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J. Nat. Prod. 2004, 67, 1650-1653
Steroids and Sesquiterpenoids from the Soft Corals Dendronephthya gigantea and
Lemnalia cervicorni
Chang-Yih Duh, Ali A. H. El-Gamal, Pei-Ying Song, Shang-Kwei Wang and Chang-Feng Dai
Department of Marine Resources, National Sun Yat-sen University, Kaohsiung, Taiwan ,
Department of Microbiology, Kaohsiung Medical University, Kaohsiung, Taiwan ,
and Institute of Oceanography, National Taiwan University,Taipei, Taiwan, Republic of China
A Photo of Dendronephthya soft coral
Abstract
One new cytotoxic steroid, dendronesterone A (1), two new steroids, dendronesterones B and C (2 and 3), and a known steroid (4) were isolated from the methylene chloride solubles of the Formosan soft coral Dendronephthya gigantea. Two cytotoxic ylangene-type sesquiterpenoids, lemnalol (5) and the new compound cervicol (6), as well as two ylangene-type sesquiterpenoids, isolemnalol (7) (a new compound) and 4-oxo-R-ylangene (8), were isolated from the methylene chloride solubles of the Formosan soft coral Lemnalia cervicorni. Their structures were elucidated by 1D and 2D NMR spectral analysis, and their cytotoxicity against selected cancer cells was measured in vitro.
Aim of StudyAim of Study
Aim of study is focused on the separation of bioactive substances from marine organisms, the Formosan soft corals Lemnalia cervicorni (Nephtheidae) and Dendronephthya gigantea (Nephtheidae) were studied because the CH2Cl2 extracts showed significant cytotoxicity to A549 (human lung adenocarcinoma), HT-29 (human colon adenocarcinoma), and P-388 (mouse lymphocytic leukemia) cell cultures as determined by standard procedures. Bioassay-guided fractionation of CH2Cl2 extracts of D. gigantea resulted in the isolation of one new cytotoxic steroid, dendronesterone A (1), two new steroids, dendronesterones B and C (2 and 3), and a known steroid (4).
Bioassay-guided fractionation of CH2Cl2
extracts of L. cervicorni resulted in the isolation of two cytotoxic ylangene-type sesquiterpenoids, lemnalol (5) and a new compound, cervicol (6), as well as two ylangene-type sesquiterpenoids, isolemnalol (7) (a new compound) and 4-oxo-R-ylangene (8).
Aim of StudyAim of Study
Extraction, Separation and purification Scheme for Extraction, Separation and purification Scheme for soft coral soft coral Dendronephthya giganteaDendronephthya gigantea
Bodies of the soft coral Dendronephthya gigantea were freeze-dried to give 1.88 Kg of a solid
extract with CH2Cl2 (4lX3), conc in vacum
14.2 g of CH2Cl2 extract
CC, Sil. gel using n-hex. and n-hex. -EtOAc gradient, followed byEtOAc-MeOH% of EtOAc /n-hex
10% 17%
1*,2* 3*,4*
HPLC (Rp-18), MeOH-H2O (93:7)
HPLC (Rp-18), MeOH-H2O (93:7)
Sub Fr.. A Sub Fr.. B
* ED50 9.84, >100, >100, 8.93 g/ml respectively against P-388 cytotoxic cell line* ED50 >100, >100 >100 and 9.03 g/ml respectively against HT-29 cell line
12
34
5
67
89
10
1112
13
14
15
16
17
18
21
23
28
25
27
30
20
22
2619
24
O
Dendronesterones B (2)
12
34
5
67
89
10
1112
13
14
15
16
17
18
21
23 25
27
30
20
22
2619
24
O
Dendronesterones A (1)
12
3
45
67
8
9
10
1112
13
14
15
16
17
18
21
23 25
27
30
20
22
2619
24
O
Dendronesterones C (3)
12
34
5
67
8
9
10
1112
13
14
15
16
17
18
21
23 25
27
30
20
22
2619
24
O
(4)
O
Compounds Isolated from Dendronephthya gigantea
12
34
5
67
89
10
1112
13
14
15
16
17
18
21
23 25
27
20
22
