Two new steroidal glycosides from Anemarrhena asphodeloides rhizome, and their cytotoxic activity in vitro

Background: This paper reports synthesis, cytotoxic activity, and apoptosis inducing effect of a novel series of styrylimidazo[1,2-a]pyridine derivatives. Objective: In this study, anti-cancer activity of novel styrylimidazo[1,2-a]pyridines was evaluated. Methods: Styrylimidazo[1,2-a]pyridine derivatives 4a-o were synthesized through a one-pot three-component reaction of 2-aminopyridines, cinnamaldehydes, and isocyanides in high yield. All synthesized compounds 4a-o were evaluated against breast cancer cell lines including MDA-MB-231, MCF-7, and T-47D using MTT assay. Apoptosis was evaluated by acridine orange/ethidium bromide staining, cell cycle analysis, and TUNEL assay as the mechanism of cell death. Results: Most of the synthesized compounds exhibited more potent cytotoxicity than standard drug, etoposide. Induction of apoptosis by the most cytotoxic compounds 4f, 4g, 4j, 4n, and 4m was confirmed through mentioned methods. Conclusion: In conclusion, these results confirmed the potency of styrylimidazo[1,2-a]pyridines for further drug discovery developments in the field of anti-cancer agents.

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In Vitro Cytotoxic Effects of Secondary Metabolites Present in Sarcopoterium Spinosum L.

Applied Sciences ◽

10.3390/app11115300 ◽

2021 ◽

Vol 11 (11) ◽

pp. 5300

Author(s):

Jozef Hudec ◽

Jan Mojzis ◽

Marta Habanova ◽

Jorge A. Saraiva ◽

Pavel Hradil ◽

...

Keyword(s):

Mammary Gland ◽

Ethyl Acetate ◽

Cytotoxic Activity ◽

Cell Lines ◽

Benzalkonium Chloride ◽

Ethanol Extract ◽

Cytotoxic Activities ◽

Sarcopoterium Spinosum ◽

Mcf 7

Sarcopoterium spinosum (L.) is a medicinal plant traditionally used for the treatment of various diseases including cancer in the Near- and Middle East. The fractions and constituents of the ethanol extract of S. spinosum were screened for in vitro cytotoxic activities on Jurkat (acute T-lymphoblastic leukemia), HeLa (cervical adenocarcinoma), MCF-7 (mammary gland adenocarcinoma), Caco-2 (human colorectal adenocarcinoma), and MDA-MB-231 (mammary gland adenocarcinoma) cell lines using the MTT (3-(dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. The ethanol extract was subsequently re-extracted with ethyl acetate and in its sub-fraction obtained by column chromatography three compounds (stachydrine, benzalkonium chloride and rutine) were the first time identified by nuclear magnetic resonance (NMR) analyses. The most active subfraction showed cytotoxic activity against HeLa, MCF-7, and Caco-2 cell lines. The three compounds mentioned, as standards of high-performance liquid chromatography (HPLC) quality, were studied individually and in combination. Cytotoxic activity observed might be due to the presence of benzalkonium chloride and rutin. Benzalkonium chloride showed the strongest growth suppression effect against HeLa cells (IC50 8.10−7 M) and MCF-7 cells (IC50 5.10−6 M). The mixture of stachydrine and benzalkonium chloride allowed a synergistic cytotoxic effect against all tested cancer and normal cells to be obtained. Anti-cancer activity of the plant extract of S. spinosum remains under-investigated, so this research describes how the three major compounds identified in the ethyl acetate extract can exert a significant dose dependent in vitro cytotoxicity.

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Steroidal Glycosides from Convallaria majalis Whole Plants and Their Cytotoxic Activity

International Journal of Molecular Sciences ◽

10.3390/ijms18112358 ◽

2017 ◽

Vol 18 (11) ◽

pp. 2358

Author(s):

Yukiko Matsuo ◽

Daisuke Shinoda ◽

Aina Nakamaru ◽

Kuni Kamohara ◽

Hiroshi Sakagami ◽

...

Keyword(s):

Cytotoxic Activity ◽

Steroidal Glycosides ◽

Convallaria Majalis ◽

Whole Plants

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Pimenta dioica and Pimenta racemosa: GC-based metabolomics for the assessment of seasonal and organs variation in their volatile components, in silico and in vitro cytotoxic activity estimation

Food & Function ◽

10.1039/d1fo00408e ◽

2021 ◽

Author(s):

Fadia S. Youssef ◽

Rola Labib ◽

A. Gad Haidy ◽

Safaa Eid ◽

Mohamed Lotfy Ashour ◽

...

Keyword(s):

Liquid Chromatography ◽

Cytotoxic Activity ◽

In Silico ◽

Volatile Components ◽

Gas Liquid Chromatography ◽

Four Seasons ◽

Pimenta Racemosa ◽

Pimenta Dioica ◽

Activity Estimation

Volatile constituents isolated from stems (S) and leaves (L) of Pimenta dioica (PD) and Pimenta racemosa (PR) during the four seasons were analyzed using GLC/FID (Gas liquid chromatography – flame...

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Ingol and Ingenol-Type Diterpenes from Euphorbia trigona Miller with Keratinocyte Inhibitory Activity

Plants ◽

10.3390/plants10061206 ◽

2021 ◽

Vol 10 (6) ◽

pp. 1206

Author(s):

Reham Hammadi ◽

Norbert Kúsz ◽

Csilla Zsuzsanna Dávid ◽

Zoltán Behány ◽

László Papp ◽

...

