[논문]Potent inhibitions of monoamine oxidase A and B by acacetin and its 7-O-(6-O-malonylglucoside) derivative from Agastache rugosa

Lee, Hyun Woo; Ryu, Hyung Won; Baek, Seung Cheol; Kang, Myung-Gyun; Park, Daeui; Han, Hyoung-Yun; An, Ju Hyeon; Oh, Sei-Ryang; Kim, Hoon

doi:10.1016/j.ijbiomac.2017.06.076

Potent inhibitions of monoamine oxidase A and B by acacetin and its 7-O-(6-O-malonylglucoside) derivative from Agastache rugosa

International journal of biological macromolecules, v.104 pt.A, 2017년, pp.547 - 553

Lee, Hyun Woo (Department of Pharmacy and Research Institute of Life Pharmaceutical Sciences, Sunchon National University, Suncheon 57922, Republic of Korea) , Ryu, Hyung Won (Natural Medicine Research Center, Korea Research Institute of Bioscience and Biotechnology, 30 Yeongudanji-ro, Ochang-eup, Cheongju, Chungbuk 28116, Republic of Korea) , Baek, Seung Cheol (Department of Pharmacy and Research Institute of Life Pharmaceutical Sciences, Sunchon National University, Suncheon 57922, Republic of Korea) , Kang, Myung-Gyun (Department of Predictive Toxicology, Korea Institute of Toxicology, Daejeon 34114, Republic of Korea) , Park, Daeui (Department of Predictive Toxicology, Korea Institute of Toxicology, Daejeon 34114, Republic of Korea) , Han, Hyoung-Yun (Department of Predictive Toxicology, Korea Institute of Toxicology, Daejeon 34114, Republic of Korea) , An, Ju Hyeon (Natural Medicine Research Center, Korea Research Institute of Bioscience and Biotechnology, 30 Yeongudanji-ro, Ochang-eup, Cheongju, Chungbuk 28116, Republic of Korea) , Oh, Sei-Ryang (Natural Medicine Research Center, Korea Research Institute of Bio) , Kim, Hoon

Abstract ▼ AI-Helper

Five compounds were isolated from the leaves of Agastache rugosa and tested for monoamine oxidase (MAO) inhibitory activity. Acacetin, a flavonoid, potently inhibited recombinant human MAO-A and MAO-B (IC50=0.19 and 0.17 mu M, respectively), and reversibly and competitively inhibited MAO-A and MAO-B (K-i;=0.045 and 0.037 mu M, respectively). Acacetin 7-0-(6-O-malonylglucoside) (AMG) was also found to effectively inhibit MAO-A and MAO-B (IC50=2.34 and 1.87 mu M, respectively), and to reversibly and competitively inhibit MAO-A and MAO-B (K-i=1.06 and 0.38 mu M, respectively). Tilianin (a glucoside derivative of acacetin) had little inhibitory activity, but the introduction of a malonyl group at sugar moiety significantly increased inhibitory activity. Molecular docking simulation revealed the binding energy of acacetin for MAO-B (-44.2 kcal/mol) was greater than its energy for MAO-A (-27.0 kcal/mol), and that the Cys172 residue of MAO-B was important for hydrogen bonding with acacetin. AMG was predicted to bind to MAO-B with an energy of 23.1 kcal/mol by possible hydrogen-bond formation between an oxygen, atom of Ile477 residue and a hydrogen atom (H17) of AMG. However, the interaction between AMG and MAO-A was not verified by the docking simulation. This study suggests acacetin and AMG be viewed as new reversible MAO inhibitors, and useful lead compounds for the inhibitor development. (C) 2017 Elsevier B.V. All rights reserved.

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Potent inhibitions of monoamine oxidase A and B by acacetin and its 7-O-(6-O-malonylglucoside) derivative from Agastache rugosa

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Potent inhibitions of monoamine oxidase A and B by acacetin and its 7-O-(6-O-malonylglucoside) derivative from Agastache rugosa

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