A new flavanone glycoside isolated from Tournefortia sibirica

Article abstract of DOI:10.1080/14786419.2018.1512995

A new flavanone glycoside, (2S)-dihydrooroxylin A 7-O-[β-D-apiosyl(1→2)]-β-D-glucoside (1), and four known compounds (2–5) were isolated from Tournefortia sibirica L. The chemical structures of these compounds were determined by 1 D and 2 D NMR and HR-ESI-MS spectra, and results were compared with data from the literature. These five compounds (1–5) were isolated from the family Boraginaceae for the first time. Anti-inflammatory effects of compounds (1–5) were evaluated in terms of inhibition of production of NO, TNF-α, and IL-6 in LPS-induced RAW 264.7 cells.

Full text of DOI:10.1080/14786419.2018.1512995

Natural Product Research
Formerly Natural Product Letters
ISSN: 1478-6419 (Print) 1478-6427 (Online) Journal homepage: http://www.tandfonline.com/loi/gnpl20
A new flavanone glycoside isolated from
Tournefortia sibirica
Shengbao Diao, Mei Jin, Chun Shi Jin, Cheng-Xi Wei, Jinfeng Sun, Wei Zhou &
Gao Li
To cite this article: Shengbao Diao, Mei Jin, Chun Shi Jin, Cheng-Xi Wei, Jinfeng Sun, Wei Zhou
&
Gao Li (2018): A new flavanone glycoside isolated from Tournefortiaꢀsibirica, Natural Product
Research, DOI: 10.1080/14786419.2018.1512995
To link to this article: https://doi.org/10.1080/14786419.2018.1512995
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NATURAL PRODUCT RESEARCH
https://doi.org/10.1080/14786419.2018.1512995
SHORT COMMUNICATION
A new flavanone glycoside isolated from
Tournefortia sibirica
a
ꢀ
b
ꢀ
a
c
a
Shengbao Diao , Mei Jin , Chun Shi Jin , Cheng-Xi Wei , Jinfeng Sun , Wei
a
a
Zhou and Gao Li
a
Key Laboratory of Natural Resources of Changbai Mountain and Functional Molecules, Ministry of
b
Education, Yanbian University College of Pharmacy, Yanji, China; Department of Pharmacy, Yanbian
University Hospital, Yanji, China; Medical College, Inner Mongolia University for Nationalities,
c
Tongliao, China
ABSTRACT
ARTICLE HISTORY
A new flavanone glycoside, (2S)-dihydrooroxylin A 7-O-[b-D-
apiosyl(1fi2)]-b-D-glucoside (1), and four known compounds (2–5)
were isolated from Tournefortia sibirica L. The chemical structures
of these compounds were determined by 1 D and 2 D NMR and
HR-ESI-MS spectra, and results were compared with data from the
literature. These five compounds (1–5) were isolated from the fam-
ily Boraginaceae for the first time. Anti-inflammatory effects of
compounds (1–5) were evaluated in terms of inhibition of produc-
tion of NO, TNF-a, and IL-6 in LPS-induced RAW 264.7 cells.
Received 29 June 2018
Accepted 13 August 2018
KEYWORDS
Tournefortia sibirica L.;
Boraginaceae; flava-
none glycoside
CONTACT Wei Zhou
These authors contributed equally to the work.
zhouwei8452@163.com; Gao Li
gli@ybu.edu.cn
ꢀ
Supplemental data for this article can be accessed at https://doi.org/10.1080/14786419.2018.1512995.
ß 2018 Informa UK Limited, trading as Taylor & Francis Group

