Antiproliferative Illudalane Sesquiterpenes from the Marine Sediment Ascomycete <i>Aspergillus oryzae</i>
The new asperorlactone (<b>1</b>), along with the known illudalane sesquiterpene echinolactone D (<b>2</b>), two known pyrones, 4-(hydroxymethyl)-5-hydroxy-2<i>H</i>-pyran-2-one (<b>3</b>) and its acetate <b>4</b>, and 4-hydroxybenzaldehyde...
| Main Authors: | , , , , , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2021-06-01
|
| Series: | Marine Drugs |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1660-3397/19/6/333 |
| _version_ | 1797530592887177216 |
|---|---|
| author | Raha Orfali Shagufta Perveen Muhammad Farooq Khan Atallah F. Ahmed Mohammad A. Wadaan Areej Mohammad Al-Taweel Ali S. Alqahtani Fahd A. Nasr Sobia Tabassum Paolo Luciano Giuseppina Chianese Jyh-Horng Sheu Orazio Taglialatela-Scafati |
| author_facet | Raha Orfali Shagufta Perveen Muhammad Farooq Khan Atallah F. Ahmed Mohammad A. Wadaan Areej Mohammad Al-Taweel Ali S. Alqahtani Fahd A. Nasr Sobia Tabassum Paolo Luciano Giuseppina Chianese Jyh-Horng Sheu Orazio Taglialatela-Scafati |
| author_sort | Raha Orfali |
| collection | DOAJ |
| description | The new asperorlactone (<b>1</b>), along with the known illudalane sesquiterpene echinolactone D (<b>2</b>), two known pyrones, 4-(hydroxymethyl)-5-hydroxy-2<i>H</i>-pyran-2-one (<b>3</b>) and its acetate <b>4</b>, and 4-hydroxybenzaldehyde (<b>5</b>), were isolated from a culture of <i>Aspergillus oryzae</i>, collected from Red Sea marine sediments. The structure of asperorlactone (<b>1</b>) was elucidated by HR-ESIMS, 1D, and 2D NMR, and a comparison between experimental and DFT calculated electronic circular dichroism (ECD) spectra. This is the first report of illudalane sesquiterpenoids from <i>Aspergillus</i> fungi and, more in general, from ascomycetes. Asperorlactone (<b>1</b>) exhibited antiproliferative activity against human lung, liver, and breast carcinoma cell lines, with IC<sub>50</sub> values < 100 µM. All the isolated compounds were also evaluated for their toxicity using the zebrafish embryo model. |
| first_indexed | 2024-03-10T10:32:10Z |
| format | Article |
| id | doaj.art-55807f1c8d9b451184aaf06f5e848c1a |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-10T10:32:10Z |
| publishDate | 2021-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-55807f1c8d9b451184aaf06f5e848c1a2023-11-21T23:35:14ZengMDPI AGMarine Drugs1660-33972021-06-0119633310.3390/md19060333Antiproliferative Illudalane Sesquiterpenes from the Marine Sediment Ascomycete <i>Aspergillus oryzae</i>Raha Orfali0Shagufta Perveen1Muhammad Farooq Khan2Atallah F. Ahmed3Mohammad A. Wadaan4Areej Mohammad Al-Taweel5Ali S. Alqahtani6Fahd A. Nasr7Sobia Tabassum8Paolo Luciano9Giuseppina Chianese10Jyh-Horng Sheu11Orazio Taglialatela-Scafati12Department of Pharmacognosy, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi ArabiaDepartment of Pharmacognosy, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi ArabiaBio-Products Research Chair, Department of Zoology, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Pharmacognosy, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi ArabiaBio-Products Research Chair, Department of Zoology, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Pharmacognosy, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi ArabiaDepartment of Pharmacognosy, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi ArabiaMedicinal, Aromatic and Poisonous Plants Research Center, College of Pharmacy, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaInterdisciplinary Research Centre in Biomedical Materials (IRCBM), Lahore Campus, COMSATS University Islamabad, Islamabad 44000, PakistanDepartment of Pharmacy, School of Medicine and Surgery, University of Naples Federico II, Via Montesano 49, 80131 Naples, ItalyDepartment of Pharmacy, School of Medicine and Surgery, University of Naples Federico II, Via Montesano 49, 80131 Naples, ItalyDepartment of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 80424, TaiwanDepartment of