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Planta Med 2003; 69(2): 148-152
DOI: 10.1055/s-2003-37710
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag Stuttgart · New York

Two New Protopines Argemexicaines A and B and the Anti-HIV Alkaloid 6-Acetonyldihydrochelerythrine from Formosan Argemone mexicana

Yuh-Chwen Chang1 , 2 , Pei-Wen Hsieh2 , Fang-Rong Chang2 , Ru-Rong Wu3 , Chih-Chuang Liaw2 , 4 , Kuo-Hsiung Lee4 , Yang-Chang Wu2
  • 1Department of Chemical Engineering, Kao Yuan Institute of Technology, Kaohsiung, Taiwan, R.O.C.
  • 2Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung, Taiwan, R.O.C.
  • 3Tainan Regional Instrument Center, Cheng Kung University, Tainan, Taiwan, R.O.C.
  • 4Natural Products Laboratory, School of Pharmacy, University of North Carolina at Chapel Hill, NC, USA
Further Information

Publication History

Received: May 31, 2002

Accepted: October 3, 2002

Publication Date:
07 March 2003 (online)

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Abstract

Two new protopine-type alkaloids, argemexicaine A (1) and argemexicaine B (2), along with thirteen known alkaloids, were isolated from MeOH extracts of Formosan Argemone mexicana L. (Papaveraceae). Physical and spectral analyses, particularly IR and thermo-modulated 1D and 2D NMR, were used to determine the transannular conformations of the isolated protopine-type alkaloids. The known benzo[c]phenanthridine (±)-6-acetonyldihydrochelerythrine (5) exhibited significant anti-HIV activity in H9 lymphocytes with EC50 and TI (Therapeutic Index) values of 1.77 μg/mL and 14.6, respectively.

Key words

Argemone mexicana - Papaveraceae - argemexicaine A - argemexicaine B - protopine - benzo[c]phenanthridine - (±)-6-acetonyldihydrochelerythrine - anti-HIV activity

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Prof. Dr. Yang-Chang Wu

Graduate Institute of Natural Products

Kaohsiung Medical University

Kaohsiung 807

Taiwan

Republic of China

Email: yachwu@kmu.edu.tw

Fax: +886-7-3114773