Knödler Matthias, Conrad Jürgen, Wenzig Eva M, Bauer Rudolf, Lacorn Markus, Beifuss Uwe, Carle Reinhold, Schieber Andreas
Institute of Food Science and Biotechnology, Section Plant Foodstuff Technology, Hohenheim University, August-von-Hartmann Strasse 3, D-70599 Stuttgart, Germany.
Phytochemistry. 2008 Feb;69(4):988-93. doi: 10.1016/j.phytochem.2007.10.013. Epub 2007 Dec 21.
Bioassay directed extraction and purification of mango peels revealed the 5-(11'Z-heptadecenyl)-resorcinol (1) and the known 5-(8'Z,11'Z-heptadecadienyl)-resorcinol (2) previously not described in Mangifera indica L. The structures of both compounds were determined by extensive 1D and 2D NMR studies and MS. Both compounds exhibited potent cyclooxygenase (COX)-1 and COX-2 inhibitory activity with IC(50) values ranging from 1.9 (2) to 3.5 microM (1) and from 3.5 (2) to 4.4 (1) microM, respectively, coming close to the IC(50) values of reference drugs. 5-Lipoxygenase (5-LOX) catalyzed leukotriene formation was only slightly inhibited. Structure-activity studies by referring to synthetic saturated homologues indicated that the degree of unsaturation in the alkyl chain plays a key role for COX inhibitory activity, whereas the influence of chain length was less significant.
通过生物测定指导的方法对芒果皮进行提取和纯化，发现了5-(11'Z-十七碳烯基)-间苯二酚（1）以及之前在芒果中未被描述过的已知化合物5-(8'Z,11'Z-十七碳二烯基)-间苯二酚（2）。这两种化合物的结构通过广泛的一维和二维核磁共振研究以及质谱分析得以确定。两种化合物均表现出强大的环氧化酶（COX）-1和COX-2抑制活性，其半数抑制浓度（IC50）值分别为1.9（2）至3.5微摩尔/升（1）以及3.5（2）至4.4（1）微摩尔/升，接近参考药物的IC50值。5-脂氧合酶（5-LOX）催化的白三烯形成仅受到轻微抑制。通过参考合成的饱和同系物进行的构效关系研究表明，烷基链中的不饱和度程度对COX抑制活性起着关键作用，而链长的影响则不太显著。
