全 文 ：植物分类学报 46 (5): 692–723 (2008) doi: 10.3724/SP.J.1002.2008.07112
Journal of Systematics and Evolution (formerly Acta Phytotaxonomica Sinica) http://www.plantsystematics.com
五味子科药用植物亲缘学初探
许利嘉 刘海涛 彭 勇* 肖培根
(中国医学科学院中国协和医科大学药用植物研究所 北京 100094)
A preliminary pharmacophylogenetic investigation in Schisandraceae
Li-Jia XU Hai-Tao LIU Yong PENG* Pei-Gen XIAO
(Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences, Peking Union Medical College, Beijing 100094, China)
Abstract The family Schisandraceae (Magnoliiadae) contains approximately sixty species which are disjunctly
distributed in the southeast of Asia and North America. It was divided into two genera, Schisandra and Kadsura,
represented by 29 species in China, 19 in Schisandra and 10 in Kadsura. This paper reviews current knowledge
about the chemistry, ethnopharmacology and pharmacology of the family in an attempt to present a preliminary
study into the pharmacophylogenetics of the family as a whole. Dibenzocyclooctadiene lignans (I) are considered
to be the main chemical components of the family. Despite their traditionally recognized hepatoprotective func-
tion, they also exhibit anti-oxidant, anti-cancer and anti-HIV potential. Those dibenzocyclooctadiene lignans (I)
possessing hydroxyl or angeloyloxy groups at C-6 or C-9 in the ethylidene-cyclooctane ring tend to exhibit a
higher anti-cancer activity. Spirobenzofuranoid dibenzocyclooctadienes (II), mostly present in Kadsura, contain a
special tetrahydrofuran ring spanning the biphenyl linkage and these demonstrate particular anti-PAF activities.
This supports the traditional use of Kadsura to improve blood circulation and “remove dampness”. Spirobenzofu-
ranoid dibenzocyclooctadienes (II) could be considered as the bioactive marker compounds in Kadsura and hence
markers for assessing quality. The distribution of all known lignans in the family showed that Kadsura is rela-
tively advanced in evolution. Cycloartanone triterpenes occur in both Schisandra and Kadsura. Those with the
A-ring open (II) tend to exhibit greater anti-cancer and anti-HIV activity. 7/7/5/6 triterpene lactones (IV), showing
strong cytotoxicity, have only recently been discovered in Kadsura longipedunculata and as such have potential
as anticancer agents. Recently, novel nortriterpenoids possessing a unique skeleton were found in S. lancifolia and
S. micrantha; some exhibited clear anti-cancer or anti-HIV activity and are the subject of separate studies.
Key words chemotaxonomy, ethnopharmacology, pharmacophylogenetics, Schisandraceae.
摘要 五味子科Schisandraceae隶属于双子叶植物门木兰亚纲Magnoliidae八角目Illiciales, 全球分布约60种, 包括两个属: 五
味子属Schisandra和南五味子属Kadsura, 间断分布于亚洲东南部和北美东南部。本文归纳了中国五味子科植物两大类活性成
分——木脂素和三萜的分布规律、传统疗效和现代药理活性, 并对中国五味子科的药用植物亲缘学进行了初探。联苯环辛烯
类木脂素(I)集中分布于五味子科植物, 可以被认为是五味子科植物的特征性化学成分, 除了传统的保肝作用外, 这类化合物
中很多具有潜在的抗氧化、抗肿瘤和抗HIV活性, 一些联苯环辛烯类的木脂素, 尤其是在八元环C-6、C-9位上具有羟基或者
酯化取代具有更好的抗HIV和抗肿瘤活性; 而螺苯骈呋喃型联苯环辛烯类木脂素(II)绝大多数存在于南五味子属, 其特殊的
螺苯骈呋喃环及其钙拮抗、抗凝血和抑制血小板聚集的活性, 不仅初步说明了民间南五味子属药用植物藤茎具有较强活血化
瘀药理作用的活性物质基础, 也提示在对南五味子属的药材质量标准研究中, 可以考虑以此类成分作为定性定量指标。五味
子科植物中木脂素成分的分布规律提示, 在演化程度上五味子属植物较南五味子属植物更原始。环菠萝蜜烷类三萜在五味子
属和南五味子属均有分布, 尤其是A环开环的环菠萝蜜烷类三萜(II)在抗HIV和抗肿瘤活性方面具有很好的潜力, 而结构更进
化的7/7/5/6型三萜内酯(IV)显示了很强的细胞毒活性, 目前只在南五味子属的长梗南五味子K. longipedunculata中发现。从五
味子属的小花五味子S. micrantha和狭叶五味子S. lancifolia中分离得到的多个成环复杂且高度氧化的类三萜内酯中也发现具
有抗肿瘤和抗HIV潜力。
关键词 化学分类学; 传统药物学; 药用植物亲缘学; 五味子科
五味子科Schisandraceae隶属于双子叶植物门 木兰亚纲Magnoliidae八角目Illiciales, 包括两个属:
五味子属Schisandra Michx.和南五味子属Kadsura
Kaempf. ex Juss.。该科植物为木质藤本, 共约60种,
———————————
2007-08-27 收稿, 2008-04-15 收修改稿。
* 通讯作者(Author for correspondence. E-mail: ypeng@implad.ac.cn)。
许利嘉等: 五味子科药用植物亲缘学初探
693
间断分布于亚洲东南部和北美东南部。我国是世界
上五味子科植物资源最丰富的国家, 两属均产, 主
要分布于中南部和西南部。五味子属约30种, 主产
于亚洲东部和东南部 , 仅1种Schisandra glabra
(Brickell) Rehder产于美国东南部, 我国约有19种,
南北均有分布; 南五味子属约28种, 主产于亚洲东
部和东南部, 我国约有10种, 相对集中于西南部和
东南部。
1 五味子科植物分类学研究概况
Brickell (1803年2月底–3月初)发表Stellandria
glabra Brickell, 同年4月, Michaux发表Schisandra
coccinea Michx., 属名 Stellandria长期被忽视。
Rehder (1944)建议保留Schisandra Michx.作为五味
子属的学名, 并以Brickell的植物为基本名, 确定五
味 子 属 的 模 式 种 Schisandra glabra (Brickell)
Rehder, 被人们沿用至今。1810年, de Jussieu发表南
五味子属Kadsura Kaempf. ex Juss.的学名, Dunal
(1817)以Linnaeus的植物为基本名, 确定了南五味
子属的模式种为Kadsura japonica (L.) Dunal。1830
年, Blume正式描述了五味子科“Schizandreae”, 提
出它与木兰科Magnoliaceae近缘。Don (1831)将该名
扩改为Schizandraceae。1947年Smith发表《Schisan-
draceae》专著, 对五味子科进行了全面研究, 将
Schisandra属分为4组, 并对南五味子属进行了属下
分类, 包括22种。
五味子科建立以来, 中外学者们运用形态学、
孢粉学、胚胎学与细胞学、现代分子系统学等多种
手段对该科的系统位置、两属之间关系及属下分类
进行了大量的研究。对于五味子科的系统位置, 传
统上一致认为五味子科和木兰科关系很近, 它们在
花的形态上特性一致, 因此很长一段时间五味子类
被放在木兰科中。随着各个分支学科的研究发展,
五味子科的系统发育工作不断丰富和完善, 人们在
研究中发现五味子类和木兰科相差甚远, 晚近的分
类学家(Lawrence, 1915; Cronquist, 1968; Takhtajan,
1969; Thorne, 1992)将原隶属于木兰科的木兰族、八
角族和五味子族分别独立为三个科。而八角科和五
味子科由于在很多性状上有别于木兰亚纲其他类
群而被另立为八角目 (胡先骕 , 1950; Heywood,
1971; Dahlgren et al., 1985; Cronquist, 1988; Takhta-
jan, 1997)。五味子科从传统的木兰科中分出, 独立
为科, 目前已被大多数学者接受, 且多方面证据支
持它与八角科形成一个很紧密的类群, 其共同特征
为具三沟或其衍生类型的花粉和毛茛型Ranalean
type的分泌细胞(Bailey & Nast, 1948), Smith (1947)
揭示此两科都是出自同一个祖干上的明显衍生物,
但向不同方向特化而每个有各自的某些原始特征
保留。杨志荣和林祁(2007)通过比较五味子科与八
角科Illiciaceae的木材解剖特征, 进一步证明两个科
的亲缘关系很近 , 不支持将五味子科从八角目
Illiciales中独立出来成立五味子目Schisandrales的
观点。五味子科分为五味子属和南五味子属两个类
群, 也得到多方面的支持, 为植物分类学界所接受,
大多数学者认可传统2属的划分, 其区别主要在于
雌花花托倒卵形或椭圆形(南五味子属)或圆锥至圆
柱形(北五味子)。但到底哪一个属原始哪一个属进
化, 似乎仍不统一, 且各有证据。目前主要有三种
观点 : 1. 五味子属系统位置在南五味子属之前
(Smith, 1947), 2. 南五味子属系统位置在五味子属
之前(刘玉壶, 1984), 3. 两属起源于共同祖先, 平行
进化或沿不同路线演化(孙成仁, 2000; 王彦涵等,
2003)。至于五味子科的属下分类, 分歧更多, 较具
有代表性的有: Smith (1947)在五味子属下设4组:
多蕊五味子组sect. Pleiostema A. C. Smith (包括华
中五味子群和大花五味子群)、少蕊五味子组sect.
Maximowiczia (Rupr.) Law、五味子组sect. Schisan-
dra、团蕊五味子组sect. Sphaerostema (Blume) Y. H.
Law (包括团蕊五味子群和重瓣五味子群); 将南五
味子属分为3个组: 离蕊南五味子组sect. Cosbaea
(Lem.) Law、南五味子组sect. Kadsura和南洋五味子
组sect. Sarcocarpon (Blume) A. C. Smith。刘玉壶
(1996)在中国五味子科的属下等级划分中将Smith
系统中组的等级升至亚属, 同时将华中五味子群与
大花五味子群分开, 团蕊五味子群和重瓣五味子群
分开, 设置6个亚属; 在南五味子属下, 合并离蕊南
五味子组、南五味子组于离蕊南五味子亚属subgen.
Cosbaea (Lem.) Law, 设立2个亚属, 分别为离蕊南
五味子亚属subgen. Cosbaea (Lem.) Law和南五味子
亚属subgen. Kadsura。Saunders (1998)在五味子属中
设亚属和组两个属下等级, 将华中五味子群与大花
五味子群分开, 分置多蕊五味子亚属subgen. Pleio-
stema (A. C. Smith) Law和中华五味子亚属subgen.
植物分类学报 Journal of Systematics and Evolution 2008 46卷5期 694
Sinoschisandra Law, 保留Smith系统的少蕊五味子
组、五味子组和团蕊五味子组, 并将其置于五味子
亚属subgen. Schisandra (Blume) Y. H. Law之中; 同
时Saunders (1998, 2000)支持刘玉壶关于在南五味
子属下建立2个亚属的观点, 并在后一个亚属中保
留了Smith系统的2个组。比较这三个学者的分类系
统, 主要分歧在五味子属下的分类, 包括华中五味
子群与大花五味子群是否分开; 团蕊五味子群和重
瓣五味子群是否分开; 组和亚属的分类等级能否体
现五味子属的进化历程和进化层次。关于南五味子
属下分类, 意见相对比较统一, 但属下类群的系统
关系, 不同研究得出的结论还存在着分歧, 如王彦
涵等(2003)对南五味子属下几个类群的rbcL基因分
析的结果与其形态学是相互矛盾的。
近些年, 许多学者又通过各种方法对五味子科
的分类系统进行修正。林祁(2000, 2002)在野外调查
的基础上, 结合大量标本考证, 对世界范围的五味
子属和南五味子属作出分类学订正, 并确认五味子
属10种, 南五味子属11种。Liu等(2006)分析了五味
子科的核DNA ITS和叶绿体DNA trnL-F基因序列,
构建了五味子科的系统发育, 认为五味子科分为两
大支: 一支完全是由五味子属Schisandra的种组成;
另一支则既包含了五味子属的种, 又包含南五味子
属Kadsura的种, 即将Smith (1947)系统中五味子属
的团蕊五味子组结合到南五味子属中。林祁和杨志
荣(2007)根据五味子属植物的33个形态性状及其性
状分析, 经过分支分析, 提出一个新的五味子属分
类系统: 将五味子属分为五味子亚属和团蕊五味子
亚属subgen. Sphaerostema (Blume) Y. H. Law; 将五
味子亚属分为多蕊五味子组、少蕊五味子组、中华
五味子组sect. Sinoschisandra (Y. H. Law) Q. Lin &
Z. R. Yang和五味子组。杨志荣和林祁(2007)根据木
材解剖性状对五味子科进行UPGMA聚类分析, 所
得结果显示南五味子属和五味子属在木材解剖特
征方面有一定的交叉和重叠, 这与分子系统学的结
论一致, 表明这两个属关系密切, 可能起源于共同
的祖先。Wang等(2007)测序了五味子科内14种植物
的叶绿体matK区和rpl16内含子区, 分析得出铁箍
散S. propinqua (Wall.) Baill. var. sinensis Oliv.和重
瓣五味子S. plena A. C. Smith嵌套在南五味子属内。
综上所述, 有关五味子科的分类、演化和系统
地位研究, 目前尚未达到统一的认识。
2 五味子科亲缘关系与化学成分
已有的化学研究结果表明, 木兰科的特征性成
分为异喹啉类生物碱和新木脂素, 并无三萜类成
分; 木脂素和三萜为五味子科植物的化学特征, 其
中联苯环辛烯类木脂素在植物界中集中分布于五
味子科, 极少数存在于其亲缘关系较远的植物, 因
此联苯环辛烯类木脂素是五味子科的特征性成分,
具有分类学意义, 而木兰科植物中没有发现此类木
脂素; 迄今为止, 在五味子科和八角科中未发现生
物碱; 而环菠萝蜜烷类型三萜和A环裂环菠萝蜜烷
类型三萜在五味子科和八角科中均分离得到, 推测
两科有共同起源。因此, 五味子科从传统木兰科中
分出, 独立为科, 与八角科亲缘关系较近, 这一观
点不仅从形态学、孢粉学、胚胎学以及细胞学方面
得到支持, 而且得到了化学分类的佐证。
2.1 五味子植物中的木脂素及其分类学意义
木脂素是五味子科植物中的主要生物活性成
分, 结构类型多, 立体化学复杂。迄今为止从该科
植物中分到的木脂素有200多个, 根据骨架类型可
分为五大类: I. 联苯环辛烯类(dibenzocyclooctadi-
enes; 图1; 表1); II. 螺苯骈呋喃型联苯环辛烯类
(spirobenzofuranoid dibenzocyclooctadienes; 图2; 表
2); III. 芳基四氢萘类(aryltetralins; 图3; 表3); IV.
