Eight phenalenone derivatives, including four new compounds, aceneoherqueinones A and B (1 and 2), (+)-aceatrovenetinone A (3a), and (+)-aceatrovenetinone B (3d), along with four known congeners, (–)-aceatrovenetinone A (3b), (–)-aceatrovenetinone B (3c), (–)-scleroderolide (4a), and (+)-scleroderolide (4b), were characterized from the marine mangrove-derived fungus Penicillium herquei MA-370. Among them, compounds 1 and 2 are rare phenalenone derivatives featuring cyclic ether unit between C-5 and C-2’. All of these compounds were subjected to chiral HPLC analysis, and the unstable stereoisomers 3a–3d, containing configurationally labile chirality centers, were characterized by online HPLC-ECD measurements supported with TDDFT-ECD calculations. The structures of these compounds were elucidated by detailed analysis of their NMR and mass spectroscopic data, and the absolute configuration of compound 1 was confirmed by X-ray diffraction analysis, while those of compounds 2 and 3a–3d were determined by TDDFT-ECD calculations of their ECD spectra. All of the isolated compounds were tested for the inhibitory activity against angiotensin-I-converting enzyme (ACE), and compounds 1 and 2 displayed activity with IC₅₀ values 3.10 and 11.28 μM, respectively. The intermolecular interaction and potential binding sites of 1 and 2 with ACE were elaborated by molecular docking, showing that compound 1 bound well with ACE via hydrogen interactions with residues Ala261, Gln618, Trp621, and Asn624, while compound 2 interacted with residues Asp358 and Tyr360.

八种苯酚衍生物，包括四种新化合物，aceeoherqueinones A 和 B（1和2）、(+)-aceatrovenetinone A ( 3a ) 和 (+)-aceatrovenetinone B ( 3d )，以及四种已知的同系物，(–)-乙酰维维酮 A ( 3b )、(–)-乙酰维维酮 B ( 3c )、 (–)-硬皮内酯( 4a ) 和 (+)-硬皮内酯( 4b ) 是从海洋红树林衍生的真菌Penicillium herquei MA-370 中表征的。其中，化合物1和2是稀有的苯甲酮衍生物，在 C-5 和 C-2' 之间具有环醚单元。所有这些化合物都进行了手性 HPLC 分析，不稳定的立体异构体3a-3d包含构型不稳定的手性中心，通过在线 HPLC-ECD 测量进行表征，并支持 TDDFT-ECD 计算。这些化合物的结构通过核磁共振和质谱数据的详细分析得到阐明，化合物1的绝对构型由 X 射线衍射分析证实，而化合物2和3a-3d的绝对构型由其 ECD 谱的 TDDFT-ECD 计算确定。测试了所有分离的化合物对血管紧张素-I 转换酶 (ACE) 的抑制活性，化合物1和2 的IC ₅₀值分别为 3.10 和 11.28 μM。通过分子对接详细阐述了1和2与 ACE的分子间相互作用和潜在结合位点，表明化合物1通过与残基 Ala261、Gln618、Trp621 和 Asn624 的氢相互作用与 ACE 结合良好，而化合物2与残基 Asp358 和 Tyr360 相互作用.