. 2023 May 26;16(6):792. doi: 10.3390/ph16060792

Table 2.

¹ H-NMR (500 MHz) and ¹³C-NMR (125 MHz) data of compounds 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, and 15 (in CDCl₃, δ in ppm, J in Hz).

Position	Conferone (1)		Conferol (2)		Feselol (3)		Badrakemone (4)
Position	¹H-NMR	¹³C-NMR	¹H-NMR	¹³C-NMR	¹H-NMR	¹³C-NMR	¹H-NMR	¹³C-NMR
2	-	161.1	-	161.3	-	161.5	-	161.5
3	6.25; d; 9.5; 1H	113.1	6.23; d; 9.5; 1H	113.1	6.25; d; 9.4; 1H	113.2	6.25; d; 9,5; 1H	113.2
4	7.64; d; 9.5; 1H	143.4	7.63; d; 9.5; 1H	143.5	7.63; d; 9.4; 1H	143.5	7.62; d; 9.5; 1H	143.6
5	7.37; d; 8.6; 1H	128.7	7.35; d; 8.5; 1H	128.9	7.36; d; 8.5; 1H	128.9	7.36; d; 8.7; 1H	129
6	6.83; dd; 2.4; 8.6; 1H	113	6.83; dd; 2.4, 8.5; 1H	113.3	6.82; dd; 2.3; 8.5; 1H	113.3	6.82; dd; 2.4; 8.7; 1H	113.3
7	-	161.7	-	162.3	-	162.2	-	162.2
8	6.8; d; 2.4; 1H	101.2	6.81; d; 2.5; 1H	101.5	6.8; d; 2.3; 1H	101.4	6.81; d; 2.4; 1H	101.4
9	-	156	-	156.1	-	156.2	-	156.1
10	-	112.7	-	112.6	-	112.6	-	112.7
1′α	2.28; m; 1H *	38.5	1.68; m; 2H *	31.9	2.01; dt; 3.6, 9.8; 1H	37.9	2.09; ddd; 3.5; 6.3; 13.3; 1H	37.8
1′β	1.62; td; 4.2; 13.3; 1H	38.5	1.68; m; 2H *	31.9	1.33; td; 4.3;13.2; 1H	37.9	1.81; td; 5.4; 13.3; 1H	37.8
2′ α	2.75; td; 5.4; 14.6; 1H	34.4	1.96; m; 1H **	25.3	1.65; m; 2H	27.4	2.68; tdd; 6.2; 13.2; 15.3; 1H	34.7
2′β	2.28; m; 1H *	34.4	1.65; m; 1H *	25.3	1.65; m; 2H	27.4	2.41; ddd; 3.4; 5.3; 15.3; 1H	34.7
3′	-	216.1	3.47; bt; 2.4; 1H	75.9	3.28; dd; 4.3; 11.4; 1H	79.2	-	216.2
4′	-	47.6	-	35.7	-	38.8	-	48.1
5′	1.68; dd; 4.4; 12.2; 1H	51.1	1.70; m; 1H *	43.5	1.28; dd; 5.2; 11.7; 1H	49.5	1.66; dd; 2.7; 12.5; 1H	55.2
6′α	2.13; dddd; 2.6; 4.8; 9.5; 19.4; 1H	23.9	1.96; m; 2H **	23.3	2.05; m; 2H *	23.4	1.57; dt; 6.8; 12.5; 1H	24.6
6′β	1.99; dt; 5.6; 17.3; 2H	23.9	1.96; m; 2H **	23.3	2.05; m; 2H *	23.4	1.68; dp; 2.5; 12.4; 1H	24.6
7′α	5.6; dq; 1.9; 5.8; 1H	123.9	5.54; bs; 1H	124	5.56; brs; 1H	123.9	2.15; td; 3.4; 13.3; 1H	37.2
7′β	-	123.9	-	124	-	123.9	2.5; ddd; 2.5; 4.2; 13.3; 1H	37.2
8′	-	132.5	-	132.6	-	132.4	-	145.8