二芳基丁烷类(diarylbutanes; 图4; 表4); V. 四氢呋
喃类(tetrahydrofurans; 图5; 表5)。
上述5种类型均属于简单木脂素, 从生源途径
上来说, 二芳基丁烷类木脂素是其他4类木脂素的
生物合成前体, 芳基四氢萘类木脂素和四氢呋喃类
木脂素应该是从二芳基丁烷类木脂素衍化而来的,
属相对进化的化学成分; 螺苯骈呋喃型联苯环辛烯
类木脂素是具有酚羟基结构的联苯环辛烯类木脂
素氧化环合的产物, 也属于进化的化学成分(图6;
表6)。
五大类木脂素在五味子科植物中的分布显示
出一定的规律性: 联苯环辛烯木脂素丰富多样, 化
合物数为木脂素类的一半以上, 根据构型构象又可
分为S-TBC (twist boat chair)(1-89, 138-139), R-TBC
(90-116), S-TB (118-133), 其中S-TBC类型木脂素
占据一半以上, 联苯环上除了C-4和C-11位有2个芳
质子之外, 其他位置(C1-3和C-12-14)均为含氧取
代, 包括甲氧基、亚甲二氧基、羟基和酯基, 酯基
许利嘉等: 五味子科药用植物亲缘学初探
695
图1 五味子科植物中联苯环辛烯类木脂素成分的结构
Fig. 1. Structures of dibenzocyclooctadienes from Schisandraceae.
表1 五味子科植物中联苯环辛烯类木脂素成分
Table 1 Dibenzocyclooctadienes from Schisandraceae
序号
No.
化合物名称
Compound
结构1)
Structure1)
来源植物2)
Plant source2)
文献
Reference
1
schisandrin C
(wuweizisu C)
R1+R2=R5+R6=CH2, R3=R4=CH3,
R7=R8=H
五味子Schisandra chinensis (Turcz.) Baill. (f, s)
球蕊五味子S. sphaerandra Stapf (s)
合蕊五味子S. propinqua (Wall.) Baill. (s)
凤庆南五味子Kadsura interior A. C. Smith (s)
Ikeya et al., 1982b
Guo et al., 2003
Chen et al., 2001c
Chen et al., 2002a
2
gomisin N
R1+R2=CH2, R3=R4=R5=R6=CH3,
R7=R8=H
五味子S. chinensis (f, s)
合蕊五味子S. propinqua (s)
Ikeya et al., 1978a
Chen et al., 2001a
3 (–)-gomisin K1 R1=R7=R8=H, R2=R3=R4=R5=CH3 五味子S. chinensis (f) Ikeya et al., 1980a
4
(–)-gomisin L1
R1=R2=CH3, R3=R7=R8=H,
R5+R6=CH2
五味子S. chinensis (f)
Ikeya et al., 1982c
5
(–)-gomisin L2
R1=R7=R8=H, R2=R3=CH3,
R5+R6=CH2
五味子S. chinensis (f) Ikeya et al., 1982c
6
gomisin J
R1=R6=R7=R8=H,
R2=R3=R4=R5=CH3
五味子S. chinensis (f)
黑老虎K. coccinea (Lem.) A. C. Smith (s)
红花五味子S. rubriflora (Planch.) Rehd. & Wils. (f)
Ikeya et al., 1978b
Li et al., 1985a
Chen et al., 2006
7
(–)-rubschisandrin R1=R2=R3=R4=CH3, R5+R6=CH2,
R7=R8=H
红花五味子S. rubriflora (f) Wang & Chen, 1985
8
kadsurin
R1+R2=CH2, R3=R4=R5=R6=CH3,
R7=H, R8=OAc
日本南五味子 K. japonica (L.) Dunal (s)
凤庆南五味子K. interior (s)
异形南五味子K. Heteroclita (Roxb.) Craib (s)
红花五味子S. rubriflora (s)
Chen et al., 1973
Ding & Luo, 1990
Chen et al., 1992
Li et al., 2004
9
binankadsurin A
R1+R2=CH2, R3=R5=R6=CH3,
R4=R7=H, R8=OH
长梗南五味子K. longipedunculata Finet & Gagnep. (s)
Kadsura sp. (s)
Li et al., 1991
Liu & Zhou, 1991
10
acetyl-binankadsurin
A
R1+R2=CH2, R3=R5=R6=CH3,
R4=R7=H, R8=OAc
日本南五味子K. japonica (f)
Kadsura sp. (s)
Ookawa et al., 1981
Liu & Zhou, 1991
11
angeloyl-
binankadsurin A
R1+R2=CH2, R3=R5=R6=CH3,
R4=R7=H, R8=OAng
日本南五味子K. japonica (f) Ookawa et al., 1981
12
caproyl-
binankadsurin A
R1+R2=CH2, R3=R5=R6=CH3,
R4=R7=H, R8=OCap
日本南五味子K. japonica (f) Ookawa et al., 1981
13 benzoyl-
binankadsurin A
R1+R2=CH2, R3=R5=R6=CH3,
R4=R7=H, R8=OBz
长梗南五味子K. longipedunculata (s)
Li et al., 1991
植物分类学报 Journal of Systematics and Evolution 2008 46卷5期 696
表1 (续) Table 1 (continued)
序号
No.
化合物名称
Compound
结构1)
Structure1)
来源植物2)
Plant source2)
文献
Reference
14
butyryl-
binankadsurin A
R1+R2=CH2, R3=R5=R6=CH3,
R4=R7=H, R8=Obutanoyl
Kadsura sp. (s) Liu & Zhou, 1991
15
isovaleroyl-
binankadsurin A
R1+R2=CH2, R3=R5=R6=CH3,
R4=R7=H,
R8=O-3-methylbutanoyl
长梗南五味子K. longipedunculata (s)
Li et al., 1991
16
isobutyroyl-
binankadsurin A
R1+R2=CH2, R3=R5=R6=CH3,
R4=R7=H,
R8=O-2-methylpropanoyl
长梗南五味子K. longipedunculata (s)
Li et al., 1991
17
heteroclitin A
R1+R2=CH2, R3=R4=R5=R6=CH3,
R7=H, R8=O-2-methylbutanoyl
异形南五味子K. heteroclita (s)
合蕊五味子S. propinqua (s)
Chen et al., 1992
Xu et al., 2006
18
heteroclitin B
R1+R2=CH2, R3=R4=R5=R6=CH3,
R7=H, R8=OAng
异形南五味子K. heteroclita (s)
红花五味子S. rubriflora (s)
Chen et al., 1992
Li et al., 2004a
19
heteroclitin C
R1+R2=CH2, R3=R4=R5=R6=CH3,
R7=H, R8=OTig
异形南五味子K. heteroclita (s)
红花五味子S. rubriflora (s)
Chen et al., 1992
Li et al., 2004a
20
angeloylbinankad-
surin B
R1=R2=R3=R5=R6=CH3,
R4=R7=H, R8=OAng
日本南五味子K. japonica (f, s)
Ookawa et al., 1995
21
acetylbinankadsurin B R1=R2=R3=R5=R6=CH3,
R4=R7=H, R8=OAc
日本南五味子K. japonica (f, s)
Ookawa et al., 1995
22
deangeloyl-
schisantherin F
R1=R4=R7=H,
R2=R3=R5=R6=CH3, R8=OH
日本南五味子K. japonica (s)
Ookawa et al., 1995
23
schisantherin F
R1=R7=H, R3=R5=R6=CH3,
R4=Ang, R8=OH
Kadsura sp. (s) Liu & Ma, 1988a
24
gomisin U
R1=R8=H, R2=R3=R4=R5=R6=CH3,
R7=OH
华中五味子S. sphenanthera (f)
Ikeya et al., 1991
25
benzoylgomisin U
R1=R8=H, R2=R3=R4=R5=R6=CH3,
R7=OBz
华中五味子S. sphenanthera (f)
Ikeya et al., 1991
26
tigloylgomisin O
R1+R2=CH2, R3=R4=R5=R6=CH3,
R7=OTig, R8=H
华中五味子S. sphenanthera (f)
Ikeya et al., 1991
Jiang et al., 2005
27
epigomisin O
R1+R2=CH2, R3=R4=R5=R6=CH3,
R7=α-OH, R8=H
五味子S. chinensis (f)
华中五味子S. sphenanthera (f)
红花五味子S. rubriflora (s)
Ikeya et al., 1979a
Ikeya et al., 1991
Chen et al., 2006
28
gomisin S
R1=R8=H, R2=R3=R4=R5=R6=CH3,
R7=α-OH, R8=H
五味子S. chinensis (f) Ikeya et al., 1988a
29
Schisantherin B
R1+R2=CH2, R3=R4=R5=R6=CH3,
R7=OAng, R8=H
华中五味子S. sphenanthera (f)
红花五味子S. rubriflora (s)
Liu et al., 1978a
Chen et al., 2006
30
schisantherin L
R1+R2=R5+R6=CH2, R3=R4=CH3,
R7=OAng, R8=OH
黑老虎K. coccinea (s)
Liu & Li, 1993
31
acetylschisanthterin L
R1+R 2=R5+R6=CH2, R3=R4=CH3,
R7=OAng, R8=OAc
黑老虎K. coccinea (s)
Liu & Li, 1993
32
schisantherin M
R1+R2=R5+R6=CH2, R3=R4=CH3,
R7=OAng, R8=OTig
黑老虎K. coccinea (s)
Liu & Li, 1993
33
schisantherin N
R1+R2=R5+R6=CH2, R3=R4=CH3,
R7=OAng, R8=OAng
黑老虎K. coccinea (s)
Liu & Li, 1993
34
schisantherin P
R1+R2=R5+R6=CH2, R3=R4=CH3,
R7=OH, R8=OH
黑老虎K. coccinea (s)
狭叶南五味子K. angustifolia (s)
Liu & Li, 1995a
Chen et al., 1998a
35
angustifolin A
R1+R2=R5+R6=CH2, R3=R4=CH3,
R7=OBz, R8=OBz
狭叶南五味子K. angustifolia A. C. Smith (s)
Chen et al., 1998b
36
angustifolin B
R1+R2=R5+R6=CH2, R3=R4=CH3,
R7=OBz, R8=OAc
狭叶南五味子K. angustifolia (s)
Chen et al., 1998b
37
angustifolin C
R1+R2=R5+R6=CH2, R3=R4=CH3,
R7=OBz, R8=OH
狭叶南五味子K. angustifolia (s)
Chen et al., 1998b
38
angustifolin D
R1+R2=R5+R6=CH2, R3=R4=CH3,
R7=OAc, R8=OAc
狭叶南五味子K. angustifolia (s)
Chen et al., 1998a
39
renchangianin C
R1=R2=R5=R 6=CH3, R3=R4=H,
R7=OCin, R8=OAng
仁昌南五味子K. renchangiana S. F. Lan (s)
Chen et al., 2004a
40
rubriflorin A
R1+R2=CH2, R3=R4=R5=R6=CH3,
R7=OAng, R8=OAc
红花五味子S. rubriflora (s)
Li et al., 2004 a
41
propinquanin D
R1=H, R2=R3=R5=R6=CH3,
R4=Ang, R7=OH, R8=OAc
合蕊五味子S. propinqua (s)
Xu et al., 2006
许利嘉等: 五味子科药用植物亲缘学初探
697
表1 (续) Table 1 (continued)
序号
No.
