全 文 :Co rr espondence to:Prof. Lu-Ping Q IN . E-mail:lpqin@smmu. edu. cn
一枝黄花属植物化学成分和药理活性研究
姜 涛 ,黄宝康 ,秦路平
(第二军医大学药学院生药学教研室 ,上海 200433)
[关键词] 一枝黄花属;化学成分;药理学
[中图分类号] R284. 1 [文献标识码] A [文章编号] 1672-1977(2006)04-0430-06
A survey of chemical and pharmacological studies on Solidago
Tao JIANG , Bao-Kang HUANG , Lu-Ping QIN
(1. Department of Pha rmacogno sy , Schoo l of Pharmacy , Second M ilita ry Medical Univ ersity , Shanghai 200433 , China)
KEYWORDS Solidago ;chemical principle;pharmacology
Zhong Xi Yi Jie He Xue Bao/J Chin Integr Med , 2006 , 4(4):430-435 www. jcimjournal. com
Herbal medicine has been used for treating differ-
ent diseases in China for thousands of years. The
genus Solidago L. , commonly known as golden-
rod , is one of the largest genera of the Asteraceae
family , with 120 species , most of them growing
wildly in North America. It is reported that Solida-
go plants have been shown to have good diuretic ,
choleretic , antiseptic and wound-healing activity.
All species are herbaceous perennials ranging from
5 cm to 3 m tall. These usually have small heads
with yellow pistillate ray and perfect disc florets
aggregated into flat-topped , wand-shaped or pyram-
idal inflorescences. The phyllaries are generally
lanceolate to ovate , present in 2-4 graduated
series , and have a translucent midrib.
There are four species of Solidago in China , in-
cluding Solidago decurrens , Solidago virgaurea ,
Solidago pacifica and Solidago canadensis . They
are widely distributed in Shanghai , Zhejiang ,
Jiangxi , Shaanxi and Taiwan provinces of China. In
addition , one vars. Solidago virgaurea L. var.
dahurica kitag is regarded as a traditional Chinese
medicine in Xinjiang province and Northeast China.
Solidago canadensis , a perennial plant originating
from North America , was introduced into China as a
horticultural plant in the 1970s. It has become an
invasive weed and caused damage to crops in dry
fields , impeded the recovery of vegetation in aban-
doned fields in recent years in China.
In order to understand and make good use of
Solidago plants , we surveyed the research docu-
ments about chemical principles and pharmacologi-
cal activities of these plants.
1 CHEMICAL PRINCIPLES
Many scholars found and isolated some chemical
principles from the plants of genus Solidago L. ,
such as flavonoids , leiocarposide , saponins , carote-
noids , sesquiterpenes and diterpenes. The struc-
tures of new compounds isolated from plants of
genus Solidago L. and the chemical principles of
genus Solidago L. are shown below (Table 1 and
Figure 1).
2 PHARMACOLOGICAL ACTIVITIES
2. 1 Diuretic activity
The aerial parts of Solidago virgaurea L. is used
as a diuretic. In the experiment , Guo[ 24] found the
quantity of urine was low with high dosage of the ex-
tracts from the aerial parts of Solidago virgaurea L. .
2. 2 Anti-inflammatory activity
Solidago virgaurea L. has been traditionally
used as an anti-inflammatory herbal medicine for
many years. Inflammatory model of ear edema was
induced by dimethyl benzene in mice. The extract
of Solidago virgaurea L. was tested on anti-
inflammation activity in mice. The result showed
that the ear edema induced by dimethyl benzene
could be obviously reduced when given 105 mg /kg
(i. g.) in mice[ 25] .
430 中西医结合学报 2006年 7月第 4卷第 4期 Journal of Chinese Integ rat ive Medicine , July 2006 , Vol. 4 , No. 4
Table 1 Chemical principles of genus Solidago L.(to be continued)
No. Chemical princip le Source Reference No.
