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Planta Med 2014; 80(13): 1124-1130
DOI: 10.1055/s-0034-1382961
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Amide Alkaloids from Scopolia tangutica

Zhen Long   *
1   Key Laboratory of Separation Science for Analytical Chemistry, Key Lab of Natural Medicine, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Peopleʼs Republic of China
,
Yan Zhang   *
2   Department of Pharmacology, University of California, Irvine, California, United States
,
Zhimou Guo
1   Key Laboratory of Separation Science for Analytical Chemistry, Key Lab of Natural Medicine, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Peopleʼs Republic of China
,
Lien Wang
2   Department of Pharmacology, University of California, Irvine, California, United States
,
Xingya Xue
1   Key Laboratory of Separation Science for Analytical Chemistry, Key Lab of Natural Medicine, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Peopleʼs Republic of China
,
Xiuli Zhang
1   Key Laboratory of Separation Science for Analytical Chemistry, Key Lab of Natural Medicine, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Peopleʼs Republic of China
,
Shisheng Wang
3   School of Pharmaceutical Science and Technology, Dalian University of Technology, Dalian, Peopleʼs Republic of China
,
Zhiwei Wang
2   Department of Pharmacology, University of California, Irvine, California, United States
,
Olivier Civelli
2   Department of Pharmacology, University of California, Irvine, California, United States
,
Xinmiao Liang
1   Key Laboratory of Separation Science for Analytical Chemistry, Key Lab of Natural Medicine, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Peopleʼs Republic of China
› Author Affiliations
Further Information

Publication History

received 22 February 2014
revised 03 July 2014

accepted 09 July 2014

Publication Date:
15 August 2014 (online)

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Abstract

Four new hydroxycinnamic acid amides, scotanamines A–D (1–4), and seven known alkaloids, including N 1,N 10-di-dihydrocaffeoylspermidine (5), scopolamine (6), anisodamine (7), hyoscyamine (8), anisodine (9), caffeoylputrescine (10), and N 1-caffeoyl-N 3-dihydrocaffeoylspermidine (11), were obtained from the roots of Scopolia tangutica. The present study represents the first recognition of hydroxycinnamic acid amides containing putrescine or spermidine in S. tangutica. Compound 1, in particular, contains a moiety resulting from the condensation of nortropinone and putrescine. Compound 2 exhibited moderate agonist activity at the µ-opioid receptor (EC50 = 7.3 µM). Compound 2 was tested in vivo and induced analgesia in mice. The analgesic effect was recorded using the tail-flick assay and was reversed by naloxone.

Key words

Scopolia tangutica - Solanaceae - alkaloid - hydroxycinnamic acid amide - µ-opioid receptor

* These authors contributed equally to this work.


Supporting Information

 

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