全 文 :天然产物研究与开发 Nat Prod ResDev 2006 , 18:873-877
文章编号:1001-6880(2006)05-0873-05
收稿日期:2005-03-08 接受日期:2005-05-30
*通讯作者 Tel:86-21-50806600-3502;E-mai l:ycli@mail.shcnc.ac.cn
鹅掌柴属植物化学研究进展
郭夫江 ,李援朝*
(中国科学院上海药物研究所 ,上海 201203)
摘 要:鹅掌柴属(Schefflera)植物是五加科(Araliaceae)藤状灌木 , 其中多种植物被用于治疗风湿痹痛及关节炎。
该属植物的化学成分主要是三萜类化合物及其皂苷 , 本文综述了该属植物的化学成分的研究概况。
关键词:鹅掌柴属;三萜;皂苷;抗风湿
中图分类号:R282.71;Q946 文献标识码:A
Progress on the Chemical Research of Genus Schefflera
GUO Fu-jiang ,LI Yuan-chao*
(Shanghai Institute of Materia Medica , Shanghai Institutes for Biological Sciences ,
Chinese Academy of Sciences , Shanghai 201203 , China)
Abstract:Several plants of the genus Schefflera (Araliaceae)were used as antirheumatic agent.This paper described the
progress on chemical research of this genus.Pentacyclic triterpenoids and saponins were reported to be the major constituents.
Key words:Schefflera;triterpenoids;saponins;antirheumatic agent
鹅掌柴属(Schefflera)植物系五加科(Araliaceae)
藤状灌木 。全世界约有200种 ,中国约37种 ,主要分
布于西南与东南地区 。该属中有不少种可以药用 ,
主要的有鹅掌藤(S.arboricola),鹅掌柴(S.octophyl-
la),广西鹅掌柴(S .kwangsiensis),密脉鹅掌柴(S .
venulosa),扁盘鹅掌柴(S .khasiana)等[ 1] 。《中药大
词典》称其“祛风除湿 , 活血止痛。治风湿痹痛 ,胃
痛 ,跌打骨折 ,外伤出血。” 我国民间多用该属植物
治疗风湿骨痛 、 跌打肿痛 、 骨折挫伤 、 刀伤烫伤 、
腰肌劳损 、咽喉肿痛 、皮炎湿疹等[ 2] 。其中汉桃叶
(广西鹅掌柴)曾被收载于1977年版 《中华人民共
和国药典》 , 其提取物被制成片剂和注射液用于治
疗风湿骨痛。在越南 , 该属植物 S.octophylla 也常
被用于抗关节炎和滋补 , 以及治疗肝病[ 3-5] 。新西
兰的毛利人使用该属植物 S .digitata 治疗皮癣和
其它皮肤病[ 6] 。
在近代的药理研究中 ,Muir AD 等[ 6] 发现从新
西兰 S.digitata中分离的 falcarindiol可以抑制真菌 。
ZhuM 等[ 7 ,8]对 S.bodinieri提取物及其中分离的化
合物进行了一系列的放射性配体受体实验。
由于该属植物众多的生理活性 ,引起了许多学
者的关注 ,上世纪八九十年代对本属植物化学成分
进行了大量研究 。迄今 ,已分离出大约 100种化合
物 ,其中大部分是五环三萜及其苷类成分 ,此外还有
少量甾体 ,萜类 ,长链化合物以及一些寡糖等。为了
更好地开发利用这一药用资源 ,现将该属植物化学
成分进行综述。
1 五环三萜及其苷类
这是该属植物中最主要的成分 。从结构上看 ,
主要有齐墩果烷型(oleanane),乌苏烷型(ursane),羽
扇豆烷型(lupane)。
2 其它
甾体及其甙类 β-谷甾醇(β-sitosterol)[ 9 ,10] ;胡
萝卜甙(β-sitosterol-β-D-glucoside)[ 9 ,10 ,14] ;多孔甾醇
(poriferasterol)[ 36] ;Stigmasterol-3-O-β-D-glucoside[ 23] 。
倍半萜 oplodiol;oplopanone;T-murrolol[ 19]
长 链 化 合物 fakarindiol[ 6 ,19] ;C18-acetylen-
verbindung[ 19] ;(E)-β-Faresene[ 36] ;falcarinol[ 36] ;植醇
phytol[ 19 ,36] ;二十四烷酸(tetracosanoic acid)[ 10] ;三十
烷酸(triacontanoic acid)[ 10] ;生育酚 γ-tocopherol;δ-
tocopherol[ 19] ;docosyl 和 tetracosyl 4-hydroxy-trans-cin-
namate[ 19] ;docosyl , tetracosyl和 hexacosyl 4-hydroxy-cis-
cinnamate[ 19] ;植烷(phytane)[ 19] 。
表 1 从鹅掌柴属植物中分离到的三萜和皂苷
Table 1 Triterpenoids and saponins from the genus of Schefflera
编号
No.
