cis,cis-Nepetalactol | 185399-79-5

• 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: cis,cis-Nepetalactol
• 英文别名: (4αR,7S,7αS)nepetalactol；(4aR,7S,7aS)-nepetalactol；nepetalactol；(4aR,7S,7aS)-4,7-dimethyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-ol
• CAS: 185399-79-5
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: OJGPEAXUHQRLNC-DJOKAMFZSA-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：

  乙酸酐 、 cis,cis-Nepetalactol 在 二异丁基氢化铝 、 吡啶 、 4-二甲氨基吡啶 作用下， 以 正己烷 为溶剂， 反应 0.5h， 生成 [(1S,4aR,7S,7aS)-4,7-dimethyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-yl] acetate 、 [(1R,4aR,7S,7aS)-4,7-dimethyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-yl] acetate
  参考文献：
  名称：

  Simplified Isolation Procedure and Interconversion of the Diastereomers of Nepetalactone and Nepetalactol

  摘要：

  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.

  DOI：

  10.1021/np049647d
• 作为产物：
  描述：

  (3S,4R)-3-methyl-4-(3-oxobutyl)cyclopentan-1-one 在 palladium on activated charcoal potassium hydrogensulfate 、 氢气 、 二异丁基氢化铝 、 对甲苯磺酸 、 臭氧 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 环己烷 、 甲苯 为溶剂， 反应 12.0h， 生成 cis,cis-Nepetalactol
  参考文献：
  名称：

  The Potential of Semiochemicals for Control ofPhorodon humuli(Homoptera: Aphididae)

  摘要：

  Field experiments employing yellow water-traps with vials releasing methyl salicylate, butyl isothiocyanate, 4-pentenyl isothiocyanate and diethyltoluamide were conducted during the spring migration of Phorodon humuli (Schrank), with the aim of identifying substances which might be used in the field to deter landing on hop plants. Methyl salicylate and the two isothiocyanates reduced trap catches of P. humuli. During the spring of 1994 a slow-release formulation of methyl salicylate and a beta-acid-rich hop resin sprayed on to hop plants did not reduce aphid infestations significantly. In autumn cis,cis-nepetalactol the main component of P. humuli's sex pheromone, prepared by various synthetic routes, increased trap catches of males and gynoparae equally. Catches of males in pheromone traps situated in a hop garden decreased with increasing trap height. Catches of males in traps charged with increasing doses of the cis,cis-nepetalactol peaked at 1 mg and then plateaued, whereas catches of gynoparae peaked similarly at 1 mg and then decreased. The effects of kairomones from an extract of the primary host, sex pheromone and a visual cue from yellow compared with clear water-traps were additive. The prospects for developing a semiochemicals-based control strategy against P. humuli, using some or all of the above elements, are discussed.

  DOI：

  10.1002/(sici)1096-9063(199612)48:4<293::aid-ps479>3.0.co;2-5

文献信息

• Nepetalactol oxidoreductase in trichomes of the catmint Nepeta racemosa
  作者：David L. Hallahan、Jevon M. West、Diane W.M. Smiley、John A. Pickett

  DOI：10.1016/s0031-9422(98)00006-5

  日期：1998.6

  Abstract Isomers of (7 S )-nepetalactone are the principal constituents of the essential oil accumulated by plants of the genus Nepeta (catmints), with the cis , cis -isomer predominating in the catmint N. racemosa . An enzyme which catalyses the NAD + -dependent oxidation of cis , cis -nepetalactol to cis , cis -nepetalactone has been identified in cell-free extracts of N. racemosa leaves. This enzyme

  摘要 (7 S )-荆芥内酯的异构体是荆芥属植物（荆芥）积累的精油的主要成分，在荆芥总状荆芥中以顺式、顺式异构体为主。已在总状花椰菜叶的无细胞提取物中鉴定出一种酶，该酶催化 NAD + 依赖性氧化顺式，顺式 - 荆芥内酯为顺式，顺式 - 荆芥内酯。这种酶已被部分纯化，并已被证明位于该物种叶子表面的毛状体中。因为腺毛已被证明是荆芥内酯在总状花序草和卡塔利亚山楂中积累的场所，毛状体中存在这种活性表明荆芥内酯可能是荆芥内酯生物合成的中间体。
• Uncoupled activation and cyclization in catmint reductive terpenoid biosynthesis
  作者：Benjamin R. Lichman、Mohamed O. Kamileen、Gabriel R. Titchiner、Gerhard Saalbach、Clare E. M. Stevenson、David M. Lawson、Sarah E. O’Connor

