3,4-二氢-3-羟基-7,9-二甲氧基-3-甲基-1H-萘并[2,3-c]吡喃-5,10-二酮 | 36379-67-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异色满醌
• 中文名称: 3,4-二氢-3-羟基-7,9-二甲氧基-3-甲基-1H-萘并[2,3-c]吡喃-5,10-二酮
• 英文名称: herbarin
• 英文别名: 3-hydroxy-7,9-dimethoxy-3-methyl-1,4-dihydrobenzo[g]isochromene-5,10-dione
• CAS: 36379-67-6
• 化学式: C₁₆H₁₆O₆
• 分子量: 304.299
• InChiKey: MQWLANHTCHDMAR-UHFFFAOYSA-N

物化性质

• 熔点：
  191-193 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• 沸点：
  548.5±50.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)
• LogP：
  2.120 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  3,4-二氢-3-羟基-7,9-二甲氧基-3-甲基-1H-萘并[2,3-c]吡喃-5,10-二酮 在 sodium dithionite 、 2,6-二叔丁基-4-甲基苯酚 作用下， 以 乙酸乙酯 为溶剂， 生成
  参考文献：
  名称：

  Heptaketides from Corynespora sp. Inhabiting the Cavern Beard Lichen, Usnea cavernosa: First Report of Metabolites of an Endolichenic Fungus

  摘要：

  Two new heptaketides, corynesporol (1) and l-hydroxydehydroherbarin (2), along with herbarin (3) were isolated from an endolichenic fungal strain, Corynespora sp. BA-10763, occurring in the cavern beard lichen Usnea cavernosa. The structures of 1-3 were elucidated from their spectroscopic data. Aerial oxidation of corynesporol (1) yielded herbarin (3). Acetylation of I afforded the naphthalene derivative 4, whereas acetylation of 3 gave the corresponding naphthoquinone 6 and dehydroherbarin (5). All compounds were evaluated for their cytotoxicity and ability to inhibit migration of human metastatic breast and prostate cancer cell lines MDA-MB-231 and PC-3M, respectively. Dehydroherbarin (5) inhibited migration of both cell lines at concentrations not toxic to these cell lines. This is the first report of metabolites from an endolichenic fungus.

  DOI：

  10.1021/np070466w
• 作为产物：
  描述：

  7-desmethylherbarin 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 3.0h， 以0.5 mg的产率得到3,4-二氢-3-羟基-7,9-二甲氧基-3-甲基-1H-萘并[2,3-c]吡喃-5,10-二酮
  参考文献：
  名称：

  Maximizing Chemical Diversity of Fungal Metabolites: Biogenetically Related Heptaketides of the Endolichenic Fungus Corynespora sp.

  摘要：

  In an attempt to explore the biosynthetic potential of the endolichenic fungus Corynespora sp. BA-10763, its metabolite profiles under several culture conditions were investigated. When cultured in potato dextrose agar, it produced three new heptaketides, 9-O-methylscytalol A (1), 7-desmethylherbarin (2), and 8-hydroxyherbarin (3), together with biogenetically related metabolites scytalol A (4), 8-O-methylfusarubin (5), scorpinone (6), and 8-O-methylbostrycoidin (7), which are new to this organism, and herbarin (8), it metabolite previously encountered in this fungal strain. The use of malt extract agar as the culture medium led to the isolation of 6, 8, 1-hydroxydehydroherbarin (9), and 1-methoxydehydroherbarin (10), which was found to be in artifact formed during the extraction of the culture medium with methanol. The structures of all new compounds were determined by interpretation of their spectroscopic data and chemical interconversions.

  DOI：

  10.1021/np900684v

文献信息

• Heptaketides from <i>Corynespora</i> sp. Inhabiting the Cavern Beard Lichen, <i>Usnea cavernosa</i>: First Report of Metabolites of an Endolichenic Fungus
  作者：Priyani A. Paranagama、E. M. Kithsiri Wijeratne、Anna M. Burns、Marilyn T. Marron、Malkanthi K. Gunatilaka、A. Elizabeth Arnold、A. A. Leslie Gunatilaka

  DOI：10.1021/np070466w

  日期：2007.11.1

  Two new heptaketides, corynesporol (1) and l-hydroxydehydroherbarin (2), along with herbarin (3) were isolated from an endolichenic fungal strain, Corynespora sp. BA-10763, occurring in the cavern beard lichen Usnea cavernosa. The structures of 1-3 were elucidated from their spectroscopic data. Aerial oxidation of corynesporol (1) yielded herbarin (3). Acetylation of I afforded the naphthalene derivative 4, whereas acetylation of 3 gave the corresponding naphthoquinone 6 and dehydroherbarin (5). All compounds were evaluated for their cytotoxicity and ability to inhibit migration of human metastatic breast and prostate cancer cell lines MDA-MB-231 and PC-3M, respectively. Dehydroherbarin (5) inhibited migration of both cell lines at concentrations not toxic to these cell lines. This is the first report of metabolites from an endolichenic fungus.
• Maximizing Chemical Diversity of Fungal Metabolites: Biogenetically Related Heptaketides of the Endolichenic Fungus <i>Corynespora</i> sp.
  作者：E. M. Kithsiri Wijeratne、Bharat P. Bashyal、Malkanthi K. Gunatilaka、A. Elizabeth Arnold、A. A. Leslie Gunatilaka

  DOI：10.1021/np900684v

  日期：2010.6.25

  In an attempt to explore the biosynthetic potential of the endolichenic fungus Corynespora sp. BA-10763, its metabolite profiles under several culture conditions were investigated. When cultured in potato dextrose agar, it produced three new heptaketides, 9-O-methylscytalol A (1), 7-desmethylherbarin (2), and 8-hydroxyherbarin (3), together with biogenetically related metabolites scytalol A (4), 8-O-methylfusarubin (5), scorpinone (6), and 8-O-methylbostrycoidin (7), which are new to this organism, and herbarin (8), it metabolite previously encountered in this fungal strain. The use of malt extract agar as the culture medium led to the isolation of 6, 8, 1-hydroxydehydroherbarin (9), and 1-methoxydehydroherbarin (10), which was found to be in artifact formed during the extraction of the culture medium with methanol. The structures of all new compounds were determined by interpretation of their spectroscopic data and chemical interconversions.