Evolitrine

Quinoline alkaloids from Acronychia laurifolia.[Pubmed:10466225]

Phytochemistry. 1999 Sep;52(1):95-8.

Bioassay-directed fractionation of a root extract of Acronychia laurifolia (Rutaceae) using the KB-V1+ human tumor cell line led to the isolation of six quinoline alkaloids. One of these alkaloids is novel, namely, 2,3-methylenedioxy-4,7-dimethoxyquinoline and the other five were identified as the known compounds, Evolitrine, gamma-fagarine, skimmianine, kokusaginine and maculosidine. Two known bis-tetrahydrofuran lignans, sesamolin and yangambin, were also identified. The structure of the new alkaloid was determined by spectroscopic methods. All of the isolates were evaluated against a panel of human cancer cell lines; four of the alkaloids showed weak cytotoxic activity.

Alkaloids from Ruta montana.[Pubmed:10680183]

Phytochemistry. 2000 Jan;53(2):277-9.

Two known and four new quinoline and 4-quinolone type alkaloids were isolated from Ruta montana collected from Rommani (Morocco). The known compounds were 1-methyl-4-methoxy-2-quinolone and Evolitrine. The structures of the new compounds were established from 1D and 2D NMR experiments including HMQC, HMBC and MS spectral methods as 2-(nonan-8-one)-(1H)-4-quinolone, 2-(nonan-8-one)-4-methoxy-quinoline, 2-(nonan-8-one)-N-methyl-4-quinolone and 2-(decan-9-one)-N-methyl-4-quinolone.

Furoquinoline alkaloids as photosensitizers in Chlamydomonas reinhardtii.[Pubmed:2067526]

Mutat Res. 1991 Jul;249(1):105-10.

Seven naturally occurring furoquinoline alkaloids were investigated for their photobiological activity using arg-1 cells of Chlamydomonas reinhardtii. UV-A-mediated toxicity of the compounds was calculated from the colony-forming ability of the treated cells. The UV-A-mediated mutagenicity was measured by counting the number of Arg+ revertants induced by the treatment. Dictamnine was found to be the strongest mutagen as well as the most toxic compound of the group. The mutagenic activities were measured as mutation frequencies at equal substance concentration and ranked in the following order: An increase in the number of substituents on the lateral aromatic nucleus greatly decreased the photomutagenicity. Except for Evolitrine, a similar ranking order was found as reported for the dark mutagenicity of these compounds in Salmonella typhimurium strain TA98. Based on the result that furoquinolines are able to intercalate into DNA, we assume that the different mutagenic potencies may reflect differences in the geometry of the intercalation complex, which is important for the subsequent photochemical reaction.

Furoquinoline alkaloids isolated from Balfourodendron riedelianum as photosynthetic inhibitors in spinach chloroplasts.[Pubmed:23416711]

J Photochem Photobiol B. 2013 Mar 5;120:36-43.

In the search for natural inhibitors of plant growth, we investigate the mechanism of action of the natural furoquinoline alkaloids isolated from Balfourodendron riedelianum (Rutaceae): Evolitrine (1), kokusaginine (2), gamma-fagarine (3), skimmianine (4) and maculosidine (5) on the photosynthesis light reactions. Their effect on the electron transport chain on thylakoids was analyzed. Alkaloids 1, 2, 4 and 5 inhibited ATP synthesis, basal, phosphorylating and uncoupled electron transport acting as Hill reaction inhibitors on spinach chloroplasts. Alkaloid 3 was not active. The inhibition and interaction site of alkaloids 1, 2, 4 and 5 on the non-cyclic electron transport chain was studied by polarography and fluorescence of the chlorophyll a (Chl a). The results indicate that the target for 1 was localized on the donor and acceptor side of PS II. In addition alkaloids 2 and 5 affect the PS I electron acceptors on leaf discs.

Inhibitory effects of furoquinoline alkaloids from Melicope confusa and Dictamnus albus against human phosphodiesterase 5 (hPDE5A) in vitro.[Pubmed:16042076]

Arch Pharm Res. 2005 Jun;28(6):675-9.

Eight furoquinoline alkaloids were purified from two plants belonging to the Rutaceae family. Kokusaginine, skimmianine, Evolitrine, and confusameline were purified from Melicope confusa, and haplopine, robustine, dictamine, and gamma-fagarine from Dictamnus albus. In this study, the eight furoquinoline alkaloids were examined for inhibitory potency against human phosphodiesterase 5 (hPDE5A) in vitro. DNA encoding the catalytic domain of human PDE5A was amplified from the mRNA of T24 cells by RT-PCR and was fused to GST in an expression vector. GST-tagged PDE5A was then purified by glutathione affinity chromatography and used in inhibition assays. Of the eight alkaloids, gamma-fagarine was the most potent inhibitor of PDE5A, and its single methoxy group at the C-8 position was shown to be critical for inhibitory activity. These results clearly illustrate the relationship between PDE5A inhibition and the methoxy group position in furoquinoline alkaloids.

A new quinoline epoxide from the Australian plant Drummondita calida.[Pubmed:21472648]

Planta Med. 2011 Sep;77(14):1644-7.

A drug discovery program aimed at identifying new antimalarial leads from a prefractionated natural product library has resulted in the purification of a new quinoline alkaloid, (2' R)-2',3'-epoxy- N-methylatanine (1), along with eight known natural products, skimmianin, gamma-fagarine, maculosidine, Evolitrine, dictamnine, pteleine, N-methylatanine, and werneria chromene. Compound 1 displayed 74 % inhibition at 80 microM against a chloroquine -resistant Plasmodium falciparum strain (Dd2).