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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J Nat. Prod. 2006, 69, 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

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.

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.

A photo of Xenia

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).

Isolated Xenicane Diterpenoids from Soft Coral Xenia umbellata

1HNMR of Compound 1(Umbellacin A)

1 HNMR of Compound 2 (Umbellacin B) OMe 8 4a 11a 13 OAc 1618

H HCOSY of Compound 2 (Umbellacin B)

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

1 HNMR of compound 3 (umbellacin C) a

1H1 H COSY of Compound 3 (Umbellacin C)

13 C NMR of Compound 3 (Umbellacin C) a 4a

HSQC of Compound 3 (Umbellacin C)

HMBC of Compound 3 (Umbellacin C)

1 H NMR of compound 4 (Umbellacin D) a 11a OMe OAc

Expanded 13 C NMR and DEPT Experiment of Compound 4 (Umbellacin D) OMe a4a13 OAc 18

HSQC of Compound 4 (Umbellacin D)

1 HNMR of Compound 6 (Umbellacin F) OMe 14 4a 11a 13 OAc

13 C NMR of compound 6 (Umbellacin F) 1 OAC a OMe 9 4a

1 HNMR of compound 7 (umbellacin G) OMe 4a

1 H NMR of Compound 8 (14,15-epoxy xeniolide H) 12, a 3’ a

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

13 CNMR of Compound 8 (14,15-epoxy xeniolide H) a 4a

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

NOESY Experiment of Compound 8 (14,15-epoxy xeniolide H) 12, a,3’ a9

1 H NMR of Compound 9 (3-acetyl 14,15-epoxy xeniolide H) 12, a 8,4a,10 OAc X

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

Expanded 1H HCOSY of Compound 9 (3-acetyl 14,15-epoxy xeniolide H) 14 11a 8 4a

13 C NMR of Compound 9 (3-acetyl 14,15-epoxy xeniolide H) 1OAc a 4a OAc

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

1 H NMR of Compound 10 (Umbellacin H) OMe 14 4a 11a 8 OAc

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

13 C NMR of Compound 11 (Umbellacin I) 1 OAc a OMe a 7 13,5,18