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Structure-Activity Relationship of Triterpenoids Isolated from Mitragyna stipulosa on Cytotoxicity
Tapondjou, Leon Azefack,Lontsi, David,Sondengam, Beiham Luc,Choudhary, Muhammad Iqbal,Park, Hee-Juhn,Choi, Jong-Won,Lee, Kyung-Tae The Pharmaceutical Society of Korea 2002 Archives of Pharmacal Research Vol.25 No.3
Chromatographic separation of the stem bark extract of Mitragyna stipulosa afforded triterpene derivatives ursolic acid (1), quinovic acid (2), quinivic acid $3-O-{\beta}-D-glucopyranoside$ (3, quinovin glycoside C), quinovic acid 3-O-[$(2-O-sulfo)-{\beta}-D-quinovopyranoside$] (4, zygophyloside D) and quinovic acid $3-O-{\beta}-D-quinovopyranosyl-27-O-{\beta}-D-glucopyranosyl$ ester (5, zygophyloside B). These five compounds were subjected to the cytotoxicity on MTT assay system. Compound 1 among tested showed the most potent cytotoxicity. Quinovic acid showed less potent cytotoxicity than ursolic acid and sugar linkages to 2 decreased the cytotoxicity. Compound 4 more potent than 3 with indicate that the sulfonyl group significantly enhances the activity. This indicates that the glycosidic linkage in ursane-type triterpenoids has mainly negative effect on cytotoxicity unlike in oleanane-type glycosides.
Tapondjou, L.A.,Lontsi, David,Sondengam, Beiban-Luc,Choi, Jong-Won,Lee, Kyung-Tae,Jung, Hyun-Ju,Park, Hee-Juhn The Pharmaceutical Society of Korea 2003 Archives of Pharmacal Research Vol.26 No.2
Triterpenoids, ursolic acid (1) and 23-hydroxyursolic acid (2) were obtained from the hydrolysis of BuOH fraction of Cussonia bancoensis extract to test anti nociceptive and anti-inflammatory effect of C. bancoensis (Araliaceae). Compound 1 and 2 exhibited anti-nociceptive effects, which were determined by acetic acid-induced writhing test and hot plate test. The effect of 2 was much more potent in acetic acid-induced writhing test than in hot plate test. Compound 1 and 2 significantly inhibited 1%-carrageenan-induced edema in the rat. These results suggest that the two triterpenes, ursolic acid and 23-hydroxyursolic acid, are responsible for the antinociceptive and anti-inflammatory effect of C. bancoesnsis.
Shin, Kyung-Min,Kim, Rung-Kyu,Azefack, Tapondjou Leon,David, Lontsi,Luc, Sondengam, Beibam,Choudhary, Muhammad, Iqbal,Park, Hee-Juhn,Choi, Jong-Won,Lee, Kyung-Tae WHO COLLABORATING CENTRE FOR TRADITIONAL MEDICINE 2004 東西醫學硏究所 論文集 Vol.2004 No.-
In the present study, the effects of various triterpenoids isolated from the stem bark of Cussonia bancoensis, namely, ursolic acid (1), 23-hydroxyursolic acid (2), 3-O-α-L-arabinopyranosyl-23-hydroxyursolic acid (3), and 3-O-ß-D-glucopyranosyl-23-hydroxyursolic acid (4) were evaluated an lipopolysaccharide (LPS)-induced nitric oxide (NO) and prostaglandin E₂ (PGE₂) release by the macrophage cell line RAW 264.7. Of the tested triterpenoids, 23-hydroxyursolic acid (2) was found to be the most potent inhibitor of NO production, and also significantly reduced PGE₂ release. Consistent with these observations, the protein and mRNA expression levels of inducible NO synthase (iNOS) and cyclooxygenase (COX)-2 enzymes were inhibited by 23-hydroxyursolic acid (2) in a concentration-dependent manner. Furthermore, 23-hydroxyursolic acid (2) inhibited the LPS-induced DNA binding activity of nuclear factor-кB (NF-кB), which was associated with a decrease of p65 protein levels in the nucleus. These results suggest that the 23-hydroxyursolic acid-mediated inhibition of iNOS and COX-2 expression, via blocking NF-кB activation, may mechanistically responsible for the anti-inflammatory effects of Cussonia bancoensis stem bark in vitro.
Isolation and NMR Assignment of a Pennogenin Glycoside from Dioscorea bulbifera L. var sativa
Remy Bertrand Teponno,Azefack Leon Tapondjou,Jules Desire Djoukeng,Eliane Abou-Mansour,Raphael Tabacci,Pierre Tane,David Lontsi,Hee-Juhn Park 한국생약학회 2006 Natural Product Sciences Vol.12 No.1
steroidal saponin, 3-O-α-L-rhamnopyranosyl-(1. 2)-[α-L-rhamnopyranosyl-(1. 3)]-β-D-glucop-yranosylpennogenin (1, spiroconazole A) was isolated from the tubers of Dioscorea bulbifera L. var sativa and1H-and 13C-NMR assignment was completed using HMBC corelation. In addition, four phenolic substances, 2,7-dihydroxy-4-methoxyphenanthrene (2), quercetin (3), quercetin-3-O-β-D-glucopyranoside (4), and quercetin-3-O-β-D-galactopyranoside (5) were also isolated. KeywordsDioscorea bulbifera L. var sativa, steroidal saponin, phenanthrene, flavonoid, HMBC