Novel anticancer alkene lactone from Persea americana

Figures & data

Table 1. ¹H- and ¹³C-NMR data for compound 1^a.

	^13C-NMR	Multiplicities	^1H-NMR
Position
2	166.9	C	–
3	127.3	C	–
4	66.2	CH	5.00 (dd, J = 2.8, 1.7)
5	157.6	C	–
6	91.3	CH2	4.49 br, s 4.7(dd, J = 2.8, 1.4)
7	150.1	CH	6.85 (dt J = 8.0, 2.1)
8	31.8	CH2	2.18 m
9	29.6	CH2	1.26 m
10	29.6	CH2	1.26 m
11	29.5	CH2	1.26 m
12	29.4	CH2	1.26 m
13	29.3	CH2	1.26 m
14	29.3	CH2	1.26 m
15	28.2	CH2	1.26 m
16	22.6	CH2	1.26 m
17	14.1	CH3	0.75 s
OH			2.68 br s

^aSolvent CDCl₃; chemical shifts (ppm) from TMS or CHCl₃; J values (Hz).

Figure 1. Proliferation and apoptotic alterations of MCF-7 breast cancer cells and non-tumorigenic MCF-12A mammary epithelial cells after 48 h incubation with different concentrations (0.01, 0.1, 1, 10 µg/mL) of compound 1 and 0.1% DMSO as negative control substance. Both measurements were determined by flow cytometry. Proliferation phase was the sum of the G2/M and S phase. Apoptotic cells were calculated from the sub-G1 phase. Negative control treatment with DMSO was set to 100%. n = 3, means ± SD, statistical significance was determined by the unpaired t-test (***p < 0.001).

Figure 2. Online monitoring of adhesion and acidification rates of the MCF-7 breast cancer cell line in comparison with the non-tumorigenic epithelial cell line MCF-12 A under treatment with compound 1 (final concentration 0.1 μg/mL) using the Bionas® 2500 analyzing system. Gray shadowed area marks the adaption phase (4 h) of the cells to the new conditions in pure running medium. Treatment with compound 1 was carried out for 20 h at a flow rate of 56 μL/min with 4/4 min pump/stop phases. The percentage of the standardized and normalized rates of cell adhesion and extracellular acidification in a period of 24 h are displayed. The averages of three individual experiments are shown.

Figure 3. Integrin (β1, β3; α2–α6, αv) and HA receptor expression of MCF-7 and MCF-12A cells after treatment with 0.1 and 1 µg/mL with compound 1 for 48 h measured by flow cytometry. Graphs presenting the relative expression rates normalized to the control measurements with DMSO as negative control. Controls were set to 100% which is represented by 1 in the graph meaning that values below 1 show a reduction of the receptor expression and an increase in the values above 1. The mean values of the measurements refer to the tables below. n = 3, means, statistical significance was determined by the unpaired t-test (*p < 0.05, **p < 0.005, and ***p < 0.001).

Figure 4. Calculation of the IC₅₀ value of compound 1 on MCF-7 breast cancer cells by MTS tests.