化合物
Compounds
基团
Groups
来源
Resource
文献
Ref.
1 β-amyrin 3β-OH;28-Me S.ve;S.im 9 ,10
2 Oleanolic acid 3β-OH S.oc;S.de;S.im 11 , 12, 18
3 Oleanonic acid 3 =O S.oc;S.ve;S.de 4 ,9 , 12
4 Scheffleraside I 3β-O-β-D-GluA S.de 13
5 Oleanolic acid 3-O-α-L-arabinopyranoside S.de;S.ca 12 , 14
6
3β-O-β-D-galactopyranosyl-(1→3)-[ β-D-glucopyranosyl-(1→4)]-β-D-glucopyra-
nosylolean-12-en-28-oic acid S.di 15
7
3β-O-β-D-galactopyranosyl-(1 → 3)-[ β-D-glucopyranosyl-(1 → 4)] -β-D-glu-
curonopyranosylolean-12-en-28-oic acid S.di 15
8 3-O-[ α-L-rhamnopyranosyl-(1→4)-β-D-glucuronopyranosyl] oleanolic acid S.ar 16
9 3-O-[ α-L-rhamnopyranosyl-(1→4)-β-D-glucuronopyranosyl] echinocystic acid 16α-OH S.ar 16
10
3-O-α-L-rhamnopyranosyl-(1 → 4)-[ α-L-arabinopyranosyl-(1 → 2)-] -β-D-glu-
curonopyranosyl] oleanolic acid S.ar 16
11
3-O-α-L-rhamnopyranosyl-(1 → 4)-[ β-D-galactopyranosyl-(1 → 2)-] -β-D-glu-
curonopyranosyl oleanolic acid
S.ar 16
12
3-O-β-D-apiofuranosyl-(1→4)-[ α-L-arabinopyranosyl-(1→2)-] -β-D-glucuronopy-
ranosyl] oleanolic acid S.ar 16
13
3-O-[ α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-glucuronopyra-
nosyl] oleanolic acid S.lu 35
14 Scheffleroside
3β-O-GlcA-Gal-Fuc; 16α-
OH
S.ca 17
15 Hederagenin 3β-OH;23-CH2OH S.im 18
16 3α, 23-dihydroxyolean-12-en-28-oic acid S.ta 19
17 3α-hydroxyolean-12-en-23 ,28-dioic acid S.ta 19
18 Capi togenic acid 1α, 3β ,16α-OH;23-CH2OH S.ca 14
19 Hederagenin-3-O-α-L-arabinopyranoside S.ca 14
20 Hederagenin-3-O-β-D-glucuronopyranoside-6 -O-methyl ester S.im 18
21 4-epihederagenin-3-O-β-D-glucuronopyranoside-6 -O-methyl ester 24-CH2OH S.im 18
22 Hederagenin-3-O-β-D-6 -acetylglucopyranoside S.im 20
23
3β-O-α-L-arabinopyranosyl-(1→3)-[ β-D-xylopyranosyl-(1→2)] -β-D-glucuronopy-
ranosyl-16α-hydroxyolean-12-ene-28 , 30-dioic acid S.di 15
874 天然产物研究与开发 Vol.18
24
3β-O-α-L-arabinopyranosyl-(1→3)-[ β-D-xylopyranosyl-(1→2)] -β-D-glucuronopy-
ranosyl-16α-O-[ 3-hydroxy-3-methylbutanoyl] olean-12-ene-28 , 30-dioic acid S.di 15
No. Compounds Groups R Resource Ref.
