New Guaiane-Type Sesquiterpenoids Biscogniauxiaols A–G with Anti-Fungal and Anti-Inflammatory Activities from the Endophytic Fungus <i>Biscogniauxia Petrensis</i>
Seven undescribed guaiane-type sesquiterpenoids named biscogniauxiaols A–G (<b>1</b>–<b>7</b>) were isolated from the endophytic fungus <i>Biscogniauxia petrensis</i> on <i>Dendrobium orchids.</i> Their structures were determined by extensive spectrosc...
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MDPI AG
2023-03-01
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| Series: | Journal of Fungi |
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| Online Access: | https://www.mdpi.com/2309-608X/9/4/393 |
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| author | Long Han Wen Zheng Sheng-Yan Qian Ming-Fei Yang Yong-Zhong Lu Zhang-Jiang He Ji-Chuan Kang |
| author_facet | Long Han Wen Zheng Sheng-Yan Qian Ming-Fei Yang Yong-Zhong Lu Zhang-Jiang He Ji-Chuan Kang |
| author_sort | Long Han |
| collection | DOAJ |
| description | Seven undescribed guaiane-type sesquiterpenoids named biscogniauxiaols A–G (<b>1</b>–<b>7</b>) were isolated from the endophytic fungus <i>Biscogniauxia petrensis</i> on <i>Dendrobium orchids.</i> Their structures were determined by extensive spectroscopic analyses, electronic circular dichroism (EC) and specific rotation (SR) calculations. Compound <b>1</b> represented a new family of guaiane-type sesquiterpenoids featuring an unprecedented [5/6/6/7] tetracyclic system. A plausible biosynthetic pathway for compounds <b>1</b>–<b>7</b> was proposed. The anti-fungal, anti-inflammatory and multidrug resistance reversal activities of the isolates were evaluated. Compounds <b>1</b>, <b>2</b> and <b>7</b> exhibited potent inhibitory activities against <i>Candida albicans</i> with MIC values ranging from 1.60 to 6.30 μM, and suppressed nitric oxide (NO) production with IC<sub>50</sub> ranging from 4.60 to 20.00 μM. Additionally, all compounds (100 μg/mL) enhanced the cytotoxicity of cisplatin in cisplatin-resistant non-small cell lung cancer cells (A549/DDP). This study opened up a new source for obtaining bioactive guaiane-type sesquiterpenoids and compounds <b>1</b>, <b>2</b>, and <b>7</b> were promising for further optimization as multifunctional inhibitors for anti-fungal (<i>C</i>. <i>albicans</i>) and anti-inflammatory purposes. |
| first_indexed | 2024-03-11T04:52:23Z |
| format | Article |
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| issn | 2309-608X |
| language | English |
| last_indexed | 2024-03-11T04:52:23Z |
| publishDate | 2023-03-01 |
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| series | Journal of Fungi |
| spelling | doaj.art-cb6fd42937164c72a53dc930feddeda92023-11-17T19:57:31ZengMDPI AGJournal of Fungi2309-608X2023-03-019439310.3390/jof9040393New Guaiane-Type Sesquiterpenoids Biscogniauxiaols A–G with Anti-Fungal and Anti-Inflammatory Activities from the Endophytic Fungus <i>Biscogniauxia Petrensis</i>Long Han0Wen Zheng1Sheng-Yan Qian2Ming-Fei Yang3Yong-Zhong Lu4Zhang-Jiang He5Ji-Chuan Kang6College of Life Sciences, Guizhou University, Guiyang 550025, ChinaCollege of Life Sciences, Guizhou University, Guiyang 550025, ChinaCollege of Life Sciences, Guizhou University, Guiyang 550025, ChinaCollege of Life Sciences, Guizhou University, Guiyang 550025, ChinaGuizhou Institute of Technology, School of Food and Pharmaceutical Engineering, Guiyang 550003, ChinaEngineering and Research Center for Southwest Bio-Pharmaceutical Resources of National Education Ministry of China, Guizhou University, Guiyang 550025, ChinaCollege of Life Sciences, Guizhou University, Guiyang 550025, ChinaSeven undescribed guaiane-type sesquiterpenoids named biscogniauxiaols A–G (<b>1</b>–<b>7</b>) were isolated from the endophytic fungus <i>Biscogniauxia petrensis</i> on <i>Dendrobium orchids.