Sulfur-Containing Polybromoindoles from the Formosan Red Alga Laurencia brongniartii Ali A. EI-Gamal, Wei-Lung Wang, and Chang-Yih Duh Department of Marine.

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Presentation transcript:

Sulfur-Containing Polybromoindoles from the Formosan Red Alga Laurencia brongniartii Ali A. EI-Gamal, Wei-Lung Wang, and Chang-Yih Duh Department of Marine Resources, National Sun Yat-Sen University, Kaohsiung, Taiwan & Department of Biology, National Changhua University of Education, Changhua, Taiwan, Republic of China

Abstract Five new sulfur-containing polybromoindoles, 2- methylsulfinyl-3-methylthio-4,5,6-tribromoindole (1), 3- methylsulfinyl-2,4,6-tribromoindole (2), 4,6-dibromo-2,3- di(methylsulfinyl)indole (3), 3,3’-bis(2’-methylsulfinyl-2- methylthio-4,6,4’,6’-tetrabromo)indole (4), and 3,3-bis(4,6- dibromo methylsulfinyl)indole (5), as well as seven known sulfur- containing polybromoindoles, 3-methylthio-2,4,6-tribromoindole (6), 3-methylthio-2,4,5,6-tetrabromoindole (7), 4,6-dibromo-2,3- di(methylthio)indole (8), 2,3-di(methylthio)- 4,5,6-tribromoindole (9), 4,6-dibromo-2-methylsulfinyl 3(methylthio)indole (10), 4,6- dibromo-2-(methylthio)indole (11), and 3,3-bis(4,6-dibromo-2- methylthio)indole (12), have been isolated from the Formosan red alga Laurencia brongniartii. The structures were elucidated by extensive spectral analysis, and their cytotoxicity against selected cancer cells was measured in vitro.

Aim of Study The red alga Laurencia brongniartii was reported to be source of polybrominated and sulfur-containing indoles. As part of our search for bioactive substances from marine organisms, Formosan red alga L. brongniartii was studied because EtOAc extracts showed significant cytotoxicity to A549 (human lung adenocarcinoma), HT- 29 (human colon adenocarcinoma), NUGC-3 (human gastric adenocarcinoma), HONE-1 (human nasopharyngeal carcinoma), and P-388 (mouse lymphocytic leukemia) cell cultures as determined by standard procedures. Bioassay-guided fractionation resulted in the isolation of five new sulfur-containing polybromoindoles, (1-5) as well as seven known sulfur- containing polybromo-indoles (6-12). Compounds 4 and 5 exhibited cytotoxicity against selected cancer cell lines.

A Photo of Red algae Laurencia brongniartii

Extraction, Seperation and Purification Schem for red alga Laurencia brongiartii Compound 4 exhibited cytotoxicity against HT-29 and P-388, while compound 5 exhibited cytototxicity against P-388 cell line. The other isolates were not cytotoxic against P-388 and HT-29 cell lines.

Sulfur-Containing Polybromoindoles from the Formosan Red Alga Laurencia brongniartii

1 HNMR of Compound 1 1 HNMR of Compound 1 7

13 C NMR and DEPT 90 0 Expermint of Compound 1 13 C NMR and DEPT 90 0 Expermint of Compound 1

1 HNMR of Compound 2

EIMS with clusters of Isotopic Peaks of Compound 2 m/z 417 C 9 H 6 79 Br 81 Br 2 NOS

13 C NMR of Compound 2 13 C NMR of Compound 2

HRMS of Compound 2 HRMS of Compound 2 m/z C9H679Br81Br2NOS

EIMS of compound 3 showed clusters of isotopic peaks EIMS of compound 3 showed clusters of isotopic peaks m/z C10H979Br81BrNO2S2

HRMS of Compound 3 HRMS of Compound 3 m/z C 10 H 9 79 Br 81 BrNO 2 S 2

1 H NMR of Compound 3 1 H NMR of Compound 3 NH 5 7 SOMeSOMe

1 H NMR of Compound 4 1 H NMR of Compound 4 NH-1 NH-1’ SMe SOMe 55’ 77’

HRMS of Compound 4 HRMS of Compound 4 m/z C18H1279Br281Br2N2OS2

1 H NMR of Compound 5 1 H NMR of Compound 5 NH 5 7 SOMe SOMe

HRMS of Compound 5 HRMS of Compound 5 m/z C18H1279Br281Br2N2O2S2

HRMS of Compound 5 showed Clusters of Isotopic peaks HRMS of Compound 5 showed Clusters of Isotopic peaks m/z C18H1279Br281Br2N2O2S2

1 HNMR of Compound 6 1 HNMR of Compound 6

13 C NMR and DEPT Experiments of Compound 6 13 C NMR and DEPT Experiments of Compound 6

1 HNMR of Compound 7 1 HNMR of Compound 7

13 CNMR and DEPT 90 0 of Compound 7 13 CNMR and DEPT 90 0 of Compound 7

MS of Compound 8 showed Clusters of Isotopic Peaks m/z 367 C 10 H 9 79 Br 81 BrNS 2

1 HNMR of Compound 8

1 HNMR of Compound 9

EIMS of Compound 9 Showed Clusters of Isotopic Peaks EIMS of Compound 9 Showed Clusters of Isotopic Peaks m/z 447 C 10 H8 79 Br BrNS 2

MS of Compound 8 showed Clusters of Isotopic Peaks m/z 367 C10H979Br81BrNS2

1 H NMR of Compound SOMe SCH 3

13 C NMR of Compound C NMR of Compound 10

1 H NMR of Compound 11 1 H NMR of Compound 11

m/z 640 C 18 H Br 2 81Br 2 N 2 S 2 EIMS of Compound 12 EIMS of Compound 12

1 H NMR of Compound 12 1 H NMR of Compound 12

EIMS of Compound 12 showed Clusters of Isotopic Peaks