9′	2.28; m; 1H *	53.1	2.32; bs; 1H	53.7	2.23; brs; 1H	53.9	2.3; t; 5.9; 1H	54.2
10′	-	35.9	-	37.4	-	35.9	-	38.8
11′a	4.07; dd; 5.3; 9.8; 1H	66.7	4.02; dd; 5.8, 9.4; 1H	67.2	4.01; dd; 5.9; 9.7; 1H	67.2	4.22; m; 2H	65.8
11′b	4.17; dd; 3.4; 9.8; 1H	66.7	4.17; dd; 3.3, 9.4; 1H	67.2	4.17; dd; 3.4; 9.7; 1H	67.2	4.22; m; 2H	65.8
12′a	1.7; brt; 3H	21.5	1.69; bs; 3H *	21.9	1.68; d; 3.8; 3H	21.8	4.59; brs; 1H	108.9
12′b	1.7; brt; 3H	21.5	1.69; bs; 3H *	21.9	1.68; d; 3.8; 3H	21.8	4.98; brs; 1H	108.9
13′	1.08, s; 3H	25.2	0.93; s; 3H	22.5	1.02; s; 3H	28.2	1.13; s; 3H	26
14′	1.12; s; 3H	22.3	0.96; s; 3H	28.2	0.9; s; 3H	15.4	1.06; s; 3H	22.1
15′	1.13; s; 3H	14.5	0.91; s; 3H	14.9	0.88; s; 3H	15	1.04; s; 3H	15
Position	Mogoltadone (5)		Farnesiferol A (6)		Farnesiferol A acetate (7)		Gummosin (8)
Position	¹H-NMR	¹³C-NMR	¹H-NMR	¹³C-NMR	¹H-NMR	¹³C-NMR	¹H-NMR	¹³C-NMR
2	-	161.2	-	161.9	-	161.3	-	161.5
3	6.24; d; 9.5; 1H	113	6.25; d; 9.5; 1H	113.1	6.25; d; 9.4	113.1	6.22; d; 9.5; 1H	112.9
4	7.62; d; 9.5; 1H	143.4	7.63; d; 9.5; 1H	143.5	7.63; d; 9.4; 1H	143.6	7.6; d; 9.5; 1H	143.6
5	7.35; d; 8.5; 1H	128.7	7.35; d; 8.6; 1H	128.7	7.36; d; 8.3; 1H	128.9	7.32; d; 9.3; 1H	128.7
6	6.78; dd; 2.5; 8.5; 1H	113	6.81; dd; 2.4; 8.6; 1H	113.4	6.8; dd; 2.1; 8.3; 1H	113.2	6;81; dd; 2.4; 9.3; 1H	113.3
7	-	161.7	-	161.9	-	161.9	-	162.3
8	6.77; d; 2.5; 1H	101.4	6.8; d; 2.4; 1H	101.7	6.79; d; 2.1; 1H	101.9	6.75; d; 2.4; 1H	101.8
9	-	155.7	-	155.9	-	155.9	-	155.9
10	-	112.6	-	112.6	-	112.6	-	112.5
1′α	1.91; td; 4.5; 13.6; 1H	35.5	1.37; dt; 3.2; 13.0; 1H	35	1.73; 2H **	24.1	1.99; tdd; 2.2; 3.3; 13.9; 1H	25.7
1′β	1.69; ddd; 2.8; 5.9; 13.6; 1H	35.5	1.63; td; 5.6; 12.0; 1H	35	1.73; 2H **	24.1	1.62; dq; 3.1; 13.9; 1H
2′ α	2.76; td; 5.7; 14.7; 1H	35.1	1.7; qd; 2.5; 12.5; 2H	27.7	1.39; 1H *	34.5	1.03; dt; 3.1; 12.5; 1H	29.3
2′β	2.36; m; 1H *	35.1	1.7; qd; 2.5; 12.5; 2H	27.7	1.72; 1H **	34.5	2.05; dd; 2.1; 13.2; 1H
3′	-	216.2	3.25; dd; 5.2; 10.2; 1H	79.2	4.5; dd; 6.3; 8.5; 1H	80.9	3.45; dd; 2.1; 3.5; 1H	76.2
4′	-	47.8	-	39.2	-	38.1	-	37.7
