1. 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

2. A Photo of Dendronephthya soft coral

3. 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.

4. Aim 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 CH 2 Cl 2 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 CH 2 Cl 2 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).

5. Bioassay-guided fractionation of CH 2 Cl 2 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 Study

6. Extraction, Separation and purification Scheme for soft coral Dendronephthya gigantea

8. 1 1 H NMR of Dendronesterone A (1) 2 22,23 1826 27 19 21

9. COSY spectrum Dendronesterone A (1 ) 1 2 22 23 1 2 22,23 18 26 27 19 21

10. )HSQC Dendronesterone A (1 1 2 22 23 1 22 23 2 14,17 9

11. HMBC Dendronesterone A (1) 12 22 23 3 1 2 22 4

12. HNMR of Dendronesterone B (2) 1 1 2 28 X

13. FABMS of Dendronesterone B (2) m/z 396 C28H44O

14. 1 HNMR Dendronesterone C (3) 1 2 4 22 23 18 26 21 19

15. COSY spectrum Dendronesterone C (3) 12 4 22 23 1 2 4 22,23

16. DEPT Experiment of Dendronesterone C (3) 18 1 22 2 23 4 17 14 9 13 20 12 8 7 6 15 11 26 27 21 19

17. HMBC Experiment of Dendronesterone C (3) 1 2 4 22 23 5 1 22 2 23 4 17 14 9

18. HSQC Expermint of Dendronesterone C (3) 3 5 1 22 2 23,4 12 4 22 23 17,14 9 18 26 27 21 19

19. Expanded HMBC of Dendronesterone C (3) 5 1 22 2 23 4 19 21 26 27 18 17 14 9

20. FABMS of Dendronesterone C (3 ) m/z 381 (M++1) C27H40O

21. 1 HNMR of Dendronesterone D (4 ) 1 2

22. 13C NMR of Dendronesterone D (4) 1 2 3 22

23. Expanded 13 C NMR of Dendronesterone D (4) 14 17 9 20 5 13 4 23 12 10 8 24 7 25 6 16 15 26 27 11 21 19 18

24. Expanded COSY of Dendronesterone D (4 )

25. HSQC of Dendronesterone D (4)

26. Expanded HSQC of Dendronesterone D (4) 14 17920 5 13 18 1921 11 26 27 15 25 6 16 7248 10 23 12 4 18 26,27 19 21

27. HMBC of Dendronesterone D (4 )

28. Extraction, Separation and purification Scheme for soft coral Lemnalia cervicorn i

30. 2D INADAQUATE of lemnalol