TABLE 2

¹H and ¹³C NMR spectroscopic data of [6]-shogaol, M10, M12, and synthetic 5-N-acetylcysteinyl-[6]-shogaol

No.	[6]-Shogaol^{^a}		M10^{^b}		M12^{^b}		5-N-acetylcysteinyl-[6]-shogaol^{^a}
No.	δ_H multi (J in Hz)	δ_C	δ_H multi (J in Hz)	δ_C	δ_H multi (J in Hz)	δ_C	δ_H multi (J in Hz)	δ_C
1′		132.6		132.9		134.0		134.0
2′	6.80 d (1.8)	111.8	6.71 d (1.5)	111.0	6.73 d (2.2)	111.0	6.81 d (1.8)	111.7
3′		147.6		146.4		146.4		149.0
4′		144.5		143.9		143.7		145.9
5′	6.71 d (8.0)	114.7	6.84 d (8.0)	114.3	6.84 d (7.9)	114.2	6.71 d (8.0)	114.6
6′	6.63 dd (8.0, 1.8)	120.4	6.69 dd (8.0, 1.5)	120.8	6.71 dd (7.9, 2.2)	120.9	6.65 dd (8.0, 1.8)	120.2
1	2.88 m	31.1	2.86 t (7.5)	29.3	2.64 m; 2.75 m	31.7	2.80 m	27.5
2	2.66 m	41.3	2.75 m	45.5	1.79 m; 1.74 m	39.8	2.74 dd (17.1, 6.3); 2.67 dd (17.1, 6.3)	49.7
3		201.5		208.4	4.00 m	68.9		211.2
4	6.12 br d (15.9)	130.0	2.59 dd (16.6, 6.5); 2.69 dd (16.6, 6.5)	48.5	1.71 m; 1.62 m	40.6	2.74 m	46.1
5	6.90 dt (15.9, 7.02)	148.7	3.04 m	41.6	2.75 m	43.2	3.14 m	42.6
6	2.22 m	32.1	1.50 m	34.4	1.61m	34.8	1.51 m	33.7
7	1.48 m	27.6	1.42 m; 1.38 m	26.5	1.44 m	26.6	1.34 m	26.6
8	1.34 m	29.8	1.27 m	31.6	1.31 m	31.9	1.27 m	30.9
9	1.34 m	22.1	1.31 m	22.6	1.31 m	22.6	1.33 m	22.2
10	0.93 t (7.1)	13.0	0.90 t (7.1)	14.0	0.91 t (7.1)	14.1	0.92	14.4
3′-OMe	3.84 s		3.89 s	55.9	3.90 s	55.7		56.4
5-SMe			2.04 s	13.3	2.05	12.3
4′-OH			5.45 s		5.47 s
3-OH					2.25 d (4.9)
1′′							3.00 dd (4.7, 13.7); 2.92 dd (7.1, 13.7)	30.4
2′′							4.58 dd (7.1, 4.7)	54.6
3′′								173.1
4′′								173.1
5′′							2.01 s	22.6

↵a Data were measured in CD₃OD at 600 (¹H) and 150 MHz (¹³C).
↵b Data were measured in CDCl₃ at 600 (¹H) and 150 MHz (¹³C). Chemical shifts (δ) are in ppm being relative to CD₃OD and CDCl₃.