别欧前胡素 | 642-05-7

• 物质功能分类: 生物化工 - 提取物 - 植物提取物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: 别欧前胡素
• 中文别名: 9-羟基-4-(3-甲基-2-丁烯-1-基)-7H-呋喃并[3,2-G][1]苯并吡喃-7-酮
• 英文名称: Alloimperatorin
• 英文别名: 9-hydroxy-4-(3-methylbut-2-enyl)furo[3,2-g]chromen-7-one
• CAS: 642-05-7
• 化学式: C₁₆H₁₄O₄
• mdl: MFCD08692712
• 分子量: 270.285
• InChiKey: KDXVVZMYSLWJMA-UHFFFAOYSA-N

物化性质

• 熔点：
  224-225℃
• 沸点：
  476.1±45.0 °C(Predicted)
• 密度：
  1.298

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2932999099
• 储存条件：
  2-8℃

制备方法与用途

生物活性

Alloimperatorin（Prangenidin）是一种从当归（Angelica dahurica）中提取的香豆素类化合物，具有抗肿瘤活性。

反应信息

• 作为反应物：
  描述：

  别欧前胡素 生成 Alloimperatorin acetate
  参考文献：
  名称：

  RAZDAN, T. K.;QADRI, B.;HARKAR, S.;WAIGHT, E. S., PHYTOCHEMISTRY, 26,(1987) N 7, 2063-2069

  摘要：

  DOI：
• 作为产物：
  描述：

  欧前胡素 以 various solvent(s) 为溶剂， 反应 1.0h， 以4.6 g的产率得到别欧前胡素
  参考文献：
  名称：

  Loutfy, Pharmazie, 1981, vol. 36, # 2, p. 166 - 166

  摘要：

  DOI：

文献信息

• Photochemical Reactions of the Natural Furocoumarin, Imperatorin
  作者：M. M. Abou-Elzahab、M. A. Metwally、A. M. Dawidar、M. Abdel-Mogib、E. A. Abu-Mustafa

  DOI：10.1246/bcsj.60.4433

  日期：1987.12

  Photochemical behavior of imperatorin was investigated including photolysis and sigmatropic effects in different solvents and photodimerization. The structures of the photoproducts obtained were determined by chemical and spectral methods.

  研究了欧前胡素的光化学行为，包括在不同溶剂中的光解和σ效应以及光二聚化。所得光产物的结构通过化学和光谱方法确定。
• Chromones and coumarins from Skimmia laureola
  作者：E.S. Waight、T.K. Razdan、B. Qadri、S. Harkar

  DOI：10.1016/s0031-9422(00)81759-8

  日期：——

  Abstract The isolation and characterisation ofchromones and coumarins, including the new chromone, skimminin, from S. laureola is reported.

  摘要 报道了来自 S. laureola 的色酮和香豆素的分离和表征，包括新的色酮脱脂素。
• COMPOSITION FOR PROMOTING SYNTHESIS OF COLLAGEN, AND COMPOSITION FOR EXTERNAL PREPARATION FOR SKIN COMPRISING THE SAME
  申请人：JIN Mu-Hyun

  公开号：US20090233997A1

  公开（公告）日：2009-09-17

  The present invention relates to a composition for promoting collagen synthesis and a composition for external application to skin which includes the collagen synthesis promoting composition. The collagen synthesis promoting composition includes, as an effective component, at least one selected from the group consisting of compounds represented as: wherein R is hydrogen, a methoxy group, or a 3-methyl-2-butenyl group. The composition for external application to skin includes at least one collagen synthesis promoting component selected from the group consisting of compounds represented by above.

  本发明涉及一种促进胶原蛋白合成的组合物和一种用于外用于皮肤的组合物，该组合物包括促进胶原蛋白合成的组合物。促进胶原蛋白合成的组合物包括至少从以下化合物组成的选组中选择的一种有效成分：其中R为氢、甲氧基或3-甲基-2-丁烯基基团。外用于皮肤的组合物包括至少从上述化合物所代表的化合物组成的选组中选择的一种促进胶原蛋白合成的成分。
• Composition for promoting synthesis of collagen, and composition for external preparation for skin comprising the same
  申请人：Jin Mu-Hyun

  公开号：US20070065377A1

  公开（公告）日：2007-03-22

  The present invention relates to a composition for promoting collagen synthesis and a composition for external application to skin which includes the collagen synthesis promoting composition. The collagen synthesis promoting composition includes, as an effective component, at least one selected from the group consisting of compounds represented as: wherein R is hydrogen, a methoxy group, or a 3-methyl-2-butenyl group. The composition for external application to skin includes at least one collagen synthesis promoting component selected from the group consisting of compounds represented by above.

  本发明涉及一种促进胶原蛋白合成的组合物以及一种用于外用于皮肤的组合物，其中包括促进胶原蛋白合成的组合物。促进胶原蛋白合成的组合物包括至少一种选择自以下化合物组成的有效成分：其中R为氢、甲氧基或3-甲基-2-丁烯基。外用于皮肤的组合物包括至少一种选择自上述化合物组成的促进胶原蛋白合成的成分。
• Alloimperatorin and its epoxide derivative exhibit <i>in vitro</i> antitumor activity in HL-60 acute myeloid leukemia cancer cells via inducing apoptosis, cell cycle disruption and inhibition of cell migration
  作者：Hong Li、Xu Chao、Chun-Ling He、Xin-Mei Wang、Man Liang、Chang-Hu Dong

  DOI：10.3329/bjp.v11i1.24575

  日期：——

  <p class="Abstract">The aim of the present study was to synthesize epoxide derivative of alloimperatorin and evaluating its antitumor and apoptotic effects in acute myeloid leukemia HL-60 cells. The cytotoxic effects were demonstrated by MTT assay. Fluorescence microscopy along with flow cytometry were performed to evaluate the effect of alloimperatorin epoxide on apoptosis and cell cycle. <em>In vitro</em> wound healing assay was performed to study compound’s effect on cancer cell migration. The results indicated that alloimperatorin epoxide (IC₅₀ = 32.1 µM) was much more effective in inhibiting HL-60 cancer cell growth as compared to alloimperatorin (IC₅₀ = 128 µM). Further, alloimperatorin epoxide induced apoptosis related morphological alterations in HL-60 cells including blebbing of plasma membrane, DNA fragmentation and formation of apoptotic bodies. Alloimperatorin epoxide also led to G2/M phase cell cycle arrest and suppressed HL-60 cancer cell migration indicating that this compound may be a promising candidate for the treatment of cancer metastasis.</p><p> </p>

  本研究的目的是合成异芹菜素的环氧衍生物，并评估其对急性髓性白血病HL-60细胞的抗肿瘤和凋亡效应。通过MTT试验证明了其细胞毒性效应。使用荧光显微镜和流式细胞术评估异芹菜素环氧衍生物对细胞凋亡和细胞周期的影响。进行了体外伤口愈合实验，以研究该化合物对癌细胞迁移的影响。结果表明，异芹菜素环氧衍生物（IC50 = 32.1 µM）比异芹菜素（IC50 = 128 µM）更有效地抑制了HL-60癌细胞的生长。此外，异芹菜素环氧衍生物引起了HL-60细胞中与凋亡相关的形态学改变，包括质膜凸起、DNA断裂和凋亡小体的形成。异芹菜素环氧衍生物还导致了G2/M期细胞周期阻滞，并抑制了HL-60癌细胞的迁移，表明该化合物可能是治疗癌症转移的有前途的候选药物。