Table S1. 1H NMR spectroscopic data for compounds 1–4a
No. 1
Reference [1]
6.19 (1H, d, J = 1.8)
6.39 (1H, d, J = 1.8)
7.69 (1H, d, J = 1.8)
6.86 (1H, d, J = 8.2)
7.65 (1H, dd, J =
8.2, 1.8)
5.23 (1H, d, J = 7.3)
2
6
8
2'
5'
6.17(1H, s)
6.37 (1H, s)
7.57 (1H, s)
6.84 (1H, d, J= 8.8)
6'
7.57 (1H, s)
1''
5.40 (1H, d, J=6.7)
2''
3.22 (1H, m )
3.51 (1H, m)
3''
3.22 (1H, m )
3.42 (1H, t, J = 9.0 )
4''
3.18 (1H, m )
3.16 (1H, m)
5''
6''
3.29 (1H, m )
(a)3.86(1H, d, J=
11.2)
(b)3.49(1H, m)
3.30(1H, m)
(a)3.91 (1H, d, J
=11.6)
(b)3.59 (1H, m)
1'''
4.06 (1H, d, J=6.7)
2'''
2.83(1H, m)
3'''
2.97(1H, m)
4.14 (1H, d, J = 7.7
Hz)
6.20 (1H, s)
6.42 (1H, s)
7.76 (1H, m )
6.88 (1H, d, J= 8.5)
7.76 (1H, s)
5.24 (1H ,d, J =7.7)
4.23 (1H, d, J = 8.0 )
Reference[2]
3
4
6.10 (1H, s)
6.26 (1H, s)
7.57 (1H, m )
6.80 (1H, d, J= 7.8)
6.09 (1H, s)
6.28 (1H, s)
7.56 (1H, s)
6.81 (1H, d, J= 8.7)
7.57 (1H, m )
7.56 (1H, s)
5.37 (1H, d, J= 6.8)
5.36 (1H, d, J= 7.4)
3.22 (1H, m )
3.24 (1H, m )
3.22 (1H, m )
3.24 (1H, m )
3.22 (1H, m )
3.13 (1H, t, J= 9.0)
3.68(2H, m)
3.28 (1H, m)
(a)3.88 (1H, d, J=
11.0)
(b)3.53 (1H, m )
4.15(1H, d, J =8.1)
4.17 (1H, d, J = 7.7)
3.30 (1H, m )
(a)3.81 (1H, d, J=
11.5)
(b)3.50(1H, m)
4.10 (1H, t, J =
10.9)
6.15(1H, d, J=1.8)
6.38(1H, d, J=1.8)
8.01(1H, d, J=2.4)
6.84(1H, d, J=9.0)
7.65(1H, dd, J =2.4,
9.0)
5.06(1H, d, J =7.8)
3.80(1H,
dd,
J
=7.8,8.4)
3.54(1H, dd, J =8.4,
7.5)
3.72(1H, dd, J =7.5,
7.2)
3.51(1H, m)
4.45 (1H, dd, J = 9.5, 4.40(1H, dd, J =8.1,
3.06 (1H, m )
8.1)
9.0)
3.16 (1H, m)
3.04(1H, dd, J =9.0, 4.66 (1H, t, J = 9.4)
2.85 (1H, m)
2.98 (1H, m)
4'''
2.97(1H, m)
3.30 (1H, m)
5'''
3.18 (1H, m)
6'''
(a)3.49(1H, m)
2.82 ( 1H, m)
(a) 3.71 (1H, dd, J
=12.1, 2.2)
9.3)
3.20(1H, dd, J =93,
3.22 (1H, m )
9.6)
2.84(1H, m)
3.06 (1H, m )
(a) 3.57 (1H, d, J=
3.69(1H, m)
11.2)
(b)3.59 (1H, m)
3.57(1H, m)
(b)3.36 (1H, dd, J
=11.7,5.1)
(b) 3.43 (1H, m )
2.98 (1H, m)
3.05 (1H, m )
(a) 4.10 (1H, t, J=
10.9)
(b) 3.93 (m)
Ac
1.71 (3H, s)
1.61(3H, s)
1.99 (3H, s)
1.97 (3H, s)
a
Compound 1 (DMSO) and compound 2 (methanol-d4) were measured at 400 MHz; compound 3 (DMSO) and compound 4 (DMSO) were
measured at 600 MHz. The peak assignments for compounds 2–4 were based on DEPT, 1H-1H COSY, HSQC and HMBC experiments, while
the assignment for compound 1 was based on reference.
No.
2
3
4
5
6
7
8
9
10
1'
2'
3'
4'
5'
6'
1''
2''
3''
4''
5''
6''
1'''
2'''
3'''
4'''
5'''
6'''
Ac
Table S2. 13C NMR spectroscopic data for compounds 1–4a
Reference[1] 2
Reference[2] 3
1
156.3
157.1
158.4
158.2
156.6
134.2
136.0
133.3
135.5
133.1
178.0
179.2
177.3
179.2
176.7
161.6
162.9
161.2
163.0
161.0
98.8
98.5
100.1
100.0
99.5
164.7
166.2
164.6
166.3
167.0
93.5
94.9
93.7
95.0
94.0
157.5
158.3
156.4
158.4
155.7
103.2
104.4
105.7
105.6
102.8
121.7
122.6
121.1
122.9
120.6
116.2
117.9
116.3
117.5
116.0
144.5
145.9
144.8
146.0
145.1
148.6
148.5
150.1
150.2
149.4
114.7
116.5
115.3
116.3
115.4
122.2
122.9
121.7
123.5
121.6
103.2
105.7
101.0
103.9
101.3
74.0
74.4
75.7
73.2
74.1
76.6
74.8
76.6
77.9
76.4
70.1
70.5
69.8
71.5
69.6
76.2
77.3
76.5
78.9
76.0
68.2
69.2
68.1
69.0
68.6
102.6
102.1
103.9
102.2
103.2
73.7
75.3
73.4
75.4
71.2
76.4
76.4
75.7
75.7
77.8
70.0
71.3
69.7
71.4
67.6
76.5
77.2
76.6
77.3
76.4
61.2
62.2
60.8
62.2
60.5
20.7
20.3
21.1
169.1
171.9
169.7
4
156.6
133.1
176.8
161.1
99.4
166.7
93.9
155.9
103.1
121.5
116.0
145.1
149.2
115.3
121.5
101.3
74.0
76.5
69.9
76.3
68.4
103.1
73.3
76.2
69.8
76.3
63.5
20.6
170.3
a
Compound 1 (DMSO) and compound 2 (methanol-d4) were measured at 101 MHz;
compound 3 (DMSO) and compound 4 (DMSO) were measured at 151 MHz. The
peak assignments for compounds 2–4 were based on DEPT, 1H-1H COSY, HSQC and
HMBC experiments, while the assignment for compound 1 was based on reference.
References
[1] Byun, E., Jeong, G. S., An, R. B., Min, T. S., Kim, Y. C., Arch. Pharm.
Res. 2010, 33, 67–70.
[2] Shang, X. Y., Wang, Y. H., Li, C., Zhang, C. Z., Yang, Y. C., Shi, J. G.,
Phytochemistry 2006, 67, 511–515.