Bisio Angela, Schito Anna Maria, Ebrahimi Samad Nejad, Hamburger Matthias, Mele Giacomo, Piatti Gabriella, Romussi Giovanni, Dal Piaz Fabrizio, De Tommasi Nunziatina
Dipartimento di Farmacia, Università di Genova, Via Brigata Salerno 13, 16147 Genova, Italy.
Dipartimento di Scienze Chirurgiche e Diagnostiche Integrate, Sezione di Microbiologia, Università di Genova, Largo Rosanna Benzi 8, 16145 Genova, Italy.
Phytochemistry. 2015 Feb;110:120-32. doi: 10.1016/j.phytochem.2014.10.033. Epub 2014 Nov 27.
From the aerial parts of Salvia adenophora Fernald four derivatives of 12-oxo-phytodienoic acid (1-4) together with five clerodane diterpenoids (5, 6, 8-10), and one known diterpene (7) have been isolated. Compounds 1-6 and 8-10 are described for the first time. The structures were established by extensive 1D, 2D NMR and HRESI-TOFMS spectroscopic methods. Finally, the absolute configuration has been established by comparing of experimental and quantum chemical calculation of ECD spectra. Despite a total lack of antimicrobial activity of the plant extract, hinting to the existence of antagonistic interactions in the crude material, three oxylipins (2-4) displayed a promising inhibition on Gram-positive multidrug-resistant clinical strains including Staphylococcus aureus, Streptococcus agalactiae and, particularly, Staphylococcus epidermidis, while the compounds 9 and 10 revealed a specific and strain-dependent activity against S. epidermidis. Interestingly, the inhibition provided by these compounds was independent of the resistance patterns of these pathogens to classic antibiotics. No action was reported on Gram-negative strains nor on Candida albicans. These results confirm that clerodanes and, particularly, prostaglandin-like compounds can be considered as interesting antimicrobial agents deserving further study.
从丹参(Salvia adenophora Fernald)的地上部分分离出了4种12-氧代-植物二烯酸衍生物(1-4)、5种克罗烷二萜(5、6、8-10)以及1种已知的二萜(7)。化合物1-6和8-10首次被描述。通过广泛的一维、二维核磁共振和高分辨电喷雾电离飞行时间质谱光谱方法确定了其结构。最后,通过比较实验和量子化学计算的电子圆二色光谱确定了绝对构型。尽管该植物提取物完全没有抗菌活性,这暗示了粗提物中存在拮抗相互作用,但三种氧化脂质(2-4)对包括金黄色葡萄球菌、无乳链球菌,尤其是表皮葡萄球菌在内的革兰氏阳性多重耐药临床菌株表现出了有前景的抑制作用,而化合物9和10对表皮葡萄球菌显示出了特异性的、依赖菌株的活性。有趣的是,这些化合物提供的抑制作用与这些病原体对经典抗生素的耐药模式无关。未报道对革兰氏阴性菌株和白色念珠菌有作用。这些结果证实,克罗烷二萜,特别是类前列腺素化合物可被视为值得进一步研究的有趣抗菌剂。