Indole alkaloids from the seeds of Centaurea cyanus (Asteraceae)

Department of Chemistry, University of Aberdeen, Aberdeen, Scotland, United Kingdom
Phytochemistry (Impact Factor: 2.55). 09/2001; 57(8):1273-6. DOI: 10.1016/S0031-9422(01)00084-X
Source: PubMed


Preparative RP-HPLC analysis of a methanol extract of the seeds of Centaurea cyanus afforded four indole alkaloids: moschamine, cis-moschamine, centcyamine and cis-centcyamine, the latter two being new natural products. Structures of these compounds were elucidated by comprehensive spectroscopic analyses. General toxicity of the isolates was determined by Brine Shrimp Lethality bioassay.

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    • "The folk medicinal uses of Centaurea species include; wound healing, antidiabetic, antidiarrhetic, antirheumatic, anti-inflammatory, colagog, choleretic, digestive, stomachic, diuretic, menstrual, astringent, hypotensive, antipyretic, cytotoxic and antibacterial purposes (Arif, Küpeli & Ergun, 2004; Yeşilada et al., 1999; Demirci et al., 2008a). Phytochemistry studies on various Centaurea species reports isolation of flavonoids, sesquiterpene lactones, triterpenes and alkaloid type nonvolatile secondary metabolites (Flamini et al., 2002; Flamini et al., 2004; Massiot et al., 1985; Sarker et al., 2001). The essential oils of Centaurea species are usually characterized with caryophyllene, eudesmol, germacrene, spathulenol type sesquiterpenes (Dob et al., 2009; Formisano et al., 2010; Senatore et al., 2003); hexadecanoic acid, tetradecanoic acid, dodecanoic acid type fatty acids (Formisano et al., 2008; Karamenderes, Demirci & Başer, 2008); heptacosane, nonacosane, pentacosane, tricosane type higher alkanes (Demirci et al., 2008a; Formisano et al., 2010; Senatore et al., 2003) and pinene, terpinene, carvacrol type monoterpenes (Karamenderes, Demirci & Başer, 2008; Salmanpour, Khalilzadeh & Sadeghifar, 2009) as the major compounds. "
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    ABSTRACT: Essential oil composition of Centaurea kilaea flowers, stems and C. cuneifolia flowers were investigated by GC, GC/MS. Flowers and stems of C. kilaea afforded very low essential oil yield <0.01% (v/w). Nineteen and twenty compounds were identified in the flower and stem oils which represent 59.5% and 77.6% of the C. kilaea oil respectively. The main components of the C. kilaea flower oil were hexadecanoic acid 26.2%, tetradecanoic acid 18.1%, β-Eudesmol 3.3% and decanoic acid 3.1%. The stem oil contains hexadecanoic acid 55.5% and β-Eudesmol 3.2%. Flowers of C. cuneifolia afforded very low essential oil yield <0.01% (v/w). Twenty five compounds were identified in the flower oil of C. cuneifolia which represent 69.92% of the oil. The main components of this oil include hexadecanoic acid 32.9%, tetradecanoic acid 14.4%, heptacosane 6.1% and nonacosane 4.3%. Essential oils obtained from both species have saturated fatty acids and alkanes as the major components, but both oils also contain minor amounts of sesquiterpenes.
    Full-text · Article · Dec 2014
    • "The identification of natural compounds as a PLK1 inhibitor prompted us to further investigate the inhibitory activity of natural compounds isolated from plants. Plants belonging to Asteraceae species are a source of many biologically active compounds such as essential oils,[25262728] polyphenolic compounds,[2930] flavonoids,[31323334] terpenoids,[3235363738] phenolic acids,[313439] alkaloids,[40] lignans,[31] saponins,[323841] stilbenes, sterols,[34] polysaccharides,[35] and many others. Plants from Asteraceae family are commonly used in treatment of various diseases including cancer due to their bio-active properties. "
