Asperginols A and B, Diterpene Pyrones, from an Aspergillus sp. and the Structure Revision of Previously Reported Analogues

Al-Khdhairawi, Amjad Ayad Qatran and Low, Yun-Yee and Manshoor, Nurhuda and Arya, Aditya and Jelecki, Maciej and Alshawsh, Mohammed Abdullah and Kamran, Sareh and Suliman, Rasha Saad and Low, Anis and Nagojappa, Narendra Babu Shivanagere and Weber, Jean-Frederic F. (2020) Asperginols A and B, Diterpene Pyrones, from an Aspergillus sp. and the Structure Revision of Previously Reported Analogues. Journal of Natural Products, 83 (12). pp. 3564-3570. ISSN 0163-3864, DOI https://doi.org/10.1021/acs.jnatprod.0c00618.

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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.

Item Type: Article
Funders: UNSPECIFIED
Uncontrolled Keywords: Aspergillus; Diterpenes; Molecular Structure; Pyrones; Spectrum Analysis
Subjects: Q Science > Q Science (General)
Q Science > QD Chemistry
Divisions: Faculty of Science
Faculty of Science > Department of Chemistry
Depositing User: Ms Zaharah Ramly
Date Deposited: 28 Nov 2023 01:20
Last Modified: 28 Nov 2023 01:20
URI: http://eprints.um.edu.my/id/eprint/36181

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