全 文 ：Journa l o f Chine se Pharm aceu tical Sciences 2006, 15(1):1-5 1　
Sulfated Sterols Isolated from StarfishAsterias amurensis Lutken
LIU Hong-we i1, 2 , LI Jian-kuan2, 3 , WANG N ai-li1 , YAO X in-sheng2, 3* , and CA IGuo-p ing1
(1. L ife ScienceD ivision , Graduate School at Shenzhen, Tsinghua University, Shenzhen 518055 , China;
2.Key Laboratory for Research and Developm ent of New D rugs, Shenzhen 518055 , Ch ina;
3. College of T rad itiona l ChineseM ateriaM edica , Shenyang Pharmaceutica lUniversity, Shenyang 110016 , Ch ina)
Received date:2005-10-25.
Foundation item:Ch ina Postdoctoral Science Foundation (2005037065)
*C orresponding au thor:Tel 86-755-26036132,
Fax 86-755-26036131,
E-m ail yaox insheng@ vip. tom. com
Abstract:Ami 　To study the chem ical constituents of starfish Asterias amurensis. Methods　The
constituents w ere separated and purified by different chrom atog raphicme thods, and their structu resw e re
elucidated by M S and NMR. Results　S ix compounds w ere iso la ted from Asterias amurensis Lu tken.
The ir structu res we re identified as 3β-O-su lfated-cho lest-5-en sodium sa lt (1), 3β-O-sulfated-6α-ol-
pregn-9(11)-en-20-one sodium sa lt (2), 3β-O-su lfa ted-6α-o l-cho lest-9(11)-en-23-one sodium salt
(3), 3β-O-sulfated-6α, 20β-diol-cholest-9(11)-en-23-one sod ium salt (4), 3β-O-sulfated-6α-ol-
cho lesta-9(11), 20(22)-d ien-23-one sodium salt(5), and 3β-O-sulfated-6α-o l-e rgost-9(11)-en-23-
one sodium salt(6). Conclusion　Compounds 1 - 6were ob tained from this species for the first time.
Key words:Asterias amurensis;chem ical constituents;sulfated ste ro ls
CLC number:R284. 1;R284. 2　Docum ent code:A 　Article ID:1003-1057(2006)1-001-05
In troduction
S teroida l g ly cosides are the predom inan t metabo-
lites of starfish and are responsible fo r their genera l tox-
icity
[ 1, 2]
. A ccord ing to the chem ica l structures, they
are div ided into threema in groups:aste rosaponins, cy-
clic steroidal g lycosides, and g lycosides of po lyhydrox-
y la ted steroids. M embers of the first g roup are usually
su lfated ste ro idal penta-or hexag lycosides having a
△9(11)-3β , 6αdioxy steroida l ag ly con w ith a su lfa te
group attached a tC-3 and the o ligosaccharidemo ie ty at
C-6[ 3] . These saponinsw ere repo rted to exhibit various
biological ac tiv ities, including cy to toxic, hemoly tic,
antibacte ria l, antiviral, and antifungal e ffec ts[ 4] . S tar-
fishA. amurensis has been used as traditionalmedicine
for the treatment o f stomach disease fo r a long time. It
is also eaten by the fishe rmen living in sou th China. It
is believed to be a wholesome food. Previous stud ies
revea led an an titumo r acidic po ly saccharide (NRP-1)
from the sta rfish A. amurensis
[ 5]
. Up to now , the re is
no o ther repo rt about chem ical constituents of i.t W e
studied the chem ica l constituents of it in a bid to c larify
the substances appropria te fo r its traditiona l uses, and
succeeded in iso lating six su lfated sterols. In this pa-
pe r, we describe the iso lation and structura ldeterm ina-
tion o f the se compounds.
