全 文 :中草药 Chinese Traditional and Herbal Drugs 第 46 卷 第 2 期 2015 年 1 月
·280·
·综 述·
石头花属植物的化学成分及药理作用研究进展
解龙霄,孙得峰,汪海洋,姚庆强,孙敬勇*
山东省医学科学院药物研究所,济南大学 山东省医学科学院医学与生命科学学院,山东省罕少见病重点实验室,山东
济南 250062
摘 要:石头花属植物主要化学成分为黄酮类、环肽类、甾醇类、挥发油、三萜及其皂苷等化合物,具有抗肿瘤、抗肥胖、
抗糖尿病、保肝、抗氧化等药理作用。在检索国内外相关文献的基础上,对石头花属的植物资源、化学成分及药理作用进行
综述,以期为石头花属植物进一步研究和开发利用提供参考。
关键词:石头花属;植物资源;黄酮类;抗肿瘤;抗氧化
中图分类号:R282.71 文献标志码:A 文章编号:0253 - 2670(2015)02 - 0280 - 13
DOI: 10.7501/j.issn.0253-2670.2015.02.024
Research progress on chemical constituents in plants of Gypsophila L. and their
pharmacological activities
XIE Long-xiao, SUN De-feng, WANG Hai-yang, YAO Qing-qiang, SUN Jing-yong
Key Laboratory of Rare and Uncommon Diseases of Shandong Province, Shandong Academy of Medical Sciences, School of Medicine
and Life Sciences, University of Jinan, Institute of Materia Medica, Shandong Academy of Medical Sciences, Jinan 250062, China
Abstract: The plants in Gypsophila L. mainly contain chemical constituents, such as flavonoids, cyclic peptides, sterols, volatile oil,
triterpenoid saponins, and other compounds which possess antitumor, anti-obesity, anti-diabetic activity, hepatoprotective activity,
anti-oxidation, and so on. On the basis of the retrieval of relevant literature, this paper summarizes the progress on resources, chemical
composition, pharmacological action, and clinical application of the plants in Gypsophila L., and provides the references for the further
study and development of the plants in Gypsophila L.
Key words: Gypsophila L.; plant resources; flavonoids; antitumor; anti-oxidation
石头花属 Gypsophila L. 为石竹目石竹科植物,
约 150 种,分布于亚洲、欧洲及南美洲。我国有 18
种 1 变种[1]。石头花属植物可供药用,也可供观赏。
其具有清热凉血、活血化瘀、消肿止痛、化腐生肌
等功效,可治虚劳骨蒸、阴虚久疾、小儿疳热等[2-3]。
现代研究表明,该属主要药用种类有长蕊石头花(又
名霞草、丝石竹)、大叶石头花、头状石头花等,其
中药用成分主要为皂苷类。其皂苷类成分也被证实
在抗肿瘤、免疫调节等方面有显著的活性。本文着
重阐述石头花属的植物资源、主要化学成分、药理
作用 3 个方面的研究进展。
1 中国石头花属植物的分类
我国石头花属植物大多分布于西北、华北和东
北地区,新疆是其分布和分化集中地,种数往东递
减。河北石头花、华山石头花、刺序石头花和细叶
石头花为我国特有种[4]。目前研究发现长蕊石头花、
草原石头花、大叶石头花等可供药用。按多年生或
一年生、茎直立或斜升、植株高矮、苞片干膜质或
叶状、花萼有无白色间隔及宽狭、花序形状、密集
或疏散、有无刺、花梗粗细等将中国石头花属种分
为 5 组[4]。其种类及植物资源分布见表 1[4-5]。
2 化学成分
2.1 黄酮类化合物
黄酮类化合物是许多中药中的有效成分,具有
保肝、降血压、抗菌、抗心律失常等作用。此外,
其还具有抗自由基、抑制肿瘤细胞和抗致癌促进因
子作用,可以防止机体的脂质过氧化反应[6]。目前
从石头花属植物中共发现 10 个黄酮类化合物,具有
收稿日期:2014-06-13
基金项目:山东省科技发展计划项目(2013GSF11854)
作者简介:解龙霄(1989—),女,在读研究生,研究方向为天然药物化学。Tel: 15865317502 E-mail: xielongxiao_qq@126.com
*通信作者 孙敬勇 Tel: (0531)82919963 E-mail: sunjingyong08@hotmail.com
中草药 Chinese Traditional and Herbal Drugs 第 46 卷 第 2 期 2015 年 1 月
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表 1 中国石头花属种类及植物资源分布
Table 1 Species in Gypsophila L. and their resource distribution in China
组名 种名 种数 产地
高石头花 G. altissima L. 新疆(霍城、伊宁、察布查尔、昭苏、新源)
膜苞石头花 G. cephalotes (Schrenk)
F. N. Williams
新疆阿尔泰山、天山地区、塔什库尔干
长蕊石头花 G. oldhamiana Miq. 辽宁、河北、山西、陕西、山东、江苏、河南
河北石头花 G. tschiliensis J. Krause 河北小五台山、涞源县白石山、北京百花山
华山石头花 G. huashanensis Y. W. Tsui.
& D. Q. Lu
陕西华山、秦岭地区
草原石头花(原变种)G. davurica Turcz.
ex Fenzl var. davurica
东北、内蒙古、河北(围场)
狭叶草原石头花(变种)G. davurica
var. angustifolia Fenzl in Ledeb.
