iridodial | 69252-84-2

• 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: iridodial
• 英文别名: (1R,4aS,7S,7aR)-4,7-dimethyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-ol
• CAS: 69252-84-2
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: OJGPEAXUHQRLNC-JZKKDOLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  iridodial 、 3,5-二硝基苯甲酰氯 以32%的产率得到
  参考文献：
  名称：

  DAWSON, GLENN W.;JANES, NORMAN F.;MUDD, ALAN;PICKETT, JOHN A.;SLAWIN, ALE+, PURE AND APPL. CHEM., 61,(1989) N, C. 555-558

  摘要：

  DOI：
• 作为产物：
  描述：

  假荆芥内酯 在 二异丁基氢化铝 作用下， 生成 iridodial
  参考文献：
  名称：

  Method for soybean aphid population suppression and monitoring using aphid-and host-plant-associated semiochemical compositions

  摘要：

  大豆挥发性化合物、大豆蚜虫诱导的挥发性化合物和大豆蚜虫性信息素是本发明中用于抑制大豆蚜虫种群的信号化学物质。甲基水杨酸酯是本发明中有用的大豆蚜虫诱导的挥发性化合物的一种实施例。苯甲醛是本发明中有用的大豆寄主植物挥发性化合物的一种实施例。此外，尼泊酮醇和尼泊酮也可用作性信息素。这些化合物可以在优选实施例中混合使用。

  公开号：

  US20050249769A1

文献信息

• Elucidation of iridodial formation mechanism - partial purification and characterization of the novel monoterpene cyclase from cell suspension cultures
  作者：Shinichi Uesato、Hiromitsu Ikeda、Tetsuro Fujita、Hiroyuki Inouye、Meinhart H. Zenk

  DOI：10.1016/s0040-4039(00)96530-4

  日期：1987.1

  From the incubation system of 10-hydroxygeraniol and crude enzyme extracts from cell suspension cultures, 10-oxogeraniol, 10-hydroxygeranial and 10-oxogeranial were isolated. A precursory role in the biosynthesis of iridodial has been demonstrated for these three compounds. This fact unequivocally substantiates our previous claim for the biosynthesis of iridodial. In addition, a novel monoterpene cyclase

  从10-羟基香叶醇和细胞悬浮培养物的粗酶提取物的培养系统中，分离出10-氧香叶醇，10-羟基香叶醛和10-氧香叶醛。对于这三种化合物，已证明在铱的生物合成中具有先驱作用。这一事实明确地证实了我们先前对虹膜二代生物合成的主张。另外，部分纯化并表征了催化虹彩形成的新型单萜环化酶。
• The seco-iridoid pathway from Catharanthus roseus
  作者：Karel Miettinen、Lemeng Dong、Nicolas Navrot、Thomas Schneider、Vincent Burlat、Jacob Pollier、Lotte Woittiez、Sander van der Krol、Raphaël Lugan、Tina Ilc、Robert Verpoorte、Kirsi-Marja Oksman-Caldentey、Enrico Martinoia、Harro Bouwmeester、Alain Goossens、Johan Memelink、Danièle Werck-Reichhart

  DOI：10.1038/ncomms4606

  日期：——

  The (seco)iridoids and their derivatives, the monoterpenoid indole alkaloids (MIAs), form two large families of plant-derived bioactive compounds with a wide spectrum of high-value pharmacological and insect-repellent activities. Vinblastine and vincristine, MIAs used as anticancer drugs, are produced by Catharanthus roseus in extremely low levels, leading to high market prices and poor availability. Their biotechnological production is hampered by the fragmentary knowledge of their biosynthesis. Here we report the discovery of the last four missing steps of the (seco)iridoid biosynthesis pathway. Expression of the eight genes encoding this pathway, together with two genes boosting precursor formation and two downstream alkaloid biosynthesis genes, in an alternative plant host, allows the heterologous production of the complex MIA strictosidine. This confirms the functionality of all enzymes of the pathway and highlights their utility for synthetic biology programmes towards a sustainable biotechnological production of valuable (seco)iridoids and alkaloids with pharmaceutical and agricultural applications. The (seco)iridoids and their monoterpenoid indole alkaloid (MIA) derivatives are plant-derived compounds with pharmaceutical applications. Here, the authors identify the last four missing steps of the (seco)iridoid pathway, which they reconstitute in an alternative plant host to produce the complex MIA, strictosidine.

  （seco）iridoids及其衍生物、单萜类吲哚生物碱（MIAs）构成了两大类植物来源的生物活性化合物，具有广泛的高价值药理和驱虫活性。长春碱和长春新碱是MIAs中用作抗癌药物的两种物质，由长春花（Catharanthus roseus）产生，但产量极低，导致市场价格高且供应不足。由于对其生物合成过程的了解不全面，生物技术生产受到阻碍。本文报道了（seco）iridoid生物合成途径最后四个缺失步骤的发现。在替代植物宿主中表达编码该途径的八个基因，以及两个促进前体形成的基因和两个下游生物碱生物合成基因，可以异源生产复杂的MIA strictosidine。这证实了该途径中所有酶的功能，并突出了它们在合成生物学计划中的实用性，有助于以可持续的生物技术生产具有药用和农业应用价值的（seco）iridoids和生物碱。（seco）iridoids及其单萜类吲哚生物碱（MIA）衍生物是具有药用价值的植物来源化合物。作者在此确定了（seco）iridoid途径的最后四个缺失步骤，并在替代植物宿主中重建了这些步骤，以生产复杂的MIA strictosidine。
• Synthesis of iridodial by cell free extracts from cell suspension cultures
  作者：Shinichi Uesato、Yasuko Ogawa、Hiroyuki Inouye、Kayoko Saiki、Meinhart H Zenk

  DOI：10.1016/s0040-4039(00)84672-9

  日期：——
• A Divergent Approach to the Diastereoselective Synthesis of Several Ant-Associated Iridoids
  作者：Joel S. Beckett、James D. Beckett、John E. Hofferberth

  DOI：10.1021/ol100077z

  日期：2010.4.2

  The ant-associated iridoids nepetalactol, actinidine, dolichodial, isoiridomyrmecin, and dihydronepetalactone were prepared from citronellal using a divergent approach. Key features include a three-step synthesis of the Individual antipodes of actinidine by a novel tandem cycloaddition/pyridine formation and a facile diastereoselective synthesis of both enantiomers of dolichodial.
• Simplified Isolation Procedure and Interconversion of the Diastereomers of Nepetalactone and Nepetalactol
  作者：Ilme Liblikas、Ellen M. Santangelo、Johan Sandell、Peter Baeckström、Mats Svensson、Ulla Jacobsson、C. Rikard Unelius

  DOI：10.1021/np049647d

  日期：2005.6.1

  Three nepetalactones were isolated from Nepeta racemosa (mussinii) by traditional methods. An improved method was developed to isolate nepetalactones from N. faassenii. An epimerization procedure was used to prepare the fourth 7S-nepetalactone diastereomer. The cis-fused nepetalactols were prepared by reduction of the corresponding nepetalactones, while the trans-fused nepetalactols were unstable and found to undergo ring-opening reactions yielding iridodials. The characterizations and structural assignments by means of NMR agree with quantum chemical density functional calculations.