Antcamphorols A–K, Cytotoxic and ROS Scavenging Triterpenoids from Antrodia camphorata
Antrodia camphorata is a rare and valuable medicinal mushroom. In this work, 11 new triterpenoids, namely, antcamphorols A–K (1–11), together with 10 known triterpenoids, 12–21, were isolated from dish-cultured A. camphorata. Compound 1 is an unprecedented C31 lanostane-type triterpenoid featuring a...
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| Published in | Journal of natural products (Washington, D.C.) Vol. 83; no. 1; pp. 45 - 54 |
|---|---|
| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society and American Society of Pharmacognosy
24.01.2020
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0163-3864 1520-6025 1520-6025 |
| DOI | 10.1021/acs.jnatprod.9b00580 |
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| Abstract | Antrodia camphorata is a rare and valuable medicinal mushroom. In this work, 11 new triterpenoids, namely, antcamphorols A–K (1–11), together with 10 known triterpenoids, 12–21, were isolated from dish-cultured A. camphorata. Compound 1 is an unprecedented C31 lanostane-type triterpenoid featuring a methyl group at C-15 and a C-21–O–C-24 tetrahydropyran ring at C-17. Compounds 2–11 are ergostane-type triterpenoids, and they include two pairs of norergostanes 2–5. The structures of the new compounds were identified by NMR, 2D NMR, and HRESIMS data analyses. The absolute configurations of 1 and 6 were defined by X-ray diffraction data, and the absolute configuration at C-25 of 4 was determined by the modified Mosher’s method. Compounds 7, 9, 10, 16, and 19 showed significant ROS scavenging activities (63.9–70.5% at 20 μM) in high-glucose-induced HUVECs. Compounds 3 and 8 exhibited moderate cytotoxic activities against U251 (IC50, 9.2 μM) and MCF-7 (IC50, 8.1 μM) human cancer cell lines, respectively. |
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| AbstractList | Antrodia camphorata is a rare and valuable medicinal mushroom. In this work, 11 new triterpenoids, namely, antcamphorols A-K (1-11), together with 10 known triterpenoids, 12-21, were isolated from dish-cultured A. camphorata. Compound 1 is an unprecedented C31 lanostane-type triterpenoid featuring a methyl group at C-15 and a C-21-O-C-24 tetrahydropyran ring at C-17. Compounds 2-11 are ergostane-type triterpenoids, and they include two pairs of norergostanes 2-5. The structures of the new compounds were identified by NMR, 2D NMR, and HRESIMS data analyses. The absolute configurations of 1 and 6 were defined by X-ray diffraction data, and the absolute configuration at C-25 of 4 was determined by the modified Moshers method. Compounds 7, 9, 10, 16, and 19 showed significant ROS scavenging activities (63.9-70.5% at 20 mu M) in high-glucose-induced HUVECs. Compounds 3 and 8 exhibited moderate cytotoxic activities against U251 (IC50, 9.2 mu M) and MCF-7 (IC50, 8.1 mu M) human cancer cell lines, respectively. is a rare and valuable medicinal mushroom. In this work, 11 new triterpenoids, namely, antcamphorols A-K ( - ), together with 10 known triterpenoids, - , were isolated from dish-cultured . Compound is an unprecedented C lanostane-type triterpenoid featuring a methyl group at C-15 and a C-21-O-C-24 tetrahydropyran ring at C-17. Compounds - are ergostane-type triterpenoids, and they include two pairs of norergostanes - . The structures of the new compounds were identified by NMR, 2D NMR, and HRESIMS data analyses. The absolute configurations of and were defined by X-ray diffraction data, and the absolute configuration at C-25 of was determined by the modified Mosher's method. Compounds , , , , and showed significant ROS scavenging activities (63.9-70.5% at 20 μM) in high-glucose-induced HUVECs. Compounds and exhibited moderate cytotoxic activities against U251 (IC , 9.2 μM) and MCF-7 (IC , 8.1 μM) human cancer cell lines, respectively. Antrodia camphorata is a rare and valuable medicinal mushroom. In this work, 11 new triterpenoids, namely, antcamphorols A–K (1–11), together with 10 known triterpenoids, 12–21, were isolated from dish-cultured A. camphorata. Compound 1 is an unprecedented C₃₁ lanostane-type triterpenoid featuring a methyl group at C-15 and a C-21–O–C-24 tetrahydropyran ring at C-17. Compounds 2–11 are ergostane-type triterpenoids, and they include two pairs of norergostanes 2–5. The structures of the new compounds were