1 Leiocarposide a , b 1-3
2 2-M ethoxybenzy-2 , 3 , 6-trim ethoxybenzoate a 2
3 Β-sitosterol a 2
4 3 , 5-Dimeth oxy-4-acetoxycinnam yl angelate a 2
5 3-M ethoxy-4-acetoxycinnamyl angelate a 2
6 2-M ethoxybenzyl-2 , 6-dimeth oxyb enzoate a 2
7 Benzy l-2-hyd roxy-6-methoxyb enzoate a 2
8 Meth yl(2E , 8Z)-decadien-4 , 6-diyn oate a 2
9 Benzy l-2 , 6-dimethoxybenzoate a 2
10 Meth yl(2Z , 8Z)-decadien-4 , 6-diynoate a 2
11 Caf feic acid a 4
12 Chlo rogenic acid a , h 4 , 21
13 A-pinene b , c , f , h 4 , 7 , 11 , 17
14 B-my rcene b , c , f , h 4 , 7 , 11 , 17
15* Virgaureasaponin 3 b 5
16 Quercetin-D-glucoside b 6
17 Kaempferol-D-glucoside b 6
18 Kaempferol-3-O-rut inoside b , g 6 , 20
19 Limonene b , c , j 7 , 11 , 22
20 B-elemene b , c 7 , 11
21 δ-elem ene b , c 7 , 11
22 Germacrene B b , c 7 , 11
23 Germacrene D b , c 7 , 11
24 δ-cadinene a , b 7 , 11
25 Oleanolic acid b 8
26 Bayogenin b 8
27* Virgaureoside A b 9
28* Solidagosaponins 21 b 10
29* Solidagosaponins 22 b 10
30* Solidagosaponins 23 b 10
31* Solidagosaponins 24 b 10
32* Solidagosaponins 25 b 10
33* Solidagosaponins 26 b 10
34* Solidagosaponins 27 b 10
35* Solidagosaponins 28 b 10
36* Solidagosaponins 29 b 10
37* Solidagosaponins 30 b 10
38* Canadensis saponin 1 c 12
39* Canadensis saponin 2 c 12
40* Canadensis saponin 3 c 12
41* Canadensis saponin 4 c 12
42 Bayogeninsaponin 1 c 13
43 Bayogeninsaponin 2 c 13
44 Bayogeninsaponin 3 c 13
45 Bayogeninsaponin 4 c 13
46 3-Epi-α-cubebene c 14
47 3-Epi-β-cubeben e c 14
48 3β-(3R-acetoxyh exadecan oyloxy)-lu p-20(29)-ene c 15
49 3β-(3-ketohexadecanoyloxy)-lu-20(29)-ene c 15
50 3β-(3R-acetoxyh exadecan oyloxy)-29-nor-luan-20-one c 15
51 3β-(3-hetohexadecanoyloxy)-29-nor-lu pan-20-one c 15
52* Elongatolide A d 16
53* Elongatolide B d 16
54* Elongatolide C d 16
55* Elongatolide D d 16
56* Elongatolide E d 16
57* T ran s-clerodane 5 e 17
431 中西医结合学报 2006年 7月第 4卷第 4期 J ou rnal of C hinese Integrative Medicine , Ju ly 2006 , Vol. 4 , No. 4
Table 1(continuation) Chemical principles of genus Solidago L.
No. Chemical princip le Source Reference No.
58* T ran s-clerodane 6 e 17
59* T ran s-clerodane 7 e 17
60 Erythrodiol-3-acetate g 18
61 α-t ocopherol-quinone g 18
62 T ran s-ph ytol . g 18 ,19
63 Ent-germacra-4(15), 5 , 10(14)-t rien-1α-ol g 19
64 B-amyrin acetate g 19
65 Meth yl-3 , 5-di-O-caf feoyl quinate g 19
66 Ent-germacra-4(15), 5 , 10(14)-t rien-1β-ol g 19
67 B-dicty op terol g 19
68 3 , 5-Di-O-caf feoyl quinic acid g 19
69 Kaempferol g 20
70 Epi-t ori len ol h 20
71 (5αH , 6βH , 7αH , 8βH , 10α-6 , 8-cycloeudesm-4(15)-en-1a-ol),
1 , 10-seco-eu desm a-4(15), 5(10)-dien-1-al
h 20
72 Cis-eu desm-4(10)-en-1-on e h 20
73 Quercetin-3-O-β-D-rutinoside(rutin) b 21
74 Isoschaf toside i 21
75* (+)-18-Tigloyxymannol k 23
76* 18-Hydroyabieta-7 , 13(14)-diene k 23
77* 18-Tigloyoxyabieta-7, 13(14)-diene k 23
78* 7-Hydroy-13 , 15-dihyd roxyabieta-8 (14)-ene-18-oic acid k 23
79* 15-H ydroydehyd roabietic acid k 23
*New compound;a:Sol id ago d ecur rens Lour. ;b:Sol id ago virga urea L. ;c:Sol id ago canadensis;d:So lidago elongate Nut t . ;
e:Sol idago arguta ;f:Sol id ago odora Ait. ;g:So lidag o virga-aurea var g ig antean;h:Solida go gig antea Ait. ;i:Sol idago g ramini fol ia ;
j:Solid ago chi lensis;k:Solid ago ru gosa .
Figure 1(A) Structures of new compounds isolated from plants of genus Solidago L.
432 中西医结合学报 2006年 7月第 4卷第 4期 Journal of Chinese Integ rat ive Medicine , July 2006 , Vol. 4 , No. 4
Figure 1(B) Structures of new compounds isolated from plants of genus Solidago L.
