Fragoso-Serrano Mabel, Gibbons Simon, Pereda-Miranda Rogelio
Departamento de Farmacia. Facultad de Química. Universidad Nacional Autónoma de México, University City, 04510 DF Mexico City, Mexico.
Planta Med. 2005 Mar;71(3):278-80. doi: 10.1055/s-2005-837831.
Bioassay-guided fractionation of a CHCl (3) extract prepared from the Mexican medicinal plant Hyptis pectinata led to the isolation of four pyrones, pectinolides A-C ( 1-3) and H ( 4). Activity was tracked using cultured KB cells. Multidrug-resistant strains of Staphylococcus aureus were sensitive to pectinolide H ( 4; KB > 20 microg/mL) in the concentration range of 32-64 microg/mL. The absolute stereochemistry of this new compound was established as 5 S-[(4 S-acetyloxy)-(1 S-hydroxy)-2 Z-octenyl]-2(5 H)-furanone on the basis of spectral, chiroptical data and chemical correlation with pectinolide A ( 1). Mosher ester derivatives were used with pectinolide B ( 2) for confirmation of the 3'-( S) absolute stereochemistry on the side chain chiral center of pectinolides A-C.
对从墨西哥药用植物具缘香科塔草制备的氯仿提取物进行生物测定导向的分级分离，得到了四种吡喃酮，即具缘内酯A - C（1 - 3）和H（4）。使用培养的KB细胞追踪活性。耐多药金黄色葡萄球菌菌株在32 - 64μg/mL浓度范围内对具缘内酯H（4；KB＞20μg/mL）敏感。基于光谱、旋光数据以及与具缘内酯A（1）的化学关联，确定该新化合物的绝对立体化学结构为5S - [(4S - 乙酰氧基)-(1S - 羟基)-2Z - 辛烯基]-2(5H)-呋喃酮。使用莫舍尔酯衍生物与具缘内酯B（2）来确证具缘内酯A - C侧链手性中心上3'-(S)的绝对立体化学结构。
