姜黄中1个新的裂环没药烷型倍半萜成分

目的研究姜黄Curcuma longa的化学成分及其生物活性。方法采用硅胶柱色谱、制备薄层色谱和半制备高效液相色谱等分离技术进行分离纯化,运用多种现代波谱技术对化合物进行结构鉴定,并通过NOESY和计算NMR确定其相对构型,计算电子圆二色谱(electrostatic circular dichroism,ECD)确定其绝对构型。采用KCl预收缩的大鼠胸主动脉环模型对分离得到的化合物进行舒张血管活性评价。结果从姜黄95%乙醇提取物中分离得到1个新的裂环没药烷型倍半萜成分,鉴定为(1S,6S,7R)-3,4-裂环没药烷-10-烯-3,9-二酮-1,4-内酯(1),活性评价显示该化合物对KCl预收缩的大鼠胸主动脉环无舒张作用。结论化合物1为从姜黄中分离得到的新化合物,命名为姜黄烷G,其在没药烷型骨架的基础上,C-4-C-3经氧化断裂后,4-COOH与1-OH成酯形成五元内酯环结构。

A new seco-bisabolane-type sesquiterpenoid from Curcuma longa

Objective To study the chemical constituents and bioactivity of Curcuma longa. Methods The chemical compounds of the 95% ethanolic extract of the rhizomes of C. longa were separated and purified by silica gel column chromatography, preparative TLC, and semi-preparative HPLC. The structure of the compound was elucidated by means of various spectroscopic techniques. The relative and absolute configurations were established by NOESY correlations, calculating NMR chemical shifts, and calculating electrostatic circular dichroism (ECD) spectrum. In addition, the KCl pre-contracted rat aortic ring model was applied to evaluate the vasorelaxant activity of the isolated compound. Results A new seco-bisabolene-type sesquiterpenoid was obtained from C. longa, which was determined to be (1S,6S,7R)-3,4-seco-bisabol-10-ene-3,9-dion-1,4-olide (1). It showed no significant vasorelaxant effect on the rat thoracic aortic ring pre-contracted by KCl. Conclusion Compound 1 named curcumane G, was a new seco-bisabolane isolated from C. longa. After oxidation and cleavage of the C-4-C-3 bond on the bisabolane skeleton in compound 1, a butyrolactone ring was formed through an ester bond between 4-COOH and 1-OH.