内蒙古东部
大叶石头花 G. pacifica Kom. 东北
紫萼石头花 G. patrinii Ser. 宁夏、甘肃、青海、新疆
头状石头花 G. capituliflora Rupr. 蒙古、宁夏、甘肃、新疆
细叶石头花 G. licentiana Hand. -Mazz. 河北、山西、内蒙古、陕西(北部)、宁夏、
甘肃、青海、新疆
伞房花序组 Sect. Corym-
bosae Barkoudah
刺序石头花 G. spinosa D. Q. Lu
11 种、
1 变种
新疆阿尔泰山、额尔齐斯河地区(吉木乃、
布尔津、阿勒泰、北屯)
圆锥石头花 G. paniculata L. 新疆阿尔泰山、塔什库尔干 圆锥花序组 Sect. Rokeje-
ka (Forssk.) A. Br. 钝叶石头花 G. perfoliata L.
2 种
新疆北部
卷耳状石头花 G. cerastioides D. Don 西藏喜马拉雅山、横断山区(吉隆、亚东、
错那、察隅、察瓦龙)
荒漠石头花 G. desertorum (Bge.) Fenzl 内蒙古
异色组 Sect. Heterochroa
(Bge.) Fenzl
绢毛石头花 G. sericea (Ser.) Krylov
3 种
新疆阿尔泰山区(清河、福海)
缕丝花组 Sect. Dichoglottis
(Fisch. et Mey.) Fenzl
缕丝花 G. elegans M. Bieb. 1 种 北京、上海、杭州、庐山、呼和浩特、兰州、
重庆、新疆等
长胚根组 Sect. Macrorrhi-
zaea Boiss.
细小石头花 G. muralis L. 1 种 黑龙江兴凯湖东岸
黄酮(I)和双苯吡酮(II)2 种母核(图 1),化合
物名称及取代基见表 2。
OR1O
OH O
O
H
R3
O
OR2
HO
HO
OH OR1O
R2
OH O
OH
OH
I II
图 1 石头花属植物的黄酮类成分母核
Fig. 1 Parent nuclei of flavonoids from plants in Gypsophila L.
2.2 环肽类化合物
目前,该属植物中的环肽类化合物结构式、名
称和植物来源见图 2 和表 3。
2.3 甾醇类成分
目前,从该属中分离得到了 2 种母核的甾醇类化
合物(图 3)。化合物名称、取代基和植物来源见表 4。
2.4 挥发性成分
采用顶空固体微萃取法、索氏提取法及水蒸气
蒸馏法从长蕊石头花中提取挥发性成分,并用
GC-MS 联用技术确定了 131 种成分,主要为苯及苯
的同系物、醇醚类、烷烃类、烯类、酯类、茚类、
芴类及杂环类。主要化合物有 3-methyl-butanal
(26)、squalene(27)、1,2-benzenedicarboxylic acid
diisooctyl ester ( 28 )、 naphazoline ( 29 )、 2-
methyl-naphthalene(30)、4-methyl-1-pentanol(31)、
anethole(32)、benzeneacetaldehyde(33)、methyl
hexadecanoate ( 34 )、 naphazoline ( 35 )、 2, 3-
dihydro-4-methyl-1H-indene(36)、phenmetrazine(37)
等[19-22]。
中草药 Chinese Traditional and Herbal Drugs 第 46 卷 第 2 期 2015 年 1 月
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表 2 石头花属植物的黄酮类成分
Table 2 Flavonoids from plants in Gypsophila L.
编号 化合物名称 母核 取代基 植物来源 参考文献
1 isoscoparin I R1=R2=H, R3=CH3O b 7
2 isovitexin I R1=R2=R3=H a、e 8-9
3 2″-O-rhamnopyransoyl-isovitexin I R1=R3=H, R2=Rha e 9
4 isoorientin I R1=R2=H, R3=OH e 9
5 2″-O-rhamnopyransoyl-7- methoxylisoorientin I R1=CH3O, R2=Rha, R3=OH e 9
6 2″-O-rhamnopyransoyl-isoorientin I R1=H, R2=Rha, R3=OH e 9
7 apigenin 6-C-[α-L-arabinosyl-(1″→2″)-β-D-gluco-
pyranosyl]-7-O-β-D-glucopyranoside
I R1=Glc, R2=Ara, R3=H a 10
8 isoorientin-2″-O-α-L-arabinopyranosyl I R1=H, R2=Ara, R3=OH c 11
9 luteolin 7-O-α-L-arabinopyranosyl-6-C-β-glucopyranoside I R1=Ara, R2=H, R3=OH d 12
10 mangiferin II R1=H, R2=Glc e 9
a-G. oldhamiana b-G. capituliflora c-G. elegans d-G. repens e-G. pacifica
O O
OO
O O
N
NH
N
NH
NH
O
NH
NH
H
H
H
H
H
O
11
N
NH
NH
NH
NH
NH
NH
NH
O
O
O
O
OH O
O
O
NH2
O
O
12
N
NH
N
NH
NH
O
O
O
ONH
O
N
O O
N
O
O
NH OH
O
NH
OH
NH
NH
NH
NH
NH
NH
N
NH
OOH
O
O
O
O
O
OH
O
O
NH
NH
NH
NH
NH
NH
NH
N
O
O
O
OH
O
OH
O
O
O
O
OH
NH
NH
NH
N
NH
N
O
O
O
O
O
O
NH
O
13 14
15 16
NH
NH
NH
NH
N
NH
O
O
O
O
O
O
NH
O
OOH
17
HN
N
H
O
N
O
N
O
O
HN
HN O
H
O
NH
H
H
HN
N
H
O
N
O
N
OH
NH
O
NH
O
O
H
H
HN
O
NH
O
N
O
N
O
NH
H
N
O
H
N
O
N
O
H
H H
H
H
HN
O
N
H
HO
O
N
H
OH
O
NH
NH
N
N
HO
O
OO
HN
H
H
H
H
18
19 20 21
OH
OH
OH
图 2 石头花属植物的环肽类成分结构
Fig. 2 Chemical structures of cyclic peptides from plants in Gypsophila L.