Results and D iscussion
Six su lfated stero ls we re iso lated and purified by
differen t chrom atog raphic me thods from starfish A.
amurensis, and their structures w ere e lucidated by M S
and NMR spec troscopic data comparied w ith relevan t
data in litera ture
[ 6 -13]
. Compounds 1 - 5 were ob-
tained from this species fo r the first time. Compound 1
was synthesized in 1960s, and de tected in the rat kid-
ney and liver andAstrocladus con iferus
[ 6-8]
. C ompounds
2 and 4 were repo rted to be from Far East starfish Le-
thasterias nanimensis
[ 9] , compound 3 was from starfish
Aphelasterias japonica and Lysastrosoma an thostic-
ta
[ 10, 11] , compound 5 was found in the starfish Acan-
thaster planci
[ 12] , and compound 6 was from A. amu-
rensis versicolor Sladen
[ 13]
. C ompound 1 has potent an-
ticancer activities against He la (ce rv ix adenocarcino-
2　 Journal o f Chinese Pharm aceu tical Sciences 2006, 15(1):1-5
ma), Cne (nasopharyngeal carcinoma), and Bgc
(gastric carcinom a)[ 6] . Sulfated stero ls from marine
orig in have been found to possess inhibitory effects on
thym id ine phosphory lase andH IV v irus
[ 14, 15]
.
Experimen tal
Apparatus and reagents
M elting po ints w ere determ ined on a Yanaco MP-
S3 m icrome lting po in t appara tus, and w ere uncorrec t-
ed. Op tical ro tationsw eremeasured by using a P-1020
digita l po larimete r (Jasco Corpora tion). FAB-MS and
HR-MS were obta ined w ith a Jeo l JMS-DX302 spec-
tromete r. ESI-MS was reco rded on a B ruker E squire
2000mass spectrome ter. IR spectra w ere recorded on
Shimadzu FT /IR-8400 spectrome ter. 1H and 13C
NMR, a long w ith 2D NMR spectra w ere ob tained on a
B rukerAV-400 (400 MH z for 1H , 100 MH z for 13 C
NMR spectrome ter, using TM S as an interna l stand-
ard. TLC w as ca rried out on silica ge l 60F254 and the
spotsw ere v isualized by spraying w ith 10%H 2SO 4 and
heating. LH-20 (Amersham B io sciences) and ODS
(Lobar, 40 - 63 μm , Merck)we re used fo r co lumn
chromatography. Prepa ra tive HPLC was pe rfo rm ed u-
sing an ODS column (C18 , 250 mm ×20 mm , Shi-
madzu Pak;de tec to r:RID).
An ima lm aterial
The starfish specimens w ere co llec ted in August
2004 (The No rth Sea of Ch ina, Guangxi) and iden ti-
fied by M r. W ang Yu-sheng (Research Institute of
Traditional ChineseM ed icine, Guangdong).
Extraction and isolation
G round starfish (5 kg)were subjected to exhaus-
tive extrac tion w ith methano l by ref lux ing(10 L ×3).
The extrac ts we re concentrated in vacuo. The residue
w as suspended in w a ter (4 L), and partitioned w ith
ch lo ro form and w a te r-sa tura ted n-bu tano l (350 g).
The butanol so lub le partw as app lied to silica gel co l-
umn chrom atog raph (8×35 cm) e lu ted w ith chloro-
fo rm-me thano l(100∶0, 98∶2, 97∶3, 95∶5, 90∶10,
80∶20, 70∶30, 60∶40, 0∶100) in a gradientmanne r to
give 15 fractions. Fractions 8 and 9 e luted w ith chloro-
fo rm-me thano l (80∶20, 70∶30), respec tively, were
found to be rich in stero ida l constituents. F raction 8
(13. 3 g)was further ch roma tog raphed onODS co lumn
w ith methano l-water as eluents to afford 13 subfrac-
tions. C ompound 1 (29. 0mg)was ob tained from sub-
frac tion 11 by recry sta llization w ith methano.l Subfrac-
tion 2 was passed through Sephadex LH-20 co lumn
(CHC l3∶CH 3OH , 1∶1) and finally purified by prepar-
a tive HPLC (MeOH∶H2O , 55∶45) to g ive 2 (84. 0
mg). C ompound 4 (8. 7 mg)was obtained from sub-
frac tion 3 by the same w ay as tha t of subfraction 2.
Sub fraction 4 w as first passed through Sephadex LH-20
co lumn CHC l3∶CH 3OH , 1∶1) and then sub jec ted to
HPLC purification (MeOH∶H2O , 57∶43) to afford 6
(5. 7 mg). Subfractions 5 and 8 w ere purified by pre-
parativeHPLC (M eOH∶H2O , 60∶40 and 78∶22) to af-
ford compounds 3 (26. 7 mg) and 5 (7. 1 mg), re-
spectively.
