Asperginols A and B, Diterpene Pyrones, from an Aspergillus sp. and the Structure Revision of Previously Reported AnaloguesClick to copy article linkArticle link copied!
- Amjad Ayad Qatran Al-Khdhairawi*Amjad Ayad Qatran Al-Khdhairawi*Email: [email protected], [email protected]School of Pharmacy, Faculty of Health & Medical Sciences, Taylor’s University Lakeside Campus, 47500 Subang Jaya, Selangor, MalaysiaMore by Amjad Ayad Qatran Al-Khdhairawi
- Yun-Yee LowYun-Yee LowDepartment of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, MalaysiaMore by Yun-Yee Low
- Nurhuda ManshoorNurhuda ManshoorAtta-ur-Rahman Institute for Natural Product Discovery (AuRIns), Universiti Teknologi MARA (UiTM) Selangor Branch, 42300 Bandar Puncak Alam, Selangor, MalaysiaMore by Nurhuda Manshoor
- Aditya AryaAditya AryaDepartment of Pharmacology and Therapeutics, Faculty of Medicine, Dentistry and Health Sciences, University of Melbourne, Parkville, VIC 3010, AustraliaDepartment of Pharmacology and Therapeutics, School of Medicine, Faculty of Health and Medical Sciences, Taylor’s University, 47500 Subang Jaya, MalaysiaMore by Aditya Arya
- Maciej JeleckiMaciej JeleckiFaculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Poznańskiego 8, 61-614 Poznań, PolandMore by Maciej Jelecki
- Mohammed Abdullah AlshawshMohammed Abdullah AlshawshDepartment of Pharmacology, Faculty of Medicine, University of Malaya, 50603 Kuala Lumpur, MalaysiaMore by Mohammed Abdullah Alshawsh
- Sareh KamranSareh KamranDepartment of Pharmacology, Faculty of Medicine, University of Malaya, 50603 Kuala Lumpur, MalaysiaMore by Sareh Kamran
- Rasha Saad SulimanRasha Saad SulimanCollege of Pharmacy, King Saud bin Abdulaziz University for Health Sciences Ministry of National Guard Health Affairs, 3177 Riyadh, Saudi ArabiaMore by Rasha Saad Suliman
- Anis LowAnis LowAtta-ur-Rahman Institute for Natural Product Discovery (AuRIns), Universiti Teknologi MARA (UiTM) Selangor Branch, 42300 Bandar Puncak Alam, Selangor, MalaysiaMore by Anis Low
- Narendra Babu Shivanagere NagojappaNarendra Babu Shivanagere NagojappaSchool of Pharmacy, Faculty of Health & Medical Sciences, Taylor’s University Lakeside Campus, 47500 Subang Jaya, Selangor, Malaysia
- Jean-Frédéric F. WeberJean-Frédéric F. WeberAtta-ur-Rahman Institute for Natural Product Discovery (AuRIns), Universiti Teknologi MARA (UiTM) Selangor Branch, 42300 Bandar Puncak Alam, Selangor, MalaysiaMore by Jean-Frédéric F. Weber
Abstract
Two new diterpene pyrones, asperginols A (1) and B (2), and four known analogues (3–6) were isolated from the endophytic fungus Aspergillus sp. HAB10R12. The structures and absolute configurations of these compounds were elucidated based on the analysis of their NMR, MS, and X-ray diffraction data. The revision of the absolute configurations at C-10, C-11, and C-14 of the known diterpene pyrones (3–6) and the determination of the configuration at the polyene side chain for compounds (4–6) were made using chemical methods and vibrational circular dichroism analysis. This group of diterpene pyrone compounds showed unique structural features including a 7/6/6 tricyclic diterpene moiety with an unusual trans–syn–trans stereochemical arrangement. Compound 6 showed moderate activity against the HT-29 colon cancer cell line.
Cited By
This article is cited by 7 publications.
- Christian Bailly. Discovery and current developments of isoindolinone-based fungal natural products. European Journal of Medicinal Chemistry Reports 2023, 9 , 100112. https://doi.org/10.1016/j.ejmcr.2023.100112
- Mostafa A. Asmaey. Unravelling the Secrets of
α
‐Pyrones from
Aspergillus
Fungi: A Comprehensive Review of Their Natural Sources, Biosynthesis, and Biological Activities. Chemistry & Biodiversity 2023, 20
(11)
https://doi.org/10.1002/cbdv.202301185
- Amjad Ayad Qatran Al-Khdhairawi, Jason Siau Ee Loo, Nurliana Abd Mutalib, Normala Abd Latip, Nurhuda Manshoor, Hamidah Abu Bakar, Narendra Babu Shivanagere Nagojappa, Jean-Frédéric Weber. Diketopiperazine and isoindolinone alkaloids from the endophytic fungus Aspergillus sp. HAB10R12. Phytochemistry 2023, 211 , 113685. https://doi.org/10.1016/j.phytochem.2023.113685
- Ahmed Hagag, Miada F. Abdelwahab, Adel M. Abd El-kader, Mostafa A. Fouad. The endophytic
Aspergillus
strains: A bountiful source of natural products. Journal of Applied Microbiology 2022, 132
(6)
, 4150-4169. https://doi.org/10.1111/jam.15489
- Ru-Yi Shang, Jie Cui, Jia-Xin Li, Xian-Xian Miao, Lu Zhang, Dong-Dong Xie, Liang Zhang, Hou-Wen Lin, Wei-Hua Jiao. Nigerin and ochracenes J−L, new sesquiterpenoids from the marine sponge symbiotic fungus Aspergillus niger. Tetrahedron 2022, 104 , 132599. https://doi.org/10.1016/j.tet.2021.132599
- Kazunari Sakai, Masato Iwatsuki, Taichi Kaneta, Aoi Kimishima, Yukihiro Asami, Toshiaki Sunazuka, Rokuro Masuma, Kenichi Nonaka. Sesquicillin F, a new insecticidal meroterpenoid produced by Mariannaea macrochlamydospora FKI-4735. The Journal of Antibiotics 2021, 74
(11)
, 817-820. https://doi.org/10.1038/s41429-021-00456-9
- Matthias Köck, Thomas Lindel, Jochen Junker. Incorporation of 4J-HMBC and NOE Data into Computer-Assisted Structure Elucidation with WebCocon. Molecules 2021, 26
(16)
, 4846. https://doi.org/10.3390/molecules26164846
Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.
Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.
The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.