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表 3 石头花属植物的环肽类化合物
Table 3 Cyclic peptides from plants in Gypsophila L.
编号 化合物名称 分子式 植物来源 参考文献
11 cyclo-(Gly1-Phe2-Asp3-Phe4-Ile5-Leu6-Pro7) C41H53N7O8 a 13
12 cyclo-(Pro1-Tyr2-Ser3-Phe4-Phe5-Val6-Ile7-Gln8) C51H67N9O11 a 14
13 cyclo-(Pro1-Phe2-Pro3-Pro4-Ser5-Thr6-Gly7-Leu8-Pro9-Ile10) C50H74N10O12 a 14
14 cyclo-(Pro1-Gly2-Ile3-Phe4-Thr5-Ile6-Ile7-Thr8) C42H66N8O10 a 14
15 cyclo-(Pro1-Gly2-Leu3-Ser4-Thr5-Ile6-Leu7-Thr8) C36H62N8O11 a 14
16 cyclo-(Pro1-Gly2-Leu3-Val4-Pro5-Ile6-Gly7) C31H51N7O7 a 14
17 cyclo-(Pro1-Gly2-Phe3-Asp4-Phe5-Ile6-Leu7) C41H55N7O9 a 14
18 cyclo-(Leu1-Pro2-Leu3-Trp4-Pro5-Gly6) C35H49N7O6 f 15
19 cyclo-(Leu1-Pro2-Tyr3-Phe4-Pro5-Gly6) C36H46N6O7 f 15
20 cyclo-(Ala1-Pro2-Tyr3-Leu4-Leu5-Pro6-Pro7-Ala8) C42H62N8O9 f 15
21 cyclo-(Leu1-Trp2-Pro3-Gly4-Gly5-Ser6-Ser7) C32H44N8O9 f 15
f-G. arabica
III IV
R1O R1O
图 3 石头花属植物的甾醇类成分母核
Fig. 3 Parent nuclei of sterols from plants in Gypsophila L.
2.5 三萜及其皂苷类
三萜及其皂苷类成分不仅是该属植物的主要化
学成分,也是具有生物活性的有效成分。该属植物
中的三萜类成分几乎都是五环三萜。石头花属中主
要的三萜皂苷类化合物见图 4 和表 5。
2.6 其他
石头花属中还含有其他化合物,如 tetracosyl
caffeate[7](138)、alternariol[7](139)、alternariol
monomethylether[7](140)、syringaldehyde[8](141)、
表 4 石头花属植物的甾醇类成分
Table 4 Sterols from plants in Gypsophila L.
编号 化合物名称 母核 取代基 植物来源 参考文献
22 β-D-glucoside-α-spinasterol III R1=Glc a 16-18
23 α-spinasterol III R1=H a 17-18
24 β-sitosterol IV R1=H a、b 7-8,16-18
25 daucosterol IV R1=Glc a、b 7-8,16-18
arbutin[8](142)、octadecyl caffeate[16-18](143)、ferulic
acid[17-18](144)、p-hydroxycinnamic acid[48](145)、
dihydroferulic acid[48](146)、syringic acid[48](147)、
vanillic acid[48](148)等。上述部分化合物的结构
式见图 5。
3 药理作用
3.1 抗肿瘤作用
采用 MTT 法及 8 种人源肿瘤细胞株(KB、
PC-3M、A549、KeTr3、A2780、SMMC-7721、HT29、
SGC7901)对霞草(长蕊石头花)中霞草皂苷(43)
进行细胞毒活性评价,发现其具有一定的体外抑瘤
作用,IC50 小于 50 μg/mL[18,37,49-51]。研究还表明,ip
7.5、10.0 mg/kg 霞草皂苷(43)对小鼠 S180 肉瘤和
H22 肝癌具有明显的抑制作用,抑瘤率分别为
32.8%、51.1%和 42.3%、45.8%,与对照组比较均
具有统计学意义,虽然抑瘤率不及阳性对照组,但
不良反应较轻[49]。
Arslan 等 [31]发现石头花属植物 G. pilulifera
Boiss. & Heldr. 中化合物 44 对 A549 细胞具有明显
的选择抑制活性(IC50>16 μmol/L)。
中草药 Chinese Traditional and Herbal Drugs 第 46 卷 第 2 期 2015 年 1 月
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R4
R3
R1O
COOR2
R3
OSO3H
COOR1
O
COOR1
R2
CH2OH
CHO
R1O
O
XXV R3=OH R4=CHOVI R3=H R4=CHO
VII R3=H R4=COOH
VIII R3=H R4=OH
IX R3=OH R4=OH
X R3=OH R4=CH2OH
XI R3=H R4=CH2OH
XII R3=H R4=CH2OSO3
R2
XIII R2=H R3=CHO
XIV R2=OH R3=CHO
XV R2=H R3=CH3
XVI R2=OH R3=CH3
XVII R2=H R3=CH2OH
XVIII R2=OH
XIX R2=H
135
OSO3H
COOR
COOH
136 R=H
137 R=Glc
H
HO
H
H
OO
OH
HO
HO
O
O
O
OH
O
O
O
OH
HO
O
HO
HOHO
OH
HO
HO
HOHO
图 4 石头花属植物的三萜类成分母核及部分结构
Fig. 4 Parent nuclei and some structures of triterpenoids from plants in Gypsophila L.