化合物名称
Compound
结构1)
Structure1)
来源植物2)
Plant source2)
文献
Reference
42
longipedunin A
R1+R2=CH2, R3=R5=R6=CH3,
R4=R7=H, R8=OCin
长梗南五味子K. longipedunculata (s)
Sun et al., 2006
43
longipedunin B
R1+R2=CH2, R3=R5=R6=CH3,
R4=R7=H, R8=OAc
长梗南五味子K. longipedunculata (s)
Sun et al., 2006
44
rubriflorin B
R1=R2=R4=R5=R6=CH3, R3=H,
R7=H, R8=Oxo
红花五味子S. rubriflora (s)
Li et al., 2004a
45
schizanrin L
R1=R2=R3=R4=R5=R6=CH3,
R7=OBz, R8=H
日本南五味子K. japonica (f, s) Kuo et al., 2005b
46
ananosin A
R1+R2=CH2, R3=R4=R5=R6=CH3,
R7=OTig, R8=OH
中泰南五味子K. ananosma Kerr (s)
Chen et al., 2001e
47
acetylgomisin R
R1+R2=CH2,R3=R4=CH3,
R5+R6=CH2 R7=OAc, R8=H
合蕊五味子S. propinqua (s)
Chen et al., 2001a
48 rubrifloralignan A R1=R2=R5=R6=CH3,
R3=R4=R7=R8=H
红花五味子S. rubriflora (s)
Tian et al., 2006
49 rubrisandrin A R1=R2=R4=R5=CH3,
R3=R6=R7=R8=H or
R2=R3=R5=R6=CH3,
R1=R4=R7=R8=H
红花五味子S. rubriflora (s)
Chen et al., 2006
50 rubrisandrin B R1=R2=R5=R6=CH3,
R3=R4=R7=R8=H
红花五味子S. rubriflora (s)
Chen et al., 2006
51 angeloyl-(+)-gomisi
n K3
R1=R2=R5=R6=CH3, R3=Ang,
R7=R8=H
合蕊五味子S. propinqua (s)
Lei et al., 2007
52 methylisogomisin O R1=R2=R3=R4=CH3,
R5+R6=CH2, R7=OCH3, R8=H
合蕊五味子S. propinqua var. propinqua (s)
Lei et al., 2007
53 kadsuphilins D R1+R2=CH2, R3=R5=R6=CH3,
R4=H, R7=OH, R8=OAc
菲律宾五味子K. philippinensis Elm. (s)
Shen et al., 2007
54 kadsuphilins F R1+R2=CH2, R3=R5=R6=CH3,
R4=H, R7=OH, R8=OBz
菲律宾五味子K. philippinensis (s)
Shen et al., 2007
55 kadsuphilins C R1+R2=CH2, R3=R5=R6=CH3,
R4=H, R7= OBz, R8=OAc
菲律宾五味子K. philippinensis (s)
Shen et al., 2007
56 kadsuphilins E R1=R2=R3=R5=R6=CH3,
R4=H, R7=OH, R8=OBz
菲律宾五味子K. philippinensis (s)
Shen et al., 2007
57 gomisin B
R1+R2=CH2, R3=R4=R5=R6=CH3,
R7=OAng, R8=H
五味子S. chinensis (f)
华中五味子S. sphenanthera (f)
长梗南五味子K. longipedunculata (s)
合蕊五味子S. propinqua
阿里山五味子S. arisanensis Hayata (s)
Ikeya et al., 1979c
Liu et al., 1978a
Li & Chen, 1986
Chen et al., 2001a
Wu et al., 2003
58
gomisin C
(schisantherin A)
R1+R2= CH2, R3=R4=R5=R6=CH3,
R7=OBz, R8=H
五味子S. chinensis (f)
华中五味子S. sphenanthera (f, s)
合蕊五味子S. propinqua (s)
翼梗五味子S. henryi Clarke (f, s)
凤庆南五味子K. interior (s)
Ikeya et al., 1979c
Liu et al., 1978a
Yue et al., 1994
Chen et al., 2001a
Chen et al., 2005b
Chen et al., 2002a
59
gomisin F
R1=R2=R3=R4=CH3, R5+R6=CH2,
R7=OAng, R8=H
五味子S. chinensis (f)
Taguchi et al., 1977
60
gomisin G
R1=R2=R3=R4=CH3, R5+R6=CH2,
R7=OBz, R8=H
五味子S. chinensis (f)
小花五味子S. micrantha (s)
翼梗五味子S. henryi (s)
阿里山五味子S. arisanensis (s)
合蕊五味子S. propinqua (s)
凤庆南五味子K. interior (s)
Taguchi et al., 1977
Li et al., 2005a
Chen et al., 2005
Wu et al., 2003
Chen et al., 2001a
Chen et al., 2002a
61 benzoylgomisin Q
R1=R2=R3=R4=R5=R6=CH3,
R7=OBz, R8=H
华中五味子S. sphenanthera (f, s)
翼梗五味子S. henryi (s)
Ikeya et al., 1990
Chen et al., 2005b
62
angeloylgomisin Q
R1=R2=R3=R4=R5=R6=CH3,
R7=OAng, R8=H
五味子S. chinensis (f) Ikeya et al., 1979b
63
interiotherin B
R1+R2=R5+R6=CH2, R3=R4=CH3,
R7=OAng, R8=H
凤庆南五味子K. interior (s) Chen et al., 1996
64
interiotherin C
R1+R2=CH2, R3=R4=R5=R6=CH3,
R7=OAng, R8=OAc
凤庆南五味子K. interior (s) Chen et al., 2002a
65
schisantherin C
R1+R2=CH2, R3=R4=R5=R6=CH3,
R7=OTig, R8=H
华中五味子S. sphenanthera (f)
五味子S. chinensis (f)
Liu et al., 1978a
Ikeya et al., 1979c
植物分类学报 Journal of Systematics and Evolution 2008 46卷5期 698
表1 (续) Table 1 (continued)
序号
No.
化合物名称
Compound
结构1)
Structure1)
来源植物2)
Plant source2)
文献
Reference
66
schisantherin D
R1+R2=R5+R6=CH2, R3=R4=CH3,
R7=OBz, R8=H
华中五味子S. sphenanthera (f)
五味子S. chinensis (f)
凤庆南五味子K. interior (s)
Liu et al., 1978a
Ikeya et al., 1982b
Yue et al., 1994
Chen et al., 1996
67
schisantherin E
R1=R8=H, R7=Obz,
R2=R3=R4=R5=R6=CH3
华中五味子S. sphenanthera (f)
Liu et al., 1978a
68
schisantherin G
R1+R2=CH2, R3=H, R8=OAc
R4=R5=R6=CH3, R7=OAng,
Kadsura sp. (s) Liu & Ma, 1988b
69
schisantherin H
R1+R2=CH2, R4=H,
R3=R5=R6=CH3, R7=R8=OAng
Kadsura sp. (s) Liu & Ma, 1988b
70
schisantherin I
R1=H, R2=R3=R4=R5=R6=CH3,
R7=OBz, R8=OAc
Kadsura sp. (s)
合蕊五味子S. propinqua (s)
Liu & Ma, 1988b
Xu et al., 2006
71
schisantherin J
R1+R2=CH2, R3=R4=R5=R6=CH3,
R7=OBz, R8=OIsobutyloyl
长梗南五味子K. longipedunculata (s)
Liu & Pan, 1991
72
kadsurarin
R1+R2=CH2, R3=H,
R4=R5=R6=CH3,
R7=OAng, R8=OAc
日本南五味子K. japonica (s)
K. matsudai Hayata (s)
Kadsura sp. (s)
异形南五味子K. heteroclita (s)
Chen et al., 1973
Wu et al., 2003
Liu & Ma, 1988b
Wang et al., 2006a
73
propinquanin A
R1=H, R2=R3=R4=R5=R6=CH3,
R7=OAng, R8=OCap
合蕊五味子S. propinqua (s) Xu et al., 2006
74
propinquanin B
R1=R4=H, R2=R3=R5=R6=CH3,
R7=OBz, R8=OCap
合蕊五味子S. propinqua (s)
Xu et al., 2006
75
propinquanin C
R1+R2=CH2, R3=H,
R4=R5=R6=CH3,
R7=OAng, R8=OCap
合蕊五味子S. propinqua (s)
Xu et al., 2006
76
heteroclitalignan A
R1+R2=CH2, R3=H,
R4=R5=R6=CH3, R7=OAc, R8=OBz
异形南五味子K. heteroclita (s)
Wang et al., 2006a
77
heteroclitalignan B
R1+R2=CH2, R3=R4=R5=R6=CH3,
R7=OAng, R8=OProp
异形南五味子K. heteroclita (s)
Wang et al., 2006a
78
heteroclitalignan D
R1+R2=CH2, R3=OH,
R4=R5=R6=CH3, R7=OAc, R8=OBz
异形南五味子K. heteroclita (s)
Wang et al., 2006a
79
schizanrin I
R1+R2=CH2, R3=H,
R4=R5=R6=CH3, R7=OBz, R8=OBz
日本南五味子K. japonica (s)
Kuo et al., 2005b
80
schizanrin J
R1+R2=CH2, R3=H, R8=OAng
R4=R5=R6=CH3, R7=OTig
日本南五味子K. japonica (s)
Kuo et al., 2005b
81
schizanrin K
R1+R2=CH2, R3=R4=R5=R6=CH3,
R7=OTig, R8=Oxo
日本南五味子K. japonica (s)
Kuo et al., 2005b
82
schizanrin F
R1+R2=CH2, R3=R4=R5=R6=CH3,
R7=OBz, R8=OAc
K. matsudai (s) Wu et al., 2003
83
schizanrin G
R1+R2=CH2, R3=H, R8=OAc
R4=R5=R6=CH3, R7=OAng
K. matsudai (s) Wu et al., 2003
84
schizanrin H
R1=R2=R3=R4=R5=R6=CH3,
R7=OBz, R8=OAc
K. matsudai (s) Wu et al., 2003
85
renchangianin A
R1=R2=R5=R6=CH3, R3=R4=H,
R7=OBz, R8=OAc
仁昌南五味子K. renchangiana (s)
Chen et al., 2004a
86
renchangianin B
R1=R2=R5=R6=CH3, R3=R4=H,
R7=OBz, R8=OAng
仁昌南五味子K. renchangiana (s)
Chen et al., 2004a
87 renchangianin D
R1=R2=R5=R6=CH3, R3=R4=H,
R7=OBz, R8=OAng ,
7 (spirocyclic epoxy)
仁昌南五味子K. renchangiana (s) Chen et al., 2004a
88 deangeloylgomisin B R1+R2= CH2, R3=R4=R5=R6=CH3,
R7=H, R8=H
五味子 S. chinensis (f) Ikeya et al., 1979a
89
benzoylgomisin P
R1+R2=CH2, R3=R4=R5=R6=CH3,
R7=OBz, R8=H
华中五味子S. sphenanthera (f) Ikeya et al., 1990
90
tigloylgomisin P
R1+R2=CH2, R3=R4=R5=R6=CH3,
R7=OTig, R8=H
五味子S. chinensis (f)
合蕊五味子S. propinqua (s)
红花五味子S. rubriflora (s)
Ikeya et al., 1978a
Chen et al., 2001c
Chen et al., 2006
91
angeloylgomisin P
R1+R2=CH2, R3=R4=R5=R6=CH3,
R7=OAng, R8=H
五味子S. chinensis (f)
华中五味子S. sphenanthera (f)
红花五味子S. rubriflora (s)
Ikeya et al., 1980b
Ikeya et al., 1990
Chen et al., 2006
92
schizanrin A
R1+R2=CH2, R3=R7=H,
R4=R5=R6=CH3, R8=Cin
阿里山五味子S. arisanensis (s)
Kuo et al., 1999
许利嘉等: 五味子科药用植物亲缘学初探
699
表1 (续) Table 1 (continued)
序号
No.
化合物名称
Compound
结构1)
Structure1)
来源植物2)
Plant source2)
文献
Reference
93
schizanrin B
R1+R2=CH2, R3=R7=H,
R4=R5=R6=CH3, R8=Oiso-valeroyl
K. matsudai (s) Kuo et al., 2001
94
schizanrin C
R1+R2=CH2, R3=R7=H,
R4=R5=R6=CH3, R8=OCap
K. matsudai (s) Kuo et al., 2001
95
schizanrin D
R1+R2=CH2, R3=R7=H,
R4=R5=R6=CH3, R8=Oac
K. matsudai (s) Kuo et al., 2001
96
schizanrin E
R1+R2=CH2, R3=R7=H,
R4=R5=R6=CH3, R8=OBz
K. matsudai (s) Kuo et al., 2001
97
(±)-kadsutherin
R1=R2=R4=R5=R6=CH3,
R3=Ang, R7=R8=H
黑老虎K. coccinea (s)
Li et al., 1985
98 (+)-deoxyschizandrin
(schisandrin A,
wuweizisu A)
R1=R2=R3=R4=R5=R6=CH3,
R7=R8=H
五味子S. chinensis (f, s)
华中五味子S. sphenanthera (f, s)
合蕊五味子S. propinqua (s)
红花五味子S. rubriflora (s)
Chen et al., 1976
Liu et al., 1978b
Zhao et al., 1999
Jiang et al., 2005
Chen et al., 2006
99
(+)-γ-schisandrin
(schisandrin B,
wuweizisu B)
R1+R2=CH2, R3=R4=R5=R6=CH3,
R7=R8=H
五味子S. chinensis (f, s)
华中五味子S. sphenanthera (f, s)
Chen et al., 1976
Ikeya et al., 1979a
100
(+)-gomisin K2
R1=R7=R8=H,
R2=R3=R4=R5=R6=CH3,
五味子S. chinensis (f) Ikeya et al., 1980a
101
(+)-gomisin K3
R1=R2=R4=R5=R6=CH3,
R3=R7=R8=H
五味子S. chinensis (f)
华中五味子S. sphenanthera (f)
阿里山五味子S. arisanensis (s)
小花五味子S. micrantha (s)
Ikeya et al., 1980a
Ikeya et al., 1990
Yue et al., 1994
Wu et al., 2003
Li et al., 2005a
102
schisanhenol
R1=R2=R3=R5=R6=CH3,
R4=R7=R8=H
翼梗五味子S. henryi (f)
五味子S. chinensis (f)
红花五味子S. rubriflora (f, s)
中间五味子S. propinqua var. intermedia A. C. Smith (s)
Liu et al., 1978b
Chen et al., 1982
He et al., 1997
Li et al., 1996
103
schisanhenol acetate
R1=R2=R4=R5=R6=CH3,
R3=Ac, R7=R8=H
红花五味子S. rubriflora (f, s)
五味子S. chinensis (f)
Wang & Chen, 1985
Ikeya et al., 1980
104
(±)-gomisin M1
R1=R2=R4=CH3, R5+R6=CH2,
R3=R7=R8=H
五味子S. chinensis (f)
长梗南五味子K. longipedunculata (s)
红花五味子S. rubriflora (f, s)
Ikeya et al., 1982c
Tan et al., 1984
Chen et al., 2006
105
r(+)-angeloylgomisin
M1
R1=R2=R4=CH3, R5+R6=CH2,
R3=Ang, R7=R8=H
长梗南五味子K. longipedunculata (s) Tan et al., 1984
106
(+)gomisin M2
R1=R2=R3=CH3, R5+R6=CH2,
R4=R7=R8=H
五味子S. chinensis (f)
长梗南五味子K. longipedunculata (s)
红花五味子S. rubriflora (f, s)
Ikeya et al., 1982c
Li et al., 1985
Chen et al., 2006
107
kadsuranin
R1=R2=R3=R4=CH3,
R5+R6=CH2, R7=R8=H
长梗南五味子K. longipedunculata (s) Tan et al., 1984
108
schisantherin O
R1+R2=CH2, R3=R5=R6=CH3,
R4=R7=H, R8=OAc
黑老虎K. coccinea (s) Liu & Li, 1993
109
gomisin A
(schisandrol B)
R1+R2=CH2, R3=R4=R5=R6=CH3,
R7=OH, R8=H
五味子S. chinensis (f, s)
异形南五味子K. heteroclita (s)
凤庆南五味子K. interior (s)
长梗南五味子K. longipedunculata (s)
Ikeya et al., 1979c
Chen et al., 1976
Chen et al., 1997
Chen et al., 2002a
Li & Chen, 1986
110
schisandrin
(schisandrol A )
R1=R2=R3=R4=R5=R6=CH3,
R7=OH, R8=H
五味子S. chinensis (f)
长梗南五味子K. longipedunculata (s)
红花五味子S. rubriflora (f)
Ikeya et al., 1979c
Li & Chen, 1986
Chen et al., 2006
111
gomisin H
R1=R2=R4=R5=R6=CH3,
R7=OH, R3=R8=H
五味子S. chinensis (f)
黑老虎K. coccinea (s)
Ikeya et al., 1979d
Li et al., 1985
112
angeloylgomisin H R1=R2=R4=R5=R6=CH3,
R3=Ang, R7=OH, R8=H
五味子S. chinensis (f)
长梗南五味子K. longipedunculata (s)
Ikeya et al., 1978c
Li & Chen, 1986
113
tigloylgomisin H
R1=R2=R4=R5=R6=CH3,
R3=Tig, R7=OH, R8=H
五味子S. chinensis (f) Ikeya et al., 1978c
114
benzoylgomisin H
R1=R 2=R4=R5=R6=CH3,
R3=Tig, R7=OH, R8=H
五味子S. chinensis (f) Ikeya et al., 1978c
115
gomisin T
R2=R3=R4=R5=R6=CH3,
R1=R8=H, R7=OH
五味子S. chinensis (f) Ikeya et al., 1988a
植物分类学报 Journal of Systematics and Evolution 2008 46卷5期 700
表1 (续) Table 1 (continued)
序号
No.
