achilleol C | 220359-76-2

• 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: achilleol C
• 英文别名: camelliol C；(1S,5R)-4,6,6-trimethyl-5-[(3E,7E,11E)-3,8,12,16-tetramethylheptadeca-3,7,11,15-tetraenyl]cyclohex-3-en-1-ol
• CAS: 220359-76-2
• 化学式: C₃₀H₅₀O
• 分子量: 426.726
• InChiKey: CIDHBCQEXDUWEB-HJSIMFEZSA-N

物化性质

• 沸点：
  515.9±29.0 °C(Predicted)
• 密度：
  0.892±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  squalene 2,3(S)-oxide 生成 achilleol C
  参考文献：
  名称：

  Arabidopsis Camelliol C Synthase Evolved from Enzymes That Make Pentacycles

  摘要：

  We establish by heterologous expression that the Arabidopsis thaliana oxidosqualene cyclase At1g78955 (CAMS1) makes camelliol C (98%), achilleol A (2%), and beta-amyrin (0.2%). CAMS1 is the first characterized cyclase that generates predominantly a monocyclic triterpene alcohol. Phylogenetic analysis shows that CAMS1 evolved from enzymes that make pentacycles, thus revealing that its pentacyclic beta-amyrin byproduct is an evolutionary relic. Sequence alignments support prior suggestions that decreased steric bulk at a key active-site residue promotes monocycle formation.

  DOI：

  10.1021/ol702399g

文献信息

• Zeolite NaY‐Promoted Monocyclization of Epoxy Polyene Terpenes: A Unique Route for the Direct Synthesis of Incompletely Cyclized Naturally Occurring Terpenols
  作者：Constantinos Tsangarakis、Christos Raptis、Elias Arkoudis、Manolis Stratakis

  DOI：10.1002/adsc.200800180

  日期：2008.7.7

  the brown algae Cystophora monoliformis. The optical rotation of achilleol A derived from the cyclization of (S)-2,3-epoxysqualene matches with that of the natural product, thus the absolute configuration of achilleol A was established as 1S,3R. From the mechanistic point of view, the NaY-promoted cyclization of 9,10-epoxygeranylacetone, selectively deuterium labelled at the C-10 methyl group, is >97%

  通过限制在NaY沸石中，各种环氧多烯萜容易环化，主要形成单环化产物。不管环氧萜烯的侧链如何，单环化途径都非常占优势，而单环产物具有区域选择性地具有外亚甲基双键。在乙酸法呢烯基乙酸酯，环氧法呢烯基丙酮或2,3-环氧角鲨烯的情况下，选择性单环化为合成多种天然产物（例如榄香二醇，法呢香酚B–D，阿奇儿醇A，山茶酚C和四种法呢基丙酮）提供了直接途径。褐藻中提取的代谢产物。由（S的环化引起的Achilleol A的旋光。基）-2,3-环氧角鲨烯与天然产物的匹配，从而achilleol A的绝对构型确定为1小号，3 - [R 。从机理的角度来看，NaY促进的9,10-环氧香叶基丙酮（在氘代C-10甲基上进行选择性氘标记）的环化相对于宝石-二甲基基团的局部立体选择性> 97％。这一结果与协调机制相吻合。最后，我们首次通过标记实验证明，环氧多烯萜烯在酸催化下向2,3,4-三甲基环己酮的仿生转化是高度立体选
• Steric Bulk at Cycloartenol Synthase Position 481 Influences Cyclization and Deprotonation
  作者：Seiichi P. T. Matsuda、Lisa B. Darr、Elizabeth A. Hart、Jennifer B. R. Herrera、Kelly E. McCann、Michelle M. Meyer、Jihai Pang、Hala G. Schepmann

  DOI：10.1021/ol006018w

  日期：2000.7.1

  Cycloartenol synthase converts oxidosqualene to the pentacyclic sterol precursor cycloartenol. An Arabidopsis thaliana cycloartenol synthase Ile481Val mutant was previously shown to produce lanosterol and parkeol in addition to its native product cycloartenol. Experiments are described here to construct Phe, Leu, Ala, and Gly mutants at position 481 and to determine their cyclization product profiles

  环烯醇合酶将氧化角鲨烯转化为五环固醇前体环烯醇。以前显示出拟南芥环戊烯醇合酶Ile481Val突变体除天然产物环戊烯醇外还产生羊毛甾醇和Parkeol。此处描述了在481位构建Phe，Leu，Ala和Gly突变体并确定其环化产物谱的实验。Phe突变体是无活性的，Leu突变体产生了环戊烯醇和Parkeol。Ala和Gly突变体形成了羊毛甾醇，环戊烯醇，Parkeol，阿奇儿醇A和山茶醇C。单环化合物包含大部分Gly突变体产物，表明可通过单个非极性突变将替代环化途径作为主要途径。
• Streptomyces endophyte compositions and methods for improved agronomic traits in plants
  申请人：INDIGO AG, INC.

  公开号：US10750711B2

  公开（公告）日：2020-08-25

  This invention relates to methods and compositions for providing a benefit to a plant by associating the plant with a beneficial endophyte of the genus Streptomyces, including benefits to a plant derived from a seed or other plant element treated with said endophyte. For example, this invention provides purified endophytes, synthetic combinations comprising endophytes, and methods of making and using the same. In particular, this invention relates to compositions and methods of improving soybean and maize plants.

  本发明涉及通过将植物与有益的链霉菌属内生菌结合而为植物提供益处的方法和组合物，包括为经所述内生菌处理的种子或其他植物元素衍生的植物提供益处。例如，本发明提供了纯化的内生菌、包含内生菌的合成组合物以及制造和使用方法。特别是，本发明涉及改良大豆和玉米植物的组合物和方法。
• Camelliols A−C, Three Novel Incompletely Cyclized Triterpene Alcohols from Sasanqua Oil (<i>Camellia sasanqua</i>)
  作者：Toshihiro Akihisa、Koichi Arai、Yumiko Kimura、Kazuo Koike、Wilhelmus C. M. C. Kokke、Tsuyoshi Shibata、Tamotsu Nikaido

  DOI：10.1021/np980336a

  日期：1999.2.1

  Three novel triterpene alcohols, camelliols A (1), B (3), and C (5), possessing a mono-, bi-, and tricyclic ring system, respectively, have been isolated, along with achilleol A, a known monocyclic triterpene alcohol, from the nonsaponifiable lipids of sasanqua oil (Camellia sasanqua). The structures of these new alcohols were determined on the basis of spectroscopic methods.
• <i>Arabidopsis </i>Camelliol C Synthase Evolved from Enzymes That Make Pentacycles
  作者：Mariya D. Kolesnikova、William K. Wilson、David A. Lynch、Allie C. Obermeyer、Seiichi P. T. Matsuda

  DOI：10.1021/ol702399g

  日期：2007.12.1

  We establish by heterologous expression that the Arabidopsis thaliana oxidosqualene cyclase At1g78955 (CAMS1) makes camelliol C (98%), achilleol A (2%), and beta-amyrin (0.2%). CAMS1 is the first characterized cyclase that generates predominantly a monocyclic triterpene alcohol. Phylogenetic analysis shows that CAMS1 evolved from enzymes that make pentacycles, thus revealing that its pentacyclic beta-amyrin byproduct is an evolutionary relic. Sequence alignments support prior suggestions that decreased steric bulk at a key active-site residue promotes monocycle formation.