Constituents from Apium graveolens and their anti-inflammatory effects

Article abstract of DOI:10.1080/10286020.2017.1381687

A phthalide glycoside, (3R, 4R)-4-O-β-D-glucopyranosyl-senkyunolide (1), and a megastigmane glycoside, (6S, 7R)-3-oxo-megastigma-4, 8-dien-7-O-β-D-glucoside (2), along with two known aglycones (3–4), were isolated from the 70% EtOH extract of fresh whole grass of Apium graveolens L. Their structures were elucidated by extensive spectroscopic analysis. All of these compounds were tested for their inhibitory effects on nitric oxide (NO) production in the RAW 264.7 macrophages. Among them, compounds 3 and 4 showed potent inhibitory activity against LPS-induced nitric oxide production in RAW 264.7 macrophages, with IC₅₀ values of 24.0?±?2.1?μM and 28.6?±?2.4?μM, respectively.

Full text of DOI:10.1080/10286020.2017.1381687

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Journal of Asian Natural Products Research
ISSN: 1028-6020 (Print) 1477-2213 (Online) Journal homepage: http://www.tandfonline.com/loi/ganp20
Constituents from Apium graveolens and their
anti-inflammatory effects
Li-Han Zhu, Tian-Hui Bao, Yue Deng, Hua Li & Li-Xia Chen
To cite this article: Li-Han Zhu, Tian-Hui Bao, Yue Deng, Hua Li & Li-Xia Chen (2017):
Constituents from Apium graveolens and their anti-inflammatory effects, Journal of Asian Natural
Products Research, DOI: 10.1080/10286020.2017.1381687
To link to this article: http://dx.doi.org/10.1080/10286020.2017.1381687
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Date: 04 October 2017, At: 21:59

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Journal of asian natural Products research, 2017
https://doi.org/10.1080/10286020.2017.1381687
Constituents from Apium graveolens and their
anti-inflammatory effects
Li-Han Zhua, Tian-Hui Baoa, Yue Denga, Hua Lia,b and Li-Xia Chena
aKey laboratory of structure-Based drug design & discovery, school of traditional chinese Materia Medica,
Wuya college of innovation, Ministry of education, shenyang Pharmaceutical university, shenyang 110016,
china; bschool of Pharmacy, tongji Medical college, huazhong university of science and technology, Wuhan
430030, china
ABSTRACT
ARTICLE HISTORY
received 29 June 2017
accepted 14 september 2017
A phthalide glycoside, (3R, 4R)-4-O-β-D-glucopyranosyl-senkyunolide
(1), and a megastigmane glycoside, (6S, 7R)-3-oxo-megastigma-4,
8-dien-7-O-β-D-glucoside (2), along with two known aglycones
(3–4), were isolated from the 70% EtOH extract of fresh whole grass
of Apium graveolens L. Their structures were elucidated by extensive
spectroscopic analysis. All of these compounds were tested for their
inhibitory effects on nitric oxide (NO) production in the RAW 264.7
macrophages. Among them, compounds 3 and 4 showed potent
inhibitory activity against LPS-induced nitric oxide production
in RAW 264.7 macrophages, with IC50 values of 24.0 2.1 μM and
28.6 2.4 μM, respectively.
KEYWORDS
Apium graveolens; phthalide
glycoside; megastigmane
glycoside; nitric oxide
O
OH
O
OH
O
O
HO
HO
O
HO
HO
O
OH
OH
O
2
1
1. Introduction
e genus (Apium) with 20 species is distributed widely in temperate regions around the
world, and two species were found in China. Apium graveolens has been used as a well-
known vegetable, and most of the people like it, which contains flavonoids [1,2], coumarins
[3–6], phthalides [7–9], sesquiterpenes [10], volatile oil [11,12], and so on. A lot of studies
showed that the crude extract of A. graveolens possessed prominent anti-inflammatory,
anti-hypertensive, hypolipidemic, antioxidant, anti-cancer, and other effects [13–17].
CONTACT li-Xia chen
syzyclx@163.com; hua li
li_hua@hust.edu.cn
supplemental data for this article can be accessed at https://doi.org/10.1080/10286020.2017.1381687.
© 2017 informa uK limited, trading as taylor & francis Group

