全 文 ：The Researches on the Terpenoids from Juniperus
WANG Wen-shu ,FENG Jin-chao ,LU Peng
(College of Life and Environmental Sciences , Central University for Nationalities , Beijing　100081 , China)
Abstracts:The studies of the tepennoids in Juniperus from 1980 -2006 are summarized here.All the terpenoids in
Juniperus have complicated structures , including changeful skeletons and abundant functional groups.Furthermore , some of
those compounds show kinds of bioactivities.It can be concluded that studies on Juniperus is valuable and continuable.
Key words:Cupressaceae;Juniperus;Sabina;Sesquiterpenoids;Diterpenoids
中图分类号:Q946　　文献标识码:A　　文章编号:1005-8036(2008)01-0053-06
收稿日期:2007-06-25
基金项目:CUN985-03-03.
作者简介:王文蜀(1974-),女(汉族),四川成都人 ,中央民族大学生命与环境科学学院副教授 , 主要研究方向:天然
有机化学.
　　Juniperus is a kind of evergreen arbor or shrubbery , belonging to gymnosperm , which includes about 60
species distributing in the Northern Hemisphere.There are round about 20 species in China.Some species in the
genera are cultivated as garden or familial-ornamental trees[ 1] .
In ancient China , characters of components in Juniperus were depicted.Li Shi-zhen recorded in Compendium
of Materia Medica .wood .cypress that “cypress includes some species , only the species having oblate and by-side
growing leaves can be used as herbal medicine” .Now leaves of some trees in Juniperus are used as folk medicines
to cure emptysis , bleeding in emiction and stool , and chincough[ 2] .Therefore , trees in Juniperus are useful natural
resource for mankind.
Modern studies on components in Juniperus began in the 1970 s , which was to analyze trees essential oil to
provide chemical evidence for plant taxonomy
[ 3] .The result shows that there are a large number of monoterpenes and
sesquiterpenes in the oil of Juniperus.
Because of abundant structure types and obvious bioactivities , complex terpenoids are always important targets
for chemists , as good source of physiological activity molecules and environment-protecting insecticides.From the
1980 s , lots of sesquiterpenoids and diterpenoids were isolated from Juniperus.Here , we summarize the results of
terpenoids from Juniperus , according to different species.Structures of terpenoids with novel skeletons or showing
bioactivities are exhibited in the figures.
Juniperus chinensis Linn.Sesquiterpenes (S1 -S4)were isolated[ 4] .A new dimeric himchalane-type
sesquiterpene(DS1)was afforded from the root , structure of which was identified by X-ray analyzing[ 5] .Labdanes
(L1-L4)was isolated from the bark[ 6] , while totaranes(T1-T10 , NT1-NT2 , ST1)and chinane(C1)from the
leaves
[ 7] , and pimarane (P1)from the roots[ 8] .Two sesquiterpenes(S5)and 8-hydroxyelemol showed antifungal
activities
[ 9] .From the heartwood of J .chinensis Linn.Var.Tsukusiensis Masam , a new sesquiterpenes(S6)were
afforded
[ 10] .From leaves and barks of J .chinensis kaizuka (S7-S8)[ 11] and 8 , 19-dioxo-8 , 14-seco-chinan-14 ,
2008年 2月
第 17卷　第 1期
中央民族大学学报(自然科学版)
Journal of the CUN(Natural Sciences Edition)
Feb.2008
Vol.17　No.1
11-olide (SC1)with a novel skeleton , in addition to abietanes(A1 , A2)and labdanes(L5 , L6)[ 12] were afforded.
Fig.1　Chinanes from Juniperus
Juniperus formosana Hayata.is indigenous to Taiwan.Sesquiterpenes
(S9)with novel skeleton[ 13] and new abietanes(A3-A5)[ 14] were reported.
Junipenonoic acid(S10)was yeilded from the heartwood of the variety[ 17] .
Juniprus.communis L.is a medicinal plant in Bhutan.Labdanes (L8 ,
L9)were afforded by centrifugal partition chromatography (L10)[ 18] .Pimaranes
(P2 , P3)are the main terpenoids in its berries[ 19] .Japanese reported a labdane
Fig.2　Sesquiterpenoids from Juniperus
(L11)in the tree is a platelet aggregation inhibitor[ 20] .Monoterpene glycoside(MG1)and megastigmanes were the
results of research on Juniperus communis Var.depressa [ 21] .
