Topic
Indole alkaloid
About: Indole alkaloid is a research topic. Over the lifetime, 868 publications have been published within this topic receiving 15401 citations. The topic is also known as: indole alkaloids.
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TL;DR: Analysis of the primary structure-activity relationships reveals that the introduction of different substituent groups at the C-3, C-5, and C-6 positions of the indole moiety and the C -10 position of the genipin moiety might have an effect on the antitumour activity of the resulting compounds.
Abstract: A biomimetic synthetic strategy and combinatorial chemistry were used to synthesize 34 novel monoterpenoid indole alkaloid (MIA) analogues, and their cytotoxic activities against five cancer cell lines (SW-480, A-549, HL-60, SMMC-7721, and MCF-7) were determined using the 3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium (MTS) assay. Fourteen of these analogues (7, 16-18, and 23-32) showed significantly greater inhibition of tumour cell proliferation than cisplatin. Compounds 17 and 18 showed the highest cytotoxic activity against the HL-60 cell line with IC50 values of 0.90 μM and 0.43 μM, respectively. Compound 18 slightly induced apoptosis and arrested the cell cycle in SW-480, A-549, HL-60, SMMC-7721, and MCF-7 cells. Analysis of the primary structure-activity relationships reveals that the introduction of different substituent groups at the C-3, C-5, and C-6 positions of the indole moiety and the C-10 position of the genipin moiety might have an effect on the antitumour activity of the resulting compounds.
8 citations
Journal Article•
TL;DR: A test with the microalga Chlorella vulgaris was used to evaluate the allelopathic potential activity of indole alkaloids present in cereals and the toxicity of barley aqueous extracts is in agreement with the phytotoxicity of pure gramine.
Abstract: A test with the microalga Chlorella vulgaris was used to evaluate the allelopathic potential activity of indole alkaloids present in cereals. Gramine, the main indole alkaloid present in barley shows the highest toxicity. A model mechanism of action for auxin was used to analyze the structural effect on the observed toxicity. Germination inhibition on seeds and shoot length inhibition activities of gramine on barley, rye, oat, wheat, lettuce cultivars and the weed Lollium rigidum were measured. Results are discussed in relation to the phytotoxic selectivity of gramine on the seeds germination. In addition, the toxicity of barley aqueous extracts on the germination of oat seed was also determined. Phytotoxicity of the extracts is in agreement with the phytotoxicity of pure gramine.
8 citations
TL;DR: Sempervirine (2,3,4,13-tetrahydro-1H-benz[g]indolo[2, 3-a]quinolizin-6-ium, 1) was synthesized in three steps from hexahydroisochroman-3-one (6) and N-2-(3-indolyl)-ethylamine (tryptamine,7) as mentioned in this paper.
Abstract: Sempervirine (2,3,4,13-tetrahydro-1H-benz[g]indolo[2,3-a]quinolizin-6-ium,1) the pentacyclic anhydronium indole alkaloid ofGelsemium sempervirens Ait. f. (Loganiaceae), has been synthesized in three steps from hexahydroisochroman-3-one (6) and N-2-(3-indolyl)-ethylamine (tryptamine,7). The condensation product, N-2-(3-indolyl)-ethyl-2-(hydroxymethyl)-trans-hexahydrophenylacetamide (8) arising from6 and7 on double cyclization with phosphoryl chloride yielded the 3,4-dehydroyohimbane derivative9. Aromatization of rings C and D of compound9 with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) in glacial acetic acid, followed by basification, generated sempervirine (1).
8 citations
Journal Article•
TL;DR: To study chemical constituents of the leaves of Nauclea officinalis, eight alkaloids were isolated from 95% ethanol extract by various chromatographic methods and identified as naucleactonin C, which is a new indole alkaloid.
Abstract: To study chemical constituents of the leaves of Nauclea officinalis, eight alkaloids were isolated from 95% ethanol extract by various chromatographic methods. The structures were elucidated on the basis of spectroscopic data (IR, UV, ESI-MS, 1D and 2D NMR) and identified as naucleactonin C (1), strictosamide (2), vincosamide (3), pumiloside (4), angustoline (5), angustine (6), 18, 19-dihydroangustine (7) and naucleofficine D (8). Compound 1 is a new indole alkaloid. Compounds 6 and 7 were isolated from this plant for the first time.
8 citations
TL;DR: A quaternary indole alkaloid, venecurine, has been isolated by chromatographie techniques from a curare obtained from the Hoti tribe of Venezuela as mentioned in this paper.
8 citations