Phenolic amides with anti-Parkinson’s disease (PD) effects from Nicandra physaloides
Nicandra physaloides is a traditional folk medicine in China, and its seeds are used to make jelly. Phytochemical investigation of the active ethyl acetate (EtOAc) extract of its fruits led to the isolation and identification of two new phenolic amides, (7R,8S)-7-(4-hydroxy-3,5-dimethoxyphenyl)-8-hy...
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| Format: | Article |
| Language: | English |
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Elsevier
2017-04-01
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| Series: | Journal of Functional Foods |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S1756464617300567 |
| _version_ | 1818596375529521152 |
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| author | Li-Qing Wang Ying Wang Su-Yu Gao Li-Han Zhu Fei Wang Hua Li Li-Xia Chen |
| author_facet | Li-Qing Wang Ying Wang Su-Yu Gao Li-Han Zhu Fei Wang Hua Li Li-Xia Chen |
| author_sort | Li-Qing Wang |
| collection | DOAJ |
| description | Nicandra physaloides is a traditional folk medicine in China, and its seeds are used to make jelly. Phytochemical investigation of the active ethyl acetate (EtOAc) extract of its fruits led to the isolation and identification of two new phenolic amides, (7R,8S)-7-(4-hydroxy-3,5-dimethoxyphenyl)-8-hydroxymethyl-1′-[N-7″-(4″-hydrxyphenyl)ethyl]carbamoylethenyl-3′-methoxybenzodihydrofuran (1) and cis-N-phydroxycinnamoyl-7′-methoxyethyltyramine (2), together with twelve known compounds (3–14). Their structures were determined on the basis of spectroscopic analyses. All these compounds are reported from the genus Nicandra for the first time. Compounds 1–14 were investigated for their protective effects on 1-methyl-4-phenylpyridiniumion (MPP+)-induced damage in human dopaminergic neuroblastoma cells (SH-SY5Y), and compounds 4, 6 and 7 showed significant protective activities at a certain concentration. Further, the cell protection mechanism of compound 4 was proved to be through inhibiting MPP+-induced apoptosis and inducing cytoprotective autophagy in Parkinson’s disease (PD). Herein, a plausible biosynthetic pathway of compounds 1–14 was also discussed. This study suggested that phenolic amides were potential candidate drugs for treating PD and the fruits of N. physaloides could be used as a functional food ingredient to improve the symptoms of memory loss, and possibly to prevent or treat PD. |
| first_indexed | 2024-12-16T11:30:55Z |
| format | Article |
| id | doaj.art-46dc8a42a9864abbb353d91c02df98d6 |
| institution | Directory Open Access Journal |
| issn | 1756-4646 |
| language | English |
| last_indexed | 2024-12-16T11:30:55Z |
| publishDate | 2017-04-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Journal of Functional Foods |
| spelling | doaj.art-46dc8a42a9864abbb353d91c02df98d62022-12-21T22:33:14ZengElsevierJournal of Functional Foods1756-46462017-04-0131229236Phenolic amides with anti-Parkinson’s disease (PD) effects from Nicandra physaloidesLi-Qing Wang0Ying Wang1Su-Yu Gao2Li-Han Zhu3Fei Wang4Hua Li5Li-Xia Chen6School of Traditional Chinese Materia Medica, Wuya College of Innovation, Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, ChinaSchool of Traditional Chinese Materia Medica, Wuya College of Innovation, Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, ChinaSchool of Traditional Chinese Materia Medica, Wuya College of Innovation, Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, ChinaSchool of Traditional Chinese Materia Medica, Wuya College of Innovation, Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, ChinaSchool of Traditional Chinese Materia Medica, Wuya College of Innovation, Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, ChinaSchool of Traditional Chinese Materia Medica, Wuya College of Innovation, Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China; School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China; Corresponding authors at: School of Traditional Chinese Materia Medica, Wuya College of Innovation, Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China (H. Li and L.X. Chen).School of Traditional Chinese Materia Medica, Wuya College of Innovation, Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China; Corresponding authors at: School of Traditional Chinese Materia Medica, Wuya College of Innovation, Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China (H. Li and L.X. Chen).Nicandra physaloides is a traditional folk medicine in China, and its seeds are used to make jelly. Phytochemical investigation of the active ethyl acetate (EtOAc) extract of its fruits led to the isolation and identification of two new phenolic amides, (7R,8S)-7-(4-hydroxy-3,5-dimethoxyphenyl)-8-hydroxymethyl-1′-[N-7″-(4″-hydrxyphenyl)ethyl]carbamoylethenyl-3′-methoxybenzodihydrofuran (1) and cis-N-phydroxycinnamoyl-7′-methoxyethyltyramine (2), together with twelve known compounds (3–14). Their structures were determined on the basis of spectroscopic analyses. All these compounds are reported from the genus Nicandra for the first time. Compounds 1–14 were investigated for their protective effects on 1-methyl-4-phenylpyridiniumion (MPP+)-induced damage in human dopaminergic neuroblastoma cells (SH-SY5Y), and compounds 4, 6 and 7 showed significant protective activities at a certain concentration. Further, the cell protection mechanism of compound 4 was proved to be through inhibiting MPP+-induced apoptosis and inducing cytoprotective autophagy in Parkinson’s disease (PD). Herein, a plausible biosynthetic pathway of compounds 1–14 was also discussed. This study suggested that phenolic amides were potential candidate drugs for treating PD and the fruits of N. physaloides could be used as a functional food ingredient to improve the symptoms of memory loss, and possibly to prevent or treat PD.http://www.sciencedirect.com/science/article/pii/S1756464617300567Nicandra physaloidesPhenolic amidesMPP+SH-SY5YPD |
| spellingShingle | Li-Qing Wang Ying Wang Su-Yu Gao Li-Han Zhu Fei Wang Hua Li Li-Xia Chen Phenolic amides with anti-Parkinson’s disease (PD) effects from Nicandra physaloides Journal of Functional Foods Nicandra physaloides Phenolic amides MPP+ SH-SY5Y PD |
| title | Phenolic amides with anti-Parkinson’s disease (PD) effects from Nicandra physaloides |
| title_full | Phenolic amides with anti-Parkinson’s disease (PD) effects from Nicandra physaloides |
| title_fullStr | Phenolic amides with anti-Parkinson’s disease (PD) effects from Nicandra physaloides |
| title_full_unstemmed | Phenolic amides with anti-Parkinson’s disease (PD) effects from Nicandra physaloides |
| title_short | Phenolic amides with anti-Parkinson’s disease (PD) effects from Nicandra physaloides |
| title_sort | phenolic amides with anti parkinson s disease pd effects from nicandra physaloides |
| topic | Nicandra physaloides Phenolic amides MPP+ SH-SY5Y PD |
| url | http://www.sciencedirect.com/science/article/pii/S1756464617300567 |
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