Cytotoxic compounds from the genus Centaurea.
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SHOEB, M. 2005. Cytotoxic compounds from the genus Centaurea. Robert Gordon University, PhD thesis.
This thesis, which is divided into four chapters, represents an account on the isolation, identification and the assessment of bioactivity of cytotoxic compounds from the genus Centaurea (Family: Asteraceae alto Compositae), a large genus of about 500 species. The first three chapters deal with an introduction of natural products and Centaurea species, followed by the isolation and characterisation of compounds from twelve Centaurea species. The last chapter describes the bioactivities of extracts and isolated compounds from these species. A total of 45 compounds were isolated from twelve Centaurea species, and only C. americana, C. cyanus, C. dealbata and C. macrocephala had previously been studied. Four of these are novel compounds. Four lignans arctiin, matairesinoside, matairesinol and lappaol A were isolated fromthe methanol extract of C. macrocephala seeds. Arctiin and matairesinoside were also isolated from the methanol extract of C. americana, C. bornmuel/eri, C. dealbata, C. huber-morathii, C. mucronifera, C. pamphylica, C. schischkinii and C. urvillei. The methanol extract of C. americana also afforded 20-hydroxyecdysone, 24-hydroxyecdysone, lappaol A, arctigenin and a novel compound, 3"-O-caffeoyl(9"'->3")-arctiin. The methanol extract of C. cyanus produced lariciresinol 4-0-B-D-glucoside, berchemol, moschamine and cis-moschamine. Arctigenin, astragalin, afzelin, matairesinol and a novel indole alkaloids, schischkiniin, were isolated from the methanol extract of C. schischkinii. Extract from C. bornmuelleri afforded arctigenin, astragalin, afzelin and matairesinol. The methanol extract of C. mon/ana yielded berchemol, berchemol 4'-O-B-D-glucoside, p-coumaroylquinic acid, cis-pcoumaroylquinic acid, pinoresinol, pinoresinol mono methyl ether, pinoresinol dimethyl ether, pinoresinol 4-0-B-D-glucoside, pinoresinol 4,4'di-0-B-D-glucoside, pinoresinol 4-0-apiose-(1->2)-B-D-glucoside, centcyamine, cis-centcyamine, N-(4-hydroxycinnamoyl)-5-hydroxytryptamine, cis-N-(4-hydroxycinnamoyl)-5-hydroxytryptamine, moschamine, cis-moschamine, tryptamine and two novel compounds, flavanone-apiose-glucuronic acid and montamine. C. gigantea afforded arctiopicrin, 8-0-(4-hydroxy-3-methylbutanoyl)-salonitenolide, chlorogenic acid, cirsiliol, isoquercetrin, orientin, isoorientin and 4"-hydroxybenzoyl-isoorientin. General toxicity, cytotoxicity and antioxidant activity of the extracts and isolated compounds were evaluated, respectively, by the brine shrimp lethality assay, MTT assay on human colon cancer cell line (CaCo-2) and DPPH assay. Among all the species, the methanol extract of C. bornmuelleri, C. gigantea, C. huber-morathii and C. montana were the most toxic extracts in brine shrimp lethality and MTT assay. Arctigenin (IC50=7.0 mM), matairesinol, montamine (IC50=43.9 mM) and lappol A, schischkiniin, arctiopicrin (IC50=8.5 mM) and 8-0-(4-hydroxy-3-methylbutanoyl)-salonitenolide (IC50=26.4 mM) showed higher cytotoxicity against MTT assay. Matairesinoside (IC50=2.2 x 10-3 mg/mL), matairesinol (IC50=2.0 x 10-3 mg/mL) and schischkiniin (lC50=3.8 x 10-3 mg/mL) exhibited significant free radical scavenging activities towards DPPH assay.