G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-Letiya Vladivostoka, 159, Vladivostok 690022, Russia.
Institute of High Technologies and Advanced Materials, Far Eastern Federal University, 10 Ajax Bay, Russky Island, Vladivostok 690922, Russia.
Mar Drugs. 2023 Jul 29;21(8):431. doi: 10.3390/md21080431.
New anthraquinone derivatives acruciquinones A-C (-), together with ten known metabolites, were isolated from the obligate marine fungus KMM 4696. Acruciquinone C is the first member of anthraquinone derivatives with a 6/6/5 backbone. The structures of isolated compounds were established based on NMR and MS data. The absolute stereoconfigurations of new acruciquinones A-C were determined using ECD and quantum chemical calculations (TDDFT approach). A plausible biosynthetic pathway of the novel acruciquinone C was proposed. Compounds - and - showed a significant antimicrobial effects against growth, and acruciquinone A (), dendryol B (), coniothyrinone B (), and ω-hydroxypachybasin () reduced the activity of a key staphylococcal enzyme, sortase A. Moreover, the compounds, excluding , inhibited urease activity. We studied the effects of anthraquinones , , , and and coniothyrinone D () in an in vitro model of skin infection when HaCaT keratinocytes were cocultivated with . Anthraquinones significantly reduce the negative impact of on the viability, migration, and proliferation of infected HaCaT keratinocytes, and acruciquinone A () revealed the most pronounced effect.
从海洋真菌 KMM 4696 中分离得到了新的蒽醌衍生物 acruciquinones A-C（-）以及十个已知代谢物。Acruciquinone C 是具有 6/6/5 骨架的蒽醌衍生物的第一个成员。根据 NMR 和 MS 数据确定了分离化合物的结构。使用 ECD 和量子化学计算（TDDFT 方法）确定了新的 acruciquinones A-C 的绝对立体构型。提出了 novel acruciquinone C 的可能生物合成途径。化合物 - 和 - 对 生长表现出显著的抗菌作用，acruciquinone A (), dendryol B (), coniothyrinone B (), 和 ω-hydroxypachybasin () 降低了葡萄球菌关键酶 sortase A 的活性。此外，除了 之外，化合物还抑制了脲酶的活性。我们研究了蒽醌 、 、 、 和 coniothyrinone D () 在 HaCaT 角质形成细胞与 共培养的体外皮肤感染模型中的作用。蒽醌显著降低了 对感染的 HaCaT 角质形成细胞活力、迁移和增殖的负面影响，而 acruciquinone A () 则显示出最显著的效果。
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