identified by NMR, 2D NMR, and HRESIMS data analyses. The absolute configurations of 1 and 6 were defined by X-ray diffraction data, and the absolute configuration at C-25 of 4 was determined by the modified Mosher’s method. Compounds 7, 9, 10, 16, and 19 showed significant ROS scavenging activities (63.9–70.5% at 20 μM) in high-glucose-induced HUVECs. Compounds 3 and 8 exhibited moderate cytotoxic activities against U251 (IC₅₀, 9.2 μM) and MCF-7 (IC₅₀, 8.1 μM) human cancer cell lines, respectively. Antrodia camphorata is a rare and valuable medicinal mushroom. In this work, 11 new triterpenoids, namely, antcamphorols A-K (1-11), together with 10 known triterpenoids, 12-21, were isolated from dish-cultured A. camphorata. Compound 1 is an unprecedented C31 lanostane-type triterpenoid featuring a methyl group at C-15 and a C-21-O-C-24 tetrahydropyran ring at C-17. Compounds 2-11 are ergostane-type triterpenoids, and they include two pairs of norergostanes 2-5. The structures of the new compounds were identified by NMR, 2D NMR, and HRESIMS data analyses. The absolute configurations of 1 and 6 were defined by X-ray diffraction data, and the absolute configuration at C-25 of 4 was determined by the modified Mosher's method. Compounds 7, 9, 10, 16, and 19 showed significant ROS scavenging activities (63.9-70.5% at 20 μM) in high-glucose-induced HUVECs. Compounds 3 and 8 exhibited moderate cytotoxic activities against U251 (IC50, 9.2 μM) and MCF-7 (IC50, 8.1 μM) human cancer cell lines, respectively.Antrodia camphorata is a rare and valuable medicinal mushroom. In this work, 11 new triterpenoids, namely, antcamphorols A-K (1-11), together with 10 known triterpenoids, 12-21, were isolated from dish-cultured A. camphorata. Compound 1 is an unprecedented C31 lanostane-type triterpenoid featuring a methyl group at C-15 and a C-21-O-C-24 tetrahydropyran ring at C-17. Compounds 2-11 are ergostane-type triterpenoids, and they include two pairs of norergostanes 2-5. The structures of the new compounds were identified by NMR, 2D NMR, and HRESIMS data analyses. The absolute configurations of 1 and 6 were defined by X-ray diffraction data, and the absolute configuration at C-25 of 4 was determined by the modified Mosher's method. Compounds 7, 9, 10, 16, and 19 showed significant ROS scavenging activities (63.9-70.5% at 20 μM) in high-glucose-induced HUVECs. Compounds 3 and 8 exhibited moderate cytotoxic activities against U251 (IC50, 9.2 μM) and MCF-7 (IC50, 8.1 μM) human cancer cell lines, respectively. Antrodia camphorata is a rare and valuable medicinal mushroom. In this work, 11 new triterpenoids, namely, antcamphorols A–K (1–11), together with 10 known triterpenoids, 12–21, were isolated from dish-cultured A. camphorata. Compound 1 is an unprecedented C31 lanostane-type triterpenoid featuring a methyl group at C-15 and a C-21–O–C-24 tetrahydropyran ring at C-17. Compounds 2–11 are ergostane-type triterpenoids, and they include two pairs of norergostanes 2–5. The structures of the new compounds were identified by NMR, 2D NMR, and HRESIMS data analyses. The absolute configurations of 1 and 6 were defined by X-ray diffraction data, and the absolute configuration at C-25 of 4 was determined by the modified Mosher’s method. Compounds 7, 9, 10, 16, and 19 showed significant ROS scavenging activities (63.9–70.5% at 20 μM) in high-glucose-induced HUVECs. Compounds 3 and 8 exhibited moderate cytotoxic activities against U251 (IC50, 9.2 μM) and MCF-7 (IC50, 8.1 μM) human cancer cell lines, respectively. |
| Author | He, Jun-Bin Kuang, Yi Li, Bin Ma, Dik-Lung Qiao, Xue Xu, Lu-Lu Ye, Min Tang, Rui Leung, Chung-Hang |
| AuthorAffiliation | Department of Chemistry Hong Kong Baptist University State Key Laboratory of Natural and Biomimetic Drugs & Key Laboratory of Molecular Cardiovascular Sciences of Ministry of Education, School of Pharmaceutical Sciences State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences |
| AuthorAffiliation_xml | – name: Hong Kong Baptist University – name: State Key Laboratory of Natural and Biomimetic Drugs & Key Laboratory of Molecular Cardiovascular Sciences of Ministry of Education, School of Pharmaceutical Sciences – name: Department of Chemistry – name: State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences |
| Author_xml | – sequence: 1 givenname: Bin orcidid: 0000-0002-9391-3655 surname: Li fullname: Li, Bin organization: State Key Laboratory of Natural and Biomimetic Drugs & Key Laboratory of Molecular Cardiovascular Sciences of Ministry of Education, School of Pharmaceutical Sciences – sequence: 2 givenname: Yi surname: Kuang fullname: Kuang, Yi organization: State Key Laboratory of Natural and Biomimetic Drugs & Key Laboratory of Molecular Cardiovascular Sciences of Ministry of Education, School of Pharmaceutical Sciences – sequence: 3 givenname: Jun-Bin surname: He fullname: He, Jun-Bin organization: State Key Laboratory of Natural and Biomimetic Drugs & Key Laboratory of Molecular Cardiovascular Sciences of Ministry of Education, School of Pharmaceutical Sciences – sequence: 4 givenname: Rui surname: Tang fullname: Tang, Rui organization: State Key Laboratory of Natural and Biomimetic Drugs & Key Laboratory of Molecular Cardiovascular Sciences of Ministry of Education, School of Pharmaceutical Sciences – sequence: 5 givenname: Lu-Lu surname: Xu fullname: Xu, Lu-Lu organization: State Key Laboratory of Natural and Biomimetic Drugs & Key Laboratory of Molecular Cardiovascular Sciences of Ministry of Education, School of Pharmaceutical Sciences – sequence: 6 givenname: Chung-Hang surname: Leung fullname: Leung, Chung-Hang organization: State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences – sequence: 7 givenname: Dik-Lung orcidid: 0000-0002-9515-340X surname: Ma fullname: Ma, Dik-Lung organization: Hong Kong Baptist University – sequence: 8 givenname: Xue orcidid: 0000-0002-8771-7877 surname: Qiao fullname: Qiao, Xue email: qiaoxue@bjmu.edu.cn organization: State Key Laboratory of Natural and Biomimetic Drugs & Key Laboratory of Molecular Cardiovascular Sciences of Ministry of Education, School of Pharmaceutical Sciences – sequence: 9 givenname: Min orcidid: 0000-0002-9952-2380 surname: Ye fullname: Ye, Min email: yemin@bjmu.edu.cn organization: State Key Laboratory of Natural and Biomimetic Drugs & Key Laboratory of Molecular Cardiovascular Sciences of Ministry of Education, School of Pharmaceutical Sciences |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/31891260$$D View this record in MEDLINE/PubMed |
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| Cites_doi | 10.1016/S0953-7562(09)80541-8 10.1021/np200579b 10.1161/CIRCRESAHA.116.309326 10.3389/fphar.2018.01449 10.1002/jcp.26405 10.1111/bph.14652 10.1038/ijo.2017.149 10.1016/j.pharmthera.2013.04.001 10.1042/BCJ20160503C 10.1016/S0891-5849(99)00107-0 10.1021/cr200021m 10.1021/ol202217d 10.1021/np50117a004 10.3389/fphar.2016.00067 10.1016/j.abb.2008.11.003 10.1021/acs.jnatprod.6b00783 10.1093/ecam/nep108 10.1039/C5RA04327A 10.1002/9780470742761 10.1016/j.jsbmb.2004.01.010 10.1021/acs.jnatprod.6b00575 10.1021/np1002143 10.1016/j.phymed.2012.03.014 10.1098/rstb.2006.1837 10.1021/np400741s 10.1016/j.jep.2017.05.020 10.1021/np060333v 10.1089/ars.2016.6833 10.1039/c5ra04327a |
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| Keywords | OXIDATIVE STRESS DISRUPTION LIVER-INJURY ANTIINFLAMMATORY TRITERPENOIDS BIOSYNTHESIS |
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| Snippet | Antrodia camphorata is a rare and valuable medicinal mushroom. In this work, 11 new triterpenoids, namely, antcamphorols A–K (1–11), together with 10 known... Antrodia camphorata is a rare and valuable medicinal mushroom. In this work, 11 new triterpenoids, namely, antcamphorols A-K (1-11), together with 10 known... is a rare and valuable medicinal mushroom. In this work, 11 new triterpenoids, namely, antcamphorols A-K ( - ), together with 10 known triterpenoids, - , were... |
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| SubjectTerms | Agaricales - drug effects Antineoplastic Agents - chemistry Chemistry, Medicinal cytotoxicity Ergosterol - analogs & derivatives Ergosterol - chemistry human cell lines human diseases Humans Inhibitory Concentration 50 Life Sciences & Biomedicine medicinal fungi moieties Molecular Structure neoplasm cells neoplasms nuclear magnetic resonance spectroscopy Pharmacology & Pharmacy Plant Sciences Polyporales - chemistry Reactive Oxygen Species - analysis Science & Technology Steroids - chemistry Taiwanofungus camphoratus Triterpenes - chemistry triterpenoids X-ray diffraction |
| Title | Antcamphorols A–K, Cytotoxic and ROS Scavenging Triterpenoids from Antrodia camphorata |
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