望春花素 | 31008-18-1

• 物质功能分类: 天然产物 - 木脂素
• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 呋喃类木脂素
• 中文名称: 望春花素
• 中文别名: 木兰脂素
• 英文名称: Magnolin
• 英文别名: Medioresinol dimethyl ether；(3S,3aR,6S,6aR)-3-(3,4-dimethoxyphenyl)-6-(3,4,5-trimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan
• CAS: 31008-18-1
• 化学式: C₂₃H₂₈O₇
• 分子量: 416.471
• InChiKey: MFIHSKBTNZNJIK-RZTYQLBFSA-N

物化性质

• 熔点：
  91.4-92.9 °C
• 沸点：
  536.9±50.0 °C(Predicted)
• 密度：
  1.178±0.06 g/cm3(Predicted)
• 溶解度：
  氯仿（微溶）、乙酸乙酯（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

安全信息

• 安全说明：
  S24/25
• 海关编码：
  29329990
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

制备方法与用途

生物活性

Magnolin 是 Magnolia flos (辛夷) 的主要成分，靶向作用于 ERK1 和 ERK2。其 IC50 值分别为 87 nM 和 16.5 nM，从而抑制 Ras/ERKs/RSK2 信号通路。

靶点

Target	Value
ERK2	16.5 nM
ERK1	87 nM

体外研究

Magnolin 是一种广泛存在于木兰花中的天然化合物，传统上用于治疗头痛、鼻塞和抗炎反应。它通过靶向激活的 ERK1 和 ERK2 活性口袋来抑制这些重要的癌细胞转移信号分子。此外，Magnolin 还通过抑制 NF-κB 转录活化活性，阻断 ERKs/RSK2 信号通路。该化合物还通过抑制细胞增殖、转化和癌细胞转移的关键信号分子——外源性调节激酶（ERKs），从而减少肿瘤坏死因子-α (TNF-α) 和前列腺素 E2 (PGE2) 的产生。

Magnolin 能剂量依赖地抑制由表皮生长因子 (EGF) 治疗诱导的 JB6 Cl41 细胞迁移。它通过阻断 ERK1/2/RSK2 信号通路介导的 IκBα 在 Ser32 位点的磷酸化，从而抑制 NF-κB 活化和细胞迁移。

化学性质

白色结晶粉末，溶于氯仿。来源于木兰科辛夷（Magnolia denudata Desr）的花蕾。

用途

木兰脂素具有抗过敏、抗炎、降压及抑菌的作用，并可用于含量测定、鉴定和药理实验等。

反应信息

• 作为反应物：
  描述：

  望春花素 以 二甲基亚砜 为溶剂， 反应 42.0h， 以201 mg的产率得到(+)-de-4'-O-methyl-5'-hydroxymagnolin
  参考文献：
  名称：

  Biotransformation of lignans: a specific microbial oxidation of (+)-eudesmin and (+)-magnolin by Aspergillus niger

  摘要：

  Biotransformation of the lignans, (+)-eudesmin, (+)-magnolin and (+)-yangabin, by Aspergillus niger has been investigated. (+)-Eudesmin was metabolized and transformed to (+)-de-4'-0-methyleudesmin and (+)-pinoresinol. Additionally, (+)-pinoresinol was examined and oxidized to (+)-5'-hydroxypinoresinol. (+)-Magnolin was transformed to (+)-de-0-methylmagnolin and (+)-de-4'-0-methyl-5'-hydroxymagnolin. In these metabolic processes, other products were not generated, although(+)-yangabin and (+)-de-4'-0-methyl-5'-hydroxymagnolin were hardly metabolized by this fungus. This suggested that the veratryl and guaiacyl groups of these lignans were possibly metabolized preferentially, with oxidation proceeding predominantly through de-0-methylation at the p-position of veratryl groups. By contrast, 3,4,5-trimethoxyphenyl and 4,5-dihydroxy-3-methoxyphenyl groups of this type of lignan were stable and not attacked by A. niger. The structures of metabolic products were determined by spectroscopic methods as well as by comparison of spectral data with those of known related compounds.

