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Phytochemical and pharmacological progress on the genus Syringa

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Genus Syringa, belonging to the Oleaceae family, consists of more than 40 plant species worldwide, of which 22 species, including 18 endemic species, are found in China. Most Syringa plants are used in making ornaments and traditional medicines, whereas some are employed for construction or economic use. Previous studies have shown that extracts of Syringa plants mainly contain iridoids, lignans, and phenylethanoids that have antitumor, antihypertensive, anti-oxidant, and anti-inflammatory activities. This study reviews phytochemical and pharmacological progress on Syringa in the recent 20 years and discusses the future research prospects to provide a reference in further promotion and application of the genus. Graphical Abstract Phytochemical and pharmacological progress on the genus Syringa
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REVIE W Open Access
Phytochemical and pharmacological progress on
the genus Syringa
Guozhu Su
1,2
, Yuan Cao
1,2
, Chun Li
1
, Xuelong Yu
1,2
, Xiaoli Gao
1
, Pengfei Tu
1
and Xingyun Chai
1*
Abstract
Genus Syringa, belonging to the Oleaceae family, consists of more than 40 plant species worldwide, of which 22
species, including 18 endemic species, are found in China. Most Syringa plants are used in making ornaments and
traditional medicines, whereas some are employed for construction or economic use. Previous studies have shown that
extracts of Syringa plants mainly contain iridoids, lignans, and phenylethanoids that have antitumor, antihypertensive,
anti-oxidant, and anti-inflammatory activities. This study reviews phytochemical and pharmacological progress on
Syringa in the recent 20 years and discusses the future research prospects to provide a reference in further promotion
and application of the genus.
Keywords: Syringa, Oleaceae, Iridoid, Lignan, Phenylethanoid, Bioactivities, Review
Introduction
Plants belonging to the family Oleaceae, which con sists
of 27 genera and 400 species worldwide, have important
applications in the daily life of people living in developing
countries. Plants of many well-known genera, including
Forsythia, Syringa,andOsmanthus, have been widely used
for medicinal and industrial purposes. For instance, the
stems and roots of S. pinnatifolia var. alashanensis is the
major composition of atraditional formula Ba wei chen-
xiang powder that is used for treatment of asthma, cardio-
palmus, and angina [1].
Most Syringa plants are deciduous shrubs and arbors
and include more than 40 species distributed around
Europe and Asia [2]. At present, 22 species are found in
China, of which 18 are endemic species that are mainly
distributed in the southwestern part of Sichuan, Yunnan,
Tibet, and other Northwestern regions. Many Syringa spe-
cies, such as S. chinensis, S. meyeri,andS. pekinensis,are
used for making ornaments. Flowers of S. oblata and
S. reticulata var. mandshurica are an ideal source of aroma
oils or nectar. Some Syringa plants are also used for con-
struction purposes or for manufacturing furniture [1].
Previous phytochemical studies on Syringa species
have revealed the presence of more than 140 secondary
metabolites, including iridoids, lignans, phe nylethanoids,
their glycosides, minor organic acids, and essential oils
[3,4]. Modern pharmacological studies have shown the
bioactivities of these metabolites, such as antitumor, an-
tihypertensive, anti-oxidant, anti-inflammatory activities,
and so on [5]. However, a systematic review of these
studies has not been performed to date. This review
summarizes the phytochemical and pharmacological
progress on Syringa to date by focusing on its chemical
classification, structural features, and biological and
pharmacological applications to prov ide information for
further research on this genus.
Chemical constituents
Previous studies have reported that extracts of Syringa
plants contain iridoids ( 1 46), lignans (4780), phenyl-
propanoids (81105), phenylethanoids (106121 ), and
other compounds (122142). The structures of these
compounds are shown in Figures 1, 2, and 3 and related
information are listed in Tables 1, 2, and 3.
Iridoids
Iridoids are one of the most important natural compounds
that are widely distributed in various plant families such as
Plantaginaceae, Rubiaceae, and Scrophulariaceae [6]. Iri-
doids are extensively present in almost all Syringa species
and have antitumor, antihypertensive, anti-inflammatory,
anti-oxidant, and antifungal activities. In addition, iridoids
* Correspondence: xingyunchai@yeah.net
1
Modern Research Center for Traditional Chinese Medicine, Beijing University
of Chinese Medicine, 11 North 3rd Ring Road, Chaoyang District, Beijing
100029, P. R. China
Full list of author information is available at the end of the article
© 2015 Su et al.; licensee Springer. This is an Open Access article distributed under the terms of the Creative Commons
Attribution License (http://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and
reproduction in any medium, provided the original work is properly credited.
