threo-4,7,9,9′-tetrahydroxy-3,3′-dimethoxy-8-O-4′-neolignan | 182211-72-9

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: threo-4,7,9,9′-tetrahydroxy-3,3′-dimethoxy-8-O-4′-neolignan
• 英文别名: threo 3-methoxy-8,4'-oxyneolignan-3',4,7,9,9'-pentol；(1R,2R)-2-[2-hydroxy-4-(3-hydroxypropyl)phenoxy]-1-(4-hydroxy-3-methoxyphenyl)propane-1,3-diol
• CAS: 182211-72-9
• 化学式: C₁₉H₂₄O₇
• 分子量: 364.395
• InChiKey: KMYQEVOSRSCASE-RTBURBONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  120
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  7R,8R-3,,4,7,9-tetrahydroxy-3-methoxy-8-O-4'-neolignan-9'-O-β-D-glucopyranoside 在 水 、 almond β-glucosidase 作用下， 反应 48.0h， 以1 mg的产率得到threo-4,7,9,9′-tetrahydroxy-3,3′-dimethoxy-8-O-4′-neolignan
  参考文献：
  名称：

  New Neolignan Component from Camellia amplexicaulis and Effects on Osteoblast Differentiation

  摘要：

  从文心山茶的叶子和枝条中分离出了一种名为 "山茶苷 A"（1）的新木脂素，以及七种已知的苷类化合物（2-8）。通过各种光谱分析确定了它们的结构。与对照组相比，化合物 2、3、4 和 6 能显著（p<0.05）提高碱性磷酸酶活性和 MC3T3-E1 成骨细胞结核的矿化度。

  DOI：

  10.1248/cpb.57.65

文献信息

• Studies on the Constituents of Lonicera Species. X. Neolignan Glycosides from the Leaves of Lonicera gracilipes var. glandulosa MAXIM.
  作者：Noriko MATSUDA、Masao KIKUCHI

  DOI：10.1248/cpb.44.1676

  日期：——

  Four new 8-O-4'-neolignan glycosides, 4, 9, 9'-trihydroxy-3, 3'-dimethoxy-8-O-4'-neolignan-7-O-β-D-glucopyranosides [7S, 8S-threo form (1) and 7S, 8R-erythro form (2)], 7R, 8R-threo-4, 7, 9, 9'-tetrahydroxy-3-methoxy-8-O-4'-neolignan-3'-O-β-D-glucopyranoside (3) and 7S, 8R-erythro-7, 9, 9'-trihydroxy-3, 3'-dimethoxy-8-O-4'-neolignan-4-O-β-D-glucopyranoside (4), and two known compunds, 4, 7, 9-trihydroxy-3, 3'-dimethoxy-8-O-4'-neolignan-9'-O-β-D-glucopyranosides [7R, 8R-threo form (5) and 7S, 8R-erythro form (6)], have been isolated from the leaves of Lonicera gracilipes var. glandulosa MAXIM. Their absolute stereostructures have been determined on the basis of spectral and chemical evidence.

  从细梗忍冬腺叶变种的叶子中分离得到4个新的8-O-4'-新木脂素苷，4，9，9'-三羟基-3，3'-二甲氧基-8-O-4'-新木脂素-7-O-β-D-吡喃葡萄糖苷[7S，8S-苏式异构体(1)和7S，8R-赤式异构体(2)]，7R，8R-苏式-4，7，9，9'-四羟基-3-甲氧基-8-O-4'-新木脂素-3'-O-β-D-吡喃葡萄糖苷(3)和7S，8R-赤式-7，9，9'-三羟基-3，3'-二甲氧基-8-O-4'-新木脂素-4-O-β-D-吡喃葡萄糖苷(4)，以及2个已知化合物，4，7，9-三羟基-3，3'-二甲氧基-8-O-4'-新木脂素-9'-O-β-D-吡喃葡萄糖苷[7R，8R-苏式异构体(5)和7S，8R-赤式异构体(6)]。根据光谱和化学证据确定了这些化合物的绝对构型。
• New Neolignan Component from Camellia amplexicaulis and Effects on Osteoblast Differentiation
  作者：Nguyen Huu Tung、Yan Ding、Eun Mi Choi、Chau Van Minh、Young Ho Kim

  DOI：10.1248/cpb.57.65

  日期：——

  A new neolignan named “camellioside A” (1) has been isolated from the leaves and branches of Camellia amplexicaulis, along with seven known glycosides (2—8). Their structures were determined by a variety of spectroscopic analyses. Among them, compounds 2, 3, 4, and 6 significantly (p<0.05) increased the alkaline phosphatase activity and the mineralization of the nodules of the MC3T3-E1 osteoblastic cells compared to those of the control.

  从文心山茶的叶子和枝条中分离出了一种名为 "山茶苷 A"（1）的新木脂素，以及七种已知的苷类化合物（2-8）。通过各种光谱分析确定了它们的结构。与对照组相比，化合物 2、3、4 和 6 能显著（p<0.05）提高碱性磷酸酶活性和 MC3T3-E1 成骨细胞结核的矿化度。