表 5 石头花属植物的三萜类成分
Table 5 Triterpenoids from plants in Gypsophila L.
编号 化合物名称 母核 植物来源 参考文献
38 quillaic acid α-L-arabinopyranosyl-(1→4)-α-L-arabinopyranosyl-(1→3)-β-D-
xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranosyl ester
V a 23
39 3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopy-
ranosyl quillaic acid methyl ester
V a 24
40 3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosy1-(1→3)]-β-D-glucuronop-
yranosyl quillaic acid 28-{O-β-D-fucopyranosyl-(1→4)-[β-D-glucopyranosyl-
(1→3)]-α-L-rhamnopyranosyl} ester
V a 24
41 quillaic acid 3-O-β-D-galactopyranosyl-(1→2)-[β-D-galactopyranosyl-(1→3)]-β-
D-glucuronopyranoside
V a 25
42 quillaic acid V a 26-28
43 3-O-{β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopy-
ranosyl}quillaic acid 28-[α-L-arabinopyranosyl-(1→2)-α-L-arabinopyranosyl-(1→3)-
β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranosyl] ester
V a 29-30
44 3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopy-
ranosyl quillaic acid 28-O-β-D-glucopyranosyl-(1→3)-[β-D-xylopyranosyl-
(1→4)]-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranosyl ester
V g 31
45 3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopyrano-
syl quillaic acid 28-O-β-D-glucopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→4)]-α-L-
rhamnopyranosyl-(1→2)-[α-L-arabinopyranosyl-(1→4)]-β-D-fucopyranosyl ester
V e 32
中草药 Chinese Traditional and Herbal Drugs 第 46 卷 第 2 期 2015 年 1 月
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续表 5
编号 化合物名称 母核 植物来源 参考文献
46 3-O-β-D-galactopyranosyl-(1→2)-[α-L-arabinopyranosyl-(1→3)]-β-D-glucopyrano-
syl quillaic acid 28-O-a-L-arabinopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-[β-
D-glucopyranosyl-(1→3)]-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-
(1→4)]-β-D-fucopyranosyl ester
V e 32
47 3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopyrano-
syl quillaic acid 28-O-β-D-xylopyranosyl-(1→3)-β-D-xylopyranosyl-(1→3)-β-D-
xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-[3, 4-di-O-acetyl-β-D-
quinovopyranosyl-(1→4)]-β-D-fucopyranoside
V k 33
48 3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopyrano-
syl quillaic acid 28-O-β-D-xylopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→3)]-α-L-
rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-fucopyranosyl ester
V l 34
49 3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopyrano-
syl quillaic acid 28-O-β-D-glucopyranosyl-(1→3)-[β-D-xylopyranosyl-(1→3)-β-D-
xylopyranosyl-(1→4)]-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranosyl ester
V l 35
50 3-O-α-L-arabinopyranosyl-(1→2)-[β-D-galactopyranosyl-(1→3)]-β-D-glucuronopy-
ranosyl quillaic acid 28-O-α-L-arabinopyranosyl-(1→4)-α-L-arabinopyranosyl-(1→3)-
β-D-xylopyranosyl-(1→3)-β-D-xylopyranosyl-(1→2)-3-O-acetyl-4-O-cis-p-
methoxycinnamoyl-β-D-fucopyranoside
V n 36
51 3-O-α-L-arabinopyranosyl-(1→2)-[β-D-galactopyranosyl-(1→3)]-β-D-glucuronopyrano-
syl quillaic acid 28-O-β-D-xylopyranosyl-(1→3)-β-D-xylopyranosyl-(1→3)-β-D-
xylopyranosyl-(1→2)-3-O-acetyl-4-O-trans-p-methoxycinnamoyl-β-D-fucopyranoside
V n 36
52 3-{{O-β-D-xylopyranosyl-(1→4)-β-D-galactopyranosyl-(1→2)-O-[α-L-arabinopyrano-
syl-(1→3)]-β-D-glucopyranuronosyl}oxy}quillaic acid 28-{O-β-D-xylopyranosyl-
(1→3)-O-β-D-xylopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2)-O-β-D-
quinovopyranosyl-(1→4)]-β-D-fucopyranosyl} ester
V n 37
53 3-{{O-α-L-arabinopyranosyl-(1→3)-O-[β-D-galactopyranosyl-(1→2)]-β-D-glucopy-
ranuronosyl}oxy}quillaic acid 28-{O-β-D-galactopyranosyl-(1→3)-O-β-D-
xylopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranosyl} ester
V n 37
54 3-{{O-β-D-galactopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-β-D-glucopy-
ranosyl}oxy}quillaic acid methyl ester
V n 37
55 3-{{O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-β-D-glucopy-
ranuronosyl}oxy}quillaic acid
V n 37
56 3-{{O-β-D-galactopyranosyl-(1→4)-O-[β-D-glucopyranosyl-(1→2)]-β-D-glucopy-
ranuronosyl}oxy}quillaic acid
V n 37
57 3-{O-β-D-galactopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopy-
ranosyl} quillaic acid 28-{O-β-D-xylopyranosyl-(1→3)-O-β-D-xylopyranosyl-
