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含笑属植物所含化学成分与其生物活性的综述(英文)



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DOI:10.3736/jcim20121203
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Kumar D,Kumar S,Taprial S,Kashyap D,Kumar
A,Prakash O.A review of chemical and biological
profile of genus Michelia.J Chin Integr Med.2012;
10(12):1336-1340.
Kumar D,Kumar S,Taprial S,Kashyap D,Kumar
A,Prakash O.含笑属植物所含化学成分与其生物活
性的综述.中西医结合学报.2012;10(12):1336-1340.
Received June 16,2012;accepted August 7,2012;
published online December 15,2012.
Ful-text LinkOut at PubMed.Journal title in PubMed:
Zhong Xi Yi Jie He Xue Bao.
Correspondence:Dinesh Kumar,Assistant Professor;
Tel:+91-1744-239617;E-mail:dineshbarbola@yahoo.
co.in
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                                   Reviews 述评与综述
A review of chemical and biological profile of genus Michelia
Dinesh Kumar,Sunil Kumar,Seema Taprial,Deepak Kashyap,Ajay Kumar,Om Prakash
Institute of Pharmaceutical Sciences,Kurukshetra University,Kurukshetra 136119,Haryana,India
ABSTRACT:The genus Michelia,belonging to family Magnoliaceae,consists of about 80 plant
species mainly distributed in South Asian countries.The plants of this genus have been tradi-
tionaly used in curing various diseases like fever,colic,leprosy,eye disorders,inflammation,
antidote for scorpion,etc.Ninety-four compounds isolated from nine species of the genus Michelia
like sesquiterpenes,steroids,flavonoids,aporphines,phenols,esters,benzenoids and alkaloids
have antibacterial,anticancer and antiplasmodial activities.This review presents first time
detailed information on chemical and biological properties of constituents isolated from the genus
Michelia.
KEYWORDS:Michelia;pharmacologic actions;review
 The genus Michelia(family Magnoliaceae)comprises
about 80species and inhabitates in South-east Asia
from India and Sri Lanka eastwards to South Japan
and Taiwan(China)and southeastwards to Indonesia[1-3],
and about 70species are also distributed from
Southwest to East China[4].Various chemical con-
stituents isolated from different species of the genus
Micheliainclude linalool[5],tetrahydrofuranol[6],apor-
phines,benzenoids,oxoaporphines,steroids,terpe-
noids[7],and bisbenzylisoquinoline alkaloids[8].The
important biological activities of constituents isola-
ted from Micheliaare anticancer[9-11],anti-plasmo-
dial[8]and antibacterial activities[12].Til date no
review has been reported on isolated constituents
and their biological activities from the genus Mich-
elia (Magnoliaceae),therefore,this review has
been compiled to summarize the isolated chemical con-
stituents and their biological activities reported up
to March 2012from genus Michelia (Magnoliace-
ae).
1 Geographical distribution
 The Michelia genus is distributed in different
habitats.Species like M.figo Sprenge.(Magnoliaceae)
is native of South China[13].M.floribunda (Fin &
Gagnap)is a smal tree grown in the northern part
of Thailand[14].M.alba is a tal tree native to
Indonesia and has been used by the native Malays
in Malayasia and Indonesia for medicinal purpose[5].
M.foveolata,a flowering tree up to 30mheight,
grows wild in wet forests of South-east Asia(altitude
500to 1 800m)and is also found in the mountain-
ous North-west of Vietnam[15].M.champaca
Linn.is an evergreen plant occurring in the eastern
·6331· 中西医结合学报2012年12月第10卷第12期 Journal of Chinese Integrative Medicine,December 2012,Vol.10,No.12
sub-Himalayan and lower hils up to 900m,Assam,
Myanmar,Western Ghats and South India.In
India,it is cultivated in garden and near temples
for its fragrant flowers and handsome foliage[16].
M.rubriflora (Law et R.Z.Zhou,sp.Nov.)is
an endemic species,restricted to Mount Jianfengling in
Hainan Province of China in mountain evergreen
broad-leaved forests at an altitude of 500to 600m.
