(22E,24R)-ergosta-4,6,8(14),22-tetraen-3,15-dione | 234757-14-3

• 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: (22E,24R)-ergosta-4,6,8(14),22-tetraen-3,15-dione
• 英文别名: gymnasterone D；(9R,10R,13R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,9,11,12,16,17-hexahydro-1H-cyclopenta[a]phenanthrene-3,15-dione
• CAS: 234757-14-3
• 化学式: C₂₈H₃₈O₂
• 分子量: 406.609
• InChiKey: GQXHQDCLIABAJK-FYQXRWMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  gymnasterone C 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以0.7 mg的产率得到(22E,24R)-ergosta-4,6,8(14),22-tetraen-3,15-dione
  参考文献：
  名称：

  Variation in Cytostatic Constituents of a Sponge-Derived Gymnascella dankaliensis by Manipulating the Carbon Source

  摘要：

  The Halichondria sponge-derived fungus, Gymnacella dankaliensis, was cultured in two different media conditions. A modified malt extract medium containing soluble starch instead of glucose resulted in two extremely unusual steroids, dankasterones A (2) and B (3), while four additional unusual steroids, gymnasterones A (4), B (5), C (6), and D (7), were isolated from the original malt extract medium. Their stereostructures have been established on the basis of spectroscopic analyses along with X-ray crystal structure analyses, modified Mosher's method, CD exciton method, and a chemical transformation. All the steroids except for 4 exhibited significant growth inhibition against the murine P388 cancer cell line. Dankasterone A (2) also exhibited potent growth inhibition against human cancer cell lines.

  DOI：

  10.1021/np070165m

文献信息

• Variation in Cytostatic Constituents of a Sponge-Derived <i>Gymnascella dankaliensis</i> by Manipulating the Carbon Source
  作者：Taro Amagata、Makoto Tanaka、Takeshi Yamada、Mitsunobu Doi、Katsuhiko Minoura、Hirofumi Ohishi、Takao Yamori、Atsushi Numata

  DOI：10.1021/np070165m

  日期：2007.11.1

  The Halichondria sponge-derived fungus, Gymnacella dankaliensis, was cultured in two different media conditions. A modified malt extract medium containing soluble starch instead of glucose resulted in two extremely unusual steroids, dankasterones A (2) and B (3), while four additional unusual steroids, gymnasterones A (4), B (5), C (6), and D (7), were isolated from the original malt extract medium. Their stereostructures have been established on the basis of spectroscopic analyses along with X-ray crystal structure analyses, modified Mosher's method, CD exciton method, and a chemical transformation. All the steroids except for 4 exhibited significant growth inhibition against the murine P388 cancer cell line. Dankasterone A (2) also exhibited potent growth inhibition against human cancer cell lines.