ellagic acid tetraacetate | 4274-26-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: ellagic acid tetraacetate
• 英文别名: Ellagsaeure-tetraacetat；ellagic acid peracetate；Tetraacetylellagsaeure；Ellagsaeure-acetat；Tetra-O-acetyl-ellagsaeure；(7,13,14-triacetyloxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),4,6,8(16),11,13-hexaen-6-yl) acetate
• CAS: 4274-26-4
• 化学式: C₂₂H₁₄O₁₂
• 分子量: 470.346
• InChiKey: ZYIHXOSKMVETGC-UHFFFAOYSA-N

物化性质

• 熔点：
  317-319 °C
• 沸点：
  698.2±55.0 °C(Predicted)
• 密度：
  1.552±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  158
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  ellagic acid tetraacetate 以 吡啶 、 水 为溶剂， 生成 ellagic acid diacetate
  参考文献：
  名称：

  Ellagic acid derivatives as phospholipase A.sub.2 inhibitors

  摘要：

  本发明揭示了一种通过向哺乳动物施用具有以下式子的化合物的有效量来治疗或预防免疫炎症疾病的方法：##STR1##其中R.sup.1，R.sup.2，R.sup.3和R.sup.4各自独立地表示氢，烷基，芳基烷基，芳基或##STR2##X表示烷基，芳基或-NR.sup.5 R.sup.6; R.sup.5和R.sup.6各自独立地表示氢，烷基或芳基; 芳基为##STR3##其中虚线表示可选的双键; R.sup.7，R.sup.8和R.sup.9各自独立地表示氢，烷基，羟基，烷氧基，羧烷氧基，卤素，硝基，氨基，氰基，三氟甲基或羧酸；n = 1-3；或其药学上可接受的盐。

  公开号：

  US05066671A1
• 作为产物：
  描述：

  1,2,3,4,6-penta-O-galloyl-α-D-glucose 在 sodium carbonate 作用下， 以 吡啶 为溶剂， 反应 18.0h， 生成 ellagic acid tetraacetate
  参考文献：
  名称：

  Synthesis and Antitumor Activity of Ellagic Acid Peracetate

  摘要：

  Ellagic acid (1) was synthesized for the first time from methyl gallate through a-pentagalloylglucose (alpha-PGG), and ellagic acid peracetate (3,4,3',4'-tetra-O-acetylellagic acid, 2) was derived from 1 by acetylation. Oral administration of 2 suppressed melanoma growth significantly in C7BL/6 immunocompetent mice without having any effect on natural killer (NK) cell activity. Comparison of the immunoenhancing activities of 1 and 2 indicated that the latter compound increased white blood cell quantities in peripheral blood and immune cells enriched from the bone marrow and liver of mice. Therefore, both the antitumor efficacy and the immunity enhancement by 2 were greater than those by 1. In addition, on oral administration, neither 1 nor 2 resulted in whole body, liver, or spleen weight changes of normal, tumor-free mice, indicating that these compounds are potentially nontoxic to mice. It was shown that ellagic acid peracetate (2) inhibits B16 melanoma cell growth in vitro and induces B16 cell apoptosis, corresponding to BCL-2 down-regulation. Collectively, the present data imply that 2 can suppress tumor growth by enhancing mouse immunity and inducing tumor cell apoptosis without apparent side effects.

  DOI：

  10.1021/ml300065z

文献信息

• Studies on aldose reductase inhibitors from natural products. Part III. Studies on aldose reductase inhibitors from medicinal plant of "Sinfito," Potentilla candicans, and further synthesis of their related compounds.
  作者：Satoshi TERASHIMA、Mineo SHIMIZU、Hajime NAKAYAMA、Masatoshi ISHIKURA、Yutaka UEDA、Kunihiro IMAI、Akio SUZUI、Naokata MORITA

  DOI：10.1248/cpb.38.2733

  日期：——

  For several years we have screened natural products having aldose reductase (AR) inhibitory activity. 3, 3', 4-Tri-O-methylellagic acid 4'-sulfate potassium salt (2) was isolated from a Mexican herb "Sinfito" (Potentilla candicans) as a potent AR inhibitory active constituent. 2 was more potent (IC<50>=8.0×10<-8>M) than ellagic acid, which is one of the natural inhibitors of AR. So we examined the synthesis of ellagic acid derivatives and found that the sulfate group is one of the important function.

