Kamarauskaite Justina, Baniene Rasa, Raudone Lina, Vilkickyte Gabriele, Vainoriene Rimanta, Motiekaityte Vida, Trumbeckaite Sonata
Department of Pharmacognosy, Medical Academy, Lithuanian University of Health Sciences, Sukileliu Av. 13, LT-50162 Kaunas, Lithuania.
Laboratory of Biopharmaceutical Research, Institute of Pharmaceutical Technologies, Lithuanian University of Health Sciences, Sukileliu Av. 13, LT-50162 Kaunas, Lithuania.
Antioxidants (Basel). 2021 Sep 1;10(9):1405. doi: 10.3390/antiox10091405.
Caffeoylquinic acids are some of the chemophenetically significant specialized metabolites found in plants of the family Dumort., possessing a broad spectrum of biological activities. As they might be potential mitochondria-targeted antioxidants, effective preparation methods-including extraction, isolation, and purification of caffeoylquinic acids from plant sources-are in great demand. The aim of this study was to fractionate the caffeoylquinic acids from cultivated wormwood ( L.) and silver wormwood ( Nutt.) herb acetone extracts and evaluate their phytochemical profiles, antioxidant activity (radical scavenging and reducing activities), effects on kidney mitochondrial functions, and cytochrome-c-reducing properties. The main findings of our study are as follows: (1) Aqueous fractions purified from wormwood and silver wormwood herb acetone extracts are rich in monocaffeoylquinic acids (chlorogenic acid, neochlorogenic acid, 4--caffeoylquinic acid), while methanolic fractions purified from wormwood and silver wormwood herb acetone extracts are rich in dicaffeoylquinic acids (4,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid). Aqueous fractions purified from wormwood and silver wormwood herb acetone extracts were solely composed of monocaffeoylquinic acids. Methanolic fractions purified from wormwood and silver wormwood herb acetone extracts contained only dicaffeoylquinic acids. (2) Fractions purified from silver wormwood herb acetone extracts stood out as having the greatest content of caffeoylquinic acids. (3) The greatest radical scavenging activity was determined in the dicaffeoylquinic-acid-rich fraction purified from silver wormwood herb acetone extract; the greatest reducing activity was determined in the dicaffeoylquinic-acid-rich fraction purified from wormwood herb acetone extract. (4) The effect of both fractions on mitochondrial functions was dose-dependent; lower concentrations of caffeoylquinic-acid-rich fractions had no effect on mitochondrial functions, whereas higher concentrations of caffeoylquinic-acid-rich fractions reduced the state 3 respiration rate (with the complex-I-dependent substrate glutamate/malate). (5) Both monocaffeoylquinic- and dicaffeoylquinic-acid-rich fractions possessed cytochrome-c-reducing properties; the greatest cytochrome c reduction properties were determined in the dicaffeoylquinic-acid-rich fraction purified from wormwood herb acetone extract. In summary, these findings show that caffeoylquinic acids might be beneficial as promising antioxidant and cytochrome-c-reducing agents for the modulation of mitochondria and treatment of various mitochondrial-pathway-associated pathologies.
咖啡酰奎宁酸是在菊科植物中发现的一些具有化学分类学意义的特殊代谢产物，具有广泛的生物活性。由于它们可能是潜在的线粒体靶向抗氧化剂，因此对有效的制备方法（包括从植物来源提取、分离和纯化咖啡酰奎宁酸）有很大需求。本研究的目的是从栽培艾草（L.）和银叶蒿（Nutt.）的草本丙酮提取物中分离咖啡酰奎宁酸，并评估它们的植物化学特征、抗氧化活性（自由基清除和还原活性）、对肾脏线粒体功能的影响以及细胞色素c还原特性。我们研究的主要发现如下：（1）从艾草和银叶蒿草本丙酮提取物中纯化的水相部分富含单咖啡酰奎宁酸（绿原酸、新绿原酸、4 - 咖啡酰奎宁酸），而从艾草和银叶蒿草本丙酮提取物中纯化的甲醇相部分富含二咖啡酰奎宁酸（4,5 - 二咖啡酰奎宁酸、3,4 - 二咖啡酰奎宁酸、3,5 - 二咖啡酰奎宁酸）。从艾草和银叶蒿草本丙酮提取物中纯化的水相部分仅由单咖啡酰奎宁酸组成。从艾草和银叶蒿草本丙酮提取物中纯化的甲醇相部分仅含有二咖啡酰奎宁酸。（2）从银叶蒿草本丙酮提取物中纯化的部分在咖啡酰奎宁酸含量方面最为突出。（3）在从银叶蒿草本丙酮提取物中纯化的富含二咖啡酰奎宁酸的部分中测定到最大的自由基清除活性；在从艾草草本丙酮提取物中纯化的富含二咖啡酰奎宁酸的部分中测定到最大的还原活性。（4）这两个部分对线粒体功能的影响呈剂量依赖性；较低浓度的富含咖啡酰奎宁酸的部分对线粒体功能没有影响，而较高浓度的富含咖啡酰奎宁酸的部分降低了状态3呼吸速率（使用依赖于复合体I的底物谷氨酸/苹果酸）。（5）富含单咖啡酰奎宁酸和二咖啡酰奎宁酸的部分都具有细胞色素c还原特性；在从艾草草本丙酮提取物中纯化的富含二咖啡酰奎宁酸的部分中测定到最大的细胞色素c还原特性。总之，这些发现表明咖啡酰奎宁酸作为有前景的抗氧化剂和细胞色素c还原剂，可能对调节线粒体和治疗各种与线粒体途径相关的疾病有益。
