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. 2023 Jan 1;28(1):360.
doi: 10.3390/molecules28010360.

Chemical Evaluation of Liquidambar styraciflua L. Fruits Extracts and Their Potential as Anticancer Drugs

Rafaela G Pozzobon  1   2 , Renata Rutckeviski  1   2 , Juliane Carlotto  3 , Vanessa S Schneider  3 , Lucimara M C Cordeiro  3 , Graziele Francine Franco Mancarz  2 , Lauro M de Souza  1   2 , Rosiane Guetter Mello  1   2 , Fhernanda Ribeiro Smiderle  1   2
Affiliations

Chemical Evaluation of Liquidambar styraciflua L. Fruits Extracts and Their Potential as Anticancer Drugs

Rafaela G Pozzobon et al. Molecules. .

Abstract

Liquidambar styraciflua L. is an aromatic species, popularly used in traditional Chinese medicine to treat diarrhea, dysentery, coughs, and skin sores. The present study was designed to investigate the chemical composition and biological potential of extracts obtained from the fruits of this plant. For the chemical evaluation, it was used mainly liquid and gas chromatography, plus NMR, and colorimetric methods. The aqueous extract (EA) originated two other fractions: an aqueous (P-EA) and an ethanolic (S-EA). The three extracts were composed of proteins, phenolic compounds, and carbohydrates in different proportions. The analyses showed that the polysaccharide extract (P-EA) contained pectic polysaccharides, such as acetylated and methyl esterified homogalacturonans together with arabinogalactan, while the fraction S-EA presented phenolic acids and terpenes such as gallic acid, protocathecuic acid, liquidambaric acid, combretastatin, and atractyloside A. EA, P-EA, and S-EA showed antioxidant activity, with IC50 values of 4.64 µg/mL, 16.45 µg/mL, and 3.67 µg/mL, respectively. The cytotoxicity followed the sequence S-EA > EA > P-EA, demonstrating that the toxic compounds were separated from the non-toxic ones by ethanol precipitation. While the fraction S-EA is very toxic to any cell line, the fraction P-EA is a promising candidate for studies against cancer due to its high toxicity to tumoral cells and low toxicity to normal cells.

Keywords: Liquidambar styraciflua; antioxidant activity; antitumoral activity.

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Conflict of interest statement

The authors declare no conflict of interests.

Figures

Figure 1
Figure 1
HPSEC elution profile of fraction P-EA. Refractive index detector. Elution volume of dextran standards of molecular weight 72.2 kDa, 40.2 kDa, 17.2 kDa, 9.4 kDa, and 5 kDa (left to right) were employed to construct the calibration curve.
Figure 2
Figure 2
HSQC-DEPT correlation map of P-EA fraction in D2O at 70 °C, the chemical shifts are expressed as δ (ppm). Inverted signals in DEPT experiment are marked with *.
Figure 3
Figure 3
Chromatographic profile of S-EA fraction obtained on LC-MS analysis.
Figure 4
Figure 4
Analysis of the antioxidant effect of L. styraciflua fruits extracts on DPPH radical scavenging. Aqueous (EA) (A), polysaccharide (P-EA) (B), and Low Mw (S-EA) (C) extracts were tested at 1–100 µg/mL or 0: negative control (vehicle). AA: positive control (ascorbic acid, 50 µg/mL). Statistical analyses were performed by unpaired t-test. Results represent the median of three independent experiments (n = 4) and * p < 0.05; ** p < 0.01; *** p < 0.001.
Figure 5
Figure 5
Cell viability of HepG2 cell line treated with EA (A,D), P-EA (B,E), and S-EA (C,F). Cells were incubated with the extracts (1, 3, 10, 30, 100, 300, or 1000 µg/mL) for 24 h and 48 h. Statistical analyses were performed by unpaired t-test. The results represent the median of two independent experiments (n = 4). ** p < 0.01; *** p < 0.001 compared to vehicle group (control group).
Figure 6
Figure 6
Cell viability determined by MTT assay of MCF7 cell line treated with EA (A,D,G), P-EA (B,E,H), and S-EA (C,F,I). Cells were incubated with the extracts (1, 3, 10, 30, 100, 300, or 1000 µg/mL) for 24 h and 48 h, and 300, 500, 750, or 1000 µg/mL for 72 h. Statistical analyses were performed by unpaired t-test. The results represent the median of three independent experiments (n = 3–6). * p < 0.05; ** p < 0.01; *** p < 0.001 compared to vehicle group (control group). # p < 0.05; ## p < 0.01; ### p < 0.001 comparison with indicated pairs.
Figure 7
Figure 7
Cell viability determined by MTT assay of MCF10A cell line treated with EA (A,D,G), P-EA (B,E,H), and S-EA (C,F,I). Cells were incubated with the extracts (1, 3, 10, 30, 100, 300, or 1000 µg/mL) for 24 h and 48 h, and 300, 500, 750, or 1000 µg/mL for 72 h. Statistical analyses were performed by unpaired t-test. The results represent the median of three independent experiments (n = 3–6). * p < 0.05; ** p < 0.01; *** p < 0.001 compared to vehicle group (control group). # p < 0.05; ## p < 0.01; ### p < 0.001 comparison with indicated pairs.
Figure 8
Figure 8
Analysis of the cell cycle progression of MCF7 cells after incubation with P-EA fraction (A) and S-EA fraction (B), and apoptosis induction after incubating with S-EA (C), using flow cytometry. For cell cycle, the cells were treated with P-EA (500, 750 or 1000 µg/mL) and S-EA (100 or 300 µg/mL) for 72 h. For analysis of apoptosis, the cells were treated with S-EA (500, 750 or 1000 µg/mL) for 72 h. Statistical analyses were performed by unpaired t-tests. The results represent the mean ± SD of two independent experiments (n = 3). * p < 0.05; ** p < 0.01; *** p < 0.001 compared to vehicle group (control group).
Figure 9
Figure 9
Schematic representation of the L. styraciflua fruits extraction.
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