Su et al. Chemistry Central Journal (2015) 9:2
DOI 10.1186/s13065-015-0079-2
play an important role in defense mechanism of ants [7].
Among all the iridoids reported in this genus, secoiridoids
are the most abundant and have been shown to have anti-
tumor activity. To date, 46 iridoids (146) have been de-
scribed, including secoiridoids (130 and 4044), eight
typical iridoids (3239), and three minor dimers (31, 45,
and 46). Most iridoids exist as glycosides and are
mainly produced by the glycosylation of glucose and
galactose. Syrin ga iridoids are generally substituted by
various acid fragments and phenolic moieties such a s
1-O-cinnamoyl-β-D-glucopyranosyl, p-hydroxphenethyl,
3, 4-dihydroxy-phenethyl, and caffeic acid, which contrib-
ute to their low polarity. Syringa iridoids have antitumor
(33 and 40) [8,9], antihypertensive (4), and anti-oxidant
(4 and 31) activities [10].
Lignans
Lignans are another major compounds in this genus, par-
ticularly in S. komarowii [27], S. pubescens [3], S. reticulata
[10], S. velutina [28], S. patula [5], S. vulgaris [29], S. pin-
natifolia var. alashanensis [30,31], and S. reticulata var.
mandshurica [32]. Syringa species have 34 lignans and
their glycosides (4780), including monoepoxylignans
(4760, 62) and their dimers (63 and 64), neolignans (61,
7374), cyclolignans (65 and 66), simple lignans (6772),
and bisepoxylignans (7580). Lignans also exhibit
many bioactivities. For e xample, compound 50 ha s
anti-oxidant a ctivity [10]; compounds 57 and 58 have
antifungal activities [32]; and compound 75 ha s signifi-
cant cytotoxic, antihypertensive, anti-inflammatory,
and anti-oxidant activit ies [5].
Figure 1 The structures of iridoids from the genus Syringa.
Su et al. Chemistry Central Journal (2015) 9:2 Page 2 of 12
Other compounds
Phenylethanoids ( 81105), phenylpropanoids and their
analogues (106121), flavonoids (122128), sesquiter-
penes (129 and 130), and other minor compounds have
been described in Syringa plants. Of these, phenyletha-
noids are predominant, particularly in S. reticulata
[10,12,35], S. vulgaris [29], S. pubescens [3], S. oblata var.
alba [36], S. reticulata var. mandshurica [35], S. afghanica
[13], and S. komarowii [27]. Sesquiterpenes (129 and 130)
are present in the stems of S. pinnatifolia var. alashanensis
[37]. These miscellaneous compounds have cytotoxic,
anti-inflammatory, antihypertensive, anti-oxidant, and an-
tifungal properties.
Besides the abovementioned compounds, Syringa plants
contain essential oils that form the most important constit-
uents not only because of their economic utility but also
because of their potential medicinal value as antimicrobial,
antipyretic, and antiviral agents. Multiple analytical
techniques such as headspace solid-phase microextrac-
tion, gas chromatographymass spectrometry (GCMS),
GCMS coupled with heuristic evolving latent projec-
tions, moving subwindow searching, nuclear magnetic
resonance spectroscopy, and X-ray single-crystal diffrac-
tion analysis have been used to identify essential oils from
fresh flowers of S. oblata var. alba. For instance, 39 vola-
tile oil constituents were identified, including four charac-
teristic isomers of lilac alcohols (lilac alcohols AD) and
lilac aldehydes AD [38]. Ninety-five components, includ-
ing 15 terpenes, 14 oxygenated terpenes, 10 aromatic com-
pounds, and 13 n-alkanes were quantitatively analyzed
from S. oblata buds [39]. Forty-nine components were de-
scribed from essential oil of S. pubescens flowers, most of
which are monoterpenes and sesquiterpenes [40]. Thirty-
four volatile oil components, accounting for around 64.7%
(zerumbone) of the toil oil, were identified from roots and
barks of S. pinnatifolia var. alashanensis [4]. These data
imply that Syringa
plants could be considerably different
from each other in terms of their essential oil components.
Pharmacological activities
Various crude extracts and isolated compounds from
Syringa plants have shown significant antitumor, antihy-
pertensive, anti-inflammatory, anti-oxidant, and antifun-
gal activities.
Figure 2 The structures of lignans from the genus Syringa.
Su et al. Chemistry Central Journal (2015) 9:2 Page 3 of 12
Figure 3 The structures of other type of compounds from the genus Syringa.
