Petreska Jasmina, Stefkov Gjose, Kulevanova Svetlana, Alipieva Kalina, Bankova Vassya, Stefova Marina
Institute of Chemistry, Faculty of Science, Ss. Cyril and Methodius University, Skopje, Republic of Macedonia.
Nat Prod Commun. 2011 Jan;6(1):21-30.
Twenty-one samples of Sideritis species (S. scardica, S. raeseri, S. taurica, S. syriaca and S. perfoliata) from various locations on the Balkan Peninsula were evaluated for their chemical constituents. Chemical analyses were focused on secondary metabolites, particularly phenolic compounds, which have several roles in the plant physiological processes and have demonstrated significant health beneficial effects. The occurrence of hydroxycinnamic acids, phenylethanoid glycosides and flavonoids has been investigated in taxonomically related taxa of the genus Sideritis. A systematic method for phenolic compounds identification was developed using tandem mass spectrometry coupled to high performance liquid chromatography with diode array detection. Scanning for precursor ions of commonly found phenolics in Sideritis species using LC/MS11 with an ion trap instrument permitted the specific determination of hydroxycinnamic acid derivatives, and phenylethanoid and flavonoid glycosides. Further characterization of each phenolic compound was performed using MS/MS product-ion analysis and common-neutral-loss analysis. This on-line technique allowed identification of three hydroxycinnamic acid derivatives, eight phenylethanoid glycosides, and twenty-four flavonoid glycosides. All the taxa analysed produced very similar phenolic patterns characterized by the presence of 5-caffeoylquinic acid, lavandulifolioside, verbascoside, hypolaetin 7-O-[6'''-O-acetyl]-allosyl(1-->2)glucoside, apigenin 7-(4"-p-coumaroylglucoside), 4'-O-methylisoscutellarein 7-O-[6'''-O-acetyl]-allosyl(1-->2)glucoside, and minor amounts of isoverbascoside, apigenin 7-O-allosyl(1-->2)glucoside, isoscutellarein 7-O-allosyl-(1-->2)-[6"-O-acetyl]-glucoside, hypolaetin 7-O-allosyl-(1-->2)-[6"-O-acetyl]-glucoside and 4'-O-methylhypolaetin 7-O-[6'''-O-acetyl]-allosyl-(1-->2)-[6"-O-acetyl]-glucoside. These results show that the investigated species are systematically very closely related. Phenylethanoid glycosides and flavonoid acetylglycosides are dominant and constitute 90% of the total phenolic compounds compared with hydroxycinnamic acid and flavonoid 7-O-glycosides. Principal component analysis (PCA) was performed for the nature and content of the different compounds to be correlated to the particular Sideritis species and also to the locations.
对来自巴尔干半岛不同地点的21个铁角蕨属物种样本（铁角蕨、雷氏铁角蕨、 Taurica铁角蕨、叙利亚铁角蕨和贯穿叶铁角蕨）进行了化学成分评估。化学分析集中在次生代谢产物，特别是酚类化合物，其在植物生理过程中发挥多种作用，并已证明具有显著的健康益处。已对铁角蕨属分类学相关类群中羟基肉桂酸、苯乙醇苷和黄酮类化合物的存在情况进行了研究。开发了一种使用串联质谱与带二极管阵列检测的高效液相色谱联用的酚类化合物鉴定系统方法。使用带离子阱仪器的LC/MS11扫描铁角蕨属物种中常见酚类的前体离子，可特异性测定羟基肉桂酸衍生物以及苯乙醇苷和黄酮苷。使用MS/MS产物离子分析和常见中性丢失分析对每种酚类化合物进行进一步表征。这种在线技术鉴定出了三种羟基肉桂酸衍生物、八种苯乙醇苷和二十四种黄酮苷。所有分析的类群产生的酚类模式非常相似，其特征是存在5-咖啡酰奎宁酸、薰衣草苷、毛蕊花糖苷、异槲皮素7-O-[6'''-O-乙酰基]-阿洛糖基(1→2)葡萄糖苷、芹菜素7-(4''-对香豆酰葡萄糖苷)、4'-O-甲基异黄芩素7-O-[6'''-O-乙酰基]-阿洛糖基(1→2)葡萄糖苷，以及少量的异毛蕊花糖苷、芹菜素7-O-阿洛糖基(1→2)葡萄糖苷、异黄芩素7-O-阿洛糖基-(1→2)-[6''-O-乙酰基]-葡萄糖苷、异槲皮素7-O-阿洛糖基-(1→2)-[6''-O-乙酰基]-葡萄糖苷和4'-O-甲基异槲皮素7-O-[6'''-O-乙酰基]-阿洛糖基-(1→2)-[6''-O-乙酰基]-葡萄糖苷。这些结果表明，所研究的物种在系统发育上非常密切相关。与羟基肉桂酸和黄酮7-O-糖苷相比，苯乙醇苷和黄酮乙酰糖苷占主导地位，占总酚类化合物的90%。对不同化合物的性质和含量进行了主成分分析（PCA），以关联到特定的铁角蕨属物种以及产地。
