鸦胆停醇 | 53729-52-5

• 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
• 中文名称: 鸦胆停醇
• 英文名称: bruceantinol
• 英文别名: methyl (1R,2S,3R,6R,8R,13S,14R,15R,16S,17S)-3-[(E)-4-acetyloxy-3,4-dimethylpent-2-enoyl]oxy-10,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate
• CAS: 53729-52-5
• 化学式: C₃₀H₃₈O₁₃
• 分子量: 606.624
• InChiKey: SREUSBYRKOPNJK-AJPRWBMOSA-N

物化性质

• 沸点：
  788.2±60.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  43
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  192
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  yadanzioside K 在 β-glucosidase 作用下， 以 水 为溶剂， 反应 336.0h， 以17 mg的产率得到鸦胆停醇
  参考文献：
  名称：

  Structures of Yadanziosides K, M, N, and O, New Quassinoid Glycosides fromBrucea javanica(L.) MERR

  摘要：

  从Brucea javanica (L.) Merr中分离出了四种新的苦槲皮苷，即yadanziosides K、M、N和O，并通过光谱测量和化学方法确定了它们的结构。研究发现，山丹子苷 O 的苷元对小鼠 P388 淋巴细胞白血病具有显著的抗肿瘤活性，这种苷元可以从布鲁沙醇中制备出来。

  DOI：

  10.1246/bcsj.59.3541

文献信息

• New quassinoid glycosides, yadanziosides A-H, from Brucea javanica.
  作者：Toshiro Sakaki、Shin Yoshimura、Masami Ishibashi、Takahiko Tsuyuki、Takeyoshi Takahashi、Tadashi Honda、Toshihiro Nakanishi

  DOI：10.1248/cpb.32.4702

  日期：——

  Eight new antileukemic quassinoid glycosides, yadanziosides A-H (1-8) were isolated from seeds of Brucea javanica and their structures were determined by chemical transformation and spectral analysis.

  从鸦胆子种子中分离出了八种新的抗白血病类槲皮苷，即yadanziosides A-H（1-8），并通过化学转化和光谱分析确定了它们的结构。
• Screening of Indonesian Medicinal Plant Extracts for Antibabesial Activity and Isolation of New Quassinoids from <i>Brucea javanica</i>
  作者：Subeki、Hideyuki Matsuura、Kosaku Takahashi、Kensuke Nabeta、Masahiro Yamasaki、Yoshimitsu Maede、Ken Katakura

  DOI：10.1021/np070236h

  日期：2007.10.1

  Boiled extracts derived from 28 Indonesian medicinal plants were screened for their antibabesial activity against Babesia gibsoni in vitro. Of these extracts, the fruit of Brucea javanica was the most active in inhibiting parasite growth at a concentration of 10 mu g/mL. Bioassay-guided fractionation of the fruit extract of Br. javanica led to the isolation of two new quassinoids, bruceantinol B and bruceine J, and the structures of these compounds were elucidated on the basis of their spectroscopic data and by chemical transformation to known compounds. In addition, the known quassinoids bruceines A-D, bruceantinol, and yadanziolide A were isolated. Antibabesial activities were also examined in vitro, and bruceine A and bruceantinol were shown to be more potent than diminazene aceturate, a drug IC50 = 103 ng/mL) used clinically against B. gibsoni, with IC50 values of 4 and 12 ng/mL, respectively.