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2
L.-H. ZHU ET AL.
In order to find the anti-inflammatory material basis of A. graveolens, the EtOH extract
of the whole grass of this plant was investigated, and two new compounds, along with
two known compounds, were isolated. eir structures were elucidated by comprehensive
spectroscopic analysis. All of these compounds were tested for their inhibitory effects on
nitric oxide (NO) production in RAW 264.7 macrophages.
2. Results and discussion
e fresh whole grass of A. graveolens was cut into pieces and extracted with 70% EtOH. e
extract was suspended in water and then partitioned with petroleum ether (PE) and ethyl
acetate (EtOAc) successively. en, the EtOAc layer was separated by silica gel, Sephadex
LH-20, ODS open column chromatography (CC), and HPLC to produce two new com-
pounds, a phthalide glycoside, (3R, 4R)-4-O-β-D-glucopyranosyl-senkyunolide (1), and
a megastigmane glycoside, (6S, 7R)-3-oxo-megastigma-5,8-dien-7-O-β-D-glucoside(2),
along with two known aglycones, sedanolide (3) [18] and (3S)-3-hydroxy-megastigma-
5,8-dien-7- one (4) [19] (Figure 1).
Compound 1 was isolated as white powder (MeOH). Molish reaction was positive, and
glucose was detected afer acid hydrolysis. e molecular formula C18H26O8 was deduced by
HR-ESI-MS data at m/z 393.1527 [M+Na]+, with six degrees of unsaturation. e anomeric
proton signal at δH 4.42 (1H, d, J = 7.8 Hz) showed the glucose with β-anomeric configu-
ration. e signals at δH 1.64 (1H, dd, J = 15.2, 6.7 Hz), 2.10–2.16 (1H, m), 1.37–1.42 (2H,
m), 1.37–1.42 (2H, m), and 0.95 (3H, t, J = 7.1 Hz) in the 1H-NMR (Table 1) spectrum, in
combination with the 1H-1H COSY correlations (Figure 2) of H-3 with H-1′, H-1′ with H-2′,
H-2′ with H-3′, and H-3′ with H-4′ indicated that the presence of a n-butyl and two olefinic
Figure 1. structures of compounds 1–4.

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JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH
3
1
Table 1. h- and 13c-nMr spectroscopic data for compounds 1 and 2 in cd3od (at 300 and 75 Mhz,
respectively)
1
2
Position
δC
δH (J in Hz)
δC
δH (J in Hz)
1
2
173.5
37.2
48.4
2.00, d (16.8)
2.40, d (16.8)
3
4
5
83.9
69.1
31.9
5.43, dd (7.5, 3.1)
4.80–4.87, m
2.76, br dd (15.6, 8.8)
2.88, dt (15.6, 4.5)
6.14, dt (9.5, 4.0)
6.23, br d (9.5)
202.1
126.2
166.0
5.84, br s
6
7
7a
3a
8
116.2
130.8
127.0
159.9
56.8
77.1
2.64, d (8.9)
4.30–4.38, m
138.3
128.9
21.2
23.9
28.2
27.7
102.5
5.73, dd (15.6, 6.5)
5.56–5.64, m
1.25, d (6.3)
1.90, s
9
10
11
12
13
1′
0.99, s
0.97, s
4.31, d (7.8)
32.7
1.64, dd (15.2, 6.7)
2.10–2.16, m
1.37–1.42, m
1.37–1.42, m
0.95, t (7.1)
2′
3′
4′
5′
6′
28.1
23.7
14.4
75.3
78.2
71.6
78.0
62.8
3.11–3.20, m
3.11–3.20, m
3.23–3.34, m
3.23–3.34, m
3.79, dd (11.8, 2.0)
3.64, dd (11.8, 5.1)
1″
2″
3″
4″
5″
6″
103.5
74.9
78.2
71.5
78.0
62.7
4.42, d (7.8)
3.13, t (7.8)
3.33–3.36, m
3.28–3.31, m
3.32–3.39, m
3.71, dd (11.6, 6.9)
3.89, br d (11.6)
Figure 2. Key correlations of 1h-1h cosY, hMBc, and noesY of compounds 1 and 2.