Cytotoxic Synurins A–C: Chlorinated Naphthoquinone Pigments from the Freshwater Alga Synura sphagnicola

IF 3.7 2区生物学 Q2 CHEMISTRY, MEDICINAL

Journal of Natural Products Pub Date : 2026-06-26 Epub Date: 2026-05-26 DOI:10.1021/acs.jnatprod.6c00417

Magda Škaloudová, Jan Blahut, Jan Hájek, Alan Kádek, Peter Mojzeš, Jana Pilátová, Dominika Tučková, Petra Divoká, Antonín Střížek, Martin Lukeš, Eva Kotabová, Petra Bittnerová, Kumar Saurav, Pavel Hrouzek and Petra Urajová*,

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引用次数: 0

Abstract

Synura sphagnicola, a peat bog chrysophyte, forms conspicuous red cytoplasmic droplets. These droplets previously showed an unidentified pigment, prompting a detailed chemical investigation. Large-scale cultivation and chromatographic purification yielded three structurally related orange-to-red compounds, previously undescribed chlorinated naphthoquinone pigments─synurin A (1), synurin B (2), and synurin C (3)─whose identities were established using HPLC-HRMS, FT-ICR MS, NMR spectroscopy, FTIR, fluorescence spectroscopy, and Raman microscopy. The compounds were identified as 2,3-dichloro-5,8-dihydroxy-6-propylnaphthalene-1,4-dione (1) and its two O-methylated regioisomers (2, 3). Raman spectra revealed strong environment-dependent vibrational differences, particularly for 1 and 2. In vitro assays demonstrated potent but nonselective cytotoxicity toward cancerous and nontransformed cell lines (IC₅₀ in the low micromolar range), while only 1 exhibited ferric-reducing antioxidant activity.

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细胞毒性Synurins A-C：来自淡水藻藻的氯化萘醌色素。

泥炭沼泽绿藻，形成明显的红色胞质液滴。这些液滴之前显示出一种未知的色素，促使人们进行了详细的化学研究。大规模培养和色谱纯化得到了三种结构相关的橘红色化合物，即以前未描述过的氯化萘醌色素─synurin A(1)、synurin B(2)和synurin C(3)─其身份通过HPLC-HRMS、FT-ICR MS、NMR波谱、FTIR、荧光光谱和拉曼显微镜确定。这些化合物被鉴定为2,3-二氯-5,8-二羟基-6-丙基萘-1,4-二酮(1)及其两个o-甲基化区域异构体（2,3）。拉曼光谱显示出强烈的环境相关振动差异，特别是1和2。体外实验显示对癌性和非转化细胞系有强而非选择性的细胞毒性（IC50在低微摩尔范围内），而只有1种表现出铁还原的抗氧化活性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Journal of Natural Products 生物-药学

CiteScore

9.10

自引率

5.90%

发文量

294

审稿时长

2.3 months

期刊介绍： The Journal of Natural Products invites and publishes papers that make substantial and scholarly contributions to the area of natural products research. Contributions may relate to the chemistry and/or biochemistry of naturally occurring compounds or the biology of living systems from which they are obtained. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin. When new compounds are reported, manuscripts describing their biological activity are much preferred. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.