  DOI：

  10.1016/s0031-9422(00)90836-7
• 作为产物：
  描述：

  (-)-magnofargesin acetate 在 盐酸 、 diborane(6) 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 4.5h， 生成 望春花素
  参考文献：
  名称：

  (-)-Magnofargesin 和 (+)-magnoliadiol，两种来自 Magnolia fargesii 的木脂素

  摘要：

  摘要 从厚朴的花蕾中分离到了两种新的木脂素，(-)-木脂素和(+)-木兰二醇。(-)-magnofargesin 的绝对构型分配是通过将其异构化为 (+)-magnolin 来实现的。

  DOI：

  10.1016/0031-9422(95)00879-9

文献信息

• COMPOSITION CONTAINING LIGNAN COMPOUND AS ACTIVE INGREDIENT FOR PREVENTING OR TREATING CANCER
  申请人：KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY

  公开号：US20160228402A1

  公开（公告）日：2016-08-11

  The present invention relates to a pharmaceutical composition for preventing, ameliorating, or treating cancer. More specifically, the present invention relates to a pharmaceutical composition for preventing or treating cancer including a lignan compound having a specific chemical structure (Chemical Formula 1); a health functional food composition for preventing or ameliorating cancer including the lignan compound; and a method for preventing, ameliorating, or treating cancer using the composition. Further, the present invention relates to a use of the lignan compound in the preparation of a pharmaceutical composition or a health functional food composition for preventing, ameliorating, or treating cancer.
• US9820963B2
  申请人：——

  公开号：US9820963B2

  公开（公告）日：2017-11-21
• Biotransformation of lignans: a specific microbial oxidation of (+)-eudesmin and (+)-magnolin by Aspergillus niger
  作者：Mitsuo Miyazawa、Hiroyuki Kasahara、Hiromu Kameoka

  DOI：10.1016/s0031-9422(00)90836-7

  日期：1993.12

  Biotransformation of the lignans, (+)-eudesmin, (+)-magnolin and (+)-yangabin, by Aspergillus niger has been investigated. (+)-Eudesmin was metabolized and transformed to (+)-de-4'-0-methyleudesmin and (+)-pinoresinol. Additionally, (+)-pinoresinol was examined and oxidized to (+)-5'-hydroxypinoresinol. (+)-Magnolin was transformed to (+)-de-0-methylmagnolin and (+)-de-4'-0-methyl-5'-hydroxymagnolin. In these metabolic processes, other products were not generated, although(+)-yangabin and (+)-de-4'-0-methyl-5'-hydroxymagnolin were hardly metabolized by this fungus. This suggested that the veratryl and guaiacyl groups of these lignans were possibly metabolized preferentially, with oxidation proceeding predominantly through de-0-methylation at the p-position of veratryl groups. By contrast, 3,4,5-trimethoxyphenyl and 4,5-dihydroxy-3-methoxyphenyl groups of this type of lignan were stable and not attacked by A. niger. The structures of metabolic products were determined by spectroscopic methods as well as by comparison of spectral data with those of known related compounds.
• (−)-Magnofargesin and (+)-magnoliadiol, two lignans from Magnolia fargesii
  作者：Mitsuo Miyazawa、Hiroyuki Kasahara、Hiromu Kameoka

  DOI：10.1016/0031-9422(95)00879-9

  日期：1996.5

  Abstract Two new lignans, (−)-magnofargesin and (+)-magnoliadiol, were isolated from the flower buds of Magnolia fargesii . The absolute configuration assignment of (−)-magnofargesin was achieved by its isomerization to (+)-magnolin.

  摘要 从厚朴的花蕾中分离到了两种新的木脂素，(-)-木脂素和(+)-木兰二醇。(-)-magnofargesin 的绝对构型分配是通过将其异构化为 (+)-magnolin 来实现的。