Iden tification
Compound 1　White powder, [ α] 25D - 11. 7°(c
1. 0, methano l). Positive ESI-MS showed [M +N a] + ion
peak atm /z 511, nega tive ESI-MS gave [M-Na] - ion
peak atm /z 465. Themo lecularw eightw as determ ined to
be 488, and the mo lecular formula o f 1was deduced as
C27H45O4SNa in combination w ith
1
H and
13
C NMR data.
1
H NMR (CD3OD)∶0. 71 (3H , s, H-18), 0. 87 (6H ,
d, J =6. 8Hz, H-26, 27), 0. 95 (d, J =6. 8Hz, H-
21), 1. 02 (3H , s, H-19), 4. 11 (1H , m , H-3), 5. 38
(1H , m , H-6). 13 C NMR (CD3OD) data are given in
Table 2. A ll data were identical w ith those of 3β-O-sul-
fated-cho lest-5-en sodium salt[ 6] .
Compound 2 　White pow de r, [ α] 25D +47. 3°
(c 1. 0, me thano l ). Positive ESI-MS show ed [M +
Na] + ion peak a tm /z 457, negative ESI-MS gave [M-
Na] - ion peak a tm /z 411. The molecula r w eigh t
w as de te rm ined to be 434, and the mo lecular formu la o f
2was deduced as C21H31O 6SNa in comb ination w ith
1
H
and
13
C NMR da ta. A ll NMR signals we re assigned
on the basis o f
1
H-1H COSY , HMQC , and HMBC
spectra analysis. For
1
H and
13
C NMR (C5D5N), see
Tab le s 1 and 2. A ll da ta w ere iden tical w ith tho se o f
3β-O-sulfated-6α-o l-pregn-9(11) -en-20-one sodium
sa lt
[ 9]
.
LIU H ong-w ei, et al:Su lfated S te ro ls Iso lated from Starfish Asterias am urensis Lutken 3　
F igure 1　 Struc tures of com pounds 1 -6 isolated from Asterias amurensis
Tab le 1　1H NMR data for com pounds 2, 3, and 4(400MHz)
Num ber 　　　2a δH(J inH z) 　　　 3b δH (J in H z) 　　　 4a δH (J in H z)
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
　　1. 34, 1. 58 (m)c
1. 81, 2. 46 (m)
4. 87 (m)
1. 68 (m), 3. 33 (br. d, 8. 0 H z)
1. 36 (m)
3. 80 (m)
1. 20, 2. 38 (m)
2. 04 (m)
5. 25 (br. s)
2. 20 (m)
1. 34 (m)
1. 58, 2. 32 (m)
1. 17, 1. 73 (m)
2. 56 ( t, 9. 2 H z)
0. 56 (s)
0. 88 (s)
2. 14 (s)
　　 1. 42, 1. 73 (m)
1. 63, 2. 13 (m)
4. 20 (m)
1. 30, 2. 46 (m)
1. 11 (m)
3. 51 (m)
0. 93, 2. 15 (m)
2. 13 (m)
5. 33 (br. d, 5. 6 H z)
2. 00, 2. 15 (m)
1. 30 (m)
1. 23, 1. 81 (m)
1. 29, 1. 85 (m)
1. 27 (m)
0. 66 (s)
0. 97 (s)
2. 0 (m)
0. 89 (d, 6. 4 H z)
2. 17, 2. 49 (m)
2. 30 (d, 7. 2 H z)
2. 08 (m)
0. 91 (d, 7. 2 H z)
0. 91 (d, 7. 2 H z)
　　1. 35, 1. 64 (m)
1. 86, 2. 50 (m)
4. 88 (m)
1. 72 (m), 3. 39 (d, 10. 4 H z)
1. 38 (m)
3. 80 (m)
1. 25, 2. 47 (m)
2. 13 (m)
5. 23 (b r. d, 5. 6H z)
2. 13, 2. 33 (m)
1. 34 (m)
1. 78, 2. 20 (m)
1. 28, 1. 80 (m)
1. 73 (m)
1. 02 (s)
0. 94 (s)
1. 59 (d, 6. 4 H z)
2. 63 (d, 14. 8), 2. 80(d, 14. 8 H z)
2. 40 (m)
2. 19 (m)
0. 87 (d, 2. 0 H z)
0. 89 (d, 2. 0 H z)
aM easu red in pyrid in e-d5;bM esured inM eOH-d 4. cS ignalsw ere assigned by in terp retation of 2D NM R data
　　Compound 3　W hite pow der, [ α] 25D +28. 8°
(c 1.0 , methano l). Positive ESI-MS show ed [M +
N a] + ion peak a tm /z 541, nega tive ESI-MS gave
[M-Na] - ion peak a tm /z 495. The mo lecu la rw eight
w as de te rm ined to be 518 , and the mo lecu lar formu la
of 3 was deduced as C27H43O 6SNa in combination w ith
1
H and
13
C NMR data. A ll NMR signals w ere as-
signed on the basis of
1
H-1H COSY , HMQC , and
HMBC spectra ana ly sis. For
1
H and
13
C NMR
(CD3OD), see Tables 1 and 2. A ll data were identical
w ith those of 3β-O-sulfated-6α-ol-cholest-9 (11)-en-23-
one sodium salt
[ 10, 11]
.