(1→4)-O-α-L-rhamnopyranosyl-(1→2)-O-[3,4-di-O-acetyl-β-D-quinovopyrano-
syl-(1→4)]-β-D-fucopyranosyl} ester
V n 38
58 rubicunoside C V n 38
59/60 3-O-[β-D-galactopyranosyl-(1→2)][β-D-xylopyranosyl-(1→3)]-β-D-glucuronopyrano-
syl quillaic acid 28-O-[α-L-rhamnopyranosyl-(1→2)]-4-O-acetyl-3-O-(E/Z)-para-
methoxycinnamoyl-β-D-fucopyranosyl ester
V n 38
61 quillaic acid 3-O-β-D-xylopyranosyl-(1→3)-β-D-glucuronopyranoside V o 39
62 3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopy-
ranosyl quillaic acid 28-O-(6-O-acetyl)-β-D-glucopyranosyl-(1→3)-[β-D-xylopy-
ranosyl-(1→4)]-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranoside
V o 39
中草药 Chinese Traditional and Herbal Drugs 第 46 卷 第 2 期 2015 年 1 月
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编号 化合物名称 母核 植物来源 参考文献
63 3-O-β-D-galactopyranosyl-(1→2)-6-O-methyl-β-D-glucuronopyranosyl quillaic acid V o 39
64 3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopy-
ranosyl gypsogenin methyl ester
VI a 24
65 gypsogenin 28-O-α-D-galactopyranosyl-(1→6)-β-D-glucopyranosyl-(1→6)-[β-D-
glucopyranosyl-(1→3)]-β-D-glucopyranosyl ester
VI a 25
66 3-O-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-
xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranoside
VI a 25
67 3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopy-
ranosyl gypsogenin 28-O-α-L-arabinopyranosyl-(1→3)-β-D-xylopyranosyl-
(1→4)-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranoside
VI a 25
68 3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopyrano-
syl gypsogenin 28-O-(6-O-acetyl)-β-D-glucopyraanosyl-(1→3)-[β-D-xylopy-
ranosyl-(1→4)]-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranoside
VI a 25
69 3α-hydroxyepigypsogenin VI a 18,28
70 gypsogenin VI a 18,27-28
71 3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-methyl-β-D-glucurono-
pyranosyl gypsogenin 28-O-β-D-glucopyranosyl-(1→3)-[β-D-xylopyranosyl-
(1→4)]-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranoside
VI a 30
72 3-O-β-D-xylopyranosyl-(1→3)-[β-D-galactopyranosyl-(1→2)]-β-D-glucuronopy-
ranosyl gypsogenin
VI a 40
73 3-O-(α-L-arabinopyranosyl-(1→3)-[β-D-galactopyranosyl-(1→2)]-β-D-glucurono-
pyranosyl)-28-O-(3-O-sulphate-β-D-glucopyranosyl-(1→3)-[β-D-xylopyranosyl-
(1→4)]-α-L-rhamnopyranosyl-(1→2)-4-O-acetyl-β-D-fucopyranosyl)-gypsogenin
VI h 41
74 3-O-(β-D-xylopyranosyl-(1→3)-[β-D-galactopyranosyl-(1→2)]-β-D-glucuronopy-
ranosyl)-28-O-(3-O-sulphate-β-D-glucopyranosyl-(1→3)-[β-D-xylopyranosyl-
(1→4)]-α-L-rhamnopyranosyl-(1→2)-4-O-acetyl-β-D-fucopyranosyl)-gypsogenin
VI h 41
75 3-O-(α-L-arabinopyranosyl-(1→3)-[β-D-galactopyranoyl-(1→2)]-β-D-glucuronopy-
ranosyl)-28-O-(3-O-sulphate-β-D-glucopyranosyl-(1→3)-[β-D-xylopyranosyl-(1→
4)]-α-L-rhamnopyranosyl-(1→2)-3-O-acetyl-β-D-fucopyranosyl)-gypsogenin
VI h 41
76 3-O-(α-L-arabinopyranosyl-(1→3)-[β-D-galactopyranoyl-(1→2)]-β-D-glucuronopy-
ranosyl)-28-O-(β-D-glucopyranosyl-(1→3)-[β-D-xylopyranosyl-(1→4)]-α-L-
rhamnopyranosyl-(1→2)-4-O-acetyl-β-D-fucopyranosyl)-gypsogenin
VI h 41
77 3-O-(α-L-arabinopyranosyl-(1→3)-[β-D-galactopyranoyl-(1→2)]-β-D-glucuronopy-
ranosyl)-28-O-(6-O-acetyl-β-D-glucopyranosyl-(1→3)-[β-D-xylopyranosyl-(1→4)]-
α-L-rhamnopyranosyl-(1→2)-4-O-acetyl-β-D-fucopyranosyl)-gypsogenin
VI h 41
78 3-O-(β-D-xylopyranosyl-(1→3)-[β-D-galactopyranosyl-(1→2)]-β-D-glucuronopy-
ranosyl)-28-O-(6-O-acetyl-β-D-glucopyranosyl-(1→3)-[β-D-xylopyranosyl-(1→4)]-
α-L-rhamnopyranosyl-(1→2)-4-O-acetyl-β-D-fucopyranosyl)-gypsogenin
VI h 41
79 3-O-(α-L-arabinopyranosyl-(1→3)-[β-D-galactopyranoyl-(1→2)]-β-D-glucuronopy-
ranosyl)-28-O-(β-D-glucopyranosyl-(1→3)-[β-D-xylopyranosyl-(1→4)]-α-L-
rhamnopyranosyl-(1→2)-β-D-fucopyranosyl)-gypsogenin
VI h 41
中草药 Chinese Traditional and Herbal Drugs 第 46 卷 第 2 期 2015 年 1 月
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续表 5
编号 化合物名称 母核 植物来源 参考文献
80 3-O-(α-L-arabinopyranosyl-(1→3)-[β-D-galactopyranosl-(1→2)]-β-D-glucuronopy-
ranosyl)-28-O-(6-O-acetyl-β-D-glucopyranosyl-(1→3)-[α-L-arabinopyranosyl-
(1→3)-β-D-xylopyranosyl-(1→4)]-α-L-rhamnopyranosyl-(1→2)-4-O-acetyl-
β-D-fucopyranosyl)-gypsogenin
VI h 41
81 3-O-(β-D-xylopyranosyl-(1→3)-[β-D-galactopyranosyl-(1→2)]-β-D-glucuronopy-
