4α-carboxy-15α-hydroxy-15,16-seco-ent-19-norbeyeran-16-oic acid 15,16-lactone | 89470-25-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 4α-carboxy-15α-hydroxy-15,16-seco-ent-19-norbeyeran-16-oic acid 15,16-lactone
• 英文别名: (1S,4S,5R,9S,10S,13S)-5,9,13-trimethyl-14-oxo-15-oxatetracyclo[11.3.1.01,10.04,9]heptadecane-5-carboxylic acid
• CAS: 89470-25-7
• 化学式: C₂₀H₃₀O₄
• 分子量: 334.456
• InChiKey: FUMGUTQYADOMBS-XYTVEFIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 4α-carboxy-15α-hydroxy-15,16-seco-ent-19-norbeyeran-16-oic acid 15,16-lactone 生成
  参考文献：
  名称：

  Kapadi, A. H.; Dev, Sukh, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 10, p. 970 - 977

  摘要：

  DOI：
• 作为产物：
  描述：

  异甜菊醇 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以60%的产率得到4α-carboxy-15α-hydroxy-15,16-seco-ent-19-norbeyeran-16-oic acid 15,16-lactone
  参考文献：
  名称：

  Stereoselective synthesis of bioactive isosteviol derivatives as α-glucosidase inhibitors

  摘要：

  Considerable interest has been attracted in isosteviol and its derivatives because of their large variety of pharmacological activities. In this project, a series of novel compounds containing hydroxyl, hydroxymethyl group and heteroatom-containing frameworks fused with isosteviol structure were synthesized and evaluated as alpha-glucosidase inhibitors, aimed at clarifying the structure-activity correlation. The results indicated that these isosteviol derivatives were capable of inhibiting in vitro alpha-glucosidase with moderate to good activities. Among them, indole derivative 15b exhibited the highest activities and thus may be exploitable as a lead compound for the development of potent alpha-glucosidase inhibitors. (c) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2009.01.017

文献信息

• Microbial Transformation of Isosteviol Lactone and Evaluation of the Transformation Products on Androgen Response Element
  作者：Bo-Hon Chou、Li-Ming Yang、Shwu-Fen Chang、Feng-Lin Hsu、Chia-Hsin Lo、Jia-Horng Liaw、Pan-Chun Liu、Shwu-Jiuan Lin

  DOI：10.1021/np070585b

  日期：2008.4.1

  Two filamentous fungi, Cunninghamella bainieri ATCC 9244 and Aspergillus niger BCRC 32720, were used to investigate the biotransformation of isosteviol lactone (4 alpha-carboxy-13 alpha-hydroxy-13,16-seco-ent-19-norbeyeran-16-oic acid 13,16-lactone) (2), which was derived by reacting isosteviol (ent-16-oxobeyeran-19-oic acid) (1) with m-chloroperbenzoic acid. Incubation of 2 with C. bainieri afforded metabolites 3-6, which involved isomerization, hydroxylation, and ring cleavage reactions followed by oxidation and selective O-methylation. Incubation of 2 with A. niger afforded mono-, di-, and trihydroxylated metabolites 3, 4, and 7-12. The structures of 3-12 were elucidated on the basis of spectroscopic analyses, and structures 3, 4, and 6 were confirmed by X-ray crystallographic studies. Compounds 2-6, 8-10, and 12 were assayed as androgen agonists using an ARE (androgen response element)-mediated luciferase reporter gene assay. Compounds 3, 6, and 10 were significantly active, with 6 showing more activity than testosterone.
• Fungal transformation of isosteviol lactone and its biological evaluation for inhibiting the AP-1 transcription factor
  作者：Bo-Hon Chou、Li-Ming Yang、Shwu-Fen Chang、Feng-Lin Hsu、Chia-Hsin Lo、Wen-Kuang Lin、Li-Hsuan Wang、Pan-Chun Liu、Shwu-Jiuan Lin

  DOI：10.1016/j.phytochem.2009.03.015

  日期：2009.4

  A number of hydroxylated diterpenoids were obtained from the microbial transformation of isosteviol lactone (4 alpha-carboxy-13 alpha-hydroxy-13,16-seco-ent-19-norbeyeran-16-oic acid 13,16-lactone) (2) with Mucor recurvatus MR 36, Aspergillus niger BCRC 31130, and Absidia pseudocylindrospora ATCC 24169. Incubation of 2 with M. recurvatus and Asp. niger led to isolation of seven known compounds (1 and 3-8). Incubation of 2 with Abs. pseudocylindrospora produced 5 and six previously unreported compounds (9-14). The structures of these isolated compounds were deduced by high-field NMR techniques (H-1, C-13, DEPT, COSY, NOESY, HSQC, and HMBC), and those of 9 and 11 were further confirmed by X-ray crystallographic analyses. Subsequently, the inhibitory effects on activator protein-1 (AP-1) activation in lipo-polysaccharide-stimulated RAW 264.7 macrophages of all of these compounds were evaluated. Compounds 2-5, 8, 9, 11, and 12 exhibited significant inhibitory activity, while 3 was more potent than the reference compound of dexamethasone. (C) 2009 Elsevier Ltd. All rights reserved.
• Stereoselective synthesis of bioactive isosteviol derivatives as α-glucosidase inhibitors
  作者：Ya Wu、Jing-Hua Yang、Gui-Fu Dai、Cong-Jun Liu、Guo-Qiang Tian、Wen-Yan Ma、Jing-Chao Tao

  DOI：10.1016/j.bmc.2009.01.017

  日期：2009.2

  Considerable interest has been attracted in isosteviol and its derivatives because of their large variety of pharmacological activities. In this project, a series of novel compounds containing hydroxyl, hydroxymethyl group and heteroatom-containing frameworks fused with isosteviol structure were synthesized and evaluated as alpha-glucosidase inhibitors, aimed at clarifying the structure-activity correlation. The results indicated that these isosteviol derivatives were capable of inhibiting in vitro alpha-glucosidase with moderate to good activities. Among them, indole derivative 15b exhibited the highest activities and thus may be exploitable as a lead compound for the development of potent alpha-glucosidase inhibitors. (c) 2009 Published by Elsevier Ltd.
• Kapadi, A. H.; Dev, Sukh, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 10, p. 970 - 977
  作者：Kapadi, A. H.、Dev, Sukh

  DOI：——

  日期：——