4　 Journal o f Chinese Pharm aceu tical Sciences 2006, 15(1):1-5
Tab le 2　13C NMR data for compounds 1 - 6 (400MH z)
Num ber 　　　 1a 　　　 2b 　　　 3a 　　　 4b 　　　 5a 　　　 6a
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
　　 37. 7
30. 0
79. 8
38. 4
141. 6
123. 3
33. 2
41. 1
51. 6
37. 3
25. 0
40. 7
43. 5
58. 1
22. 7
25. 3
57. 6
12. 3
19. 3
37. 1
19. 8
37. 3
29. 3
40. 4
29. 1
22. 9
23. 1
　　36. 1
29. 3
78. 2
31. 0
50. 2
68. 4
43. 1
35. 8
146. 7
38. 4
115. 9
40. 7
42. 6
53. 7
23. 2
25. 7
63. 5
13. 2
19. 3
208. 6
31. 1
　　 36. 9
29. 5
79. 7
31. 1
51. 1
69. 7
42. 8
37. 0
146. 8
39. 1
117. 8
43. 3
42. 3
54. 9
26. 2
29. 4
57. 4
12. 0
19. 6
33. 5
19. 9
51. 2
213. 8
53. 3
25. 6
22. 8
22. 9
　　36. 1
29. 4
77. 9
31. 1
50. 6
68. 9
43. 3
35. 6
146. 1
38. 3
116. 4
42. 5
41. 6
54. 1
23. 3
25. 2
59. 6
13. 5
19. 3
73. 7
27. 1
54. 9
211. 6
54. 0
24. 3
22. 5
22. 6
　　37. 0
29. 6
79. 6
31. 1
51. 2
69. 8
42. 9
36. 9
146. 9
39. 2
117. 7
43. 3
42. 3
55. 0
23. 3
26. 3
57. 8
13. 5
20. 8
157. 0
27. 6
125. 3
204. 0
52. 4
34. 4
19. 6
19. 8
　　37. 0
29. 6
79. 7
31. 2
51. 2
69. 8
43. 2
36. 6
146. 7
39. 2
117. 8
43. 4
42. 5
54. 9
23. 8
25. 9
60. 0
13. 6
19. 5
75. 2
26. 7
55. 1
217. 9
54. 4
31. 1
18. 8
21. 7
12. 4
aM esured inM eOH-d4;bM easured in pyrid ine-d 5
　　Compound 4　White powder, [ α] 25D - 2. 2°(c
1.0, me thano l). Positive ES I-MS show ed [M +Na] +
ion peak atm /z 557, negative ES I-MS gave [M -
N a] - ion peak atm /z 511. The molecula rwe igh tw as
dete rm ined to be 534, and the molecu la r formula o f 4
was deduced as C27H43O 7SN a in comb ination w ith
1
H
and
13
C NMR data. A llNMR signalsw ere assigned on
the basis of
1
H-1H COSY, HMQC , andHMBC spectra
analysis. For
1
H and
13
C NMR (C5D 5N), see Tab les
1 and 2. A ll data w ere iden tical w ith those o f 3β-O-
su lfated-6α, 20β-d iol-cho lest-9 (11)-en-23-one sodi-
um sa lt
[ 9]
.
