Nine undescribed oxidized ergosterols from the endophytic fungus Penicillium herquei and their cytotoxic activity
Copyright © 2023 Elsevier Ltd. All rights reserved..
A chemical investigation of the EtOAc extract of the endophytic fungus Penicillium herquei led to the isolation of nine undescribed oxidized ergosterols, penicisterols A-I (1-9), along with ten known analogs (10-19). Their structures and absolute configurations were elucidated by a combination of spectroscopic data analysis, quantum-chemical electronic circular dichroism (ECD) calculations and comparisons, [Rh2(OCOCF3)4]-induced ECD experiments, DFT-calculated 13C chemical shifts and DP4+ probability analysis. Compound 1 was a rare example of ergosterol in which the bond between C-8 and C-9 was cleaved to form an enol ether. Moreover, compound 2 possessed a rare (2,5-dioxo-4-imidazolidinyl)-carbamic acid ester group substituted at C-3. All undescribed oxidized ergosterols (1-9) were evaluated for their cytotoxic activity against five cancer cell lines including 4T1 (mouse breast carcinoma), A549 (human pulmonary carcinoma), HCT-116 (human colorectal carcinoma), HeLa (human cervical carcinoma) and Hepg2 (human hepatoma carcinoma) cells. Compounds 2 and 3 displayed moderate cytotoxic activity against 4T1, A549 and HeLa cells, with IC50 values ranging from 17.22 to 31.35 μM.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2023 |
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| Erschienen: |
2023 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:212 |
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| Enthalten in: |
Phytochemistry - 212(2023) vom: 06. Aug., Seite 113716 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Deng, Mengyi [VerfasserIn] |
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| Links: |
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| Themen: |
Antineoplastic Agents |
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| Anmerkungen: |
Date Completed 15.06.2023 Date Revised 15.06.2023 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1016/j.phytochem.2023.113716 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| 520 | |a Copyright © 2023 Elsevier Ltd. All rights reserved. | ||
| 520 | |a A chemical investigation of the EtOAc extract of the endophytic fungus Penicillium herquei led to the isolation of nine undescribed oxidized ergosterols, penicisterols A-I (1-9), along with ten known analogs (10-19). Their structures and absolute configurations were elucidated by a combination of spectroscopic data analysis, quantum-chemical electronic circular dichroism (ECD) calculations and comparisons, [Rh2(OCOCF3)4]-induced ECD experiments, DFT-calculated 13C chemical shifts and DP4+ probability analysis. Compound 1 was a rare example of ergosterol in which the bond between C-8 and C-9 was cleaved to form an enol ether. Moreover, compound 2 possessed a rare (2,5-dioxo-4-imidazolidinyl)-carbamic acid ester group substituted at C-3. All undescribed oxidized ergosterols (1-9) were evaluated for their cytotoxic activity against five cancer cell lines including 4T1 (mouse breast carcinoma), A549 (human pulmonary carcinoma), HCT-116 (human colorectal carcinoma), HeLa (human cervical carcinoma) and Hepg2 (human hepatoma carcinoma) cells. Compounds 2 and 3 displayed moderate cytotoxic activity against 4T1, A549 and HeLa cells, with IC50 values ranging from 17.22 to 31.35 μM | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Cytotoxic activity | |
| 650 | 4 | |a Ergosterols | |
| 650 | 4 | |a Penicillium herquei | |
| 650 | 4 | |a Quantum-chemical (13)C calculations | |
| 650 | 4 | |a Quantum-chemical ECD calculations | |
| 650 | 4 | |a Rh(2)(OCOCF(3))(4)-induced ECD | |
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| 700 | 1 | |a Wan, Zhenling |e verfasserin |4 aut | |
| 700 | 1 | |a Xu, Jinbo |e verfasserin |4 aut | |
| 700 | 1 | |a Huang, Shuai |e verfasserin |4 aut | |
| 700 | 1 | |a Xie, Jiang |e verfasserin |4 aut | |
| 700 | 1 | |a Zhou, Xianli |e verfasserin |4 aut | |
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