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Novel Alkaloids from Myrioneuron nutans
Author(s) -
Pham Van Cuong,
Jossang Akino,
Sévenet Thierry,
Nguyen Van Hung,
Bodo Bernard
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200801028
Subject(s) - formylation , chemistry , cytotoxicity , absolute configuration , stereochemistry , mass spectrometry , plasmodium falciparum , optical rotation , specific rotation , nuclear magnetic resonance spectroscopy , alkaloid , organic chemistry , chromatography , in vitro , biochemistry , malaria , immunology , biology , catalysis
Two new alkaloids, dehydronitraramine ( 1 ) and N ‐formylmyrionine ( 2 ) were isolated from the leaves of Myrioneuron nutans , and their structures were determined from spectroscopic analysis, including mass spectrometry and 2D‐NMR spectroscopy. The absolute configuration 8 S , 9 R , 10 S of N ‐formylmyrionine ( 2 ) was established by N ‐formylation of the known (8 S ,9 R ,10 S )‐myrionine and then comparison of the optical rotation of the natural N ‐formylmyrionine ( 2 ) with that of the semi‐synthetic (8 S ,9 R ,10 S )‐ N ‐formylmyrionine. Dehydronitraramine ( 1 ) displayed a moderate antiplasmodial activity against Plasmodium falciparum with an IC 50 value of 16 μ M , whereas both 1 and 2 showed a weak cytotoxicity against KB cells.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)