Evidence-Based Complementary and Alternative Medicine

Research Article

Pimarane Diterpenoids from Aerial Parts of Lycopus lucidus and Their Antimicrobial Activity

Table 2

¹H-NMR spectroscopic data of compounds 10–14 at 400 MHz.


C	¹H-10	¹H-11	¹H-12	¹H-13	¹H-14

1	1.70 (1H, m, H-1a) 1.22 (1H, m, H-1b)	1.51 (1H, m, H-1a) 0.93 (1H, m, H-1b)	1.83 (1H, m, H-1a) 1.14 (1H, m, H-1b)	1.70 (1H, m, H-1a) 1.20 (1H, m, H-1b)	1.81 (1H, m, H-1a) 1.11 (1H, m, H-1b)
2	1.94 (1H, m, H-2a) 1.50 (1H, m, H-2b)	1.60 (1H, m, H-2a) 1.43 (1H, m, H-2b)	1.97 (1H, m, H-2a) 1.56 (1H, m, H-2b)	1.96 (1H, m, H-2a) 1.56 (1H, m, H-2b)	1.83 (1H, m, H-2a) 1.50 (1H, m, H-2b)
3	3.39–3.42 (1H, m, H-3)	1.46 (1H, m, H-3a 1.27 (1H, m, H-3b)	3.59 (1H, t H-3)	3.43 (1H, m, H-3)	4.1 (1H,t, H-3)
5	2.07 (1H, dd, 2.0, 12.6 Hz, H-5)	1.92 (1H, m, H-5)	2.015 (1H, dd,2.0, 12.6 Hz, H-5)	2.03 (1H, dd, 2.0, 12.6 Hz, H-5)	1.96 (1H, m, H-9)
6	1.78 (1H, m, H-6a) 1.45 (1H, m, H-6b)	2.04 (1H, m, H-6a) 1.54 (1H, m, H-6b)	1.76 (1H, m, H-6a) 1.48 (1H, m, H-6b)	1.76 (1H, m, H-6a) 1.45 (1H, m, H-6	2.00 (1H, m- H6a) 1.70 (1H, m, H-6b)
7	1.42 (2H, m, H-7)	3.57 (1H, t, H-7)	1.43 (2H, m, H-7)	1.50 (2H, m, H-7)	1.42 (1H, m, H-7a) 1.25 (1H, m, H-7b)
9	1.91 (1H, m, H-9)	1.65 (1H, m, H-9)	2.042, (1H, d, 2.8 Hz, H-9)	1.84 (1H, m, H-9)	2.15 (1H, dd, 2.0, 13.2 Hz, H-5)
11	2.38 (1H, td, 2.8, 2.4, 13.2 Hz, H-11a) 1.56 (1H, m, H-11b)	2.41 (1H, td, 2.8, 2.4, 13.2 Hz, H-11a) 1.56 (1H, m-H11b)	4.1 (1H, t, H-11)	2.39(1H, td, 2.8, 2.4, 13.2 Hz, H-11a 1.66 (1H, m, H-11b)	1.93 (1H, m, H-11a) 1.53 (1H, m, H-11b)
12	3.39–3.42 (1H, m, H-12)	3.48 (1H, m, H-12)	3.28 (1H, m, H-12)	4.62 (1H,t, H-12)	3.49 (1H, m, H-12)
14	2.015 (1H, d,14.4 Hz, H-14a) 1.19 (1H, m, H-14b)	2.347(1H, d, 14.4 Hz, H-14a) 1.098 (1H, dd, 0.8, 14.4 Hz, H-14b)	1.93 (1H, m, H-14a) 1.26 (1H, m, H-14b)	1.63 (1H, m, H-14a) 1.23 (1H, m, H-14b)	2.03 (1H, m, H-14a) 1.15 (1H, m, H-14b)
15	5.78 (1H, dd, 10.8, 17.2 Hz, H-15)	5.91 (1H, dd, 10.8, 17.2 Hz, H-15)	5.76 (1H, dd, 10.8, 17.2 HzH-15)	5.75 (1H, dd, 10.8, 17.2 Hz, H-15)	5.76 (1H, dd, 10.8, 17.2 Hz, H-15)
16	4.90 (1H, dd, 1.2, 17.4 Hz, H-16a) 4.79 (1H, dd, 1.2, 17.4 Hz, H-16b)	5.00 (1H, dd, 1.2, 14.2 Hz, H-16a) 4.97 (1H, dd, 1.2, 7.6 Hz, H-16b)	4.88 (1H, dd, 1.2, 17.4 Hz, H-16a) 4.79 (1H, dd, 1.2, 17.4 Hz, H-16b)	4.86 (1H, dd, 1.2,17.4 Hz, H-16a) 4.80 (1H, dd, 1.2, 17.4 Hz, H-16b)	4.84 (1H, dd, 1.2, 17.4 Hz, H-16a) 4.74 (1H, dd, 1.2, 17.4 Hz, H-16b)
17-CH₃	0.92 (3H, s, H-17)	0.912 (3H, s, H-17)	1.01 (3H, s, H-17)	0.84 (3H, s, H-17)	0.88 (3H, s, H-17)
18	3.89 (1H, d, 12.0 Hz, H-18a) 3.54 (1H, d, 12.0 Hz, H-18b)	4.50 (1H, d, 12 Hz, H-18a) 3.487 (1H, d, 12 Hz, H-18b)	3.85 (1H, d,12.0 Hz, H-18a) 3.54 (1H, d,12.0 Hz, H-18b)	3.94 (1H, d,12.0 Hz, H-18a) 3.56 (1H, d, 12.0 Hz, H-18b)	5.08 (1H, d, 12.0 Hz, H-18a) 4.52 (1H, d, 12.0 Hz, H-18b)
19-CH₃	1.24 (3H, s, H-19)	1.26 (3H, s, H-19)	1.24 (3H, s H-19)	1.24 (3H,s, H-19)	1.23 (3H, s, H-19)
20-CH₃	1.01 (3H, s, H-20)	1.01(3H,s, H-20)	1.25 (3H, s, H-20)	1.00 (3H, s, H-20)	0.89 (3H, s, H-20)
22-OCH₃				2.06 (3H, s, H-22)	1.98 (3H, s, H-22)