17-Hydroxy-ent-isokaur-15-en-saeuremethylester | 35030-39-8

• 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: 17-Hydroxy-ent-isokaur-15-en-saeuremethylester
• 英文别名: methyl ent-17-hydroxykauran-19-oate；methyl ent-17-hydroxy-15-en-19-oate；methyl ent-17-hydroxy-kaur-15-en-19-oate；methyl (1S,4S,5R,9S,10S,13R)-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.01,10.04,9]hexadec-14-ene-5-carboxylate
• CAS: 35030-39-8
• 化学式: C₂₁H₃₂O₃
• 分子量: 332.483
• InChiKey: IURJXDRUVNGNGB-CQAWWZBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  17-Hydroxy-ent-isokaur-15-en-saeuremethylester 在 manganese(IV) oxide 作用下， 以 乙醚 为溶剂， 反应 72.0h， 以15 mg的产率得到17-oxo-ent-kaur-15(16)-en-19-oic acid methyl ester
  参考文献：
  名称：

  来自 Espeletiopsis 物种的三环倍半萜和其他二萜

  摘要：

  摘要 通过对五种 Espeletiopsis 和两种 Coespeletia 物种的研究，除了许多已知化合物外，还提供了两种新的 kaurene 衍生物 19-acetoxy-ent-kaurene 和 17-oxo-ent-kaur-15-en-19-oic acid，以及作为两种新的三环倍半萜烯，一种是之前报道的copaborneol的氧化产物，另一种是silphiperfol-6-ene的5-氧代衍生物。通过核磁共振研究和化学转化阐明了结构。简要讨论了化学分类情况。

  DOI：

  10.1016/s0031-9422(00)91035-5
• 作为产物：
  描述：

  贝壳杉烯酸 在 偶氮二异丁腈 、 间氯过氧苯甲酸 作用下， 反应 20.0h， 生成 17-Hydroxy-ent-isokaur-15-en-saeuremethylester
  参考文献：
  名称：

  Occurrence and origin of ent-17-hydroxykaur-15-ene and ent-17-hydroxykaur-15-en-19-oic acid in shoots of Zea mays

  摘要：

  Previously unidentified metabolites of ent-kaur-16-ene and ent-kaur-16-en-19-oic acid in shoots of maize are identified, respectively, as ent-17-hydroxykaur-15-ene and ent-17-hydroxykaur-15-en-19-oic acid by GC-MS comparison with authentic samples. The production of the two latter compounds from the first two substances is analogous to the metabolism of gibberellin A(5) to gibberellin A(3) and provides two further examples, in plants, of hydroxylation at a double bond with rearrangement of the double bond.

  DOI：

  10.1016/s0031-9422(00)90832-x

文献信息

• Neue diterpene aus der subtribus espeletiinae
  作者：Ferdinand Bohlmann、Hubert Suding、José Cuatrecasas、Robert M. King、Harold Robinson

  DOI：10.1016/s0031-9422(00)81971-8

  日期：1980.1

  The investigation of several species from the newly created subtribe Espeletiinae afforded in addition to known compounds seven new diterpenes and two norditerpenes. The structures were elucidated by intensive 1H-NMR studies. The chemotaxonomic situation is discussed briefly.

  对来自新创建的亚部落 Espeletiinae 的几个物种的调查提供了除已知化合物之外的七个新二萜和两个降二萜。通过密集的 1 H-NMR 研究阐明了结构。简要讨论了化学分类情况。
• Ent-kauranes and other constituents of three Helianthus species
  作者：W HERZ、P KULANTHAIVEL、K WATANABE

  DOI：10.1016/0031-9422(83)80036-3

  日期：——

  of Helianthus debilis subsp. cucumerifolius, H. occidentalis and H. simulans afforded a variety of known and some unknown ent-kauranoic acids. H. occidentalis gave, in addition, ciliaric acid and a new biogenetically related atisane derivative occidentalic acid. H. simulans gave the heliangolide leptocarpin and the flavone hymenoxin in addition to ent-kauranes. Several of the diterpenoids from these

