Structure Elucidation of the Main Tetrahydroxyxanthones of Hypericum Seeds and Investigations into the Testa Structure

Article abstract of DOI:10.1002/cbdv.201800035

Seeds from Hypericum species have recently been identified as an interesting source of xanthone derivatives. Extraction of seeds from H. perforatum with MeOH and subsequent concentration via polyamide adsorption yielded a fraction enriched in tetrahydroxy

Full text of DOI:10.1002/cbdv.201800035

This article has been accepted for publication and undergone full peer review but has not been
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1
0.1002/cbdv.201800035
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H8
s
H5
s
X1
X2
H8
s
H3
d
H2
d
H5
s
H4
d
H3
d
PPM
7.50
7.40
7.30
7.20
7.10
7.00
6.90
6.80
6.70
6.60
6.50
6.40
This article is protected by copyright. All rights reserved.

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This article is protected by copyright. All rights reserved.

a)
b)
c)
UV Chromatogram, 260 nm
X1
3
00
X2
2
00
1
00
0
500
400
300
200
100
1
Intens.
2
22
UV, 24.9 min
[
mAU]
2
56282
500
4
00
300
00
2
392
100
0
2
00 250 300 350 400 450
Wavelength [nm]
0
00
00
00
00
00
00
0
6
5
4
3
2
1
Intens.
mAU]
2
[
UV, 25.7min
2
34
252
6
4
2
00
00
00
0
3
28
392
2
00 250 300 350 400 450
Wavelength [nm]
2
0
21
22
23
24
25
26
27
28
29
Time [min]
d)
7
258.77
-MS, 24.8-25.2min
x10
[
M-H]-
3
2
1
0
M-H-HCOH]-
[
4
M-H-CO ]-
228.73
-MS2(258.77)
[
x10
2
4
3
2
1
0
[M-H-H O]-
[
M-H-CO -CO]-
2
2
2
01.65
214.62
186.66
1
50.71 161.49
240.85
100
120
140
160
180
200
220
240
260
280
m/z
e)
7
258.76
-MS, 25.6-25.9min
x10
[
M-H-HCOH]-
[M-H]-
2
0
5
2
28.69
-MS2(258.76)
x10 6
[M-H-HCOH-CO]-
4
2
0
3
2
00.69
-MS3(258.76->228.69)
4
2
0
x10
1
44.80 156.68
1
12.93
1
73.24 184.64
100
120
140
160
180
200
220
240
260
280
m/z
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±
± 13.08
20.90
±


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Scan EI+
TIC
X2-Me
X2-Me
a)
1
1
1
1
00
%
0
X0-Me
X0-Me
X1-Me
X1-Me
Scan EI+
TIC
b)
c)
00
%
0
C27
C28
C29
C30
Scan EI+
TIC
1
0
00
%
0
11
Scan EI+
TIC
d)
00
%
0
47.0
48.0
49.0
50.0
51.0
52.0
53.0
Time
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a) 1
00
X2-TMS
Scan EI+
TIC
X1-TMS
5
0
X3-TMS
0
b)
1-TMS
Scan EI+
TIC
1
00
5
0
0
c)
Scan EI+
TIC
2
-TMS
1
00
5
0
0
3
-TMS
Scan EI+
TIC
d) 100
5
0
0
4
8.0
49.0
50.0
51.0
52.0
53.0
Time
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á
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This article is protected by copyright. All rights reserved.




This article is protected by copyright. All rights reserved.

This article is protected by copyright. All rights reserved.

This article is protected by copyright. All rights reserved.

9
.4 Hz 9.3 Hz
.8 Hz
3
2
.9 Hz
8.6 Hz
2.7 Hz
10.9 Hz
5.5 Hz
4.8 Hz
3.4 Hz
9.5 Hz
5.2 Hz
3.6 Hz
4.8 Hz
7.5 Hz
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2.8 Hz
9.4 Hz
9.6 Hz
6.5 Hz
8
.6 Hz
.1 Hz
.9 Hz
9
8
2.6 Hz
5.4 Hz
3.4 Hz
4.9 Hz
7.8 Hz
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This article is protected by copyright. All rights reserved.

á
š
á
á
Č
á
á
This article is protected by copyright. All rights reserved.

á
á
á
í
š
This article is protected by copyright. All rights reserved.