One new sesquiterpene lactone from Illicium simonsii

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SUPPLEMENTARY MATERIAL
A new inositol triester from Taraxacum mongolicum
Jifeng Liu a, *, Nenling Zhang c and Mengqi Liu b, *
a
School of Pharmaceutical Science, Zhengzhou University, Ke Xue Da Dao 100, Zhengzhou 450001, People’s Republic of China
b
School of Pharmaceutical Science, Henan University of Traditional Chinese Medicine, Zhengzhou, 450008, People’s Republic of China
c
School of Pharmacy, Guiyang Medical College, Guiyang, 550004, People’s Republic of China
*Corresponding author. E-mail: [email protected]
1
A new inositol triester from Taraxacum mongolicum
One new inositol triester, 4,5,6-tri-O-p-hydroxyphenylacetyl-chiro-inositol (1) was isolated from the ethanol extract of Taraxacum
mongolicum, along with two known compounds, 11,13-dihydrotaraxinic acid (2) and taraxinic acid -D-glucopyranosyl ester (3). The
isolates were tested for their anti-hepatitis B virus (HBV) activities, 11,13-dihydrotaraxinic acid (2) exhibited an IC50 value of 0.91 mM
inhibiting on HBV surface antigen (HBsAg) secretion and an IC50 value of 0.34 mM inhibiting on HBV e antigen (HBeAg) secretion
using HBV transfected Hep G2.2.15 cell line.
Key words: Taraxacum mongolicum, Inositol, Anti-HBV
2
The spectroscopic data of compounds 2-3:
11, 13-Dihydrotaraxinic acid (2). White amorphous powder; []22.5
D – 46.4 (c 0.55, MeOH); UV (MeOH, max, nm): 204, 306, 390; IR
(KBr, max, cm–1): 3413–3000, 1767, 1680, 1632, 1442, 1178, 984, 967; EI-MS m/z (%): 264 ([M]+, 35), 191 (35), 145 (65), 107 (70), 91 (80);
HR-ESI-MS m/z: 265.1438 [M+H]+ (calcd. for C15H21O4: 265.1362); 1H NMR (500 MHz, CD3OD, δ, ppm, J/Hz): 5.71 (1H, dd, J = 12.1, 3.0 Hz,
H-1), 4.87 (1H, d, J = 10.1 Hz, H-5), 4.70 (1H, dd, J = 10.1, 9.3 Hz, H-6), 3.33 (1H, m, H-2a), 2.77 (1H, m, H-9a), 2.32 (2H, m, H-3a, H-11),
2.27 (2H, m, H-2b, H-3b), 1.91 (3H, m, H-8, H-9b), 1.62 (3H, s, H-15), 1.19 (3H, d, 7.0, H-13); 13C NMR (125 MHz, CD3OD): 147.3 (d, C-1),
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27.4 (t, C-2), 40.1 (t, C-3), 142.9 (s, C-4), 127.4 (d, C-5), 83.4 (d, C-6), 55.7 (d, C-7), 31.4 (t, C-8), 37.8 (t, C-9), 132.6 (s, C-10), 43.4 (d, C-11),
181.4 (s, C-12), 13.3 (q, C-13), 171.3 (s, C-14), 16.9 (q, C-15).
Taraxinic acid -D-glucopyranosyl ester (3): C21H28O9; EI-MS m/z (%): 263 (M-C6H9O5, 100)+, 217 (25),159 (30),119 (65); 1H-NMR
(500 MHz, C5D5N ) δ: 6.88 (1H, d, J = 7.0 Hz, H-13), 5.98 (1H, d, J = 6.7 Hz, H-13′), 5.33 (1H, d, J = 8.0 Hz, H-1′), 5.30 (1H, m, H-1),
5.08~5.18 (2H, m, H-2′, 3′), 4.59 (1H, m, H-5), 4.50 (1H, m, H-6), 3.90~4.09 (3H, m, H-5′, 6′), 1.66~2.01 (9H, m, H-2, 3, 7, 8, 9), 1.35 (3H, d, J
= 3.3 Hz, H-15); 13C-NMR (125 MHz, C5D5N) δ: 148.7 (d, C-1), 27.0 (t, C-2), 39.4 (t, C-3), 141.1 (s, C-4), 126.9 (d, C-5), 82.2 (d, C-6), 50.3 (d,
C-7), 30.6 (t, C-8), 36.8 (t, C-9), 131.4 (s, C-10), 143.3 (s, C-11), 170.6 (s, C-12), 119.5 (t, C-13), 166.9 (s, C-14), 17.2 (q, C-15), 95.7 (d, C-1′),
74.2 (d, C-2′), 78.9 (d, C-3′), 71.2 (d, C-4′), 79.6 (d, C-5′), 62.4 (t, C-6′).
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Figure S1
The Key HMBC correlations of compound 1
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Figure S2
Key ROESY correlations of compound 1
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The spectra of compound 1:
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Figure S3
The 1H NMR spectrum of compound 1
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Figure S4
The 13C NMR spectrum of compound 1
of compound 1
The 13C NMR of compound 1
The HSQC spectrum of compound 1
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Figure S5
The HSQC spectrum of compound 1
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Figure S6
The HMBC spectrum of compound 1
The ROESY spectrum of compound 1
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Figure S7
The 1H-1H COSY spectrum of compound 1
The HRESIMS of compound 1
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Figure S8
The ROESY spectrum of compound 1
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Figure S9
The negative FABMS spectrum of compound 1
The IR (KBr) of compound 1
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Figure S9a The negative HRFABMS spectrum of compound 1
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Figure S9b The negative HRFABMS spectrum of compound 1
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Figure S10
The IR (KBr) spectrum of compound 1
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