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    ABSTRACT: Natural products from plant sources, embracing inherently ample structural diversity than synthetic ones are the major sources of anticancer agents and will constantly play as protagonists for discovering new drugs. Polo-like kinases (PLKs) play a leading role in the ordered execution of mitotic events and 4 mammalian PLK family members have been identified. PLK1 is an attractive target for anticancer drugs in mammalian cells, among the four members of PLKs. The present study expresses the molecular interaction of compounds (1,2-Benzenedicarboxylic acid bis (2 ethylhexyl) ester, squalene, 3,5-bis (1,1-dimethylethyl) phenol, Pentamethyl tetrahydro-5H-chromene, (1,4-Cyclohexylphenyl) ethanone and 6-Vinyl-7-methoxy-2,2-dimethylchromene) isolated from methanolic extract of leaves of Ageratum houstonianum with PLK1 enzyme. Docking between PLK1 and each of these compounds (separately) was performed using "Auto dock 4.2." (1,4-Cyclohexylphenyl) ethanone showed the maximum potential as a promising inhibitor of PLK1 enzyme with reference to ∆G (-6.84 kcal/mol) and Ki (9.77 μM) values. This was sequentially followed by Pentamethyl tetrahydro-5H-chromene (∆G = -6.60 kcal/mol; Ki = 14.58 μM), squalene (∆G = -6.17 kcal/mol; Ki = 30.12 μM), 6-Vinyl-7-methoxy-2,2-dimethylchromene (∆G = -5.91 kcal/mol; Ki = 46.68 μM), 3, 5-bis (1,1-dimethylethyl) phenol (∆G = -5.70 kcal/mol; Ki = 66.68 μM) and 1,2-Benzenedicarboxylic acid bis (2 ethylhexyl) ester (∆G = -5.58 kcal/mol; Ki = 80.80 μM). These results suggest that (1,4-Cyclohexylphenyl) ethanone might be a potent PLK1 inhibitor. Further, in vitro and in vivo rumination are warranted to validate the anticancer potential of (1,4-Cyclohexylphenyl) ethanone.
    No preview · Article · Mar 2014 · Pharmacognosy Magazine
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    • "Serotomide (trans-N-caffeoylserotonin) and safflomide (trans-N-caffeoyltryptamine) belong to serotoninderived phenylpropenoid amides produced in plants via forming an amide bond between the carboxyl group of phenylpropenoic acid and the amine groups of serotonin derivatives (Fig. 1) (Akhondzadeh et al., 2007; Jang et al., 2004; Kang et al., 2006; Sarker et al., 2001; Niwa et al., 2000). The phenylpropenoid amides are found in several plants, including Coffea canephora, Theobroma cacao, Amorphophallus konja, Ipomoea obscura and Carthamus tinctorius (Niwa et al., 2000; Stark et al., 2006; Jenett-Siems et al., 2003; Zhang et al., 1997). "
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    ABSTRACT: Serotomide (trans-N-caffeoylserotonin) and safflomide (trans-N-caffeoyltryptamine) belong to serotonin-derived phenylpropenoid amides found in plants. In this paper, serotomide and safflomide were investigated to determine their effects on serotonin receptor 5-HT1 in the renal epithelial (OK) cells, due to their structural similarity to 5-HT1 receptor ligands. At the concentration of 10 microM, serotomide was able to inhibit forskolin-stimulated cAMP formation in the OK cells by 31% (p<0.019). The inhibition was repressed by Nan-190 and spiperone (5-HT1 antagonists), suggesting that serotomide suppresses cAMP formation via binding to 5-HT1 receptors in the OK cells. Meanwhile, safflomide could not inhibit forskolin-stimulated cAMP formation at the same concentration (10 microM), but repress the inhibition of forskolin-stimulated cAMP by serotonin agonists (e.g., serotonin and 8-OH-DPAT) by 31% (p<0.018), suggesting that safflomide may block 5-HT1 receptors in a similar way to Nan-190 and spiperone. All together the data indicate that serotomide and safflomide may be potent compounds that respectively act to activate and to block 5-HT1 receptors on OK cells.
    Full-text · Article · Dec 2008 · Phytomedicine: international journal of phytotherapy and phytopharmacology
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