Sesquiterpene lactones from the methanol extracts of twenty-eight Hieracium species from the Balkan Peninsula and their chemosystematic significance Author Milutinović, Violeta Department of Pharmacognosy, University of Belgrade - Faculty of Pharmacy, Vojvode Stepe 450, 11221 Belgrade, Serbia Author Niketić, Marjan Natural History Museum, Njegoševa 51, 11000 Belgrade, Serbia Author Krunić, Aleksej Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois, Chicago, IL 60612, USA Author Nikolić, Dejan Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois, Chicago, IL 60612, USA Author Petković, Miloš Department of Organic Chemistry, University of Belgrade - Faculty of Pharmacy, Vojvode Stepe 450, 11221 Belgrade, Serbia Author Ušjak, Ljuboš Department of Pharmacognosy, University of Belgrade - Faculty of Pharmacy, Vojvode Stepe 450, 11221 Belgrade, Serbia Author Petrović, Silvana Department of Pharmacognosy, University of Belgrade - Faculty of Pharmacy, Vojvode Stepe 450, 11221 Belgrade, Serbia silvana.petrovic@pharmacy.bg.ac.rs text Phytochemistry 2018 2018-10-31 154 19 30 http://dx.doi.org/10.1016/j.phytochem.2018.06.008 journal article 285208 10.1016/j.phytochem.2018.06.008 56a5f933-818c-48d4-b58c-98dfe3177685 1873-3700 10484041

Table 2 1 H, 13 C, DEPT, HMBC, and NOESY/ROESY data of compounds 1, 2 and 3 in D O.

Pos.		1 a				Pos.		2 b				3 a
a 1 H (400 MHz), 13 C (101 MHz), at 298 K. b 1 H (500 MHz), 13 C (125 MHz), at 292–295 K. c Resolved in HMBC.
		δ H	δ C	HMBC	NOESY			δ H	δ C	HMBC	ROESY	δ H	δ C	HMBC	ROESY
1		5.71 dd (9.8, 2.0)	140.41	3, 14	2	1		3.04 d (4.0)	43.95	2 α / β, 5, 9 β		2.97 q (8.2)	43.90	2 α, 3, 7, 9 β, 14a/b	1, 2 β, 14b
2		5.59 dd (9.6, 2.5)	125.61		1	2	α	1.71 m	36.98			1.84 td (14.2, 7.2)	36.48	1	9 α
							β	2.35 m			6, 9 β	2.31 td (13.2, 8.1)			3
3		4.89 s	78.05	1, 5, 15a, 1′	1, 5, 1′	3		4.63 t (8.2)	72.25	2 α, 15a/b	2 β, 5	4.62 t (6.7)	80.93	1, 2 α / β, 15a/b, 1′	5, 15b, 1′
4		–	141.26	5		4		–	152.39c	2 β, 3, 5, 15b		–	148.81	3, 6, 7, 15a/b
5		2.57 d (11.1)	50.39	14,15a	3, 9 α	5		3.01 d (11.6)	49.26	1, 2 α	7, 9 α, 15b	2.30 t (9.3)	53.20		1, 3, 7, 11
6		4.52 t (11.0)	77.52	5	8, 11, 14, 15a	6		4.37 t (9.6)	80.14	1, 5, 7	2 β, 8, 9 β, 11	4.33 t (10.1)	80.29	9 β	15a, 5″b
7		2.16 q (11.5)	55.82	1, 13 β, 14		7		2.49 d (9.5)	52.65	9 α / β, 13 β	13 α	2.89 t (9.8)	49.67	1, 5, 6, 9 β, 15a/b	5, 15b
8		4.10 dd (12.1, 4.4)	66.54	9 β	6, 14	8		4.09 m	70.93	6, 9 α / β	6, 9 β, 11, 13 α	4.01 dd (9.7, 4.0)	70.35		9 β
9	α	1.41 t (11.7)	45.05	14	5, 8, 9 β, 11	9	α	2.33 dd (14.6, 7.6)	42.87	14a/b		2.21 dd (13.9, 4.9)	42.80
	β	2.01 dd (12.6, 4.5)			9 α, 14		β	2.79 dd (13.1, 4.8)			2 β, 6, 8	2.69 dd (14.0, 4.8)			14a, 6′ β
10		–	39.41	1, 2, 5, 9 β		10		–	143.08	1, 2 β, 5, 9 β		–	143.25	1, 2 α, 9 α / β, 14b
11		3.26 d (9.3)	42.34	13 β	5, 9	11		3.34 t (7.7)	43.03	13 β		3.24 t (8.4)	43.18	13 α	7, 9 β
12		–	173.88	13 α		12		–	177.75c	6, 11		–	177.61	11
13	α	3.47 t (10.1)	55.03	5″b	13 β	13	α	3.72 q (7.7)	55.20	7, 11		3.23 dd (11.2, 2.3)	55.33
	β	3.68 t (8.9)			13 α		β	3.58 q (6.7)				3.84 dd (8.4, 1.8)
14		0.87 s	20.86	5	1, 6, 8	14	a	5.10 brs	115.34	9 α		4.98 s	116.33	1, 9 α / β	9 β, 3″a
							b	5.10 brs				5.06 s			1, 2 α, 3
15	a	4.95 s	107.85	3, 5	6, 15b	15	a	5.30 s	110.59			5.37 s	114.64	3	6
	b	5.48 s			15a, 1′		b	5.34 s				5.40 s			3, 5, 1′
1′		4.58 d (7.9)	103.25	2′	3, 15b, 3′, 5′	1′						4.53 d (7.9)	100.99	3, 3′, 4′	1, 15b, 3′, 5′
2′		3.29 t (7.9)	73.57			2′						3.34 d (9.4)	75.87	1′, 3′, 4′, 6′ α
3′		3.43 d (1.8)	75.98	2′	1′, 5′	3′						3.88	73.18	1′, 4′	1′
4′		3.35 d (1.8)	69.63	2′, 3′, 6′ β		4′						3.40 t (8.9)	70.44
5′		3.37 d (1.9)	75.90	3′, 6′ β	1′, 3′	5′						3.28 t (9.2)	73.23
6′	α	3.64 dd (12.6, 2.20)	60.72			6′	α					3.63 t (5.2)	60.87	4′
	β	3.85 dd (12.4, 1.9)					β					3.89 dd (13.6, 1.3)			6, 9 β
1″		–	177.32			1″		–	174.59c	2″		–	175.21
2″		4.05 d (9.5)	70.48	13 α	3″b, 4″b	2″		4.15 m	70.15			3.36 dd (6.9, 1.8)	69.75	13 β, 5″a/b
3″	a	2.16 m	29.08		3″b	3″	a	2.26 q (8.0)	28.50	2″		2.20 m	28.90	4″a/b
	b	2.43 m			2″, 3″a		b	2.45 d (9.9)				2.47 m			4″b
4″	a	1.91 m	23.55		4″b	4″	a	2.01 m	23.31	3″a	3″a	1.98 m	23.53
	b	2.14 m			2″, 4″a, 5″b		b	2.22 m				2.16 m			3″b
5″	a	3.82 d (6.0)	56.04			5″	a	3.32 m	55.01		13 α	3.49 dd (12.7, 6.5)	55.51
	b	3.23 d (5.8)					b	3.93 m				3.64 dd (11.3, 6.2)