全 文 ：Chemical components of Lactuca and their bioactivites
REN Yu-lin , ZHOU Ya-wei , YE Yun-hua
(The Key Laboratory of Bioorganic Chemistry and Molecular Engineering , College of Chemistry and
Molecular Engineering , Peking University , Beijing 100871 , China)
Key words:lactucin-like guaianolide;zaluzanin C-like guaianolide;sesquiterpene lactones;triterpenes;
Lactuca;compositae
CLC number:R284　　　Document code:A　　　Article ID:0513-4870(2004)11-0954-07
莴苣属植物化学成分和生物活性的研究
任玉琳 , 周亚伟 , 叶蕴华
(北京大学 化学与分子工程学院生物有机和分子工程重点实验室 , 北京 100871)
关键词:莴苣素型愈创木内酯;中美菊素 C 型愈创木内酯;倍半萜内酯;莴苣属;菊科
Received date:2004-01-18.
＊Corresponding author　Tel:86-10-62538501 ,
Fax:86-10-62538495 ,
E-mail:zhouyawe@public.bta.net.cn
　　In the plant kingdom , Compositae , with 1 000
genera and 20 000 species , is a great family.It has two
subfamilies , Carduoideae kitam , with 12 tribes , and
Cichorioideae Kitam , with only 1 tribe , Lactuceae Cass.
In Lactuceae Cass , Lactuca is a great genus , which is
later divided into several genera , such as Cicerbita ,
Mulgedium , Ixeris , Crepidiastrum and Lactuca .Many
species in Lactuca are medicinal herbs as well as wild
vegetables , and scientists focused their research interest
on searching for some promising compounds with high
effectiveness and low toxicity for the benefit of human′s
health.
Sesquiterpene lactone is a kind of very interesting
component in the nature.Many Scientists in the world are
focusing their research interests on this kind of compounds
because of their structural diversities
[ 1] .Later on about
200 compounds were found from Lactuca , including
sesquiterpenoids , triterpenoids , phenolic acids ,
flavonoids , etc. Some pharmacological researches
indicated that the extract and some compounds from
Lactuca showed anticancer , antidiabetic , analgesie
sedative and cholesterol-lowering activities.Here , we
review recent advances in the chemistry and bioactivities
of Lactuca , including all genera separated from it later.
Sesquiterpene lactones(SQLs)from Lactuca
The genus Lactuca , like most members of the tribe
Lactuceae , was characterized by the presence of SQLs ,
mainly guaianolides.There are about 94 compounds
belonging to 6 kinds of SQLs isolated from Lactuca ,
among which 68% are guaianolides , the rest are lactucin-
like guaianolide , zaluzanin C-like guaianolide ,
germacranolide , melampolide and eudesmanolide (Figure
1 , Table 1).Lactucin-like guaianolides , with a ketone at
C-2 , two endocyclic double bond at C-3 (4)and C-1
(10), were isolated from Lactuca , and it can be regarded
as characteristic of Lactuca.Whereas , zaluzanin C-like
guaianolides , with exocyclic double bonds at C-4 (15),
C-11(13)and C-10(14)were isolated from Ixeris , and
it can be characteristic of Ixeris.
Two kinds of macrocyclic SQLs , melampolide and
germacranolide , were isolated from Lactuca. The
melampolides have a ten-member ring and a five-member
ring , with two carbon-carbon double bonds , a cis at C-1
(2)and a trans at C-4(5), an oxidized C-14 forming an
aldehyde or carboxylic group.While the germacranolides
　　　　　　
·954· 药学学报 Acta Pharmaceutica Sinica 2004 , 39(11):954-960
DOI :10.16438/j.0513-4870.2004.11.019
Table 1　Sesquiterpene lactones characterized in members of Lactuca
Name Source Ref. Name Source Ref.
