Seven new 4-hydroxy-6-phenyl-2H-pyran-2-one (HPPO) derived meroterpenoids, 1-methyl-12a,12b-epoxyarisugacin M (1), 1-methyl-4a,12b-epoxyarisugacin M (2), 2,3-dihydroxy-3,4a-epoxy-12a-dehydroxyisoterreulactone A (3), 2-hydroxy-12a-dehydroxyisoterreulactone A (4), 3′-demethoxyterritrems B′ (5), 4a-hydroxyarisugacin P (6), and 1-epi-arisugacin H (7), together with two known analogues (8 and 9), were isolated from the marine-derived fungal strain Penicillium sp. SCSIO 41691. Their structures were elucidated by spectroscopic methods, and the absolute configurations of compounds 1 and 3 were determined by single-crystal X-ray diffraction. Among them, 1 and 2 had a unique methyl migration in the basic meroterpenoid skeleton with a 12a,12b-epoxy or 4a,12b-epoxy group, and 3 was a highly oxygenated HPPO-derived meroterpenoid featuring a rare 6/5/6/6/6/6 hexacyclic system with a 3,4a-epoxy group. Biologically, 5 exhibited inhibitory activity against lipopolysaccharide-induced nitric oxide production in RAW 264.7 cells with an IC₅₀ value of 21 μM, more potent than the positive control indomethacin.

中文翻译：

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来自海洋源性真菌青霉属的 HPPO 衍生的类萜。 SCSIO 41691

七个新的 4-羟基-6-苯基-2 H-吡喃-2-酮 (HPPO) 衍生的类萜，1-甲基-12a,12b-环氧阿里糖星 M ( 1 )，1-甲基-4a,12b-环氧阿里糖星 M ( 2 ), 2,3-二羟基-3,4a-环氧-12a-脱羟基异土内酯 A ( 3 ), 2-羟基-12a-脱羟基异土内酯 A ( 4 ), 3'-demethoxyterritrems B' ( 5 ), 4a-羟基阿里糖星 P ( 6 ) 和 1-epi-arisugacin H ( 7 ) 以及两种已知的类似物（8和9）是从海洋来源的真菌菌株青霉中分离出来的。 SCSIO 41691。通过光谱方法阐明了它们的结构，并通过单晶X射线衍射确定了化合物1和3的绝对构型。其中，1和2在具有12a,12b-环氧基或4a,12b-环氧基团的基本类萜骨架中具有独特的甲基迁移，3是高度氧化的HPPO衍生的类萜，具有罕见的6/5/6/具有3,4a-环氧基团的6/6/6六环系统。从生物学角度来看，5对 RAW 264.7 细胞中脂多糖诱导的一氧化氮产生具有抑制活性，IC ₅₀值为 21 μM，比阳性对照吲哚美辛更有效。