isobrucein A | 57629-50-2

• 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: isobrucein A
• 英文别名: methyl (1R,2S,3R,6R,8S,12S,13S,14R,15R,16S,17S)-12,15,16-trihydroxy-9,13-dimethyl-3-(3-methylbutanoyloxy)-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate
• CAS: 57629-50-2
• 化学式: C₂₆H₃₄O₁₁
• 分子量: 522.549
• InChiKey: NTBOLWMPXFGUHO-FTSLJJEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.77
• 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：

  在 manganese(IV) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以3 mg的产率得到isobrucein A
  参考文献：
  名称：

  Structures of New Quassinoid Glycosides, Yadanziosides A, B, C, D, E, G, H, and New Quassinoids, Dehydrobrusatol and Dehydrobruceantinol fromBrucea javanica(L.) MERR

  摘要：

  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。

  DOI：

  10.1246/bcsj.58.2680

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。
• 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。
• Delaumonones A and B, New Antiplasmodial Quassinoids from Laumoniera bruceadelpha
  作者：Shiori Oshimi、Aki Takasaki、Yusuke Hirasawa、Takahiro Hosoya、Khalijah Awang、A. Hamid A. Hadi、Wiwied Ekasari、Aty Widyawaruyanti、Hiroshi Morita

  DOI：10.1248/cpb.57.867

  日期：——

  New quassinoids, delaumonones A (1) and B (2) have been isolated from the bark of Laumoniera bruceadelpha NOOTEBOOM (Simaroubaceae) and the structures were elucidated by 2D NMR analysis and a chemical correlation. Delaumonones showed an antimalarial activity against Plasmodium falciparum.

  新的类胡萝卜素，月桂烯酮A（1）和B（2）已从Laumoniera bruceadelpha NOOTEBOOM（Simaroubaceae）的树皮中分离出来，并通过2D NMR分析和化学相关性阐明了其结构。十二烷显示出对恶性疟原虫的抗疟活性。