5′	1.54; qd; 4.4; 13.03; 1H	47.6	1.31; dd; 2.8; 12.6; 1H	46.6	1.41; m; 1H *	46.7	1.77; dd; 3.1; 12.9; 1H	40.8
6′ α	1.78; dd; 3.15; 12.6; 1H	23.8	1.73; dq; 2.8; 10.5; 1H	23.1	1.7; m; 2H **	23	1.60; dq; 2.8; 13.8; 1H	23.1
6′ β	1.64; m; 1H *	23.8	1.43; qd; 4.4; 12.9; 1H	23.1	1.7; m; 2H **	23	1.37; qd; 4.2; 13.0; 1H
7′α	2.1; td; 4.8; 13.6; 1H	32	2.04; td; 5.1; 13.5; 1H	32.5	2.05; m; 1H ***	32.4	2.09; tdt; 2.3; 6.6; 14.1; 1H	32.7
7′β	2.39; dt; 3.27; 13.6; 1H	32	2.33; dt; 3.1; 12.4; 1H	32.5	2.35; dd; 3.9; 14.1; 1H	32.4	2.31; ddt; 1.8; 4.0; 14.1; 1H
8′	-	146	-	146.8	-	146.6	-	147.1
9′	2.35; m; 1H *	56	2.21; t; 6.1; 1H	56.7	2.21; t; 6.0; 1H	56.7	2.18; brt; 6.2; 1H	57.1
10′	-	37.3	-	37.8	-	37.7	-	37.7
11′a	4.03; dd; 6.1; 9.9; 1H	67.9	4.02; dd; 6.3; 9.8; 1H	68.2	4.02; dd; 6.0; 9.9; 1H	68.3	4.07; dd; 6.9; 9.9; 1H	68
11′b	4.25; dd; 6.1; 9.9; 1H	67.9	4.29; dd; 5.8; 9.8; 1H	68.2	4.29; dd; 6.0; 9.9; 1H	68.3	4.39; dd; 5.4; 9.9; 1H	68
12′a	4.80; t; 1.9; 1H	112.1	4.72; t; 1.9; 1H	111.5	4.73; brs; 1H	111.5	4.69; t; 2.0; 1H	111.2
12′b	4.89; t; 2.2; 1H	112.1	4.83; t; 2.1; 1H	111.5	4.82; t; 2.2; 1H	111.5	4.79; t; 2.2; 1H
13′	1.13; s; 3H	25.8	1.04; s; 3H	28.6	0.92; s; 3H	16.9	0.84; s; 3H	22.5
14′	1.05; s; 3H	22.3	0.81; s; 3H	15.4	0.89; s; 3H	28.4	0.98; s; 3H	28.5
15′	1.2; s; 3H	21.1	0.99; s; 3H	22.2	1.01; s; 3H	22.2	0.98; s; 3H	22.1
CH₃- (OAc)	-	-	-	-	2.06; s; 3H	21.5	-	-
C=O (OAc)	-	-	-	-	-	171	-
Position	Ferukrin (9)		Ferukrin acetate (10)		Deacetylkellerin (11)		Kellerin (12)
Position	¹H-NMR	¹³C-NMR	¹H-NMR	¹³C-NMR	¹H-NMR	¹³C-NMR	¹H-NMR	¹³C-NMR
2	-	161.3	-	161.4	-	161.4	-	161.3
3	6.2; d; 9.5; 1H	113.1	6.26; d; 9.5; 1H	113.3	6.23; d; 9.5; 1H	113.2	6.25; d; 9.4; 1H	113.6
4	7.6; d; 9.5; 1H	143.6	7.64; d; 9.5; 1H	143.6	7.62; d; 9.5; 1H	143.5	7.63; d; 9.4; 1H	143.5
5	7.35; d; 8.6; 1H	129.2	7.37; d; 8.5; 1H	128.7	7.34; d; 8.4; 1H	129.1	7.37; d; 8.6; 1H	128.9
6	6.78; dd; 2.4; 8.6; 1H	112.7	6.79; dd; 2.2; 8.5; 1H	112.5	6.82; dd; 2.5; 8.4; 1H	113.1	6.86; dd; 2.4; 8.6; 1H	113.1
7	-	161.8	-	161.7	-	162.1	-	162.1
8	6.75; d; 2.4; 1H	101.3	6.78; d; 2.2; 1H	101.4	6.81; d; 2.5; 1H	101.7	6.82; d; 2.4; 1H	101.3
