An unusual indole alkaloid with anti-adenovirus and anti-HSV activities from Alstonia scholaris

Zhang, Li; Zhang, Chunjiang; Zhang, Dongbo; Wen, Juan; Zhao, Xiaowei; Li, Ya; Gao, Kun

doi:10.1016/j.tetlet.2014.01.122

Cited by 61 publications

(37 citation statements)

References 12 publications

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“…have recently isolated a novel alkaloid, 17‐nor‐excelsinidine from the twigs and leaves of Alstonia scholaris . Notably, this substance demonstrated in vitro significant inhibitory activity against HSV and adenovirus with EC50 values of 1.09 and 0.94 μg/ml and CC50 values of 6.97 and 3.32 μg/ml, respectively [81]. Berberine is an alkaloid extracted from Chinese herbal plant Coptidis rhizome and demonstrated in‐vitro antiherpetic activity with IC50 values for HSV‐1 and HSV‐2 24.4 and 26.8 μ m , respectively.…”

Section: Pure Compounds and Fractions That Possess Anti‐hsv Activitiesmentioning

confidence: 99%

Bioactive natural products with anti-herpes simplex virus properties

Hassan

Masarčíková

Berchová

2015

Journal of Pharmacy and Pharmacology

106

109

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Objectives In this review, we highlight and summarise the most promising extracts, fractions and pure compounds as potential anti-herpes simplex virus (HSV) agents derived from microorganisms, marine organisms, fungi, animals and plants. The role of natural products in the development of anti-HSV drugs will be discussed. Key findings Herpes simplex viruses (HSV-1 and -2) are common human pathogens that remain a serious threat to human health. In recent years, a great interest has been devoted to the search for integrated management of HSV infections. Acyclovir and related nucleoside analogues have been licensed for the therapy that target viral DNA polymerase. Although these drugs are currently effective against HSV infections, the intensive use of these drugs has led to the problem of drugresistant strains. Therefore, the search for new sources to develop new antiherpetic agents has gained major priority to overcome the problem. Summary Natural products as potential, new anti-HSV drugs provide several advantages such as reduced side effects, less resistance, low toxicity and various mechanisms of action. This paper aims to provide an overview of natural products that possess antiviral activity against HSV.

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Section: Pure Compounds and Fractions That Possess Anti‐hsv Activitiesmentioning

confidence: 99%

Bioactive natural products with anti-herpes simplex virus properties

Hassan

Masarčíková

Berchová

2015

Journal of Pharmacy and Pharmacology

106

109

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“…Indole alkaloids, which characteristically contain an indole nucleus, have pharmaceutical potential in a diverse range of applications, including as cytotoxic [1, 2], antiviral [3], anti-malarial [3], anti-inflammatory [4], and anti-cancer [5] agents. Although the indole nucleus is a nearly ubiquitous component of biologically active natural products, typically only low amounts of indole alkaloids are found in plants.…”

Section: Introductionmentioning

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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“…A water extract of the leaves has been developed into an over-the-counter drug in China [2]. A number of alkaloids, iridoids and terpenoids have been isolated from A. scholaris [3][4][5][6][7][8]. Among them, alkaloids are generally considered as the major bioactive compounds [2].…”

Section: Introductionmentioning

confidence: 99%