Quinazolin-4-one Coupled with Pyrrolidin-2-iminium Alkaloids from Marine-Derived Fungus <em>Penicillium aurantiogriseum</em>
Three new alkaloids, including auranomides A and B (<strong>1</strong> and <strong>2</strong>), a new scaffold containing quinazolin-4-one substituted with a pyrrolidin-2-iminium moiety, and auranomide C (<strong>3</strong&...
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| Format: | Article |
| Language: | English |
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MDPI AG
2012-06-01
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| Series: | Marine Drugs |
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| Online Access: | http://www.mdpi.com/1660-3397/10/6/1297 |
| _version_ | 1811307285877620736 |
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| author | Huanqin Dai Hua Bai Jidong Wang Mei Liu Yaojun Tong Xueting Liu Hong Gao Na Yang Hui Guo Ke Yu Caixia Chen Fuhang Song Biao Ren Lixin Zhang |
| author_facet | Huanqin Dai Hua Bai Jidong Wang Mei Liu Yaojun Tong Xueting Liu Hong Gao Na Yang Hui Guo Ke Yu Caixia Chen Fuhang Song Biao Ren Lixin Zhang |
| author_sort | Huanqin Dai |
| collection | DOAJ |
| description | Three new alkaloids, including auranomides A and B (<strong>1</strong> and <strong>2</strong>), a new scaffold containing quinazolin-4-one substituted with a pyrrolidin-2-iminium moiety, and auranomide C (<strong>3</strong>), as well as two known metabolites auranthine (<strong>4</strong>) and aurantiomides C (<strong>5</strong>) were isolated from the marine-derived fungus <em>Penicillium aurantiogriseum</em>. The chemical structures of compounds <strong>1</strong>–<strong>3</strong> were elucidated by extensive spectroscopic methods, including IR, HRESIMS and 2D NMR spectroscopic analysis. The absolute configurations of compounds <strong>1</strong>–<strong>3</strong> were suggested from the perspective of a plausible biosynthesis pathway. Compounds <strong>1</strong>–<strong>3</strong> were subjected to antitumor and antimicrobial screening models. Auranomides A–C exhibited moderate cytotoxic activity against human tumor cells. Auranomides B was the most potent among them with an IC<sub>50</sub> value of 0.097 μmol/mL against HEPG2 cells. |
| first_indexed | 2024-04-13T09:01:52Z |
| format | Article |
| id | doaj.art-1d91d57f74b14fd38b24e6169d764b13 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-04-13T09:01:52Z |
| publishDate | 2012-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-1d91d57f74b14fd38b24e6169d764b132022-12-22T02:53:07ZengMDPI AGMarine Drugs1660-33972012-06-011061297130610.3390/md10061297Quinazolin-4-one Coupled with Pyrrolidin-2-iminium Alkaloids from Marine-Derived Fungus <em>Penicillium aurantiogriseum</em>Huanqin DaiHua BaiJidong WangMei LiuYaojun TongXueting LiuHong GaoNa YangHui GuoKe YuCaixia ChenFuhang SongBiao RenLixin ZhangThree new alkaloids, including auranomides A and B (<strong>1</strong> and <strong>2</strong>), a new scaffold containing quinazolin-4-one substituted with a pyrrolidin-2-iminium moiety, and auranomide C (<strong>3</strong>), as well as two known metabolites auranthine (<strong>4</strong>) and aurantiomides C (<strong>5</strong>) were isolated from the marine-derived fungus <em>Penicillium aurantiogriseum</em>. The chemical structures of compounds <strong>1</strong>–<strong>3</strong> were elucidated by extensive spectroscopic methods, including IR, HRESIMS and 2D NMR spectroscopic analysis. The absolute configurations of compounds <strong>1</strong>–<strong>3</strong> were suggested from the perspective of a plausible biosynthesis pathway. Compounds <strong>1</strong>–<strong>3</strong> were subjected to antitumor and antimicrobial screening models. Auranomides A–C exhibited moderate cytotoxic activity against human tumor cells. Auranomides B was the most potent among them with an IC<sub>50</sub> value of 0.097 μmol/mL against HEPG2 cells.http://www.mdpi.com/1660-3397/10/6/1297marine-derived fungus<em>Penicillium aurantiogriseum</em>quinazolin-4-oneantitumor |
| spellingShingle | Huanqin Dai Hua Bai Jidong Wang Mei Liu Yaojun Tong Xueting Liu Hong Gao Na Yang Hui Guo Ke Yu Caixia Chen Fuhang Song Biao Ren Lixin Zhang Quinazolin-4-one Coupled with Pyrrolidin-2-iminium Alkaloids from Marine-Derived Fungus <em>Penicillium aurantiogriseum</em> Marine Drugs marine-derived fungus <em>Penicillium aurantiogriseum</em> quinazolin-4-one antitumor |
| title | Quinazolin-4-one Coupled with Pyrrolidin-2-iminium Alkaloids from Marine-Derived Fungus <em>Penicillium aurantiogriseum</em> |
| title_full | Quinazolin-4-one Coupled with Pyrrolidin-2-iminium Alkaloids from Marine-Derived Fungus <em>Penicillium aurantiogriseum</em> |
| title_fullStr | Quinazolin-4-one Coupled with Pyrrolidin-2-iminium Alkaloids from Marine-Derived Fungus <em>Penicillium aurantiogriseum</em> |
| title_full_unstemmed | Quinazolin-4-one Coupled with Pyrrolidin-2-iminium Alkaloids from Marine-Derived Fungus <em>Penicillium aurantiogriseum</em> |
| title_short | Quinazolin-4-one Coupled with Pyrrolidin-2-iminium Alkaloids from Marine-Derived Fungus <em>Penicillium aurantiogriseum</em> |
| title_sort | quinazolin 4 one coupled with pyrrolidin 2 iminium alkaloids from marine derived fungus lt em gt penicillium aurantiogriseum lt em gt |
| topic | marine-derived fungus <em>Penicillium aurantiogriseum</em> quinazolin-4-one antitumor |
| url | http://www.mdpi.com/1660-3397/10/6/1297 |
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