Diketopiperazine and isoindolinone alkaloids from the endophytic fungus Aspergillus sp. HAB10R12

Four previously undescribed alkaloids, aspergillinine A–D, and four known diterpene pyrones were isolated from the potato dextrose agar (PDA) culture of Aspergillus sp. HAB10R12. The chemical structures of the isolated compounds were elucidated based on a detailed analysis of their NMR and MS data....

وصف كامل

التفاصيل البيبلوغرافية
الحاوية / القاعدة:Phytochemistry
المؤلف الرئيسي: Al-Khdhairawi A.A.Q.; Loo J.S.E.; Abd Mutalib N.; Abd Latip N.; Manshoor N.; Abu Bakar H.; Babu Shivanagere Nagojappa N.; Weber J.-F.
التنسيق: مقال
اللغة:English
منشور في: Elsevier Ltd 2023
الوصول للمادة أونلاين:https://www.scopus.com/inward/record.uri?eid=2-s2.0-85153227185&doi=10.1016%2fj.phytochem.2023.113685&partnerID=40&md5=fb5c66ca1710763bcb44d3cf7ff2977e
الوصف
الملخص:Four previously undescribed alkaloids, aspergillinine A–D, and four known diterpene pyrones were isolated from the potato dextrose agar (PDA) culture of Aspergillus sp. HAB10R12. The chemical structures of the isolated compounds were elucidated based on a detailed analysis of their NMR and MS data. The absolute configuration of the isolated compounds was determined by Electronic Circular Dichroism analysis coupled with computational methods. Aspergillinine A represents the first example of a diketopiperazine dipeptide containing the unnatural amino acid N-methyl kynurenine. Its absolute configuration revealed that it adopts a rather unusual conformation. Aspergillinine B represents a previously unencountered skeleton containing an isoindolinone ring. Aspergillinine C and D were similar to previously isolated diketopiperazine alkaloids, namely, lumpidin and brevianamide F, respectively. The diterpene pyrones were isolated twice previously, once from a soil-derived Aspergillus species, and once from the liquid culture of Aspergillus sp. HAB10R12. The alkaloids isolated in this study showed no antiproliferative activity when tested against HepG2 and A549 cancer cell lines. © 2023 Elsevier Ltd
تدمد:319422
DOI:10.1016/j.phytochem.2023.113685