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

Journal of natural products 2020 Dec 24

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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.

Citation

Amjad Ayad Qatran Al-Khdhairawi, Yun-Yee Low, Nurhuda Manshoor, Aditya Arya, Maciej Jelecki, Mohammed Abdullah Alshawsh, Sareh Kamran, Rasha Saad Suliman, Anis Low, Narendra Babu Shivanagere Nagojappa, Jean-Frédéric F Weber. Asperginols A and B, Diterpene Pyrones, from an Aspergillus sp. and the Structure Revision of Previously Reported Analogues. Journal of natural products. 2020 Dec 24;83(12):3564-3570