methyl (1R,2S,3R,6R,8S,12S,13S,14R,15R,16S,17S)-12,15,16-trihydroxy-9,13-dimethyl-3-(3-methylbut-2-enoyloxy)-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate | 99133-04-7

• 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
• 英文名称: methyl (1R,2S,3R,6R,8S,12S,13S,14R,15R,16S,17S)-12,15,16-trihydroxy-9,13-dimethyl-3-(3-methylbut-2-enoyloxy)-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate
• CAS: 99133-04-7
• 化学式: C₂₆H₃₂O₁₁
• 分子量: 520.533
• InChiKey: DNWFJHUEOKYIAM-FTSLJJEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  37
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  166
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  (1β,2α,11β,12α,15β)-13,20-epoxy-1,2,11,12-tetrahydroxy-16-oxo-15-(senecioyloxy)picras-3-en-21-oic acid methyl ester 在 manganese(IV) oxide 作用下， 生成 methyl (1R,2S,3R,6R,8S,12S,13S,14R,15R,16S,17S)-12,15,16-trihydroxy-9,13-dimethyl-3-(3-methylbut-2-enoyloxy)-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate
  参考文献：
  名称：

  New quassinoid glycosides, yadanziosides A-H, from Brucea javanica.

  摘要：

  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。

  DOI：

  10.1248/cpb.32.4702

文献信息

• Structures of New Quassinoid Glycosides, Yadanziosides A, B, C, D, E, G, H, and New Quassinoids, Dehydrobrusatol and Dehydrobruceantinol from<i>Brucea javanica</i>(L.) MERR
  作者：Toshiro Sakaki、Shin Yoshimura、Masami Ishibashi、Takahiko Tsuyuki、Takeyoshi Takahashi、Tadashi Honda、Toshihiro Nakanishi

  DOI：10.1246/bcsj.58.2680

  日期：1985.9

  Quassinoid glycosides, yadanziosides A, B, C, D, E, G, and H, and two quassinoids, dehydrobrusatol and dehydrobruceantinol were isolated from seeds of Brucea javanica, and their structures were determined. These glycosides showed bitter taste and were demonstrated to have antileukemic activity.

  从Brucea javanica种子中分离出了槲皮苷--yadanziosides A、B、C、D、E、G和H，以及两种槲皮苷--dehydrobrusatol和dehydrobruceantinol，并确定了它们的结构。这些苷具有苦味，并被证明具有抗白血病活性。
• Inhibitory Effects of Quassinoid Derivatives on Epstein-Barr Virus Early Antigen Activation.
  作者：Shakila RAHMAN、Narihiko FUKAMIYA、Nobuhiro OHNO、Harukuni TOKUDA、Hoyoku NISHINO、Kiyoshi TAGAHARA、Kuo-Hsiung LEE、Masayoshi OKANO

  DOI：10.1248/cpb.45.675

  日期：——

  Short-term in vitro assays for tumor promoters and antitumor promoters (Epstein-Barr virus activation test) were carried out for semisynthetic quassinoids (3-7), which were obtained by esterification of the C-15 OH group of deacetylated isobrucein-B (2). All the ester derivatives showed higher antitumor promoting activity than that of the potent compound 2. A compound containing a fluorinated aliphatic ester showed the highest potency.

  对半合成喹啉类化合物（3-7）进行了肿瘤促进剂和抗肿瘤促进剂的短期体外试验（Epstein-Barr病毒激活试验），这些化合物是通过脱乙酰基异布鲁辛-B（2）的C-15 OH基团酯化获得的。所有酯类衍生物的抗肿瘤促进活性均高于强效化合物2。一种含有氟代脂肪族酯的化合物显示出最高的效力。