8-deoxylactucin b , i , j , l , k 2 , 12, 19, 25 ,26 , 29 , 35 8-epidesacylcinaropicrin d , e 10 , 14
lactucopicrin＊ b , i , k , l ,m , u 2 , 8 , 12 , 13 , 15 , 19, 20 ,35 picriside B e 10
8-deoxyurospermal A f 3 lactuside C＊ i , l ,m , n 11 , 14, 28 ,29
ixerin A ＊ f 3 jacquinelin b , k , l , m 12 , 18, 19 ,20 ,
25 , 28, 29
ixerin B＊ f 3 tect roside d , n 14
ixerin C＊ f 3 ixerisoside B＊ n 14
ixerin D ＊ a , d , f , n 4 , 14, 30 ixerisoside C＊ n 14
ixerin E＊ f 4 ixerisoside D＊ n 14
ixerin F ＊ f , k , l , m 4 , 20, 21, 25 ,28 , 29 ixerisoside E＊ n 14
ixerin G ＊ f 4 ixerisoside G＊ n 14
ixerin H＊ f 5 ixerisoside H＊ n 14
ixerin I＊ f 5 ixerisoside I＊ n 14
ixerin J＊ f 5 ixerisoside M＊ n 14
ixerin K ＊ f 5 11 β , 13-dihydrolactucopicrin＊ k , l , u 15 , 30
ixerin L＊ f 5 8-acetyl-15β-D-gluco pyranosyllactucin a ,o 16 , 30
ixerin M ＊ d ,g , n 6 , 14 salignoside ＊ k 20
ixerin N ＊ d ,g 6 , 14 zaluzanin C l 21
ixerin O ＊ g 6 9α-hydroxy-11β , 13-dihydrozaluzanin C l 21 , 29
ixerin P ＊ d ,g 6 , 14 dentatin A＊ e 22
ixerin Q ＊ g 6 dentatin B＊ e 22
ixerin R＊ d ,g 6 , 14 dentatin C＊ e 22
ixerin S＊ g 6 dentalactone＊ e 23
ixerin T ＊ g 6 8-epicrepioside G＊ a , d 14 , 24
8-epidesacyl-cynaropicrin- g , n 6 , 14 picriside A l 25
glucoside
macrocliniside A d ,g , k , l ,m , n 6 , 14, 20, 25 ,28 , 29 scorzoside l , t 25 , 34
crepidiaside A＊ h 7 11 β , 13-dihydrolactucin-8-O-acetate q , j 26 , 27
crepidiaside B＊ h ,k , l ,m , t 7 , 20, 25, 28 ,29 , 34 lactucin-8-O-acetate q 26
crepidiaside C＊ h 7 reynosin q 26
crepidiaside D＊ h 7 santamarine q 26
crepidiaside E＊ h 7 cichorioside B l , m 28 , 29
lactucin b , i , k , l ,m , u 8 , 12, 13, 15 ,19 , 20 , 28 , 35 11 β , 13-dihydrolactucin-8-O-p- m 29
methoxyphenylacetate
11β , 13-dihydrolactucin b , i , k , l , u 8 , 12, 18, 19 ,20 , 29 picriside C m 28
3β , 14-dihydro-11β , 13- i 8 sonchuside A l , m 28 , 29
dihydrocostunolide
3β-hydroxy-11β , 13- i 8 11 β , 13-dihydrolactucin-8-O-methacrylate ＊ l 29
dihydroanthospermolide ＊
11 ,13α-dihydrogluco j , m 9 , 28 3β , 14-dihydro-11β , 13-dihydrocostunolide- l 29
zaluzaznin C 3-O-β-D-glucopyranoside
glucozaluzanin C d , j , n 9 , 14 8-deoxyartelin＊ c , l 30
9α-hydroxyzaluzanin C＊ c , j , l 9 , 29, 30 ixerin Z ＊ c 30
9α-hydroxy-11 , 13α- j 9 tataroside ＊ m 31
dihydroglucozaluaznin C＊
dihydrosantamarin j 9 ixerin Y＊ r 32
lactulide A＊ j 9 ixerin X＊ r 33
lactuside A ＊ b , j , k , l , t 9 , 17, 18, 19 ,20 , 25 , 29 , 34 lettucenin A＊ i 35
lactuside B＊ j 9 15-deoxylactucin-8-sulfate＊ i 35
lactucopicriside ＊ j 9 lactucin-15-oxalate ＊ i 35
ixerin U ＊ e 10 8-deoxylactucin-15-oxalate＊ i 35
ixerin V ＊ e 10 15-p-hydroxyphenyl-acetyllactucin-8-sulfate ＊ i 35
ixerin W＊ e 10 jacquinelin glucoside i 35
10α-hydroxy-8-desoxy-10 ,14- e 10 Lactucopicrin-15-oxalate＊ i 35
dihydrodesacylcinaropicrin
＊New compound.a:Ixeris chinensisNAKAI;b:Lactuca serriola L;c:Ixeris sonchifolia Hance;d:Ixeris debilis A.Gray;e:Ixeris dentata
NAKAI;f:Ixeris tamagawaensis Kitam;g:Ixeris stolonifera A.Gray;h:Crepidiastrum keiskeanum NAKAI;i:Lactuca sativa L;j:
Latuca laciniata Makino;k:Lactuca saligna L;l:Lactuca virosa L;m:Lactuca tatarica C.A.Meyer;n:Ixeris repens A.Gray;o:
