<i>Centaurea microcarpa</i> Coss. &amp; Dur. (Asteraceae) extracts: New cyanogenic glucoside and other constituents

Baatouche, S.; Cheriet, Thamere; Sarri, Djamel; Mekkiou, R.; Boumaza, Ouahiba; Benayache, Fadila; Brouard, Ignacio; León, Francisco; Seghiri, Ramdane

doi:10.1080/14786419.2018.1517343

Cited by 9 publications

(5 citation statements)

References 32 publications

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“…This study investigated the chemical constituents of 70% MeOH extract of the whole plants of P. aviculare yielded six flavonoid glycosides: avicularin (1) [15], juglanin (2) [16,17], myricitrin (3) [18], agetiin (6) [19,20], miquelianin (7) [21], and astragalin (8) [22]; Aviculin (4), one lignan [23] and 6-di-O-galloyl-β-D-glucopyranose (5), one galloyl glycoside [24]. Their chemical structures are shown in Fig.…”

Section: Resultsmentioning

confidence: 99%

Inhibition of DNA Topoisomerases I and II and Cytotoxicity of Compounds from Polygonum aviculare L .

Zheng

Piao

et al. 2021

Preprint

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Six flavonoid glycosides ( 1 – 3 , 6 – 8 ), one lignan ( 4 ), and one galloyl glycoside ( 5 ) were isolated based on the phytochemical study for the MeOH extract of Polygonum aviculare L. herb. The eight isolated compounds' structures were determined by comparing their physicochemical and spectral data with published ones. Compounds 5 and 6 were first isolated from this plant, and all the compounds were evaluated for DNA topoisomerase inhibitory activities and cytotoxicities. Among the purified compounds, 5 showed stronger inhibitory activity against topoisomerase I with an IC 50 value of 12.0 μM, while the value of positive control camptothecin (CPT) was 17.0 μM. For compounds 1 , 3 , and 5 – 8 , the value ranged from 0.054 to 17.0 µM, suggesting more potent inhibitory activity against topoisomerase II, and that of etoposide (VP-16) was 28.0 µM. Particularly, compounds 6 and 8 (IC 50 = 0.054 and 0.077 µM, respectively) inhibited Topo II about 500 times stronger than VP-16, making them safer agents of DNA topoisomerase. Furthermore, all compounds demonstrated no cytotoxic activity against four cancer cell lines. This study is the first to report the inhibition of DNA topoisomerases of compounds from P. aviculare , suggesting that these compounds may be potential candidates for treating cancer.

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Section: Resultsmentioning

confidence: 99%

Inhibition of DNA Topoisomerases I and II and Cytotoxicity of Compounds from Polygonum aviculare L .

Zheng

Piao

et al. 2021

Preprint

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“…59 Hedyotoside A was subject to evaluation for antiviral properties using the cytopathic effect reduction assay but showed no inhibitory activity (Asteraceae). 60 The cyanogenic glycoside 2-(β-D-glucopyranosyloxy)-2-(hydroxymethyl)butanenitrile, named as sachaloside V, 113 (Figure 12), alongside known cyanogens rhodiocyanoside A, lotaustralin, and heterodendrin, was isolated from the methanolic extract of the roots of Rhodiola sachalensis A. Bor. (Crassulaceae).…”

Section: Cyanogenic Glycosidesmentioning

confidence: 99%

Natural Products Containing the Nitrile Functional Group and Their Biological Activities

Scotti

Barlow²

2022

Natural Product Communications

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The importance of nitriles as a key class of chemicals with applications across the sciences is widely appreciated. The natural world is an underappreciated source of chemically diverse nitriles. With this in mind, this review describes novel nitrile-containing molecules isolated from natural sources from 1998 to 2021, as well as a discussion of the biological activity of these compounds. This study gathers 192 molecules from varied origins across the plant, animal, and microbial worlds. Their biological activity is extremely diverse, with many potential medicinal applications.

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“…Amygdalin (65) isolated from bitter almond in 1830 was the first cyanogenic glycoside with an aromatic aglycone to be reported [1]. The latest compound is a derivative of prunasin, prunasin methacrylate (71), reported in 2018 [3]. An experiment by Fischer in 1895 yielded a derivative compound of amygdalin and was named Fisher's glycoside [53].…”

Section: Group C: Cyanogenic Glycosides 54-108 Featuring An Aromatic Aglyconementioning

confidence: 99%

“…& Trab. (Asteraceae) in 2018 [3]. In total there are now 112 cyanogenic glycosides reported; 68 cyanogenic glycosides were reported before the year 2000 and 44 cyanogenic glycosides have been reported from 2000 until today.…”

Section: Introductionmentioning

confidence: 99%

Chemical Diversity of Plant Cyanogenic Glycosides: An Overview of Reported Natural Products

Yulvianti

Zidorn

2021

Molecules

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Cyanogenic glycosides are an important and widespread class of plant natural products, which are however structurally less diverse than many other classes of natural products. So far, 112 naturally occurring cyanogenic glycosides have been described in the phytochemical literature. Currently, these unique compounds have been reported from more than 2500 plant species. Natural cyanogenic glycosides show variations regarding both the aglycone and the sugar part of the molecules. The predominant sugar moiety is glucose but many substitution patterns of this glucose moiety exist in nature. Regarding the aglycone moiety, four different basic classes can be distinguished, aliphatic, cyclic, aromatic, and heterocyclic aglycones. Our overview covers all cyanogenic glycosides isolated from plants and includes 33 compounds with a non-cyclic aglycone, 20 cyclopentane derivatives, 55 natural products with an aromatic aglycone, and four dihydropyridone derivatives. In the following sections, we will provide an overview about the chemical diversity known so far and mention the first source from which the respective compounds had been isolated. This review will serve as a first reference for researchers trying to find new cyanogenic glycosides and highlights some gaps in the knowledge about the exact structures of already described compounds.

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Centaurea microcarpa Coss. & Dur. (Asteraceae) extracts: New cyanogenic glucoside and other constituents

Cited by 9 publications

References 32 publications

Inhibition of DNA Topoisomerases I and II and Cytotoxicity of Compounds from Polygonum aviculare L .

Inhibition of DNA Topoisomerases I and II and Cytotoxicity of Compounds from Polygonum aviculare L .

Natural Products Containing the Nitrile Functional Group and Their Biological Activities

Chemical Diversity of Plant Cyanogenic Glycosides: An Overview of Reported Natural Products

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