Cytotoxic activity alkaloids

Haliclonacyclamine F (25), arenosclerin D (26), and arenosclerin E (27) have been recently isolated from the sponge Pachychalina alcaloidifera endemic in Brazil [26]. The alkaloids 25-27 were isolated from the cytotoxic, antibiotic, and antituberculosis MeOH crude extract of P. alcaloidifera by a series of separations on silica-gel and cyanopropyl-bonded silica-gel columns. The structures of compounds 25-27 were established by the same approach employed for the structural elucidation of haliclonacyclamine E (13) and arenosclerins A-C (14-16) [18], as well as by comparison with NMR data for this last series of alkaloids. The alkaloids 25-27 displayed moderate cytotoxic activity against SF295 (human CNS), MDA-MB435 (human breast), HCT8 (colon), and HL60 (leukemia) cancer cell lines. 

Indole alkaloids Strychnos icaja roots SiOj Hx + CHCI3 + MeOH + HjO AcOEt + iPrOH + NH3 aqueous DragendorlTs reagent UV Antimalarial, cytotoxic activity 14... 

The pyrrolonaphthyridines 208 and 209 can be prepared from rearrangement of the pentacycle 207 upon treatment with trifluoroacetic acid (TFA) (Scheme 52). These products are of interest as they have the same structural skeleton as the indole alkaloid (—)-goniomitine, isolated from the root bark of Gonioma Malagasy <1995JOC3282>. Compound 208 has since been used in the synthesis of further derivatives which show cytotoxic activity against leukemia cells <2001BML79>. 

The dimeric carbazole alkaloids often occur along with the corresponding monomeric carbazoles in terrestrial plants [7,62] (Scheme 7). Clausenamine-A was obtained by Wu from the stem bark of Clausena excavata [63]. Clausen-amine-A and its synthetic analogs, like bis(O-demethylmurrayafoline-A), show cytotoxic activities against diverse human cancer cell lines [64] and exhibit moderate antimalarial activity [65,66]. Furukawa isolated l,r-bis(2-hy-droxy-3-methylcarbazole) and bismurrayaquinone-A, the first dimeric car-bazolequinone alkaloid found in nature, from Murraya koenigii [67]. 

Dennis J. McKenna and G. H. N. Towers. "Ultra-violet mediated cytotoxic activity of B-carboline alkaloids." Phytochemistry 20 (1981) 1001-1004. 

Weniger B, Italiano L, Beck JP et al (1995) Cytotoxic activity of Amaryllidaceae alkaloids. Planta Med 61(l) 77-79... 

Recently, Turner et al. described the synthesis of the alkaloid (R)-(-t-)-crispine A, which shows cytotoxic activity against HeLa human cancer cell lines, using in the final step a deracemization procedure with the combination of an enantioselective amine oxidase obtained by directed evolution methods and a chemical non-selective reducing agent (Scheme 10.20) [48]. 

In 2002, Munro et al. reported the isolation of coproverdine (271) from a New Zealand Ascidian. The name of this isolate was derived from the descriptor attached to the voucher specimen (green sheep-shit-like in appearance), hence coproverdine copro Greek dung, ovis Latin sheep, verde Latin green). This alkaloid was isolated from Nature in optically active form [a]p — 8.0 (c 0.36, EtOH). However, the absolute configuration was not assigned. Coproverdine showed cytotoxic activity against a variety of murine and human tumor cell lines (240). 

The sesquiterpene pyridine alkaloids have antifeedant and insecticidal activ-ihes. Some alkaloids, such as triptonine B, hypoglaunine B, hyponine B and wilfortrine, have antivirus activity potential. Others, such as emarginatines A-B, E-G and emarginatine, have cytotoxic activity. Ebenifoline and cangorinine have immunosuppressive activity. 

Staerk, D., Lemmich, E., Christensen, J., Kharazmi, A., Olsen, C. E. and Jaroszewski, J. W. 2000. Leishmanicidal, antiplasmodial and cytotoxic activity of indole alkaloids from Corynanthe pachyceras. Planta Medica, 66 531-536. 

Keawpradub, N., Eno-Amooquaye, E., Burke, P. J. and Houghton, P. J. 1999. Cytotoxic activity of indole alkaloids from Alstonia macrophylla. Planta Medica, 65 311-315. 

Roth, A., Kuballa, B., Bounthanh, C., Cabalion, P., Sevenet, T., Beck, J. P. and Anton, R. 1986. Cytotoxic activity of polyindole alkaloids of Psychotria forsteriana (Rubiaceae). Plant Medica, 450 53. 

Leclerq, J., Quetin, J., De Pauw-Gillet, M.-CL, Bassleer, R. and Angenot, L. 1987. Antimitotic and cytotoxic activities of guattegaumerine, a bisbenzylisoquinoline alkaloid. Planta Medica, 116-117. 

Frederich, M., Tits, M. and Angenot, L. 2003. Indole alkaloids from Strychnos species and their antiplasmodial and cytotoxic activities. Chemistry of Natural Compounds, 39(6) 513-519. 

A new bromopyrrole alkaloid 15 along with racemic 16 was isolated from the Japanese marine sponge Homaxinellct sp. They exhibit weak cytotoxic activity against P-388 lymphocytic leukemia cells with ED50 values of 21.5 pg/ml and 30 pg/ml, respectively [34]. 

Uddin J, Ueda K, Siwu ERO, Kita M, Uemura D (2006) Cytotoxic Labdane Alkaloids from an Ascidian Lissoclinum sp. Isolation, Structure Elucidation, and Structure-Activity Relationship. Bioorg Med Chem 14 6954... 

A revised structure for the catecholamide spermidine siderophore obtained from Paracoccus denitrificans has been proposed the new structure contains a centrally located oxazole ring (6).3 The soft coral Sinularia brongersmai contains two spermidine derivatives, i.e. (7) and its 10,11-dehydro-derivative [(lOi )], both of which show cytotoxic activity.4 The hypotensive principle of the root bark of Lycium chinense has been isolated as an amorphous alkaloid called kukoamine A.5 Acid hydrolysis of the alkaloid produced only spermine and dihydrocaffeic acid, which, in association with its n.m.r. spectrum, indicated the structure (8). Another hypotensive principle, ephedradine B (9), has been obtained from Ephedra roots.6... 

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