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SUPPLEMENTARY MATERIAL
New phenolic acids from Salvia yunnanensis C.H.Wright
Yun Yu a, Yin-ru Wang
a, Zhen-huan Dong
a, Wei Li
b, Shu-Ming Li
b, Xue-feng
Huang a*
aDepartment of Natural Medicinal Chemistry, China Pharmaceutical University,
Nanjing, 210009, P. R. China; bTasly R&D Institute, Tasly Pharmaceutical Co., Ltd.,
Tianjin 300410, P. R. China
* Corresponding author: Xue-feng Huang
Tel.: +86-25-52716876; Fax: +86-25-85301528.
E-mail address: [email protected].
Abstract
Two new phenolic acids, ethyl pro-lithospermate (1), n-butyl pro-lithospermate (2)
were isolated from Salvia yunnanensis C.H.Wright, along with nineteen known
compounds (3-21). The structures of the isolated compounds were elucidated on the
basis of extensive spectrometry and by comparing their physical and spectroscopic
data to literature. Among them, compounds 11, 12 and 14-16 were firstly isolated
from Salvia yunnanensis C.H.Wright. Some of the isolated compounds were
evaluated for their neuroprotection. Compound 10-12 showed significant
neuroprotective effects in PC12 cells and compounds 1, 4-7 displayed moderate
neuroprotective effects.
Keywords:
Salvia yunnanensis; phenolic acids; phenylpropanoids; neuroprotection
Figure S1. Key 1H-
1H COSY and HMBC correlations (H→C) in compound 1 and
compound 2
Figure S2. The CD spectrum of 1 (black in MeOH) and salvianolic acid B
(green in MeOH)
Figure S3. The CD spectrum of 2 (black in MeOH) and salvianolic acid B
(green in MeOH)
Figure S4. 1H-NMR spectrum of 1
Figure S17. HR-ESI-MS spectrum of 2
Figure S18. HPLC chromatogram of compound 1 (rose) and the DMSO extract
of S. yunnanensis (black)
2.5 5.0 7.5 10.0 12.5 15.0 min
0
25000
50000
75000
100000
125000
150000
175000
200000
225000
uV
2.5 5.0 7.5 10.0 12.5 15.0 17.5 20.0 22.5 25.0min
0
25000
50000
75000
100000
125000
150000
175000
uV
Figure S19. HPLC chromatogram of compound 2 (rose) and the DMSO extract
of S. yunnanensis (black)
Table S1. 1H- NMR (300 MHz) and
13C- NMR (75 MHz) of compound 1 and
compound 2 in DMSO-d6 (δ in ppm, J in Hz)
Position 1 2
δH δC δH δC
1 - 122.5 122.6
2 - 125.6 125.4
3 - 147.0 146.9
4 - 143.6 143.6
5 6.81 (1H, d, J = 8.4) 117.3 6.79 (1H, d, J = 8.4) 117.3
6 7.21 (1H, d, J = 8.4) 120.4 7.21 (1H, d, J = 8.4) 120.3
7 7.55 (1H, d, J = 15.9) 140.7 7.54 (1H, d, J = 15.9) 140.7
8 6.25 (1H, d, J = 15.9) 117.2 6.24 (1H, d, J = 15.9) 117.3
9 - 167.6 167.7
1' - 131.0 130.9
2' 6.73 (1H, br.s) 112.9 6.72 (1H, br.s) 112.9
3′ - 145.6 145.4
4' - 145.6 145.6
5'′ 6.71 (1H, d, J = 7.8) 115.6 6.71 (1H, d, J = 7.8) 115.4
6' 6.65 (1H, d, J = 7.8) 117.0 6.64 (1H, d, J = 7.8) 116.9
7' 5.79 (1H, d, J = 5.0) 86.3 5.79 (1H, d, J = 4.7) 86.2
8' 4.43 (1H, d, J = 5.0) 55.2 4.43 (1H, d, J = 4.7) 55.2
9' - 171.2 171.2
10' 4.14 (2H, q, J = 7.0) 61.3 4.08 (2H, m) 64.9
11' 1.19 (3H, t, J = 7.0) 13.7 1.53 (2H, m) 29.9
12' 1.23(2H, m) 18.5
13' 0.82 (3H, t, J = 7.2) 13.4