moracinoside M | 1117776-98-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: moracinoside M
• 英文别名: 5-[2,3-epoxy-3-methylbutyl]-3'-O-β-D-xylopyranosyl-6,5'-dihydroxy-2-phenylbenzofuran；(2S,3R,4S,5R)-2-[3-[5-[(3,3-dimethyloxiran-2-yl)methyl]-6-hydroxy-1-benzofuran-2-yl]-5-hydroxyphenoxy]oxane-3,4,5-triol
• CAS: 1117776-98-3
• 化学式: C₂₄H₂₆O₉
• 分子量: 458.465
• InChiKey: CXFWUUIIDNGHQH-ZGMXMJJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  145
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  moracinoside M 在 水 作用下， 生成 beta-D-吡喃木糖
  参考文献：
  名称：

  Tyrosinase Inhibitory Polyphenols from Roots ofMorus lhou

  摘要：

  Twelve polyphenols (1-12) possessing tyrosinase inhibitory properties were isolated from the methanol (95%) extract of Morus Ihou. The isolated compounds consisted of four flavanones (1-4), four flavones (5-8), and four phenylbenzofuranes (9-12). Moracin derivative 12 proved to be new a compound which was fully characterized. Compounds 1-12 were evaluated for both monophenolase and diphenolase (the two steps catalyzed by tyrosinase) inhibition to identify the structural characteristics required for mushroom tyrosinase inhibition. We observed that all parent compounds (1, 5, and 9) possessing an unsubstituted resorcinol group were highly effective inhibitors of monophenolase activity (IC50 values of 1.3, 1.2, and 7.4 mu M). The potency of the inhibitors diminished with alkyl substitution on either the aromatic ring or the hydroxyl functions. Interestingly, flavone 5 was shown to possess only monophenolase inhibitory activity, but flavanone 1 and phenylbenzofuran 9 inhibited diphenolase as well as monophenolase significantly. The inhibitory mode of these species was also dependent upon the skeleton: phenylbenzofuran 9 manifested a simple competitive inhibition mode for monophenolase and diphenolase; on the other hand flavanone 1 (monophenolase, k(3) = 0. 1966 min(-1) mu M-1, k(4) = 0.0082 min(-1), and K-i(app) = 0.0468 mu M; diphenolase, k(3) = 0.0014 min(-1) mu M-1, k(4) = 0.0013 min(-1), and K-i(app) = 0.8996 mu M) and flavone 5 both showed time-dependent inhibition against monophenolase. Compound 1 operated according to the simple reversible slow binding model whereas compound 5 operated under the enzyme isomerization model.

  DOI：

  10.1021/jf8033286