Su et al. Chemistry Central Journal (2015) 9:2 Page 4 of 12
Table 1 Iridoids from the genus Syringa
No Compound Part of plants Source Reference
1 Isoligustroside leaves S. vulgaris [11]
2 Isooleuropein leaves S. vulgaris [11]
3 Oleoside 11-methyl ester flowers, leaves and floral buds S. pubescens [3,5]
S. patula
4 Oleuropein flowers, leaves, barks and floral buds S. pubescens [3,5,8,10,12-14]
S. reticulata, S. dilatata,
S. velutina, S. afghanica,
S. oblata var. alba, S. patula
5 Neooleuropein leaves S. vulgaris [15]
6 8(E)-Ligstroside flowers, leaves and barks S. pubescens, S. reticulata,
S. dilatata, S. afghanica
[3,8,10,13]
7 8(E)-Nüzhenide leaves S. reticulata [16]
8 Safghanoside A leaves S. afghanica [13]
9 Safghanoside B leaves S. afghanica [13]
10 Safghanoside C leaves S. afghanica [
13]
11 Safghanoside D leaves S. afghanica [13]
12 Safghanoside E leaves S. afghanica [13]
13 Safghanoside F leaves S. afghanica [13]
14 Formoside leaves S. afghanica [13]
15 Fraxiformoside leaves S. afghanica [13]
16 2''-epi-frameroside leaves S. afghanica [13]
17 1'''-O-β-D-glucosylformoside leaves S. afghanica [13]
18 1'''-O-β-D-glucosylfraxiformoside leaves S. afghanica [13]
19 Lilacoside barks and leaves S. vulgaris [17,18]
20 Fliederoside barks and leaves S. vulgaris [17,18]
21 8(Z)-Ligstroside leaves S. reticulata [16]
22 8(Z)-Nüzhenide leaves S. reticulata [16]
23 Oleoside dimethyl ester leaves S. afghanica [13]
24 10-Hydroxyoleuropein flowers and leaves S. pubescens
[3]
25 10-Hydroxyoleoside dimehyl ester flowers and leaves S. pubescens [3]
26 Secologanoside 7-methyl ester leaves S. reticulata [19]
27 Grandifloroside 11-methyl ester flowers and leaves S. pubescens [3]
28 8-Epikingiside barks S. vulgaris [20]
29 Syrveoside A leaves S. velutina [21]
30 Syrveoside B leaves S. velutina [21]
31 Jaspolyoside barks S. reticulata [10]
32 Syringopicroside leaves S. dilatata, S. vulgaris,
S. oblata, S. reticulata
[8,16,19,22,23]
33 Syringopicroside B leaves S. vulgaris [9]
34 3-O-β-D-glucopyranosylsyring-opicroside leaves S. reticulata [16]
35 4-O-β-D-glucopyranosylsyring-opicroside leaves S .reticulata [16]
36 6-O-
α-D-glucopyranosylsyring-opicroside leaves S. reticulata [16]
37 6-O-α-D-galactopyranosylsyring-opicroside leaves S. reticulata [19]
38 Syringopicrogenin C seeds S. oblata [24]
39 Syringopicrogenin A seeds and crust S. oblata [24,25]
Su et al. Chemistry Central Journal (2015) 9:2 Page 5 of 12
Antitumor activity
Cytotoxic activities of crude extracts and chemicals ob-
tained from Syringa plants have been extensively evalu-
ated against various tumor cell lines. Aqueous extracts
from the flowers and leaves of S. pubescens inhibited the
growth of L2215 (hepatitis B virus) cells, with a 50% in-
hibitory concentration (IC
50
) value of 78 μg/mL [51].
