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J Nat. Prod. 2006, 69, 338-341 Cytotoxic Xenia Diterpenoids from the Soft Coral Xenia umbellata Ali A. El-Gamal, Shang-Kwei Wang and Chang-Yih Duh Department.

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Presentation on theme: "J Nat. Prod. 2006, 69, 338-341 Cytotoxic Xenia Diterpenoids from the Soft Coral Xenia umbellata Ali A. El-Gamal, Shang-Kwei Wang and Chang-Yih Duh Department."— Presentation transcript:

1 J Nat. Prod. 2006, 69, 338-341 Cytotoxic Xenia Diterpenoids from the Soft Coral Xenia umbellata Ali A. El-Gamal, Shang-Kwei Wang and Chang-Yih Duh Department of Marine Biotechnology and Resources, National Sun Yat- sen University, Kaoshiung, Taiwan, Republic of China, Faculty of Pharmacy, Mansoura University, Egypt & Department of Microbiology,Kaoshiung Medical University, Kaoshiung, Taiwan, Republic of China

2 Abstract Eleven new diterpenoids, umbellacins A-G (1- 7), 14,15-epoxy-xeniolide H (8), 3-acetyl-14,15- epoxy- xeniolide H (9), and umbellacins H and I (11, 12), were isolated from a methylene chloride-soluble frations of the soft coral Xenia umbellata. The structures were elucidated by extensive spectroscopic analysis, and their cytotoxicity against selected cancer cells was measured in vitro.

3 Aim of study The soft coral Xenia umbellata was studied because CH 2 Cl 2 showed significant cytotoxicity to A549 (human lung adenocarcinoma), HT-29 (human colon adenocarcinoma) and P388 (mouse lymphocytic leukaemia). The aim of this study will deals with separation, structural elucidation and biological study of some cytotoxic xenicane-type diterpenooids characteristic for xenia umbellata.

4 A photo of Xenia

5

6 Compounds 2, 4, 5, 6, 10, and 11 exhibited cytotoxicity against P-388 lymphocytic leukemia with ED 50 values of 1.6, 4.2, 3.8, 3.7, 3.4, and 3.6  g/m, respectively., none of the isolates were cytotoxic to A549 (human lung adenocarcinoma)and HT-29 (human colon adenocarcinoma) cell lines (IC 50 >  g/mL).

7 Isolated Xenicane Diterpenoids from Soft Coral Xenia umbellata

8 1HNMR of Compound 1(Umbellacin A) 1 3 13 12 14 8 16 17 18

9 1 HNMR of Compound 2 (Umbellacin B) 12 17 3 14 OMe 8 4a 11a 13 OAc 1618

10 H HCOSY of Compound 2 (Umbellacin B)

11 HSQC of Compound 2 (Umbellacin B) 12 17 314 OMe 84a 11a 13 OAc16 18

12 1 HNMR of compound 3 (umbellacin C) 13 12 10 14 3 3 8 11a 9 16 17 18

13 1H1 H COSY of Compound 3 (Umbellacin C)

14 13 C NMR of Compound 3 (Umbellacin C) 1 14 11 4 12 10 13 3 15 8 11a 4a 7 19 6 9 16 17 5 18

15 HSQC of Compound 3 (Umbellacin C)

16 HMBC of Compound 3 (Umbellacin C)

17 1 H NMR of compound 4 (Umbellacin D) 12 3 8 19 4a 11a OMe OAc 16 17 18 13

18 Expanded 13 C NMR and DEPT Experiment of Compound 4 (Umbellacin D) 814 19 15 3 OMe 7 11 11a4a13 OAc 18

19 HSQC of Compound 4 (Umbellacin D)

20 1 HNMR of Compound 6 (Umbellacin F) 128 19 3 OMe 14 4a 11a 13 OAc 18 16 17

21 13 C NMR of compound 6 (Umbellacin F) 1 OAC 1147 12 819 15 3 14 11a OMe 9 4a

22 1 HNMR of compound 7 (umbellacin G) 13 1214 3838 19 9 19 1 OMe 4a 18 16 17

23 1 H NMR of Compound 8 (14,15-epoxy xeniolide H) 12,13 19 3 11a 3’ 14 8 9 4a 5 18 16 17

24 COSY of Compound 8 (14,15-epoxy xeniolide H)

25 13 CNMR of Compound 8 (14,15-epoxy xeniolide H) 1 11 13 12 19 4 3 8 14 15 11a 4a 6 18 16 17 9 5 10 7

26 HMBC of Compound 8 (14,15-epoxy xeniolide H)

27 NOESY Experiment of Compound 8 (14,15-epoxy xeniolide H) 12,13 19 3 11a,3’ 14 8 4a9

28 1 H NMR of Compound 9 (3-acetyl 14,15-epoxy xeniolide H) 12,13 19 3 1411a 8,4a,10 OAc X 9 6 5 10 1816 17

29 1 H 1 H COSY of Compound 9 (3-acetyl 14,15-epoxy xeniolide H)

30 Expanded 1H HCOSY of Compound 9 (3-acetyl 14,15-epoxy xeniolide H) 14 11a 8 4a 10 9 6 5 18 16 17

31 13 C NMR of Compound 9 (3-acetyl 14,15-epoxy xeniolide H) 1OAc 11 13 12 19 4 3838 14 15 7 11a 4a 6 9 16 18 OAc 10 5 17

32 HSQC of Compound 9 (3-acetyl 14,15-epoxy xeniolide H)

33 1 H NMR of Compound 10 (Umbellacin H) 12 19 3 OMe 14 4a 11a 8 OAc 18 16 17

34 1 H NMR of Compound 11 (Umbellacin I) 12 3 OMe 14 8 4a 11a OAc 16, 17 18

35 13 C NMR of Compound 11 (Umbellacin I) 1 OAc412 3 11a OMe 8 11 151919 4a 7 13,5,18

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