Antimalarial constituents from Nauclea orientalis (L.) L

Zhen Dan He; Cui Ying Ma; Hongjie ZHANG; Ghee Teng Tan; Pamela Tamez; Kongmany Sydara; S. Bouamanivong; Bounhoong Southavong; Djaja D. Soejarto; John M. Pezzuto; Harry H.S. Fong

doi:10.1002/cbdv.200590110

Antimalarial constituents from Nauclea orientalis (L.) L

Zhen Dan He
, Cui Ying Ma
, Hongjie ZHANG
, Ghee Teng Tan
, Pamela Tamez
, Kongmany Sydara
, S. Bouamanivong
, Bounhoong Southavong
, Djaja D. Soejarto
, John M. Pezzuto
, Harry H.S. Fong^*

^*Corresponding author for this work

Research output: Contribution to journal › Review article › peer-review

48 Citations (Scopus)

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-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.

Original language	English
Pages (from-to)	1378-1386
Number of pages	9
Journal	Chemistry and Biodiversity
Volume	2
Issue number	10
DOIs	https://doi.org/10.1002/cbdv.200590110
Publication status	Published - Oct 2005

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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-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.",

author = "He, \{Zhen Dan\} and Ma, \{Cui Ying\} and Hongjie ZHANG and Tan, \{Ghee Teng\} and Pamela Tamez and Kongmany Sydara and S. Bouamanivong and Bounhoong Southavong and Soejarto, \{Djaja D.\} and Pezzuto, \{John M.\} and Fong, \{Harry H.S.\}",

year = "2005",

month = oct,

doi = "10.1002/cbdv.200590110",

language = "English",

volume = "2",

pages = "1378--1386",

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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.

PY - 2005/10

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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 - https://www.scopus.com/pages/publications/27844551215

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 -

Antimalarial constituents from Nauclea orientalis (L.) L

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