Presentation is loading. Please wait.

Presentation is loading. Please wait.

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.

Published byMartina Hunter Modified over 9 years ago

Similar presentations

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

Download ppt "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."

Similar presentations

Using 2D NMR Strategy Organic Structure Analysis, Crews, Rodriguez and Jaspars.

Using 2D NMR Strategy Organic Structure Analysis, Crews, Rodriguez and Jaspars.
Sulfur-Containing Polybromoindoles from the Formosan Red Alga Laurencia brongniartii Ali A. EI-Gamal, Wei-Lung Wang, and Chang-Yih Duh Department of Marine.

Sulfur-Containing Polybromoindoles from the Formosan Red Alga Laurencia brongniartii Ali A. EI-Gamal, Wei-Lung Wang, and Chang-Yih Duh Department of Marine.
EFFECT OF PHYSICAL MODIFICATION AND IONIC STRENGTH ON THE SOLUBILITY AND DISSOLUTION OF PARACETAMOL By M.M.Nafadi From Department of Pharmaceutics and.

EFFECT OF PHYSICAL MODIFICATION AND IONIC STRENGTH ON THE SOLUBILITY AND DISSOLUTION OF PARACETAMOL By M.M.Nafadi From Department of Pharmaceutics and.
Kuo, Soong-Yu IUFRO Division 5 Conference 5.07B Using Plantation And Small- Diameter Timber In Composites.

Kuo, Soong-Yu IUFRO Division 5 Conference 5.07B Using Plantation And Small- Diameter Timber In Composites.
J. Nat. Prod. 2004, 67, 1650-1653 Steroids and Sesquiterpenoids from the Soft Corals Dendronephthya gigantea and Lemnalia cervicorni Chang-Yih Duh, Ali.

J. Nat. Prod. 2004, 67, Steroids and Sesquiterpenoids from the Soft Corals Dendronephthya gigantea and Lemnalia cervicorni Chang-Yih Duh, Ali.
A Photo of Viburnum species A Photo of Viburnum species.

A Photo of Viburnum species A Photo of Viburnum species.
The molecular formula is C 5 H 8. What is the structure?

The molecular formula is C 5 H 8. What is the structure?
Chem 440/540 Advanced Organic Spectroscopy Introduction What spectroscopic techniques would be useful in determining the structure of this compound? H-1.

Chem 440/540 Advanced Organic Spectroscopy Introduction What spectroscopic techniques would be useful in determining the structure of this compound? H-1.
Introduction CAS-Croucher Funding Scheme for Joint Laboratories CAS-CF03/04.SC01 CAS-CF03/04.SC01 Isolation and purification of marine bioactive compounds.

Introduction CAS-Croucher Funding Scheme for Joint Laboratories CAS-CF03/04.SC01 CAS-CF03/04.SC01 Isolation and purification of marine bioactive compounds.
4 aromatic protons Can we use 2D to assign this spectrum? Structure first determined by Woodward in 1948 (without NMR!)

4 aromatic protons Can we use 2D to assign this spectrum? Structure first determined by Woodward in 1948 (without NMR!)
Therapeutic Implications and Prognostic Significance of c-Met in Esophageal Squamous Cell Cancer Ching Tzao 1, Chun-Ya Wang 1, Ban-Hen Chen 1, Guang-Huan.

Therapeutic Implications and Prognostic Significance of c-Met in Esophageal Squamous Cell Cancer Ching Tzao 1, Chun-Ya Wang 1, Ban-Hen Chen 1, Guang-Huan.
Introduction to NMR Spectroscopy and Imaging Review (Spring Term, 2011) Department of Chemistry National Sun Yat-sen University 核磁共振光譜與影像導論.

Introduction to NMR Spectroscopy and Imaging Review (Spring Term, 2011) Department of Chemistry National Sun Yat-sen University 核磁共振光譜與影像導論.
Abstract The search for novel antibacterial agents has acquired a new sense of urgency due to the dramatic rise of antibiotic resistance among bacterial.

Abstract The search for novel antibacterial agents has acquired a new sense of urgency due to the dramatic rise of antibiotic resistance among bacterial.
Introduction Microtropis fokienensis Dunn 1) (Celastraceae) is a small shrub that grows in high altitude forests throughout southern China and Taiwan.

Introduction Microtropis fokienensis Dunn 1) (Celastraceae) is a small shrub that grows in high altitude forests throughout southern China and Taiwan.
DEPARTMENT OF CELL BIOLOGY Head: Dr. Jacek Bigda, Associate Professor Research Staff: Dr. Małgorzata Doszczak Dr. Patrycja Koszałka Dr. Zuzanna Dobrzańska.

DEPARTMENT OF CELL BIOLOGY Head: Dr. Jacek Bigda, Associate Professor Research Staff: Dr. Małgorzata Doszczak Dr. Patrycja Koszałka Dr. Zuzanna Dobrzańska.
Secondary metabolite mapping identifies Scutellaria inhibitors of human lung cancer cells Jiayu Gao, Huiying Zhao, Peter J. Hylands, Olivia Corcoran Journal.

Secondary metabolite mapping identifies Scutellaria inhibitors of human lung cancer cells Jiayu Gao, Huiying Zhao, Peter J. Hylands, Olivia Corcoran Journal.
The absolute configuration of prunioside A from Spiraea prunifolia and biological activities of related compounds Meng Que.

The absolute configuration of prunioside A from Spiraea prunifolia and biological activities of related compounds Meng Que.
Table S1. Hypoxia increases signaling through JNK in colon cancer cell lines in a cell-specific manner Shown are the ratios of c-Jun phosphorylation during.

Table S1. Hypoxia increases signaling through JNK in colon cancer cell lines in a cell-specific manner Shown are the ratios of c-Jun phosphorylation during.
Supporting Information Barceloneic acid C, a new polyketide from an endophytic fungus Phoma sp. JS752 and its antibacterial activities Xuekui Xia 1,2†,

Supporting Information Barceloneic acid C, a new polyketide from an endophytic fungus Phoma sp. JS752 and its antibacterial activities Xuekui Xia 1,2†,
Bill Gerwick Research Interests Characterizing the ‘weird and wonderful’ natural products of marine algae and cyanobacteria Drug discovery from marine.

Bill Gerwick Research Interests Characterizing the ‘weird and wonderful’ natural products of marine algae and cyanobacteria Drug discovery from marine.

Similar presentations

Ads by Google