2
S. DIAO ET AL.
1. Introduction
Tournefortia sibirica L. (Boraginaceae) is a salt-secreting halophyte that is mainly pro-
duced in the Hebei, Shandong, Henan, Gansu provinces in northeastern China, and
Mongolia, Korea, and Japan. The whole T. sibirica plant has been used in Mongolian
traditional folk medicine for the treatment of scrofula, eczema, sores, and ulcers (Zhu
1989). Valuable phytochemical investigations of this plant resulted in the extraction
and isolation of essential oils (Morteza-Semnani et al. 2008; Gao et al. 2015), polysac-
charides (Zhang et al. 2015), alkaloids (Hikichi et al. 1980), lignans (Song et al. 1992,
1996), flavonoids, steroids, and triterpenoids (Song et al. 1996). The present study
describes the isolation, structural elucidation, and anti-inflammatory activities of a new
flavanone glycoside (1) and four known compounds (2–5) from the whole plant of T.
sibirica on the basis of spectroscopic studies, and comparisons with literature data.
2. Results and discussion
Compound 1 was obtained as a yellow amorphous powder, and its molecular formula
was determined to be C H O by HR-ESI-MS, which gave a m/z 581.1903 for
2
7 32 14
þ
[
M þ H] (calcd. for C H O , 581.1870). Acidic hydrolysis of 1 gave D-glucose and D-
2
7 33 14
1
apiose. The H NMR spectrum of 1 showed signals for a mono-substituted benzene
0
0
0
0
ring at d 7.56 (2H, d, J ¼ 7.2 Hz, H-2 , 6 ), d 7.42 (2H, t, J ¼ 7.2 Hz, H-3 , 5 ), 7.37 (1H, t,
H
0
J ¼ 7.2 Hz, H-4 ) attributed to benzene ring B, one singlet aromatic proton at d 6.76
H
0
00
(
5
1H, s, H-8), and two anomeric proton signals at d 6.59 (1 H, d, J ¼ 1.5 Hz, H-1 ), d
H
H
0
0
.77 (1H, d, J ¼ 7.8 Hz, H-1 ), which indicated a b-configuration of the glucosyl moiety.
0
00
The apiose unit was also determined to have a b-configuration at C-1 by comparison
1
3
of the C NMR data of the apiose of 1 with those of methyl a-D- and b-D-apiofurano-
sides (Ishii and Yanagisawa 1998; Lei et al. 2008). Extra sugar signals at d 4.06–5.39,
H
an oxygenated methine proton at dH 5.39 (1H, dd, J ¼ 13.2, 3.1 Hz, H-2), and a
13
methoxyl proton at dH 4.10 (3H, s, 6-OCH ) were also observed. The C-NMR and
3
DEPT spectra exhibited a total of 27 carbon signals, including a carbonyl carbon at dC
1
1
97.6 (C-4), two benzene rings (12 carbons) at d 159.7 (C-7), 158.9 (C-9), 156.3 (C-5),
C
0
0
0
0
0
0
39.7 (C-1 ), 132.0 (C-6), 129.4 (3 , 5 ), 129.3 (C-4 ), 127.1 (C-2 , 6 ), 104.6 (C-10) and 95.5
000 00 000 00
C-8), two sugar moieties at d 111.0 (C-1 ), 100.0 (C-1 ), 81.1 (C-3 ), 79.2 (C-5 ), 79.0
C
(
(
0
0
000
00
000
00
000
00
C-3 ), 78.3 (C-2 ), 77.9 (C-2 ), 75.9 (C-4 ), 71.3 (C-4 ), 66.2 (C-5 ) and 62.3 (C-6 ), an
oxygenated carbon signal at d 79.9 (C-2), and a methoxyl group at d 61.3 (6-OCH ).
C
C
3
All the above information suggested that compound 1 was similar to (2S)-dihydroorox-
ylin A- 7-O-[b-D-apiosyl(1fi6)]-b-D-glucoside (Yang et al. 2014), except for the position
0
0
of the apiose unit which was linked to the C-2 of the D-glucoside in 1. This conclu-
0
00
sion was further supported by an HMBC correlation between H-1 (d 6.59) of apiose
H
0
0
and C-2 (dC 77.9) of D-glucoside, which suggested the apiose unit was located
0
0
at C-2 (Figure S1). The absolute configuration of C-2 was determined to be the S-
configuration by comparison of the optical rotation value with (2S)-dihydrooroxylin
A-7-O-[b-D-apiosyl(1fi6)]-b-D-glucoside (Yang et al. 2014). Thus, the structure of
compound 1 was elucidated as (2S)-dihydrooroxylin A 7-O-[b-D-apiosyl(1fi2)]-
b-D-glucoside.

NATURAL PRODUCT RESEARCH
3
Figure 1. The structures of compounds 1–5.
0
0
The four known compounds (2–5) were identified as 2 -O-acetyl-7-O-methylvitexin
(
2
2) (Mbing et al. 2014), 5-hydroxy-7-methoxy-8-C-b-glucosylflavone (3) (Moreira et al.
000), spinacetin 3-O-b-glucopyranoside (4) (Ito et al. 2000) and 9 -methoxydehydrodi-
0
coniferyl alcohol 4-O-b-D-glucopyranoside (5) (Iizuka et al. 2001) (Figure 1).
Compounds 1–5 were assayed for their inhibitory effects on the production of NO,
TNF-a and IL-6 in LPS-induced RAW264.7 cells. Compounds 1–5 did not affect cell via-
bility at 100 lM (Figure S9). We found that LPS-induced production of NO, TNF-a and
IL-6 was substantially suppressed by compounds 1–5 in a dose-dependent manner, all
of which showed strong anti-inflammatory activities at 30 and 100 lM. In particular,
compounds 1 and 3–5 exhibited inhibitory activity against NO and IL-6 production
even at 10 lM (Figures S10, S12). Compounds 2–5 displayed significant inhibitory
effects on LPS-induced production of TNF-a at 10 lM (Figure S11).
3. Conclusion
In this study, a new flavanone glycoside (1) and four known compounds (2–5) were iso-
lated from T. sibirica, supporting the need for further research to reveal new chemical
constituents that remain undiscovered in this species. The bioactivity data showed that
some compounds from T. sibirica could inhibit the production of the pro-inflammatory
cytokines NO, TNF-a and IL-6 in LPS-stimulated RAW 264.7 cells. These compounds
represent potential drug candidates for the treatment of inflammatory diseases.
Acknowledgements
This work was supported by the National Natural Science Foundation of China under grant
[numbers 81660699, 81660579 and 81760627]. We thank Alison McGonagle, PhD, from Liwen
Bianji, Edanz Editing China, for editing the English text of a draft of this manuscript
Disclosure statement
No potential conflict of interest was reported by the authors.

4
S. DIAO ET AL.
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