15β–acetoxy–(–)–kaur–16–en–l9–oic acid | 6619-97-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 15β–acetoxy–(–)–kaur–16–en–l9–oic acid
• 英文别名: ent-15-β-acetyloxy-kaur-16-en-19-oic acid；xylopic acid；(10S)-15β-acetoxy-kaur-16-en-19-oic acid；(10S)-15β-Acetoxy-kaur-16-en-19-saeure；Xylopsaeure；(1R,4S,5R,9S,10S,13R,15R)-15-Acetyloxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid
• CAS: 6619-97-2
• 化学式: C₂₂H₃₂O₄
• 分子量: 360.494
• InChiKey: AQBQBBLJTDSVLC-XNAIKIDQSA-N

物化性质

• 熔点：
  265-266 °C
• 沸点：
  475.1±45.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  15β–acetoxy–(–)–kaur–16–en–l9–oic acid 在 potassium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 12.5h， 生成 Methyl 15β-hydroxy-ent-kaur-16-en-19-oate
  参考文献：
  名称：

  Synthesis,in vitroAntimalarial Activity andin silicoStudies of Hybrid Kauranoid 1,2,3-Triazoles Derived from Naturally Occurring Diterpenes

  摘要：

  We herein report the synthesis of hybrid kauranoid molecules of type 1,2,3-triazole-1,4-disubstituted aiming to improve the antimalarial activity of kaurenoic and xylopic acids. The Cu-I-catalyzed cycloaddition of azides and kauranoid terminal alkynes was explored as a hybridization strategy. Kauranoid terminal alkynes were prepared from kaurenoic and xylopic acids that were isolated from Wedelia paludosa D. C. (Asteraceae) and Xylopia frutescens Aubl. (Annonaceae). A total of 15 kauranoid derivatives, including nine new triazoles, were obtained and five out of these were more active than the original diterpenes. Interestingly, an increased activity was observed for a kauranoid propargyl ether. Interaction between ent-kaurane diterpene derivatives and Ca2+-ATPase (PfATP6) was investigated. Synthesis of diterpene derivatives emerges as a possible route to be explored in the quest of potentially new inhibitors of PfATP6.

  DOI：

  10.5935/0103-5053.20150287

文献信息

• Chemistry of the constituents of Xylopia aethiopica. The structure of xylopic acid, a new diterpene acid
  作者：D. E. U. Ekong、A. U. Ogan

  DOI：10.1039/j39680000311

  日期：——

  From the dried fruits of Xylopia aethiopica has been isolated a new diterpene acid, xylopic acid, which is shown to be 15β-acetoxy-(–)-kaur-16-en-19-oic acid.

  从的干果Xylopia马蹄莲已分离出一种新的二萜酸，xylopic酸，其被示出为15β乙酰氧基- （ - ） -考尔-16-烯-19-酸。
• Fluorinated kaurenoids. Part 2. Preparation of methyl ent-17,17,17-trifluorokaur-15-en-19-oate and ent-16,16-difluoro-17-norkauran-19-oic acid from xylopic acid
  作者：Brian E. Cross、Anton Erasmuson、Paolino Filippone

  DOI：10.1039/p19810001293

  日期：——

  An attempt to convert methyl ent-16-oxo-17-norkauran-19-oate (3), derived from xylopic acid, into methyl ent-17,17-difluorokaur-16-en-19-oate failed. However, treatment of the norketone (3) with diethylaminosulphur trifluoride (DAST) gave methyl ent-16,16-difluoro-17-norkauran-19-oate (5). The latter afforded the corresponding acid (4) which was active as a growth promoter in a dwarf-rice bioassay

  尝试将源自木糖二酸的ent甲基-16-oxo-17-norkauran-19-oate（3）转换为ent -1,17-difluorokaur-16-en-19-oate甲基戊酸。然而，治疗norketone（3）用二乙基三氟化硫（DAST）的给甲基ENT -16,16二氟-17- norkauran-19 -酸酯（5）。后者提供了相应的酸（4），在矮米生物测定中可作为生长促进剂起作用。甲基deacetylxylopate（18）与DAST，然后由终端亚甲基的裂解处理，得到甲基ENT -15-氟-16-氧代-17- norkauran-19 -酸酯（15），其与二溴二氟甲烷和三（反应二甲基氨基）膦，得到，而不是预期的17,17-二氟烯烃（19），但甲基ENT-17,17,17-trifluorokaur-15-en-19-oate（28）收率不佳。用二酰亚胺还原草酰氯甲酯可立体定向得到16
• The biotransformation of ent-15-oxokaur-16-en-19-oic acid and its methyl ester by Cephalosporium aphidicola
  作者：Alaide B. de Oliveira、James R. Hanson、Jacqueline A. Takahashi