25 Scheffoleoside A 2α, 3β-OH;23-CH2OH -Glc6-Glc4-Rha S.oc 21
26 Scheffoleoside B 2α, 3β-OH;23-CHO -Glc6-Glc4-Rha S.oc 21
27 Cauloside D 3β-O-Ara;23-CH2OH -Glc6-Glc4-Rha S.oc 21
28 Scheffoleoside D 3α-OH;23-COOH -Glc6-Glc4-Rha S.oc 21
29 Scheffoleoside E 3β-O-GlcA2-Gal2-Glc -Glc6-Glc4-Rha S.oc 21
30 Scheffoleoside F 2α, 3β-OH;24-CH2OH -Glc6-Glc4-Rha S.oc 21
31 Schefferaside II 3β-O-β-D-GlcA -Glc6-Glc4-Rha S.de 13
32
3-O-[ β-D-apiofuranosyl-(1→ 4)-β-D-glucuronopyranosyl] -oleanolic acid
28-β-D-glucopyranoside S.ar 16
33
3-O-α-L-rhamnopyranosyl-(1→4)-[ α-L-arabinopyranosyl-(1→2)-] -β-D-
glucuronopyranosyl-oleanolic acid 28-β-D-glucopyranoside S.ar 16
34
3-O-α-L-rhamnopyranosyl-(1→4)-[ β-D-galactopyranosyl-(1→2)-] -β-D-
glucuronopyranosyl oleanolic acid 28-β-D-glucopyranoside S.ar 16
35
3-O-β-D-apiofuranosyl-(1→4)-[ α-L-arabinopyranosyl-(1→2)-] -β-D-glu-
curonopyranosyl〗oleanolic acid 28-O-β-D-glucopyranoside S.ar 16
36
3-O-[ α-L-rhamnopyranosyl-(1 → 4)〗-β-D-glucuronopyranosyl ] oleanolic
acid 28-β-D-glucopyranoside S.ar 22
37
3-O-[ α-L-arabinopyranosyl-(1→2)-β-D-glucuronopyranosyl] oleanolic acid
28-β-D-glucopyranoside S.ar 22
No. Compounds Groups R Resource Ref.
38 3-oxo-20-demethylisoaleuritolic-14(15)-ene-28, 29-dioic acid H S.bo 23
39 3α-hydroxyl-20-demethylisoaleuritolic-14(15)-ene-28 , 30-dioic acid H S.bo 23
40
3-oxo-20-demethylisoaleuritic-14 (15)-ene-28 , 29-dioic acid 28-O-[ α-L-
rhamnopyranosl-(1→4)-O-β-D-glucopyranosyl-(1→6)]-O-β-D-glucopyra-
noside
S.bo 23
41 Bodinitin A 3β-OH;26-H -Glc6-Glc4-Rha S.bo 24
42 Bodinitin B 3β-OH -Glc6-Glc4-Rha S.bo 24
43 Bodinitin C 3=O;26-H -Glc6-Glc4-Rha S.bo 24
44 Bodinitin D =O -Glc6-Glc4-Rha S.bo 24
No. Compounds Groups Resource Ref.
