滨蓟黄甙 | 13020-19-4

• 物质功能分类: 天然产物 - 黄酮类化合物
• 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: 滨蓟黄甙
• 英文名称: Cismaritin
• 英文别名: 5-hydroxy-6,7-dimethoxy-2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one；2-[4-(β-D-glucopyranosyloxy)phenyl]-5-hydroxy-6,7-dimethoxy-4H-1-benzopyran-4-one；cirsimaritin 4′-glucoside；cirsitakaoside；cirsimarin
• CAS: 13020-19-4
• 化学式: C₂₃H₂₄O₁₁
• 分子量: 476.437
• InChiKey: RETJLKUBHXTIGH-FZFRBNDOSA-N

物化性质

• 熔点：
  244-246℃
• 沸点：
  767.1±60.0 °C(Predicted)
• 密度：
  1.523

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  164
• 氢给体数：
  5
• 氢受体数：
  11

安全信息

• WGK Germany：
  3

制备方法与用途

生物活性

Cirsimarin 是一种从 Microtea debilis 中分离出来的有效抗脂类黄酮。它具有显著的抗脂肪作用，能够减少小鼠脂肪组织的沉积。Cirsimarin 的脂解活性源于其对腺苷 A1 受体的拮抗活性及其对磷酸二酯酶 (phosphodiesterase) 的抑制作用。

靶点

• Phosphodiesterase
• Adenosin A1 receptor

反应信息

• 作为产物：
  描述：

  3,4,5-三甲氧基苯酚 在 吡啶 、 硫酸 、 palladium on activated charcoal 、 三氟化硼乙醚 、 苄基三乙基氯化铵 、 水 、 氢气 、 sodium acetate 、 三溴化硼 、 溶剂黄146 、 三乙胺 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 57.0h， 生成 滨蓟黄甙
  参考文献：
  名称：

  Total synthesis of cirsimarin and evidence of its lipolytic and antilipogenic activities on human adipocytes

  摘要：

  A straightforward procedure leading to the flavone cirsimaritin and its 4'-O-beta-D-glycosylation to afford cirsimarin, its corresponding flavone glucopyranoside, is described. The biological properties of cirsimarin, measured on human adipocytes, showed potent effects on both lipolysis and lipogenesis. Cirsimarin could therefore be considered as an efficient tool in the struggle against excessive adipose tissue deposition and as a potential candidate in the treatment of obesity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.034

文献信息

• NOVEL POLYMETHOXYFLAVONE COMPOUNDS FOR SKELETAL MUSCLE MODULATION, METHODS AND USES THEREOF
  申请人：Société des Produits Nestlé S.A.

  公开号：EP3897617A1

  公开（公告）日：2021-10-27
• MISO
  申请人：Koike Shin

  公开号：US20110159151A1

  公开（公告）日：2011-06-30

  The present invention provides miso containing a flavonoid substance having a flavanone, flavone, or flavonol skeleton in an amount of 0.01 to 5% by mass (weight).
• US8399034B2
  申请人：——

  公开号：US8399034B2

  公开（公告）日：2013-03-19
• [EN] NOVEL POLYMETHOXYFLAVONE COMPOUNDS FOR SKELETAL MUSCLE MODULATION, METHODS AND USES THEREOF<br/>[FR] NOUVEAUX COMPOSÉS DE POLYMÉTHOXYFLAVONE POUR LA MODULATION DU MUSCLE SQUELETTIQUE, PROCÉDÉS ET UTILISATIONS DE CEUX-CI
  申请人：NESTLE SA

  公开号：WO2020127183A1

  公开（公告）日：2020-06-25

  The present invention relates to novel polymethoxyflavone compounds for improving skeletal muscle plasticity regeneration to maintain or increase muscle function and/or muscle mass by modulating muscle stem cells. For example, the present invention is useful for subjects to promote muscle repair and/or subjects suffering from precachexia, cachexia, sarcopenia, myopathy, dystrophy and/or recovery after muscle injury or surgery.
• Total synthesis of cirsimarin and evidence of its lipolytic and antilipogenic activities on human adipocytes
  作者：Christophe O. Soulage、Lucie Grand、Alain Géloën、Stéphane Chambert

  DOI：10.1016/j.tetlet.2011.11.034

  日期：2012.2

  A straightforward procedure leading to the flavone cirsimaritin and its 4'-O-beta-D-glycosylation to afford cirsimarin, its corresponding flavone glucopyranoside, is described. The biological properties of cirsimarin, measured on human adipocytes, showed potent effects on both lipolysis and lipogenesis. Cirsimarin could therefore be considered as an efficient tool in the struggle against excessive adipose tissue deposition and as a potential candidate in the treatment of obesity. (C) 2011 Elsevier Ltd. All rights reserved.