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Planta Med 2016; 82(11/12): 1046-1050
DOI: 10.1055/s-0042-106904
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Squarrosine A and Pyrrolhuperzine A, New Lycopodium Alkaloids from Thai and Philippine Huperzia squarrosa [*]

Thanasan Nilsu
1   Applied Biological Sciences Program, Chulabhorn Graduate Institute, Bangkok, Thailand
,
Sakornrat Thorroad
2   Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, Bangkok, Thailand
,
Somsak Ruchirawat
2   Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, Bangkok, Thailand
3   Chemical Biology Program, Chulabhorn Graduate Institute, Bangkok, Thailand
4   The Center of Excellence on Environmental Health and Toxicology (EHT), Commission on Higher Education, Ministry of Education, Bangkok, Thailand
,
Nopporn Thasana
2   Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, Bangkok, Thailand
3   Chemical Biology Program, Chulabhorn Graduate Institute, Bangkok, Thailand
4   The Center of Excellence on Environmental Health and Toxicology (EHT), Commission on Higher Education, Ministry of Education, Bangkok, Thailand
› Author Affiliations
Further Information

Publication History

received 28 February 2016
revised 09 April 2016

accepted 11 April 2016

Publication Date:
18 May 2016 (online)

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Abstract

Two new Lycopodium alkaloids, squarrosine A (1) and pyrrolhuperzine A (2), were isolated from the Thai and Philippine plant Huperzia squarrosa. (R)-2-Piperidineacetic acid (5) was a known alkaloid, but has now been isolated for the first time from a natural source. Their structures were elucidated using extensive spectroscopic analyses and, for pyrrolhuperzine A (2), confirmation by chemical transformation. The new compounds exhibited moderate acetylcholinesterase inhibitory activities.

Key words

Huperzia squarrosa - Lycopodiaceae - Lycopodium alkaloid - Huperzine A derivative - Acetylcholinesterase inhibitor

* Dedicated to Professor Dr. Dr. h. c. mult. Kurt Hostettmann in recognition of his outstanding contribution to natural product research.


Supporting Information

 

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