Article

Antiproliferative oleanane saponins from Meryta denhamii

Dipartimento di Scienze Farmaceutiche, Universitaàdi Salerno, Via Ponte Don Melillo, 84084 Fisciano (SA), Italy.
Journal of Natural Products (Impact Factor: 3.95). 07/2008; 71(6):1000-4. DOI: 10.1021/np8000464
Source: PubMed

ABSTRACT Eight new oleanane saponins (1- 8) together with four know saponins (9-12) were isolated from the aerial parts of Meryta denhamii. Their structures were elucidated by 1D and 2D NMR experiments including 1D TOCSY, DQF-COSY, ROESY, HSQC, and HMBC spectroscopy, as well as ESIMS analysis. The antiproliferative activity of all compounds was evaluated using three murine and human cancer cell lines: J774.A1, HEK-293, and WEHI-164.

0 Followers
 · 
199 Views
  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: A series of novel 2,7-dimethyl-1,8-naphthyridine derivatives substituted with Mannich bases 2a–d, N-β-glycosides 6a–e, 7a–e, Schiff’s bases 8a–c, pyrazolone 9, and S-alkylated derivatives 10a–c have been synthesized in good yields starting from 4-hydroxy-2,7-dimethyl-1,8-naphthyridine 1 through multi-step synthesis. The newly synthesized title compounds were evaluated for their HepG2 cell growth inhibition, the results revealed that all the tested compounds process inhibitory effects on the growth of HepG2 liver cancer cells. Compound 8b showed the highest inhibition activity against HepG2 cell line (IC50 equals 3.2 μg/mL) among all tested compounds. The results were compared to 5-Fluorouracil (5-FU) and doxorubicin as reference drugs, (IC50 5 and 3.56 μg/mL). Furthermore, molecular docking of compounds 3b, 6a, and 8b into the binding site of topoisomerase II was carried out. The results of the binding energy scores of these compounds were compared to the docking score of Vosaroxin, a known 1,8-naphthyridine derivative which is in clinical trials as potential anticancer drug. Compound 8b docking result revealed that it is the only tested compound that intercalate with DNA segment of the topoisomerase II, similar to Vosaroxin which was used as reference drug for docking comparison. Graphical Abstract
    Medicinal Chemistry Research 01/2014; DOI:10.1007/s00044-013-0604-6 · 1.61 Impact Factor
  • [Show abstract] [Hide abstract]
    ABSTRACT: A bidesmosidic triterpene saponin, flaccidoside II, which was isolated from Di Wu, a Chinese folk medicine from dry rhizome of Anemone flaccida Fr. Schmidt, was efficiently synthesized in a convergent approach. We employed two glycosyl trichloroacetimidate donors in a one-pot reaction as a key step.[Supplementary materials are available for this article. Go to the publisher's online edition of the Journal of Carbohydrate Chemistry for the following free supplemental resource(s): H NMR, C NMR and HR mass spectra for all synthesized compounds, 2, 6, 9-11, and Flaccidoside II (1)
    Journal of Carbohydrate Chemistry 11/2009; 28(9):506-519. DOI:10.1080/07328300903260192 · 1.18 Impact Factor
  • [Show abstract] [Hide abstract]
    ABSTRACT: N-Acetylglucosamine-bearing triterpenoid saponins (GNTS) were reported to be a unique type of saponins with potent anti-tumor activity. In order to study the structure–activity relationship of GNTS, 24 oleanolic acid saponins with ( [TEX equation: 1 \rightarrow 3] )-linked, ( [TEX equation: 1\rightarrow 4] )-linked, ( [TEX equation: 1\rightarrow 6] )-linked [TEX equation: N] -acetylglucosamine oligosaccharide residues were synthesized in a combinatorial and concise method. The cytotoxicity of these compounds toward the leukemia cell line HL-60 and the colorectal cancer cell line HT-29 could not be improved. Half maximal inhibition below [TEX equation: 10\,\upmu \hbox {M}] was achieved in one single case. The study revealed that the activity decreased following the order of [TEX equation: 3^{\prime }>4^{\prime }>6^{\prime }] glycosyl modifications. GNTS that incorporated (d/l)-xylose and l-arabinose at positions [TEX equation: 3^{\prime }] and [TEX equation: 4^{\prime }] were more potent than those bearing other sugars.
    Molecular Diversity 02/2014; 18(1). DOI:10.1007/s11030-013-9480-8 · 2.54 Impact Factor