Hydrolysis of isoligustroside (1) and isooleuropein (2)
were assayed using a disease-oriented panel of 39 human
cancer cell lines. The results showed that the hydrolysis
product of compound 2 had moderate cytotoxic activity
against lung cancer cell lines DMS273 [log GI
50
= 5.19
(6.4 μM)] and DMS114 [log GI
50
= 5.06 (8.7 μM)]. Pre-
liminary analysis of structureactivity relationship sug-
gested that C-5-OH plays an important role in this
cytotoxic activity [11]. Isooleoacteoside (40) showed
weak cytotoxicity against LOX-IMVI melanoma cell line,
with GI
50
value of 16 μM, and syringopicroside B (33)
showed weak cytotoxic activity against N CI-H522 lung
cancer cell line, with GI
50
value of 13 μM [9]. MTT assay
used to assess the cytotoxicities of syringaresinol (78)
and oleoside 11-methyl ester (3) showed that compound
78 had a strong dose-dependent effect on HepG2 cell
line, with an IC
50
value of 94.6 μM, and compound 3
has a doseresponse curve of low slope, with a high IC
50
value of 186.5 μM, compared with positive controls
dexametha sone (IC
50
14.2 μM) and paclitaxel (IC
50
700
nM). However, compound 78 was cytotoxic e ven at the
lowest concentration of 29.9 μM. β-Amyrin acetate
(139) showed weak cytotoxicity against A2780 human
ovarian cancer and HepG2 cell lines [5]. Oleuropein (4)
and 2-(3, 4-dihydroxy)-phenylethyl-β-D-glucopyranoside
(83) showed evident cytotoxicities against P-388, L-1210,
SNU-5, and HL-60 cell lines, with IC
50
values varying
from 8.5 to 139.8 μM [12]. Verbascoside (86) showed
moderate cytotoxic activity against SNB-75 (brain cancer)
and SNB-78 cell lines, with GI
50
values of 7.4 and 7.7 μM,
respectively [9]. A pharmacokinetic study showed that
compound 86 interacted with the catalytic domain of PKC
and acted as a competitive inhibitor of adenosine triphos-
phate (K
i
=22μM) and non-competitive inhibitor of
phosphate acceptor (histone III). Because 83 is one part of
86 in its molecular structure, the cytotoxic effect could be
attributed to 3, 4-dihydroxyphenylethoxy moiety, which
may act as a competitive inhibitor to the catalytic domain
of PKC. Therefore, 83 is a potentially essential skeleton of
most cytotoxic phenylethanoid glycosides [12].
Hypotensive activity
Syringin (110) and kaempferol-3-O-rutinoside (125)
showed antihypertensive activity. Intravenous injection
of 10 mg/kg of compound 86 significantly decreased sys -
tolic, diastolic, and mean arterial blood pressure in
Pentothal-anesthetized rats. Moreover, the depressor ef-
fect of compound 86 was independent of muscarinic
and histaminergic receptors because it did not block the
effect of atropine (an antimuscarinic agent) and chlor-
pheniramine/cimetidine (antihistaminergic agents) [36].
In vitro studies showed that oleuropein (4) significantly
lowered blood pressure. It is interesting to note that an-
tihypertensive effect of compound 4 (33% at 30 mg/kg
dose) on the blood pressure of anesthetized rats was
similar to that of compound 86 (39.04% ± 2.38% at 10
mg/kg dose) [14,36], which is probably because of the
similarity in their structures, with both possessing the
same aromatic fragment having two hydroxy groups.
Anti-inflammatory activity
Iridoid glycosides (IGs) exerted obvious anti-inflammatory
effects on ulcerative colitis in vivo by inhibiting relative
proinflammatory cytokines [53]. IGs significantly ame-
liorated macrosco pic damages and histological c hanges ,
reduced the activity of myeloperoxida se, and strongly
inhibited epithelial cell apoptosis. Moreover, IGs markedly
decreased the levels of tumor necrosis factor-α,interleukin-
8, cyclooxygenase-2, and transforming growth factor-β1in
colonic tissues in a dose-dependent manner. Moreover, ef-
fects of IGs (160 and 240 mg/kg) were superior to those of
positive control salicylazosulfapyridine (150 mg/kg). Fur-
thermore, IGs significantly blocked NF-κB signaling by
inhibiting inflammatory bowel phosphorylation/degrad-
ation and inhibitor kappa B kinase β activity; downregu-
lated protein and mRNA expressions of Fas/FasL, Bax, and
caspase-3; and activated Bcl-2 in intestinal epithelial cells
Table 1 Iridoids from the genus Syringa (Continued)
40 Isooleoacteoside leaves S. vulgaris [9]
41 Oleoacteoside leaves S. reticulata [9,26]
42 Oleoechinacoside leaves S. reticulata [9,26]
43 Reticuloside barks S. reticulata [10]
44 Jasminoside whole plant S. komarowii [27]
45 Safghanoside H leaves S. afghanica [13]
46 Safghanoside G leaves S. afghanica [13]
Su et al. Chemistry Central Journal (2015) 9:2 Page 6 of 12
[53,54]. β-Amyrin acetate (139) and syringaresinol (78)ata
dose of 20 μg/mL evidently inhibited lipopolysaccharide-
induced nitric oxide (NO) production, with inhibition rates
of 49.97% and 33.21%, respectively [5].