化合物名称
Compound
结构1)
Structure1)
来源植物2)
Plant source2)
文献
Reference
116
isoschizandrin
R1=R2=R3=R4=R5=R6=CH3,
R7=OH, R8=H
五味子S. chinensis (f) Ikeya et al., 1988b
117
schisanlignone A
R1=R2=R3=R4=R5=R6=CH3,
R7=H, R8=Oxo
Kadsura sp. (s) Liu & Zhou, 1991
118
schisanlignone B
R2=R3=R4=R5=R6=CH3,
R1=R7=H, R8=Oxo
Kadsura sp. (s) Liu & Zhou, 1991
119
schisanlignone C
R1=R2=R3=R4=CH3, R5+R6=CH2,
R7=H, R8=Oxo
绿叶五味子S. viridis A. C. Smith (s) Luo et al., 1992a
120
schisanlignone D
R1+R2=R5+R6=CH2, R3=R4=CH3,
R7=H, R8=Oxo
绿叶五味子S. viridis (s) Luo et al., 1992a
121
schisanlignone E
R1+R2=CH2, R4=R5=R6=CH3,
R3=Bz, R8=Oxo
绿叶五味子S. viridis (s) Luo et al., 1992a
122
schisanhenol B
R1+R2=CH2, R3=R5=R6=CH3,
R4=R7=R8=H
红花五味子S. rubriflora (f)
Wang et al., 1985
123
longipedunin C
R1+R2=CH2, R3=R5=R6=CH3,
R4=R7=H, R8=Bz
长梗南五味子K. longipedunculata (s) Sun et al., 2006
124 micrantherin A R1=R2=R3=R5=R6=CH3,
R4=R7=R8=H (C8-OAng)
小花五味子S. micrantha (s) Li et al., 2005a
125
gomisin O
R1+R2=CH2, R3=R4=R5=R6=CH3,
R7=OH, R8=H
五味子S. chinensis (f)
合蕊五味子S. propinqua (s)
红花五味子S. rubriflora (f)
Ikeya et al., 1979a
Chen et al., 2001c
Chen et al., 2006
126
angeloylgomisin O
R1+R2=CH2, R3=R4=R5=R6=CH3,
R7=OAng, R8=H
五味子S. chinensis (f)
合蕊五味子S. propinqua (s)
Ikeya et al., 1982a
Chen et al., 2001c
127
angeloylisogomisin
O
R1=R2=R3=R4=CH3, R5+R6=CH2,
R7=OAng, R8=H
五味子S. chinensis (f)
合蕊五味子S. propinqua (s)
Ikeya et al., 1982a
Chen et al., 2001c
128
6-O- benzoylgomisin
O
R1+R2=CH2, R3=R4=R5=R6=CH3,
R7=OBz, R8=H
五味子S. chinensis (f)
合蕊五味子S. propinqua (s)
Chen et al., 1994
Chen et al., 2001c
129
benzoylisogomisin O
R1=R2=R3=R4=CH3, R5+R6=CH2,
R7=OBz, R8=H
五味子S. chinensis (f)
合蕊五味子S. propinqua (s)
Ikeya et al., 1982a
Chen et al., 2001c
130
gomisin R
R1+R2=R5+R6=CH2, R3=R4=CH3,
R7=OH, R8=H
五味子S. chinensis (f)
Ikeya et al., 1982b
131
schisantherin Q
R1+R2=R5+R6=CH2, R3=R4=CH3,
R7=Oxo, R8=OH
黑老虎K. coccinea (s)
Liu & Li, 1995a
132
angeloylgomisin R
R1+R2=R5+R6=CH2, R3=R4=CH3,
R7=OAng, R8=H
长梗南五味子K. longipedunculata (s)
凤庆南五味子K. interior (s)
合蕊五味子S. propinqua (s)
Tan et al., 1984
Chen et al., 1997
Chen et al., 2001a
133
interiotherin A
R1+R2=R5+R6=CH2, R3=R4=CH3,
R7=OBz, R8=H
凤庆南五味子K. interior (s) Chen et al., 1996
134
rubschisantherin
R1+R2=CH2, R3=R4=R5=R6=CH3,
R7=OAc, R8=H
红花五味子S. rubriflora (f) Wang & Chen, 1985
135
schisanlignaol D
R1+R2=R5+R6=CH2, R3=R4=CH3,
R7=H, R8=OH
绿叶五味子S. viridis (s) Luo et al., 1992a
136
schisantherin K
R1=R2=R3=R5=R6=CH3,
R4=Tig, R7=OAc, R8=OH
绿叶五味子S. viridis (s) Luo et al., 1992b
137
yunnankadsurin A
R1+R2=CH2, R3=R4=R5=CH3,
R6=OH, R7=Oxo, R8=H
Kadsura sp. (s) Jia et al., 2005
138
yunnankadsurin B
R1+R2=CH2, R3=R4=R5=R6=CH3,
R7=H, R8=OH
Kadsura sp. (s) Jia et al., 2005
139
schizanrin M
R1+R2=CH2, R3=R4=R5=CH3,
R6=R8=H, R7=Oxo
日本南五味子K. japonica (s) Kuo et al., 2005b
140
schizanrin N
R1=R2=R3=CH3, R4=R8=H,
R5+R6=CH3, R7=Oxo
日本南五味子K. japonica (s) Kuo et al., 2005b
141
kadsulignan L
R1+R2=CH2, R3=R4=R5=R6=CH3
黑老虎K. coccinea (s)
狭叶南五味子K. angustifolia (s)
合蕊五味子S. propinqua (s)
Liu & Li, 1995b
Chen et al., 1998a
Chen et al., 2001c
142
kadsulignan M
R1+R2=CH2, R3=R4=R5=CH3,
R6=H
黑老虎K. coccinea (s) Liu & Li, 1995b
143
kadsulignan N
R1=R2=R3=R4=R5=R6=CH3,
黑老虎K. coccinea (s)
狭叶南五味子K. angustifolia (s)
Liu & Li, 1995b
Chen et al., 1998a
144 neokadsuranin R1=R2=R3=R4=CH3, R5+R6= CH2 黑老虎K. coccinea (s)
凤庆南五味子K. interior (s)
Li et al., 1988
Chen et al., 2002a
许利嘉等: 五味子科药用植物亲缘学初探
701
表1 (续) Table 1 (continued)
序号
No.
化合物名称
Compound
结构1)
Structure1)
来源植物2)
Plant source2)
文献
Reference
145 gomisin D R1=CH3, R2=OH 五味子S. chinensis (f) Ikeya et al., 1976
146 gomisin E R1=H, R2= CH3 五味子S. chinensis (f) Ikeya et al., 1979a
1)
Ac C
O
CH3
Bz C
O
C
O
Cin C
H
C
H
Cap C
O
CH2CH2CH2CH2CH3 butanoyl C
O
CH2CH2CH3 Prop C
O
CH2CH3
Ang C
O
C C
H3C H
CH3
Tig C
O
C C
H3C CH3
H
iso-Valeroyl C
O
C
H
CH3
CH2CH3
2) f, 果实; s, 茎。f, fruits; s, stems.
图2 五味子科植物中螺苯骈呋喃型联苯环辛烯类木脂素成分的结构
Fig. 2. Structures of spirobenzofuranoid dibenzocyclooctadienes from Schisandraceae.
表2 五味子科植物中螺苯骈呋喃型联苯环辛烯类木脂素
Table 2 Spirobenzofuranoid dibenzocyclooctadienes from Schisandraceae
序号
No.
化合物名称
Compound
结构1)
Structure1)
来源植物2)
Plant source2)
文献
Reference
147
heteroclitin D
R1=R4=H, R2=OAng, R3=CH3
异形南五味子Kadsura heteroclita (s)
红花五味子Schisandra rubriflora (s)
凤庆南五味子K. interior (s)
Chen et al., 1992
Li et al., 2004a
Chen et al., 2002a
148 heteroclitin E R1=OH, R2=OAng, R3=CH3,
R4=H
异形南五味子K. heteroclita (s) Chen et al., 1992
149
isovaleroyloxokadsurane
R1=R4=H, R2=Oisovaleroyl,
R3=CH3
长梗南五味子K. longipedunculata (s)
黑老虎K. coccinea (s)
Li et al., 1991
Li & Xue, 1990
150 acetoxyloxokadsurane R1=R4=H, R2=OAc, R3=CH3 黑老虎K. coccinea (s) Li & Xue, 1990
151 benzoyloxokadsurane R1=R4=H, R2=OBz, R3=CH3 黑老虎K. coccinea (s) Li & Xue, 1990
植物分类学报 Journal of Systematics and Evolution 2008 46卷5期 702
表2 (续) Table 2 (continued)
序号
No.
化合物名称
Compound
结构1)
Structure1)
来源植物2)
Plant source2)
文献
Reference
152 propoxyloxokadsurane R1=R4=H, R2=OProp, R3=CH3 黑老虎K. coccinea (s) Li & Xue, 1990
153 kadsulignan H R1=R4=H, R2=Obutanoyl,
R3=CH3
Kadsura sp. (s) Liu et al., 1992
154 kadsulignan I R1=R4=H, R2=OProp, R3=CH3 Kadsura sp. (s) Liu et al., 1992
155 kadsulignan J R1=R4=H, R2=Oiso-Valeroyl,
R3=CH3
Kadsura sp. (s) Liu et al., 1992
156 heterociltin E R1=OH, R2=OAng, R3=CH3,
R4=H
异形南五味子K. heteroclita (s) Chen et al., 1992
157 isovaleroyloxokad-
suranol
R1=OH, R2= OIsovaleroyl,
R3=CH3, R4=H
黑老虎K. coccinea (s) Li & Xue, 1990
158 heteroclitin I R1=OBz, R2=OAng, R3=CH3,
R4=H
异形南五味子K. heteroclita (s) Xu et al., 2007
159 heteroclitin J R1=OBz, R2=OAc, R3=CH3,
R4=H
异形南五味子K. heteroclita (s) Xu et al., 2007
160 heteroclitin K R1=OBz, R2=OBz, R3=CH3,
R4=H
异形南五味子K. heteroclita (s) Xu et al., 2007
161 heteroclitin L R1=OAng, R2=OBz, R3=CH3,
R4=H
异形南五味子K. heteroclita (s) Xu et al., 2007
162 kadsulignan C R1=OAc, R2=OBz, R3=OH,
R4=CH3
长梗南五味子K. longipedunculata (s) Liu et al., 1991
163 kadsulignan D R1=R2=OAng, R3=OH, R4=CH3 长梗南五味子K. longipedunculata (s) Liu et al., 1991
164
interiorin
R1=R4=H, R2=OAng, R3=CH3
凤庆南五味子K. interior (s)
异形南五味子K. heteroclita (s)
红花五味子S. rubriflora (s)
Shide et al., 1988
Chen et al., 1992
Li et al., 2004a
165
interiorin B
R1=R4=H, R2=OTig, R3=CH3
凤庆南五味子K. interior (s)
红花五味子S. rubriflora (s)
Ding & Luo, 1990
Li et al., 2004
166 interiorin C R1=R4=H, R2=OAc, R3=CH3 凤庆南五味子K. interior (s) Ding & Luo, 1990
167 interiorin D R1=R4=H, R2=OBz, R3=CH3 凤庆南五味子K. interior (s) Ding & Luo, 1990
168 heteroclitalignan C R1=OAng, R2=OProp,
R3=OH, R4=CH3
异形南五味子K. heteroclita (s) Wang et al., 2006a
169 kadsulignan E R1=OAc, R2=OBz, R3=OH,
R4=CH3
长梗南五味子K. longipedunculata (s)
异形南五味子K. heteroclita (s)
Liu & Huang, 1992
Wang et al., 2006a
170 kadsulignan F R1=OAng, R2=OAc, R3=OH,
R4=CH3
长梗南五味子K. longipedunculata (s) Liu & Huang, 1992
171 kadsulignan G R1=R2=OAng, R3=OH, R4=CH3 长梗南五味子K. longipedunculata (s) Liu & Huang, 1992
172 interiotherin D 凤庆南五味子K. interior (s) Chen et al., 2002a
173 kadsulignan A R=H 黑老虎K. coccinea (s) Liu et al., 1989
174 kadsulignan B R=OAc 黑老虎K. coccinea (s) Liu et al., 1989
175 kadsulignan K Kadsura sp. (s) Liu et al., 1992
176 schiarisanrin A R=Oiso-valeroyl 阿里山五味子S. arisanensis (s) Kuo et al., 1997
177 schiarisanrin B R=OAc 阿里山五味子S. arisanensis (s) Kuo et al., 1997
178 schiarisanrin C R=OBz 阿里山五味子S. arisanensis (s) Kuo et al., 1997
179 schiarisanrin D R=OCin 阿里山五味子S. arisanensis (s) Kuo et al., 1997
180 schiarisanrin E R=OAng 阿里山五味子S. arisanensis (s) Wu et al., 2003
181 heteroclitin F R=OAng 异形南五味子K. heteroclita (s)
凤庆南五味子K. interior (s)
Yang et al., 1992
Chen et al., 2002a
182 taiwanschirin A R=Oiso-valeroyl 阿里山五味子S. arisanensis (s) Kuo et al., 1999
183 taiwanschirin B R=OAc 阿里山五味子S. arisanensis (s) Kuo et al., 1999
184 taiwanschirin C R=OBz 阿里山五味子S. arisanensis (s) Kuo et al., 1999
185 taiwanschirin D R=OCap K. matsudai (s) Li et al., 2000
186 taiwankadsurin A 1-OH, R1=Bz, R2=Ac 菲律宾五味子K. philippinensis (s) Shen et al., 2005b
187 taiwankadsurin B 1-OH, R1=Bz, R2=Ac 菲律宾五味子K. philippinensis (s) Shen et al., 2005b
188 taiwankadsurin C R1=Ac, R2=Bz 菲律宾五味子K. philippinensis (s) Shen et al., 2005b
1)、2) 注释同表1。1) , 2) are the same as in Table 1.
