3-keto-15-hydroxysclareolide | 1370469-89-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 3-keto-15-hydroxysclareolide
• 英文别名: (3aR,5aR,6R,9aS,9bR)-6-(hydroxymethyl)-3a,6,9a-trimethyl-4,5,5a,8,9,9b-hexahydro-1H-benzo[e][1]benzofuran-2,7-dione
• CAS: 1370469-89-8
• 化学式: C₁₆H₂₄O₄
• 分子量: 280.364
• InChiKey: TTWXZMJCBVELOT-AKUOKLNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  香紫苏内酯 在 spores of Aspergillus niger 作用下， 以 丙酮 为溶剂， 反应 336.0h， 以11.7%的产率得到3-oxosclareolide
  参考文献：
  名称：

  Biotransformation of sclareolide by filamentous fungi: cytotoxic evaluations of the derivatives

  摘要：

  Sclareolide (1) was incubated with eight different species of filamentous fungi conventionally used for bio-oxidations. Compound 1 was metabolized with Aspergillus niger in medium A to yield 3-ketosclareolide (2) and 3 beta-hydroxysclareolide (4), while in medium B (containing major number of nutrients with respect to medium A), compounds 2, 4, 3 alpha,6 beta-dihydroxysclareolide (16), 1-ketosclareolide (17), 3-keto-15-hydroxysclareolide (18) and 3 beta,15-dihydroxysclareolide (19) were obtained. The biotransformation products 16-19 were found to be new substances. Fermentation of 1 with Cunninghamella blackesleeana using medium A afforded 2 and 4, while using medium B yielded 2, 4, 16 and 17. Compounds 2, 4 and 17 were also obtained with Curvularia lunata. Biotransformation of 1 with Beauveria bassiana yielded 4 in satisfactory yield, with Rhizopus oligosporus and Mucor miehei afforded 2 and 4, while with R. nigricans and Fusarium moliniforme yielded 2, 4 and 16. Cytotoxic evaluation of 1 and the obtained products against selected human cancer cell lines (U251, PC-3, K562, HCT-15, MCF-7 and SKUL-1) indicated that 16 (3 alpha,6 beta-dihydroxysclareolide) displayed moderate cytotoxic (IC50 < 100 mu M) against U251, PC-3, HCT-15 and MCF-7.

  DOI：

  10.1590/s0103-50532011000600025

文献信息

• Biotransformation of sclareolide by filamentous fungi: cytotoxic evaluations of the derivatives
  作者：Arturo Cano、María Teresa Ramírez-Apan、Guillermo Delgado

  DOI：10.1590/s0103-50532011000600025

  日期：——

  Sclareolide (1) was incubated with eight different species of filamentous fungi conventionally used for bio-oxidations. Compound 1 was metabolized with Aspergillus niger in medium A to yield 3-ketosclareolide (2) and 3 beta-hydroxysclareolide (4), while in medium B (containing major number of nutrients with respect to medium A), compounds 2, 4, 3 alpha,6 beta-dihydroxysclareolide (16), 1-ketosclareolide (17), 3-keto-15-hydroxysclareolide (18) and 3 beta,15-dihydroxysclareolide (19) were obtained. The biotransformation products 16-19 were found to be new substances. Fermentation of 1 with Cunninghamella blackesleeana using medium A afforded 2 and 4, while using medium B yielded 2, 4, 16 and 17. Compounds 2, 4 and 17 were also obtained with Curvularia lunata. Biotransformation of 1 with Beauveria bassiana yielded 4 in satisfactory yield, with Rhizopus oligosporus and Mucor miehei afforded 2 and 4, while with R. nigricans and Fusarium moliniforme yielded 2, 4 and 16. Cytotoxic evaluation of 1 and the obtained products against selected human cancer cell lines (U251, PC-3, K562, HCT-15, MCF-7 and SKUL-1) indicated that 16 (3 alpha,6 beta-dihydroxysclareolide) displayed moderate cytotoxic (IC50 < 100 mu M) against U251, PC-3, HCT-15 and MCF-7.