Liver-protective and cholagogic effects
Crude extract of Syringa species , interferon ( IFN), and
an injection o f Gan-Yan-Ling were compared to
evaluate their liver-protective e ffect s on the sur vival
rates o f HepG2.215 cells and se cretion of hepatitis B
surface antigen (HBsAg) and HBeAg. The results indi-
cated that all the three assayed drugs may suppress the
secretion of HBsAg and HBeAg from HepG2.215 cells
in a dose-dependent manner, with the effect of crude
extract of Syringa being intermediate those of IFN and
Gan-Yan-Ling. Therefore, extracts of Syringa plant
Table 2 Lignans from the genus Syringa
No Name Part of plant Source Reference
47 ()-Olivil whole plant S. komarowii [27]
48 Olivil 4-O-β-D-glucopyranoside barks S. reticulata, S. patula [10]
49 Olivil 4''-O-β-D-glucopyranoside barks S. reticulata [27]
50 Armandiside barks S. reticulata [10]
51 Syripinnalignan A roots and stems S. pinnatifolia var. alashanensis [31]
52 Syripinnalignan B roots and stems S. pinnatifolia var. alashanensis [31]
53 (8R,8R,9S)-4-4-dihydroxy-3, 3, 9-trimethoxy-9-9-epoxylignan roots and stems S. pinnatifolia var. alashanensis [30]
54 (8R,8R,9R)-4-4-dihydroxy-3, 3, 9-trimethoxy-9-9-epoxylignan roots and stems S. pinnatifolia var. alashanensis [30]
55 (8S,8S
,9R)-4-4-dihydroxy-3, 3, 9-trimethoxy-9-9-epoxylignan roots and stems S. pinnatifolia var. alashanensis [30]
56 (8S,8S,9S)-4-4-dihydroxy-3, 3, 9-trimethoxy-9-9-epoxylignan roots and stems S. pinnatifolia var. alashanensis [30]
57 Mandshuricol A leaves S. reticulata var. mandshurica [32]
58 Mandshuricol B leaves S. reticulata var. mandshurica [32]
59 (+)-Lariciresinol seeds crust S. oblata [25]
60 (+)-Lariciresinol 4-O-β-D-glucopyranoside barks S. vulgaris [29]
61 Balanophonin roots and stems S. pinnatifolia var. alashanensis [30]
62 (+)-Lariciresinol 4-O-β-D-glucopyran
-osyl-(13)-β-D-glucopyranoside
leaves S. reticulata [19]
63 Syripinnalignin A roots and stems S. pinnatifolia var. alashanensis [33
]
64 Syripinnalignin B roots and stems S. pinnatifolia var. alashanensis [33]
65 Cycloolivil 6-O-β-D-glucoside barks S. reticulata [10]
66 (+)-Cycloolivil whole plant S. komarowii [27]
67 ()-Secoisolariciresinol stems S. pinnatifolia var. alashanensis [30,31]
68 PiperphilippininVI roots and stems S. pinnatifolia [30]
69 Dihydrocubebin roots and stems S. pinnatifolia var. alashanensis [30]
70 Syripinnalignan C roots and stems S. pinnatifolia var. alashanensis [34]
71 Syripinnalignan D roots and stems S. pinnatifolia var. alashanensis [34]
72 Syripinnalignan E roots and stems S. pinnatifolia var. alashanensis [34]
73 (7S,8R)-Guaiacylglycerol-8-O-4-sinapyl
ether 9-O-β-D-glucopyranoside
leaves S. velutina [28]
74 (7S,8
R)-Syringylglycerol-8-O-4-sinapyl
ether 9-O-β-D-glucopyranoside
leaves S. velutina [28]
75 Pinoresinol-4-O-β-monoglycoside barks S. reticulata [10]
76 Syringaresinol-4-O-bis-β-D-monoglucoside barks S. reticulata [10]
77 Syringaresinol-4, 4''-O-bis-β-D-glucoside barks S. reticulata [10]
78 Syringaresinol floral buds, flowers and leaves S. patula, S. pubescens [3,5]
79 (+)-Medioresinol-4-O-glucoside floral buds S. patula [5]
80 ()-Pinoresinol roots and stems S. pinnatifolia var. alashanensis [30]
Su et al. Chemistry Central Journal (2015) 9:2 Page 7 of 12
Table 3 Other type of compounds from the genus Syringa
No Name Part of plant Source Reference
81 Isosyringalide leaves S. reticulata [41]
82 Forsythiaside barks S. vulgaris [29]
83 2-(3, 4-dihydroxy)-phenylethyl-β-D-glucopyranoside barks S. reticulata [10,12]
84 cis-Echinacoside leaves S. reticulata [35]
85 Isoverbascoside leaves S. pubescens [3]
86 Verbascoside leaves S. pubescens, S. oblata var. alba, S. vulgaris [3,9,29,14,36]
87 Echinacoside barks, leaves and flowers S. pubescens, S. reticulata [3,29,42]
S. vulgaris
88 Forsythoside B leaves S. reticulata var. mandshurica [35]
89 Salidroside barks S. reticulata [10]