433 中西医结合学报 2006年 7月第 4卷第 4期 J ou rnal of C hinese Integrative Medicine , Ju ly 2006 , Vol. 4 , No. 4
2. 3 Antifungal activity
Essential oils and ethanol extracts from the leaves
and roots of 35 medicinal plants commonly used in
Brazil were screened for anti-Candida albicans ac-
tivity. The oils were obtained by water-distillation
using a Clevenger-type system. Essential oils from
13 plants showed anti-Candida activity , including
Solidago chilensis
[ 26] .
Roser et al [ 27] identified and analyzed thirty-six
different compounds of the essential oils from leaves
and inflorescences of Solidago chilensis Meyen by
GC-FID (gas chromatography and flame-ionization-
detector), GC-MS (gas chromatography and mass
spectrum) and 13C-NMR(13C and nuclear magnetic
resonance spectroscopy). In addition , the antifun-
gal activity of the leaf oil was assayed against five
different strains of filamentous fungi and one yeast.
The result showed that the human pathogenic
dermatophyte was the most sensitive.
2. 4 Anticancer activity
Gross et al [ 28] found that the extract of S .
virgaurea exhibits strong cytotoxic activities on
various tumor cell lines. The active component
mostly resides in the leaves of the plant and is solu-
ble in water. When the extract was fractionated by
a Sephadex G-100 column , the active fraction corre-
sponded to a molecular weight of approximately
40 000. This cytotoxic activity is effective on vari-
ous tumor cell lines , including human prostate car-
cinoma , breast carcinoma , melanoma , and small
cell lung carcinoma. To examine the effect of the
cytotoxic activity on tumor cells in vivo , the rat
prostate carcinoma cell line (AT 6. 1) and an SCID
(severe combined immunodeficiency)mouse model.
AT6. 1 cells were injected into the flank of SCID
mice , and then the G-100 fraction of S . virgaurea
was injected intraperitoneally or subcutaneously ev-
ery 3 days. The size of the tumor was measured for
up to 25 days. The growth of the tumor was signifi-
cantly suppressed by the G-100 fraction at 5 mg /kg
without any apparent side effects. Therefore , S .
virgaurea is considered to be promising as an
antineoplastic medicine with minimal toxicities.
2. 5 Antioxidant activity
Thirty-five plant species were selected from the
published literature as traditionally used by the in-
digenous peoples of the boreal forest in Canada for
three or more symptoms of diabetes or its complica-
tions. Antioxidant activities in methanol extracts
support the contribution of these traditional medi-
cines in a lifestyle historically low in the incidence
of diabetes. It is reported that antioxidant activity
of Solidago canadensis extract was greater than
green tea , ascorbic acid and Trolox[ 29] .
3 PERSPECTIVE
The genus Solidago L. comprises a large group
of medicinal plants with recognized therapeutic ap-
plications , especially S . virgaurea , S . gigantea
and S . canadensis , the aerial parts of which are
used in folk medicine in many countries.
Furthermore , S . canadensis has caused serious
harm to crop production , orchards , lawns , natural
environments and biodiversity in China[ 30] . Studies
on the physical and ecological characteristics of
newly introduced exotic weeds are of practical
significance in the predication of their potential
distribution areas and their habitats. It is urgent for
us to make good use of this plant.
Although great progress has been made over the
past decades in study of chemical active components
and pharmacological activities of genus Solidago ,
the results are still unsatisfactory. It is necessary
for us to make good use of Solidago plants and find
out which plant shows high activity and low
toxicity.
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Received 2005-11-02
中国康复医学会颈椎病专业委员会第九次学术年会征文通知
为了加深对颈椎病的认识 ,提高诊治康复水平 , 展现现代康复技术 , 由中国康复医学会主办 ,中国康复医学会颈椎病专业
委员会 、第二军医大学附属长海医院 、上海中医药大学脊柱病研究所 、上海中医药大学附属龙华医院承办的“中国康复医学会
颈椎病专业委员会第九次学术年会”拟定于 2006 年 10 月在上海召开。会议现在征文 , 现将具体征文事宜通知如下。
1 征文内容 (1)颈椎病 、腰椎间盘突出症 、腰椎管狭窄症康复研究进展;(2)关于颈椎病 、腰椎间盘突出症 、腰椎管狭窄
症的“围手术期”治疗;(3)颈椎病 、腰椎间盘突出症 、腰椎管狭窄症基础与应用研究进展;(4)颈椎病 、腰椎间盘突出症 、腰椎管
狭窄症手术治疗进展;(5)颈椎病 、腰椎间盘突出症 、腰椎管狭窄症的非手术(中药 、针灸 、推拿 、导引等)治疗进展;(6)脊柱相关
疾病研究进展(椎体骨质疏松 、椎体不稳 、骨质疏松性骨折 、脊柱肿瘤等)。
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435 中西医结合学报 2006年 7月第 4卷第 4期 J ou rnal of C hinese Integrative Medicine , Ju ly 2006 , Vol. 4 , No. 4