Asperversiamides, Linearly Fused Prenylated Indole Alkaloids from the Marine-Derived Fungus Aspergillus versicolor
Asperversiamides A-H (1-8), eight linearly fused prenylated indole alkaloids featuring an unusual pyrano[3,2- f]indole unit, were isolated from the marine-derived fungus Aspergillus versicolor. The structures and absolute configurations of these compounds were elucidated by extensive spectroscopic analyses, single-crystal X-ray diffraction, electronic circular dichroism (ECD) calculations, and optical rotation (OR) calculations. The relative configuration of C-21 of iso-notoamide B was herein revised, and a new methodology for preliminarily determining if the relative configuration of the bicyclo[2.2.2]diazaoctane moiety of a spiro-bicyclo[2.2.2]diazaoctane-type indole alkaloid is syn or anti was developed. The anti-inflammatory activities of the isolated compounds were all tested, and of these compounds, 7 exhibited a potent inhibitory effect against iNOS with an IC50 value of 5.39 μM.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2018 |
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| Erschienen: |
2018 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:83 |
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| Enthalten in: |
The Journal of organic chemistry - 83(2018), 15 vom: 03. Aug., Seite 8483-8492 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Li, Huaqiang [VerfasserIn] |
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| Links: |
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| Themen: |
Indole Alkaloids |
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| Anmerkungen: |
Date Completed 16.09.2019 Date Revised 16.09.2019 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1021/acs.joc.8b01087 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM286569299 |
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| 500 | |a Date Completed 16.09.2019 | ||
| 500 | |a Date Revised 16.09.2019 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a Asperversiamides A-H (1-8), eight linearly fused prenylated indole alkaloids featuring an unusual pyrano[3,2- f]indole unit, were isolated from the marine-derived fungus Aspergillus versicolor. The structures and absolute configurations of these compounds were elucidated by extensive spectroscopic analyses, single-crystal X-ray diffraction, electronic circular dichroism (ECD) calculations, and optical rotation (OR) calculations. The relative configuration of C-21 of iso-notoamide B was herein revised, and a new methodology for preliminarily determining if the relative configuration of the bicyclo[2.2.2]diazaoctane moiety of a spiro-bicyclo[2.2.2]diazaoctane-type indole alkaloid is syn or anti was developed. The anti-inflammatory activities of the isolated compounds were all tested, and of these compounds, 7 exhibited a potent inhibitory effect against iNOS with an IC50 value of 5.39 μM | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 650 | 7 | |a Indole Alkaloids |2 NLM | |
| 700 | 1 | |a Sun, Weiguang |e verfasserin |4 aut | |
| 700 | 1 | |a Deng, Mengyi |e verfasserin |4 aut | |
| 700 | 1 | |a Zhou, Qun |e verfasserin |4 aut | |
| 700 | 1 | |a Wang, Jianping |e verfasserin |4 aut | |
| 700 | 1 | |a Liu, Junjun |e verfasserin |4 aut | |
| 700 | 1 | |a Chen, Chunmei |e verfasserin |4 aut | |
| 700 | 1 | |a Qi, Changxing |e verfasserin |4 aut | |
| 700 | 1 | |a Luo, Zengwei |e verfasserin |4 aut | |
| 700 | 1 | |a Xue, Yongbo |e verfasserin |4 aut | |
| 700 | 1 | |a Zhu, Hucheng |e verfasserin |4 aut | |
| 700 | 1 | |a Zhang, Yonghui |e verfasserin |4 aut | |
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