Structure–activity relationships of saponins enhancing the cytotoxicity of ribosome-inactivating proteins type I (RIP-I)

Böttger, Stefan; Westhof, E.; Siems, Karsten; Melzig, Matthias F.

doi:10.1016/j.toxicon.2013.07.011

Cited by 24 publications

(29 citation statements)

References 22 publications

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“…Among 16 compounds, sinocrassulosides VI/VII, sinocrassulosides VIII/IX, and viscidulosides A/B, sharing common structural features of a CHO substituent at C-23 and a p -methoxycinnamoyl group of fucose residue at C-28 sugar chain (Figure 1), exhibited strong anticancer activity, while other compounds, either with a COOH not CHO substituent at C-23 or without p -methoxycinnamoyl at C-28 sugar chain, showed less or no cytotoxic activity. This finding is consistent with a previous study that the ideal anticancer saponins are of an oleanane type with the presence of sugar residues linked to the C-28 position [29]. Moreover, we found that the carboxyl group of the glucuronic acid at C-3 sugar chain could determine the cytotoxic activity of the three compounds.…”

Section: Discussionsupporting

confidence: 93%

Anticancer Effects of Sinocrassulosides VI/VII from Silene viscidula on HeLa Cells

Chen

et al. 2017

Evidence-Based Complementary and Alternative Medicine

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Natural products are becoming increasingly important in chemoprevention and for cancer therapy. Silene viscidula (S. viscidula), a traditional Chinese herb, has long been used as an anti-inflammatory and neuroleptic agent. However, the anticancer activity of S. viscidula has remained unclear. In this study, 16 compounds were extracted from S. viscidula. Among those compounds, sinocrassulosides VI/VII, an inseparable isomer mixture, possess the strongest inhibitory activity on HeLa cells with the IC 50 value of 2.37 M. Mechanism studies found that sinocrassulosides VI/VII downregulated the expression of cyclin D1 and decreased retinoblastoma (Rb) phosphorylation, which arrested HeLa cells in the G1 phase. Also, sinocrassulosides VI/VII could induce senescence via the upregulation of p16 and a significant increase of -galactosidase ( -gal) staining. Our results suggest that sinocrassulosides VI/VII may be a new therapeutic potential agent for cervical cancer. In addition, we explored the structure-activity relationships of three groups of the configurational isomer with similar chemical structure from S. viscidula. We first demonstrated that the length of the ester chains linked to the carboxyl group of the glucuronic acid residue could affect the potent cytotoxicity. This finding will open new avenues for developing effective anticancer compounds by modifying the components derived from plants in nature.

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Section: Discussionsupporting

confidence: 93%

Anticancer Effects of Sinocrassulosides VI/VII from Silene viscidula on HeLa Cells

Chen

et al. 2017

Evidence-Based Complementary and Alternative Medicine

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“…A valuable overview on the relation between structure and toxin enhancer ability of saponins was provided by Böttger et al [39]. They corroborated previous findings and added more detailed information on the required sugar composition (Figure 1).…”

Section: Glycosylated Triterpenoidsmentioning

confidence: 53%

Glycosylated Triterpenoids as Endosomal Escape Enhancers in Targeted Tumor Therapies

et al. 2017

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Protein-based targeted toxins play an increasingly important role in targeted tumor therapies. In spite of their high intrinsic toxicity, their efficacy in animal models is low. A major reason for this is the limited entry of the toxin into the cytosol of the target cell, which is required to mediate the fatal effect. Target receptor bound and internalized toxins are mostly either recycled back to the cell surface or lysosomally degraded. This might explain why no antibody-targeted protein toxin has been approved for tumor therapeutic applications by the authorities to date although more than 500 targeted toxins have been developed within the last decades. To overcome the problem of insufficient endosomal escape, a number of strategies that make use of diverse chemicals, cell-penetrating or fusogenic peptides, and light-induced techniques were designed to weaken the membrane integrity of endosomes. This review focuses on glycosylated triterpenoids as endosomal escape enhancers and throws light on their structure, the mechanism of action, and on their efficacy in cell culture and animal models. Obstacles, challenges, opportunities, and future prospects are discussed.

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“…They are mostly of plant origin and act as secondary plant metabolites. Due to their low toxicity, high biodegradability and high efficiency, saponins are a feasible alternative to synthetic surfactants . The saponins used in this study came from Sapindus mukorossi fruits, and were obtained using a Soxhlet extractor.…”

Section: Methodsmentioning

confidence: 99%

The ability of Achromobacter sp. KW1 strain to biodegrade isomers of chlorotoluene

Pacholak

Smułek

Jesionowski

et al. 2017

J of Chemical Tech & Biotech

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Background The isomers of chlorotoluene (2‐chlorotoluene, 3‐chlorotoluene and 4‐chlorotoluene) are considered to be toxic and to have a negative impact on humans and the environment. Therefore, issues related to their removal from the natural environment have become of increasing interest. Results The morphology of cells and colonies after long‐term metabolic stress was significantly modified. Metabolic stress is suggested to be a determinant of bacteria cell surface properties. The chlorine atom position in chlorotoluenes has a strong impact on cell surface modification. When the chlorine atom was at the ortho or para position, a large increase in hydrophobicity (from 40% to 73% and from 29% to 49%, respectively) and a decrease in the inner membrane permeability (from 0.31 to 0.24 µmol L−1 min−1 and from 0.52 to 0.13 µmol L−1 min−1) were observed. Moreover, Achromobacter sp. KW1 strain was found to exhibit good ability to degrade chlorotoluenes. The greatest difference in biodegradation between the stressed and non‐stressed strains was observed for the cultures grown on 4‐chlorotoluene and 3‐chlorotoluene. Conclusions Both long‐term contact with hydrocarbons and the addition of surfactants demonstrated a beneficial effect on the biodegradation process. However, as a result of long‐term contact with hydrocarbons, the bacteria studied were able to degrade chlorotoluenes faster and more effectively. © 2017 Society of Chemical Industry

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Structure–activity relationships of saponins enhancing the cytotoxicity of ribosome-inactivating proteins type I (RIP-I)

Cited by 24 publications

References 22 publications

Anticancer Effects of Sinocrassulosides VI/VII from Silene viscidula on HeLa Cells

Anticancer Effects of Sinocrassulosides VI/VII from Silene viscidula on HeLa Cells

Glycosylated Triterpenoids as Endosomal Escape Enhancers in Targeted Tumor Therapies

The ability of Achromobacter sp. KW1 strain to biodegrade isomers of chlorotoluene

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