  在过去几年里，我们对具有醛糖还原酶（AR）抑制活性的天然产物进行了筛选。从一种墨西哥香草“Sinfito”（Potentilla candicans）中分离出了3, 3', 4-三-O-甲基鞣酸4'-硫酸钾盐（2），作为一种有效的AR抑制活性成分。其活性比鞣酸更强（IC<50>=8.0×10<-8>M），而鞣酸是AR的自然抑制剂之一。因此，我们研究了鞣酸衍生物的合成，并发现硫酸酯基团是一个重要的功能团。
• Ellagic acid peracetate is superior to ellagic acid in the prevention of genotoxicity due to aflatoxin B₁in bone marrow and lung cells
  作者：Ajit Kumar、Yogesh K. Tyagi、Prija Ponnan、Vishwajeet Rohil、Ashok K. Prasad、Bilekere S. Dwarkanath、Virinder S. Parmar、Hanumantharao G. Raj

  DOI：10.1211/jpp.59.1.0011

  日期：2007.1

  Earlier observations carried out in our laboratory highlighted the mode of action of acetoxy 4-meth-ylcoumarins and quercetin pentaacetate in preventing the genotoxicity of aflatoxin B1 (AFB1). We have extended the observation to an acetoxy biscoumarin i.e. ellagic acid peracetate (EAPA), which unlike ellagic acid (EA) has demonstrated time-dependent inhibition of liver microsomes catalysed AFB1-epoxidation as measured by AFB1 binding to DNA. EAPA was more potent than EA in preventing bone marrow and lung cells from AFB1-induced genotoxicity. EAPA was acted upon by microsomal acetoxy drug:protein transacetylase (TAase) leading to modulation of the catalytic activity of certain functional proteins (cytochrome P450, NADPH cytochrome c reductase and glutathione S-transferase), possibly by way of protein acetylation.

  我们实验室早期的观察突出了乙酰氧基4-甲基香豆素和五乙酰基槲皮素在防止黄曲霉毒素B1（AFB1）致基因毒性的作用机制。我们将观察扩展到一种乙酰氧基双香豆素，即乙酰化鞣酸（EAPA），与鞣酸（EA）不同，EAPA表现出时间依赖性抑制肝微粒体催化的AFB1环氧化反应，这一反应通过AFB1与DNA的结合进行测量。EAPA在防止骨髓和肺细胞受到AFB1引起的基因毒性方面比EA更有效。EAPA受到微粒体乙酰氧基药物：蛋白质转乙酰酶（TAase）的作用，导致某些功能蛋白（细胞色素P450、NADPH细胞色素c还原酶和谷胱甘肽S-转移酶）催化活性的调节，可能是通过蛋白质乙酰化的方式。
• Anti-babesial and Anti-plasmodial Compounds from <i>Phyllanthus </i><i>n</i><i>iruri</i>
  作者：Subeki、Hideyuki Matsuura、Kosaku Takahashi、Masahiro Yamasaki、Osamu Yamato、Yoshimitsu Maede、Ken Katakura、Sumiko Kobayashi、Trimurningsih、Chairul、Teruhiko Yoshihara

  DOI：10.1021/np0497245

  日期：2005.4.1

  Bioassay-guided fractionation of boiled aqueous extracts from the whole plant of Phyllanthus niruri led to the isolation of 1-O-galloyl-6-O-luteoyl-alpha-d-glucose (1), with IC(50) values of 4.7 microg/mL against Babesia gibsoni and 1.4 microg/mL against Plasmodium falciparum in vitro. The known compounds beta-glucogallin (2), quercetin 3-O-beta-d-glucopyranosyl-(2-->1)-O-beta-d-xylopyranoside (3)

  生物测定指导下的楠竹全植物煮沸水提取物的分馏导致分离出1-O-galloyl-6-O-luteoyl-alpha-d-葡萄糖（1），IC（50）值为4.7微克/ mL对抗长臂猿巴贝斯虫和1.4 microg / mL体外抗恶性疟原虫。还分离出了已知的化合物β-葡萄糖gallin（2），槲皮素3-O-β-d-吡喃葡萄糖基-（2-> 1）-O-β-d-吡喃吡喃糖苷（3），β-谷甾醇和没食子酸。根据它们的化学和光谱数据阐明了这些化合物的结构。
• SKIN LIGHTENING COMPOSITION
  申请人：DAIICHI PHARMACEUTICAL CO., LTD.

  公开号：EP1586315A1

  公开（公告）日：2005-10-19

  A composition which comprises (i) tranexamic acid or a salt thereof, (ii) L-cysteine, a derivative thereof or a salt thereof and, as occasion demands, (iii) L-ascorbic acid, a derivative thereof or a salt thereof.

  一种组合物，其中包括(i)氨甲环酸或其盐，(ii)L-半胱氨酸、其衍生物或其盐，以及在需要时，(iii)L-抗坏血酸、其衍生物或其盐。
• Skin lightening composition
  申请人：Morimoto Yoshinobu

  公开号：US20060142382A1

  公开（公告）日：2006-06-29

  A composition which comprises (i) tranexamic acid or a salt thereof, (ii) L-cysteine, a derivative thereof or a salt thereof and, as occasion demands, (iii) L-ascorbic acid, a derivative thereof or a salt thereof.

  一种组合物，其中包括(i)氨甲环酸或其盐，(ii)L-半胱氨酸、其衍生物或其盐，以及在需要时，(iii)L-抗坏血酸、其衍生物或其盐。