Identification and bioactivity evaluation of twelve previously undescribed depsidone derivatives from Garcinia oligantha

IF 3.2 2区生物学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY

Phytochemistry Pub Date : 2024-07-26 DOI:10.1016/j.phytochem.2024.114227

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Abstract

Phytochemical studies on the leaves and twigs of Garcinia oligantha Merr. led to the isolation of twelve previously undescribed depsidone derivatives (oliganthdepsidones A-L, 1–12). Their structures were elucidated by extensive spectroscopic analysis including ¹H and ¹³C NMR, HSQC, HMBC and NOESY along with HRESIMS. The structures of oliganthdepsidones G and J were finally determined using DFT-NMR chemical shift calculations and DP4+ methods. Cytotoxicity test in four human cancer cell lines indicated that oliganthdepsidone F had relatively strong cytotoxic effect against A375 (melanoma), A549 (lung cancer), HepG2 (liver cancer), and MCF-7 (breast cancer) cell lines with IC₅₀ of 18.71, 15.44, 10.92, and 15.90 μM, respectively. The dose- and time-dependent antiproliferative effects of oliganthdepsidone F on these cell lines were also observed by CCK-8 test. As determined by fluorescent microscopy and flow cytometry in these cell lines, oliganthdepsidone F could promote cell apoptosis, leading to the inhibition of cell proliferation. The results of wound healing assay and transwell assay showed that oliganthdepsidone F could inhibit the migration and invasion of A549 and MCF-7 cell lines in a concentration-dependent manner.

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鉴定和评估 12 种以前未曾描述过的来自寡甘草的去苷酮衍生物。

通过对鹅掌楸（Garcinia oligantha Merr.）的叶子和小枝进行植物化学研究，分离出了 12 种以前未曾描述过的去苷酮衍生物（oliganthdepsidones A-L，1-12）。通过广泛的光谱分析，包括 1H 和 13C NMR、HSQC、HMBC 和 NOESY 以及 HRESIMS，阐明了它们的结构。通过 DFT-NMR 化学位移计算和 DP4+ 方法，最终确定了低聚表苷酮 G 和 J 的结构。四种人类癌细胞株的细胞毒性测试表明，低聚庚二酮 F 对 A375（黑色素瘤）、A549（肺癌）、HepG2（肝癌）和 MCF-7（乳腺癌）细胞株具有较强的细胞毒性作用，IC50 分别为 18.71、15.44、10.92 和 15.90 μM。CCK-8 试验也观察到了低聚表西酮 F 对这些细胞株的剂量和时间依赖性抗增殖作用。通过荧光显微镜和流式细胞仪对这些细胞株的检测发现，低聚epsidone F能促进细胞凋亡，从而抑制细胞增殖。伤口愈合试验和透孔试验结果表明，低聚半乳糖苷酮 F 能以浓度依赖性方式抑制 A549 和 MCF-7 细胞株的迁移和侵袭。

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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.