25-环木菠萝烯-3,24-二醇 | 99946-06-2

• 物质功能分类: 天然产物 - 萜类
• 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
• 中文名称: 25-环木菠萝烯-3,24-二醇
• 英文名称: cycloart-25-en-3b,24-diol
• 英文别名: (24R/S)-9,19-cyclolanost-25-ene-3β,24-diol；3β-hydroxy-25-methylenecycloartan-24-ol；(3β)-9,19-cyclolanost-25-ene-3,24-diol；3β,24ξ-dihydroxycycloart-25-ene；(24RS)-cycloart-25-en-3β,24-diol；cycloart-25-ene-3β,24-diol；Cycloart-25-ene-3,24-diol；(1S,3R,6S,8R,11S,12S,15R,16R)-15-[(2R)-5-hydroxy-6-methylhept-6-en-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.01,3.03,8.012,16]octadecan-6-ol
• CAS: 99946-06-2；99946-09-5；10388-48-4
• 化学式: C₃₀H₅₀O₂
• 分子量: 442.726
• InChiKey: MHGLNDDJLDJDBG-GSYFYXRESA-N

物化性质

• 熔点：
  200-203 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  537.7±23.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 25-环木菠萝烯-3,24-二醇 在 吡啶 作用下， 反应 0.03h， 以86%的产率得到(24R/S)-9,19-cyclolanost-25-ene-3β,24-diol diacetate
  参考文献：
  名称：

  Jayakumar; Ajithabai; Santhosh, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 2, p. 429 - 431

  摘要：

  DOI：
• 作为产物：
  描述：

  9,19-cyclolanostan-3-one 在 吡啶 、 lithium aluminium tetrahydride 、 hematoporphyrin 、 氧气 作用下， 以 乙醚 为溶剂， 反应 4.0h， 生成 25-环木菠萝烯-3,24-二醇
  参考文献：
  名称：

  Cytotoxic Triterpenoids from the Leaves ofEuphorbia pulcherrima

  摘要：

  从 Euphorbia pulcherrima 中分离出了两种具有细胞毒性的三萜类化合物。通过核磁共振、红外光谱和质谱分析，确定了它们的结构和立体化学性质。这些化合物被鉴定为 9,19-环木菠萝烯-23-烯-3δ²,25-二醇和 9,19-环木菠萝烯-25-烯-3δ²,24-二醇。使用艾氏腹水瘤细胞进行了细胞毒性评估。环木菠萝烯醇对艾氏腹水瘤细胞没有诱导细胞毒性活性，而两种分离出的三萜类化合物都表现出细胞失活作用。9,19-环木菠萝烯-25-烯-3δ²,24-二醇的 IC50 约为 7.5 µM，IC90 约为 13.5 µM。3δ²,25-二醇化合物的活性要低 50%。

  DOI：

  10.1055/s-2006-957893

文献信息

• Biotransformation of Cycloartane-Type Triterpenes by the Fungus <i>Glomerella </i><i>f</i><i>usarioides</i>
  作者：Toshihiro Akihisa、Kenji Watanabe、Risa Yoneima、Takashi Suzuki、Yumiko Kimura

  DOI：10.1021/np058120d

  日期：2006.4.1

  Biotransformation of three cycloartane-type triterpenes, cycloartenol (1), 24-methylenecycloartanol (2), and cycloartenone (3), by the fungus Glomerella fusarioides was studied. Compound 1 was converted to 3, cycloart-25-ene-3 beta, 24-diol (4), and cycloartane-3 beta, 24,25-triol (5). Compound 2 was metabolized to cycloeucalenol (6) and two new compounds, 24-methylcycloartane-3 beta,24,24(1)-triol (7) and 24(1)-methoxy-24-methylcycloartane-3 beta, 24-diol (8). Compound 3 was converted into two new metabolites, 4 alpha,4 beta,14 alpha-trimethyl-9 beta, 19-cyclopregnane-3,20-dione (9) and 25-hydroxy-24-methoxycycloartan-3-one (14), and four known compounds, viz., cycloartane-3,24-dione (10), 24-hydroxycycloart-25-en-3-one (11), (23E)-25-hydroxycycloart-23-en-3-one (12), and 24,25-dihydroxycycloartan-3-one (13). The structures of four new metabolites, 7, 8, 9, and 14, were established by spectroscopic methods.
• Barik; Bhaumik; Dey, Journal of the Indian Chemical Society, 1997, vol. 74, # 2, p. 163 - 164
  作者：Barik、Bhaumik、Dey、Kundu

  DOI：——

  日期：——
• Cytotoxic Triterpenoids from the Leaves of<i>Euphorbia pulcherrima</i>
  作者：I. Smith-Kielland、J. Dornish、K. Malterud、G. Hvistendahl、Chr. Rømming、O. Bøckmann、P. Kolsaker、Y. Stenstrøm、A. Nordal

  DOI：10.1055/s-2006-957893

  日期：1996.8

  Two cytotoxic triterpenes have been isolated from Euphorbia pulcherrima. Their structures and stereochemistry have been established from NMR, IR, and El-mass spectroscopy. The compounds were identified as 9,19-cycloart-23-ene-3β,25-diol and 9,19-cycloart-25-ene-3β,24-diol. Cytotoxicity evaluation was performed using Ehrlich ascites tumor cells. While cycloartenol induced no cytotoxic activity against Ehrlich ascites tumor cells, both isolated triterpenes exhibited cell inactivating effects. The IC50 is approximately 7.5 µM, while the IC90 is approximately 13.5 µM for 9,19-cycloart-25-ene-3β,24-diol. The 3β,25-diol compound is 50 % less active.

  从 Euphorbia pulcherrima 中分离出了两种具有细胞毒性的三萜类化合物。通过核磁共振、红外光谱和质谱分析，确定了它们的结构和立体化学性质。这些化合物被鉴定为 9,19-环木菠萝烯-23-烯-3δ²,25-二醇和 9,19-环木菠萝烯-25-烯-3δ²,24-二醇。使用艾氏腹水瘤细胞进行了细胞毒性评估。环木菠萝烯醇对艾氏腹水瘤细胞没有诱导细胞毒性活性，而两种分离出的三萜类化合物都表现出细胞失活作用。9,19-环木菠萝烯-25-烯-3δ²,24-二醇的 IC50 约为 7.5 µM，IC90 约为 13.5 µM。3δ²,25-二醇化合物的活性要低 50%。
• Jayakumar; Ajithabai; Santhosh, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 2, p. 429 - 431
  作者：Jayakumar、Ajithabai、Santhosh、Veena、Nairt, Mangalam S.

  DOI：——

  日期：——