  DOI：10.1038/s41589-018-0185-2

  日期：2019.1

  NEPS1 provides nepetalactones, metabolites that are well known for both insect-repellent activity and euphoric effects in cats. Structural characterization of the NEPS3 cyclase reveals that it binds to NAD+ yet does not utilize it chemically for a non-oxidoreductive formal [4 + 2] cyclization. These discoveries will complement metabolic reconstructions of iridoid and monoterpene indole alkaloid biosynthesis

  萜烯合酶通常通过在单个酶活性位点中线性起始材料的协同活化和环化形成复杂的分子支架。在这里，我们显示环烯醚萜合酶，一种非典型的还原性萜烯合酶，催化其底物 8-氧代香叶醛活化为活性烯醇中间体，但不催化随后的环化为荆芥内醇。这一发现使我们从猫薄荷 ( Nepeta mussinii ) 中鉴定出一类与荆芥内醇相关的短链脱氢酶 (NEPS)) 捕获这种反应性中间体并催化立体选择性环化为不同的荆芥内酯立体异构体。NEPS1 对荆芥内酯的后续氧化提供荆芥内酯，这是众所周知的在猫中具有驱虫活性和欣快作用的代谢物。NEPS3 环化酶的结构表征表明它与 NAD +结合，但不会化学利用它进行非氧化还原形式的 [4 + 2] 环化。这些发现将补充环烯醚萜和单萜吲哚生物碱生物合成的代谢重建。
• Biocatalytic Strategies towards [4+2] Cycloadditions
  作者：Benjamin R. Lichman、Sarah E. O'Connor、Hajo Kries

  DOI：10.1002/chem.201805412

  日期：2019.5.17

  problem in chemical synthesis. In a few cases, detailed pictures of the inner workings of these catalysts have emerged, but intense efforts to gain deeper understanding are underway by means of crystallography and computational modelling. This Minireview aims to shed light on the catalytic strategies that this highly diverse family of enzymes employs to accelerate and direct the course of [4+2] cycloadditions

  近年来，人们一直在追捧的 [4+2] 环化酶在众多生物合成途径中不断涌现，为环加成催化这一化学合成中的一个重要问题的生物催化解决方案带来了希望。在少数情况下，已经出现了这些催化剂内部运作的详细图片，但正在通过晶体学和计算建模进行深入了解的努力。这篇 Minireview 旨在阐明这一高度多样化的酶家族所采用的催化策略，以参考小分子催化剂和设计酶来加速和指导 [4+2] 环加成的过程。这些催化策略包括氧化或还原触发以及酶域的类似盖子的运动。
• Nepetalactol oxidoreductases, nepetalactol synthases, and microbes capable of producing nepetalactone
  申请人：Zymergen Inc.

  公开号：US10696991B2

  公开（公告）日：2020-06-30

  The present disclosure provides isolated nepetalactone oxidoreductase polypeptides (NORs), nepetalactol synthases (NEPSs), and related polynucleotides, engineered host cells, and cultures, as well as methods for producing NORs and NEPSs, and for using them to produce nepetalactol, nepetalactone, and dihydronepetalactone. The present disclosure also provides methods for engineering cells (e.g., microbial cells) to produce nepetalactone from a fermentation substrate such as glucose, as well as engineered cells having this capability and related cultures and methods for producing nepetalactone.

  本公开提供了分离的新内酯氧化还原酶多肽（NORs）、新内酯合成酶（NEPSs）和相关多核苷酸、工程化宿主细胞和培养物，以及生产NORs和NEPSs的方法和使用它们生产新内酯、新内酯和二氢新内酯的方法。本公开内容还提供了工程细胞（如微生物细胞）从发酵底物（如葡萄糖）生产新内酯的方法，以及具有这种能力的工程细胞和相关培养物和生产新内酯的方法。
• NEPETALACTOL OXIDOREDUCTASES, NEPETALACTOL SYNTHASES, AND MICROBES CAPABLE OF PRODUCING NEPETALACTONE
  申请人：Zymergen Inc.

  公开号：US20200362376A1

  公开（公告）日：2020-11-19

  The present disclosure provides isolated nepetalactone oxidoreductase polypeptides (NORs), nepetalactol synthases (NEPSs), and related polynucleotides, engineered host cells, and cultures, as well as methods for producing NORs and NEPSs, and for using them to produce nepetalactol, nepetalactone, and dihydronepetalactone. The present disclosure also provides methods for engineering cells (e.g., microbial cells) to produce nepetalactone from a fermentation substrate such as glucose, as well as engineered cells having this capability and related cultures and methods for producing nepetalactone.