5,7-二羟基-3-[(2R,3R,4S,5S,6R)-5-羟基-6-(羟基甲基)-3,4-二[[(2S,3R,4R,5R,6S)-3,4,5-三羟基-6-甲基四氢吡喃-2-基]氧基]四氢吡喃-2-基]氧基-2-(4-羟基苯基)苯并吡喃-4-酮 | 109008-28-8

• 物质功能分类: 生物化工 - 天然产物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 5,7-二羟基-3-[(2R,3R,4S,5S,6R)-5-羟基-6-(羟基甲基)-3,4-二[[(2S,3R,4R,5R,6S)-3,4,5-三羟基-6-甲基四氢吡喃-2-基]氧基]四氢吡喃-2-基]氧基-2-(4-羟基苯基)苯并吡喃-4-酮
• 中文别名: 毛里求斯排草素
• 英文名称: kaempferol 3-O-{αl-L-rhamnopyranosyl(1→6)-[α-L-rhamnopyranosyl-(1→2)]}-β-D-galactopyranoside
• 英文别名: kaempferol 3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→6)-β-D-galactopyranoside]；kaempferol 3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→6)]-β-D-galactopyranoside；kaempferol-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→6)]-β-D-galactopyranoside；kaempferol 3-O-α-L-rhamnopyranosyl(1->2)[α-L-rhamnopyranosyl(1->6)]-β-D-galactopyranoside；kaempferol 3-O-α-L-rhamnopyranosyl-(1→6)-[α-L-rhamnopyranosyl(1→2)]-β-D-galactopyranoside；kaempferol-3-O-α-L-rhamnopyranosyl(1->6)-O-[L-rhamnopyranosyl(1->2)]-O-β-D-galactopyranoside；3-[(2S,3R,4S,5R,6R)-4,5-Dihydroxy-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• CAS: 109008-28-8
• 化学式: C₃₃H₄₀O₁₉
• 分子量: 740.669
• InChiKey: WRXVPTMENPZUIZ-MOVIZTNPSA-N

物化性质

• 熔点：
  196-198 °C(Solv: methanol (67-56-1); acetone (67-64-1))
• 沸点：
  1054.0±65.0 °C(Predicted)
• 密度：
  1.74±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  52
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  304
• 氢给体数：
  11
• 氢受体数：
  19

制备方法与用途

生物活性

Mauritianin 是从 Acalypha indica 的花和叶中分离出的一种山奈酚。它是一种拓扑异构酶 I 抑制剂。

靶点

• Topoisomerase I

反应信息

• 作为反应物：
  描述：

  5,7-二羟基-3-[(2R,3R,4S,5S,6R)-5-羟基-6-(羟基甲基)-3,4-二[[(2S,3R,4R,5R,6S)-3,4,5-三羟基-6-甲基四氢吡喃-2-基]氧基]四氢吡喃-2-基]氧基-2-(4-羟基苯基)苯并吡喃-4-酮 在 盐酸 、 水 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以3 mg的产率得到山奈酚
  参考文献：
  名称：

  Antioxidative Caffeoylquinic Acids and Flavonoids from Hemerocallis fulva Flowers

  摘要：

  Tumor necrosis factor-alpha (TNF-alpha)-induced reactive oxygen species (ROS) production in HepG2 was used to screen hepatocyte protective compounds from the flowers of Hemerocallis fulva. Three new polyphenols, n-butyl 4-trans-O-caffeoylquinate (1), kaempferol 3-O-{alpha-L-rhamnopyranosyl(1 -> 6)[alpha-L-rhamnopyranosyl(1 -> 2)]}-beta-D-galactopyranoside (2), and chrysoeriol 7-O-[beta-D-glucuronopyranosyl(1 -> 2)(2-O-trans-feruloyl)-beta-D-glucuronopyranoside (3), together with four caffeoylquinic acid derivatives (4-7), eight known flavones (8-15), one naphthalene glycoside, stelladerol (16), one tryptophan derivative (17), adenosine (18), and guanosine (19) were isolated from the bioactive fractions of the aqueous ethanol extract of H. fulva flowers. The structures of isolated compounds were characterized by means of spectroscopic data. Compounds 1-3 were described as first isolated natural products. Among the above-mentioned compounds, the caffeoylquinic acid derivatives are the major components with potent free radical scavenging activity in HepG2 cells and are for the first time isolated from H. fulva flowers. A convenient ultraperformance liquid chromatography (UPLC) method was also developed to simultaneously separate and identify caffeoylquinic acids and flavonoids promptly.

  DOI：

  10.1021/jf201166b

文献信息

• Topical formulations and methods of use
  申请人：Morariu Marius

  公开号：US20060216251A1

  公开（公告）日：2006-09-28

  A topical composition comprising a lipoic acid, a carnitine, and a carnosine in a suitable vehicle for topical application and a method for treating skin is provided. The present compositions are useful in improving the appearance of aged skin characterized by wrinkles and loss of elasticity. Preferred components include R-lipoic acid or R-dihydrolipoic acid, acetyl-1-carnitine, and 1-carnosine.

  本发明提供了一种外用组合物，该组合物包含硫辛酸、肉毒碱和肉毒碱，并以适合外用的载体形式存在，还提供了一种治疗皮肤的方法。本组合物有助于改善以皱纹和失去弹性为特征的老化皮肤的外观。优选成分包括 R-硫辛酸或 R-二氢硫辛酸、乙酰基-1-肉碱和 1-肉碱。
• COMPOSITIONS FOR PROLIFERATION OF CELLS AND RELATED METHODS
  申请人：The Hospital For Sick Children

  公开号：EP2598150A2

  公开（公告）日：2013-06-05
• FURANOCOUMARINS FOR USE IN THE TREATMENT AND/OR PREVENTION OF PARASITIC MEDIATED DISEASES
  申请人：Leeward Pacific Pte Ltd

  公开号：EP3389649B1

  公开（公告）日：2020-10-21
• COMPOUND FOR USE IN THE TREATMENT AND/OR PREVENTION OF PARASITIC MEDIATED DISEASES
  申请人：Leeward Pacific Pte Ltd

  公开号：EP3389649A1

  公开（公告）日：2018-10-24
• Methods of Treating Skin
  申请人：Morariu Marius

  公开号：US20100272790A1

  公开（公告）日：2010-10-28

  A topical composition comprising a lipoic acid, a carnitine, and a carnosine in a suitable vehicle for topical application and a method for treating skin is provided. The present compositions are useful in improving the appearance of aged skin characterized by wrinkles and loss of elasticity. Preferred components include R-lipoic acid or R-dihydrolipoic acid, acetyl-l-carnitine, and l-carnosine.