Novel chlorinated and nitrogenated azaphilones with cytotoxic activities from the marine algal-derived fungus Chaetomium globosum 2020HZ23
Two novel chlorinated and nitrogenated azaphilones, namely N-butyl-2-aza-2-deoxychaetoviridin A (1) and N-hexyl-2-aza-2-deoxychaetoviridin A (2), along with a previously identified analogue, chaetoviridin A (3), were successfully obtained from Chaetomium globosum 2020HZ23, a marine algal-sourced end...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Frontiers Media S.A.
2023-08-01
|
| Series: | Frontiers in Microbiology |
| Subjects: | |
| Online Access: | https://www.frontiersin.org/articles/10.3389/fmicb.2023.1252563/full |
| _version_ | 1797739951830335488 |
|---|---|
| author | Zhong-Jie Gao Lu-Lu Cao Hai-Ping Ren Hua Yu Yan Wang |
| author_facet | Zhong-Jie Gao Lu-Lu Cao Hai-Ping Ren Hua Yu Yan Wang |
| author_sort | Zhong-Jie Gao |
| collection | DOAJ |
| description | Two novel chlorinated and nitrogenated azaphilones, namely N-butyl-2-aza-2-deoxychaetoviridin A (1) and N-hexyl-2-aza-2-deoxychaetoviridin A (2), along with a previously identified analogue, chaetoviridin A (3), were successfully obtained from Chaetomium globosum 2020HZ23, a marine algal-sourced endophytic fungus. The planar structures as well as the absolute configurations of these new metabolites were determined utilizing a synergistic approach that involved both spectroscopic techniques (1D/2D NMR and HRESIMS) and Density Functional Theory (DFT) calculations. Each compound was subject to in vitro cytotoxicity evaluation toward the A549 cancer cell line. Both compounds 1 and 2 demonstrated significant cytotoxicity, as evidenced by their respective IC50 values of 13.6 and 17.5 μM. Furthermore, 1 and 2 demonstrated potent cell migration inhibition, which elevated with increasing dose concentration. In contrast, compound 3 exhibited less cytotoxic activity relative to 1 and 2, suggesting that the cytotoxic potency escalates with N-substitution at the C-2 position and the introduction of a side chain. This finding could offer implications for future studies aimed at designing and refining lead compounds within this class. |
| first_indexed | 2024-03-12T14:05:35Z |
| format | Article |
| id | doaj.art-437c5cf8b2ab4a42a7b125e17d57e9a5 |
| institution | Directory Open Access Journal |
| issn | 1664-302X |
| language | English |
| last_indexed | 2024-03-12T14:05:35Z |
| publishDate | 2023-08-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Frontiers in Microbiology |
| spelling | doaj.art-437c5cf8b2ab4a42a7b125e17d57e9a52023-08-21T14:20:32ZengFrontiers Media S.A.Frontiers in Microbiology1664-302X2023-08-011410.3389/fmicb.2023.12525631252563Novel chlorinated and nitrogenated azaphilones with cytotoxic activities from the marine algal-derived fungus Chaetomium globosum 2020HZ23Zhong-Jie GaoLu-Lu CaoHai-Ping RenHua YuYan WangTwo novel chlorinated and nitrogenated azaphilones, namely N-butyl-2-aza-2-deoxychaetoviridin A (1) and N-hexyl-2-aza-2-deoxychaetoviridin A (2), along with a previously identified analogue, chaetoviridin A (3), were successfully obtained from Chaetomium globosum 2020HZ23, a marine algal-sourced endophytic fungus. The planar structures as well as the absolute configurations of these new metabolites were determined utilizing a synergistic approach that involved both spectroscopic techniques (1D/2D NMR and HRESIMS) and Density Functional Theory (DFT) calculations. Each compound was subject to in vitro cytotoxicity evaluation toward the A549 cancer cell line. Both compounds 1 and 2 demonstrated significant cytotoxicity, as evidenced by their respective IC50 values of 13.6 and 17.5 μM. Furthermore, 1 and 2 demonstrated potent cell migration inhibition, which elevated with increasing dose concentration. In contrast, compound 3 exhibited less cytotoxic activity relative to 1 and 2, suggesting that the cytotoxic potency escalates with N-substitution at the C-2 position and the introduction of a side chain. This finding could offer implications for future studies aimed at designing and refining lead compounds within this class.https://www.frontiersin.org/articles/10.3389/fmicb.2023.1252563/fullazaphilonessecondary metabolitesmarine fungusChaetomium globosumcytotoxic activity |
| spellingShingle | Zhong-Jie Gao Lu-Lu Cao Hai-Ping Ren Hua Yu Yan Wang Novel chlorinated and nitrogenated azaphilones with cytotoxic activities from the marine algal-derived fungus Chaetomium globosum 2020HZ23 Frontiers in Microbiology azaphilones secondary metabolites marine fungus Chaetomium globosum cytotoxic activity |
| title | Novel chlorinated and nitrogenated azaphilones with cytotoxic activities from the marine algal-derived fungus Chaetomium globosum 2020HZ23 |
| title_full | Novel chlorinated and nitrogenated azaphilones with cytotoxic activities from the marine algal-derived fungus Chaetomium globosum 2020HZ23 |
| title_fullStr | Novel chlorinated and nitrogenated azaphilones with cytotoxic activities from the marine algal-derived fungus Chaetomium globosum 2020HZ23 |
| title_full_unstemmed | Novel chlorinated and nitrogenated azaphilones with cytotoxic activities from the marine algal-derived fungus Chaetomium globosum 2020HZ23 |
| title_short | Novel chlorinated and nitrogenated azaphilones with cytotoxic activities from the marine algal-derived fungus Chaetomium globosum 2020HZ23 |
| title_sort | novel chlorinated and nitrogenated azaphilones with cytotoxic activities from the marine algal derived fungus chaetomium globosum 2020hz23 |
| topic | azaphilones secondary metabolites marine fungus Chaetomium globosum cytotoxic activity |
| url | https://www.frontiersin.org/articles/10.3389/fmicb.2023.1252563/full |
| work_keys_str_mv | AT zhongjiegao novelchlorinatedandnitrogenatedazaphiloneswithcytotoxicactivitiesfromthemarinealgalderivedfunguschaetomiumglobosum2020hz23 AT lulucao novelchlorinatedandnitrogenatedazaphiloneswithcytotoxicactivitiesfromthemarinealgalderivedfunguschaetomiumglobosum2020hz23 AT haipingren novelchlorinatedandnitrogenatedazaphiloneswithcytotoxicactivitiesfromthemarinealgalderivedfunguschaetomiumglobosum2020hz23 AT huayu novelchlorinatedandnitrogenatedazaphiloneswithcytotoxicactivitiesfromthemarinealgalderivedfunguschaetomiumglobosum2020hz23 AT yanwang novelchlorinatedandnitrogenatedazaphiloneswithcytotoxicactivitiesfromthemarinealgalderivedfunguschaetomiumglobosum2020hz23 |