Lanostane Triterpenoids and Ergostane Steroids from <i>Ganoderma luteomarginatum</i> and Their Cytotoxicity
Macrofungus <i>Ganoderma luteomarginatum</i> is one of the main species of <i>Ganoderma</i> fungi distributed in Hainan province of China, the fruiting bodies of which have been widely used in folk as a healthy food to prevent tumors. To explore the potential cytotoxic consti...
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MDPI AG
2022-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/20/6989 |
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| author | Qingyun Ma Shuangshuang Zhang Li Yang Qingyi Xie Haofu Dai Zhifang Yu Youxing Zhao |
| author_facet | Qingyun Ma Shuangshuang Zhang Li Yang Qingyi Xie Haofu Dai Zhifang Yu Youxing Zhao |
| author_sort | Qingyun Ma |
| collection | DOAJ |
| description | Macrofungus <i>Ganoderma luteomarginatum</i> is one of the main species of <i>Ganoderma</i> fungi distributed in Hainan province of China, the fruiting bodies of which have been widely used in folk as a healthy food to prevent tumors. To explore the potential cytotoxic constituents from <i>G</i>. <i>luteomarginatum</i>, the phytochemical investigation on the ethyl acetate soluble fraction of 95% ethanolic extract from the fruiting bodies of this fungus led to the isolation of twenty-six lanostane triterpenoids (<b>1</b>–<b>26</b>), including three undescribed ones (<b>1</b>–<b>3</b>), together with eight ergostane steroids (<b>27</b>–<b>34</b>). The structures of three new lanostane triterpenoids were elucidated as lanosta-7,9(11)-dien-3β-acetyloxy-24,25-diol (<b>1</b>), lanosta-7,9(11)-dien-3-oxo-24,26-diol-25-methoxy (<b>2</b>), and lanosta-8,20(22)-dien-3,11,23-trioxo-7β,15β-diol-26-oic acid methyl ester (<b>3</b>) by the analysis of 1D, 2D NMR, and HRESIMS spectroscopic data. All isolates were assayed for their cytotoxic activities using three human cancer cell lines (K562, BEL-7402, and SGC-7901) and seven lanostane triterpenoids (<b>1</b>, <b>2</b>, <b>7</b>, <b>13</b>, <b>18</b>, <b>22</b>, and <b>24</b>), and one ergostane steroid (<b>34</b>) showed definite cytotoxicity with IC<sub>50</sub> values that ranged from 6.64 to 47.63 μg/mL. Among these cytotoxic lanostane triterpenoids, compounds <b>2</b> and <b>1</b><b>3</b> showed general cytotoxicity against three human cancer cell lines, while compounds <b>1</b> and <b>18</b> exhibited significant selective cytotoxicity against K562 cells with IC<sub>50</sub> values of 8.59 and 8.82 μg/mL, respectively. Furthermore, the preliminary structure–cytotoxicity relationships was proposed. |
| first_indexed | 2024-03-09T19:42:35Z |
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| publishDate | 2022-10-01 |
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| spelling | doaj.art-9c3d824a0d5c4f64bab37bdcb3bcc2462023-11-24T01:35:12ZengMDPI AGMolecules1420-30492022-10-012720698910.3390/molecules27206989Lanostane Triterpenoids and Ergostane Steroids from <i>Ganoderma luteomarginatum</i> and Their CytotoxicityQingyun Ma0Shuangshuang Zhang1Li Yang2Qingyi Xie3Haofu Dai4Zhifang Yu5Youxing Zhao6Haikou Key Laboratory for Research and Utilization of Tropical Natural Products, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences & Hainan Key Laboratory for Protection and Utilization of Tropical Bioresources, Hainan Academy of Tropical Agricultural Resource, Haikou 571101, ChinaJiangsu Food&Pharmaceutical Science College, Huaian 223003, ChinaHaikou Key Laboratory for Research and Utilization of Tropical Natural Products, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences & Hainan Key Laboratory for Protection and Utilization of Tropical Bioresources, Hainan Academy of Tropical Agricultural Resource, Haikou 571101, ChinaHaikou Key Laboratory for Research and Utilization of Tropical Natural Products, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences & Hainan Key Laboratory for Protection and Utilization