ranosyl)-28-O-(6-O-acetyl-β-D-glucopyranosyl-(1→3)-[α-L-arabinopyranosyl-(1→
3)-β-D-xylopyranosyl-(1→4)]-α-L-rhamnopyranosyl-(1→2)-4-O-acetyl-β-D-
fucopyranosyl)-gypsogenin
VI h 41
82/83 3-O-(α-L-arabinopyranosyl-(1→3)-[β-D-galactopyranosyl-(1→2)]-β-D-glucuronopy-
ranosyl)-28-O-(β-D-glucopyranosyl-(1→3)-[α-L-arabinopyranosyl-(1→3)-β-D-
xylopyranosyl-(1→4)]-α-L-rhamnopyranosyl-(1→2)-4-O-cis/trans-methoxy-
cinnamoyl-β-D-fucopyranosyl)-gypsogenin
VI h 41
84 3-O-β-arabinopyranosyl-(1→3)-[β-galactopyranosyl-(1→2)]-β-glucuronopyranosyl
gypsogenin
VI h 26
85 3-O-β-xylopyranosyl-(1→3)-[β-galactopyranosyl-(1→2)]-β-glucuronopyranosyl
gypsogenin
VI h 26
86 3β-hydroxyolean-12-en-23-oxo-28-oic acid 28-O-[β-D-glucopyranosyl-(1→2)-β-
D-galactopyranosyl-(1→3)]-[β-D-glucopyranosyl-(1→6)]-β-D-galactopyranoside
VI i 42
87 gypsogenin 28-O-β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→6)]-β-D-
glucopyranoside
VI j 43
88 3β-sulfate ester of gypsogenin 28-O-β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-
(1→6)]-β-D-glucopyranoside
VI j 44
89 3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopyrano-
syl gypsogenin 28-O-α-L-arabinopyranosyl-(1→4)-α-L-arabinopyranosyl-(1→3)-β-
D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranosyl ester
VI e 32
90 3-O-β-D-galactopyranosyl-(1→3)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-
xylopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-
β-D-fucopyranosyl ester
VI e 32
91 3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopy-
ranosyl gypsogenin β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-
[3,4-di-O-acetyl-β-D-quinovopyranosyl-(1→4)]-β-D-fucopyranoside
VI k 33
92 3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopy-
ranosyl gypsogenin α-L-arabinopyransyl-(1→3)-β-D-xylopyranosyl-(1→4)-α-L-
rhamnopyranosyl-(1→2)-[3,4-di-O-acetyl-β-D-quinovopyranosyl-(1→4)]-β-D-
fucopyranoside
VI k 33
93 3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopy-
ranosyl gypsogenin 28-β-D-xylopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→3)]-
α-L-rhamnopyranosyl-(1→2)-4-O-trans/cis-p-methoxycinnamoyl-β-D-fucopyranosyl
VI k 33
94 3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-6-O-methyl-β-D-
glucuronopyranosyl gypsogenin 28-β-D-xylopyranosyl-(1→4)-[β-D-glucopyrano-
syl-(1→3)]-α-L-rhamnopyranosyl-(1→2)-4-O-trans/cis-p-methoxycinnamoyl-β-D-
fucopyranoside
VI k 33
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编号 化合物名称 母核 植物来源 参考文献
95/96 3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-6-O-methyl-β-D-
glucuronopyranosyl gypsogenin 28-β-D-xylopyranosyl-(1→4)-[β-D-glucopyrano-
syl-(1→3)]-α-L-rhamnopyranosyl-(1→2)-3-O-trans/cis-p-methoxycinnamoyl-β-D-
fucopyranosyl
VI k 33
97 3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopyr-
anosyl gypsogenin 28-O-β-D-xylopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→3)]-
α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-fucopyranosyl ester
VI l 34
98 3-O-β-D-xylopyranosyl-(1→3)-[β-D-galactopyranosyl-(1→3)-β-D-galactopyrano-
syl-(1→2)]-β-D-glucuronopyranosyl gypsogenin 28-β-D-glucopyranosyl-(1→3)-
[β-D-xylopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)]-α-Lrhamnopyranosyl-(1→2)-
β-D-fucopyranosyl ester
VI l 35
99 3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopy-
ranosyl gypsogenin 28-O-β-D-xylopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-α-
L-rhamnopyranosyl-(1→2)-[(4-O-acetyl)-β-D-quinovopyranosyl-(1→4)]-β-D-
fucopyranosyl ester
VI m 34
100 gypsogenic acid 28-O-β-D-glucopyranosyl-(1→3)-{6-O-[3-hydroxy-3-methylglutaryl]-
β-D-glucopyranosyl-(1→6)}-β-D-galactopyranosyl ester
VI m 34
101 3-{{O-α-L-arabinopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-β-D-glucopy-
ranuronosyl}oxy}-gypsogenin 28-{O-β-D-xylopyranosyl-(1→3)-O-β-D-xylopy-
ranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2)-4-O-[(E)-4-methoxycinnamoyl]-
β-D-fucopyranosyl} ester
VI n 37
102 3-β-O-(β-D-galactopyranosyl)-(1→3)-β-D-glucopyranosyl gypsogenin 28-O-{β-D-
glucopyranosyl-(1→3)-[β-D-xylopyranosyl-(1→4)]-α-L-rhamnopyranosyl-(1→2)-
[β-D-fucopyranosyl-(1→3)]-α-L-arabinopyranosyl ester}
VI n 38
103 junceosides C VI n 38
