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Antimalarial Constituents from Nauclea orientalis (L.) L.
Author(s) -
He ZhenDan,
Ma CuiYing,
Zhang HongJie,
Tan Ghee Teng,
Tamez Pamela,
Sydara Kongmany,
Bouamanivong S.,
Southavong Bounhoong,
Soejarto Djaja D.,
Pezzuto John M.,
Fong Harry H. S.
Publication year - 2005
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200590110
Subject(s) - chemistry , plasmodium falciparum , monoterpene , oleanolic acid , stereochemistry , rubiaceae , alkaloid , terpene , bioassay , organic chemistry , botany , malaria , biology , medicine , alternative medicine , genetics , pathology , immunology
Bioassay‐guided fractionation of the antimalarial‐active CHCl 3 extract of the dried stem of Nauclea orientalis (L.) L. (Rubiaceae) has resulted in the isolation of two novel tetrahydro‐ β ‐carboline monoterpene alkaloid glucosides, naucleaorine (=(16 α ,17 β )‐3,14:15,20‐tetradehydro‐16‐ethenyl‐17‐( β ‐ D ‐glucopyranosyloxy)‐19 α ‐methoxyoxayohimban‐21‐one; 1 ) and epimethoxynaucleaorine ( 2 ), as well as the known compounds, strictosidine lactam (=(15 β ,16 α ,17 β )‐19,20‐didehydro‐16‐ethenyl‐17‐( β ‐ D ‐glucopyranosyloxy)oxayohimban‐21‐one; 3 ), 3,4,5‐trimethoxyphenol ( 4 ), 3 α ‐hydroxyurs‐12‐en‐28‐oic acid methyl ester ( 5 ), 3 α ,23‐dihydroxyurs‐12‐en‐28‐oic acid ( 6 ), 3 α ,19 α ,23‐trihydroxyurs‐12‐en‐28‐oic acid methyl ester ( 7 ), and oleanolic acid ( 8 ). Compounds 1, 2, 6 , and 8 showed moderate in vitro activities against Plasmodium falciparum. Their structures and configurations were elucidated by spectrocopic methods including 1D‐ and 2D‐NMR analyses.