Cicerbita alpina (L)Wallz;p:Lactuca viminea L;q:Lactuca floridana ;r:Ixeris denticulata f:pinnatipartita ;s:Lactuca quercina;t:
Lactuca perennis;u:Mulgedium tatarica
·955·REN Yu-lin , et al:Chemical components of Lactuca and their bioactivites
contain a ten-member ring and a five-member ring , with
two trans carbon-carbon double bonds , a few carboxylic
groups , but no aldehyde at C-14.Both melampolides and
germacranolides from Lactuca have oxysubstitution at C-
3 , but those from Ixeris have no oxysubstitution at C-3.
Figure 1　Structural skeletons of sesquiterpene lactones
from Lactuca
Ten eudesmanolides were found in Lactuca , nine
with an exocyclic methylene group at C-11 (13) from
Ixeris , one without C-13 exocyclic methylene from
Lactuca.All guaianolides from Lactuca are linked with a
glucose , those from Ixeris have C-3 oxysubstitution , while
those from Lactuca have no C-3 oxysubstitution.
Moreover , there is a guaianolide with a long-conjugated
system isolated from Lactuca sative (lettuce).
Figure 2　Organic acidmoieties linked with sesquiterpene
lactones from Lactuca
Another remarkable characteristic of SQLs from
Lactuca is that many of them are esters , linked with
about 7 kinds of organic acid moieties , such as p-
hydroxyphenylacetyl (a), 2-hydroxy-isovaleryl (b), 2-
hydroxy-3-methyl-n-valeryl(c), methylacrolyl(d), p-
methoxyphenylacetyl (e), p-hydroxy-phenyllactyl (f),
caffyl(g)(Figure 2), among which hydroxyphenylacetyl
is the most common.All these organic acid moieties are
linked at C-8 position of SQLs or at C-4′or C-6′position
of the glucose , which in turn is linked with SQLs at C-3
or C-15 position.Furthermore , there are some oxalates
and sulfates SQLs isolated from Lactuca
[ 35] .
SQLs play an important role in the aspect of
anticancer activity.Park[ 36] found that the extract of
Ixeris sonchifolia H showed antineoplastic action on
Ehrilich carcinoma.Kim[ 37] demonstrated that the extract
of Ixeris dentata had strong antimutagenic effect , both the
chloroform and ethyl acetate fractions were the most
effective part.Later on scientists found that just some
compounds played a crucial role in anticancer effect.
Fukushima et al
[ 3-5]
isolated many SQLs from Ixeris
tamagawaensis , which showed cytotoxic and anticancer
activities.Xu et al[ 27] found that the extract of Lactuca
laciniata showed anticancer action.They also found
dihydrolactucin acetate showed distinguished cytotoxic
activity on the MCF7 and MDA 468 cells.Continuously ,
they convinced that the extract of Ixeris sonchifolia showed
inhibition on murine ascites , hepatic and cervical
carcinoma in vivo , ixerin Z from the herb could inhibit
the growth of human breast cancer MCF 7 and MDA 468
cells lines in vivo
[ 38] .Many herbs of Lactuca are both
medicinal and edible , and it may be promising to find
some anticancer lead compounds. Additionally ,
Kisiel
[ 18 , 21]
reported that the crude extract of Lactuca
virosa and some compounds showed sedative and analgesic
activity ascribed to the presence of the guaianolides.
Tamaki
[ 39]
also exhibited that Lactuca saligna and
Lactuca virosa had been successfully used as virus
resistance into lettuce just because of their high levels of
SQLs.
