Foetithiophenes C-F, thiophene derivatives from the roots of Ferula foetida

Figures & data

Figure 1. The chemical structures of thiophene derivatives from F. foetida.

Table 1. ¹H NMR (500 MHz) and ¹³C NMR (125 MHz) spectroscopic data of compounds 3–6 (CDCl₃)^a.

	3		4		5		6
Position	δH	δC			δH	δC	δH	δC
2	–	129.5	–	127.9	–	119.3	–	71.8
3	–	134.8	–	136.3	–	137.9	3.36 q (7.5)	52.3
4	–	133.0	–	133.6	–	134.0	–	147.5
5	–	130.2	–	131.5	–	132.8	–	135.4
6	3.75 s	30.6	3.84 s	36.5	4.00 d (13.8) 4.18 d (13.8)	53.5	1.68 s	17.3
7	2.03 s	12.9	2.04 s	13.3	2.08 s	13.7	1.14 d (7.5)	12.9
8	1.97 s	12.4	1.98 s	12.8	1.99 s	12.8	1.71 s	14.1
9	2.28 s	13.2	2.28 s	13.5	2.29 s	13.4	2.08 s	12.2
10	2.07 s	15.2	–	–	2.48 s	37.6	2.13 s	12.7

^aCoupling constants are given in parentheses and reported in Hz; multiplicity is defined as follows: s, singlet; d, doublet; q, quartet; assignments were confirmed by HSQC, HMBC, and ROESY experiments.

^bSignals of two identical subunits. ¹³C NMR chemical shifts of compounds 3 and 4 were extracted from HSQC and HMBC spectra.

Table 2. The results of antimicrobial activities of the compounds from Ferula foetida roots.

	C. albicans		E. coli		B. cereus
Compound no.	MIC (µg/mL)	MBC (µg/mL)	MIC (µg/mL)	MBC (µg/mL)	MIC (µg/mL)	MBC (µg/mL)
1	INA	INA	INA	INA	INA	INA
2	INA	INA	INA	INA	200	INA
3	400	INA	INA	INA	100	INA
4	200	INA	400	INA	400	INA
5	400	INA	INA	INA	400	INA
6	400	INA	INA	INA	50	INA
Coniferaldehyde	200	INA	INA	INA	200	INA
Sinapic aldehyde	200	INA	INA	INA	400	INA
Gentamicin			10	10	10	10
Ketoconazole	25	50

INA donates inactive (MIC and MBC were >400 µg/mL).