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J. Nat. Prod. 2005, 68, 1749-1753 Sesquiterpenoids and Norsesquiterpenoids from the Formosan Soft Coral Lemnalia laevis Ali A. H. El-Gamal, E-Ping Chiu,

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Presentation on theme: "J. Nat. Prod. 2005, 68, 1749-1753 Sesquiterpenoids and Norsesquiterpenoids from the Formosan Soft Coral Lemnalia laevis Ali A. H. El-Gamal, E-Ping Chiu,"— Presentation transcript:

1 J. Nat. Prod. 2005, 68, 1749-1753 Sesquiterpenoids and Norsesquiterpenoids from the Formosan Soft Coral Lemnalia laevis Ali A. H. El-Gamal, E-Ping Chiu, Chia-Hua Li, Shi-Yie Cheng,Chang-Feng Dai and Chang-Yih Duh Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung, Taiwan, Republic of China, Faculty of Pharmacy, Mansoura University, Egypt, and Institute of Oceanography, National Taiwan University, Taipei

2 Abstract Eight new nornardosinane sequiterpenoids, laevinols A-H (1-8), a new neolemnane sesquiterpenoid, laevinone A (9), and the previously known 6  -acetyl-4  5  -dimethyl 1(10)R-epoxy-2  -hydroxy-7-oxodecalin (10) and 11,12-dihydroxy-6,10-eremophiladiene (11) were isolated from the methylene chloride solublesof the Formosan soft coral Lemnalia laevis. Their structures were elucidated by extensive spectroscopic analysis, and their cytotoxicity against selected cancer cells was measured in vitro.

3 A Photo of Lemnalia laveis A Photo of Lemnalia laveis

4 Extraction, Separation and Purification Scheme of Soft Coral Lemnalia laevis

5 Compounds Isolated from soft Coral Lemnalia laevis

6 H NMR of Laevinol A 1 H NMR of Laevinol A 1 7 2 6 12 99 4 9  3 15 13 8

7 H NMR of Laevinol B 1 H NMR of Laevinol B 1 726 12 1314 x

8 H H COSY of Laevinol B 1 H 1 H COSY of Laevinol B 1 72 6 1 7 2 6 3 3 8,4 8,4

9 of Laevinol B NOESY Experiment of Laevinol B 726 1314 12 7 2 6

10 H NMR of Laevinol C 1 H NMR of Laevinol C 17 2 6 8 12 X 13 14

11 H H COSY of Laevinol C 1 H 1 H COSY of Laevinol C 1 72 6 7 2 6 8 4

12 H H COSY of Laevinol C Expanded 1 H 1 H COSY of Laevinol C

13 NMR of Laevinol C 13 C NMR of Laevinol C 11 1 10 726

14 NMR of Laevinol C Expanded 13 C NMR of Laevinol C 7 2 6 5 3 12 9 8 11 14

15 of Laevinol C HSQC of Laevinol C 1 7 2 6 8 9, 4 3 5 3 12 14 11 8 7 2 6 1

16 H NMR of Laevinol D 1 H NMR of Laevinol D 1 27 x 6 13 14 x x 12

17 H NMR of Laevinol E 1 H NMR of Laevinol E 1 2 6 12 1314

18 H NMR of Laevinol F 1 H NMR of Laevinol F 2 7 6 1 9999 9999 12 4 8 8 3333 3333 14 13

19 H NMR of Laevinol G 1 H NMR of Laevinol G 72 6 1 9999 12 13 14 9999 8

20 H H COSY of Laevinol G 1 H 1 H COSY of Laevinol G 7 2 7 26 1 9999 6 1 3 8 14 13 12

21 H NMR of Laevinol H 1 H NMR of Laevinol H 7 16 9 13 14 12 9 8 3 x 4

22 NMR and DEPT expermints of Laevinol H 13 C NMR and DEPT expermints of Laevinol H 11 7 10 6 1 5 12 13 14 4

23 NMR and DEPT expermints of Laevinol H Expanded part of 13 C NMR and DEPT expermints of Laevinol H 7 10 6 1 5 12 4 8932 14 13

24 of Laevinol H HSQC of Laevinol H S 76 …S…..S 1 12 13 14 2 3 9 8 4 7 6 1

25 H NMR of Laevinone A 11 H NMR of Laevinone A OAc 13 9 4 26 7777 7777 11 14 15 X

26 H NMR of Compound 10 1 H NMR of Compound 10 2 6 8 1 12 3 13 14

27 H NMR of Compound 11 1 H NMR of Compound 11 1 6 1212 3333 3333 4444 1415 13


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