9	-	155.8	-	155.9	-	156	-	156.2
10	-	112.7	-	112.7	-	112.8	-	112.9
1′α	1.46; td; 3.1; 12.7; 1H	35.5	1.38; dt; 3.8; 12.2; 1H	35.4	1.04; dt; 3.0; 12.7; 1H	29.9	1.09; dt; 3.9; 12.9; 1H	31
1′β	1.32; dt; 3.1; 12.7; 1H	35.5	1.59; td; 3.6; 13.2; 1H	35.4	1.93; td; 3.7; 13.3; 1H	29.9	1.76; d; 3.2; 1H	31
2′α	1.69; m; 1H *	27.2	1.75; m; 1H *	23.5	1.55; m; 1H *	25.4	2; tt; 3.1; 14.2; 1H	23
2′β	1.59; dq; 5.5; 13.3; 1H	27.2	1.68; dd; 4.3; 8.7; 1H	23.5	2.04; tt; 3.1; 13.7; 1H	25.4	1.6; dq; 3.4; 14.9; 1H	23
3′	3.12; dd; 4.4, 11.5; 1H	78.9	4.4; dd; 4.65; 11.6; 1H	80.8	3.4; t; 2.9; 1H	76.3	4.63; t; 2.8; 1H	78.6
4′	-	37.5	-	37.8	-	37.8	-	37.1
5′	1.38; dd; 2.1; 8.8; 1H	48.5	1.51; dd; 1.8; 7.3; 1H	48.6	1.8; m; 1H ***	42.5	1.93; dd; 2.5; 12.3; 1H	43.8
6′α	1.53; dt; 3.4; 10.5; 1H	18.3	1.73; m; 1H *	18.2	1.44; dd; 5.9; 1.7; 1H	18.3	1.69; qd; 5.1; 12.3; 1H	18.1
6′ β	1.68; m; 1H *	18.3	1.56; dd; 2.5; 6.4; 1H	18.2	1.68; m; 1H **	18.3	1.49; dq; 2.9; 12.9; 1H	18.1
7′ α	1.68; m; 1H *	39.5	1.73; m; 1H *	39.7	1.73; td; 2.4; 7.6; 1H	39.5	1.77; d; 3.1; 2H	40
7′ β	1.71; m; 1H *	39.5	1.73; m; 1H *	39.7	1.68; m; 1H **	39.5	1.77; d; 3.1; 2H	40
8′	-	73.3	-	73.2	-	73.8	-	73.8
9′	1.5; t; 2.4; 1H	57.8	1.53; t; 3.2; 1H	57.4	1.53; m; 1H *	58.4	1.53; t; 3; 1H	58.1
10′	-	37.9	-	37.6	-	38	-	37.9
11′a	4.05; dd; 3.2; 10.3; 1H	67.7	4.07; dd; 3.3; 10.4; 1H	67.5	4.06; dd; 3.1; 10.3; 1H	68.1	4.17; t; 2.8; 2H	67.8
11′b	4.08; dd; 2.4; 10.3; 1H	67.7	4.1; dd; 2.7; 10.4; 1H	67.5	4.2; dd; 3.1; 10.3; 1H	68.1	4.17; t; 2.8; 2H	67.8
12′a	1.26; s; 3H	31.6	1.29; s; 3H	31.7	1.29; s; 3H	31.7	1.32; s; 3H	31.9
12’b	1.26; s; 3H	31.6	1.29; s; 3H	31.7	1.29; s; 3H	31.7	1.32; s; 3H	31.9
13′	0.78 s 3H	15.6	0.9; s; 3H	16.7	0.87; s; 3H	22.1	0.89; s; 3H	28.4
14′	0.99; s; 3H	28.7	0.91; s; 3H	28.5	0.98; s; 3H	28.6	0.93; s; 3H	21.8
15′	1.29; s; 3H	24.3	1.36; s; 3H	24.2	1.34; s; 3H	24.3	1.36; s; 3H	24.4
CH₃- (OAc)	-	-	2.02; s; 3H	21.3	-	-	1.78; s; 3H	21.2
C=O (OAc)	-	-	-	171	-	-	-	170.6
Position	Samarcandone (13)		Samarcandin (14)		Samarcandin acetate (15)