Triterpenes and other components from
Lactuca
Besides SQLs , triterpene is another main component
of Lactuca .The triterpenes obtained from Lactuca are
mainly pentacyclic triterpenes , belonging to ixerane ,
oleanane , migrated oleanane , ursane , migrated ursane ,
lupane , epilupane and cycloartane , and a few tetracyclic
triterpenes , belonging to dammarane , euphane and
·956· 药学学报 Acta Pharmaceutica Sinica 2004 , 39(11):954-960
epieuphane (Figure 3).A new skeletal triterpene ,
ixerane was firstly isolated from a natural source , and it
was estimated that cyclization of squalene oxide gave the
germanicane cation , whose C-17 and C-18 bond was
cleaved and followed by recyclization to afford ixerane
[ 49] .
Furthermore , there are some other components isolated
from Lactuca , such as phenolic acids , flavonoids ,
alkanes and their derivatives , coumarins , with few
pharmacological studies on them.All triterpenes and other
components except for SQLs are shown in Table 2.
Recent evidences suggested that triterpenes from
Lactuca played an important role in lowering cholesterol
in serum.Young et al[ 56 , 57] reported that the methanol
extract of Ixeris sonchifolia and Lactuca indica caused a
significant lowering of cholesterol in serum of
hypercholesterol rats.Kim et al[ 58] demonstrated that the
diet with triterpenes constituents from Lactuca indica
provoked significant changes of serum lipoprotein
cholesterol metabolism of hypercholesterolenic rats ,
especially some triterpenes , such as β-amyrin , α-
amyrin , lupeol , pseudotaraxasterol , taraxasterol and
germanicol showed great hypocholesterolemic action.
Lim
[ 59]
also found that the powder of Ixeris dentata could
enhance the concentration of HDL-cholesterol and lower
the chylomicron in rats.
In folkmedicines , a few species of Lactuca are used
in the treatment of diabetes , especially type II diabetes ,
but there are only few reports on it.Eskander[ 60] reported
that the suspension of Lactuca virosa showed
hypoglycemic effect , but they did not report which
components played such an effect.It was reported that
some species of Lactuca showed dopamine-β-hydroxylase
inhibitory activity
[ 61] .
We are investigating Mulgedium tatarica for the first
time.The main volatile components of this species are
organic acids
[ 62] .Some lactucin-like guaianolides and
phenolic acids were isolated from this species , and the
crystal X-ray structure of lactucopicrin had been
studied
[ 63] .
Figure 3　Structural skeletons of triterpenes from Lactuca
·957·REN Yu-lin , et al:Chemical components of Lactuca and their bioactivites
Table 2　Compounds except SQLs characterized in members of Lactuca
Name Source Ref. Name Source Ref.
stearyl palmitate a 40 Triacontanoic acid u
stearyl stearate a 40 17-epi lupenyl acetate ＊ a 48 , 50
stearyl arachidate a 40 multiflorenyl acetate a 48 , 50
adenosine c 41 3β-acetoxytaraxaster-20-en-30-al a 48 , 50
α-amyrenyl acetate a , d , e 42 ,48 ,50 dammaradienyl acetate a 48 , 50
β-amyrenyl acetate a , d , e , j 42 ,48 ,50 , 27 tirucalla-7 , 21-dien-3β-yl acetate a 48 , 50
taraxasteryl acetate a , d 42 ,48 ,50 butyrospermyl acetate a 48 , 50
Χ-taraxasteryl acetate a , d , k 42 ,45 ,48 , 50 ixerenol＊ a 49 , 50
lupeyl acetate a , d , e , i , k 42 ,44 ,48 , 26 , 50 taraxerol a 49 , 50
1-hexacosanol c , d , k 42 ,45 ,47 bauerenol a 49 , 50