2619
24
O
1
1H NMR of Dendronesterone A (1)
2 22,23
182627
19
21
COSY spectrum Dendronesterone A (1)
12
34
5
67
89
10
1112
13
14
15
16
17
18
21
23 25
27
20
22
2619
24
O
1 22223
1
2
22,23
1826 27
1921
(HSQC Dendronesterone A (1
12
34
5
67
89
10
1112
13
14
15
16
17
18
21
23 25
27
20
22
2619
24
O
1 22223
1
22
232
14,179
12
34
5
67
89
10
1112
13
14
15
16
17
18
21
23 25
27
20
22
2619
24
O
HMBC Dendronesterone A (1)
1 2 22
23
3
1
23222
4
12
34
5
67
89
10
1112
13
14
15
16
17
18
21
23
28
25
27
20
22
2619
24
O
HNMR of Dendronesterone B (2)
1
12 28
X
FABMS of Dendronesterone B (2)
12
34
5
67
89
10
1112
13
14
15
16
17
18
21
23
28
25
27
20
22
2619
24
O m/z 396 C28H44O
12
3
45
67
8
9
10
1112
13
14
15
16
17
18
21
23 25
27
20
22
2619
24
O
1HNMR Dendronesterone C (3)
12
42223
182626
2119
COSY spectrum Dendronesterone C (3)
1 2 42223
1
24
22,23
12
3
45
67
8
9
10
1112
13
14
15
16
17
18
21
23 25
27
20
22
2619
24
O
DEPT Experiment of Dendronesterone C (3)
18
122
223
4
17 14
9
13
20
12
8
7615 11
2627
2119
12
3
45
67
8
9
10
1112
13
14
15
16
17
18
21
23 25
27
20
22
2619
24
O
HMBC Experiment of Dendronesterone C (3)
12
3
45
67
8
9
10
1112
13
14
15
16
17
18
21
23 25
27
20
22
2619
24
O
1 2 42223
5
1
222
234
17 149
HSQC Expermint of Dendronesterone C (3)
3
5
1
222
23,4
1 2 42223
12
3
45
67
8
9
10
1112
13
14
15
16
17
18
21
23 25
27
20
22
2619
24
O
17,149
182627
21
19
Expanded HMBC of Dendronesterone C (3)
12
3
45
67
8
9
10
1112
13
14
15
16
17
18
21
23 25
27
20
22
2619
24
O
5
1
222
234
19 21 2627
18
17 149
12
3
45
67
8
9
10
1112
13
14
15
16
17
18
21
23 25
27
20
22
2619
24
O
FABMS of Dendronesterone C (3)
m/z 381 (M++1) C27H40O
1HNMR of Dendronesterone D (4)
12
34
5
67
8
9
10
1112
13
14
15
16
17
18
21
23 25
27
20
22
2619
24
O
O
1 2
12
34
5
67
8
9
10
1112
13
14
15
16
17
18
21
23 25
27
20
22
2619
24
O
O
13C NMR of Dendronesterone D (4)
1 2322
Expanded 13C NMR of Dendronesterone D (4)
14 179
20 5
134
2312
10 824 7
256
16
15
2627
1121 19 18
Expanded COSY of Dendronesterone D (4)
12
34
5
67
8
9
10
1112
13
14
15
16
17
18
21
23 25
27
20
22
2619
24
O
O
HSQC of Dendronesterone D (4)
Expanded HSQC of Dendronesterone D (4)
14 17 920 513 1819211126
271525
616
72481023124
18
26,2719
21
12
34
5
6
7
8
9
10
1112
13
14
15
16
17
18
21
23 25
27
20
22
2619
24
O
O
HMBC of Dendronesterone D (4)
12
34
5
67
8
9
10
1112
13
14
15
16
17
18
21
23 25
27
20
22
2619
24
O
O
Bodies of the soft coral Lemnalia cervicorni were freeze-dried to give 0.42 Kg of a solid
extract with CH2Cl2 (3lX3), conc in vacum
37.1 g of CH2Cl2 extract
CC, Sil. gel using n-hex. and n-hex. -CH2Cl2 gradient, followed byCH2Cl2-EtOAc, gradientn-hex/CH2Cl2
(1:3)
Compound 7* Compounds 5*,6*
CC, Sil. gel using n-hex.-EtOAc(47:3)
Sub Fr.. ASub Fr.. C
* ED50 16.3, >50, >50, and >50 g/ml respectively against P-388 cytotoxic cell line* ED50 10.5, >50 >50 and >50 g/ml respectively against HT-29 cell line
(0:100)
Sub Fr.. B
Compounds 7*,8*
CH2Cl2/EtOAc(1:1)
.
CC, Sil. gel using n-hex.-CH2Cl2 (49:1)
CC, Sil. gel using n-hex.-acetone (99:1)
Extraction, Separation and purification Scheme for soft coral Lemnalia cervicorni
OH
1
2 3
4
5
67
8
9
1110
12
13
14
15
Lemnalol (5)
1
2 3
4
567
8
9
1110
12
13
14
15
Cervicol (6)
OH
1
2 3
4
567
8
9
1110
12
13
14
15
OH
Isolemnalol (7)
1
2 3
4
567
8
9
1110
12
13
14
15
4-oxo- ylangene (8)
O
Compounds Isolated from Lemnalia cervicorni
2D INADAQUATE of lemnalol
OH
1
2 3
4
5
67
8
9
1110
12
13
14
15
