Cancer Preventive Agents. Part 6: Chemopreventive Potential of Furanocoumarins and Related Compounds

Figures & data

Scheme 1 Synthetic routes to furanocoumarins and related compounds (i) chloroacetaldehyde, potassium carbonate; (ii) 2 N hydrochloric acid, water, 50°C; (iii) chloroacetone, potassium carbonate, acetone; (iv) polyphosphoric acid, 110°C.

Table 1 Relative ratio^a. of Epstein-Barr virus early antigen (EBV-EA) activation with respect to positive control (100%) in presence of furanocoumarin and analogues.

	Concentration (mol ratio/TPA)^b.
Compound	1000	500	100	10
2a	5.2 ± 0.4 (60)^c.	38.9 ± 1.4 (>80)	68.2 ± 2.1 (>80)	91.4 ± 0.7 (>80)
2b	12.7 ± 0.4 (60)	50.6 ± 1.7 (>80)	80.2 ± 2.5 (>80)	100 ± 0.3 (>80)
2c	15.5 ± 1.0 (70)	53.2 ± 1.7 (>80)	81.4 ± 2.4 (>80)	100 ± 0.2 (>80)
2d	6.1 ± 0.7 (60)	40.2 ± 1.5 (>80)	70.5 ± 2.1 (>80)	92.5 ± 0.3 (>80)
2e	16.7 ± 0.9 (60)	57.5 ± 1.9 (>80)	86.4 ± 2.4 (>80)	100 ± 0.2 (>80)
2f	10.2 ± 0.5 (60)	50.7 ± 1.7 (>80)	78.1 ± 2.0 (>80)	96.5 ± 0.5 (>80)
2g	9.8 ± 0.3 (60)	46.2 ± 1.4 (>80)	74.0 ± 2.4 (>80)	94.2 ± 0.5 (>80)
3a	3.9 ± 0.3 (60)	36.0 ± 1.3 (>80)	66.4 ± 2.1 (>80)	88.6 ± 0.5 (>80)
3b	9.2 ± 0.4 (60)	45.8 ± 1.4 (>80)	73.3 ± 2.0 (>80)	94.1 ± 0.4 (>80)
3c	10.5 ± 0.7 (60)	50.0 ± 1.6 (>80)	78.2 ± 2.3 (>80)	96.7 ± 0.4 (>80)
3d	4.7 ± 0.5 (60)	38.9 ± 1.2 (>80)	69.8 ± 1.9 (>80)	90.7 ± 0.9 (>80)
3e	8.4 ± 0.5 (60)	41.1 ± 1.3 (>80)	72.3 ± 2.1 (>80)	92.7 ± 0.5 (>80)
3f	8.6 ± 0.5 (60)	42.7 ± 1.2 (>80)	73.8 ± 2.4 (>80)	93.5 ± 0.7 (>80)
3g	9.5 ± 0.5 (60)	46.0 ± 1.3 (>80)	73.9 ± 2.1 (>80)	94.4 ± 0.4 (>80)
4a	13.9 + 0.8 (60)	47.3 + 1.6 (>80)	78.6 + 2.4 (>80)	97.7 ± 0.7 (>80)
4b	6.8 + 0.4 (60)	42.1 + 1.5 (>80)	71.9 + 2.5 (>80)	93.0 ± 0.6 (>80)
4c	14.8 + 0.5 (60)	55.2 + 1.8 (>80)	84.7 + 2.0 (>80)	100 ± 0.2 (>80)
4d	15.9 + 0.6 (60)	54.6 + 1.6 (>80)	83.2 + 2.5 (>80)	100 ± 0.4 (>80)
4e	15.2 + 0.7 (70)	55.7 + 1.7 (>80)	84.2 + 2.5 (>80)	100 ± 0.3 (>80)
4f	11.3 + 0.7 (60)	50.9 + 1.6 (>80)	79.2 + 2.5 (>80)	100 ± 0.3 (>80)
4g	18.3 + 0.9 (70)	59.8 + 1.7 (>80)	87.9 + 2.7 (>80)	100 ± 0.2 (>80)
5a	4.0 ± 0.3 (70)	36.0 ± 1.3 (>80)	67.3 ± 1.9 (>80)	89.3 ± 0.5 (>80)
5b	7.1 ± 0.7 (60)	45.1 ± 1.5 (>80)	72.5 ± 2.3 (>80)	94.0 ± 0.5 (>80)
5c	13.9 ± 0.5 (60)	53.2 ± 1.8 (>80)	81.4 ± 2.4 (>80)	100 ± 0.3 (>80)
5d	10.4 ± 0.5 (70)	48.1 ± 1.5 (>80)	77.9 ± 2.3 (>80)	95.0 ± 0.5 (>80)
5e	14.8 ± 0.5 (70)	53.8 ± 1.5 (>80)	82.0 ± 2.6 (>80)	100 ± 0.3 (>80)
5f	4.7 ± 0.4 (60)	36.3 ± 1.4 (>80)	66.2 ± 1.8 (>80)	89.0 ± 0.3 (>80)
5g	15.7 ± 0.6 (60)	56.4 ± 1.8 (>80)	84.9 ± 2.0 (>80)	100 ± 0.3 (>80)
Curcumin^d.	0.0 ± 0.5 (60)	22.8 ± 1.8 (>80)	81.7 ± 1.9 (>80)	100 ± 0.2 (>80)

^a.Values represent percentages relative to the positive control value (100%).

^b.TPA concentration is 20 ng/ml (32 pmol/ml).

^c.Values in parentheses are viability percentages of Raji cells.

^d.Balasubramanian et al. (1997).

Figure 1 Inhibition of TPA-induced tumor promotion by multiple applications of furanocoumarins 5a and 3a. All mice were carcinogenically initiated with DMBA and promoted with 1.7 nmol of TPA given twice weekly starting 1 week after initiation. (A) Percentage of mice bearing papillomas; (B) average number of papillomas per mouse. At 20 weeks of promotion, groups II, III, and IV were different from group I (p < 0.05) in numbers of papillomas per mouse.

Balasubramanian V, Kapadia GJ, Tokuda H, Takayyasu J, Konoshima T, Takasaki M, Nishino H (1997): Abstract of the 38th Annual Meeting of the American Society of Pharmacognosy, Iowa City, IA, USA, July 27, poster 82.

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