许利嘉等: 五味子科药用植物亲缘学初探
703
图3 五味子科植物中芳基四氢萘类木脂素成分的结构
Fig. 3. Structures of Aryltetralins from Schisandraceae.
表3 五味子科植物中芳基四氢萘类木脂素
Table 3 Aryltetralins from Schisandraceae
序号
No.
化合物名称
Compound
结构
Structure
来源植物1)
Plant source1)
文献
Reference
189
schisandrone
R1=H, R2=R3=R4=CH3 翼梗五味子Schisandra henryi (f)
华中五味子S. sphenanthera (f)
Liu et al., 1988b
Li & Xue, 1985b
190 enshicine R1+R2=CH2, R3=H, R4=CH3 翼梗五味子S. henryi (f) Liu et al., 1984b
191 wulignan A1 R1=R3=H, R2=R4=CH3 翼梗五味子S. henryi (f) Liu et al., 1988b
192
epienshicine
R1+R2=CH2 , R3=H, R4=CH3
翼梗五味子S. henryi (f)
铁箍散S. propinqua (Wall.) Baill. var. sinensis
Oliv. (f)
Liu et al., 1988b
Liu et al., 1988a
193 epienshicine methyl ether R1+R 2=CH2 , R3=R4=CH3 翼梗五味子S. henryi (f) Tao et al., 1991
194 epischisandrone R1=H, R2=R3=R4=CH3 翼梗五味子S. henryi (f) Liu et al., 1988b
195 epiwulignan A1 R1=R3= H, R2=R4=CH3 翼梗五味子S. henryi (f) Liu et al., 1988b
196 wulignan A2 R1=R4=CH3, R2=R3=H 翼梗五味子S. henryi (f) Liu et al., 1988b
197 schizandriside S. nigra Maxim. (s) Takahashi & Takani, 1975
1) f, 果实; s, 茎。f, fruits; s, stems.
表4 五味子科植物中二芳基丁烷类木脂素
Table 4 Diarylbutanes from Schisandraceae
序号
No.
化合物名称
Compound
结构
Structure
来源植物1)
Plant source1)
文献
Reference
198
pregomisin
R1=R4=OH, R2=R3=R5=R6=OCH3 五味子Schisandra chinensis (f)
红花五味子S. rubriflora (s)
中间五味子S. propinqua var. intermedia (s)
Ikeya et al., 1978b
Wang & Chen, 1985
Li et al., 1996
199 preschisanthrin R1=R3=R4=R6=OCH3, R2=R5=OH 中间五味子S. propinqua var. intermedia (s) Li et al., 1996
200
(+)-anwulignan
R1+R2=OCH2O, R3=R4=H, R5=OH,
R6=OCH3
长梗南五味子K. longipedunculata (s)
华中五味子S. sphenanthera (f, s)
Liu & Huang, 1988
Jiang et al., 2005
201
dl-anwulignan
R1=OCH3, R2=OH, R3=R4=H,
R5+R6=OCH2O
华中五味子S. sphenanthera (f) Liu & Huang, 1984a
202
mesodihy-
droguaiaretic acid
R1=R6=OCH3, R3=R4=H,
R2=R5=OH
五味子S. chinensis (f)
长梗南五味子Kadsura longipedunculata (s)
红花五味子S. rubriflora (f)
狭叶南五味子K. angustifolia (s)
异形南五味子K. heteroclita (s)
Chen et al., 2005a
Liu & Huang, 1991
Wang & Chen, 1985
Chen et al., 1998a
Wang et al., 2006a
203
isoanwulignan
R1=H, R2=OH, R3=OCH3, R4=H,
R5+R6=OCH2O
绿叶五味子S. viridis (s)
翼梗五味子S. henryi (f)
Luo et al., 1992b
Chen et al., 2005b
204 nordihydroguaiaretic
acid
R1=R2=R5=R6=OH, R3=R4=H 五味子S. chinensis (f) Sakurai et al., 1992
205
sphenanlignan
R1+R2=OCH2O, R3=H,
R4=R5=OCH3, R6=OH
华中五味子S. sphenanthera (f) Jiang et al., 2005
206 lengfantuanjing I R1=R4=H, R2=OH, R3=OCH3,
R5+R6=OCH2O
黑老虎K. coccinea (s) Liu & Wang, 1989
207 lignandiol 红花五味子S. rubriflora Wang et al., 1993
1) f, 果实; s, 茎。f, fruits; s, stems.
植物分类学报 Journal of Systematics and Evolution 2008 46卷5期 704
图4 五味子科植物中二芳基丁烷类木脂素成分的结构
Fig. 4. Structures of diarylbutanes from Schisandraceae.
图5 五味子科植物中四氢呋喃类木脂素成分的结构
Fig. 5. Structures of tetrahydrofurans from Schisandraceae.
表5 五味子科植物中四氢呋喃类木脂素
Table 5 Tetrahydrofurans from Schisandraceae
序号
No.
化合物名称
Compound
结构
Structure
来源植物1)
Plant source1)
文献
Reference
208 chicanine R1+R2=CH2, R3=R4=R6=H, R5=CH3 华中五味子Schisandra sphenanthera (s) Liu et al., 1981
209
d-epigalbacin
R1+R2=R4+R5=CH2, R3=R6=H
华中五味子S. sphenanthera (s)
异形南五味子Kadsura heteroclita (s)
Huang et al., 1982a
Wang et al., 2006a
210 ganschisandrine R1=R2=R4=R5=CH3, R3=R6=H 华中五味子S. sphenanthera (s) Yue et al., 1989
211 veraguensin R1=R2=R4=R5=CH3, R3=R6=H Kadsura sp. (s) Liu & Huang, 1988
212 henricine R1=R2=CH3, R3=OCH3, R4+R5=CH2, R6=H 翼梗五味子S. henryi (s) Li & Xue, 1986a
213 enshizhisu R1+R2=CH2, R3=R4=H, R5=CH3, R6=OH 翼梗五味子S. henryi (s) Huang et al., 1982b
1) f, 果实; s, 茎。f, fruits; s, stems.
图6 五味子科植物中各类木脂素类型之间的演化关系(徐任生, 2004; Shen et al., 2005b)
Fig. 6. Proposed biogenetic relationships between different lignan types in Schisandraceae (Xu, 2004; Shen et al., 2005b).
许利嘉等: 五味子科药用植物亲缘学初探
705
表6 木脂素在五味子科药用植物中的分布
Table 6 Distribution of lignans in the family Schisandraceae
木脂素 Lignans 种
Species I
联苯环辛烯类
Dibenzocycloocta-
dienes
II
螺苯骈呋喃型联苯环辛烯类
Spirobenzofuranoid dibenzo-
cyclooctadienes
III
芳基四氢萘类
Aryltetralins
IV
二芳基丁烷类
Diarylbutanes
V
四氢呋喃类
Tetrahydrofurans
五味子Schisandra chinensis 42 3
华中五味子S. sphenanthera 16 1 3 3
红花五味子S. rubriflora 25 3 3
翼梗五味子S. henryi 4 8 1 2
绿叶五味子S. viridis 5 1
合蕊五味子S. propinqua 23 2
阿里山五味子S. arisanensis 4 8
S. nigra 1
球蕊五味子S. sphaerandra 1
小花五味子S. micrantha 3
黑老虎Kadsura coccinea 16 7 1
凤庆南五味子K. interior 9 7
异形南五味子K. heteroclita 7 11 1 1
长梗南五味子K. longipedunculata 18 6 2
日本南五味子K. japonica 14
K. matsudai 8 1
狭叶南五味子K. angustifolia 7 1
仁昌南五味子K. renchangiana 4
菲律宾五味子K. philippinensis 4 3
只出现在C-14或C-1位, 而亚甲二氧基则在C-12(13)
或C-2(3)。八元环的取代主要发生在C-6, 9位的成酯
取代(酯基多位当归酸酯、苯甲酸酯、乙酸酯等), 羟
基多在C-6, 7位取代。化合物134–138是联苯环辛烯
类中较特殊的一类, 特征为在八元环上跨氧桥, 这
一类化合物多从南五味子科中分离得到, 仅有一个
从合蕊五味子中得到。从总体上来看, 联苯环辛烯
类木脂素在五味子属和南五味子属植物的果实和
藤茎中较平均分布, 可以被认为是五味子科植物的
特征性化学成分; 芳基四氢萘类和四氢呋喃类木脂
素绝大多数存在于五味子属植物的藤茎中; 二芳基
丁烷类较多地存在于五味子属, 而螺苯骈呋喃型联
苯环辛烯类木脂素则多存在于南五味子属植物的
藤茎中, 可以看作是南五味子属植物的特有化学成
分, 这类成分具有重要的分类学意义。值得提出的
是, 五味子科中分离得到的42个螺苯骈呋喃型联苯
环辛烯类木脂素中, 除11个化合物来自五味子属红
花五味子、阿里山五味子, 其他均从南五味子属分
离得到, 由此可以推测红花五味子和阿里山五味子
及其近缘种是五味子属与南五味子属之间的过渡
类群, 这一点还需要其他证据来佐证。上述五味子
科植物木脂素的分布规律提示, 在演化程度上, 五
味子属较南五味子属更原始, 因而作者支持Smith
(1947)的观点, 将五味子属放在南五味子属之前。
2.2 五味子植物中的三萜及其分类学意义
五味子科植物中分离鉴定出的另一大类成分
为三萜, 分离得到100余种。三萜类化合物的结构复
杂多样, 新颖独特, 根据A环是否开环以及三萜各
环的碳原子数将骨架分为5种类型 : I. 6/6/6/5或
6/6/5/6型环菠萝蜜烷三萜(A环闭环)(cycloartanone
triterpenes, A-ring close; 图7; 表7); II. 6/6/5或者
6/5/6型环菠萝蜜烷型三萜(A环开环)(cycloartanone
triterpenes, A-ring open; 图8; 表8); III. 7/6/6/5或者
7/7/6/5型三萜(7/6/6/5 or 7/7/6/5 type triterpenes; 图
9; 表9); IV. 7/7/5/6型三萜内酯(7/7/5/6 type triter-
pene lactones; 图10; 表10); V. 类三萜内酯(nor-
triterpene lactones; 图11; 表11)。
从生源途径上来说, 羊毛甾烷型四环三萜是其
他几类三萜的生物合成前体, 取代基团多为当归酸
酯侧链或六元内酯环, 一些化合物则在A环3, 4开
环而形成二酸或内酯酸。7/7/5/6型三萜内酯应该是
从7/7/6/5型三萜内酯衍化而来的, 属较进化的化学
成分; 近期研究发现一类结构新颖的类三萜内酯,
成环复杂, 且结构高度氧化, 理应属于更进化的化
学成分, 此类类三萜内酯目前只出现在五味子科植
物中, 具有较重要的分类学意义(图12; 表12)。
植物分类学报 Journal of Systematics and Evolution 2008 46卷5期 706
图7 五味子科植物中环菠萝蜜烷型三萜(A环闭环)的结构
Fig. 7. Structures of cycloartanone triterpenes (A-ring close) from Schisandraceae.
图8 五味子科植物中菠萝蜜烷型三萜的结构
Fig. 8. Structures of cycloartanone triterpenes (A-ring open) from Schisandraceae.
三萜类成分在五味子科植物中的分布同样显
示出了一定的规律性: 绝大多数三萜类成分都从五
味子科药用植物的藤茎中分离得到, 而在果实中分
布很少, 比如只在华中五味子的果实中发现了两个
三萜化合物。羊毛甾烷型四环三萜在五味子属和南
五味子属均有分布。而7/6/6/5, 7/7/6/5型两大类三萜
是四环三萜中较6/6/6/5三萜更进化的成分, 此两类
内酯大多数存在于南五味子属。目前为止, 有7个
7/7/6/5型三萜内酯从合蕊五味子和翼梗五味子S.
henryi Clarke中分离得到, 其他都从南五味子属植
物中分离得到, 这点提示我们或许合蕊五味子和翼
梗五味子及其变种是由北五味子属向南五味子属
进化的过渡类群, 但是这需要更多的证据来支持。
显然, 7/7/5/6型三萜内酯从7/7/6/5型三萜内酯进化
而来, 属于更进化的化学状态, 目前这类成分只在
南五味子植物中发现, 从上述两点来看, 南五味子
属是较五味子属更为进化的类群; 然而, 近年来的
研究发现, 从五味子属的小花五味子和狭叶五味子
中分离得到了20个类三萜内酯, 这些类三萜内酯成
环复杂, 且高度氧化, 属于更为进化的化学状态,
此研究结果向我们提示五味子属的小花五味子和
狭叶五味子也许是较为进化的两个种, 但这仅仅是
就目前的研究结果进行的推测, 更多的三萜类成分
有待于在五味子属植物中发现。虽然三萜类成分在
化学结构上的多样性和复杂性很难给出南五味子
属是五味子科中较五味子属更为进化的类群这样
的定论, 但是仍支持五味子属和南五味子属的亲缘
关系较近, 对于该科植物的化学分类同样具有重要
性。
3 传统疗效
在我国民间, 五味子属植物中作为药用的共有
14种4变种, 传统上, 本属很多植物以果实入药, 具
有滋补强壮、宁心安神、止咳化痰之功能, 如《中
华人民共和国药典》收载的五味子Schisandra
chinensis Baill.和华中五味子S. sphenanthera Rehd.
