Antiviral prenylated C₆-C₃ derivatives containing a methylenedioxyl group from the roots of Illicium brevistylum.

IF 3.2 2区生物学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY Phytochemistry Pub Date : 2025-03-04 DOI:10.1016/j.phytochem.2025.114462

Jing-Yu Zhang, Qian-Ru Wang, Hui-Lin Yang, Rong-Mei Gao, Mi Li, Jia Yang, Yu-Huan Li, Li Li, Shuang-Gang Ma

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Abstract

Five previously undescribed prenylated C₆-C₃ compounds (1-3 and 5-6) and four known prenylated C₆-C₃ compounds (4 and 7-9) were isolated from the roots of Illicium brevistylum A. C. Smith. Their structures were elucidated using extensive spectroscopic analyses, including HRESIMS, NMR (¹H and ¹³C NMR, ¹H-¹H COSY, HSQC, HMBC and NOESY), and CD spectra, ECD calculations, and NOE difference experiments. The absolute configurations of 1-3 were further determined using the modified Mosher's method. All the isolates were evaluated for their antiviral activity against Coxsackievirus B3 and influenza virus A/Hanfang/359/95, their anti-inflammatory potential for nitric oxide generation in lipopolysaccharide-stimulated RAW264.7 and BV2 cells, and their cytotoxicity against the HGC27, T98G, HepG2, A549 and MCF-7 cell lines. Compounds 1-2, 5, and 7-8 exhibited moderate activity against CVB3, whereas all the isolates displayed weak anti-inflammatory effects and no significant cytotoxicity.

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从Illicium brevistylum根中提取的含有亚甲基二氧基的抗病毒前烯化C6-C3衍生物。

从 Illicium brevistylum A. C. Smith 的根中分离出了五种以前未曾描述过的前烯化 C6-C3 化合物（1-3 和 5-6）和四种已知的前烯化 C6-C3 化合物（4 和 7-9）。通过广泛的光谱分析，包括 HRESIMS、NMR（1H 和 13C NMR、1H-1H COSY、HSQC、HMBC 和 NOESY）、CD 光谱、ECD 计算和 NOE 差分实验，阐明了它们的结构。使用改进的莫舍方法进一步确定了 1-3 的绝对构型。评估了所有分离物对柯萨奇病毒 B3 和流感病毒 A/HANfang/359/95 的抗病毒活性、在脂多糖刺激的 RAW264.7 和 BV2 细胞中产生一氧化氮的抗炎潜力，以及对 HGC27、T98G、HepG2、A549 和 MCF-7 细胞系的细胞毒性。化合物 1-2、5 和 7-8 对 CVB3 表现出中等程度的活性，而所有分离物均表现出微弱的抗炎作用，没有明显的细胞毒性。

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来源期刊

Phytochemistry 生物-植物科学

CiteScore

6.40

自引率

7.90%

发文量

443

审稿时长

39 days

期刊介绍： Phytochemistry is a leading international journal publishing studies of plant chemistry, biochemistry, molecular biology and genetics, structure and bioactivities of phytochemicals, including ''-omics'' and bioinformatics/computational biology approaches. Phytochemistry is a primary source for papers dealing with phytochemicals, especially reports concerning their biosynthesis, regulation, and biological properties both in planta and as bioactive principles. Articles are published online as soon as possible as Articles-in-Press and in 12 volumes per year. Occasional topic-focussed special issues are published composed of papers from invited authors.