Pharmacy, School of Medicine and Surgery, University of Naples Federico II, Via Montesano 49, 80131 Naples, ItalyThe new asperorlactone (<b>1</b>), along with the known illudalane sesquiterpene echinolactone D (<b>2</b>), two known pyrones, 4-(hydroxymethyl)-5-hydroxy-2<i>H</i>-pyran-2-one (<b>3</b>) and its acetate <b>4</b>, and 4-hydroxybenzaldehyde (<b>5</b>), were isolated from a culture of <i>Aspergillus oryzae</i>, collected from Red Sea marine sediments. The structure of asperorlactone (<b>1</b>) was elucidated by HR-ESIMS, 1D, and 2D NMR, and a comparison between experimental and DFT calculated electronic circular dichroism (ECD) spectra. This is the first report of illudalane sesquiterpenoids from <i>Aspergillus</i> fungi and, more in general, from ascomycetes. Asperorlactone (<b>1</b>) exhibited antiproliferative activity against human lung, liver, and breast carcinoma cell lines, with IC<sub>50</sub> values < 100 µM. All the isolated compounds were also evaluated for their toxicity using the zebrafish embryo model.https://www.mdpi.com/1660-3397/19/6/333<i>Aspergillus oryzae</i>marine fungusilludalane sesquiterpenesantiproliferative activityzebrafish toxicity |
| spellingShingle | Raha Orfali Shagufta Perveen Muhammad Farooq Khan Atallah F. Ahmed Mohammad A. Wadaan Areej Mohammad Al-Taweel Ali S. Alqahtani Fahd A. Nasr Sobia Tabassum Paolo Luciano Giuseppina Chianese Jyh-Horng Sheu Orazio Taglialatela-Scafati Antiproliferative Illudalane Sesquiterpenes from the Marine Sediment Ascomycete <i>Aspergillus oryzae</i> Marine Drugs <i>Aspergillus oryzae</i> marine fungus illudalane sesquiterpenes antiproliferative activity zebrafish toxicity |
| title | Antiproliferative Illudalane Sesquiterpenes from the Marine Sediment Ascomycete <i>Aspergillus oryzae</i> |
| title_full | Antiproliferative Illudalane Sesquiterpenes from the Marine Sediment Ascomycete <i>Aspergillus oryzae</i> |
| title_fullStr | Antiproliferative Illudalane Sesquiterpenes from the Marine Sediment Ascomycete <i>Aspergillus oryzae</i> |
| title_full_unstemmed | Antiproliferative Illudalane Sesquiterpenes from the Marine Sediment Ascomycete <i>Aspergillus oryzae</i> |
| title_short | Antiproliferative Illudalane Sesquiterpenes from the Marine Sediment Ascomycete <i>Aspergillus oryzae</i> |
| title_sort | antiproliferative illudalane sesquiterpenes from the marine sediment ascomycete i aspergillus oryzae i |
| topic | <i>Aspergillus oryzae</i> marine fungus illudalane sesquiterpenes antiproliferative activity zebrafish toxicity |
| url | https://www.mdpi.com/1660-3397/19/6/333 |
| work_keys_str_mv | AT rahaorfali antiproliferativeilludalanesesquiterpenesfromthemarinesedimentascomyceteiaspergillusoryzaei AT shaguftaperveen antiproliferativeilludalanesesquiterpenesfromthemarinesedimentascomyceteiaspergillusoryzaei AT muhammadfarooqkhan antiproliferativeilludalanesesquiterpenesfromthemarinesedimentascomyceteiaspergillusoryzaei AT atallahfahmed antiproliferativeilludalanesesquiterpenesfromthemarinesedimentascomyceteiaspergillusoryzaei AT mohammadawadaan antiproliferativeilludalanesesquiterpenesfromthemarinesedimentascomyceteiaspergillusoryzaei AT areejmohammadaltaweel antiproliferativeilludalanesesquiterpenesfromthemarinesedimentascomyceteiaspergillusoryzaei AT alisalqahtani antiproliferativeilludalanesesquiterpenesfromthemarinesedimentascomyceteiaspergillusoryzaei AT fahdanasr antiproliferativeilludalanesesquiterpenesfromthemarinesedimentascomyceteiaspergillusoryzaei AT sobiatabassum antiproliferativeilludalanesesquiterpenesfromthemarinesedimentascomyceteiaspergillusoryzaei AT paololuciano antiproliferativeilludalanesesquiterpenesfromthemarinesedimentascomyceteiaspergillusoryzaei AT giuseppinachianese antiproliferativeilludalanesesquiterpenesfromthemarinesedimentascomyceteiaspergillusoryzaei AT jyhhorngsheu antiproliferativeilludalanesesquiterpenesfromthemarinesedimentascomyceteiaspergillusoryzaei AT oraziotaglialatelascafati antiproliferativeilludalanesesquiterpenesfromthemarinesedimentascomyceteiaspergillusoryzaei |