cycloeucalenone | 1255-12-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: cycloeucalenone
• 英文别名: (1S,3R,7S,8S,11S,12S,15R,16R)-7,12,16-trimethyl-15-[(2R)-6-methyl-5-methylideneheptan-2-yl]pentacyclo[9.7.0.01,3.03,8.012,16]octadecan-6-one
• CAS: 1255-12-5
• 化学式: C₃₀H₄₈O
• 分子量: 424.711
• InChiKey: NFRXSIOHGADFRG-MEMZBLDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  cycloeucalenone 在 monosodium salt of ethylene glycol 、 乙二醇 、 肼 作用下， 生成 24-methylene-9β,19-cyclo-31-nor-lanostane
  参考文献：
  名称：

  Cox et al., Journal of the Chemical Society, 1959, p. 514,517

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 chromium(VI) oxide 作用下， 生成 cycloeucalenone
  参考文献：
  名称：

  Cox et al., Journal of the Chemical Society, 1956, p. 1384,1391

  摘要：

  DOI：

文献信息

• Buxus alkaloids. Part VII. The isolation and the constitutions of ten new alkaloids from the weak-base fractions of two species, B. microphylla Sieb. et Zucc. var. suffruticosa Makino and B. microphylla Sieb. et Zucc. var. suffruticosa Makino forma major Makino
  作者：T. Nakano、S. Terao、Y. Saeki

  DOI：10.1039/j39660001412

  日期：——

  Investigation of the weak-base fractions of two species, B. microphylla Sieb. et Zucc. var. suffruticosa Makino and B. microphylla Sieb. et Zucc. var. suffruticosa Makino forma major Makino, has led to the isolation of ten new alkaloids. In addition, another new alkaloid was isolated from the strong-base fraction of the latter species. These alkaloids are structurally closely related, and their interconversion

  调查的两个物种，B。microphylla Sieb的弱碱部分。et Zucc。变种 suffruticosa Makino和B. microphylla Sieb。et Zucc。变种 suffruticosa Makino forma主要的Makino导致分离出十种新生物碱。此外，从后者物种的强碱部分中分离出了另一种新的生物碱。这些生物碱在结构上密切相关，并且已经确定了它们与其他已知生物碱的相互转化。
• 4-Epicycloeucalenone and 4-Epicyclomusalenone: Two 3-Oxo-28-norcycloartanes from the Fruit Peel of Musa sapientum L.
  作者：Toshihiro AKIHISA、Yumiko KIMURA、Wilhelmus C. M. C. KOKKE、Sei-ichi TAKASE、Ken YASUKAWA、Aiko JIN-NAI、Toshitake TAMURA

  DOI：10.1248/cpb.45.744

  日期：——

  Two 3-oxo-28-norcycloartane-type triterpenes, 4-epicycloeucalenone and 4-epicyclomusalenone, and two known 3-oxo-29-norcycloartanes, cycloeucalenone and cyclomusalenone, were isolated from the n-hexane extract of the fruit peel of Musa sapientum L. (banana). The structures of the 28-norcycloartanes were determined by spectroscopic and chemical methods.

  从香蕉（Musa sapientum L.）果皮正己烷提取物中分离出两种3-氧代-28-去甲环木烷型三萜类化合物（4-表环木烯酮和4-表环木烯酮）以及两种已知的3-氧代-29-去甲环木烷（环木烯酮和环木烯酮）。通过光谱和化学方法确定了28-去甲环木烷的结构。
• Homology Modeling and Site-Directed Mutagenesis Reveal Catalytic Key Amino Acids of 3<i>β</i>-Hydroxysteroid-Dehydrogenase/C4-Decarboxylase from Arabidopsis  
  作者：Alain Rahier、Marc Bergdoll、Geneviève Génot、Florence Bouvier、Bilal Camara

  DOI：10.1104/pp.108.132282

  日期：2009.4.1

  3beta-hydroxysteroid-dehydrogenase/C4-decarboxylase (3betaHSD/D). We recently identified Arabidopsis (Arabidopsis thaliana) 3betaHSD/D as a bifunctional short-chain dehydrogenase/reductase protein. We made use of three-dimensional homology modeling to identify key amino acids involved in 4alpha-carboxy-sterol and NAD binding and catalysis. Key amino acids were subjected to site-directed mutagenesis, and the

  只有通过膜结合多酶复合物（包括 3beta-羟基类固醇脱氢酶/C4-脱羧酶 (3betaHSD/D)）去除 C4 处的两个甲基后，甾醇才会发挥作用。我们最近发现拟南芥（拟南芥）3betaHSD/D 作为双功能短链脱氢酶/还原酶蛋白。我们利用三维同源性建模来确定参与 4alpha-羧基甾醇和 NAD 结合和催化的关键氨基酸。对关键氨基酸进行定点诱变，并在 3betaHSD/D 缺陷的 erg26 酵母菌株中在体内和体外表达和测定突变的酶。我们表明 tyrosine-159 和 lysine-163 位于模型中底物的 3beta-羟基附近，对于 3betaHSD/D 活性至关重要，与它们参与反应的初始脱氢步骤一致。预计必需的精氨酸 326 残基会与底物的 4α-羧基形成盐桥，表明其参与底物结合和脱羧步骤。必需的天冬氨酸-39 残基与 NAD+ 的腺苷-核糖环的羟基紧密接触，与 3betaHSD/D
• Molecular and Enzymatic Characterizations of Novel Bifunctional 3β-Hydroxysteroid Dehydrogenases/C-4 Decarboxylases from Arabidopsis thaliana
  作者：Alain Rahier、Sylvain Darnet、Florence Bouvier、Bilal Camara、Martin Bard

  DOI：10.1074/jbc.m604431200

  日期：2006.9

  At3betaHSD/D1 endoplasmic reticulum-retrieval sequence restored growth and ergosterol synthesis in erg26. An in vitro enzymatic assay revealed high 3betaHSD/D activity for both isoenzymes in the corresponding microsomal extracts. The two At3betaHSD/D isoenzymes showed similar substrate specificities that required free 3beta-hydroxyl and C-4-carboxyl groups but were quite tolerant in terms of variations of

  我们从拟南芥中分离了两个编码参与固醇合成的双功能3β-羟基类固醇脱氢酶/ C-4脱羧酶（3betaHSD / D）的cDNA，称为At3betaHSD / D1和At3betaHSD / D2。缺少3betaHSD / D活性的酵母麦角固醇营养缺陷型erg26突变体的转化是利用At3betaHSD / D1亚型或含有C末端At3betaHSD / D1内质网检索序列的At3betaHSD / D2亚型恢复了erg26中的生长和麦角甾醇合成。体外酶促测定显示相应微粒体提取物中的两种同工酶均具有较高的3betaHSD / D活性。两种At3betaHSD / D同工酶显示相似的底物特异性，需要游离的3β-羟基和C-4-羧基，但在甾醇核和侧链结构的变化方面具有相当的耐受性。用4alpha-羧基胆甾-7-en-3beta-ol及其3alpha氘代类似物获得的数据表明，3alpha-氢-碳键裂解不是
• Cycloartane triterpenes from the fruit peel of Musa sapientum
  作者：Toshihiro Akihisa、Yumiko Kimura、Toshitake Tamura

  DOI：10.1016/s0031-9422(98)80081-2

  日期：1998.3