Keyword(s):

Liquid Chromatography ◽

Cytotoxic Activity ◽

Inhibitory Activity ◽

High Performance ◽

Skin Condition ◽

Positive Control ◽

Active Species ◽

The European Union ◽

Ingenol Mebutate

Ingenol mebutate, isolated from Euphorbia peplus, is an ingenane-type diterpenoid, primarily used for the topical treatment of actinic keratosis, a premalignant skin condition. The aim of our work was to investigate other Euphorbia species to find structurally similar diterpenes that can be used as alternatives to ingenol mebutate. Pharmacological investigation of Euphorbia candelabrum, Euphorbia cotinifolia, Euphorbia ramipressa, and Euphorbia trigona revealed the potent keratinocyte (HPV-Ker cell line) inhibitory activity of these spurge species. From the methanolic extract of the aerial parts of Euphorbia trigona Miller, the most active species, five ingol (1–5) and four ingenane-type diterpenoids (6–9) were isolated by various chromatographic separation techniques, including open column chromatography, vacuum liquid chromatography, thin-layer chromatography, and high-performance liquid chromatography. The structures of the compounds were determined by NMR spectroscopic analysis and by comparison of the assignations with the literature data. The cytotoxic activity of the compounds against keratinocytes was tested in vitro by using ingenol mebutate as a positive control. Among the isolated compounds, two ingenane derivatives (6 and 7) exhibited remarkably stronger cytotoxic activity (IC50 values 0.39 μM and 0.32 μM, respectively) on keratinocytes than ingenol mebutate (IC50 value 0.84 μM). These compounds could serve as starting materials for further investigations to find alternatives to Picato® (with active substance ingenol mebutate), which was withdrawn from marketing authorization in the European Union.

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Synthesis of New Simplified and Racemic Hemiasterlin Derivatives with Extremely High Cytotoxicity

Natural Product Communications ◽

10.1177/1934578x1801301225 ◽

2018 ◽

Vol 13 (12) ◽

pp. 1934578X1801301

Author(s):

Pham The Chinh ◽

Đang Thi Tuyet Anh ◽

Duong Huong Quynh ◽

Le Nhat Thuy Giang ◽

Nguyen Ha Thanh ◽

...

Keyword(s):

Cytotoxic Activity ◽

Cell Lines ◽

Human Cancer ◽

Microtubule Depolymerization ◽

Antimitotic Agent ◽

Human Cancer Cell Lines ◽

Weak Activity ◽

High Cytotoxicity ◽

Chemistry Community

Hemiasterlin is a potent antimitotic agent acting through inhibition of microtubule depolymerization. For this reason, the synthesis of new hemiasterlin derivatives has attracted a lot of interest in the organic chemistry community recently. In this paper, the synthesis and evaluation of the cytotoxicity of new simplified and racemic hemiasterlin derivatives were reported. All of the synthesized analogues were evaluated in vitro for cytotoxic activity against four human cell lines (KB, Hep-G2, LU and MCF7). Most of these analogues possess a strong cytotoxic activity on two human cancer cell lines (KB and Hep-G2) and very weak activity on LU and MCF7 cell lines.

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Anti-austeric Activity of Phenolic Constituents of Seeds of Arctium lappa

Natural Product Communications ◽

10.1177/1934578x1300800414 ◽

2013 ◽

Vol 8 (4) ◽

pp. 1934578X1300800 ◽

Cited By ~ 4

Author(s):

Yasuhiro Tezuka ◽

Keiichi Yamamoto ◽

Suresh Awale ◽

Feng Li ◽

Satoshi Yomoda ◽

...

Keyword(s):

Pancreatic Cancer ◽

Cytotoxic Activity ◽

Chlorogenic Acid ◽

Human Pancreatic Cancer ◽

Arctium Lappa ◽

Dicaffeoylquinic Acid ◽

Phenolic Constituents ◽

Pure Compounds ◽

F 14

From seeds of Arctium lappa L. (Asteraceae) we obtained arctigenin (1), arctiin (2), chlorogenic acid (3), 4,5-dicaffeoylquinic acid (4), 3,5-dicaffeoylquinic acid (5), 3,4-dicaffeoylquinic acid (6), matairesinol (11), isolappaol A (12), lappaol F (14), and lappaol B (15), together with 1:1 mixtures of isolappaol C (7) and lappaol C (8), arctignan E (9) and arctignan D (10), and 12 and lappaol A (13), while 3,3′,4′-tri- O-demethylarctigenin (16), 3,3′-di- O-demethyl-4′-dehydroxyarctigenin (17), and 3- O-demethylarctigenin (18) were obtained by anaerobic microbiological metabolism of 1. Then, we evaluated the in vitro preferential cytotoxic activity of these pure compounds and 1:1 mixtures, together with enterodiol (19) and enterolactone (20), against human pancreatic cancer PANC-1 cells in nutrient-deprived medium (NDM). Among them, 1 and 18 showed potent activity, with PC50 values of 1.75 and 4.38 μ M, respectively, while 11, 15, and 17 showed mild activity with PC50 values of 31.1, 30.9, and 38.7 μ/M, respectively. By comparing their structures and PC50 values, the following structural moieties could be concluded to be important for the preferential cytotoxicity of 1: 1) the 3-hydroxy-4-methoxyphenyl group at the 2-position on the γ-butyrolactone ring, 2) the less polar substituent at the 3-position on the γ-butyrolactone ring, and 3) the γ-butyrolactone ring.

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