90 3-O-β-D-glucopyranosysalidroside leaves S. reticulata var. mandshurica [35]
91 2-(3, 4-dihydroxyphenyl) ethanol leaves S. pubescens [
3]
92 Osmanthuside F leaves S. reticulata [35]
93 (S)-(+)-2-(3, 4-dihydroxyphenyl)-2-ethoxylethanol leaves S. reticulata var. mandshurica [43]
94 (S)-(+)-2-(3, 4-dihydroxyphenyl)-2-acetoxyethanol leaves S. reticulata var. mandshurica [43]
95 Decaffeoylacteoside leaves S. reticulata [35]
96 Syringalide B leaves S. reticulata [41]
97 Poliumoside leaves S. afghanica [13]
98 2-(4-hydroxypenyl)-ethyl behenate whole plant S. komarowii [27]
99 2-(4-hydroxypenyl)-ethyl tricosanoate whole plant S. komarowii [27]
100 2-(4-hydroxypenyl)-ethyl lignocerate whole plant S. komarowii [27]
101 2-(4-hydroxyhenyl)-ethyl pentacosanoate whole plant S. komarowii [27]
102 2-(4-hydroxypenyl)-ethyl hexacosanoate whole plant S. komarowii [27]
103 Bongardol whole plant S. komarowii [27]
104 2-(4-hydroxypenyl)-ethyl 1-dodecyloctadecanoate whole plant S. komarowii [27]
105 2-(4-hydroxypenyl)-ethyl dotriacontanoate whole plant S. komarowii [27]
106 Coniferin barks S. vulgaris [29]
107
Coniferylaldehydel roots and stems S. pinnatifolia var. alashanensis [44]
108 Coniferyaldehyde glucoside barks S. reticulata [10]
109 Sinapaldehyde glucoside barks S. reticulata [10]
110 Syringin barks S. vulgaris, S. reticulata [10,45,46]
111 Isosyringinoside barks S. reticulata [10]
112 Eugenol foral buds S. patula [5]
113 Larixnaphthanoe roots and stems S. pinnatifolia var. alashanensis [30]
114 Cinnamic acid leaves, roots and stems S. afghanica, S. pinnatifolia
var. alashanensi, S. reticulata
[44,47]
115 Caffeic acid roots and stems S. pinnatifolia var. alashanensis [44]
116 Ferulic acid roots and stems S. pinnatifolia var. alashanensis [44]
117 7-Methoxycoumarin roots and stems S. pinnatifolia var. alashanensis [44]
118 Esculetine roots and stems S. pinnatifolia var. alashanensis [44]
119 Umbelliferone roots and stems S. pinnatifolia var.
alashanensis [44]
120 O-[β-D-xylopyanosy (16)
β-D-glucopyranosyl]-7-hydroxycoumarin
roots and stems S. pinnatifolia var. alashanensis [44]
121 Syringfghanoside leaves S. afghanica [13]
122 Astragalin bark S. vulgaris [48]
Su et al. Chemistry Central Journal (2015) 9:2 Page 8 of 12
could be used to develop effective and less toxic anti-
hepatitis B medicines [55].
Aqueous extracts of S. reticulata var. mandshurica sig-
nificantly decreased the levels of alanine transaminase and
aspartate transaminase and the concentration of malon-
dialdehyde in the serum but increased the activity of
superoxide dismutase (SOD) in the liver. These extracts
showed protective effects on acute liver injury induced by
CCl
4
in mice [56]. In addition, the essential oils of Syringa
exerted protective effects on the liver and cholecyst [39].
Antifungal activity
Phenylpropanoids such as verbascoside (86) and for-
sythiaside (82) exhibit significant antimicrobial activity
[29]. Compounds 93 and 94 at 1- mM concentration
inhibited the radial growth of Phytophthora capsici after
6 days of incubation, with inhibition rates 59.1% and
72.5%, respectively [43]. Two sesquiterpenes, guai-9-en-
4β-ol (129) and 4, 15-dinorguai-1, 11-dien-9, 10-dione
(130), have antibacterial and antifungal properties. Com-
pound 129 was active against Bacillus coagulans [inhib-
ition zone (IZ) = 15.34 mm] and Aspergillus niger (IZ =
13.20 mm) while compound 130 significantly inhibited
Escherichia coli (IZ = 15.34 mm) and Fusarium oxy-
sporum (IZ = 15.32 mm) [37].
Compound 3 showed effective antimicrobial activity
against Lactobacillus pentosus (IZ = 1 mm), and compound
139 inhibited the growth of Candida species at concentra-
tions of 30250 μg/mL [5].
Antioxidant activity
A 70% EtOH extract of S. reticulata barks showed po-
tent superoxide anion and DPPH free radical scavenging
activities, with EC
50
values of 5.88 and 38.10 μg/mL, re-
spectively [10].
