<b>Biosynthesis of Indole Alkaloids. The Aspidosperma and Iboga Bases</b>

Wenkert, Ernest

doi:10.1021/ja00860a023

Cited by 194 publications

(71 citation statements)

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“…Indole phytoalexin accumulates in Brassica species with hyper-resistance to microbial infection [67]. However, indole alkaloids are only produced in a few plants, such as Catharanthus roseus [68], Rauwolfia serpentina [69], Aspidosperma [70], and Camptotheca acuminate [71]. Typically, only small amounts of indole alkaloids are found in plants with the exception of Catharanthus roseus, which is the sole source in the commercial production of various indole alkaloids [6].…”

Section: Discussionmentioning

confidence: 99%

Enhanced metabolic process to indole alkaloids in Clematis terniflora DC. after exposure to high level of UV-B irradiation followed by the dark

et al. 2016

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BackgroundIndole alkaloids, which characteristically contain an indole nucleus, have pharmaceutical potential in a diverse range of applications. UV-B can elicit the accumulation of indole alkaloids. The indole alkaloid (6-hydroxyl-1H-indol-3-yl) carboxylic acid methyl ester with cytotoxic activity was found to accumulate in Clematis terniflora DC. leaves after exposure to high level of UV-B irradiation and the dark. However, a more in-depth analysis of the process behind this response has not yet been performed. Therefore, an integrated approach involving metabolomic, proteomic, and transcriptomic analyses is essential to detail the biosynthetic mechanisms of the regulation of indole alkaloid under binary stress.ResultsIndole alkaloid (6-hydroxyl-1H-indol-3-yl) carboxylic acid methyl ester was found to increase 7-fold in C. terniflora leaves post-treatment with high level of UV-B irradiation followed by an incubation in the dark compared with pre-treatment. Analysis by proteomics and metabolomics indicates a decrease in photosynthesis and carbohydrate metabolism, respectively. By contrast, amino acid metabolism was activated by this binary stress, and, specifically, the genes involved in the metabolic pathway converting shikimate to L-tryptophan were concurrently upregulated. Metabolites involved in indole biosynthesis (shikimate metabolic) pathway were anthranilate, indole, and L-tryptophan, which increased 2-, 441-, and 1-fold, respectively. In addition, there was an increase of 2- and 9-fold in L-serine deaminase (L-SD) and L-tryptophan synthase activity in C. terniflora leaves after exposure to high level of UV-B irradiation and the dark.Conclusions(6-hydroxyl-1H-indol-3-yl) carboxylic acid methyl ester was found to increase in response to high level of UV-B irradiation followed by an incubation in the dark, implying that indole alkaloid biosynthesis was activated in C. terniflora leaves. Analysis of perturbations in metabolism in these leaves demonstrated that amino acid metabolism was specifically activated by this binary stress. In addition, an enhancement in serine level and L-SD activity was noted, which likely leads to an accumulation of pyruvate that, in turn, supplies shikimate metabolic pathway. The genes, metabolites, and L-tryptophan synthase activity that are involved in the metabolic pathway leading from shikimate to L-tryptophan all increased under the experimental binary stress, resulting in an enhancement of indole biosynthesis (shikimate metabolic) pathway. Therefore, the metabolic process to indole alkaloids in C. terniflora was enhanced after exposure to high level of UV-B irradiation followed by the dark.Electronic supplementary materialThe online version of this article (doi:10.1186/s12870-016-0920-3) contains supplementary material, which is available to authorized users.

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Section: Discussionmentioning

confidence: 99%

Enhanced metabolic process to indole alkaloids in Clematis terniflora DC. after exposure to high level of UV-B irradiation followed by the dark

et al. 2016

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“…tetrahydroharman ( I 17), just as phenethylamine derivatives can condense with aldehydes or other carbonyl compounds. Tetrahydroharman is the parent substance of the harmala alkaloids liarmaline (114), harmine (115), and harmdn (116), obtained from Peganum harmala. Under physiological conditions (25 "C and pH 5-6), tetrahydroharman (117) can be produced in good yield from tryptamine (107) and acetaldehyde [19,24,101].…”

Section: Carboline Derivativesmentioning

confidence: 99%

The Biosynthesis of Alkaloids II

Mothes¹,

Schütte²

1963

Angew. Chem. Int. Ed. Engl.

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“…No caso de espécies de Aspidosperma, há predominantemente a ocorrência de alcalóides indólicos de considerável diversidade estrutural, muitos deles contendo esqueleto β-carbolínico simples, com sistemas tricíclicos de anéis pirido-indólicos 23 . A marcação isotópica de precursores indica que a parte indólica desses alcalóides é derivada biossinteticamente do triptofano e a parte não indólica, provavelmente de carboidratos, pela via chiquimato 24 . Segundo a literatura, alcalóides indólicos constituem bons marcadores quimiotaxonômicos para classificação botânica das espécies de Aspidosperma 10,[25][26][27] .…”

Section: Introductionunclassified

Alcalóides indólicos isolados de espécies do gênero Aspidosperma (Apocynaceae)

Pereira¹,

Jácome²,

Alcântara³

et al. 2007

Quím. Nova

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Recebido em 20/7/06; aceito em 11/9/06; publicado na web em 28/5/07 INDOLE ALKALOIDS FROM SPECIES OF THE Aspidosperma (Apocynaceae) GENUS. Species from genus Aspidosperma (Apocynaceae) are popularly employed to treat various diseases. This genus is characterized by the occurrence of indole alkaloids. Taking into account the various biological activities attributed to these alkaloids, the description of the chemical diversity in genus Aspidosperma is important. A review of simple carbolinic alkaloids isolated from species of various genera was published in 1979. In 1987, it was published another one dealing with the relationships between the chemical structures of the indole alkaloids and the evolution of Aspidosperma species. This work updates the information about the indole alkaloids isolated from Aspidosperma species.

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Biosynthesis of Indole Alkaloids. The Aspidosperma and Iboga Bases

Cited by 194 publications

References 1 publication

Enhanced metabolic process to indole alkaloids in Clematis terniflora DC. after exposure to high level of UV-B irradiation followed by the dark

Enhanced metabolic process to indole alkaloids in Clematis terniflora DC. after exposure to high level of UV-B irradiation followed by the dark

The Biosynthesis of Alkaloids II

Alcalóides indólicos isolados de espécies do gênero Aspidosperma (Apocynaceae)

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