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Integracide K: A New Tetracyclic Triterpenoid from Desmodium uncinatum (Jacq.) DC. (Fabaceae)
Borice Tapondjou Tsafack,Beaudelaire Kemvoufo Ponou,Rémy Bertrand Teponno,Raymond Ngansop Nono,Kristina Jenett-Siems,Matthias F. Melzig,박희준,Léon Azefack Tapondjou 한국생약학회 2017 Natural Product Sciences Vol.23 No.2
A new tetracyclic triterpenoid [4,4,24-trimethylcholesta-D8,9;14,15;24,28-trien-3b,11b,12a-triol-12-acetate, 3-sulfate] sodium salt (1), together with eight known compounds including ergosterol 5a,8a-endoperoxide (2), 1,9-dihydroxy-3-methoxy-2-methylpterocarpan (3), 3-O-b-D-2-acetyl-amino-2-deoxyglucopyranoxyloleanoic acid (4), hydnocarpin (5), derrone (6), isovitexin (7), erythrinin C (8), and 5,4'-dihydroxy-2''-hydroxyisopropyldihydrofurano [4,5:7,8]-isoflavone (9), were isolated from the EtOAc soluble fraction of the methanol extract of aerial part of Desmodium uncinatum collected in the western highland of Cameroon. The structures of these compounds were established by comprehensive interpretation of their spectral data mainly including 1D- (1H and 13C), 2D-NMR (1H-1H COSY, HMQC, HMBC) spectroscopic and ESI-TOF-MS mass spectrometric analysis. The isolation of an integracide-like compound from plant origin is a very unusual finding.
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.
Tapondjou, Leon Azefack,Ponou, Kemvoufo Beaudelaire,Teponno, Remy Bertrand,Mbiantcha, Marius,Djoukeng, Jules Desire,Nguelefack, Telesphore Benoit,Watcho, Pierre,Cadenas, Aurelio Gomez,Park, Hee-Juhn 대한약학회 2008 Archives of Pharmacal Research Vol.31 No.5
A new steroidal saponin, mannioside A (1), was isolated from the stem bark of Dracaena mannii, together with the known pennogenin (2), pennogenin-3-O-$\beta$-D-glucopyranoside (3) and pennogenin-3-O-$\alpha$-L-rhamnopyranosyl-($1{\rightarrow}2$)-[$\alpha$-L-rhamnopyranosyl-($1{\rightarrow}3$)]-$\beta$-D-glucopyranoside (4). Their structures were determined using 1D- and 2D-NMR spectroscopy and mass spectrometry. Compounds 1 and 3 significantly inhibited carrageenan-induced paw edema in the rat; compound 4 was moderately active whereas 2 showed very weak activity.
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.
Leon Azefack Tapondjou,Kemvoufo Beaudelaire Ponou,Remy Bertrand Teponno,Marius Mbiantcha,Jules Desire Djoukeng,Telesphore Benoit Nguelefack,Pierre Watcho,Aurelio Gomez Cadenas,박희준 대한약학회 2008 Archives of Pharmacal Research Vol.31 No.5
A new steroidal saponin, mannioside A (1), was isolated from the stem bark of Dracaena mannii, together with the known pennogenin (2), pennogenin-3-O-β-D-glucopyranoside (3) and pennogenin-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (4). Their structures were determined using 1D- and 2D-NMR spectroscopy and mass spectrometry. Compounds 1 and 3 significantly inhibited carrageenan-induced paw edema in the rat; compound 4 was moderately active whereas 2 showed very weak activity.
Quantitative Determination of the Triterpenoids and Total Tannin in Korean Rubus species by HPLC
김민영,Leon Azefack Tapondjou,박희준 한국생약학회 2014 Natural Product Sciences Vol.20 No.4
The triterpenoids contained in four Rubus species (Rosaceae) were quantitatively analyzed using HPLC to select plants with large quantities of niga-ichigoside F1. Unripe fruits, ripe fruits, and leaves were extracted to estimate the quantity of niga-ichigoside F1, together with Rubus-specific 19a-hydroxyursane-type triterpenoids, euscaphic acid, tormentic acid, and kaji-ichigoside F1, and a dimeric triterpenoid coreanoside F1. Niga-ichigoside F1 was most abundant in the leaves of R. crataegifolius (23.4 mg/g dry weight). The amount of triterpenoid in the black, ripe fruits of R. coreanus was lower than the unripe fruits of the same plant. On the other hand, the ripe fruits of three plants, R. crataegifolius, R. parvifolius and R. pungens var. oldhami, which are reddish, contained higher or similar level of triterpenoids than their unripe fruits. In addition, the concentration of niga-ichigoside F1 in the ripe fruit of R. crataegifolius was 20.5 mg/g, suggesting that the fruits could be used as a functional food. Methyl gallate and ellagic acid were used as quantitative indices of total tannin. Methyl gallate levels were higher in ripe fruits than unripe fruits in R. crataegifolius, R. pungens var. oldhami, and R. parvifolius. In R. crataegifolius, the quantity of methyl gallate was 30.5 mg/g in ripe fruit, but 1.19 mg/g in unripe fruit.