Compound 5　W hite powder, [ α] 25D +7. 2°(c
0.5, me thano l). Positive ES I-MS show ed [M +Na] +
ion peak atm /z 539, negative ES I-MS gave [M-Na] -
ion peak atm /z 493. The mo lecu larw eigh tw as de te r-
m ined to be 516, and the mo lecu lar formula o f 5 was
deduced as C27H41O 6SN a in combination w ith
1
H and
13
C NMR da ta.
1
H NMR (CD3OD):0. 66 (3H , s,
H-18), 0. 90 (3H , d, J = 7. 0 H z, H-26), 1. 88
(3H , d, J = 7. 0 Hz, H-27), 2. 11 (d, J =6. 8
H z, H-21), 0. 98 (3H , s, H-19), 3. 50 (1H , m ,
H-6), 4. 20 (1H , m , H-3), 5. 33 (1H , br d, J =
6. 0 H z, H-11), 6. 16 (1H , br. s, H-22). Fo r 13 C
NMR (CD3OD) see Tab le 2. A ll data we re identica l
w ith those o f 3β-O-sulfa ted-6α-o l-cho lesta-9 (11), 20
(22)-d ien-23-one sodium salt[ 12] .
Compound 6　White powder, [ α] 25D -14. 2°(c
0.5, me thanol). Positive ESI-MS show ed [M +N a] +
ion peak atm /z 571, nega tive ESI-MS gave [M-N a] -
ion peak atm /z 525. The molecula rw e ightw as deter-
mined to be 548, and the mo lecu lar formula o f 6 was
deduced as C27H43O6 SNa in combina tion w ith
1
H and
13
C NMR data.
1
H NMR (CD3OD):0. 78 (3H , s,
H-18), 0. 83 (3H , d, J =6. 8 Hz, H-26), 0. 92
(3H , d, J =6. 8 Hz, H-27), 0. 95 (3H , d, J =
6. 8 Hz, H-27), 0. 98 (3H , s, H-19), 1. 34 (d,
J =6. 8H z, H-21), 2. 59 (1H , d, J =16. 0 H z,
H-22), 2. 70 (1H , d , J =16. 0 H z, H-22), 3. 50
(1H , m , H-6), 4. 18 (1H , m , H-3), 5. 33 (1H , br
d, J =6. 0 Hz , H-11), 6. 16 (1H , br. s, H-22).
For
13
C NMR (CD3OD) see Table 2. A ll data w ere i-
dentica l w ith those of 3β-O-sulfated-6α-o l-e rgost-9
(11)-en-23-one sodium salt[ 13] .
A cknow ledgemen ts
W e appreciated the help ofM iss Zhang Xue and
LIU H ong-w ei, et al:Su lfated S te ro ls Iso lated from Starfish Asterias am urensis Lutken 5　
M r. G aoHao inmeasuring theNMR and ESI-MS data.
Thew o rk w as supported by China Postdoc to ral Science
Foundation.
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多棘海盘车硫酸甾醇类化学成分研究
刘宏伟 1, 2 , 李建宽2 , 3 , 王乃利1 , 姚新生 2, 3 , 蔡国平 1
(1. 清华大学深圳研究院 生命学部 , 广东 深圳 518055;
2深圳市创新药物重点研究室 , 广东 深圳 518055;
3. 沈阳药科大学 中药学院 , 辽宁 沈阳 110016)
摘要:目的　对多棘海盘车(Asterias am urensis)的化学成分进行研究。 方法　用色谱法分离 , 并用各种波谱法对化合物
的结构进行鉴定。结果　从多棘海盘车甲醇提取物中分离鉴定了 6个化合物 , 其结构分别为:3β-O-sulfated-cho lest-5-en
sodium salt(1), 3β-O-su lfated-6α-o l-pregn-9 (11)-en-20-one sodium sa lt(2), 3β-O-sulfa ted-6α-o l-cho lest-9 (11)-en-23-one so-
dium salt(3), 3β-O-sulfa ted-6α, 20β-dio l-cho lest-9 (11)-en-23-one sod ium sa lt (4), 3β-O-sulfa ted-6α-ol-cho lesta-9 (11), 20
(22)-dien-23-one sodium salt(5), 3β-O-sulfated-6α-o l-ergo st-9(11)-en-23-one sodium sa lt(6).结论　以上化合物均为首次从
该种海星中获得。
关键词:多棘海盘车;化学成分;硫酸甾醇