45
3β-hydroxy-isopolygalic-13(14)-ene-28-oic acid 28-O-[ α-L-rhamopyranosyl-(1→4)-O-β-
D-glucopyranosyl(1→6)]-β-D-glucopyranoside 3β-OH;26-H S.bo 25
46
3-oxo-isopolygalic-13 (14)-ene-28-oic acid 28-O-[ β-L-rhamopyranosyl-(1 → 4)-O-β-D-
glucopyranosyl(1→6)]-β-D-glucopyranoside 3=O;26-H S.bo 25
47
3β-hydroxy-i sopolygalic-13(14)-ene-28-oic acid 28-O-β-D-glucopyranosyl(1→6)-β-D-glu-
copyranoside
3β-OH;26-H S.bo 25
48
3β-hydroxy-18-methyl-polygalic-13(14)-ene-28-oic acid 28-O-[ α-L-rhamopyranosyl-(1 →
4)-O-β-D-glucopyranosyl(1→6)]-β-D-glucopyranoside 3β-OH;26-Me S.bo 25
No. Compounds Groups R Resource Ref.
49 α-amyrin 3β-OH;28-Me S.im 10
50 3β ,23-dihydroxy-urs-12-en-28-oic acid H S.im 18
51 Asiatic acid 2α,3β-OH;23-CH2OH H S.oc 26
52 3α-hydroxy-urs-12-ene-23 , 28-dioic acid H S.oc 26
53
3β ,23-dihydroxy-urs-12-en-28-oic acid 3-O-β-D-glucuronopyranoside 6 -O-
methyl ester
H S.im 18
54 Asiaticoside 2α,3β-OH;23-CH2OH -Glc6-Glc4-Rha S.oc 21, 26
55 Scheffuroside D 3α-OH;23-COOH -Glc6-Glc4-Rha S.oc 21, 26
56 Scheffuroside B 2α,3β-OH;23-CHO -Glc6-Glc4-Rha S.oc 21
57 Scheffuroside C 3β-O-Ara;23-CH2OH -Glc6-Glc4-Rha S.oc 21
875Vol.18 郭夫江等:鹅掌柴属植物化学研究进展
58 Scheffuroside E 3β-O-GlcA 2-Gal2-Glc -Glc6-Glc4-Rha S.oc 21
59 Scheffuroside F 2α,3β-OH;24-CH2OH -Glc6-Glc4-Rha S.oc 21
No. Compounds Groups Resource Ref.
60 Betulinic acid 3β-OH S.ve 9
61 3-epi-betulinic acid 3α-OH S.oc 3
62 3-epi-betulinic acid 3-O-sulfate 3α-OSO3H S.oc 27
63 Betulinic acid 3-O-sulfate 3β-OSO3H S.oc 27
64 3α-hydroxylup-20(29)-ene-23 , 28-dioic acid S.ta;S.
oc
19 , 28
65 3α, 11α-dihydroxylup-20(29)-ene-23 ,28-dioic acid S.oc 29
66 3α, 11α-dihydroxylup-20(29)-ene-28-oic acid S.ta;S.
