6-epicerevisterol | 60497-23-6

• 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: 6-epicerevisterol
• 英文别名: 22E,24R-3beta, 5alpha,6alpha-trihydroxyergosta-7, 22-diene；(3S,5R,6S,9S,10R,13R,14R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-1,2,3,4,6,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-3,5,6-triol
• CAS: 60497-23-6
• 化学式: C₂₈H₄₆O₃
• 分子量: 430.671
• InChiKey: ARXHRTZAVQOQEU-QYYFJRRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-epicerevisterol 在 manganese(IV) oxide 作用下， 以 氯仿 为溶剂， 以1.8 mg的产率得到3,5-二羟基麦角甾醇-7,22-二烯-6-酮
  参考文献：
  名称：

  The constituents of Gymnopilus spectabilis.

  摘要：

  从迷幻蘑菇Gymnopilus spectabilis (FR.) A. H. SMITH中分离并鉴定了Cerevisterol (1)和一种新的炔烃化合物4, 6-decadiyne-1, 3, 8-triol (2)，同时还分离了麦角甾醇、麦角甾醇过氧化物和胆碱。尽管在我们对这种蘑菇的采集样本中未检测到迷幻成分如裸盖菇素及相关化合物，但在其他一些日本蘑菇中发现了部分裸盖菇素。

  DOI：

  10.1248/cpb.34.3465
• 作为产物：
  描述：

  麦角固醇 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以27%的产率得到6-epicerevisterol
  参考文献：
  名称：

  δ7-5-desaturase抑制剂的合成和生物评价，delta 7-5-desaturase抑制剂是真菌固醇麦角固醇生物合成后期的一种酶。

  摘要：

  麦角固醇是真菌的主要固醇，被认为具有许多细胞功能，包括体膜作用和调节作用。对甾醇营养缺陷型的研究表明，即使存在可以满足整体膜需求的甾醇，也绝对需要少量的麦角固醇来生长。麦角固醇的调节作用似乎需要δ5-双键。因此，开发引入这种双键的酶抑制剂δ7-甾醇5-去饱和酶（5-去饱和酶）可能会导致有效的抗真菌剂。其中首次报道了真菌5-去饱和酶抑制剂的合成以及体外tri功效放射测定法的发展。抑制剂具有一般结构7 具有在C-5附近的α-面杂原子取代基的22（E）-麦角甾烷-3β-ol。他们表现出的IC50值为47-149 microM。

  DOI：

  10.1021/jm9605851

文献信息

• Sirosterol and dehydroazasirosterol, unusual steroidal adducts from a <i>Sirococcus</i> species
  作者：William A. Ayer、Yu-Ting Ma

  DOI：10.1139/v92-238

  日期：1992.7.1

  Two unusual compounds, which are made up of a sterol portion fused at C-5 and C-6 to an atrovenetin-like part, have been isolated from a fungus that causes Sirococcus shoot blight of spruce. The structures of these compounds, sirosterol (4) and dehydroazasirosterol (13), were determined by spectroscopic methods and comparison with appropriate model compounds. Sirosterol is an adduct of ergosterol and atrovenetin (5) and dehydroazasirosterol is an adduct of 9(11)-dehydroergosterol and an azaatrovenetin. Both compounds give a monomethyl ether when treated with diazomethane and both have been transformed to the corresponding 3-ketosteroids. The preparation of the triol 6 resulting from the selective hydroxylation of the 5,6-double bond in ergosterol is described. A possible biogenesis of sirosterol from ergosterol endoperoxide and a desoxyatrovenetin is discussed.

  两种不寻常的化合物，由甾醇部分与类atrovenetin部分在C-5和C-6处融合而成，已从引起云杉萌发枯病的真菌中分离出来。这些化合物的结构，sirosterol（4）和dehydroazasirosterol（13），通过光谱方法和与适当的模型化合物比较确定。Sirosterol是麦角固醇和atrovenetin（5）的加合物，而dehydroazasirosterol是9（11）-去氢麦角固醇和azaatrovenetin的加合物。两种化合物在处理二氮甲烷时均生成单甲醚，并且两者均已转化为相应的3-酮类固醇。描述了通过对麦角固醇中5,6-双键进行选择性羟化而得到的三醇6的制备。讨论了sirosterol可能从麦角固醇内过氧化物和去氧atrovenetin的生物合成途径。
• Criegee; Marchand; Wannowius, Justus Liebigs Annalen der Chemie, 1942, vol. 550, p. 125
  作者：Criegee、Marchand、Wannowius

  DOI：——

  日期：——
• EHL Film Thickness Limitation Theory Under a Limiting Shear Stress
  作者：Yongbin Zhang、Shizhu Wen

  DOI：10.1080/10402000208982584

  日期：2002.1

  It is numerically shown that the elastohydrodynamic lubrication (EHL) film thickness has a limit under an assumed limiting shear stress of the contact-lubricant interface in isothermal Pure rolling line contacts. The prediction of the central film thickness limit is made, and well matches experiments. The present theory shows that, in elastohydrodynamic line contacts, the central film thickness is of molecular scale and part of the contact area is in non-continuum film lubrication when the equivalent cylinder curvature radius is less than the critical one. This critical radius depends on the load and the contact-lubricant interfacial limiting shear stress at low pressures.
• Seasonal variations in the community structure of aquatic organisms in a paddy field under a long-term fertilizer trial
  作者：Masatsugu Yamazaki、Yukihiro Hamada、Takeo Ibuka、Takashi Momii、Makoto Kimura

  DOI：10.1080/00380768.2001.10408422

  日期：2001.9

  To estimate the effect of fertilizers on aquatic organisms ranging in size from 30 mum to 2 cm in a Japanese paddy field under a long-term fertilizer trial (the plots without fertilizers, with chemical fertilizers only, and with chemical fertilizers as well as two levels (7.5 and 22.5 tons ha(-1)) of rice straw compost), we collected the floodwater samples once every 10 d during the cropping season throughout 3 y and mainly classified aquatic organisms in the floodwater at the order level. The frequency of the presence of Chlorococcales, Lemanaceae, Euglenida, Oligotrichida, Pharyngophorida, Sessilida, Turbellaria, Podocopida, and Cyclopoida was significantly different among the plots, while the maximum population density was significantly different for Cladocera and Cyclopoida among the plots. The effects of the sampling year on the frequency of presence and the maximum population density were also observed. The floodwater samples after midseason drainage in three plots with fertilizer application differed from the samples in the plot without fertilizer application in the community structure of aquatic organisms. Principal component analysis showed that Lemanaceae, Pharyngophorida, and Turbellaria were important components in the floodwater samples after midseason drainage in the three plots with fertilizer application. Although Cladocera appeared more abundantly after midseason drainage in the plot without fertilizers and the plot with chemical fertilizers only, it appeared more abundantly before midseason drainage in the two plots with composts. Shannon-Weaver's index of diversity (H') was higher in the three plots with fertilizers than in the plot without fertilizers. The effect of fertilizer application on the community structure and the diversity of aquatic organisms was more conspicuous than that of the sampling year.
• Permanganate oxidation of ergosterol
  作者：M. Anastasia、A. Fiecchi、A. Scala

  DOI：10.1021/jo01335a008

  日期：1979.10