남정환,정현주,Leon Azefack Tapondjou,이경태,최종원,김원배,박희준 한국생약학회 2007 Natural Product Sciences Vol.13 No.2
demonstrate anti-hyperlipidemic activity of the 19α-hydroxyursane-type triterpenoid (19 -HUT)-rich fraction, this fraction was prepared from the extract of Rubus crataegifolius leaves. This fraction was found tohave anti-hyperlipidemic efect in a high fat diet-induced rat model from the observation of reduction ofabdominal fat pad weights, atherogenic index and hypercholesterolemia at 30 and 60 mg/kg (p.o.) The 19α-HUTfraction was subjected to SiO2, ODS, and/or Sephadex LH-20 column chromatography to yield a new triterpenoid(1) called pomolic acid ester along with nine known triterpenoids which are all 19α-HUTs: euscaphic acid (2),tormentic acid (3), 23-hydroxytormentic acid (4), kaji-ichigoside F1 (5), rosamultin (6), niga-ichigosides F1 (7)and F2 (8), suavisimoside F1 (9) and coreanoside F1 (10). The structure of compound 1 was established as 28-O-Compound 1 was isolated for the first time from natural sources.Key wordsRubus crataegifolius, Rosaceae, 19α-hydroxyursane-type triterpenoid, pomolic acid ester, NMR,anti-hyperlipidemic
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
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.
Télesphore Benoît Nguelefack,Félicité Hermine Kamga Mbakam,Léon Azéfack Tapondjou,Pierre Watcho,Elvine Pami Nguelefack-Mbuyo,Beaudelaire Kemvoufo Ponou,Albert Kamanyi,박희준 대한약학회 2011 Archives of Pharmacal Research Vol.34 No.4
The aerial part of Rubus rigidus var. camerunensis (Rosaceae) is used to treat respiratory and cardiovascular disorders in the Cameroonian traditional medicine. The ethanol extract exhibited more potent antioxidant activity (E_maxs of 119% and 229% activity on DPPH and β-carotene test) than aqueous extract. Bioactivity-guided fractionation of the ethanol extract based on free radical-scavenging assay (DPPH assay) afforded five flavonoid glycosides (four flavonol glycosides and an anthocyanin) and three glucosides of 19α-hydroxyursane-type triterpenoid (two monomeric and one dimeric triterpenoids). The flavonoids were identified as kaempferol 3-O-(2´´-O-E-p-coumaroyl)-β-D-glucopyranoside (1), kaempferol-3-O-β-D-glucopyranoside (astragalin, 2), kaempferol-3-O-α-L-arabinofuranoside (juglanin, 3), quercetin-3-O-β-D-glucopyranoside (isoquercitrin, 4), pelargonidin-3-O-β-D-glucopyranoside (callistephin, 5). The three triterpenoids were 2α, 3β, 19α, 23-tetrahydroxyurs-12-ene-28-O-β-D-glucopyranosyl ester (nigaichigoside F1, 6), 2α, 3β, 19α-trihydroxyurs-12-ene-23-carboxyl-28-O-β-D-glucopyranosyl ester (suavissimoside R_1, 7) as monomeric triterpenoids and coreanoside F_1 (8) as a dimeric triterpenoid. The flavonoids exhibited potent antioxidant activities (66 to 93.56% against DPPH radical) and they were also active on β-carotene test. Coreanoside F_1 exhibited a 63% antioxidant activity, meanwhile the other two triterpenoids showed a weak activity. Three important facts on structure-activity relationship were observed: Compound 8, a dimeric triterpenoid glycoside,strongly enhanced antioxidant activity of its monomers, compound 3 with 3-O-α-L-arabinofuranyl has much more potent activity than compound 2 with 3-O-β-D-glucopyranosyl, and antocyanin (5) is more potent than its corresponding flavonol glycosides.