Effects of the β-carbolines, harmane and pinoline, on insulin secretion from isolated human islets of Langerhans

Cooper, Eric J.; Hudson, Alan L.; Parker, Christine A.; Morgan, Noel G.

doi:10.1016/j.ejphar.2003.09.039

Cited by 55 publications

(33 citation statements)

References 50 publications

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“…Further studies are required to find compatible carrier materials for these compounds and to investigate the releasing rate of the compounds from appropriate carriers. However, the various pharmacological activities described for β-carbolines like norharmane (Chiarugi et al, 2000;Connop et al, 1995;Cooper et al, 2003;Totsuka et al, 2004) should be kept clearly in mind because this could limit their usability as antifouling agents.…”

Section: Discussionmentioning

confidence: 97%

Antialgal Activity of Several Cyanobacterial Exometabolites

Volk

2006

J Appl Phycol

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The isolation of norharmalane (3,4-dihydro-9H-pyrido(3,4-b)indole) from culture media of the cyanobacterium Nodularia harveyana is described. The minimum toxic quantities against selected cyanobacteria of this compound, of the two known cyanobacterial exometabolites 4,4 -dihydroxybiphenyl and norharmane (9H-pyrido(3,4-b)indole) and in addition of harmane (1-methyl-9H-pyrido(3,4-b)indole) were determined using a special TLC plate assay. The three β-carbolines harmane, norharmane and norharmalane were tested both as bases and as hydrochlorides. All four test compounds were found to be cytotoxic against the cyanobacterial test organisms in low quantities (0.5 to 18.0 μg). For the β-carbolines the following structure-response relationships were revealed: the double bond in position 3-4 and possibly the 1-methyl-group increased the cytotoxic effect of these indole alkaloids. Minimum toxic quantities detected for β-carboline bases were in general lower than those of equimolar amounts of the corresponding hydrochlorides. The possible applicability of both β-carbolines and biphenyls as agents in antifouling systems is discussed.

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Section: Discussionmentioning

confidence: 97%

Antialgal Activity of Several Cyanobacterial Exometabolites

Volk

2006

J Appl Phycol

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“…Larsen et al (1994) described the isolation of three chlorine-containing β-carbolines (the so-called bauerines A-C) from the cyanobacterium Dichotrix baueriana. Although various pharmacological effects of norharmane have been found, such as the inhibition of indoleamine 2,3-dioxygenase and nitric oxide synthase (Chiarugi et al, 2000;Connop et al, 1995) or an increase of insulin secretion from isolated human Islets of Langerhans (Cooper et al, 2003), the therapeutical benefit of norharmane is low because of its co-mutagenic activity (Totsuka et al, 1998(Totsuka et al, , 2004. Searching for useful agents to control blooms of cyanobacteria, Kodani et al (2002) isolated harmane (1-methyl-β-carboline) from the algicidal bacterium Pseudomonas sp.…”

Section: Discussionmentioning

confidence: 98%

Screening of microalgal culture media for the presence of algicidal compounds and isolation and identification of two bioactive metabolites, excreted by the cyanobacteria Nostoc insulare and Nodularia harveyana

Volk

2005

J Appl Phycol

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Culture medium extracts obtained from 115 culture media of 35 different microalgae species were screened for the presence of algicidal compounds, in particular for compounds which are cytotoxic to Arthrospira (Spirulina) laxissima. In agar plate diffusion tests and in a test system combining thin layer chromatography (TLC) with the use of an aqueous suspension of living A. laxissima cells as spray reagent, 14 microalgae species were found with cytotoxic activity of different intensity to A. laxissima. In a so-called TLC plate diffusion test, using A. laxissima and other microalgae as test organisms, the culture medium extracts of Nodularia harveyana and Nostoc insulare possessed the highest strength and range of algicidal activity. The algicidal compound in the culture medium extracts of Nodularia harveyana was shown to be norharmane (9H-pyrido(3,4-b)indole), a known indole alkaloid. The main algicidal compound in culture medium extracts of Nostoc insulare was identified as 4,4 -dihydroxybiphenyl. The possible applicability of both compounds as therapeutics or as useful agents for removing cyanobacterial water blooms or for developing new antifouling systems is discussed.

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“…Although structurally unrelated to imidazolines, ␤-carbolines might be endogenous ligands of the "imidazoline binding sites." Interestingly, two ␤-carbolines, harmane and pinoline, possess insulin-releasing properties in vitro (99).…”

Section: Site 4: Activation Of Amplifying Pathwaysmentioning

confidence: 99%