(12R)-2-oxatricyclo[13.2.2.13,7]icosa-3,5,7(20),15,17,18-hexaene-4,12-diol | 60503-28-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (12R)-2-oxatricyclo[13.2.2.13,7]icosa-3,5,7(20),15,17,18-hexaene-4,12-diol
• 英文别名: acerogenin A；(12R)-2-oxatricyclo[13.2.2.13,7]eicosa-3,5,7(20),15,17,18-hexaene-4,12-diol；(12R)-2-oxatricyclo[13.2.2.13,7]icosa-1(17),3,5,7(20),15,18-hexaene-4,12-diol
• CAS: 60503-28-8
• 化学式: C₁₉H₂₂O₃
• 分子量: 298.382
• InChiKey: JHRMYLCWJWLUQL-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (12R)-2-oxatricyclo[13.2.2.13,7]icosa-3,5,7(20),15,17,18-hexaene-4,12-diol 在 对甲苯磺酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲苯 、 甲醇 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 2.0h， 以17 mg的产率得到11-dehydroxy acerogenin A
  参考文献：
  名称：

  Cyclic diarylheptanoids as inhibitors of NO production from Acer nikoense

  摘要：

  我们制备了一系列金合欢苷 A 和 B 衍生物，作为体外一氧化氮（NO）产生的抑制剂。我们的研究结果表明，C-2羟基上的酯基提高了抑制效果，且无细胞毒性。芹菜甙元 C 的苯甲酰基酯类衍生物对脂多糖激活的巨噬细胞产生的一氧化氮具有最强的抑制活性。

  DOI：

  10.1007/s11418-012-0660-0
• 作为产物：
  描述：

  aceroside I 在 盐酸 、 甲醇 作用下， 反应 2.0h， 以185 mg的产率得到(12R)-2-oxatricyclo[13.2.2.13,7]icosa-3,5,7(20),15,17,18-hexaene-4,12-diol
  参考文献：
  名称：

  槭树树皮中二芳基庚烷类化合物及其衍生物的黑色素生成抑制和细胞毒活性

  摘要：

  九种环状二芳基庚烷类化合物，1-9，包括两种新化合物，即 9-氧代角化菌素 A (8) 和 9-O-β-D-吡喃葡萄糖苷酯生成素 K (9)，以及三个非环状二芳基庚烷类化合物，10-12 和四个酚类从 Acer nikoense (Aceraceae) 树皮的甲醇提取物中分离出化合物 13-16。9 的酸水解产生 acerogenin K (17) 和 D-葡萄糖。两种环状二芳基庚烷类化合物，acerogenin A (1) 和 (R)-acerogenin B (5)，分别转化为它们的醚和酯​​衍生物，18-24 和 27-33，以及脱水衍生物，25, 26 , 34, 和 35. 在评估化合物 1-16 和 18-35 对 B16 黑色素瘤细胞黑色素生成的抑制活性时，α-黑色素细胞刺激素 (α-MSH)、八种天然糖苷，即六种二芳基庚烷糖苷，2-4、6、9 和 12，和两种酚苷，15 和

  DOI：

  10.1002/cbdv.201200024

文献信息

• Cyclic diarylheptanoids as Na+-glucose cotransporter (SGLT) inhibitors from Acer nikoense
  作者：Hiroshi Morita、Jun Deguchi、Yusuke Motegi、Seizo Sato、Chihiro Aoyama、Jiro Takeo、Motoo Shiro、Yusuke Hirasawa

  DOI：10.1016/j.bmcl.2009.12.036

  日期：2010.2

  Two cyclic diarylheptanoids, acerogenins A (1) and B (2) have been isolated from the bark of Acer nikoense as inhibitors of Na+-glucose cotransporter (SGLT). Acerogenins A (1) and B (2) inhibited both isoforms, SGLT1 and SGLT2. Structure–activity relationship of acerogenin derivatives on inhibitory activity of SGLT as well as conformational analysis of 1 and 2 on the basis of J-resolved HMBC spectra

  两种环二芳基庚烷类化合物，铜绿蛋白原A（1）和B（2）已从Acer nikoense的树皮中分离出来，作为Na + -葡萄糖共转运蛋白（SGLT）的抑制剂。Acerogenins A（1）和B（2）均抑制SGLT1和SGLT2这两种同工型。讨论了铜绿皂苷元衍生物对SGLT抑制活性的构效关系，并基于J解析的HMBC光谱和X射线分析对1和2进行了构象分析。
• Structures of New Cyclic Diarylheptanoids and Inhibitors of Nitric Oxide Production from Japanese Folk Medicine <i>Acer </i><i>n</i><i>ikoense</i>
  作者：Toshio Morikawa、Jing Tao、Iwao Toguchida、Hisashi Matsuda、Masayuki Yoshikawa

  DOI：10.1021/np020351m

  日期：2003.1.1

  cyclic diarylheptanoids, acerosides B1 and B2 and aceroketoside, were isolated together with 20 known compounds from a Japanese folk medicine, the stem bark of Acer nikoense. The absolute stereostructures of the new compounds were determined on the basis of chemical and physicochemical evidence. In addition, the principal diarylheptanoid constituents were found to exhibit inhibitory activity on nitric

