arthrinin A | 1328884-44-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: arthrinin A
• 英文别名: (1R,8S,9S,12R,15R,17S)-6-ethenyl-3,8-dihydroxy-5,12-dimethyl-10-oxapentacyclo[7.7.1.01,15.02,7.012,17]heptadeca-2,4,6-trien-11-one
• CAS: 1328884-44-1
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: BPOZHKIQPZGPLK-RVBQMODWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  arthrinin A 、 甲氧基-三氟甲基苯 以 氘代吡啶 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Arthrinins A–D: Novel diterpenoids and further constituents from the sponge derived fungus Arthrinium sp.

  摘要：

  Bioassay-guided fractionation of a methanolic extract of the fungus Arthrinium sp., isolated from the Mediterranean sponge Geodia cydonium, afforded 10 natural products including five new diterpenoids, arthrinins A-D (1-4) and myrocin D (5). In addition, five known compounds were obtained, which included myrocin A (6), norlichexanthone (7), anomalin A (8), decarboxycitrinone (9) and 2,5-dimethyl-7-hydroxychromone (10). The structures of all isolated compounds were unambiguously elucidated based on extensive 1D and 2D NMR and HR-MS analyzes. The absolute configuration of arthrinins A-D (1-4) was established by the convenient Mosher method performed in NMR tubes and by interpretation of the ROESY spectra. Antiproliferative activity of the isolated compounds was assessed in vitro against four different tumor cell lines, including mouse lymphoma (L5178Y), human chronic myelogenous leukemia (K562), human ovarian cancer (A2780) and cisplatin-resistant ovarian cancer cells (A2780CisR), using the MTT assay. Norlichexanthone (7) and anomalin A (8) exhibited the strongest activities with IC50 values ranging from 0.40 to 74.0 mu M depending on the cell line investigated. This was paralleled by the inhibitory activity of both compounds against 16 cancer related protein kinases including aurora-B, PIM1, and VEGF-R2. In vitro IC50 values of 7 and 8 against these three protein kinases ranged from 0.3 to 11.7 mu M. Further investigation of the potential antitumoral activity of compounds 5-8 was performed in an in vitro angiogenesis assay against human umbilical vascular endothelial cells (HUVEC) sprouting induced by vascular endothelial growth factor A (VEGF-A). Anomalin A (8), myrocin D (5) and myrocin A (6) inhibited VEGF-A dependent endothelial cell sprouting with IC50 values of 1.8, 2.6 and 3.7 mu lM, respectively, whereas norlichexanthone (7) was inactive. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.013