Terpenoids from the Deep-Sea-Derived Fungus <i>Penicillium</i> <i>thomii</i> YPGA3 and Their Bioactivities
A chemical study of the ethyl acetate (EtOAc) extract from the deep-sea-derived fungus <i>Penicillium</i> <i>thomii</i> YPGA3 led to the isolation of a new austalide meroterpenoid (<b>1</b>) and seven known analogues (<b>2</b>−<b>8</...
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| Format: | Article |
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MDPI AG
2020-03-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/18/3/164 |
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| author | Zhongbin Cheng Wan Liu Runzhu Fan Shouye Han Yuanli Li Xiaoyun Cui Jia Zhang Yinan Wu Xin Lv Yun Zhang Zhuhua Luo Siti Aisyah Alias Wei Xu Qin Li |
| author_facet | Zhongbin Cheng Wan Liu Runzhu Fan Shouye Han Yuanli Li Xiaoyun Cui Jia Zhang Yinan Wu Xin Lv Yun Zhang Zhuhua Luo Siti Aisyah Alias Wei Xu Qin Li |
| author_sort | Zhongbin Cheng |
| collection | DOAJ |
| description | A chemical study of the ethyl acetate (EtOAc) extract from the deep-sea-derived fungus <i>Penicillium</i> <i>thomii</i> YPGA3 led to the isolation of a new austalide meroterpenoid (<b>1</b>) and seven known analogues (<b>2</b>−<b>8</b>), two new labdane-type diterpenoids (<b>9</b> and <b>10</b>) and a known derivative (<b>11</b>). The structures of new compounds <b>1</b>, <b>9</b>, and <b>10</b> were determined by comprehensive analyses via nuclear magnetic resonance (NMR) and mass spectroscopy (MS) data. The absolute configurations of <b>1</b>, <b>9</b>, and <b>10</b> were determined by comparisons of experimental electronic circular dichroism (ECD) with the calculated ECD spectra. Compound <b>1</b> represented the third example of austalides bearing a hydroxyl group at C-5 instead of the conserved methoxy in other known analogues. To our knowledge, diterpenoids belonging to the labdane-type were discovered from species of <i>Penicillium</i> for the first time. Compound <b>1</b> showed cytotoxicity toward MDA-MB-468 cells with an IC<sub>50</sub> value of 38.9 μM. Compounds <b>2</b> and <b>11</b> exhibited inhibition against α-glucosidase with IC<sub>50</sub> values of 910 and 525 μM, respectively, being more active than the positive control acarbose (1.33 mM). |
| first_indexed | 2024-04-11T13:27:15Z |
| format | Article |
| id | doaj.art-d91f84d7608842b897fe467ef88975d0 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-04-11T13:27:15Z |
| publishDate | 2020-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-d91f84d7608842b897fe467ef88975d02022-12-22T04:22:01ZengMDPI AGMarine Drugs1660-33972020-03-0118316410.3390/md18030164md18030164Terpenoids from the Deep-Sea-Derived Fungus <i>Penicillium</i> <i>thomii</i> YPGA3 and Their BioactivitiesZhongbin Cheng0Wan Liu1Runzhu Fan2Shouye Han3Yuanli Li4Xiaoyun Cui5Jia Zhang6Yinan Wu7Xin Lv8Yun Zhang9Zhuhua Luo10Siti Aisyah Alias11Wei Xu12Qin Li13School of Pharmacy, Henan University, Kaifeng 475004, ChinaSchool of Pharmacy, Henan University, Kaifeng 475004, ChinaSchool of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, ChinaSchool of Pharmacy, Henan University, Kaifeng 475004, ChinaSchool of Pharmacy, Henan University, Kaifeng 475004, ChinaSchool of Pharmacy, Henan University, Kaifeng 475004, ChinaSchool of Pharmacy, Henan University, Kaifeng 475004, ChinaSchool of Pharmacy, Henan University, Kaifeng 