Carabron | 1748-81-8

• 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 - 异戊烯醇脂质
• 英文名称: Carabron
• 英文别名: 5a-Methyl-3-methylidene-5-(3-oxobutyl)-3a,4,4a,5,6,6a-hexahydrocyclopropa[f][1]benzofuran-2-one
• CAS: 1748-81-8；19956-59-3
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: AGIQIKMGJVLKMA-UHFFFAOYSA-N

物化性质

• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

制备方法与用途

生物活性

Carabrone 天名精内酯酮是从 Carpesium abrotanoides 的果实中分离出来的一种倍半萜，具有显著的抗菌和抗肿瘤活性。

Carabrone 在体内外均展现出抗真菌活性，具体包括对灰霉病菌 Botrytis cinerea、炭疽病菌 Colletotrichum lagenarium 和禾白粉菌 Erysiphe graminis 的抑制作用。

靶点

• EC50: 7.10 μg/mL（针对 Colletotrichum lagenarium）

反应信息

• 作为反应物：
  描述：

  Carabron 在 4-二甲氨基吡啶 、 sodium acetate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 36.0h， 生成 N-(2-(2-(((4-(5a-methyl-3-methylene-2-oxooctahydro-2H-cyclopropa[f]benzofuran-5-yl)butan-2-ylidene)amino)oxy)-acetamido)ethyl)-2-(methylamino)benzamide
  参考文献：
  名称：

  Mitochondrial Signs and Subcellular Imaging Provide Insight into the Antifungal Mechanism of Carabrone against Gaeumannomyces graminis var. tritici

  摘要：

  Carabrone, a botanical bicyclic sesquiterpenic lactone, has broad-spectrum antifungal activity and is particularly efficient against the devastating phytopathogen Gaeumannomyces graminis var. tritici (Ggt). The antifungal mechanism of carabrone against Ggt, however, remains unclear. The main objective of this study was to investigate the subcellular localization of carabrone in Ggt to gain a better understanding of its mechanism of action. When Ggt was exposed to carabrone (EC50 value of 28.45 mu g/mL) for 7 days, a decline in mitochondrial concentration together with some obvious alternations in mitochondrial structure, including hazy outlines, medullary transitions, excess accumulation of unclear settlings, and vacuolar degeneration, were observed, indicating that carbrone may act on the mitochondria directly. A fluorescent conjugate (TTY) was thus designed and synthesized as a surrogate of carabrone that possessed comparable antifungal activity against Ggt (EC50 of 33.68 mu g/mL). Additionally, a polyclonal antibody specific to carabrone and with a high titer (256 000) was also prepared by immunizing mice. Subsequently, two imaging techniques, the use of the fluorescent conjugate (FC) and immunofluorescence (IF), were applied to determine the subcellular localization of carabrone. Both FC and IF fluorescent signals demonstrated its mitochondrial localization with a Pearson's coefficient of 0.83 for FC and 0.86 for IF. These results imply that carabrone exerts its antifungal activity against Ggt by interfering with mitochondrial function.

  DOI：

  10.1021/acs.jafc.7b03913

文献信息

• Mitochondrial Signs and Subcellular Imaging Provide Insight into the Antifungal Mechanism of Carabrone against <i>Gaeumannomyces graminis</i> var. <i>tritici</i>
  作者：Lanying Wang、Yunfei Zhang、Delong Wang、Mei Wang、Yong Wang、Juntao Feng

  DOI：10.1021/acs.jafc.7b03913

  日期：2018.1.10

  Carabrone, a botanical bicyclic sesquiterpenic lactone, has broad-spectrum antifungal activity and is particularly efficient against the devastating phytopathogen Gaeumannomyces graminis var. tritici (Ggt). The antifungal mechanism of carabrone against Ggt, however, remains unclear. The main objective of this study was to investigate the subcellular localization of carabrone in Ggt to gain a better understanding of its mechanism of action. When Ggt was exposed to carabrone (EC50 value of 28.45 mu g/mL) for 7 days, a decline in mitochondrial concentration together with some obvious alternations in mitochondrial structure, including hazy outlines, medullary transitions, excess accumulation of unclear settlings, and vacuolar degeneration, were observed, indicating that carbrone may act on the mitochondria directly. A fluorescent conjugate (TTY) was thus designed and synthesized as a surrogate of carabrone that possessed comparable antifungal activity against Ggt (EC50 of 33.68 mu g/mL). Additionally, a polyclonal antibody specific to carabrone and with a high titer (256 000) was also prepared by immunizing mice. Subsequently, two imaging techniques, the use of the fluorescent conjugate (FC) and immunofluorescence (IF), were applied to determine the subcellular localization of carabrone. Both FC and IF fluorescent signals demonstrated its mitochondrial localization with a Pearson's coefficient of 0.83 for FC and 0.86 for IF. These results imply that carabrone exerts its antifungal activity against Ggt by interfering with mitochondrial function.