104 agrostemmoside A VI n 38
105 gypsogenin 28-O-[β-D-glucopyranosyl-(1→2)-β-D-galactopyranosyl-(1→3)]-[β-D-
glucopyranosyl-(1→6)]-β-D-galactopyranoside
VI n 38
106 (3β)-3-O-{β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopy-
ranuronosyl}gypsogenin 28-{α-L-arabinopyranosyl-(1→3)-β-D-xylopyranosyl-
(1→4)-α-L-rhamnopyranosyl-(1→2)-(3-O,4-O-diacetyl-β-D-fucopyranosyl)}ester
VI d 45
107 gypsogenic acid VII a 18,26-28
108 3β-hydroxyolean-12-en-23,28-dioic acid 28-O-[β-D-glucopyranosyl-(1→3)-β-D-
glucopyranosyl-(1→2)][β-D-galactopyranosyl(1→6)]β-D-glucopyranoside
VII i 42
109 3β-hydroxyolean-12-en-23,28-dioic acid 28-O-[β-D-glucopyranosyl-(1→2)-β-D-
galactopyranosyl-(1→3)][β-D-glucopyranosyl(1→6)]β-D-galactopyranoside
VII i 42
110 gypsogenic acid 28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl-(1→6)-[β-
D-glucopyranosyl-(1→3)]-β-D-glucopyranosyl ester
VII e 32
111 3-O-β-D-glucopyranosyl gypsogenic acid 28-O-α-D-galactopyranosyl-(1→6)-β-D-
glucopyranosyl-(1→6)-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranosyl ester
VII e 32
112 (3β)-3-O-(β-D-xylopyranosyl)-gypsogenic acid 28-{β-D-glucopyranosyl-(1→6)-
β-D-galactopyranosyl}ester
VII d 45
中草药 Chinese Traditional and Herbal Drugs 第 46 卷 第 2 期 2015 年 1 月
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续表 5
编号 化合物名称 母核 植物来源 参考文献
113 (3β)-3-O-(β-D-xylopyranosyl)-gypsogenic acid 28-{β-D-xylopyranosyl-(1→2)-[β-
D-glucopyranosyl-(1→6)]-β-D-galactopyranosyl}ester
VII d 45
114 (3β)-3-O-(β-D-xylopyranosyl)-gypsogenic acid 28-{β-D-glucopyranosyl-(1→3)-[β-
D-glucopyranosyl-(1→6)]-β-D-galactopyranosl}ester
VII d 45
115 (3β)-3-O-{β-D-glucopyranosyl-(1→2)-β-D-galactopyranosyl-(1→2)-[β-D-glucopy-
ranosyl-(1→4)]-β-D-galactopyranosyl}gypsogenic acid
VII d 45
116 (3β)-3-O-{β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopy-
ranuronosyl}gypsogenic acid 28-{α-L-arabinopyranosyl-(1→4)-α-L-arabinopy-
ranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-[β-D-
quinovopyranosyl-(1→4)]-β-D-fucopyranosyl}ester
VII d 45
117 vaccaric acid, β-D-glucopyranosyl-(1→3)-[β-D-xylopyranosyl-(1→4)]-α-L-rhamno-
pyranosyl-(1→2)-β-D-fucopyranosyl ester
VIII a 23
118 segetalic acid 28-O-α-L-arabinopyranosyl-(1→4)-α-L-arabinopyranosyl-(1→3)-β-
D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranosyl ester
IX a 25
119 collinsogenin X a 18,27-28,40
120 hederagenin XI a 18,27-28
121 23-sulfate ester of hederagenin 28-O-β-D-glucopyranosyl-(1→2)-[β-D-glucopyrano-
syl (1→6)]-β-D-glucopyranoside
XII j 44
122 3β-O-sulfate gypsogenin 28-O-β-D-glucopyranosyl ester XIII e 46
123 3β-O-sulfate gypsogenin XIII e 46
124 3-O-sulfoechinocystic acid 28-β-glucopyranosyl ester XIV h 47
125 3β-O-sulfate quillaic acid XIV e 46
126 3β-Osulfate oleanolic acid XV e 46
127 oleanolic acid XV a 18,27-28,40
128 3-O-sulfooleanolic acid 28-β-glucopyranosyl ester XV h 47
129 echinocystic acid XVI a 18,27-28
130 3-O-sulfoquillaic acid 28-β-glucopyranosyl ester XVI h 47
131 hederagenin-3-O-sulfate XVII a 18,28
132 3-keto,16α-hydroxy, 24-noroleanolic acid 28-O-α-L-arabiopyranosyl-(1→4)-α-L-
arabinopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-
(1→2)-β-D-fucopyranosyl ester
XVIII a 25
133 hederagonic acid XIX a 18,28
134 (3β,4α,20α)-3,29-dihydroxy-16,23-dioxo-28-norolean-17-en-3-yl-O-β-D-galacto-
pyranosyl-(1→2)-O-[β-D-galactopyranosyl-(1→4)]-β-D-glucopyranuronosidic acid
XX n 37
135 23-O-β-D-glucopyranosyl gypsogenic acid 28-O-β-D-glucopyranosyl-(1→3)-[β-D-
glucopyranosyl-(1→6)]-β-D-glucopyranoside
30
136 (3β)-3-O-(sulfo)lup-20(29)-en-23,28-dioic acid 12
137 (3β)-3-O-(sulfo)lup-20(29)-en-23,28-dioic acid 28-O-β-D-glucopyranosyl ester 12
g-G. pilulifera h-G. trichotoma i-G.capillaris j-G. bermejoi k-G. perfoliata l-G. arrostii m-G. bicolor n-G. paniculata o-G. altissima
中草药 Chinese Traditional and Herbal Drugs 第 46 卷 第 2 期 2015 年 1 月
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144
141
145
142139 140
146 147 148
CHO
OH
H3CO OCH3
OH
O
HO
H3CO
COOH
HO
COOH
O
OH
HO
HO
OH
OH
O
O
HO
O
HO
OH
O
O
HO
O
OH
O
O
HO
OH
OH
O
O
HO
OCH3
OH
O
图 5 石头花属植物的其他成分结构式
Fig. 5 Chemical structures of other compounds from plants in Gypsophila L.