  三种新的环状二芳基庚烷类化合物，乙酰胺类B1和B2和刺柏苷，与20种已知化合物一起从日本民间药物中分离，即日本槭树的茎皮。根据化学和物理化学证据确定了新化合物的绝对立体结构。此外，发现主要的二芳基庚烷成分对脂多糖激活的巨噬细胞中一氧化氮的产生具有抑制活性。
• PHARMACEUTICAL COMPOSITION FOR PREVENTION AND/OR TREATMENT OF BONE DISEASE, FUNCTIONAL FOOD OR HEALTH FOOD COMPRISING THE COMPOSITION, AND PHARMACEUTICAL PREPARATION COMPRISING THE COMPOSITION AS ACTIVE INGREDIENT
  申请人：Akihisa, Toshihiro

  公开号：EP2050442A1

  公开（公告）日：2009-04-22

  The present invention provides a highly safe pharmaceutical composition for preventing and/or treating bone disease, a pharmaceutical preparation comprising thereof, a health food comprising thereof, a functional food comprising thereof. Since the present invention comprises the arylheptanoid compound shown in the following formula (I) and the derivatives thereof, it enables to prevent and/or treat the bone disease. (In the formula (I), R1 and R5 are a functional group selected from the group consisting of a hydrogen atom, alkyl group having carbon numbers 1 to 3, monosaccharide and disaccharide; R2, R3, and R4 are a functional group selected from the group consisting of a hydrogen atom, an oxygen atom, alkyl group having carbon numbers 1 to 3, monosaccharide and disaccharide; R5 may be bound on meta-position against heptylene group of another aryl group to form a ring.)

  本发明提供了一种用于预防和/或治疗骨病的高安全性药物组合物、由其组成的药物制剂、由其组成的保健食品、由其组成的功能性食品。由于本发明包含下式（I）所示的芳基庚烷类化合物及其衍生物，因此能够预防和/或治疗骨病。 (在式(I)中，R1和R5是选自氢原子、碳原子数为1至3的烷基、单糖和二糖的官能团；R2、R3和R4是选自氢原子、氧原子、碳原子数为1至3的烷基、单糖和二糖的官能团；R5可与另一芳基的庚基在元位置上结合形成环)。
• Pharmaceutical composition for prevention and/or treatment of bone disease, functional food or health food comprising the composition, and pharmaceutical preparation comprising the composition as active ingredient
  申请人：Akihisa, Toshihiro

  公开号：EP2407160A1

  公开（公告）日：2012-01-18

  The present invention provides a highly safe pharmaceutical composition for preventing and/or treating bone disease, a pharmaceutical preparation comprising thereof, a health food comprising thereof, a functional food comprising thereof. Since the present invention comprises the arylheptanoid compound shown in the following formula (I) and the derivatives thereof, it enables to prevent and/or treat the bone disease. (In the formula (I), R1 and R5 are a functional group selected from the group consisting of a hydrogen atom, alkyl group having carbon numbers 1 to 3, monosaccharide and disaccharide; R2, R3, and R4 are a functional group selected from the group consisting of a hydrogen atom, an oxygen atom, alkyl group having carbon numbers 1 to 3, monosaccharide and disaccharide; R5 may be bound on meta-position against heptylene group of another aryl group to form a ring.)

  本发明提供了一种用于预防和/或治疗骨病的高安全性药物组合物、由其组成的药物制剂、由其组成的保健食品、由其组成的功能性食品。由于本发明包含下式（I）所示的芳基庚烷类化合物及其衍生物，因此能够预防和/或治疗骨病。 (在式(I)中，R1和R5是选自氢原子、碳原子数为1至3的烷基、单糖和二糖的官能团；R2、R3和R4是选自氢原子、氧原子、碳原子数为1至3的烷基、单糖和二糖的官能团；R5可与另一芳基的庚基在元位置上结合形成环)。
• PHARMACEUTICAL COMPOSITION FOR PREVENTING AND/OR TREATING BONE DISEASE, FUNCTIONAL FOOD OR HEALTH FOOD AND PHARMACEUTICAL PREPARATION COMPRISING THEREOF AS ACTIVE INGREDIENT
  申请人：Woo Je-Tae

  公开号：US20090227527A1

  公开（公告）日：2009-09-10

  The present invention provides a highly safe pharmaceutical composition for preventing and/or treating bone disease, a pharmaceutical preparation comprising thereof, a health food comprising thereof, a functional food comprising thereof. Since the present invention comprises the arylheptanoid compound shown in the following formula (I) and the derivatives thereof, it enables to prevent and/or treat the bone disease. (In the formula (I), R 1 and R 5 are a functional group selected from the group consisting of a hydrogen atom, alkyl group having carbon numbers 1 to 3, monosaccharide and disaccharide; R 2 , R 3 , and R 4 are a functional group selected from the group consisting of a hydrogen atom, an oxygen atom, alkyl group having carbon numbers 1 to 3, monosaccharide and disaccharide; R 5 may be bound on meta-position against heptylene group of another aryl group to form a ring.)