Oxy-Polybrominated Diphenyl Ethers from the Indonesian Marine Sponge, <i>Lamellodysidea herbacea</i>: X-ray, SAR, and Computational Studies
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 anti...
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oai:doaj.org-article:7620e299d5c3463484cb1a68c8a0c9e12021-11-11T18:21:59ZOxy-Polybrominated Diphenyl Ethers from the Indonesian Marine Sponge, <i>Lamellodysidea herbacea</i>: X-ray, SAR, and Computational Studies10.3390/molecules262163281420-3049https://doaj.org/article/7620e299d5c3463484cb1a68c8a0c9e12021-10-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/21/6328https://doaj.org/toc/1420-3049Polybrominated 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 (<b>1</b>–<b>6</b>) were isolated from the sponge, <i>Lamellodysdiea herbacea</i>; <sup>13</sup>C NMR data for compound <b>6</b> are reported for the first time and their assignments are confirmed by their theoretical <sup>13</sup>C NMR chemical shifts (RMSE < 4.0 ppm). Methylation and acetylation of <b>1</b> (2, 3, 4, 5-tetrabromo-6-(3′, 5′-dibromo-2′-hydroxyphenoxy) phenol) at the phenol functional group gave seven molecules (<b>7</b>–<b>13</b>), of which <b>10</b>, <b>12</b>, and <b>13</b> were new. New crystal structures for <b>8</b> and <b>9</b> are also reported. Debromination carried out on <b>1</b> produced nine compounds (<b>1</b>, <b>2</b>, <b>14</b>, <b>16</b>–<b>18</b>, <b>20</b>, <b>23,</b> and <b>26</b>) of which <b>18</b> was new. Debromination product <b>16</b> showed a significant IC<sub>50</sub> 8.65 ± 1.11; 8.11 ± 1.43 µM against human embryonic kidney (HEK293T) cells. Compounds <b>1</b> and <b>16</b> exhibited antibacterial activity against Gram-positive <i>Staphylococcus aureus</i> and Gram-negative <i>Klebsiella pneumoniae</i> with MID 0.078 µg/disk. The number of four bromine atoms and two phenol functional groups are important for antibacterial activity (<i>S. aureus</i> and <i>K. pneumoniae</i>) 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.Novriyandi HanifTrianda Ayuning TyasLestari HidayatiFabians Faisal DinelsaDian ProvitaNyimas Ratna KinnaryFauzi Muhamad PrasetiawanGibral Abdul KhalikZaki MubarokDudi TohirAndi SetiawanMuhamad FaridViqqi KurniandaAnggia MurniNicole J. de VoogdJunichi TanakaMDPI AGarticleantibacterial activityHEK 293TPBDEDFT calculationsNMRX-rayOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6328, p 6328 (2021) |
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DOAJ |
| language |
EN |
| topic |
antibacterial activity HEK 293T PBDE DFT calculations NMR X-ray Organic chemistry QD241-441 |
| spellingShingle |
antibacterial activity HEK 293T PBDE DFT calculations NMR X-ray Organic chemistry QD241-441 Novriyandi Hanif Trianda Ayuning Tyas Lestari Hidayati Fabians Faisal Dinelsa Dian Provita Nyimas Ratna Kinnary Fauzi Muhamad Prasetiawan Gibral Abdul Khalik Zaki Mubarok Dudi Tohir Andi Setiawan Muhamad Farid Viqqi Kurnianda Anggia Murni Nicole J. de Voogd Junichi Tanaka Oxy-Polybrominated Diphenyl Ethers from the Indonesian Marine Sponge, <i>Lamellodysidea herbacea</i>: X-ray, SAR, and Computational Studies |
| description |
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 (<b>1</b>–<b>6</b>) were isolated from the sponge, <i>Lamellodysdiea herbacea</i>; <sup>13</sup>C NMR data for compound <b>6</b> are reported for the first time and their assignments are confirmed by their theoretical <sup>13</sup>C NMR chemical shifts (RMSE < 4.0 ppm). Methylation and acetylation of <b>1</b> (2, 3, 4, 5-tetrabromo-6-(3′, 5′-dibromo-2′-hydroxyphenoxy) phenol) at the phenol functional group gave seven molecules (<b>7</b>–<b>13</b>), of which <b>10</b>, <b>12</b>, and <b>13</b> were new. New crystal structures for <b>8</b> and <b>9</b> are also reported. Debromination carried out on <b>1</b> produced nine compounds (<b>1</b>, <b>2</b>, <b>14</b>, <b>16</b>–<b>18</b>, <b>20</b>, <b>23,</b> and <b>26</b>) of which <b>18</b> was new. Debromination product <b>16</b> showed a significant IC<sub>50</sub> 8.65 ± 1.11; 8.11 ± 1.43 µM against human embryonic kidney (HEK293T) cells. Compounds <b>1</b> and <b>16</b> exhibited antibacterial activity against Gram-positive <i>Staphylococcus aureus</i> and Gram-negative <i>Klebsiella pneumoniae</i> with MID 0.078 µg/disk. The number of four bromine atoms and two phenol functional groups are important for antibacterial activity (<i>S. aureus</i> and <i>K. pneumoniae</i>) 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. |
| format |
article |
| author |
Novriyandi Hanif Trianda Ayuning Tyas Lestari Hidayati Fabians Faisal Dinelsa Dian Provita Nyimas Ratna Kinnary Fauzi Muhamad Prasetiawan Gibral Abdul Khalik Zaki Mubarok Dudi Tohir Andi Setiawan Muhamad Farid Viqqi Kurnianda Anggia Murni Nicole J. de Voogd Junichi Tanaka |
| author_facet |
Novriyandi Hanif Trianda Ayuning Tyas Lestari Hidayati Fabians Faisal Dinelsa Dian Provita Nyimas Ratna Kinnary Fauzi Muhamad Prasetiawan Gibral Abdul Khalik Zaki Mubarok Dudi Tohir Andi Setiawan Muhamad Farid Viqqi Kurnianda Anggia Murni Nicole J. de Voogd Junichi Tanaka |
| author_sort |
Novriyandi Hanif |
| title |
Oxy-Polybrominated Diphenyl Ethers from the Indonesian Marine Sponge, <i>Lamellodysidea herbacea</i>: X-ray, SAR, and Computational Studies |
| title_short |
Oxy-Polybrominated Diphenyl Ethers from the Indonesian Marine Sponge, <i>Lamellodysidea herbacea</i>: X-ray, SAR, and Computational Studies |
| title_full |
Oxy-Polybrominated Diphenyl Ethers from the Indonesian Marine Sponge, <i>Lamellodysidea herbacea</i>: X-ray, SAR, and Computational Studies |
| title_fullStr |
Oxy-Polybrominated Diphenyl Ethers from the Indonesian Marine Sponge, <i>Lamellodysidea herbacea</i>: X-ray, SAR, and Computational Studies |
| title_full_unstemmed |
Oxy-Polybrominated Diphenyl Ethers from the Indonesian Marine Sponge, <i>Lamellodysidea herbacea</i>: X-ray, SAR, and Computational Studies |
| title_sort |
oxy-polybrominated diphenyl ethers from the indonesian marine sponge, <i>lamellodysidea herbacea</i>: x-ray, sar, and computational studies |
| publisher |
MDPI AG |
| publishDate |
2021 |
| url |
https://doaj.org/article/7620e299d5c3463484cb1a68c8a0c9e1 |
| work_keys_str_mv |
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