im
19 , 30
67 3α-hydroxylup-20(29)-ene-23 , 28-dioic acid faty acid ester S.oc 11
68
3α-hydroxylup-20(29)-ene-23 , 28-dioic acid 28-O-[ α-L-rhamnopyranosyl-(1→4)-O-β-D-
glucopyranosyl-(1→6)]-β-D-glucopyranoside(Glycoside I) S.oc 3 ,31
69 Betulinic acid glycoside 3β-O-Glc S.ve 9
70 3-epi-betulinic acid 3-O-β-D-glucopyranoside(Glycoside II) 3α-O-Glc S.oc 31
71
3α,11α-dihydroxylup-20(29)–ene-23 , 28-dioic acid 28-O-[ α-L-rhamnopyranosyl-(1→
4)-O-β-D-glucopyranosyl-(1→6)] -β-D-glucopyranoside S.oc 3
72
3-epi-betulinic acid 28-O-[ α-L-rhamnopyranosyl(1→4)-O-β-D-glucopyranosyl-(1→6)] -
β-D-glucopyranoside S.oc 3
73 Lup-20(29)-en-28-oic-3-O-β-D-glucopyranosyl(2→1)–O-β-D-glucopyranoside S.ve 32
74
3-epi-betulinic acid 3-O-sulphate 28-O-[ α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyra-
nosyl-(1→6)]-β-D-glucopyranoside 3α-OSO3H S.oc 33
75
3-epi-betulinic acid 3-O-β-D-glucopyranoside 28-O-[ α-L-rhamnopyranosyl-(1→4)-O-β-
D-glucopyranosyl-(1→6)] -β-D-glucopyranoside S.oc 4
76
3-epi-betulinic acid 3-O-β-D-6 acetylglucopyranoside 28-O-[ α-L-rhamnopyranosyl-(1→
4)-O-β-D-glucopyranosyl-(1→6)] -β-D-glucopyranoside S.oc 5
77
3α-11α-dihydroxylup-20(29)-ene-28-oic acid 28-O-β-D-glucopyranosyl-(1 →6)] -β-D-
glucopyranoside
S.im 34
78
3-O-[ α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-glucuronopyranosyl]
betulinic acid
S.lu 35
79
3-O-[ α-L-rhamnopyranosyl-(1 → 2)-O-β-D-xylopyranosyl-(1 → 2)-β-D-glucuronopyra-
nosyl] betulinic acid S.lu 35
80 3β-O-β-D-xylopyranosyl-(1→2)-β-D-glucuronopyranosyllup-20(29)-en-28-oic acid S.di 15
81
3β-O-β-D-glucopyranosyl-(1→3)-[ β-D-xylopyranosyl-(1→2)] -β-D-glucuronopyranosyl-
23-hydroxylup-20(29)-en-28-oic acid S.di 15
82
3β-O-β-D-xylopyranosyl-(1→ 2)-β-D-glucuronopyranosyl-23-hydroxylup-20(29)-en-28-
oic acid
S.di 15
83 3β-O-β-D-glucuronopyranosyl-23-hydroxylup-20(29)-en-28-oic acid S.di 15
84
3β-O-β-D-glucopyranosyl-(1→3)-β-D-glucuronopyranosyl-23-hydroxylup-20(29)-en-28-
oic acid
S.di 15
85
3β-O-β-D-xylopyranosyl-(1 → 2)-β-D-glucuronopyranosyl-23-oxolup-20(29)-en-28-oic
acid
S.di 15
86
3β-O-β-D-glucopyranosyl-(1 →3)-β-D-glucuronopyranosyl-23-oxolup-20(29)-en-28-oic
acid
S.di 15
87 3β-O-β-D-glucuronopyranosyl-23-oxolup-20(29)-en-28-oic acid S.di 15
S.ar = S.arboricola;S.bo = S.bodinieri;S.ca = S.capitata;S.de = S.delavayi;S.di = S.divaricata;S.im = S.impressa;S.lu = S.lu-
cantha;S.oc = S.octophylla;S.ta = S.taiwaniana;S.ve = S.venulosa;
单糖及寡糖 D-sorbitol[ 23] ;α-L-rhamnopyranosyl
(1 →4)-O-β-D-glucopyranosyl (1→6)β-D-glucopyra-
noside 和它的异构体[ 4 ,23] 。
类胡萝卜素 loliolide[ 19] 。
虽然科研工作者对鹅掌柴属植物进行许多的研
究 ,但主要集中在化学方面 ,近代药理工作并不多见 ,
其有效部位 ,有效成分 ,作用机理仍不明确 。对该属
植物进一步研究对它的开发利用有着重要意义。
876 天然产物研究与开发 Vol.18
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877Vol.18 郭夫江等:鹅掌柴属植物化学研究进展