全 文 ：金鱼藻的化学成分
路小利1 , 2 , 乔 英2 , 张宪民2 , 马柏林1 , 邱明华2
?
( 1 西北农林科技大学生命科学学院 , 陕西 杨陵 712100; 2 中国科学院昆明植物研究所植物化学与
西部植物资源持续利用国家重点实验室 , 云南 昆明 650204)
摘要 : 从金鱼藻 ( CeratophyllumdemersumL .) 全草的乙醇提取物中分离鉴定了其中 7 个 , 分别为 : 苜蓿素-
7- O-β- D-葡萄糖苷 ( 1) , naringenin-7- O-β- D-葡萄糖苷 (2 ) , 七叶内酯 (3) , β-谷甾醇 (4 ) , 7α-羟基-β-谷甾
醇 (5) , 7α-甲氧基-β-谷甾醇 (6) , 十六碳脂肪酸 (7)。化合物 (3) 为首次从金鱼藻中分离得到。
关键词 : 金鱼藻 ; 苜蓿素-7- O-β-D-葡萄糖苷 ; Naringenin-7- O-β- D-葡萄糖苷 ; 七叶内酯
中图分类号 : Q 946 文献标识码 : A 文章编号 : 0253 - 2700 (2007) 02 - 263 - 02
Chemical Constituents from Ceratophyllum
demersum ( Ceratophyllaceae)
LU Xiao-Li
1 , 2
, QIAO Ying
2
, ZHANG Xian-Min
2
, MA Bo-Lin
1
, QIU Ming-Hua
2 *
( 1 Collegeof LifeScience of Northwest Sci-Tech University of Agricultural and Forestry, Yangling 712100 , China;
2 TheState Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute
of Botany, Chinese Academy of Sciences, Kunming 650204 , China)
Abstract: In this paper, we represent seven compounds [ tricin-7-O-β- D-glucoside (1 ) , naringenin-7-O-β- D-glucoside
( 2) , esculetin (3) , β-sitosterol (4) , 7α-hydroxyl-β-sitosterol (5) , 7α-methoxyl-β-sitosterol (6) and palmitic acid (7) ] .
All compounds were isolated from Ceratophyllum demersum L . which was collected from Lijang . We compare themwith
compounds isolated formthematerial collected fromKunming by TLC . The results show that the types of main secondary
metabolite in CeratophyllumdemersumL . in Yunnan are similar .
Key words: Ceratophyllumdemersum; Tricin-7- O-β- D-glucoside; Naringenin-7- O-β-D-glucoside; Esculetin
CeratophyllumdemersumL . ( Ceratophyllaceae) ,
is a kind of perennial hydrophily plant and widely dis-
tributed throughout ponds and rivers in China . Usually
it was used as goldfish feed, as well as folk medicine
for the treatments of internal injury and haematemesis
(Wu et al . 2003) . Foreign scholars have already iso-
lated two compounds of flavonoid and seven kinds of
Phytosterol ( Bankova et al . 1995 ) ; however, the
chemical constituents of Ceratophyllum demersum L .
fromChina have not been analysed . We try to system-
atically study on chemical constituentsof theplants and
provide accessorial evidence to determine the systemati-
cal position of Ceratophyllaceae . In the paper, the
chemical structures of seven compounds from above
mentioned plant would be reported .
Experimental
General Melting points were measured on a WC-1 micro
melting points apparatus and are uncorrected . 1 H NMR , 13 C
NMR and 2D-NMR spectra were recorded on a Bruker AM-400
MHz and a DRX-500 spectrometer with TMS as internal stan-
dard . FAB-MS: Autospec-3000 spectrometer ( in m?z) ; Silica
gel (200 - 300mesh) was produced by Qingdao Marine Chemical
Company . Rp-18 (40 - 60μ, Merck) . Sephadex LH-20 (Amer-
shamPharmacia Biotech AB) .
Plant Material The Ceratophyllum demersum L . was
collected inLijiang, Yunnan Province, P . R . C . in May 2005 .
云 南 植 物 研 究 2007 , 29 (2) : 263～264
Acta Botanica Yunnanica

? ?Foundation item: XiBuZhiGuang Program of Chinese Academy of Sciences for financial support .
Corresponding author, Tel : + 86 - 871 - 5223327; Fax: + 86 - 871 - 5223255; E-mail : mhchiu@ mail . kib. ac. cn
Received date: 2006 - 07 - 11; Accepted date: 2006 - 08 - 10 接受发表
作者简介 : 路小利 (1982 - ) 女 , 在读硕士研究生 , 主要从事植物化学研究。
The plant material was identified by Dr . Li Xiaoxian (Kunming
Institute of Botany, the Chinese Academy of Sciences) , and a
voucher specimen was deposited at the Laboratoryof Phytochem-
istry, Kunming Instituteof Botany .
Extraction and Isolation Dried chipped Ceratophyllum
demersumL . (5 kg) was extracted with EtOH . The extract was
filtered, concentrated in vacuo to a suitable volume, suspended
in water, andthen successively partitionedwith PetroleumEther,
CHCl3 , and EtOAc, respectively . These three extractswere re-
spectively concentrated in vacuo to afford residues of Petroleum
Ether (62 g) , residues of CHCl3 (25 g) and residues of EtOAc
(11 g) .
