异甜菊醇内酯 | 23963-60-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: 异甜菊醇内酯
• 英文名称: 4α-carboxy-13α-hydroxy-13,16-seco-ent-19-norbeyeran-16-oic acid lactone
• 英文别名: (1R,4S,5R,9S,10R,13S)-5,9,13-trimethyl-15-oxo-14-oxatetracyclo[11.3.1.0^1,10.0^4,9]heptadecane-5-carboxylic acid；ent-16-lactone-beyeran-19-oic acid；4α-carboxy-13α-hydroxy-13,16-seco-ent-norbeyeran-19-oic acid；ent-8α-Carboxymethyl-13α-hydroxy-13β-methylpodocarpan-19-saeurelacton；4α-carboxy-13α-hydroxy-13,16-seco-ent-19-norbeyeran-16-oic acid 13,16-lactone；isosteviol lactone；(1R,4S,5R,9S,10R,13S)-5,9,13-trimethyl-15-oxo-14-oxatetracyclo[11.3.1.01,10.04,9]heptadecane-5-carboxylic acid
• CAS: 23963-60-2
• 化学式: C₂₀H₃₀O₄
• 分子量: 334.456
• InChiKey: OLJRAFPOAGIZKX-XGBBNYNSSA-N

物化性质

• 熔点：
  264-265 °C
• 沸点：
  499.5±45.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 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：

  异甜菊醇内酯 在 氯化亚砜 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 9.0h， 生成
  参考文献：
  名称：

  Synthesis and cytotoxic activity of nitric oxide-releasing isosteviol derivatives

  摘要：

  Fifteen novel hybrids containing diterpene skeleton and nitric oxide (NO) donor were prepared from isosteviol. All the compounds were tested on preliminary cytotoxicity, and the results showed that six target compounds (8c, 10b, 14a, 14c, 18c, and 18d) exhibited anti-proliferation activity on HepG2 cells, with 8c (IC50 = 4.24 mu M) and 18d (IC50 = 2.75 mu M) superior to the positive control CDDO-Me (2-cyano-3,12-dioxo-oleana-1,9(11)-dien-28-acid methyl ester, IC50 = 4.99 mu M); eleven target compounds(8a-c, 9a-c, 10a-b, 14a, 14c, 18d) exhibited anti-proliferation activities on B16F10 cells at different levels, among them, seven compounds were more potent than comptothecin (IC50 = 2.78 mu M) and CDDO-Me (IC50 = 5.85 mu M), particularly, 10b (IC50 = 0.02 mu M) presented the strongest effect, which was selected as a candidate for further study. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.004
• 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， 以30%的产率得到异甜菊醇内酯
  参考文献：
  名称：

  Ent-beyerene 和 Ent-kaurene 衍生物的合成、细胞毒性和利什曼原虫评估

  摘要：

  描述了甜味剂甜叶菊的ent- beyerene 和ent- kaurene 衍生物的合成，包括细胞毒性测试和对巴西利什曼原虫的体外活性，巴西利什曼原虫是美国皮肤利什曼病的最主要形式。39 种合成化合物中有 21 种显示出高杀利什曼原虫活性，即使浓度低于 10 mM

  DOI：

  10.1002/ejoc.202001424

文献信息

• Biogenetic-like rearrangements of isosteviol derivatives: π-route to the atiserene system
  作者：Robert M. Coates、Edward F. Bertram

  DOI：10.1039/c29690000797

  日期：——

  Solvolytic cyclization of the unsaturated tricyclic toluene-p-sulphonate (IV) affords the atiseran-13-ol derivative (VI), which at higher temperature undergoes Wagner–Meerwein rearrangement to the hibaan-12-ol isomer (IX).

  不饱和三环甲苯对磺酸盐的溶剂化环化反应（IV）提供了atiseran-13-ol衍生物（VI），该衍生物在较高的温度下经历了Wagner-Meerwein重排为hibaan-12-ol异构体（IX）。
• Synthesis and pharmacological profile of serofendic acids A and B
  作者：Taro Terauchi、Naoki Asai、Takashi Doko、Ryota Taguchi、Osamu Takenaka、Hideki Sakurai、Masahiro Yonaga、Teiji Kimura、Akiharu Kajiwara、Tetsuhiro Niidome、Toshiaki Kume、Akinori Akaike、Hachiro Sugimoto

  DOI：10.1016/j.bmc.2007.07.037

  日期：2007.11

  We present efficient syntheses of serofendic acids A and B (SA-A and SA-B), novel neuroprotective substances isolated from fetal calf serum. Biological and pharmacological evaluation showed that SA-A and SA-B have potent protective action aaainst glutarnate-induced neurotoxicity, but do not interact directly with glutamate receptors. A pharmacokinetic study showed that they have good oral bioavailability in rats. The results indicate that SA-A and SA-B are potential lead compounds for candidate drugs to treat various neuroloaical disorders. (C) 2007 Elsevier Ltd. All rights reserved.
• Structural modifications of isosteviol. Partial synthesis of atiserene and isoatiserene
  作者：Robert M. Coates、Edward F. Bertram

  DOI：10.1021/jo00817a014

  日期：1971.9
• 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.
• Transformation of isosteviol oxime to a lactone under Beckmann reaction conditions
  作者：Olesya I. Militsina、Galina I. Kovyljaeva、Galina A. Bakaleynik、Irina Yu. Strobykina、Vladimir E. Kataev、Vladimir A. Alfonsov、Rashid Z. Musin、Dmitry V. Beskrovny、Igor A. Litvinov

  DOI：10.1070/mc2005v015n01abeh001946

  日期：2005.1

  Heating the 16-E-oxime of isosteviol (ent-16-E-hydroxyiminobeyeran-19-oic acid) with concentrated hydrochloric acid (or 25% H2SO4) at 110 degreesC leads to the formation of lactone of 4alpha-carboxy-13alpha-hydroxy-13,16-seco-ent-19-norbeyeran-16-oic acid as the main product, whereas approximately equal quantities of this lactone and lactam of 4alpha-carboxy- 13alpha-amino- 13,16- seco-ent-19 norbeyeran-16-oic acid are formed by heating the 16-E-oxime of isosteviol with concentrated hydrochloric acid in an ampoule at 180 degreesC.