Lycodine-type alkaloids from Lycopodiastrum casuarinoides and their acetylcholinesterase inhibitory activity

被引:8
|
作者
Feng, Zheling [1 ]
Chen, Shixin [2 ]
Wang, Wei [3 ]
Feng, Lu [4 ,5 ]
Dong, Yanyan [6 ]
Zou, Yiping [6 ]
Ke, Changqiang [4 ,5 ]
Tang, Chunping [4 ,5 ]
Yao, Sheng [4 ,5 ]
Zhang, Haiyan [3 ]
Gan, Lishe [2 ]
Ye, Yang [4 ,5 ,7 ]
Lin, Ligen [1 ]
机构
[1] Univ Macau, Inst Chinese Med Sci, State Key Lab Qual Res Chinese Med, Taipa 999078, Macao, Peoples R China
[2] Zhejiang Univ, Coll Pharmaceut Sci, Hangzhou 310007, Zhejiang, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Mat Med, CAS Key Lab Receptor Res, Shanghai 201203, Peoples R China
[4] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Long Res, Shanghai 201203, Peoples R China
[5] Chinese Acad Sci, Shanghai Inst Mat Med, Nat Prod Chem Dept, Shanghai 201203, Peoples R China
[6] Yichun Univ, Coll Chem & Bioengn, Yichun 336000, Jiangxi, Peoples R China
[7] Shanghai Tech Univ, Sch Life Sci & Technol, Shanghai 201210, Peoples R China
基金
中国国家自然科学基金;
关键词
Lycopodiastrum casuarinoides; Lycopodiaceae; Lycodine-type alkaloids; TD-DFT; ECD; ALZHEIMERS-DISEASE; HUPERZINE;
D O I
10.1016/j.fitote.2019.104378
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Five previously undescribed lycodine-type alkaloids, named huperzine Y (1), 8,15-epoxy-N-demethylhuperzinine (2), 7-hydroxyl-huperzinine (3), huperzine Z (4), and huperzine D N-oxide (5), were isolated from the aerial parts and roots of Lycopodiastrum casuarinoides (Lycopodiaceae), along with ten known analogues. The structures of the new compounds were elucidated by means of spectroscopic technique (IR, UV, MS and NMR). The absolute configurations of the new compounds were established on the basis of comparison of their experimental and TD-DFT (time-dependent density functional theory) calculated ECD spectra. Moreover, all the isolates were evaluated for acetylcholinesterase (AChE) inhibitory activity. Only huperzine C showed moderate activity, with an IC50 value of 0.525 +/- 0.140 mu M, which was comparable with the positive control, huperzine A (IC50 = 0.143 +/- 0.029 mu M).
引用
收藏
页数:7
相关论文
共 50 条
  • [21] Mass spectrometry studies of lycodine-type Lycopodium alkaloids: sauroxine and N-demethylsauroxine
    Cifuente, Diego A.
    Vallejo, Mariana G.
    Ortega, Maria G.
    Cabrera, Jose L.
    Martin, Victor S.
    Tonn, Carlos E.
    Agnese, Alicia M.
    Ardanaz, Carlos E.
    RAPID COMMUNICATIONS IN MASS SPECTROMETRY, 2014, 28 (24) : 2690 - 2694
  • [22] THE ALKALOIDS HUPERZINE-C AND HUPERZINE-D AND HUPERZININE FROM LYCOPODIASTRUM CASUARINOIDES
    LIU, JS
    HUANG, MF
    PHYTOCHEMISTRY, 1994, 37 (06) : 1759 - 1761
  • [23] Lycocasine A, a Lycopodium Alkaloid from Lycopodiastrum casuarinoides and Its Acid-Sensing Ion Channel 1a Inhibitory Activity
    Jiang, Shuai
    Li, Wen-Yan
    Gao, Bei-Bei
    Zhao, Qin-Shi
    MOLECULES, 2024, 29 (07):
  • [24] Triterpenoidal Alkaloids from Buxus natalensis and Their Acetylcholinesterase Inhibitory Activity
    Matochko, Wadim L.
    James, Abin
    Lam, Cheuk W.
    Kozera, Daniel J.
    Ata, Athar
    Gengan, Robert M.
    JOURNAL OF NATURAL PRODUCTS, 2010, 73 (11): : 1858 - 1862
  • [25] Aporphine alkaloids from Piper erecticaule and acetylcholinesterase inhibitory activity
    Salleh, Wan Mohd Nuzul Hakimi Wan
    Abdullah, Norkamilah
    Hashim, Nur Athirah
    Khong, Heng Yen
    Khamis, Shamsul
    BOLETIN LATINOAMERICANO Y DEL CARIBE DE PLANTAS MEDICINALES Y AROMATICAS, 2019, 18 (05): : 527 - 532
  • [26] Acetylcholinesterase Inhibitory Activity of Alkaloids Isolated from Stephania venosa
    Kongkiatpaiboon, Sumet
    Duangdee, Nongnaphat
    Prateeptongkum, Saisuree
    Chaijaroenkul, Wanna
    NATURAL PRODUCT COMMUNICATIONS, 2016, 11 (12) : 1805 - 1806
  • [27] Lycoparins A-C, new alkaloids from Lycopodium casuarinoides inhibiting acetylcholinesterase
    Hirasawa, Yusuke
    Kato, Eri
    Kobayashi, Jun'ichi
    Kawahara, Nobuo
    Goda, Yukihiro
    Shiro, Motoo
    Morita, Hiroshi
    BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (11) : 6167 - 6171
  • [28] Alkaloids from two Nigerian Crinum species and their acetylcholinesterase inhibitory activity
    Houghton, P. J.
    Adegbulugbe, A.
    Agbedahunsi, J.
    JOURNAL OF PHARMACY AND PHARMACOLOGY, 2004, 56 : S77 - S78
  • [29] Amaryllidaceae alkaloids from the Australasian tribe Calostemmateae with acetylcholinesterase inhibitory activity
    Jensen, Bent Sovso
    Christensen, Soren Brogger
    Jager, Anna Katharina
    Ronsted, Nina
    BIOCHEMICAL SYSTEMATICS AND ECOLOGY, 2011, 39 (02) : 153 - 155
  • [30] Proaporphine and aporphine alkaloids with acetylcholinesterase inhibitory activity from Stephania epigaea
    Dong, Jian-Wei
    Cai, Le
    Fang, Yun-Shan
    Xiao, Huai
    Li, Zhen-Jie
    Ding, Zhong-Tao
    FITOTERAPIA, 2015, 104 : 102 - 107