Zardi-Bergaoui Afifa, Znati Mansour, Harzallah-Skhiri Fethia, Jannet Hichem Ben
Laboratory of Heterocyclic Chemistry, Natural Products and Reactivity (LR11ES39), Team: Medicinal Chemistry and Natural Products, Faculty of Science of Monastir, University of Monastir, Avenue of Environment, 5019, Monastir, Tunisia.
Laboratory of Genetics Biodiversity and Valorization of Bioresources (LR11ES41), Higher Institute of Biotechnology of Monastir, University of Monastir, Monastir, Rue Tahar Haddad, 5000, Monastir, Tunisia.
Chem Biodivers. 2019 Feb;16(2):e1800483. doi: 10.1002/cbdv.201800483. Epub 2019 Jan 23.
A new caryophyllene, named pulicaryenne A (1), along with four other known caryophyllene derivatives (2, 3, 4 and 5) were isolated from the ethyl acetate extract of aerial parts of Pulicaria vulgaris Gaertn. (Asteraceae). All compounds were isolated for the first time from this species. Compound 2 was identified as a new epimer of a known caryophyllene derivative isolated previously from P. dysenterica. Their structures were established by spectroscopic means including NMR analysis (1D- and 2D-NMR) and ESI-TOF-MS. All compounds were evaluated for their anticholinesterase, antityrosinase and cytotoxic activities against two human cell lines (A549 and HeLa). Results showed that compound 5 exhibited the highest cytotoxic effect against A549 and anticholinesterase activity with IC values of 8.50±0.75 and 6.45±0.09 μg/mL, respectively. Furthermore, compound 5 showed also an interesting antityrosinase activity with percent inhibition value of 79.0±2.5 % at 50 μg/mL. The bioactivity and drug likeness scores of the isolated compounds 1-5 were calculated using Molinspiration software and discussed. These results may suggest that the five caryophyllene derivatives endowed with good biological properties, which could be used as bioactive alternatives in pharmaceutical preparations.
从普通旋覆花（菊科）地上部分的乙酸乙酯提取物中分离出一种新的石竹烯，命名为普立卡石竹烯A（1），以及其他四种已知的石竹烯衍生物（2、3、4和5）。所有化合物均首次从该物种中分离得到。化合物2被鉴定为先前从痢疾旋覆花中分离出的一种已知石竹烯衍生物的新差向异构体。通过包括核磁共振分析（一维和二维核磁共振）和电喷雾飞行时间质谱在内的光谱手段确定了它们的结构。评估了所有化合物对两种人类细胞系（A549和HeLa）的抗胆碱酯酶、抗酪氨酸酶和细胞毒性活性。结果表明，化合物5对A549表现出最高的细胞毒性作用和抗胆碱酯酶活性，其IC值分别为8.50±0.75和6.45±0.09μg/mL。此外，化合物5在50μg/mL时还表现出有趣的抗酪氨酸酶活性，抑制率为79.0±2.5%。使用Molinspiration软件计算并讨论了分离出的化合物1-5的生物活性和类药性质评分。这些结果可能表明这五种石竹烯衍生物具有良好的生物学特性，可作为药物制剂中的生物活性替代品。