Fig.3　Totoranes f rom Juniperus
54 中央民族大学学报(自然科学版) 第 17卷　
Fig.4　Glucosides of terpenoids from Juniperus Fig.5　Pimaranes f rom Junipeurs
　　Juniperus thurifera Oygenated abietanes , as well as norabietane and secoderivatives (A7 -A10)were
distinctive compounds in this species
[ 22 ～ 23] .labdane acids(L12-16)[ 24] were also afforded.The extended research
by Spanish gave novel tricyclic sesquiterpenes with usual duprezianane (S11)and cedrane skeleton(S12-S17),
stereochemistry of the compounds was determined carefully by spectroscopic analysis or chemical transformation
[ 25] .
Fig.6　Labdanes f rom Juniperus
Juniperus oxycedrus L.was reported to have oxygenated sesquiterpenes(S18-S20)[ 26] .Junicedranol(S21)
with a complex bridge ring structure was afforded from Juniperus oxyadrus ssp.Macrocarpa and the absolute
stereochemistry was determined by Mosher s Methods[ 27] .
Juniperus phoenicea L.Labdanes(L17)[ 28] and oplopanes(S22)were gotten from its berries[ 29] .Norterpenoid
and sesquiterpenoid glucosides(SG1)were reported[ 30] .
Juniperus Sabina L.is a source of insecticides in the northwestern part of China.Oplapenones(S23)were
isolated from berries
[ 31] , more than 20 diterpenes were afforded from its essential oil(A11 , L18)[ 32] .
Juniperus excelsa Bieb.New diterpenes(A12)and(L19-L20)[ 33～ 34] were afforded.Furthermore , Labdanes
in the leaves and seeds showed antibacterial activities
[ 35] .
55　第 1期 WANG Wei-shu等:The Researches on the Terpenoids f rom Juniperus
Juniperus squamata is native to Himalaya.cedranes , such as epicedranediol (S24)and 3(-hydroxycedrol
(S25)were reported[ 36] .
Juniperus procera Hochst.Ex Endl.is used as herbal medicine in Africa.Studies guided by antibacterial
activities afforded diterpenoids , including norlabdanes(L21 , L22)[ 37] .
Fig.7　Abietanes from Juniperus
Juniperus pseudosabina Hook is a robust shrub or a tree found in the Hamalyayas.Its leaves and twigs are sold
as incense and also as an insect repellent.Indian reported ten labdanes from the extracts of this tree (L23-
26)[ 38] .
Juniperus polycarpos is a multi-seeded juniper in central Asia.Diterpenoids(A13)showing antimicrobial and
anti-inflammatory activities were isolated[ 39] .
Juniperus przwalskii is a special species distributing in the northwest area in China.Its chemical constituents
had never been analyzed until 2002.More than 20 diterpenoids and sesquiterpenoids were isolated from the seeds ,
such as (L27)and (A14), which showed inhibition activity on human carpus carcinoma (HO -8910) cell
lines
[ 40] .
Juniperu recurva Buch distributed in the wetter areas of the Himalayas , smoke of which is emetic and long-
continued vomiting.8-cedren-13-ol(S26)and thujopsene(S27)[ 41] were isolated , as a result of studies guided by
insecticidal tests.
Conclusion:Chemical constituents of Juniperus afforded unusual sesquiterpenoids , which had complex rings and
oxygenated groups.Their structural determination were depended on High resolving power NMR spectrum ,
sometimes even on X-ray data analyses.Labdanes and abietanes are the major diterpenoids in Juniperus , which not
only exhibited abundant skeleton variation , including Nor-derivatives and Seco-derivatives and dimer , but also
showed bioactivities , such as antifungal , antimicrobial activities.It can be concluded that Juniperus is a good
source for chemists to find interesting structure and lead compounds for new drug.About 20 indigenous species in
Juniperus in China have not been studied.Therefore , further studies on the Chinese Juniperul are significative and
valuable.
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圆柏属植物中萜类研究进展
王文蜀 ,冯金朝 ,卢　鹏
(中央民族大学生命与环境科学学院 , 北京 100081)
摘　要:　对 1980 ～ 2006年期间国内外园柏属植物中的萜类化学成分研究进行综述.园柏属中的所有萜类都
有复杂的结构:包括不稳定的碳链和大量的官能团.此外 , 它们中的一些化合物还显示出较丰富的生物活性.
关键词:　柏科;刺柏属;园柏属;倍半萜;二萜
[责任编辑:白　玲]
58 中央民族大学学报(自然科学版) 第 17卷