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At least 127 records · Page 7Linked to original sources
PubMedDate not supplied

Catharanthus alkaloids, XXXVIII. Confirming structural evidence and antineoplastic activity of the bisindole alkaloids leurosine-N'b-oxide (pleurosine), roseadine and vindolicine from Catharanthus roseus.

Additional and confirming chemical and spectroscopic evidence for vindolicine (4), roseadine (5), and leurosine-N'b-oxide (6) is presented. Leurosine-N'b-oxide (6) was found to be exceptionally active in the B-16 melanoma test system in vivo. Roseadine (5), a new isolate of Catharanthus roseus, and 6 displayed significant activity in the P-388 lymphocytic leukemia test system in vivo. Preliminary spectral studies on the new alkaloid roseamine are also described.

Animals↗
PubMedDate not supplied

Pyrrolizidine alkaloids from Cynoglossum creticum. Synthesis of the pyrrolizidine alkaloids echinatine, rinderine, and analogues.

Reinvestigation of Cynoglossum creticum led to the isolation of the previously reported echinatine [1] and heliosupine [2] as well as rinderine [3], 7-angelylheliotridine [4] and a new alkaloid, cynoglossamine [5]. The structures have been determined by spectral means (ir, ms, 1H-13C HETCOR nmr), comparison with literature data and authentic samples, and/or syntheses. In addition, 1 and all three of its isomers 3, 6, and 7 and other semisynthetic analogues (8-13) were prepared and characterized.

Cholestadienols↗
PubMed2001

General approach for the synthesis of sarpagine/macroline indole alkaloids. Enantiospecific total synthesis of the indole alkaloid trinervine.

[structure: see text] The total synthesis of the indole alkaloid trinervine 1 was accomplished in enantiospecific fashion in an overall yield of 20% (from the tetracyclic ketone 8) in 10 reaction vessels (12.5% from tryptophan methyl ester). The synthesis of the N(a)-H substituted macroline equivalent 2 was also completed in high yield via the same intermediate 13. The unique protection/hydroboration process developed here should provide a method to functionalize the C(19)-C(20) double bond in similar systems.

Animals↗
PubMedDate not supplied

Alkaloids of Thalictrum. XXII. Isolation of alkaloids with hypotensive and antimicrobial activity from Thalictrum revolutum.

Sixteen alkaloids were characterized from Thalictrum revolutum DC., namely; thalidasine, O-methylthalmethine, O-methylthalicberine, thalrugosaminine, thalicarpine, thalmelatine, pennsylvanine, palmatine, berberine, thalifendine, columbamine, jatrorrhizine, deoxythalidastine, thalphenine and magnoflorine. The structure of thairugosaminine (1) a bisbenzylisoquinoline type which was previously proposed on partial data was completely established, including the absolute configuration as S,S. Thalphenine, thalidasine, O-methylthalicberine, thalicarpine, thalrugosaminine and thaliglucinone were found to possess hypotensive activity in rabbits. Thalrugosaminine, thalicarpine, thalmelatine, O-methylthalmethine, pennsylvanine and thalphenine were found to be active against Mycobacterium smegmatis.

Alkaloids↗
PubMed1987

A rapid analysis of water for anatoxin a, the unstable toxic alkaloid from Anabaena flos-aquae, the stable non-toxic alkaloids left after bioreduction and a related amine which may be nature's precursor to anatoxin a.

Poisoning of animals by Anabaena Flos-Aquae alkaloid is a common, but sporadic event (1). Anatoxin A is the toxic principle responsible for acute fatalities (2), and tends to disappear along with the toxicity within a few days of the event, thus complicating diagnosis. This report reveals our simplified analytical methodology for Anatoxin A (2-acetyl-9-azabicyclo[4.2.1] non-2,3-ene), for the non-toxic compounds into which it bioreduces, the chair and boat forms of 2-acetyl-9-azabicyclo[4.2.1] nonane, and for an as yet uncharacterized amine C10H15N.

Acetylation↗
PubMed1995

Reduction of toxicity of a vinca alkaloid by an anti-vinca alkaloid antibody.

Inadvertent oncolytic overdoses occur rarely, but can have serious consequences. We have investigated the possibility of using an antibody, 27.8.1A, reactive with vinca alkaloids, as a means of reducing the toxicity associated with overdose situations. In vitro cytotoxicity of a vinca derivative, 4-desacetyl- vinblastine-3-carbox-hydrazide (DAVLBHYD), with and without the addition of 27.8.1A, was determined. Using CCRF-CEM, a human acute lymphoblastic leukemia cell line, as a target in this assay, we observed a greater than 90% increase in cell viability using 100 micrograms/ml 27.8.1A with a 0.1 microgram/ml concentration of DAVLBHYD. 27.8.1A had no effect on cell viability when doxorubicin was used as a control drug in this assay. Similarly, the addition of an irrelevant antibody. EGFrL11, had no effect on the toxicity of DAVLBHYD. In an in vivo survival experiment, nude mice were injected with a toxic dose of DAVLBHYD and subsequently given four doses of 27.8.1A. All anti vinca antibody-treated mice survived, in contrast to the untreated group or irrelevant antibody-treated group in which only 25% and 10% of the mice survived, respectively.

Animals↗
PubMed1997

Polycyclic aromatic alkaloids. XII: In vitro- and in vivo-investigations of the cytotoxic marine alkaloid 2-bromoleptoclinidinone.

Aminoquinone 2a, the tetracyclic quinone 3b, and the pentacyclic alkaloid 2-bromoleptoclinidinone (4a) were submitted to the NCl standard in vitro assay using 60 tumor cell lines. Compound 4a showed very high in vitro cytotoxicity and was therefore selected for further evaluation. In the in vivo screening 4a was tested at maximally tolerated doses in four models, but no significant antitumor activity could be found.

Animals↗