Pereda-Miranda R, Hernández L, Villavicencio M J, Novelo M, Ibarra P, Chai H, Pezzuto J M
Departamento de Farmacia, Facultad de Química, Universidad Nacional Autónoma de México, D.F.
J Nat Prod. 1993 Apr;56(4):583-93. doi: 10.1021/np50094a019.
By bioactivity-directed fractionation, three new antimicrobial and cytotoxic 5,6-dihydro-alpha-pyrones, pectinolides A-C, have been isolated from Hyptis pectinata (Lamiaceae). The absolute stereochemistry of pectinolide A [1] was established as 6S-[(3S-acetyloxy)-1Z-heptenyl]-5S-(acetyloxy)-5 ,6-dihydro-2H-pyran-2-one, on the basis of spectral, chiroptical, and chemical evidence. The structures of pectinolides B [2] and C [3] were determined as the monodeacetylated forms of 1 by comparison of their spectral data and chemical correlation with the prototype compound. Staphylococcus aureus and Bacillus subtilis were sensitive to pectinolide A [1] in the concentration range of 6.25-12.5 micrograms/ml. Compounds 1-3 exhibited significant cytotoxic activity (ED50 < 4 micrograms/ml) against a variety of tumor cell lines.
通过生物活性导向分离，从假荆芥（唇形科）中分离出了三种新的具有抗菌和细胞毒性的5,6-二氢-α-吡喃酮，即果胶内酯A - C。基于光谱、旋光和化学证据，果胶内酯A [1]的绝对立体化学结构被确定为6S - [(3S - 乙酰氧基)-1Z - 庚烯基]-5S - (乙酰氧基)-5,6 - 二氢-2H - 吡喃-2 - 酮。通过比较果胶内酯B [2]和C [3]的光谱数据以及与原型化合物的化学相关性，它们的结构被确定为1的单去乙酰化形式。金黄色葡萄球菌和枯草芽孢杆菌在6.25 - 12.5微克/毫升的浓度范围内对果胶内酯A [1]敏感。化合物1 - 3对多种肿瘤细胞系表现出显著的细胞毒性活性（半数有效剂量ED50 < 4微克/毫升）。