Among the compounds isolated from the bark of S. reti-
culata,six(4, 31, 50, 77, 83,and111)showedsignificant
superoxide anion scavenging activity, with EC
50
values of
2.57, 4.97, 10.64, 15.98, 4.97, and 14.14 μg/mL, respectively.
Compound 4 also interacted with the stable free radical
DPPH, with an IC
50
value of 40.4 μM [8,10]. These different
anti-oxidant activities are closely related to their structural
features. Presence of 2-(3, 4-dihydroxyphenyl)-ethoxy moi-
ety might be important for a higher activity because the
most potent compounds (EC
50
=2.574.97 μM), including
the two secoiridoid glycosides (31 and 4) and a phenyletha-
noid glycoside (83), possess the same structural features.
Comparison of the structures of compounds 4 and 83 with
those of 8(Z)-ligstroside (21) and salidroside (89)showed
that presence of ortho-coupling hydroxyl group at C-2
might be responsible for their different activities. It has
been previously reported that 1, 2-dihydroxybenzene moi-
ety is crucial to its DPPH scavenging activity [10].
Table 3 Other type of compounds from the genus Syringa (Continued)
123 Kaempferol-3, 7-α-L-dirhamnoside flowers and leaves S. pubescens [3]
124 Kaempferol-3-β-D-glucoside-7-α-L-dirhamnoside flowers and leaves S. pubescens [3]
125 Kaempferol-3-O-rutinoside flowers S. vulgaris [49]
126 Luteolin leaves S. afghanica [13]
127 Rutin leaves S. vulgaris [49,50]
128 Rhoifolin leaves S. afghanica [13]
129 Guai-9-en-4β-ol roots and stems S. pinnatifolia var. alashanensis [37]
130 14, 15-dinorguai-1, 11-dien-9, 10-dione roots and stems S. pinnatifolia var. alashanensis [37]
131 Momorcerebroside I whole plant S. komarowii [27]
132 Phytolacca cerebroside whole plant S. komarowii [27]
133 Pubescenside A flowers and leaves S. pubescens [51]
134 Stigmastane-3β,6α-diol 3-O-tetradecanoate whole plant S. komarowii [27]
135 Stigmastane-3β,6α-diol 3-O
-palmitate whole plant S. komarowii [27]
136 Stigmastane-3β,6α-diol 3-O-stearate whole plant S. komarowii [27]
137 β-sitosterol foral buds and whole plant S. patula, S. komarowii [5,27]
138 Daucosterol whole plant S. komarowii [27]
139 β-Amyrin acetate foral buds S. patula [5]
140 Jasminidin leaves S. vulgaris [52]
141 Jasminin leaves S. vulgaris [52]
142 Nortropin foral buds S. patula [5]
Su et al. Chemistry Central Journal (2015) 9:2 Page 9 of 12
Syringaresinol (78) showed a strong scavenging activ-
ity against DPPH, with EC
50
value as low as 12.5 μg/ mL,
which might be responsible for its strong inhibition of
NO production [5].
Eugenol (112) inhibited the catalytic activity of H
2
O
2
/
Ca
2+
human erythrocyte membrane lipid peroxidation
at a concentration of 200 μmol/L, with an inhibition rate
of 62%, and completely suppressed the catalytic activity of
dibenzoyl peroxide/Ca
2+
human erythrocyte membrane
lipid peroxidation at a concentration of 100 μmol/L. Com-
pound 112 exerted its effect in a non-competitive manner
by reacting with Ca
2+
and inhibiting the formation of hy-
droxyl radicals, thus, protecting the cell membrane lipid
from oxidation [2].
Inhibition of platelet aggregation
Aqueous extract of S. aramaticum significantly inhibited
adenosine diphosphate (ADP) and collagen-induced
platelet aggregation, with inhibition rates of 37.4% and
69.7%, respectively [57]. Mandshuricols A (57)andB(58)
showed antagonistic activities on platelet-activating factor
(PAF) in [3H]PAF receptor binding assay, with IC
50
values
of 4.8 × 10
5
and 3.5 × 10
5
M, respectively [32].
Others
Essential oils from the stems and roots of S. pinn atifolia
var. alashanensis (SPEO) reduced the deviation of ST
segment; decreased the levels of lactate dehydrogenase,
creatine kinase, and troponin T; and increased the activity
of SOD. These protective effects were further confirmed
by histopathological examination [58]. Treatment with
both 8 and 32 mg/kg SPEO prolonged the survival of mice
under hypoxia conditions, showing a remarkable protect-
ive effect against H
2
O
2
-induced death in cultured rat myo-
cytes. Moreover, 5, 2.5 and 1.25 μg/mL doses of SPEO
inhibited ADP-induced rat platelet aggregation by 47.4%,
37.0%, and 32.9%, respectively [58], implying that SPEO
exerted protective effects against myocardial ischemia.