& Wils.的果实, 在民间五味子属其他种的果实多用
许利嘉等: 五味子科药用植物亲缘学初探
707
表7 五味子科植物中环菠萝蜜烷型三萜(A环闭环)
Table 7 Cycloartanone triterpenes (A-ring close) from Schisandraceae
序号
No.
化合物名称
Compound
结构1)
Structure1)
来源植物2)
Plant source2)
文献
Reference
1
schisandronic acid
3-oxo; 9,19-cyclo; 24(Z)
Schisandra nigra (s)
Schisandra sp. (s)
华中五味子S. sphenanthera (s)
中间五味子S. propinqua var. intermedia (s)
五味子S. chinensis (s)
Kadsura sp. (s)
小花五味子S. micrantha (s)
异形五味子Kadsura heteroclita (s)
合蕊五味子S. propinqua (s)
翼梗五味子S. henryi (s)
Takahashi & Takani, 1975
Liu & Huang, 1988a
Chen et al., 1987
Li et al., 1995
Liu et al., 1990
Liu & Huang, 1991
Li et al., 2003a
Chen et al., 2001d
Chen et al., 2003
Wang et al., 2006b
2 heteroclic acid 3-oxo; 9,19-cyclo; 24(Z)
22-OAc
异形五味子K. heteroclita (s) Wang et al., 2006b
3 schizandrolic acid 3-βOH; 9,19-cyclo; 24(Z) S. nigra (s) Takahashi et al., 1975
4
isoschizandrolic acid
3-αOH; 9,19-cyclo; 24(Z)
中间五味子S. propinqua var. intermedia (s)
Kadsura sp. (s)
Li et al., 1995
Liu & Huang, 1988
5 anwuweisonic acid 3-oxo, R1=CH3, R2=H 合蕊五味子S. propinqua (s) Liu et al., 1988a
6 epianwuweizic acid 3-βOH, 24(Z)-∆8 长梗南五味子K. longipedunculata (s)
狭叶南五味子K. angustifolia (s)
Liu et al., 1991
Chen et al., 2002b
7 anwuweizic acid 3-αOH, 24(Z)-∆8 华中五味子S. sphenanthera (f, s)
狭叶南五味子K. angustifolia (s)
Liu & Huang, 1984a
Chen et al., 2002b
8 coccinic acid 3-oxo, 24(Z)-∆9(11) 黑老虎K. coccinea (s)
滇藏五味子S. neglecta A. C. Smith (s)
Li & Xue, 1986b
Ma et al., 2002
9 iso-anwuweizic acid 3-αOH, 24(Z)-∆9(11) 异形南五味子K. heteroclita (s) Dai et al., 1990
10 (24Z)-3-oxo-12α-acetoxyl
anosta-8,24-dien-26-oic acid
3-oxo, 12-αOAc, 24(Z)-∆8 长梗南五味子K. longipedunculata (s)
小花五味子S. micrantha (s)
Li et al., 1989c
Li et al., 2003a
11 (24Z)-3-oxo-12α-hydroxyl
anosta-8,24-dien-26-oic acid
3-oxo, 12-αOH, 24(Z)-∆8 长梗南五味子K. longipedunculata (s) Li et al., 1989c
12 12β-acetoxycoccinic acid 3-oxo, 12-βOAc,
24(Z)-∆9(11)
异形南五味子 K. heteroclita (s) Li et al., 1989b
13 12β-hydroxycoccinic acid 3-oxo, 12-βOH, 24(Z)-∆9(11) 异形南五味子K. heteroclita (s) Li et al., 1989b
14 12α-acetoxycoccinic acid 3-oxo, 12-αOAc,
24(Z)-∆9(11)
异形南五味子K. heteroclita (s) Li et al., 1989b
15 12α-hydroxycoccinic acid 3-oxo, 12-αOH, 24(Z)-∆9(11) 异形南五味子K. heteroclita (s) Li et al., 1989b
16 schisanhenric acid 3-oxo, 22-OAc, 24(E)-∆9(11) 翼梗五味子S. henryi (s) Li et al., 1989b
17 ananosic acid A 中泰南五味子 K. ananosma (s) Chen et al., 2001e
18 ananosic acid B R1=H, R2=CH3COO– 中泰南五味子K. ananosma (s) Chen et al., 2004b
19 ananosic acid C R1=R2=O 中泰南五味子K. ananosma (s) Chen et al., 2004b
20
kadsulactone
3-oxo, 9,19-cyclo
长梗南五味子K. longipedunculata (s)
Kadsura sp. (s)
You et al., 1997
Ran et al., 1991
21 schisanlactone D 3-oxo, ∆9 (11) Schisandra sp. (f, s) Liu & Huang, 1984b
22 schisanol 3-βOH, ∆9 (11) 华中五味子S. sphenanthera (f, s) Yue et al., 1994
23 schisanterpene B 合蕊五味子S. propinqua (s) Xu et al., 2006
24 lancifodilactone H 狭叶五味子S. lancifolia A. C. Smith (s) Xiao et al., 2006b
25 neokadsuranic acid A 3-oxo; (24Z)-∆9(11), 13(18) 异形南五味子K. heteroclita (s) Kangouri et al., 1989
26 neokadsuranic acid B 3-oxo; (24Z)-∆8, 13(18) 长梗南五味子K. longipedunculata (s) Li et al., 1989c
27 neokadsuranic acid C 3-oxo; (24Z)-∆8, 13-βOH 长梗南五味子K. longipedunculata (s) Li et al., 1989c
28 ergosterol peroxide 滇藏五味子S. neglecta (s) Ma et al., 2002
1) Ac C
O
CH3
2) f, 果实; s, 茎。f, fruits; s, stems.
植物分类学报 Journal of Systematics and Evolution 2008 46卷5期 708
表8 五味子科植物中环菠萝蜜烷型三萜(A环裂环)
Table 8 Cycloartanone triterpenes (A-ring open) from Schisandraceae
序号
No.
化合物名称
Compound
结构1)
Structure1)
来源植物2)
Plant source2)
文献
Reference
29 manwuweizic acid (24Z)-∆8 合蕊五味子Schisandra propinqua (s)
异形南五味子Kadsura heteroclita (s)
Liu et al., 1988a
Chen et al., 2001d
30 kadsuric acid (24Z)-∆9(11) 翼梗五味子S. henryi (s)
黑老虎K. coccinea (s)
滇藏五味子S. neglecta (s)
小花五味子S. micrantha (s)
Chen et al., 2003
Li & Xue, 1986b
Ma et al., 2002
Li et al., 2003a
31 changnanic acid 9,19-cyclo, (24Z)-∆6 长梗南五味子K. longipedunculata (s)
异形南五味子K. heteroclita (s)
Liu & Huang, 1991
Wang et al., 2006b
32 nigranoic acid R1=R2=CH2, 9,19-cyclo, (24Z)- 球蕊五味子S. sphaerandra (s)
翼梗五味子S. henryi (s)
狭叶五味子S. lancifolia (s)
合蕊五味子S. propinqua (s)
异形南五味子K. heteroclita (s)
Sun et al., 1996
Chen et al., 2003
Xiao et al., 2006b
Chen et al., 2001d
Wang et al., 2006b
33 lancifoic acid A R1=OH, R2=CH3, 9,19-cyclo,
(24Z)
狭叶五味子S. lancifolia (s) Xiao et al., 2006b
34 heteroclitalactones A R1=OH, R2=OAc, 9,19-cyclo 异形南五味子K. heteroclita (s) Wang et al., 2006b
35 heteroclitalactones B R1= OCH3, R2=OAc, 9,19-cyclo 异形南五味子K. heteroclita (s) Wang et al., 2006b
36 heteroclitalactones C R1=EtO, R2=OAc, 9,19-cyclo 异形南五味子K. heteroclita (s) Wang et al., 2006b
37 heteroclitalactones F R1= OCH3, R2=H, 9,19-cyclo 异形南五味子K. heteroclita (s) Wang et al., 2006b
38 schisanlactone E R1=OH, R2=H, 9,19-cyclo 长梗南五味子K. longipedunculata (s)
异形南五味子K. heteroclita (s)
Liu & Huang, 1991
Wang et al., 2006b
39 schisanlactone F R1=OH, R2=H, 9,19-cyclo,∆8 长梗南五味子K. longipedunculata (s) Liu & Pan, 1991
40 seco-neokadsuranic acid A (24Z)-∆8, 13(18) 异形南五味子K. heteroclita (s) Li et al., 1989a
1) Ac C
O
CH3
2) f, 果实; s, 茎。f, fruits; s, stems.
图9 五味子科植物中7/6/6/5或者7/7/6/5三萜的结构
Fig. 9. Structures of 7/6/6/5 or 7/7/6/5 type triterpenes from Schisandraceae.
许利嘉等: 五味子科药用植物亲缘学初探
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表9 五味子科植物中7/6/6/5或者7/7/6/5三萜
Table 9 7/6/6/5 or 7/7/6/5 type triterpenes from Schisandraceae
序号
No.
化合物名称
Compound
结构1)
Structure1)
来源植物2)
Plant source2)
文献
Reference
41 kadsudilactone 9,19-cyclo Kadsura sp. Ran et al., 1991
42
schisanlactone B
9,19-cyclo, ∆1
Schisandra sp. (s)
翼梗五味子S. henryi (s)
合蕊五味子S. propinqua (s)
异形南五味子K. heteroclita (s)
Liu et al., 1983a
Chen et al., 2003
Chen et al., 2001b
Wang et al., 2006b
43 kadsulactone A 6-βOH, 9,19-cyclo, ∆1 K. lancilimba How. (s) Chen et al., 1999
44 kadsuphilactone B ∆1, 20-OH 菲律宾五味子K. philippinensis (s) Shen et al., 2005b
45 heteroclitalactones D 12-OAc, 20-H 异形南五味子K. heteroclita (s) Wang et al., 2006b
46 heteroclitalactones E 12-OAc, 20-OH, ∆6,7 异形南五味子K. heteroclita (s) Wang et al., 2006b
47
schisanlactone A
∆1,8,10 (19)
Schisandra sp. (s)
长梗南五味子K. longipedunculata (s)
合蕊五味子S. propinqua (s)
Liu et al., 1983b
Sun et al., 2006
Chen et al., 2001b
48 schisanlactone C ∆1,8,10 (19), 20-OH Schisandra sp. (f, s)
合蕊五味子S. propinqua (s)
Liu & Ma, 1984b
Kuo et al., 1999
49 lancilactone A 6-βOH, ∆1,8,10 (19) K. lancilimba (s) Chen et al., 1999
50 lancilactone B ∆1,6, 8,10 (19) K. lancilimba (s) Chen et al., 1999
51 lancilactone C K. lancilimba (s) Chen et al., 1999
52 schiprolactone A 合蕊五味子S. propinqua (s)
翼梗五味子S. henryi (s)
Chen et al., 2001b
Chen et al., 2003
53 schisanterpene A 合蕊五味子S. propinqua (s)
滇五味子S. henryi Clarke var. yunnanensis
A. C. Smith (s)
Zhou et al., 2002
Li et al., 2004b
1) Ac C
O
CH3
2) f, 果实; s, 茎。f, fruits; s, stems.
图10 五味子科植物中7/7/5/6型三萜内酯的结构
Fig. 10. Structures of 7/7/5/6 type triterpene lactones from Schisandraceae.
表10 五味子科植物中7/7/5/6型三萜内酯
Table 10 7/7/5/6 type triterpene lactones from Schisandraceae
序号
No.
化合物名称
Compound
结构
Structure
来源植物1)
Plant source1)
文献
Reference
54 kadlongilactone A 长梗南五味子Kadsura longipedunculata (s) Pu et al., 2005
55 kadlongilactone B 长梗南五味子K. longipedunculata (s) Pu et al., 2005
56 longipedlactone A R1=H, R2=H, ∆10,19 长梗南五味子K. longipedunculata (s) Pu et al., 2006
57 longipedlactone E R1=H, ∆16, R2=OH, ∆10,19 长梗南五味子K. longipedunculata (s) Pu et al., 2006
58 longipedlactone F R1=OH, ∆16, R2=H, ∆10,19 长梗南五味子K. longipedunculata (s) Pu et al., 2006
59 longipedlactone B R1=H, R2=H, R3=H, ∆10,19 长梗南五味子K. longipedunculata (s) Pu et al., 2006
60 longipedlactone C R1=H, R2=H, R3=OH,∆10,19 长梗南五味子K. longipedunculata (s) Pu et al., 2006
61 longipedlactone H R1=OH, R2=H, R3=H,∆10,19 长梗南五味子K. longipedunculata (s) Pu et al., 2006
62 longipedlactone D R1=H,(10,19 a trisubstituted epoxide) 长梗南五味子K. longipedunculata (s) Pu et al., 2006
63 longipedlactone G R1=OH, ∆16 长梗南五味子K. longipedunculata (s) Pu et al., 2006
64 longipedlactone I R1=R2=OH 长梗南五味子K. longipedunculata (s) Pu et al., 2006
1) f, 果实; s, 茎。f, fruits; s, stems.
植物分类学报 Journal of Systematics and Evolution 2008 46卷5期 710
图11 五味子科植物中类三萜内酯的结构
Fig. 11. Structures of nor-triterpene lactones from Schisandraceae.
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表11 五味子科植物中类三萜内酯
Table 11 Nor-triterpene lactones from Schisandraceae
序号
No.