475004, ChinaSchool of Pharmacy, Henan University, Kaifeng 475004, ChinaSchool of Pharmacy, Henan University, Kaifeng 475004, ChinaKey Laboratory of Marine Biogenetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, Xiamen 361005, ChinaInstitute of Ocean and Earth Science (IOES), C308, Institute of Postgraduate Studies Building, University of Malaya, Kuala Lumpur 50603, MalaysiaKey Laboratory of Marine Biogenetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, Xiamen 361005, ChinaSchool of Pharmacy, Henan University, Kaifeng 475004, ChinaA chemical study of the ethyl acetate (EtOAc) extract from the deep-sea-derived fungus <i>Penicillium</i> <i>thomii</i> YPGA3 led to the isolation of a new austalide meroterpenoid (<b>1</b>) and seven known analogues (<b>2</b>−<b>8</b>), two new labdane-type diterpenoids (<b>9</b> and <b>10</b>) and a known derivative (<b>11</b>). The structures of new compounds <b>1</b>, <b>9</b>, and <b>10</b> were determined by comprehensive analyses via nuclear magnetic resonance (NMR) and mass spectroscopy (MS) data. The absolute configurations of <b>1</b>, <b>9</b>, and <b>10</b> were determined by comparisons of experimental electronic circular dichroism (ECD) with the calculated ECD spectra. Compound <b>1</b> represented the third example of austalides bearing a hydroxyl group at C-5 instead of the conserved methoxy in other known analogues. To our knowledge, diterpenoids belonging to the labdane-type were discovered from species of <i>Penicillium</i> for the first time. Compound <b>1</b> showed cytotoxicity toward MDA-MB-468 cells with an IC<sub>50</sub> value of 38.9 μM. Compounds <b>2</b> and <b>11</b> exhibited inhibition against α-glucosidase with IC<sub>50</sub> values of 910 and 525 μM, respectively, being more active than the positive control acarbose (1.33 mM).https://www.mdpi.com/1660-3397/18/3/164<i>penicillium thomii</i> ypga3deep-sea-derived fungusaustalide meroterpenoidlabdane-type diterpenoidbioactivities |
| spellingShingle | Zhongbin Cheng Wan Liu Runzhu Fan Shouye Han Yuanli Li Xiaoyun Cui Jia Zhang Yinan Wu Xin Lv Yun Zhang Zhuhua Luo Siti Aisyah Alias Wei Xu Qin Li Terpenoids from the Deep-Sea-Derived Fungus <i>Penicillium</i> <i>thomii</i> YPGA3 and Their Bioactivities Marine Drugs <i>penicillium thomii</i> ypga3 deep-sea-derived fungus austalide meroterpenoid labdane-type diterpenoid bioactivities |
| title | Terpenoids from the Deep-Sea-Derived Fungus <i>Penicillium</i> <i>thomii</i> YPGA3 and Their Bioactivities |
| title_full | Terpenoids from the Deep-Sea-Derived Fungus <i>Penicillium</i> <i>thomii</i> YPGA3 and Their Bioactivities |
| title_fullStr | Terpenoids from the Deep-Sea-Derived Fungus <i>Penicillium</i> <i>thomii</i> YPGA3 and Their Bioactivities |
| title_full_unstemmed | Terpenoids from the Deep-Sea-Derived Fungus <i>Penicillium</i> <i>thomii</i> YPGA3 and Their Bioactivities |
| title_short | Terpenoids from the Deep-Sea-Derived Fungus <i>Penicillium</i> <i>thomii</i> YPGA3 and Their Bioactivities |
| title_sort | terpenoids from the deep sea derived fungus i penicillium i i thomii i ypga3 and their bioactivities |
| topic | <i>penicillium thomii</i> ypga3 deep-sea-derived fungus austalide meroterpenoid labdane-type diterpenoid bioactivities |
| url | https://www.mdpi.com/1660-3397/18/3/164 |
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