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Amaryllidaceae alkaloids with new framework types from Zephyranthes candida as potent acetylcholinesterase inhibitors
Zhan, GQ (Zhan, Guanqun)1; Liu, JJ (Liu, Junjun)1; Zhou, JF (Zhou, Junfei)1; Sun, B (Sun, Bin)1; Aisa, HA (Aisa, Haji Akber)1; Yao, GM (Yao, Guangmin)1
2017
Source PublicationEUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
ISSN0223-5234
Volume127Issue:2Pages:771-780
Abstract

Three new Amaryllidaceae alkaloids, named zephycandidines I-III (1-3), were isolated from Zephyranthes candida. The structures of 1-3 were elucidated by spectroscopic analyses including HRESIMS, H-1 NMR, C-13 NMR, DEPT, HSQC, H-1-H-1 COSY, HMBC, ROESY, and electronic circular dichroism (ECD), as well as ECD calculation. The absolute configuration of 1 was finally established by single crystal X-ray diffraction using Cu K alpha radiation. Zephycandidines I (1) and III (3) with new framework types represent the first example of 7-phenyl-hexahydroindole and 5,2'-dimethyl-biphenyl-2-ylamine alkaloids, respectively, and their plausible biosynthetic pathway are proposed. Zephycandidine 11 (2) is the first C3a-phenyl-hexahydroindole type alkaloid isolated from the genus of Zephyranthes. These new alkaloids 1-3 were evaluated for their acetylcholinesterase (AChE) inhibitory activities, and 3 showed potent AChE inhibitory activity with an IC50 value of 8.82 mu M, suggesting that the framework of 5,2'-dimethylbipheny1-2-ylamine in 3 may be a potential group for the AChE inhibitory activity. The docking studies of 1-3 and galanthamine with AChE revealed that interactions with W286 and Y337 are necessary for the AChE inhibitory activity.

KeywordAlzheimer's Disease Ache Inhibitory Activity Docking Studies Zephyranthes Candida Amaryllidaceae Alkaloids
DOI10.1016/j.ejmech.2016.10.057
Indexed BySCI
Language英语
WOS IDWOS:000397172800062
Citation statistics
Cited Times:8[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.xjipc.cas.cn/handle/365002/4993
Collection省部共建新疆特有药用资源利用重点实验室
资源化学研究室
Affiliation1.Huazhong Univ Sci & Technol, Sch Pharm, Tongji Med Coll, Hubei Key Lab Nat Med Chem & Resource Evaluat, Wuhan 430030, Peoples R China
2.Chinese Acad Sci, Xinjiang Tech Inst Phys & Chem, Key Lab Plant Resources & Chem Arid Zone, Urumqi 830011, Peoples R China
3.Chinese Acad Sci, Xinjiang Tech Inst Phys & Chem, State Key Lab Basis Xinjiang Indigenous Med Plant, Urumqi 830011, Peoples R China
Recommended Citation
GB/T 7714
Zhan, GQ ,Liu, JJ ,Zhou, JF ,et al. Amaryllidaceae alkaloids with new framework types from Zephyranthes candida as potent acetylcholinesterase inhibitors[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,2017,127(2):771-780.
APA Zhan, GQ ,Liu, JJ ,Zhou, JF ,Sun, B ,Aisa, HA ,&Yao, GM .(2017).Amaryllidaceae alkaloids with new framework types from Zephyranthes candida as potent acetylcholinesterase inhibitors.EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,127(2),771-780.
MLA Zhan, GQ ,et al."Amaryllidaceae alkaloids with new framework types from Zephyranthes candida as potent acetylcholinesterase inhibitors".EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY 127.2(2017):771-780.
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