  Helianthus debilis subsp 的抽象空中部分。cucumerifolius、H. occidentalis 和 H. simulans 提供了多种已知和一些未知的 ent-kauranoic 酸。此外，H. occidentalis 还提供了纤毛酸和一种新的生物遗传学相关的 atisane 衍生物 occidentalic acid。除了 ent-kauranes 之外，H. simulans 还提供 heliangolide leptocarpin 和黄酮 hymenoxin。来自这些物种的几种二萜类化合物抑制了向日葵蛾的幼虫生长。
• Synthesis, cytotoxicity and antiplasmodial activity of novel ent -kaurane derivatives
  作者：Ronan Batista、Pablo A. García、María Angeles Castro、José M. Miguel del Corral、Nivaldo L. Speziali、Fernando de P. Varotti、Renata C. de Paula、Luis F. García-Fernández、Andrés Francesch、Arturo San Feliciano、Alaíde B. de Oliveira

  DOI：10.1016/j.ejmech.2012.12.010

  日期：2013.4

  This paper reports on the syntheses and spectrometric characterisation of eleven novel ent-kaurane diterpenoids, including a complete set of H-1, C-13 NMR and crystallographic data for two novel ent-kaurane diepoxides. Moreover, the antineoplastic cytotoxicity for kaurenoic acid and the majority of ent-kaurane derivatives were assessed in vitro against a panel of fourteen cancer cell lines, of which allylic alcohols were shown to be the most active compounds. The good in vitro antimalarial activity and the higher selectivity index values observed for some ent-kaurane epoxides against the chloroquine-resistant W2 clone of Plasmodium falciparum indicate that this class of natural products may provide new hits for the development of antimalarial drugs. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Occurrence and origin of ent-17-hydroxykaur-15-ene and ent-17-hydroxykaur-15-en-19-oic acid in shoots of Zea mays
  作者：Jake MacMillan、Paul Gaskin

  DOI：10.1016/s0031-9422(00)90832-x

  日期：1993.12

  Previously unidentified metabolites of ent-kaur-16-ene and ent-kaur-16-en-19-oic acid in shoots of maize are identified, respectively, as ent-17-hydroxykaur-15-ene and ent-17-hydroxykaur-15-en-19-oic acid by GC-MS comparison with authentic samples. The production of the two latter compounds from the first two substances is analogous to the metabolism of gibberellin A(5) to gibberellin A(3) and provides two further examples, in plants, of hydroxylation at a double bond with rearrangement of the double bond.
• Tricyclic sesquiterpenes and further diterpenes from Espeletiopsis species
  作者：F. Bohlmann、H. Suding、J. Cuatrecasas、H. Robinson、R.M. King

  DOI：10.1016/s0031-9422(00)91035-5

  日期：1980.1

  Abstract The investigation of five Espeletiopsis and two Coespeletia species afforded, in addition to numerous known compounds, two new kaurene derivatives 19-acetoxy-ent-kaurene and 17-oxo-ent-kaur- 15-en-19-oic acid, as well as two new tricyclic sesquiterpenes, one being the previously reported oxidation product of copaborneol and the second one the 5-oxo derivative of silphiperfol-6-ene. The structures

  摘要 通过对五种 Espeletiopsis 和两种 Coespeletia 物种的研究，除了许多已知化合物外，还提供了两种新的 kaurene 衍生物 19-acetoxy-ent-kaurene 和 17-oxo-ent-kaur-15-en-19-oic acid，以及作为两种新的三环倍半萜烯，一种是之前报道的copaborneol的氧化产物，另一种是silphiperfol-6-ene的5-氧代衍生物。通过核磁共振研究和化学转化阐明了结构。简要讨论了化学分类情况。