title: Antimalarial constituents from Nauclea orientalis (L.) L.
abstract: 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-beta-carboline monoterpene alkaloid glucosides, naucleaorine (= (16alpha,17beta)-3,14:15,20-tetradehydro-16-ethenyl-17-(beta-D-glucopyranosyloxy)-19alpha-methoxyoxayohimban-21-one; 1) and epimethoxynaucleaorine (2), as well as the known compounds, strictosidine lactam (= (15beta,16alpha,17beta)-19,20-didehydro-16-ethenyl-17-(beta-D-glucopyranosyloxy)oxayohimban-21-one; 3), 3,4,5-trimethoxyphenol (4), 3alpha-hydroxyurs-12-en-28-oic acid methyl ester (5), 3alpha,23-dihydroxyurs-12-en-28-oic acid (6), 3alpha,19alpha,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 spectroscopic methods including 1D- and 2D-NMR analyses.
authors.affiliation: Program for Collaborative Research in Pharmaceutical Sciences, M/C 781, Department of Medicinal Chemistry & Pharmacognosy, College of Pharmacy, the University of Illinois at Chicago, 833 S. Wood Street, Chicago, Illinois 60612, USA.
authors.forename: Zhen-Dan
authors.initials: ZD
authors.lastname: He
authors.forename: Cui-Ying
authors.initials: CY
authors.lastname: Ma
authors.forename: Hong-Jie
authors.initials: HJ
authors.lastname: Zhang
authors.forename: Ghee Teng
authors.initials: GT
authors.lastname: Tan
authors.forename: Pamela
authors.initials: P
authors.lastname: Tamez
authors.forename: Kongmany
authors.initials: K
authors.lastname: Sydara
authors.forename: S
authors.initials: S
authors.lastname: Bouamanivong
authors.forename: Bounhoong
authors.initials: B
authors.lastname: Southavong
authors.forename: Djaja D
authors.initials: DD
authors.lastname: Soejarto
authors.forename: John M
authors.initials: JM
authors.lastname: Pezzuto
authors.forename: Harry H S
authors.initials: HH
authors.lastname: Fong
mesh_terms: D000818:Animals; D000962:Antimalarials / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D015394:Molecular Structure; D010963:Plasmodium falciparum / Q000187:drug effects; D019666:Rubiaceae / Q000737:chemistry*
chemical_list: D000962:Antimalarials