M.mediocris Dandy grows in the evergreen broad-
leaved forests at an altitude of 400to 1 000min
South-east Guangdong,Guangxi and Hainan(Chi-
na),also in Vietnam and Cambodia[17].Michelia xin-
ningia(Law &R.Z.Zhou sp.Nov.)grows in sand
shale under the evergreen broad-leaved forests at alti-
tude of 1 500min Ziyunshan,Xinning Couty,Hu-
nan Province of China[18].M.multitepalais found
in Fadou Mountain,Xichou Country,Yunnan Prov-
ince of China and also in broad-leaved forests on the
south flank of the mountain range at an altitude of
1 300to 1 500m[19].
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2 Traditional uses of genus Michelia
 Various species of genus Michelia have many
traditional uses.M.champacais used in the treatment
of fever,colic,leprosy,eye disorders,inflammation,
cough rheumatism,gonorrhea,cephalagia,and
gout[20-21].M.alba is used in the prevention of
bronchitis,prostatitis and leucorrhea[22].Most of
the species of Micheliaare useful as garden plants[3].
Michelia species have been used by indigenous
peoples in the treatment of cancer.M.champaca
has been used in India for the treatment of abdominal
tumors and M.hypoleuca and M.offjcinalis for
carcinomatous sores and leukemia respectively in
China[23].The flowers of M.figo were traditionaly
used as cardic tonic and root bark as antidote to
fish poison[13].M.longifolia Blume(M.alba DC)
flowering bud infusion is traditionaly given to the
women of Malay Peninsula for sapremia folowing
miscarriage[24].
3 Chemical constituents
3.1 Steroids Steroids like stigmasterol,β-sitosterol
and stigmasterol have been isolated from the stems of
M.alba Linn[5].β-Sitosterol is also reported in
yelow variety M.sphaerantha[25].Stigmasterol
and 3β-16α-dihydroxy-5-cholestene-21-al were also
isolated from M.champaca Linn[26].
3.2 Terpenoids Two main sesquiterpens,michelenolide
and micheliolide containing lactone ring and two
new inactive sesquiterpene lactones,compressanolide
and dihydroreynosin,were isolated from M.com-
pressa Maxim.The structure of michelenolide and
micheliolide was confirmed by partial synthesis from
parthenolide and the structure of compressanolide
by partial synthesis from dihydroparthenolide[9].A
triterpenoid namely ficaprenol was isolated from
M.alba Linn[7].The major active sesquiterpene
lactones isolated from M.floribunda (Finet &
Gagnep)were costunolide parthenolide and san-
tamarine[14].Terpinen-4-ol was the main terpenoid
isolated from M.foveolata (Mer ex.).About 30
monoterpenes and 26sesquiterpenes were isolated
from the essential oil of M.foveolata[15].Sesquit-
erpene,namely,sphaelactone A,was isolated from
M.sphaerantha[25].A new sesquiterpene,12,13-
diacetoxyl-1,4,6,11-eudesmanetetrol,was ob-
tained from M.yunnanensis[26].Linalool was ex-
tracted from the various parts like flower,leaves
and tender twigs of M.alba Linn.using ethanol
under ultrasonic irradiation.The contents of the
linalool for tender twigs,leaves and budding flowers
were 0.44%,0.21%-0.65%,and 1.63%-4.89%,
respectively.Among other constituents isolated from
M.alba were one monoterpene(α-terpinolene),six
sesquiterpene hydrocarbons(β-elemene,β-caryophylene,
α-humulene,β-selinene,α-selinene,andγ-cadinene)
and four oxygenated sesquiterpenes namely(E)-
nerolidol,α-cadinol,β-bisabolol,and(Z,E)-farnesol
[27].
