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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.
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.
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.
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
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
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.
Laurentine Bouquet Tankeu Nyaa,Luciano Barboni,Pierre Tane,Hee-Juhn Park,Léon Azefack Tapondjou,Jean De Dieu Tamokou,Jules Roger Kuiaté 한국생약학회 2009 Natural Product Sciences Vol.15 No.2
Phytochemical investigation of the EtOAc and n-BuOH fractions obtained from the crude methanol extract of the seeds of Butyrospermum parkii led to the isolation of seven compounds including 1β,2α,3α- trihydroxyurs-12-en-28-oic acid (1β-hydroxyeuscaphic acid) which full NMR assignment is herein reported for the first time. The above extract, fractions and some of the isolated compounds were screened for antimicrobial and antioxidant activities; 1β-hydroxyeuscaphic acid was the more potent.
Steroidal Saponins from Dracaena humilis (Dracaenaceae) and their Chemotaxonomic Significance
Cédric Mbiesset Mouzié,Beaudelaire Kemvoufo Ponou,Romuald Tematio Fouedjou,Rémy Bertrand Teponno,Léon Azefack Tapondjou 한국생약학회 2021 Natural Product Sciences Vol.27 No.2
A new steroidal saponin, (23S,24S)-spirosta-5,25(27)-diene-1β,3β,23,24-tetrol 1-O-((2,3-diacetyl-α-L-rhamnopyranosyl)-(1→2)-[β-D-xylopyranosyl-(1→3)]-α-L-arabinopyranoside)-24-O-β-D-glucopyranoside (humilisoside) together with the known β-sitosterol 3-O-glucopyranoside, adenosine, dioscin, and methylprotodioscin were isolated from the leaves of Dracaena humilis. Their structures were elucidated by spectral techniques including mass spectrometry (ESIMS, HRESIMS, tandem MS-MS), 1D NMR (1H, 13C NMR), 2D NMR (HSQC, 1H-1H COSY, HMBC, NOESY), chemical method as well as by comparison with spectroscopic data reported in the literature. The chemotaxonomic significance of the isolation of these compounds is discussed. This is the first report on the phytochemical investigation of D. humilis.