Sesquiterpenoids and monoterpenoids from the water decoction of Valeriana officinalis L Author Li, Shi-Wei , Bian-Xia Xue &, Tian-Tian Yang &, Ran Li &, Mingjie Zhang &, &, Peng Zhang &, Yi Zhang &, Tao Wang &, Shao-Xia Wang & * & State Key Laboratory of Component-based Chinese Medicine, Institute of Traditional Chinese Medicine, Tianjin University of Traditional Chinese Medicine, 10 Poyanghu &, Bian-Xia Xue &, Tian-Tian Yang &, Ran Li Author Xue, Bian-Xia Author Yang, Tian-Tian Author Li, Ran Author Zhang, Mingjie Author Wang, Miao Author Zhang, Li-Hua Author Zhang, Peng Author Zhang, Yi Author Wang, Tao Author Wang, Shao-Xia Author Wu, Hong-Hua text Phytochemistry 2023 113474 2023-01-31 205 1 11 http://dx.doi.org/10.1016/j.phytochem.2022.113474 journal article 10.1016/j.phytochem.2022.113474 1873-3700 8194509

Table 1 NMR data for 1–3.

position	1 a			2 a			3 a
a Measured in CD OD; 3 b Measured at 600 MHz; c Measured at 150 MHz.
	δ (J in Hz) b H	δ type c C,	HMBC	δ (J in Hz) b H	δ type c C,	HMBC	δ (J in Hz) b H	δ type c C,	HMBC
1	–	77.8, C	–	–	76.8, C	–	–	144.8, C	–
2	2.15, dd (13.2, 6.6)	38.7, CH2	1, 3, 4, 10, 11	1.73, dd (14.2, 5.3)	32.8, CH2	1, 3, 4, 10, 11	2.21, m	31.3, CH2	1, 4, 5
	1.51, dd (13.2, 12.0)			1.59, m
3	4.88, m	76.6, CH	1, 4, 12, 1′	1.49, m	29.6, CH2	1, 4, 12	2.05, m	32.8, CH2	1, 2, 5, 12
				1.40, m			1.31, m
4	2.01, m	35.1, CH	–	1.96, m	28.9, CH	–	2.44, m	43.6, CH	1, 2, 6,
5	1.58, m	44.9, CH	3, 12, 13	1.38, m	44.3, CH	1, 3, 12, 13	–	135.8, C	–
6	1.54, m	26.8, CH2	4, 8, 10, 11	1.57, m	25.0, CH2	4, 8, 10, 11	2.31, m	31.0, CH2	1, 4, 8
	1.44, m			1.30, m			1.79, d (17.6)
7	1.18, m	40.1, CH	9, 15	1.60, m	45.8, CH	9, 15	2.01, m	52.8, CH	5, 9, 14, 15
8	1.92, m	25.2, CH2	6, 10, 11	3.88, m	81.4, CH	6, 10, 11, 1′	3.95, dd (8.4,	86.5, CH	6, 10, 1′
	1.27, m						4.8)
9	1.93, m	29.2, CH2	1, 5, 7, 8,	2.05, dd (13.8, 7.8)	37.8, CH2	1, 5, 8, 10,	2.23, dd (13.2,	49.4, CH2	1, 7, 11
							7.8)
	1.10, m			1.54, m			1.85, dd (13.2,
							2.4)
10	–	38.5, C	–	–	40.0, C	–	–	144.8, C	–
11	–	41.1, C	–	–	41.5, C	–	–	43.0, C	–
12	0.892, s	21.5, CH3	3, 5	0.89, s	21.0, CH3	3, 5	0.94, d (7.2)	15.4, CH3	3, 5
13	0.895, d (6.6)	15.2, CH3	1, 5, 9	0.82, d (6.6)	19.3, CH3	1, 5, 9	0.95, s	19.5, CH3	1, 9
14	1.12, s	25.4, CH3	1, 7, 11, 15	1.10, s	25.8, CH3	1, 7, 11, 15	0.90, s	20.1, CH3	7, 10, 15
15	1.07, s	27.2, CH3	1, 7, 11, 14	1.17, s	29.0, CH3	1, 7, 11, 14	1.10, s	24.0, CH3	7, 10, 14
1′	–	173.0, C	–	4.29, d (7.8)	103.9, CH	8, 3′, 5′	4.18, d (7.8)	103.4, CH	8, 3′, 5′
2′	2.03, s	21.1, CH3	1′	3.14, dd (9.6, 8.4)	75.3, CH	1′, 3′, 4′	3.12, t (8.4)	75.1, CH	1′, 3′, 4′
3′	–	–	–	3.33, t (9.0)	78.2, CH	1′, 2′, 4′	3.31, m	78.3, CH	1′, 2′, 4′
4′	–	–	–	3.25, t (9.0)	71.8, CH	3′, 6′	3.28, t (8.4)	71.7, CH	3′, 6′
5′	–	–	–	3.37, ddd (9.6, 6.0, 1.8)	76.6, CH	1′, 3′, 4′	3.21, m	77.9, CH	1′, 3′, 4′
6′	–	–	–	3.96, d (10.2)	68.7, CH2	4′, 1′′	3.85, dd (12.0,	62.8, CH2	4′, 5′
							2.4)
				3.59, dd (11.4, 6.0)			3.66, dd (12.0,
							6.0)
1′′	–	–	–	5.00, d (2.4)	110.9, CH	6′, 2′′, 3′′	–	–	–
2′′	–	–	–	3.89, d (2.4)	78.0, CH	1′′, 4′′, 5′′	–	–	–
3′′	–	–	–	–	80.6, C	–	–	–	–
4′′	–	–	–	3.76, d (9.6), 3.95, d (10.2)	75.0, CH2	2′′, 3′′, 5′′	–	–	–
5′′	–	–	–	3.58, s	65.8, CH2	2′′, 3′′, 4′′	–	–	–
–	4.58, s	-OH	–	–	–	–	–	–	–