 The nuclear magnetic resonance(NMR)spectrum
established michelenolide from M.compressa as a
sesquiterpene lactone[18].The typical exomethylene
protons of anα,β-unsaturated-γ-lactone were observed
at 5.63(d,J=2.5Hz)and 6.34(d,J=2.5Hz)
ppm,and this functionality was confirmed by the
observation of a carbonyl absorption at 1 755cm-1 in
the infrared radiation spectrum.Two three-proton
singlets were observed at 1.35and 1.41ppm,
which could be attributed to methyl groups attached to
carbon-bearing oxygen.Two methine signals at
·7331·中西医结合学报2012年12月第10卷第12期 Journal of Chinese Integrative Medicine,December 2012,Vol.10,No.12
2.86(d,J=2.0Hz)and 2.91(d,J=9.0Hz)ppm
were assigned to protons on carbon-bearing oxy-
gen.This information revealed that michelenolide
has two trisubstituted epoxide groups[28].Proton
magnetic resonance spectrum of costunolide compound
showed a doublet of doublets(J=10.0,2.0Hz)
for the C1-proton at 2.73ppm and a singlet for the
epoxide methyl group at 1.16ppm[9].The struc-
ture determination of michampanolide was based
mainly on an extensive NMR investigation where
both 1 H and 13C NMR data showed the position of
the vinylic pair of doublets atδ65.59andδ6.27,and
the presence of a carbonyl carbon atom atδ169.1
made it obvious that it contained aγ-1actone moiety
in a sesquiterpene skeleton.The proton NMR spec-
trum also contained two methyl singlets at 61.32
and 1.27,two hydroxyl signals(s and d)and sig-
nals from two vicinal protons bound to oxygen-bear-
ing carbon atoms,H-5(63.59,dd)and H-6(64.
19,dd).Since the signal of H-5(dd)was shown
by H-H correlations to be coupled to H-6and the
OH-signal at 62.58,C-4must be a quaternary carbon
atom[22].
3.3 Alkaloids Two bioactive bisbenzylisoquinoline
alkaloids namely,magnoline and magnolamine,were
isolated from the leaves of Michelia figo Sprenge[8].
Isoquinoline alkaloid,liriodenine,was isolated
from M.floribunda (Finet &Gagnep)[14].
3.4 Phenols Pressalanin A,a two-functionalised
tetrahydrofuranol,was isolated from the leaves of
M.compressa var.lanyuensis[6].Polyphenolic
compound like galic acid was isolated from the
leaves of M.champaca Linn[29].
3.5 Esters The main constituent having fruity
banana-like aroma isolated from the petals of flow-
ers of M.figo was isobutyl acetate with yield 47.
1%[27].Methyl linoleate and methyl anthranilate were
other esters isolated fromM.champaca Linn[29].
3.6 Aporphines About six aporphines namely,
(-)anonaine,(-)norushinsunine,(-)ushinsunine,
(-)N-formylanonaine,(-)romerine,(-)asimiobine
and two oxoaporphine,liriodinine and oxylopine,
were isolated from the stems of M.alba Linn[27].
3.7 Benzenoids Seven benzenoids like 4-hydroxy-
benzaldehyde,p-anisaldehyde,veratraldehyde,3,
4,5-trimethoxybenzoic acid and 3,4-dimethoxy-
benzoic acid were isolated from M.albaLinn[27].
3.8 Flavonoids A flavonoid glycoside,quercetin,
was isolated from the flowers of M.champacaLinn[30].
3.9 Other constituents Various volatile constituents
likeβ-caryophylene,α-humulene andβ-selinene have
been isolated from the volatile fraction of M.
champaca[31].Ketones like(8z,11z,14z)-8,11,14-
heptadecatriene-2-one was isolated from linolenic
acid obtained from the wax of the flowers of M.
figo Sprenge[32].Chief constituents obtained from
fresh M.alba Linn.flowers includeα-myrcene,
(S)-limonene,(R)-fenchone,linalool,camphor,
caryophylene,and germacrene D[22].Syringin was
isolated from the chloroform extract of M.floribunda
(Finet &Gagnep)[14].Volatile constituents namely,
sabinene (32.4%),terpinen-4-ol (13.7%),β-
oplopenone(5.1%),γ-terpinene(4.7%),(p-cy-
mene(3.9%),α-cadinol(3.2%),δ-cadinene(2.
2%)andα-terpinene(2.1%)have been isolated from
essential oil of M.foveolata Merryl ex.Dandy[15].