化合物名称
Compound
结构1)
Structure1)
来源植物2)
Plant source2)
文献
Reference
65 pre-schisanartanin 五味子Schisandra chinensis (s) Huang et al., 2007a
66 henridilactone A R1=OH, R2=CH3, R3=H, R4=H, ∆7 滇五味子S. henryi var. yunnanensis (s) Li et al., 2004b
67 henridilactone B R1=OH, R2=CH3, R3=OH, R4=H, ∆7 滇五味子S. henryi var. yunnanensis (s) Li et al., 2004b
68 henridilactone C R1=CH3, R2=H, R3=H, R4=H, ∆7 滇五味子S. henryi var. yunnanensis (s) Li et al., 2004b
69 lancifodilactone D R1=H, R2=CH3, R3=H, R4=H, ∆7 狭叶五味子S. lancifolia (s) Li et al., 2004b
70 lancifodilactone B R1=H, R2=CH3, R3=H, R4=OH,
7,8-cyclo
狭叶五味子S. lancifolia (s) Li et al., 2004b
71 lancifodilactone N R1=H, R2=CH3, R3=H, R4=OH, ∆7 狭叶五味子S. lancifolia (s) Xiao et al., 2006a
72 micrandilactone F R1=OH, R2= CH3, R3=H, R4=H, ∆7 小花五味子S. micrantha (s) Li et al., 2005a
73
micrandilactone A
7-αOH, 20-αCH3, 20-βOH,
22-αOH, R5=OH
小花五味子S. micrantha (s) Li et al., 2003c
74 henridilactone D R1=CH3, R2=H, R3=H, R4=H, R5=OH 滇五味子S. henryi var. yunnanensis (s) Li et al., 2004b
75 lancifodilactone C R1=H, R2=CH3, R3=H, R4=H, R5=OH 狭叶五味子S. lancifolia (s) Li et al., 2004c
76 lancifodilactone E R1=CH3, R2=H, R3=H, R4=OH,
R5=OH
狭叶五味子S. lancifolia (s) Li et al., 2004c
77 lancifodilactone L R1=H, R2=CH3, R3=H, R4=OH,
R5=OH
狭叶五味子S. lancifolia (s) Xiao et al., 2006a
78 micrandilactone D R1=OH, R2=CH3, R3=H, R4=H,
R5=OH
小花五味子S. micrantha (s) Li et al., 2005a
79 micrandilactone E R1=CH3, R2=OH, R3=H, R4=H,
R5=OH
小花五味子S. micrantha (s) Li et al., 2005a
80 micrandilactone G R1=H, R2=CH3, R3=H, R4=H, R5=OH 小花五味子S. micrantha (s) Li et al., 2005a
81 lancifodilactone M R2=CH3, ∆20(22), R4=H, R5=OH 狭叶五味子S. lancifolia (s) Xiao et al., 2006a
82 lancifodilactone I R=OH 狭叶五味子S. lancifolia (s) Xiao et al., 2006a
83 lancifodilactone J R=OAc 狭叶五味子S. lancifolia (s) Xiao et al., 2006a
84 lancifodilactone K ∆7 狭叶五味子S. lancifolia (s) Xiao et al., 2006a
85 lancifodilactone G 狭叶五味子S. lancifolia (s) Xiao et al., 2005b
86 lancifodilactone A 狭叶五味子S. lancifolia (s) Li et al., 2003b
87 wuweizidilactones A R=O 五味子S. chinensis (s) Huang et al., 2007c
88 wuweizidilactones B R=α-OAc 五味子S. chinensis (s) Huang et al., 2007c
89 wuweizidilactones C R1=OAc, R2=OH, R3=H 五味子S. chinensis (s) Huang et al., 2007c
90 wuweizidilactones D R1=H, R2=OH, R3=H 五味子S. chinensis (s) Huang et al., 2007c
91 wuweizidilactones E R1=H, R2=OAc, R3=H 五味子S. chinensis (s) Huang et al., 2007c
92 wuweizidilactones F R1=H, R2=OAc, R3=OH 五味子S. chinensis (s) Huang et al., 2007c
93 lancifodilactone F 狭叶五味子S. lancifolia (s) Xiao et al., 2005a
94 micrandilactone B 小花五味子S. micrantha (s) Li et al., 2005b
95 micrandilactone C 小花五味子S. micrantha (s) Li et al., 2005b
96 rubriflordilactones B 红花五味子S. rubriflora (s) Xiao et al., 2006c
97 rubriflordilactones A 红花五味子S. rubriflora (s) Xiao et al., 2006c
98 sphenadilactones A 华中五味子S. sphenanthera (s) Xiao et al., 2006d
99 sphenadilactones B 华中五味子S. sphenanthera (s) Xiao et al., 2006d
100 schintrilactone A R1=CH3, R2=H 五味子S. chinensis (s) Huang et al., 2007b
101 schintrilactone B R1=H, R2=CH3 五味子S. chinensis (s) Huang et al., 2007b
102 schindilactone A R1=H, R2=CH3, R3=H, R4=H, ∆7 五味子S. chinensis (s) Huang et al., 2007a
103 schindilactone B R1=CH3, R2=R3=R4=H, ∆7 五味子S. chinensis (s) Huang et al., 2007a
104 schindilactone C 五味子S. chinensis (s) Huang et al., 2007a
1) Ac C
O
CH3
2) f, 果实; s, 茎。f, fruits; s, stems.
植物分类学报 Journal of Systematics and Evolution 2008 46卷5期 712
图12 五味子科植物中各类三萜成分之间的演化关系(Li et al., 2003a; Shen et al., 2005a; Pu et al., 2006; Huang et al., 2007a, b)
Fig. 12. Proposed biogenetic relationships between different triterpene types in Schisandraceae (Li et al., 2003a; Shen et al., 2005a; Pu et al., 2006;
Huang et al., 2007a, b).
表12 三萜类化合物在五味子科药用植物中的分布
Table 12 Distribution of triterpenes in family Schisandraceae
三萜类化合物
Triterpenes
种
Species
I
环菠萝蜜烷型三
萜(A环闭环)
Cycloartanone
triterpenes (A-ring
A close)
II
菠萝蜜烷型三萜
(A环开环)
Cycloartanone
triterpenes (A-ring
open)
III
7/6/6/5或者
7/7/6/5三萜
7/6/6/5 or 7/7/6/5
type triterpenes
IV
7/7/5/6型三萜
内酯
7/7/5/6 type
triterpene
lactones
V
类三萜内酯
Nor-triterpe
ne lactones
五味子Schisandra chinensis (s) 1 12
华中五味子S. sphenanthera (s) 3 2
红花五味子S. rubriflora 2
翼梗五味子S. henryi 2 2 2
滇五味子S. henryi var. yunnanensis (s) 1 4
合蕊五味子S. propinqua 3 2 5
S. nigra 2
小花五味子S. micrantha (s) 2 1 7
狭叶五味子S. lancifolia (s) 1 2 13
黑老虎Kadsura coccinea 1 1
异形南五味子K. heteroclita 8 9 3
长梗南五味子K. longipedunculata 6 3 1 11
K. lancilimba 4
狭叶南五味子K. angustifolia 2
菲律宾五味子K. philippinensis 1
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来作为五味子的代用品, 主要用来治疗肺虚久咳,
失眠多梦, 自汗盗汗等症。在南五味子属中8种具有
药用价值, 该属大多植物多为地方习用药材, 以藤
茎入药, 通常称风藤、紫金皮等, 具有活血通络、
祛风除湿的作用。如凤庆南五味子在云南作为鸡血
藤治疗妇科疼痛, 异形南五味子在广东、广西作为
海风藤治疗风湿痹痛, 其他南五味子属植物在民间
也广泛用于治疗各种痛症, 在中国西南分布最为集
中的是长梗南五味子和黑老虎, 用作治疗跌打损
伤、风湿骨痛、胃病、月经不调等症。此外, 五味
子属药用植物的藤茎通常称血藤, 如翼梗五味子、
小花五味子, 与南五味子属植物藤茎药效相似。
4 现代药理/生理活性研究及主要物质基础
4.1 现代药理活性研究及主要物质基础
4.1.1 镇静催眠作用 五味子水/乙醇提取物以及
其主要有效成分五味子醇甲等对中枢神经有显著
的镇静、催眠、抗惊厥作用。研究表明五味子乙醇
提取液、北五味子水提取物均可使小鼠自主活动明
显减少(霍艳双等, 2005), 对抗中枢兴奋药苯丙胺对
自主活动的兴奋作用, 可明显延长阈上睡眠剂量戊
巴比妥钠致小鼠睡眠时间。五味子仁乙醇提取物中
主要有效成分之一五味子醇甲能明显加强利血平
及戊巴比妥钠对自主活动的抑制作用, 对抗咖啡
因、苯丙胺对自主活动的兴奋作用, 抑制小鼠由电
刺激或长期单居引起的激怒行为。此外, 五味子醇
甲还能对抗MES、戊巴唑、瘀碱及北美黄连碱的强
直惊厥(郭冷秋等, 2006)。
4.1.2 止咳祛痰 用五味子及其乙醚提取物, 无论
灌胃给药或腹腔注射, 对氨水引咳的小鼠均有止咳
作用, 小鼠酚红试验表明, 五味子有祛痰效果, 从
五味子中分离得到的两种结晶物均有明显镇咳作
用(何来英等, 2004)。五味子水煎液不仅使小鼠气管
腺内花生素(PNA)和双花扁豆素(DBA)结合的中性
黏多糖明显减少, 而且使酸性黏多糖也相应减少,
形态和组织化学检查结果证实五味子的酸性成分
有祛痰作用(郭冷秋等, 2006)。上述研究为五味子果
实止咳化痰的传统疗效提供了科学合理的解释。
4.1.3 保肝作用 五味子保肝作用的主要物质基
础为联苯环辛烯类木脂素。研究发现, 五仁醇等能
降低四氯化碳(CCl4)或其他化学物质如硫代乙酰胺
(TAA)、扑热息痛引起的实验动物SGPT升高, 减少
肝内GSH含量的下降, 促进肝细胞蛋白质的合成,
促进线粒体恢复和再生(卢华, 刘耕陶, 1990)。五味
子对大鼠肝微粒体细胞色素P450具有明显的诱导
作用, 其保肝作用可能与诱导肝药酶加快某些有毒
物质的代谢有关(张锦楠等, 2002)。五仁醇的主要成
分甲素、乙素、丙素、醇乙、五酚均能显著提高肝
微粒体细胞色素P450、NADPH-细胞色素P450还原
酶、氨基比林脱甲基酶及苯并芘羟化酶活性, 微粒
体蛋白亦显著增加, 还能促进肝糖元的合成, 增加
肝细胞的能量储备(刘耕陶, 1987), 且发现乙素和醇
乙主要诱导滑面内质网的细胞色素P450B2部分 ,
属苯巴比妥型的P450诱导剂(刘耕陶, 1987, 1988)。
从K. matsudai Hayata和阿里山五味子分得的联苯环
辛二烯木脂素(Gomisin K3, kadsurarin, Schizanrins
B、C、D、E, taiwanschirin D等)在抗HBsAg、HBeAg
试验中显示出不同程度的抗肝炎活性(Li et al.,
2000; Wu et al., 2003; Kuo et al., 2005a)。阿里山五味
子来源的联苯环辛烯木脂素gomisin B, G and
(+)-gomisin K3通过抗HbsAg、HBeAg抗原发挥抗肝
炎作用(Wu et al., 2003)。
4.1.4 抗肿瘤 五味子乙素对小鼠腹水型肝癌细
胞、小鼠S180-V癌细胞和人胚肺成纤维细胞DNA合
成具有明显抑制作用, 还可抑制腹水型肝癌细胞的
核蛋白和ATP代谢的动态过程, 表明五味子乙素对
癌细胞的增殖和代谢均有抑制作用 (刘力生等 ,
1984a)。Kadsulignan C、D、H、K, epienshicine,
wulignanA1、A2、epiwulignan A1、epischisandrone、
epienshicine及changnanic acid、schisanlactone E体外
对P388细胞均有不同程度的抑制作用(Liu et al.,
1988)。体外实验证实, 五酯酮A、B, 五内酯E、F, 长
南酸均有显著抑制小鼠白血病细胞株P388增殖的
作用(Li et al., 1989c, You et al., 1997)。Schisari-
sanrin C对KB、Colo-250、HEPA-3B和HEPA等肿瘤
细胞株有细胞毒作用(Chen et al., 1996)。Gomisin A
能抑制3′-甲基-4二甲基氨基偶氮苯(3′-MeDAB)引
起的大鼠肝癌前损伤及12-O-十四烷酰基佛波醇
-13-己酯促进7,12-二甲基并蒽诱导的小鼠皮肤癌,
Manwuweizic acid具有抑制小鼠Lewis肺癌, 脑瘤
