions as two groups of three allied compounds. These were (a) 4-methoxy-6-(2'',4''-dihydroxy-6''-methylphenyl)-pyran-2-one, its 2''-O-.beta.-D-glucopyranoside (aloenin) and the 2"-O-p-coumaroyl ester of aloenin, (b) the anthracene derivatives 1,2,8-trihydroxy-6-methylanthraquinone (nataloe-emodin), its 2-O-.beta.-D-glucopyranosyl ester and the corresponding 10-C-.beta.-D-glucopyranoside nataloin.