4 Biological activities
4.1 Anticancer activity The sesquiterpene lactones
namely michelenolide,micheliolide,parthenolide,
costunolide,santamarine,reynosin and liriodenine i-
solated from M.compressa Maxim.showed cytotoxic
activity[9].A germacranolide,namely,dehydro-
lanuginolide,isolated from the fruits of M.doltsopa
Buch.was identified as the plant constituent responsible
for cytotoxicity in human nasopharynx carcinoma
test system[10].Linalool,isolated from various species
of Michelia,possesses anticancer activity[11].
4.2 Antibacterial activity Sabinene (32.4%)
and terpinen-4-ol(13.7%),the main essential oil
constituents of M.foveolata Mer ex.,exhibited a
significant antibacterial activity against Salmonella
enterica,Staphylococcus epidermidis,Staphylococcus
aureus and Bacillus cereus[15].The antimicrobial
effect of the essential oil containing 14aliphatic
and 16terpenoid compounds from the flowers of
M.figo against Bacillus sabtills,Escherichia coli
and Mucor racemosus was good and their inhibitory
rates were up to 70.36%,60.24%and 65.52%[12].
4.3 Antiplasmodial activity Two bioactive bis-
benzylisoquinoline alkaloids,magnoline and mag-
nolamine,isolated from the leaves of M.figo
Sprenge possessed potent in vitro antimalarial activity
against chloroquine-resistant (K1)and chloroquine-
sensitive(FCR3)strains of Plasmodium falciparum[8].
4.4 Flavouring agents Linalool,a monoterpene
alcohol,occuring naturaly in several aromatic
plants like M.alba Linn.is used in the flavour and
fragrance industry and contributes to the charac-
teristic aroma of a vast number of natural prod-
ucts,such as fruits and spices,as wel as tea and
chocolates[5].
4.5 Other activities Galic acid,apolyphenolic
compound isolated from M.champaca Linn.,pos-
sessed anti-inflammatory,cardioprotective and anti-
oxidant effects and exerted beneficial effects on hu-
man health[26].In addition,M.Champaca Linn.
also possessed antidiabetic[33],anti-ulcer and anti-
inflammatory activities which might be attributed
to alkaloids,flavonoids and terpenoids present in
this plant[27].
5 Conclusion
 About 80species of genus Micheliaare distributed
mainly in south east regions of Asia.Around 94
isolated constituents including steroids,terpenoids,
alkaloids,phenols,esters,etc.have been reported
which are responsible for diferent biological activities
helpful in the treatment of various diseases.Al
these studies revealed that most of these chemical
·8331· 中西医结合学报2012年12月第10卷第12期 Journal of Chinese Integrative Medicine,December 2012,Vol.10,No.12
constituents exhibited significant biological activities.
However,most of the species of Michelia are not
wel explored yet,therefore,it is necessary and
need of the hour to focus on phytochemical and bi-
ological studies of these plants in order to find out
the role of this genus in treatment of other diseases
or disorders.
6 Acknowledgements
 We are grateful for financial support from University
Grant Commission,New Delhi,Government of In-
dia(F.No.39-255/2010).
7 Competing interests
 The authors declare that they have no competing in-
terests.
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含笑属植物所含化学成分与其生物活性的综述
Dinesh Kumar,Sunil Kumar,Seema Taprial,Deepak Kashyap,Ajay Kumar,Om Prakash
Institute of Pharmaceutical Sciences,Kurukshetra University,Kurukshetra 136119,Haryana,India
摘要:属木兰科的含笑属植物大约有80多个种类,它们大都分布在南亚国家。这些植物被当地人用于治疗
各种疾病,如发烧、绞痛、麻风病、眼疾、炎症以及解蝎子毒。从9种含笑属植物中分离出94种化合物,例如
倍半萜烯、类固醇、黄酮类、阿扑啡类、苯酚、酯类、生物碱和苯环型化合物等,它们具有抗菌、抗癌以及抗疟原
虫活性。本文详细地论述了含笑属植物所含化学成分的生物及化学性能。
关键词:含笑属;药理作用;综述
·0431· 中西医结合学报2012年12月第10卷第12期 Journal of Chinese Integrative Medicine,December 2012,Vol.10,No.12