  DOI：10.1016/0031-9422(95)00289-j

  日期：1995.9

  ent-15-Oxokaur-16-en-19-oic acid and its methyl ester are transformed to ent-11α,16β-dihydroxy-15-oxokauran-19-oic acid and its methyl ester, respectively, by Cephalosporium aphidicola.

  Cephalosporium aphidicola 将 ent-15-Oxokaur-16-en-19-oic 酸及其甲酯分别转化为 ent-11α,16β-dihydroxy-15-oxokauran-19-oic 酸及其甲酯。
• Forced degradation studies, elucidation of degradation pathways and degradation kinetics of Xylopic acid via LC and LC-MS/MS analyses
  作者：Raphael N. Alolga、Isaac Ayensu、Jerry X. Sosu

  DOI：10.1016/j.xphs.2023.01.004

  日期：2023.1

  to various stress conditions (hydrolytic, oxidative, photolytic and thermal) and its degradation products characterized. Seven degradation products were identified and tentatively characterized by LC-MS/MS analysis. The probable degradation pathways for the seven degradation products were then predicted. Using a simple and validated UHPLC-DAD method, the degradation kinetics of XA under the different

  活性药物成分 (API) 的稳定性研究仍然是制药行业的基本质量要求。API的稳定性数据可以指导其加工技术、包装方法和储存条件的选择。在这里，我们试图确定木吡酸 (XA) 在国际协调会议 (ICH) 规定的各种应力条件下的稳定性。XA 是非洲香料Xylopia aethiopica （番荔枝科）的二​​萜贝壳杉烯分离物，具有多种生物活性。XA 经受各种应激条件（水解、氧化、光解和热），并对其降解产物进行了表征。通过 LC-MS/MS 分析鉴定并初步表征了七种降解产物。然后预测了七种降解产物的可能降解途径。使用简单且经过验证的 UHPLC-DAD 方法，综合评估了 XA 在不同胁迫条件下的降解动力学。XA在所有应力条件下的降解均遵循一级反应动力学。人们发现 XA 在强酸性或强碱性溶液以及氧化剂（过氧化氢）中不太稳定。XA 的稳定性还依赖于 pH 值和温度。然而，其稳定性不受紫外光照射的影响。
• Synthesis,<i>in vitro</i>Antimalarial Activity and<i>in silico</i>Studies of Hybrid Kauranoid 1,2,3-Triazoles Derived from Naturally Occurring Diterpenes
  作者：Juliana de O. Santos、Guilherme R. Pereira、Geraldo C. Brandão、Tatiane F. Borgati、Lucas M. Arantes、Renata C. de Paula、Luciana F. Soares、Maria F. A. do Nascimento、Márlia R. C. Ferreira、Alex G. Taranto、Fernando P. Varotti、Alaíde B. de Oliveira

  DOI：10.5935/0103-5053.20150287

  日期：——

  We herein report the synthesis of hybrid kauranoid molecules of type 1,2,3-triazole-1,4-disubstituted aiming to improve the antimalarial activity of kaurenoic and xylopic acids. The Cu-I-catalyzed cycloaddition of azides and kauranoid terminal alkynes was explored as a hybridization strategy. Kauranoid terminal alkynes were prepared from kaurenoic and xylopic acids that were isolated from Wedelia paludosa D. C. (Asteraceae) and Xylopia frutescens Aubl. (Annonaceae). A total of 15 kauranoid derivatives, including nine new triazoles, were obtained and five out of these were more active than the original diterpenes. Interestingly, an increased activity was observed for a kauranoid propargyl ether. Interaction between ent-kaurane diterpene derivatives and Ca2+-ATPase (PfATP6) was investigated. Synthesis of diterpene derivatives emerges as a possible route to be explored in the quest of potentially new inhibitors of PfATP6.