TY - JOUR
T1 - Antimalarial constituents from Nauclea orientalis (L.) L
AU - He, Zhen Dan
AU - Ma, Cui Ying
AU - ZHANG, Hongjie
AU - Tan, Ghee Teng
AU - Tamez, Pamela
AU - Sydara, Kongmany
AU - Bouamanivong, S.
AU - Southavong, Bounhoong
AU - Soejarto, Djaja D.
AU - Pezzuto, John M.
AU - Fong, Harry H.S.
N1 - Copyright:
Copyright 2011 Elsevier B.V., All rights reserved.
PY - 2005
Y1 - 2005
N2 - Bioassay-guided fractionation of the antimalarial-active CHCl3 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 (=(16α,17β)-3,14:15,20-tetradehydro- 16-ethenyl-17-(β-D-glucopyranosyloxy)- 19α-methoxyoxayohimban-21-one; 1) and epimethoxynaucleaorine (2), as well as the known compounds, strictosidine lactam (=(15β,16α,17β)-19,20-didehydro-16- ethenyl-17-(β-D-glucopyranosyloxy)oxayohimban-21-one; 3), 3,4,5-trimethoxyphenol (4), 3α-hydroxyurs-12-en-28-oic acid methyl ester (5), 3α,23-dihydroxyurs-12-en-28-oic acid (6), 3α,19α,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.
AB - Bioassay-guided fractionation of the antimalarial-active CHCl3 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 (=(16α,17β)-3,14:15,20-tetradehydro- 16-ethenyl-17-(β-D-glucopyranosyloxy)- 19α-methoxyoxayohimban-21-one; 1) and epimethoxynaucleaorine (2), as well as the known compounds, strictosidine lactam (=(15β,16α,17β)-19,20-didehydro-16- ethenyl-17-(β-D-glucopyranosyloxy)oxayohimban-21-one; 3), 3,4,5-trimethoxyphenol (4), 3α-hydroxyurs-12-en-28-oic acid methyl ester (5), 3α,23-dihydroxyurs-12-en-28-oic acid (6), 3α,19α,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.
UR - http://www.scopus.com/inward/record.url?scp=27844551215&partnerID=8YFLogxK
U2 - 10.1002/cbdv.200590110
DO - 10.1002/cbdv.200590110
M3 - Review article
C2 - 17191939
AN - SCOPUS:27844551215
SN - 1612-1872
VL - 2
SP - 1378
EP - 1386
JO - Chemistry and Biodiversity
JF - Chemistry and Biodiversity
IS - 10
ER -