从Aspergillus sp. HAB10R12的土豆葡萄糖琼脂（PDA）培养基中分离出四种前未描述过的生物碱（aspergillinine A-D）和四种已知的二萜吡喃。基于对其NMR和MS数据的详细分析，阐明了所分离化合物的化学结构。同时，通过电子环状二色性分析结合计算方法确定了分离化合物的绝对构型。其中Aspergillinine A是第一个含有非天然胺基N-甲基犬尿酸二肽的二酮脯氨酸肽的例子。其绝对构型揭示它采用了相当不寻常的构型。Aspergillinine B则代表着先前未发现的含异吲哚啉酮环的骨架。而Aspergillinine C和D与已分离的二肽生物碱，lumpidin和brevianamide F，相似。这些二萜吡喃曾于先前两次从土壤衍生的Aspergillus菌株和Aspergillus sp. HAB10R12的液体培养物中分离出。本研究分离出的生物碱在对HepG2和A549癌细胞株进行抗增殖活性测试时未表现出活性。版权所有© 2023 Elsevier Ltd.

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.Copyright © 2023. Published by Elsevier Ltd.