Olennikov Daniil N, Kashchenko Nina I, Chirikova Nadezhda K, Akobirshoeva Anzurat, Zilfikarov Ifrat N, Vennos Cecile
Institute of General and Experimental Biology, Siberian Division, Russian Academy of Science, Sakh'yanovoy Street 6, Ulan-Ude 670047, Russia.
Department of Biochemistry and Biotechnology, North-Eastern Federal University, 58 Belinsky Street, Yakutsk 677027, Russia.
Int J Mol Sci. 2017 Aug 2;18(8):1685. doi: 10.3390/ijms18081685.
Marigold ( L.) is one of the most common and widespread plants used medicinally all over the world. The present study aimed to evaluate the anti-acetylcholinesterase activity of marigold flowers, detect the compounds responsible and perform chemical analysis of marigold commercial products. Analysis of 23 varieties of flowers introduced into Siberia allowed us to select the Greenheart Orange variety due to the superior content of flavonoids (46.87 mg/g) and the highest inhibitory activity against acetylcholinesterase (IC 63.52 µg/mL). Flavonoids, isorhamnetin and quercetin derivatives were revealed as potential inhibitors with the application of high-performance liquid chromatography (HPLC) activity-based profiling. Investigation of the inhibitory activity of isorhamnetin glycosides demonstrated the maximal potency for isorhamnetin-3--(2'',6''-di-acetyl)-glucoside (IC 51.26 μM) and minimal potency for typhaneoside (isorhamnetin-3--(2'',6''-di-rhamnosyl)-glucoside; IC 94.92 µM). Among quercetin derivatives, the most active compound was quercetin-3--(2'',6''-di-acetyl)-glucoside (IC 36.47 µM), and the least active component was manghaslin (quercetin-3--(2'',6''-di-rhamnosyl)-glucoside; IC 94.92 µM). Some structure-activity relationships were discussed. Analysis of commercial marigold formulations revealed a reduced flavonoid content (from 7.18-19.85 mg/g) compared with introduced varieties. Liquid extract was the most enriched preparation, characterized by 3.10 mg/mL of total flavonoid content, and infusion was the least enriched formulation (0.41 mg/mL). The presented results suggest that isorhamnetin and quercetin and its glycosides can be considered as potential anti-acetylcholinesterase agents.
金盏花（万寿菊属）是世界上最常见且分布广泛的药用植物之一。本研究旨在评估金盏花的抗乙酰胆碱酯酶活性，检测其活性成分，并对金盏花商业产品进行化学分析。对引入西伯利亚的23个金盏花品种进行分析后，我们选择了“绿心橙”品种，因其黄酮类化合物含量较高（46.87毫克/克）且对乙酰胆碱酯酶的抑制活性最强（IC50为63.52微克/毫升）。通过基于高效液相色谱（HPLC）活性图谱分析，发现黄酮类化合物、异鼠李素和槲皮素衍生物是潜在的抑制剂。对异鼠李素糖苷抑制活性的研究表明，异鼠李素-3-O-(2'',6''-二乙酰基)-葡萄糖苷的活性最强（IC50为51.26微摩尔），而异鼠李素-3-O-(2'',6''-二鼠李糖基)-葡萄糖苷（异鼠李素苷）的活性最弱（IC50为94.92微摩尔）。在槲皮素衍生物中，活性最强的化合物是槲皮素-3-O-(2'',6''-二乙酰基)-葡萄糖苷（IC50为36.47微摩尔），活性最弱的成分是芒果苷（槲皮素-3-O-(2'',6''-二鼠李糖基)-葡萄糖苷；IC50为94.92微摩尔）。讨论了一些构效关系。对市售金盏花制剂的分析表明，与引入品种相比，其黄酮类化合物含量有所降低（从7.18 - 19.85毫克/克）。液体提取物是含量最丰富的制剂，总黄酮含量为3.10毫克/毫升，而浸剂是含量最少的制剂（0.41毫克/毫升）。研究结果表明，异鼠李素、槲皮素及其糖苷可被视为潜在的抗乙酰胆碱酯酶药物。