of Tropical Bioresources, Hainan Academy of Tropical Agricultural Resource, Haikou 571101, ChinaHaikou Key Laboratory for Research and Utilization of Tropical Natural Products, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences & Hainan Key Laboratory for Protection and Utilization of Tropical Bioresources, Hainan Academy of Tropical Agricultural Resource, Haikou 571101, ChinaCollege of Food Science and Technology, Nanjing Agricultural University, Nanjing 210095, ChinaHaikou Key Laboratory for Research and Utilization of Tropical Natural Products, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences & Hainan Key Laboratory for Protection and Utilization of Tropical Bioresources, Hainan Academy of Tropical Agricultural Resource, Haikou 571101, ChinaMacrofungus <i>Ganoderma luteomarginatum</i> is one of the main species of <i>Ganoderma</i> fungi distributed in Hainan province of China, the fruiting bodies of which have been widely used in folk as a healthy food to prevent tumors. To explore the potential cytotoxic constituents from <i>G</i>. <i>luteomarginatum</i>, the phytochemical investigation on the ethyl acetate soluble fraction of 95% ethanolic extract from the fruiting bodies of this fungus led to the isolation of twenty-six lanostane triterpenoids (<b>1</b>–<b>26</b>), including three undescribed ones (<b>1</b>–<b>3</b>), together with eight ergostane steroids (<b>27</b>–<b>34</b>). The structures of three new lanostane triterpenoids were elucidated as lanosta-7,9(11)-dien-3β-acetyloxy-24,25-diol (<b>1</b>), lanosta-7,9(11)-dien-3-oxo-24,26-diol-25-methoxy (<b>2</b>), and lanosta-8,20(22)-dien-3,11,23-trioxo-7β,15β-diol-26-oic acid methyl ester (<b>3</b>) by the analysis of 1D, 2D NMR, and HRESIMS spectroscopic data. All isolates were assayed for their cytotoxic activities using three human cancer cell lines (K562, BEL-7402, and SGC-7901) and seven lanostane triterpenoids (<b>1</b>, <b>2</b>, <b>7</b>, <b>13</b>, <b>18</b>, <b>22</b>, and <b>24</b>), and one ergostane steroid (<b>34</b>) showed definite cytotoxicity with IC<sub>50</sub> values that ranged from 6.64 to 47.63 μg/mL. Among these cytotoxic lanostane triterpenoids, compounds <b>2</b> and <b>1</b><b>3</b> showed general cytotoxicity against three human cancer cell lines, while compounds <b>1</b> and <b>18</b> exhibited significant selective cytotoxicity against K562 cells with IC<sub>50</sub> values of 8.59 and 8.82 μg/mL, respectively. Furthermore, the preliminary structure–cytotoxicity relationships was proposed.https://www.mdpi.com/1420-3049/27/20/6989<i>Ganoderma luteomarginatum</i>lanostane triterpenoidsergostane steroidscytotoxic activity |
| spellingShingle | Qingyun Ma Shuangshuang Zhang Li Yang Qingyi Xie Haofu Dai Zhifang Yu Youxing Zhao Lanostane Triterpenoids and Ergostane Steroids from <i>Ganoderma luteomarginatum</i> and Their Cytotoxicity Molecules <i>Ganoderma luteomarginatum</i> lanostane triterpenoids ergostane steroids cytotoxic activity |
| title | Lanostane Triterpenoids and Ergostane Steroids from <i>Ganoderma luteomarginatum</i> and Their Cytotoxicity |
| title_full | Lanostane Triterpenoids and Ergostane Steroids from <i>Ganoderma luteomarginatum</i> and Their Cytotoxicity |
| title_fullStr | Lanostane Triterpenoids and Ergostane Steroids from <i>Ganoderma luteomarginatum</i> and Their Cytotoxicity |
| title_full_unstemmed | Lanostane Triterpenoids and Ergostane Steroids from <i>Ganoderma luteomarginatum</i> and Their Cytotoxicity |
| title_short | Lanostane Triterpenoids and Ergostane Steroids from <i>Ganoderma luteomarginatum</i> and Their Cytotoxicity |
| title_sort | lanostane triterpenoids and ergostane steroids from i ganoderma luteomarginatum i and their cytotoxicity |
| topic | <i>Ganoderma luteomarginatum</i> lanostane triterpenoids ergostane steroids cytotoxic activity |
| url | https://www.mdpi.com/1420-3049/27/20/6989 |
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