</i> Their structures were determined by extensive spectroscopic analyses, electronic circular dichroism (EC) and specific rotation (SR) calculations. Compound <b>1</b> represented a new family of guaiane-type sesquiterpenoids featuring an unprecedented [5/6/6/7] tetracyclic system. A plausible biosynthetic pathway for compounds <b>1</b>–<b>7</b> was proposed. The anti-fungal, anti-inflammatory and multidrug resistance reversal activities of the isolates were evaluated. Compounds <b>1</b>, <b>2</b> and <b>7</b> exhibited potent inhibitory activities against <i>Candida albicans</i> with MIC values ranging from 1.60 to 6.30 μM, and suppressed nitric oxide (NO) production with IC<sub>50</sub> ranging from 4.60 to 20.00 μM. Additionally, all compounds (100 μg/mL) enhanced the cytotoxicity of cisplatin in cisplatin-resistant non-small cell lung cancer cells (A549/DDP). This study opened up a new source for obtaining bioactive guaiane-type sesquiterpenoids and compounds <b>1</b>, <b>2</b>, and <b>7</b> were promising for further optimization as multifunctional inhibitors for anti-fungal (<i>C</i>. <i>albicans</i>) and anti-inflammatory purposes.https://www.mdpi.com/2309-608X/9/4/393endophytic fungus<i>Biscogniauxia petrensis</i>sesquiterpenoidsanti-fungal activityanti-inflammatory activitymultidrug resistance reversal activity |
| spellingShingle | Long Han Wen Zheng Sheng-Yan Qian Ming-Fei Yang Yong-Zhong Lu Zhang-Jiang He Ji-Chuan Kang New Guaiane-Type Sesquiterpenoids Biscogniauxiaols A–G with Anti-Fungal and Anti-Inflammatory Activities from the Endophytic Fungus <i>Biscogniauxia Petrensis</i> Journal of Fungi endophytic fungus <i>Biscogniauxia petrensis</i> sesquiterpenoids anti-fungal activity anti-inflammatory activity multidrug resistance reversal activity |
| title | New Guaiane-Type Sesquiterpenoids Biscogniauxiaols A–G with Anti-Fungal and Anti-Inflammatory Activities from the Endophytic Fungus <i>Biscogniauxia Petrensis</i> |
| title_full | New Guaiane-Type Sesquiterpenoids Biscogniauxiaols A–G with Anti-Fungal and Anti-Inflammatory Activities from the Endophytic Fungus <i>Biscogniauxia Petrensis</i> |
| title_fullStr | New Guaiane-Type Sesquiterpenoids Biscogniauxiaols A–G with Anti-Fungal and Anti-Inflammatory Activities from the Endophytic Fungus <i>Biscogniauxia Petrensis</i> |
| title_full_unstemmed | New Guaiane-Type Sesquiterpenoids Biscogniauxiaols A–G with Anti-Fungal and Anti-Inflammatory Activities from the Endophytic Fungus <i>Biscogniauxia Petrensis</i> |
| title_short | New Guaiane-Type Sesquiterpenoids Biscogniauxiaols A–G with Anti-Fungal and Anti-Inflammatory Activities from the Endophytic Fungus <i>Biscogniauxia Petrensis</i> |
| title_sort | new guaiane type sesquiterpenoids biscogniauxiaols a g with anti fungal and anti inflammatory activities from the endophytic fungus i biscogniauxia petrensis i |
| topic | endophytic fungus <i>Biscogniauxia petrensis</i> sesquiterpenoids anti-fungal activity anti-inflammatory activity multidrug resistance reversal activity |
| url | https://www.mdpi.com/2309-608X/9/4/393 |
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