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Journal ArticleDOI

The simple β-carboline alkaloids

01 Jan 1980-Phytochemistry (Pergamon)-Vol. 19, Iss: 8, pp 1573-1582
TL;DR: The simple β-carbolines are presented as a distinct group of alkaloids displaying structural modification of three basic ring systems and aspects of their metabolism, pharmacological properties and taxonomic significance are briefly summarized.
About: This article is published in Phytochemistry.The article was published on 1980-01-01. It has received 253 citations till now.
Citations
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Journal ArticleDOI
TL;DR: The levels of DMT and beta-carbolines found in the ayahuasca samples examined in the present study were an order of magnitude greater than the levels reported in a previous study, which indicated that their effects in combination are additive, rather than synergistic or antagonistic.

329 citations

Journal ArticleDOI
TL;DR: Ayahuasca is a hallucinogenic beverage that is prominent in the ethnomedicine and shamanism of indigenous Amazonian tribes as discussed by the authors and is used as a sacrament by several syncretic churches.

286 citations

Journal ArticleDOI
TL;DR: The enantioselective oxidative C-H functionalization of tetrahydroisoquinoline derivatives is achieved through the merger of photoredox and asymmetric anion-binding catalysis and introduces a potentially general approach to asymmetric transformations in oxidative photocatalysis.
Abstract: The enantioselective oxidative C–H functionalization of tetrahydroisoquinoline derivatives is achieved through the merger of photoredox and asymmetric anion-binding catalysis. This combination of two distinct catalysis concepts introduces a potentially general approach to asymmetric transformations in oxidative photocatalysis.

231 citations

Journal ArticleDOI
TL;DR: The antimicrobial activity of two cyanobacterial exometabolites, norharmane (9H-pyrido(3,4-b)indole) and 4,4'-dihydroxybiphenyl, was determined in suspension assays and the natural function as allelopathic chemicals and a possible applicability as antifouling agents or leads for the development of new antIFouling chemicals are discussed.

223 citations

Journal ArticleDOI
TL;DR: The literature data on levels of norharman and harman in fried meat and fish, meat extracts, alcoholic drinks, and coffee brews is summarized to indicate that inhalative exposure leads to a rapid increase in plasma levels and high bioavailability of norHarman and Harman and there are indications that sublingual absorption may increase dietary uptake of beta-carbolines.

198 citations

References
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Journal ArticleDOI
TL;DR: Harmaline and related compounds have been shown to be potent inhibitors of monoamine oxidase effecting 50 per cent inhibition of serotonin metabolism at 10−6 M.

177 citations

Journal ArticleDOI
TL;DR: Harmine, Harmaline, Tetrahydroharmine and Dimethyltryptamine have been found in the Ayahuasca drink.
Abstract: The Sharanahua and Culina, small Indian tribes located in the southwestern Amazon basin, use a hallucinogenic drink for medicinal and social purposes. This decoction, called “Ayahuasca” in Peru, is prepared from Banisteriopsis Caapi stems and Psychotria sp. leaves. These plants have been botanically identified on the basis of voucher herbarium specimens and investigated for alkaloid content by means of a gas chromatography-mass spectrometry technique. A list of other occasional plant admixtures is given. Harmine, Harmaline, Tetrahydroharmine, Harmol and 6-Methoxytryptamine have been found in Banisteriopsis Caapi. Dimethyltryptamine, Monomethyltryptamine and 2-methyl-1,2,3,4-tetrahydro-β-carboline have been found in Psychotria viridis and Psychotria carthaginensis. Harmine, Harmaline, Tetrahydroharmine and Dimethyltryptamine have been found in the drink. Quantitative calculations show the amount of each alkaloid administered in the Ayahuasca drink.

153 citations

Journal ArticleDOI
TL;DR: Harmane and norharmane were isolated from cured tobacco and its smoke and the addition of radioactive tryptophan to the tobacco resulted in the isolation of radioactive harmane alkaloids in the smoke, establishing the presence of indole alkaloid in tobacco.

151 citations

Journal ArticleDOI
TL;DR: Agarose gel electrophoresis of circular DNA, closed in the presence or absence of norharman revealed that the dye intercalates DNA, thereby causing 17 +/- 3 degrees unwinding of the double helix.
Abstract: The interactions of norharman (9H-pyrido [3,4-b] indole) and harman (1-methyl-9H-pyrido [3,4-b] indole) with DNA were studied. DNA caused remarkable fluorescence quenching and change in the absorption spectra of the dyes. Scatchard plots obtained by optical titration gave Kd values of 2.2 X 10(-5)M and 7.7 X 10(-6)M, and apparent numbers of binding sites of 0.13/base and 0.12/base for norharman and harman, respectively. Agarose gel electrophoresis of circular DNA, closed in the presence or absence of norharman revealed that the dye intercalates DNA, thereby causing 17 +/- 3 degrees unwinding of the double helix.

139 citations