Oral and intra peritone al a dministration of 0.20.4 g
of leaf extract of S. vulgaris in cats or r abbits exerted an
antipyretic effe ct that was equal to the effe ct of 0.10.3
g of aminopyrine administered orally or intraperitone-
ally. H owe ver, leaf extract s of S. vulgaris are consider-
ably more toxic than aminopyrine, with t heir toxic
dosages being 0.4 and 1.2 g/kg, res pe ctively [59]. In vitro
evaluation of leaf extract of S. aramaticum sh owed it s
antiviral activity against herpes simplex virus at concen-
trations 1.25 %2.5%. The protective effect was more
obvious when controlling the amount of virus attacks at
9.292 tissue culture infective dose (TCID50), sugges t-
ing that S. aramaticum effectively killed the virus with-
out any harmful side eff e ct s [6 0-62].
Studies have reported that leaf extracts of S. aramati-
cum could be used for treating hemorrhoids [63].
Eugenol (112) inhibited the metabolism of arachidonic
acid. Extracts of S. reticulata var. mandshurica have
been used for treating bronchitis, and one of its constit-
uents 2-(3, 4-dihydroxyphenyl) ethanol (91) significantly
inhibited the production of phlegm [2].
Review and conclusions
This review describes phytochemical and pharmaco-
logical progress on the genus Syringa in the recent 20
years and discusses the future research prospects.
Syringa plants are used not only as traditional medicines
to treat rheumatoid arthritis, asthma, cardiopalmus, and
angina pectoris by natives in China but also for making or-
naments, volatile oils, food additives, and bactericides
worldwide, particularly in developing countries. Previous
phytochemical studies on crude extracts from various
species of this genus have identified iridoids, lignans, phe-
nylpropanoids, and phenylethanoids having antitumor, anti-
hypertensive, anti-oxidant, and anti-inflammatory activities.
Iridoids, lignans, and phenylethanoids are the most pre-
dominant compounds in Syringa plants that probably con-
tribute independently or synergistically to their main
biological activities.
To the best of our knowledge, 46 iridoid representa-
tives have been report ed in Syringa plants, with high
concentrations prese nt in the leaves of S. vulgaris, S.
pubescens , S. af ghanica , S. reticulata ,andS. velutina
and barks of S. vulgaris and S. reticulata and low con-
centrations p resent in the flowers (S. pubescens ), seeds,
and seeds crust (S. oblata). This difference may be asso-
ciated with their ecological roles, bec ause iridoids a re
produced mainly to fight predators and/or microbes.
Moreover, high concentrations of lignans in the stems
and root s can be attributed to the rigidity of these
plants. This may be the reason for the absence of iridoids
in S. pinnatifolia var. alashanensis because materials used
for chemical investigation included peeled stems and
roots. Anti-inflammatory effects of extracts from these
plants are mainly responsible for their applications in trad-
itional medicine. However, only preliminary work has
been performed on most isolated compounds, such as
in vitro cytotoxicity screening (1, 2, 78,and139). Limited
studies have been performed on the in vivo effects of these
compounds; thus, providing opportunities for further de-
tailed research. It is particularly worthy to mention that
China has an abundant resource of Syringa, with many en-
demic species. For instance, S. pinnatifolia var. alashanen-
sis is a well-known Mongolian medicine traditionally used
for myocardial ischemia in clinical practice. However, no
substantial evidence is available on its bioactive ingredi-
ents and mechanisms of action underlying this effect.
Therefore, it deserves further phytochemical and pharma-
cological studies.
Su et al. Chemistry Central Journal (2015) 9:2 Page 10 of 12
Competing interests
The authors declare that they have no competing interests.
Authors contributions
SG, CY, LC, GX, and YX have all been involved in preparing this review. SG, TP
and CX are responsible for writing, checking and revising the manuscript.
All authors read, discussed and approved final version of the manuscript.
Acknowledgments
This paper is financially supported by the National Natural Science
Foundation of China (No.81473426).
Author details
1
Modern Research Center for Traditional Chinese Medicine, Beijing University
of Chinese Medicine, 11 North 3rd Ring Road, Chaoyang District, Beijing
100029, P. R. China.
2
School of Chinese Materia Medica, Beijing University of
Chinese Medicine, 6 Wangjing Southern Middle Ring Road, Chaoyang
District, Beijing 100102, P. R. China.
Received: 26 April 2014 Accepted: 7 January 2015
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