-22和肝硬化的作用(Liu et al., 1988a)。从阿里山五
味子中得到的tanwanschirin C和schizarin A显示了
对Hepa-3B肿瘤细胞的细胞毒性作用, 并且认为6位
植物分类学报 Journal of Systematics and Evolution 2008 46卷5期 714
取代与活性间存在构效关系(Kuo et al., 1999)。从合
蕊五味子中分得的三萜酸nigranoic acid和manwu-
weizic acid, 在体外对人蜕膜细胞及大鼠黄体细胞
具有很强的细胞毒性活性(Chen et al., 2001d)。从翼
梗五味子茎分得三萜类化合物schiprolactone A、
schisanlactone B、nigranoic acid和schisandronic acid,
在体外对Leukemia肿瘤细胞株显示活性 , schi-
sanlactone B和schisandronic acid对Leukemia细胞株
显示了中等强度的细胞毒活性(Chen et al., 2003)。
从中泰南五味子茎分离得到两个三萜酸ananosic
acids B、C, 对CCRF-CEM和HeLa肿瘤细胞表现出
细胞毒性(Chen et al., 2004b)。从凤庆南五味子分得
木脂素interiotherins C、interiotherins D、interiorin、
heteroclitin F 、 neokadsuranin 、 heteroclitin D 、
kadsurin、gomisin A、schisandrin C、interiotherin A、
angeloylgomisin R、gomisin G、interiotherin B和
gomisin C, 可以抑制EB病毒对Raji细胞的感染, 可
能作为抗肿瘤预防用药 (Chen et al., 2002a)。
Schisandrin B对P-糖蛋白有很强的抑制作用, 可以
逆转P-糖蛋白过表达介导的肿瘤细胞多药耐药现
象, 从而发挥抗肿瘤作用, 有望成为一种新的抗肿
瘤制剂(Pan et al., 2005)。从长梗南五味子藤茎中分
离得到的三萜化合物 kadlongilactones A和B在体外
对人肿瘤细胞株K562增殖有明显的抑制作用(Pu et
al., 2005), 三萜化合物longipedlactone A、B、C、F
和H在体外对A549、HT-29和K562具有明显的细胞
毒性(Pu et al., 2006)。Gomisin G体外对肿瘤细胞株
Leukemia 和Hela显示了很强的细胞毒活性(Chen et
al., 2005b)。本课题组从铁箍散藤茎中分离得到的木
脂素propinquanin B体外对肿瘤细胞株HL-60和
Hep-G2显示了强细胞毒活性(Xu et al., 2006)。
Lancifodilactone G和Lancifodilactone F在体外对
C8166细胞显示温和的细胞毒活性 (Xiao et al.,
2005a, b)。五味子多糖合用环磷酰胺抑瘤率达
74.5%, 五味子多糖对荷瘤小鼠的免疫器官有较好
的保护作用, 说明五味子多糖能抑制肿瘤的生长,
多糖的抑瘤作用可能不是直接杀死瘤细胞, 而与细
胞凋亡及活化免疫细胞有关(黄玲等, 2003)。
4.1.5 抗HIV作用 五味子中活性成分联苯环辛二
烯木脂素被证实在细胞和分子水平均具有抗艾滋
病活性 (李伟等 , 2002)。Kadsulignan M体外对
CEM-IW细胞系(T4淋巴细胞)有较强的抑制活性
(Liu & Li, 1995b)。球蕊五味子中分到的三萜酸
nigranoic acid 具有抑制HIV逆转录酶和多聚酶的
作用(Sun et al., 1996)。凤庆南五味子茎的乙醇提取
物体外对HIV病毒在H9淋巴细胞中的复制有显著
抑制作用, 对从中分到的12个木脂素进行抗HIV生
长试验, 7个化合物有活性, 其中gomisin G活性最
强, 五味子酯丁, kadsuranin和五味子丙素也显示了
强的抗HIV活性(Chen et al., 1996)。构效关系研究表
明, 6位具苯甲酰基和7位取代羟基, 2,3位有亚甲氧
基取代对增强抗HIV活性是很重要的(Chen et al.,
1997)。从披针叶南五味子中分到的三萜类内酯
lancilactone C在体外可抑制HIV病毒在H9淋巴细胞
中的复制 (Chen et al., 1999)。从小花五味子中分离
得到的木脂素Vladinol F具有显著的抗HIV活性, 李
蓉涛等 (2005a)从该植物中分离得到的新三萜
Micrandilactone C能抑制HIV-1复制, 且对正常细胞
具有极低的毒性, 有可能成为一类新的抗HIV药
物。从狭叶五味子分离得到的三萜类化合物Lanci-
fodilactone G和F均表现出了明显的抗HIV病毒活性
(Xiao et al., 2005a, b)。从长梗南五味子藤茎中分离
得到Longipedunin A和schisanlactone A对HIV-1蛋
白酶具有较好的抑制作用(Sun et al., 2006)。
4.2 现代生理活性研究及主要物质基础
4.2.1 对免疫功能的影响 五味子水提物和五味
子粗多糖具有升高白细胞及增强机体免疫、抗疲劳
的作用(Ikeya et al., 1978a, b; Chen et al., 1997)。研究
表明, 五味子提取物能促进唾液腺内半乳糖和乙酰
胺半乳糖的合成, 促进免疫细胞分化, 增强免疫功
能, 能明显对抗环磷酰胺所致小鼠脾脏和肠系膜淋
巴结重量及细胞数目的减少, 并能增加免疫抑制小
鼠的脾脏白髓总体积和淋巴结皮质总体积, 且对免
疫器官的病理形态有一定的改善作用(黄秀兰等,
1997)。用五味子粗多糖给小鼠灌胃, 能明显提高小
鼠的耐缺氧能力, 具有抗疲劳作用, 升高白细胞的
同时, 可对抗环磷酰胺的免疫抑制作用, 使正常小
鼠胸腺和脾脏的重量增加, 提高机体免疫力, 并增
强小鼠静脉注射胶体碳粒的廓清速率, 减轻肌体损
伤(李岩等, 1995; 于晓凤等, 1995)。
4.2.2 抗氧化 现代研究表明五味子的保肝作用
与增强肝脏抗氧化能力有关(Ip et al., 1996)。研究表
明, 很多木脂素都具有在体内外对多种氧化应激损
伤的组织模型明显的保护作用。例如从五味子中提
许利嘉等: 五味子科药用植物亲缘学初探
715
取的五味子乙素、五味子二醇、五味子酮对维生素
C/NADPH系统或FeSO4/半胱氨酸系统诱发的脑、
肝、肾微粒体脂质过氧化有明显抑制作用(黄治森
等, 1990)。五味子乙素可对抗CCl4引起的大鼠肝细
胞膜脂质过氧化, 使肝细胞MDA的生成及LDH和
GPT的释放均减少, 肝细胞的存活率提高, 这与它
清除氧自由基有关(李莉, 刘耕陶, 1998; 张铁梅等,
1989; Ko & Lam, 2002; Ko et al., 2002)。从红花五味
子中分离出的五味子酚(schisanhenol, SAL)能抑制
大鼠肝、脑及心肌细胞MDA的生成, 可防止氧自由
基引起的线粒体肿胀、破裂及ATP酶活性降低, 能
保护脾淋巴细胞免受氧自由基的损伤, 提高淋巴细
胞内GSH的含量, 拮抗过氧化氢对ConA刺激脾淋
巴细胞增生及Fe2+/Vit C对脾淋巴细胞膜的损伤(李
莉, 1997)。电子自旋共振法和自旋捕捉技术证明,
五味子酚具有直接清除活性氧自由基的活性(林童
俊等, 1990), 能降低脂质过氧化对脑神经细胞突触
体膜的损伤程度, 从而起到保护作用, 且在体内外
对多种氧化应激损伤脑组织模型都具有明显的保
护作用(郭琼, 赵保路, 1995; 李莉, 刘耕陶, 1998)。
从凤庆南五味子中分到的木脂素戈米辛J具有对抗
羟自由基诱导的肝线粒体膜脂质过氧化和清除超
氧化阴离子自由基的作用, 其作用比Vit E强, 剂量
依赖性地抑制黄嘌呤/黄嘌呤氧化酶/鲁米诺化学发
光(金昔陆等, 2000)。异形南五味子茎的乙醇提取物
和其主要有效成分南五味子素可以明显减少CCl4
引起的小鼠肝脏过氧化脂质产物如MDA等的产生,
同时还可明显恢复SOD活性, 诱导肝脏抗氧化酶清
除氧自由基(Kim et al., 1992)。由异形南五味子植物
根部分离的联苯环辛烯类木脂素(heteroclitin A-G)
具有明显的抗脂质过氧化作用, 其中异形南五味子
丁素(heteroclitin D)对Fe2+/Vit C诱导的肝匀浆脂质
过氧化的抑制作用最强(李庆耀等, 1999a)。长梗南
五味子木脂素在体外可抑制脂质过氧化反应及超
氧阴离子的产生(Lu & Liu, 1992)。从五味子中分离
得到的联苯环辛二烯木脂素 deoxyschisandrin,
gomisin N, and wuweizisu C能明显减弱谷氨酸诱导
的神经细胞氧化性损伤作用, 其作用与升高谷胱苷
肽水平, 提高谷胱苷肽过氧化物酶活性, 以及抑制
细胞内过氧化物生成有关(Kim et al., 2004)。
4.2.3 PAF拮抗活性 研究发现, 多种木脂素有
PAF拮抗活性, 五味子中的15个木脂素有不用程度
的钙拮抗作用, 从五味子中提取戈米辛A、B、D、
G、H五味子素、五味子丙素、前戈米辛等木脂素
成分, 对PGF22引起的离体狗肠系膜动脉收缩有缓
解作用, 而对CaCl2引起的收缩具有抑制作用(郭冷
秋等, 2006), 戈米辛J和异形南五味子丁素能阻滞
血管平滑肌细胞膜的PM而发挥扩血管作用(李庆耀
等, 1999b)。从凤庆南五味子和异形南五味子中分离
得到的异形南五味子丁素heteroclitin D具有显著的
钙拮抗、抗凝血和抑制血小板聚集等作用, 这些结
果初步向我们提示了在民间南五味子属药用植物
藤茎具有较强活血化瘀药理作用的活性物质基础。
5 五味子科药用植物亲缘学初探
我们通过对五味子科药用植物传统疗效、现代
药理活性以及化学成分的整理和总结发现, 五味子
科药用植物的现代药理活性研究与传统疗效之间有
很好的相关性, 且很多活性也找到了相对应的物质
基础, 同时也向我们提示两属植物功效主治上差别
的物质基础与特征性成分有关。
北五味子中五味子醇甲和醇乙的含量都很高,
尤其是醇甲, 药典规定北五味子醇甲的含量不能少
于0.4%, 而现代药理活性研究证明了五味子提取物
及主要活性成分醇甲的镇静催眠抗惊厥作用, 这为
五味子宁心安神的传统疗效提供了科学合理的解
释。而五味子传统疗效中的滋补强壮、益肾固精在
现代药理中可以找到如下关联: 第一、五味子粗多
糖具有升高白细胞及增强机体免疫、抗疲劳的作用;
第二、五味子的保肝作用, 发挥五味子保肝作用的
成分联苯环辛烯类木脂素通常在八元环的C-6和C-9
没有酯化取代集基团; 第三、联苯环辛烯类木脂素
的抗氧化作用, 据医学研究表明一些老年性疾病如
帕金森病, 老年性痴呆, 糖尿病等病的发生与体内
自由基反应密切相关, 自由基可引发脂质过氧化造
成细胞损伤, DNA断裂, 蛋白交联等, 而五味子属
植物中很多联苯环辛烯类木脂素在体内外对多种氧
化应激损伤的组织模型都具有明显的保护作用, 同
样, 这类木脂素往往在八元环的C-6和C-9没有酯化
取代基团, 很多研究也表明一些木脂素正是通过抗
脂质过氧化来发挥保肝作用的。这类成分在五味子
的果实以及南北五味子的藤茎中广泛分布, 今后有
望从这些较为原始的联苯环辛烯类木脂素中深入研
植物分类学报 Journal of Systematics and Evolution 2008 46卷5期 716
图13 五味子药用植物传统疗效-现代药理作用-活性成分之间可能存在的联系
Fig. 13. Proposed relationships between ethnopharmacology, pharmacology and bioacitive constituents from family Schisandraceae.
究开发, 挖掘出增强机体免疫力, 延缓衰老的抗氧
化药物(图13)。
螺苯骈呋喃骨架的联苯环辛烯类木脂素是一类
特别值得注意的化学成分, 这是一类较联苯环辛烯
类木脂素更为进化的成分, 到目前为止, 这类成分
绝大多数只在南五味子属植物的藤茎中分布, 可以
被认为是南五味子属植物中的特征性活性成分, 如
南五木脂素C–K、异形南五味子素D–G和凤庆南五
味子素A–D等, 这类化合物的特点是具有钙拮抗、
抗凝血和抑制血小板聚集作用, 这不仅初步说明了
民间南五味子属药用植物藤茎具有较强活血化瘀药
理作用的活性物质基础, 也向我们提示在对南五味
子属的药材质量标准研究中, 可以考虑以此类成分
作为定性定量指标。同时也有研究报道, 这一类木
脂素中尤其是在C-9位上有酯化取代基团的, 往往
也具有抗脂质过氧化的作用。
《本草纲目》曾有对五味子的记载：“对痰咳并
喘, 百药不效者均可治愈”。随着研究的不断深入,
五味子科药用植物中越来越多的结构新颖的木脂素
和三萜类成分被发现, 因此这些成分的一些特殊的
药理活性也得到了越来越广泛的关注。在最近的研
究中我们发现, 五味子除了传统的保肝作用以外,
很多三萜和木脂素具有相当好的抗肿瘤和抗HIV活
性, 这或许就是传统意义上的“百药不效者均可治
愈”。通过总结, 我们发现一些联苯环辛烯类的木脂
素尤其是在八元环C-6、C-9位上具有羟基或者酯化
取代比如当归酰基取代的比八元环无取代的木脂素
具有更好的抗HIV和抗肿瘤活性, 这向我们提示,
发挥传统保肝作用的木脂素更为原始, 而衍化程度
相对进化的木脂素则更具有抗肿瘤和抗HIV的潜
力。对于环菠萝蜜烷三萜来说, 在取代基相同的情
况下, A环裂环将增强抗肿瘤和抗HIV活性, 这一类
化合物就传统的环菠萝蜜烷类更为进化, 是值得深
入研究和开发的化合物, 它们在五味子科和八角科
的药用植物中均有分布, 南五味子属的异形南五味
子、长梗南五味子、黑老虎这几种药用植物在民间
应用较多、分布较广, 它们的藤茎中都曾报道有A
环裂环的环菠萝蜜烷型三萜类化合物, 在五味子属
的铁箍散、翼梗五味子的藤茎中也有此类化合物的
报道。最新的研究报道显示更为进化的7/7/5/6型三
萜内酯体外对肿瘤细胞株显示了很强的细胞毒活性,
目前主要在南五味子属的长梗南五味子中发现此类
化合物, 有望通过对此类成分的深入挖掘而从中开
发抗肿瘤预防用药, 同样, 从狭叶五味子和小花五
味子等分离得到的成环复杂、氧化程度很高的类三
萜内酯也在抗肿瘤和抗HIV中显示了很好的潜力,
这向我们提示, 进化程度更高的三萜化合物很值得
关注。
许利嘉等: 五味子科药用植物亲缘学初探
717
通过上述比较和总结, 我们不难发现在五味子
科植物中发挥传统疗效的往往是那些较为原始的化
合物, 而新颖的活性往往都在进化程度较高的化合
物中发现。我国五味子科植物资源十分丰富, 大量
系统、深入、客观全面的研究仍有待继续, 以使该
科的药用植物亲缘学研究得到完善。
另外 , 药典已将五味子属华中五味子 S.
sphaerandra的干燥果实定为南五味子, 而传统将
Kadsura译为南五味子属, K. japonica (L.) Dunal和K.
longipedunculata Finet & Gagnep.的中文名称也多被
用为南五味子, 药典中的南五味子与Kadsura并非
从属关系, 如此译名容易造成名称混乱和概念混淆,
作者建议今后应将Kadsura译为更恰当的属名。
致谢 本研究得到国家自然科学基金(30530860)资
助。
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