Cytotoxic cardenolide glycoside from the seeds of Cerbera odollam

Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand.
Phytochemistry (Impact Factor: 2.55). 02/2004; 65(4):507-10. DOI: 10.1016/j.phytochem.2003.10.019
Source: PubMed


A cardenolide glycoside, 3 beta-O-(2'-O-acetyl-l- thevetosyl)-15(14-->8)-abeo-5 beta-(8R)-14-oxo-card-20(22)-enolide (2'-O-acetyl cerleaside A), was isolated from a methylene chloride extract of the seeds of Cerbera odollam, together with four known compounds: cerleaside A, 17 alpha-neriifolin, 17 beta- neriifolin and cerberin. Their structures were elucidated by spectroscopic methods. All compounds except cerleaside A exhibited cytotoxic activities against oral human epidermoid carcinoma (KB), human breast cancer cell (BC) and human small cell lung cancer (NCI-H187).

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    • "Methanol extract of leaves of C. odollam strongly inhibited MCF-7 and T47D cells.[23] Cardenolides from seeds of C. odollam had cytotoxic activity against KB, BC, and NCI-H187 cells.[34] Potent cytotoxic activity was reported in ethanol extracts of fruits and leaves of Cerbera manghas.[35] "
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    ABSTRACT: The anticancer properties of Apocynaceae species are well known in barks and roots but less so in leaves. In this study, leaf extracts of 10 Apocynaceae species were assessed for antiproliferative (APF) activities using the sulforhodamine B assay. Their extracts were also analyzed for total alkaloid content (TAC), total phenolic content (TPC), and radical scavenging activity (RSA) using the Dragendorff precipitation, Folin-Ciocalteu, and 1,1-diphenyl-2-picrylhydrazyl (DPPH) assays, respectively. Leaf extracts of Alstonia angustiloba, Calotropis gigantea, Catharanthus roseus, Nerium oleander, Plumeria obtusa, and Vallaris glabra displayed positive APF activities. Extracts of Allamanda cathartica, Cerbera odollam, Dyera costulata, and Kopsia fruticosa did not show any APF activity. Dichloromethane (DCM) extract of C. gigantea, and DCM and DCM:MeOH extracts of V. glabra showed strong APF activities against all six human cancer cell lines. Against breast cancer cells of MCF-7 and MDA-MB-231, DCM extracts of C. gigantea and N. oleander were stronger than or comparable to standard drugs of xanthorrhizol, curcumin, and tamoxifen. All four extracts of N. oleander were effective against MCF-7 cells. Extracts of Kopsia fruticosa had the highest TAC while those of Dyera costulata had the highest TPC and RSA. Extracts of C. gigantea and V. glabra inhibited the growth of all six cancer cell lines while all extracts of N. oleander were effective against MCF-7 cells. Extracts of C. gigantea, V. glabra, and N. oleander therefore showed great promise as potential candidates for anticancer drugs. The wide-spectrum APF activities of these three species are reported for the first time and their bioactive compounds warrant further investigation.
    No preview · Article · Apr 2011 · Pharmacognosy Research
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    • "IC 50 = 0.6 lM (Tan 2007) Mitsoamide (75) Lipopeptide Cyanobacterium Geitlerinema sp. IC 50 = 460 nM (Andrianasolo et al. 2007) Borophycin (76) Boric acid containing polyketide Cyanobacterium Nostoc linckia IC 50 = 20 ng/ml (Dunlap et al. 2007; König and Wright 1996) Xylogranatins A–D (79–82) Tetranortriterpene Mangrove Xylocarpus granatum IC 50 \ 15 lM (Yin et al. 2006) Granaxylocarpins A (83) and B (84) Limonoid Mangrove Xylocarpus granatum IC 50 \ 10 lM (Yin et al. 2007) 3-chlorodeoxylapachol (85) Naphtoquinone Mangrove Avicennia germinans GI 50 \ 5 lg/ml (Jones et al. 2005) Stenocarpoquinone B (86) Naphtoquinone Mangrove A. marina GI 50 \ 5 lg/ml (Han et al. 2007) 2 0 -O-acetyl cerleaside A (87) Cardenolide glycoside Mangrove Cerbera odollam ED 50 \ 8 lg/ml (Laphookhieoa et al. 2004) 17b-neriifolin (88) Cardenolide glycoside Mangrove C. odollam ED 50 \ 8 lg/ml (Laphookhieoa et al. 2004) Cerberin (89) Cardenolide glycoside Mangrove C. odollam ED 50 \ 8 lg/ml (Laphookhieoa et al. 2004) "
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    ABSTRACT: Since early human history, plants have served as the most important source of medicinal natural products, and even in the “synthetic age” the majority of lead compounds for pharmaceutical development remain of plant origin. In the marine realm, algae and seagrasses were amongst the first organisms investigated by marine natural products scientists on their quest for novel pharmaceutical compounds. Forty years after the pioneering work in the field of marine drug discovery began, the biodiversity of marine organisms investigated as potential sources of anticancer, anti-inflammatory, and antibiotic compounds has increased tremendously. Nonetheless, marine plants are still an important source of novel secondary metabolites with interesting biomedical properties. The present review focuses on the antitumour properties of compounds isolated from marine algae, phytoplankton, mangroves, seagrasses, or cordgrasses. Compounds produced by marine epi- or endophytic fungi are also discussed. KeywordsCancer-Marine plants-Natural products-Phytoplankton-Symbionts
    Full-text · Article · Dec 2010 · Phytochemistry Reviews
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    • "The tree is also widely grown in parks, gardens and along the roadside as a shade tree. The studies of Laphookhieo et al. (2004) and Gaillard et al. (2004) showed that C. odollam contains poisonous compounds used as insecticides against hair mites. Rahman et al. (1993) showed that N-butanol extracts from the C. odollam seed caused mortality of Culex quinquefasciatus and Aedes aegypti larvae. "
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    ABSTRACT: Metallic-based wood preservatives currently face some restrictions over disposal and environmental issues; one possibility to develop new more benign systems is to study extractives in naturally durable woody plants. This study investigated the resistance of extracts from the leaf, fruit, wood, bark, seed and flower of Cerbera odollam to deterioration from fungus and termites. Antifungal assays with n-hexane, ethyl acetate, ethanol and methanol extracts were evaluated using paper discs. Termite mortality was evaluated with the methanol extract against Coptotermes gestroi. Physical and protective properties of particleboard impregnated with C. odollam extracts, including thickness swelling, internal bond strength, formaldehyde release, termite-decay and soil burial decay were investigated. Methanol wood extracts from C. odollam showed the highest activities against Trametes versicolor, Pycnoporus sanguineus, and Schizophyllum commune in the paper disc antifungal assay. Methanol flower extracts exhibited high performance in termite mortality, termite-decay and soil burial decay. Thickness swelling, internal bond strength and the formaldehyde emission of particleboard specimens treated with methanol extracts of C. odollam were up to the EN Standards.
    Full-text · Article · Dec 2009 · International Biodeterioration & Biodegradation
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