The EtOAc portion was subjected repeatedly to silica gel
chromatography and stepwisely eluted with CHCl3 -Me2 CO (from
CHCl3 to CHCl3 -Me2 CO 1∶1) to yield tricin-7- O-β- D-glucoside
(1) ( 10 mg) , Naringenin-7-O-β- D-glucoside ( 2) (7 mg) and
esculetin (3) (7 mg) , respectively .
The CHCl3 portion was subjected repeatedly to silica gel
chromatography and stepwisely eluted with CHCl3 -Me2 CO (from
CHCl3 to CHCl3 -Me2 CO 1∶1) toyieldβ-sitosterol (4) (10 mg) ,
7α-hydroxyl-β-sitosterol ( 5 ) ( 9 mg) , 7α-methoxyl-β-sitosterol
(6) ( 7 mg) , palmitic acid (7 ) (12 mg) , respectively .
Structural Identification
Tricin-7- O-β-D-glucoside ( 1 ) , C23 H24 O12 , yellow pow-
der . mp 260 .5 - 261℃ (MeOH) . 1 H NMR (400 MHz, DM-
SO) : 6 . 44 ( 1H , s, H - 3) , 6 . 95 ( 1H, s, H - 6 ) , 7 . 04
(1H , s, H - 8) , 7. 34 (2H, s, H - 2′, 6′) , 3 . 87 (6H , s,
OMe) , 4. 69 (1H , d, H - 1″) , 3 . 72 - 3 .15 ( 6H, m, H -
2″, 3″, 4″, 5″, 6″) . 13 C NMR ( 125 MHz, DMSO) : 164 .3
(C - 2) , 103 .8 (C - 3) , 182 .1 (C - 4) , 161 .1 ( C - 5) , 99 .6
(C - 6) , 163 .1 (C - 7) , 95.4 ( C - 8) , 105.5 ( C - 9) , 157 .0
(C - 10 ) , 120.3 ( C - 1′) , 104 .6 (C - 2′, 6′) , 148.3 ( C -
3′, 5′) , 140 .2 ( C - 4′) , 100 .2 ( C - 1″) , 73 .2 ( C - 2″) ,
76 .5 ( C - 3″) , 69 .8 ( C - 4″) , 77 .4 ( C - 5″) , 60 .8 (C - 6″) ,
56 .5 (3′, 5′-OMe) . (Ramachander G . et al . 1978) .
Naringenin-7- O-β- D-glucoside (2) , C21 H22 O10 , mp 225℃ .
1
H NMR (400 MHz, CD3OD) : 2 .72 (1H , H - 3 , d, J = 12 .3
Hz) , 3. 13 (1H, H - 3 , d, J = 12.3 Hz) , 3 . 15 - 3 .50 (4H,
m, H - 2″, 3″, 4″, 5″) , 3 . 62 ( 1H , H - 6″, d, J = 11 .9
Hz) , 3. 70 (1H , H - 6″, d, J = 11 .9 Hz) , 5 . 40 (1H, H -
2 , brs) , 6 . 18 ( 1H , H - 8 , s) , 6 .20 ( 1H, H - 6 , s) ,
4 . 96 (1H , H - 1″, d, J = 4 .3 Hz) , 6 . 80 (2H, H - 3′and
H - 5′, d, J = 7 .5 Hz) , 7 . 31 (2H, H - 2′and H - 4′d, J
= 7 .5 Hz) ; 13 C NMR ( 125 MHz, CD3 OD) : 80.6 ( C - 2 ) ,
42 .4 (C - 3) , 198 .5 (C - 4 ) , 167.0 ( C - 5) , 98 .1 ( C - 6 ) ,
164 .6 (C - 7 ) , 96 .9 (C - 8 ) , 164 .0 (C - 9 ) , 116 .4 ( C -
10) , 130 .9 ( C - 1′) , 129 .1 ( C - 2′, 6′) , 116 .4 ( C - 3′,
5′) , 159 .1 ( C - 4′) , 101 .3 ( C - 1″) , 74 .7 (C - 2″) , 78 .3
(C - 3″) , 71 .2 (C - 4″) , 77 .9 (C - 5″) , 62 .4 (C - 6″) .
Esculetin ( 3) , C9 H6 O4 , yellow crystal, mp 285 - 286℃
(EtOH) . 1 H NMR ( 400 MHz, DMSO) : 6. 11 (1H, d, J =
9 .5 Hz, H - 3) , 7 .77 ( d, J = 9 .5 Hz, H - 4 ) , 6 . 99 (1H,
s, H - 5) , 6. 76 ( 1H , s, H - 8) . 13 C NMR (125 MHz, DM-
SO) : 161.5 (C - 2) , 112 .5 (C - 3) , 144 .7 (C - 4 ) , 112 .9 (C
- 5) , 143 .9 ( C- 6) , 151 .4 (C - 7) , 103 .4 (C - 8) , 149 .8 (C
- 9) , 111 .8 ( C- 10) . (Cussans N . J . et al . 1975) .
Discussion
Seven known compounds whichwere isolated from
CeratophyllumdemersumL . collected in LijangCounty
of Yunnan province, were compared them with the
MeOH extracts of Ceratophyllum demersumL . collect-
ed in Kunming by TLC . The results shown that the
compounds of main secondary metabolite from Cerato-
phyllum demersum L . collected in different place of
Yunnan were very similar .
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