Hanif, N. and Ayuning tyas, trianda and hidayati, lestari and Faisal dinelsa, Fabians and Provita, Dian and Ratna Kinary, Nyimas and Muhammad Prasetiawan, Fauzi and Abdul Khalik, Gibral and Mubarok, Zaki and Tohir, Dudi and Setiawan, Andi and Farid, Muhamad and Kurnianda, Viqqi and Murni, Anggia and de Voogd, Nicole J. and Tanaka, Junichi (2021) Oxy-Polybrominated Diphenyl Ethers from the Indonesian Marine Sponge, Lamellodysidea herbacea: X-ray, SAR, and Computational Studies. Molecules, 26 (6328). pp. 1-22. ISSN 1420-3049

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Official URL: https://www.mdpi.com/1420-3049/26/21/6328

Abstract

Polybrominated diphenyl ether (PBDE) compounds, derived from marine organisms, originate from symbiosis between marine sponges and cyanobacteria or bacteria. PBDEs have broad biological spectra; therefore, we analyzed structure and activity relationships of PBDEs to determine their potential as anticancer or antibacterial lead structures, through reactions and computational studies. Six known PBDEs (1–6) were isolated from the sponge, Lamellodysdiea herbacea; 13C NMR data for compound 6 are reported for the first time and their assignments are confirmed by their theoretical 13C NMR chemical shifts (RMSE < 4.0 ppm). Methylation and acetylation of 1 (2, 3, 4, 5-tetrabromo-6-(30 , 50 -dibromo-20 -hydroxyphenoxy) phenol) at the phenol functional group gave seven molecules (7–13), of which 10, 12, and 13 were new. New crystal structures for 8 and 9 are also reported. Debromination carried out on 1 produced nine compounds (1, 2, 14, 16–18, 20, 23, and 26) of which 18 was new. Debromination product 16 showed a significant IC50 8.65 ± 1.11; 8.11 ± 1.43 µM against human embryonic kidney (HEK293T) cells. Compounds 1 and 16 exhibited antibacterial activity against Gram-positive Staphylococcus aureus and Gram-negative Klebsiella pneumoniae with MID 0.078 µg/disk. The number of four bromine atoms and two phenol functional groups are important for antibacterial activity (S. aureus and K. pneumoniae) and cytotoxicity (HEK293T). The result was supported by analysis of frontier molecular orbitals (FMOs). We also propose possible products of acetylation and debromination using analysis of FMOs and electrostatic charges and we confirm the experimental result.

Item Type: Article
Subjects: Q Science > Q Science (General)
Depositing User: Dr. Andi Setiawan
Date Deposited: 01 Nov 2021 01:08
Last Modified: 01 Nov 2021 01:08
URI: http://repository.lppm.unila.ac.id/id/eprint/34749

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