Prabhakar Reddy P, Lavekar Aditya G, Suresh Babu K, Ranga Rao R, Shashidhar J, Shashikiran G, Madhusudana Rao J
Natural Products Laboratory, Division of Organic Chemistry-I, Indian Institute of Chemical Technology, Hyderabad 500 607, India.
Bioorg Med Chem Lett. 2010 Apr 15;20(8):2525-8. doi: 10.1016/j.bmcl.2010.02.101. Epub 2010 Mar 3.
Hedychenone, a plant-derived labdane diterpenoid, showed potent in vitro cytotoxic activity against cancerous cells. In the present study, a series of analogues have been synthesized by modification of the furanoid ring, double bond and the vinylic methyl functionality of this natural product lead and evaluated for their cytotoxic activities against human cancer cell lines. The structures of the target compounds were established by IR, (1)H NMR and mass spectral analysis. Majority of the analogues displayed potent activity than the parent compound, hedychenone. Preliminary structure-activity relationship studies indicated that furanoid ring has a greater impact on cytotoxicity than that of the decalone nucleus. However, dimerization through C-8 significantly enhanced the cytotoxic activity of the hedychenone.
半日花二酮是一种植物源半日花烷二萜，对癌细胞显示出强大的体外细胞毒活性。在本研究中，通过修饰该天然产物先导物的呋喃环、双键和乙烯基甲基官能团，合成了一系列类似物，并评估了它们对人癌细胞系的细胞毒活性。通过红外光谱、¹H核磁共振光谱和质谱分析确定了目标化合物的结构。大多数类似物显示出比母体化合物半日花二酮更强的活性。初步的构效关系研究表明，呋喃环比十氢萘核对细胞毒性的影响更大。然而，通过C-8进行二聚化显著增强了半日花二酮的细胞毒活性。