palmitic acid d 42 tirucalla-7 , 21-dien-3β-ol a 49 , 50
ursolic acid d 42 butyrospermol a 49 , 50
oleanolic acid d 42 cycloartenol a 49 , 50
bauerenyl acetate a , c , e 42 ,43 ,47 , 48 , 50 3β-hydroxytaraxaster-20-en-30-al a 49 , 50
germanicyl acetate a , e , k 42 ,45 ,50 taraxeryl acetate a 50
olean-12-en-3-one a , c , e , j 42 ,47 ,48 , 27 ixerenyl acetate ＊ a , e 42 , 50
olean-18-en-3-one e 42 germanicone a , e 50
lupenone a , e 42 ,50 β-amyrenone a 50
α-amyrin a , e , m 42 ,13 ,49 , 50 taraxasterone a 50
β-amyrin a , e 42 ,49 ,50 Χ- taraxasterone a 50
taraxasterol a , e 42 ,49 ,50 α-amyrenone a 50
luteolin a , c , m , p, t , s 43 ,46 ,38 , 52 , 53 , 56 bauerenone a 50
luteolin-7-O-glucoside a , c , f ,p , r , s 43 ,3 , 46 , 51, 52 ,53 , Olean-13(18)-en-3β-ol a 50
54 ,32 ,56
lupeol a , I ,k 8 , 44 , 49 , 50 multiflorenol a 50
sitosterol a , c , I , j , k 8 , 44 , 47 , 51, 27 isobauerenol a 50
daucosterol i , k 8 , 44 dammaradienol a 50
stigmasterol c , j , k 44 ,47 ,27 24-methylenecycloartenol a 50
chrysoeriol k 44 apigenin-7-O-glucoside a , m 51 , 54
apigenin c , k ,m , p , s 44 ,46 ,38 , 53 stearic acid a 51
7-O-methyl-luteolin k 44 docosanoic acid j 27
methyl-1-p-hydroxyphenyl-α- o 19 benzyl-β-D-glucopyran oside m 28
hydroxyllacticacy-6-hydroxy-15-O-β-D-
glucopyranoside-eudesma-11(13)-12-oate
ixerisoside F ＊ n 14 scopoletin c 38
ixerisoside J＊ n 14 2 ,5-dihydroxycinnamic acid c , r 38 , 52
ixerisoside K ＊ n 14 bis-(2-ethylhexyl)-phthalate c 38
ixerisoside L ＊ n 14 (+)-syringarensinol c 38
ixerisoside N ＊ n 14 p-hydroxybenzaldehyde c 38
methyl-1 , 4 ,6-trihydroxyl-15-O-glucoside- o 16 1 ,4-benzenedimethanol c 38
eudesma-11(13)-12-oate
isoimperatorin o 16 esculetin r 52
oxypeucedanin o 16 ethyl-4-hydroxybenzoate r 52
ostruthol o 16 kaempferol-3-O-β-D-glucopyranoside m , s 53
germanicol a , k 45 ,50 methyl-1-p-hydroxy-2-(2-hydroxyisovaleryl)- o 16
phenyl lacticacyl-6-hydroxy-15-O-β-D-
glucopyranoside-eudesma-11(13)-12-oate
Χ-taraxasterol a , k 45 ,49 ,50 methyl-apigenin-7-O-β-D-glucuronide c 55
nonacosane u methyl-4-hydroxyphenylacetate t 34
eicosanyl octacosate u ethyl-4-hydroxyphenylacetate t 34
quercet in p 46 ethyl-trans-4-hydroxy-cinnamate t 34
quercet in-3-O-glucoside m , p , r 46 ,53 ethyl-trans-3 , 4-dihydroxycinnamate t 34
luteolin-7-O-glucuronide-6″-Me ester p, r 46 ,52 ,32 imperatorin o 16
caffeic acid p 46 methyl caffeiate u
ferulic acid p 46 butanyl p-hydroxyphenylacetate u
chlorogenic acid p 46 methyl 3 ,4-dihydrocaffeoylquinate u
methyl-2-oxo-6α,15-dihydroxy-8α-(p- o 19 methyl 3 ,5-dihydrocaffeoylquinate u
hydroxyphenylacetoxy)-guaia-1(10),
3 , 11-trien-5αH-12-oate ＊
loliolide b 19
＊New compound , a-u:as same as Table 1
·958· 药学学报 Acta Pharmaceutica Sinica 2004 , 39(11):954-960
A great progress has been made over the past
decades in study of biologically active components of
Lactuca , but the results are still unsatisfactory.It is
necessary to find out which kinds of SQLs show high
activity and low toxicity , which components possess
antidiabetic activity , and which triterpenes show the
highest hypocholesterol effect.Such studies will provide
new interests in the developing of some new medicines
from Lactuca for the therapy and prevention of cancer ,
hypercholesterol and diabetes from Lactuca.
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