Position	¹H-NMR	¹³C-NMR	¹H-NMR	¹³C-NMR	¹H-NMR		¹³C-NMR
2	-	161.3	-	161.5	-		161.3
3	6.26; d; 9.5; 1H	113.5	6.22; d; 9.6; 1H	113.2	6.25; d; 9.3; 1H		113.3
4	7.64; d; 9.5; 1H	143.5	7.61; d; 9.6; 1H	143.6	7.63; d; 9.3; 1H		143.5
5	7.37; d; 8.6; 1H	128.9	7.33; d; 8.5; 1H	128.8	7.36; d; 8.5; 1H		128.9
6	6.85; dd; 2.4; 8.6; 1H	113.3	6.83; dd; 2.5; 8.5; 1H	113.3	6.86; dd; 2.3; 8.5; 1H		113.4
7	-	161.6	-	161.9	-		161.9
8	6.91; d; 2.4; 1H	101.7	6.88; d; 2.5; 1H	101.7	6.90; d; 2.3; 1H		101.8
9	-	156	-	156	-		156
10	-	113.1	-	112.7	-		112.8
1′ α	2.03; ddd; 3.9; 7.3; 13.4; 1H	38.7	1.44; dt; 13.4; 3.4; 1H	32.9	1.51; m; 2H *		33.6
1′ β	1.73; ddd; 7.0; 10.9; 13.4; 1H	38.7	1.66; dt; 3.4; 13.4; 1H	32.9	1.51; m; 2H *		33.6
2′ α	2.56; ddd; 7.3; 10.9; 15.9; 1H	33.9	1.57; m; 1H **	25.2	1.66; m; 1H ***		22.7
2′ β	2.45; dt; 3.9; 7.0; 16.1; 1H	33.9	1.92; m; 1H *	25.2	1.88; m; 1H **		22.7
3′	-	216.5	3.42; bt; 2.6; 1H	75.7	4.66; bt; 2.6; 1H		77.8
4′	-	47.4	-	37.5	-		36.7
5′	1.58; m; 1H *	54.8	1.51; bd; 12.6; 1H **	48.5	1.50; m; 1H *		49.7
6′ α	1.67; dq; 3.1; 13.4; 1H	21.4	1.34; bdq; 3.6, 12.6;1H	20.1	1.35; bdq; 3.5; 12.7; 1H		19.9
6′ β	1.48; td; 2.9; 12.4; 1H	21.4	1.58; m; 1H **	20.1	1.63; m; 1H ***		19.9
7′ α	1.98; dt; 3.1; 12.4; 1H	43.4	1.92; m; 1H *	44.2	1.94; m; 1H **		44.1
7′ β	1.58; m; 1H *	43.4	1.55; m; 1H **	44.2	1.58; m; 1H ***		44.1
8′	-	72.5	-	72.7	-		72.8
9′	1.86; t; 5.3; 1H	58.5	1.85; bt; 5.2; 1H	59.4	1.87; bt; 5.1; 1H **		59.4
10′	-	37.6	-	38	-		37.8
11′a	4.21; dd; 5.6; 10.0; 1H	66.6	4.17; dd; 5.4; 9.7; 1H	66.7	4.19; dd; 5.3; 9.7; 1H		66.9
11′b	4.42; dd; 5.1; 10.0; 1H	66.6	4.36; dd; 4.6; 9.7; 1H	66.7	4.36; dd; 5.3; 9.7; 1H		66.9
12′a	1.29; s; 3H	24.7	1.22; s; 3H	24.7	1.25; s; 3H		24.9
12′b	1.29; s; 3H	24.7	1.22; s; 3H	24.7	1.25; s; 3H		24.9
13′	1.13; s; 3H	26.8	0.96; s; 3H	28.5	0.88; s; 3H		28.1
14′	1.06; s; 3H	21.5	0.83; s; 3H	22.2	0.90; s; 3H		21.9
15′	1.07; s; 3H	15.8	0.93; s; 3H	16.1	0.96; s; 3H		16
CH₃- (OAc)	-	-	-	-	2.08; s; 3H		21.4
C=O (OAc)	-	-	-	-	-		170.7

*, **, *** Overlapped or partially overlapped signals.