3.2 抗肥胖作用
韩立坤等[52]通过探讨丝石竹水层的总皂苷部
位对高脂肪饮食诱发小鼠肥胖的影响,发现其对胰
脂肪酶活性呈浓度依赖性抑制,对血浆三酰甘油升
高有抑制作用;对高脂肪饮食负荷而导致的体质量
及脂肪量增加有抑制作用,证实其具有抗肥胖作用。
Zheng 等[30]通过测定油酸(甘油三油酸酯中的油酸)
的释放率测定脂肪酶活性,发现长蕊石头花中的皂
苷成分 43、71、135 具有胰脂肪酶抑制作用,当这
3 种化合物的质量浓度均为 1 mg/mL 时,对脂肪酶
活性抑制率分别为 58.2%、99.2%和 50.3%,具有明
显的抗肥胖作用。
3.3 抗糖尿病作用
石头花属中的长蕊石头花、圆锥石头花中的
部分皂苷具有抗糖尿病作用;有很强的 α-葡萄糖
苷酶抑制活性[25,36-37]。α-葡萄糖苷酶抑制剂可以
阻碍膳食碳水化合物的吸收,抑制餐后高血糖
症。Luo 等 [25]发现长蕊石头花中的化合物 65、
118、132 具有比阿卡波糖更强的 α-葡萄糖苷酶
抑制活性。
3.4 保肝作用
从 G. trichotoma Wender. 中分得的 apigenin-O/
C-diglucoside具有抑制CCl4诱导的肝脏氧化损伤的
保护作用[53]。从缕丝花中分得的 isoorientin-2″-O-α-
L-arabinopyranosyl(8)具有抗肝纤维化甚至肝硬化
的作用[11]。
3.5 免疫抑制作用
Luo 等[25]研究表明,从霞草根中分离得到的化
合物38在10~100 μg/mL时能有效增加粒细胞的吞
噬作用(40%~75%),在 100 ng/mL~1 pg/mL 时,
表现出对 T 细胞活化的免疫抑制作用。
3.6 抗氧化作用
黄海兰等[54]发现霞草提取物具有较强的抗氧
化活性。利用 DPPH 法、Marklund、邻二氮菲-Fe2+
氧化法及磷钼络合物法测定各提取物抗氧化活性,
同时与合成抗氧化剂 BHT 进行对照。结果表明,在
实验所测浓度下,醋酸乙酯萃取物清除 DPPH 自由
基能力比同浓度的 BHT 强,其还原能力与 BHT 非
常接近。石油醚萃取物具有很强的清除羟自由基和
过氧自由基能力,且均高于同浓度的 BHT。张凤梅
等[55]发现满天星中的黄酮类化合物 isoorientin-2″-
O-α-L-arabinopyranosyl(8)具有较高的抗氧化活性
(IC50=9.8 μmol/L)。
3.7 其他
霞草挥发油中的化学成分如 squalene(27)具
有抗肿瘤、抗疲劳、抗感染、免疫调节和抗氧化功
效,广泛应用于医药、食品、化妆品工业等领域[21];
naphazoline(29)为拟肾上腺素药,有收缩血管作
用,用于过敏性及炎症性鼻充血、急慢性鼻炎、眼
充血等,对细菌性过敏性结膜炎亦有效,并能减轻
眼睑痉挛;anethole(32)对因化疗或放疗导致的白
细胞减少症及其他原因引起的白细胞减少症有一定
疗效;phenmetrazine(37)为拟交感神经药,与苯
丙胺类似,作用于下丘脑饱感中枢,并影响糖代谢
致食欲减退,体质量下降,可用于治疗肥胖症[20]。
4 结语
石头花属植物中含有非常丰富的化合物,具有
多种药理作用。目前,从石头花属植物中分离得到
的化学成分主要是三萜及其皂苷类。有研究报道,
其中总黄酮的量很高,是很多栽培蔬菜的几倍甚至
上百倍。黄酮类物质具有保肝、降压、抗菌等多种
药理作用[56]。目前,对该属植物的研究虽然已取得
中草药 Chinese Traditional and Herbal Drugs 第 46 卷 第 2 期 2015 年 1 月
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了一些进展,但仍存在一些不足,主要体现在对该
属植物的化学成分方面的研究不够全面,以及药理
活性研究不够深入,如化合物的生物合成途径、单
体化合物的活性筛选以及提高相对分子质量大、极
性大的皂苷类化合物药理活性及生物利用度等方面
的研究都有待进一步加强。因此,还需要利用现代
药学的研究手段,结合细胞生物学、分子生物学等
各相关学科知识,对石头花属中黄酮类、三萜类及
其他有效成分进行合理的开发利用,扩展该属植物
的应用范围,提高应用价值。
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