- Bioactive Triterpenoids from the Twigs of Chaenomeles sinensis
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Chaenomeles sinensis has been consumed traditionally for the treatment of throat diseases, diarrhea, inflammatory diseases, and dry beriberi. Repeated chromatography of the CHCl3-soluble fraction from the 80% MeOH extract of C. sinensis twigs led to the isolation of three new triterpenoids, sinenic acid A (1), 3β-O-cis-feruloyl-2α,19α-dihydroxyurs-12-en-28-oic acid (2), and 3β-O-cis-caffeoylbetulin (3), together with 20 analogues. The chemical structures of 1-3 were determined using diverse NMR techniques and HRMS data analysis, chemical methods, and computational approaches supported by advanced statistics (CP3). All the purified compounds were evaluated not only for their cytotoxicity against four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT-15) but for their potential neuroprotective effects through induction of nerve growth factor in C6 glioma cells. Their anti-inflammatory effects were also assessed by measuring nitric oxide levels in lipopolysaccharide-insulted murine microglia BV2 cells.
- Kim, Chung Sub,Subedi, Lalita,Oh, Joonseok,Kim, Sun Yeou,Choi, Sang Un,Lee, Kang Ro
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p. 1134 - 1140
(2017/05/05)
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- Ursane saponins from the stems of Firmiana simplex and their cytotoxic activity
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Three new ursane triterpene saponins, together with twelve known ursane triterpenes were isolated from the stems of Firmiana simplex. The structures of the saponines were elucidated on the basis of spectroscopic and chemical methods. The cytotoxic activity of all compounds was evaluated in vitro against lung adenocarcinoma (A549), ovarian cancer (SK-OV-3), skin melanoma (SK-MEL-2), and colon cancer (HCT-15) human cell lines, using a sulforhodamine (SRB) assay. 23-Hydroxyursolic acid showed cytotoxicity against the tested cell lines with IC50 values ranging from 11.96 to 14.11 μM.
- Woo, Kyeong Wan,Choi, Sang Un,Kim, Ki Hyun,Lee, Kang Ro
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p. 1450 - 1456
(2015/07/15)
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- Hepatoprotective triterpenes from traditional Tibetan medicine Potentilla anserina
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A methanol extract from the tuberous roots of Potentilla anserina (Rosaceae) exhibited hepatoprotective effects against d-galactosamine (d-GalN)/lipopolysaccharide-induced liver injuries in mice. Six triterpene 28-O-monoglucopyranosyl esters, potentillanosides A-F, were isolated from the extract along with 32 known compounds, including 15 triterpenes. The structures of potentillanosides A-F were determined on the basis of spectroscopic properties and chemical evidence. Four ursane-type triterpene 28-O-monoglycosyl esters, potentillanoside A (IC50 = 46.7 μM), 28-O-β-d- glucopyranosyl pomolic acid (IC50 = 9.5 μM), rosamutin (IC 50 = 35.5 μM), and kaji-ichigoside F1 (IC50 = 14.1 μM), inhibited d-GalN-induced cytotoxicity in primary cultured mouse hepatocytes. Among these four triterpenes, potentillanoside A, rosamutin, and kaji-ichigoside F1 exhibited in vivo hepatoprotective effects at doses of 50-100 mg/kg, p.o. The mode of action was ascribable to the reduction in cytotoxicity caused by d-GalN.
- Morikawa, Toshio,Ninomiya, Kiyofumi,Imura, Katsuya,Yamaguchi, Takahiro,Akagi, Yoshinori,Yoshikawa, Masayuki,Hayakawa, Takao,Muraoka, Osamu
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p. 169 - 181
(2014/05/06)
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- 11β-Hydroxysteroid dehydrogenase 1 inhibiting constituents from Eriobotrya japonica revealed by bioactivity-guided isolation and computational approaches
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The inhibition of 11β-hydroxysteroid dehydrogenase 1 (11β-HSD1), which catalyzes the conversion of inactive 11-ketoglucocorticoids to active 11β-hydroxyglucocorticoids, emerged as promising strategy to treat symptoms of the metabolic syndrome, including obesity and type 2 diabetes. In this study the leaves of the anti-diabetic medicinal plant loquat (Eriobotrya japonica) were phytochemically investigated following hints from a pharmacophore-based virtual screening and a bioactivity-guided approach. Determination of the 11β-HSD1 and 11β-HSD2 inhibitory activities in cell lysates revealed triterpenes from the ursane type as selective, low micro-molar inhibitors of 11β-HSD1, that is, corosolic acid (1), 3-epicorosolic acid methyl ester (4), 2-α hydroxy-3-oxo urs-12-en-28-oic acid (6), tormentic acid methyl ester (8), and ursolic acid (9). Importantly, a mixture of loquat constituents with moderate activities displayed a pronounced additive effect. By means of molecular modeling studies and the identification of the 11β-HSD1-inhibiting 11-keto-ursolic acid (17) and 3-acetyl-11-keto-ursolic acid (18) a structure-activity relationship was deduced for this group of pentacyclic triterpenes. The mechanism of action elucidated in the present work together with the previously determined pharmacological activities provides these natural products with an astonishing multi-targeted anti-diabetic profile.
- Rollinger, Judith M.,Kratschmar, Denise V.,Schuster, Daniela,Pfisterer, Petra H.,Gumy, Christel,Aubry, Evelyne M.,Brandst?tter, Sarah,Stuppner, Hermann,Wolber, Gerhard,Odermatt, Alex
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experimental part
p. 1507 - 1515
(2010/05/18)
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- Retrovirus protease inhibitors
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A compound composition and method of treating a retrovirus infection are disclosed. In particular, isolated triterpenes have been shown to have significant inhibitory activity against HIV-1.
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- An E-ring γ-lactone pentacyclic triterpene from Myrianthus serratus
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A novel γ-lactone triterpenoid has been isolated from the methylated ethyl acetate extract of the trunk wood of Myrianthus serratus, as well as friedelin and four known pentacyclic triterpenoid acids, all as their methyl esters. Their structures were elucidated by 2D NMR experiments.
- Lontsi, David,Ngounou, Ngninzeko Fernande,Tapondjou, Azefack Leon,Sondengam, Beibam Lucas,Bodo, Bernard,Martin, Marie-Therese
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p. 2473 - 2476
(2007/10/03)
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- β-GLUCOSYL ESTERS OF 19α-HYDROXYURSOLIC ACID DERIVATIVES IN LEAVES OF RUBUS SPECIES
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Key Word Index-Rubus microphyllus; R. koehneanus; R. trifidus; R. medius; Rosaceae; triterpene glucosyl esters; 19α-hydroxyursolic acid derivatives. β-Glucosyl esters of A-ring oxygenated 19α-hydroxyursolic acids were isolated from the leaves of Rubus microphyllus, R. koehneanus, R. trifidus and R. medius.Comparisons of the glycoside fractions of the leaves of 39 Rubus species were conducted, indicating the chemotaxonomic significance of this type of glucosyl ester in this genus.
- Seto, Takashi,Tanaka, Takashi,Tanaka, Osamu,Naruhashi, Naohiro
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p. 2829 - 2834
(2007/10/02)
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