Sesquiterpene coumarins from the fruits of Ferula badrakema

Figures & data

Figure 1.  Chemical structures of sesquiterpene coumarins isolated from Ferula badrakema fruits.

Table 1.  ¹H-NMR data obtained with compounds 1-5 (600 MHz, δ ppm).

Position of proton	1 (J)	2 (J)	3 (J)	4 (J)	5 (J)
2	-	-	-	-	-
3	6.28 d (9.6)	6.27 d (9.5)	6.27 d (9.5)	6.30 d (9.5)	6.25 d (9.5)
4	7.66 d (9.6)	7.66 d (9.5)	7.66 d (9.5)	7.67 d (9.5)	7.65 d (9.5)
5	7.39 d (8.4)	7.38 d (8.4)	7.39 d (8.4)	7.39 d (8.4)	7.39 d (8.4)
6	6.86 dd (8.4, 2.3)	6.86 dd (8.4, 2.3)	6.88 dd (8.4, 2.3)	6.87 dd (8.4, 1.8)	6.83 d (8.4)
7	-	-	-	-	-
8	6.85 d (2.3)	6.85 d (2.3)	6.85 d (2.3)	6.86 d (1.8)	6.82 brs
9	-	-	-	-	-
10	-	-	-	-	-
1′	1.66 dd^* β 2.30 m α	1.75 m^* β 2.01 m^* α	1.37 dd (13.2, 4.2) β 2.05 m^* α	1.68 m β 2.01 m α	1.55 ddd (15.0, 6.0, 6.0) β 1.97 dt (15.0, 4.2) α
2′	2.31 m β 2.75 ddd (15.3, 6.6) α	1.69 m	1.67 m	1.70 m β 2.00 m α	1.69 m
3′	-	3.52 brs	3.31 brd (10.8)	3.41 brs	3.23 dd (10.8, 4.2)
4′	-	-	-	-	-
5′	1.68 dd^*	1.73 dd^*	1.30 dd (11.4, 6.0)	2. 67 s	2. 16 s
6′	2.00 like brd β 2.18 like brt α	2.0 m^*	2.01 m^*	-	-
7′	5.62 brs	5.59 brs	5.60 brs	5.93 brs	5.89 s
8′	-	-	-	-	-
9′	2.28^*	2.37 brs	2.26 brs	2.81 brs	2.66 brs
10′	-	-	-	-	-
11′	a 4.10 dd (9.80, 5.20) b 4.21 dd (9.80, 4.80)	a 4.04 dd (9.60, 6.00) b 4.20 dd (9.60, 3.30)	a 4.03 dd (9.60, 5.40) b 4.19 dd (9.60, 3.00)	a 4.18 dd (10.20, 5.40) b 4.29 dd (10.20, 3.00)	a 4.14 dd (9.60, 5.40) b 4.25 dd (9.60, 3.00)
12′	1.75 s	1.73 s	1.73 s	1.99 s	1.95 s
13′	1.17 s	1.02 s	1.05 s	1.23 s	1.17 s
14′	1.13 s	0.97 s	0.93 s	1.26 s	1.27 s
15′	1.18 s	0.96 s	0.95 s	1.07 s	1.02 s

^*Overlapped with other signals.

Table 2.  ¹³C-NMR data obtained with compounds 1-5 (125.7 MHz, δ ppm).

Position of carbon	1	2	3	4	5
2	161.5	161.6	161.6	160.6	160.9
3	113.4	113.4	113.4	112.9	113.3
4	143.7	143.8	143.8	142.9	143.3
5	129.2	129.1	129.1	128.9	128.8
6	113.6	113.5	113.5	112.8	112.6
7	162.2	162.5	162.4	161.1	161.2
8	101.7	101.7	101.7	101.5	101.1
9	156.3	156.3	156.3	155.3	155.6
10	113.0	112.8	112.9	112.7	112.7
1′	38.8	32.2	38.2	31.1	37.3
2′	34.8	25.2	27.7	24.4	26.0
3′	216.4	76.2	79.2	76.1	78.5
4′	47.9	37.6	39.1	36.3	37.6
5′	51.5	43.8	49.7	57.1	62.0
6′	24.3	23.6	23.7	199.8	198.4
7′	124.0	124.2	124.1	129.6	129.5
8′	132.7	132.9	132.7	155.3	155.5
9′	53.4	53.9	54.2	54.8	54.7
10′	36.2	36.0	36.2	41.6	41.9
11′	67.0	67.5	67.4	65.9	65.3
12′	25.6	22.1	22.0	21.6	21.3
13′	22.7	28.5	28.4	21.4	14.8
14′	25.6	22.7	15.3	28.1	28.2
15′	14.9	15.2	15.2	16.1	15.5