morroniside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: morroniside
• 英文别名: methyl (1S,4aS,8S,8aS)-3-hydroxy-1-methyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,3,4,4a,8,8a-hexahydropyrano[3,4-c]pyran-5-carboxylate
• 化学式: C₁₇H₂₆O₁₁
• 分子量: 406.387
• InChiKey: YTZSBJLNMIQROD-KKORFXOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  164
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  morroniside 在 盐酸 作用下， 以 水 为溶剂， 反应 3.0h， 生成 D-葡萄糖
  参考文献：
  名称：

  菖蒲根茎和山茱萸果实的四对互变异构体

  摘要：

  从菖蒲根茎中分离得到一对新的愈创木烷型倍半萜互变异构体(1)。同时，三对已知化合物，包括一对二氢黄酮糖苷互变异构体......

  DOI：

  10.1080/14786419.2022.2119969
• 作为产物：
  描述：

  methyl (1S,4aS,8S,8aS)-8-[(2S,3R,4S,5S,6R)-6-[[(2R)-3-(3,4-dimethoxybenzoyl)oxy-2-methylpropanoyl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-3-hydroxy-1-methyl-1,3,4,4a,8,8a-hexahydropyrano[3,4-c]pyran-5-carboxylate 生成 morroniside
  参考文献：
  名称：

  GARCIA, JULIAN;MPONDO, MPONDO EMMANUEL;CARTIER, GILBERT;GEY, CLAUDE, J. NATUR. PROD., 52,(1989) N, C. 996-1002

  摘要：

  DOI：

文献信息

• Iodine-Catalyzed Etherification of Morroniside
  作者：Fortunatus Sunghwa、Hiroaki Sakurai、Ikuo Saiki、Mamoru Koketsu

  DOI：10.1248/cpb.57.112

  日期：——

  In this study, we describe a highly selective etherification procedure of unprotected morroniside catalyzed by molecular iodine in acetone. The etherification reaction furnished 7-O-alkyl ether derivatives in reasonable yields within few hours under neutral conditions. Studies of the obtained products on cytotoxicity activity in colon 26-L5 cell line were examined. Among the tested compounds, 7-O-dodecylmorroniside showed moderate cytotoxic activity, having IC50 values equal to 20.9 μM.

  在本研究中，我们描述了一种在丙酮中通过分子碘催化无保护基的毛蕊花糖苷进行高度选择性的醚化方法。在中性条件下，醚化反应在几小时内以合理的产率制备了7-O-烷基醚衍生物。对获得的产品在结肠26-L5细胞系中的细胞毒性活性进行了研究。在测试的化合物中，7-O-十二烷基毛蕊花糖苷表现出中等的细胞毒性活性，其IC50值等于20.9微摩尔。
• Intermediacy of 6-hydroxyloganin in the ring cleavage course of loganin to secologanin
  作者：Kenichiro Inoue、Takao Tanahashi、Hiroyuki Inouye、Hiroshi Kuwajima、Kiyokazu Takaishi

  DOI：10.1016/0031-9422(89)80263-8

  日期：1989.1

  Abstract A possible biosynthetic pathway from loganin to secologanin through ring cleavage of 6-hydroxyloganin was ruled out in feeding experiments in which Eustoma russellianum , Swertia japonica , Lonicera morrowii and Adina pilulifera were each presented with three C-6 and C-7 stereoisomers of 6-hydroxy [7- 2 H] loganin as well as [6,6,7,8- 2 H 4 ] - and [6,6,7,8 carbomethoxy- 2 H 7 ]-loganin. In

  摘要 在饲喂实验中排除了从马钱素通过 6-羟基马钱素的环裂解到赛洛加宁的可能生物合成途径，其中罗素、獐牙、忍冬和阿迪娜分别具有 6 种 C-6 和 C-7 立体异构体。 -羟基[7- 2 H]马钱素以及[6,6,7,8- 2 H 4 ] - 和[6,6,7,8 甲氧基-2 H 7 ]-马钱素。在相关实验中，导致 seroside 的 secologanin 醛基的还原被证明是通过来自 si 面的氢化物离子攻击进行的。
• Seto,M. et al., Chemical and pharmaceutical bulletin, 1976, vol. 24, p. 1393 - 1397
  作者：Seto,M. et al.

  DOI：——

  日期：——
• Morroniside cinnamic acid conjugate as an anti-inflammatory agent
  作者：Yoshinori Takeda、Naomi Tanigawa、Fortunatus Sunghwa、Masayuki Ninomiya、Makoto Hagiwara、Kenji Matsushita、Mamoru Koketsu

  DOI：10.1016/j.bmcl.2010.06.095

  日期：2010.8

  A morroniside cinnamic acid conjugate was prepared and evaluated on E-selectin mediated cell-cell adhesion as an important role in inflammatory processes. 7-O-Cinnamoylmorroniside exhibited excellent anti-inflammatory activity (IC(50) = 49.3 mu M) by inhibiting the expression of E-selectin; further, it was more active than another cinnamic-acid-conjugated iridoid glycoside (harpagoside; IC(50) = 88.2 mu M), 7-O-methylmorroniside, and morroniside itself. As a result, 7-O-cinnamoylmorroniside was observed to be a potent inhibitor of TNF-alpha-induced E-selectin expression. (c) 2010 Elsevier Ltd. All rights reserved.
• GARCIA, JULIAN;MPONDO, MPONDO EMMANUEL;CARTIER, GILBERT;GEY, CLAUDE, J. NATUR. PROD., 52,(1989) N, C. 996-1002
  作者：GARCIA, JULIAN、MPONDO, MPONDO EMMANUEL、CARTIER, GILBERT、GEY, CLAUDE

  DOI：——

  日期：——