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. Author manuscript; available in PMC: 2016 Apr 24.
Published in final edited form as: J Nat Prod. 2015 Mar 17;78(4):789–796. doi: 10.1021/np5010328

Table 1.

1H (400 MHz) NMR Spectroscopic Data for Compounds 1-4 (δ in ppm, J in Hz)a

1b
2c
3c
4b
position δH (J in Hz) δH (J in Hz) δH (J in Hz) δH (J in Hz)
1 2.75, ddd (4.5, 12.4, 12.4) 2.68, ddd (4.8, 12.1, 12.18) 2.92, d (11.8) 2.45, dd (0.8, 11.5)
1.90, dddd (4.1, 4.2, 12.2, 12.4 ) 1.88, dddd (4.2, 4.4, 12.2, 12.5) 1.86, dd (1.5, 11.8) 2.31, dd (1.6, 11.5)
2 2.28, ddd (4.5, 12.0, 14.0) 2.21, md
2.05, ddd (4.5, 12.1, 14.0) - -
3 - - 3.75, d (11.0) 3.95, d (1.0)
5 2.37, dd (2.2, 8.0) 2.26, dd (2.2, 8.0)d 2.24, dd (1.3, 5.8) 2.19, dd (1.1, 5.8)
6 5.19, ddd (5.7, 8.0, 9.7) 5.11, ddd (6.0, 8.1, 9.7) 5.17, ddd/br quintet-like (5.1, 5.1, 10.2) 5.21, ddd/br quintet-like (4.9, 5.7, 10.2)
7 4.22, dd (9.7, 17.3) 4.15, dd (9.9, 17.2) 4.05, dd (9.9, 17.4) 4.03, dd (9.9, 17.3)
3.03, dd (5.6, 17.2) 2.98, dd (5.9, 17.1) 2.98, dd (4.8, 17.4) 2.93, dd (4.7, 17.3)
11 7.23, d (8.2) 6.57, s 6.52, s 6.65, s
12 7.49, dd (0.9, 8.1) - - -
15 6.81, d (2.2) 6.83, d (2.2) 6.84, d (2.2) 6.84, d (2.2)
16 7.75, d (2.2) 7.53, d (2.2) 7.52, d (2.2) 7.64, d (2.2)
18 1.44, s 1.44, s 1.60, s 2.14, s
20 4.12, dd (3.7, 9.6) 4.14, dd (3.7, 9.7) 4.25, dd (1.5, 9.0) 4.18, dd (1.6, 8.6)
3.77, dd (2.2, 9.6) 3.82, dd (2.2, 9.7) 3.76, dd (1.5, 9.0) 3.54, dd (1.5, 8.6)
OCH3 - 3.92, s 3.91, s 3.94, s
2-OH - - 4.29, s -
3-OH - - 5.01, d (10.6) -
a

For CH2, the deshielded signal was assigned as Ha, and the shielded signal as Hb.

b

Data measured in methanol-d4.

c

Data measured in CDCl3.

d

Signal was partially obscured.