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Gerardiins A–L and Structurally Related Phenanthrenes from the Halophyte Plant Juncus gerardii and Their Cytotoxicity against Triple-Negative Breast Cancer Cells
Journal of Natural Products ( IF 3.3 ) Pub Date : 2020-10-14 , DOI: 10.1021/acs.jnatprod.0c00631 Dóra Stefkó 1 , Norbert Kúsz 1 , Anita Barta 1 , Zoltán Kele 2 , László Bakacsy 3 , Ágnes Szepesi 3 , Csilla Fazakas 4 , Imola Wilhelm 4, 5 , István A Krizbai 4, 5 , Judit Hohmann 1, 6 , Andrea Vasas 1
Journal of Natural Products ( IF 3.3 ) Pub Date : 2020-10-14 , DOI: 10.1021/acs.jnatprod.0c00631 Dóra Stefkó 1 , Norbert Kúsz 1 , Anita Barta 1 , Zoltán Kele 2 , László Bakacsy 3 , Ágnes Szepesi 3 , Csilla Fazakas 4 , Imola Wilhelm 4, 5 , István A Krizbai 4, 5 , Judit Hohmann 1, 6 , Andrea Vasas 1
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Species in the Juncaceae accumulate different types of secondary metabolites, among them phenanthrenes and 9,10-dihydrophenanthrenes in substantial amounts. These compounds have chemotaxonomic significance and also possess interesting pharmacological activities. The present study has focused on the isolation, structure determination, and pharmacological investigation of phenanthrenes from Juncus gerardii. Twenty-six compounds, including 23 phenanthrenes, have been isolated from a methanol extract of this plant. Twelve compounds, the phenanthrenes gerardiins A–L (1–12), were obtained as new natural products. Eleven phenanthrenes [effusol (13), dehydroeffusol (14), effususin A (15), compressin A, 7-hydroxy-2-methoxy-1-methyl-5-vinyl-9,10-dihydrophenanthrene, juncusol, 2-hydroxy-7-hydroxymethyl-1-methyl-5-vinyl-9,10-dihydrophenanthrene, 2,7-dihydroxy-5-formyl-1-methyl-9,10-dihydrophenanthrene, effususol A, 2,7-dihydroxy-5-hydroxymethyl-1-methyl-9,10-dihydrophenanthrene, and jinflexin C], 1-O-p-coumaroyl-3-O-feruloyl-glycerol, and the flavones apigenin and luteolin were isolated for the first time from this plant. The cytotoxicity of the 23 isolated phenanthrenes in both mouse (4T1) and human (MDA-MB-231) triple-negative breast cancer cells and in a nontumor (D3, human cerebral microvascular endothelial) cell line was tested using an MTT viability assay. The results obtained showed that the dimeric compounds gerardiins I (9), J (10), K (11), and L (12), derived biogenetically from effusol and dehydroeffusol, were cytotoxic to both tumor and nontumor cell lines, while the monomeric compounds exerted no or very low cytotoxicity. Impedance measurements were consistent with the results of the MTT assays performed.
中文翻译：
来自盐生植物 Juncus gerardii 的 Gerardiins A-L 和结构相关的菲及其对三阴性乳腺癌细胞的细胞毒性
Juncaceae 中的物种积累了不同类型的次生代谢物，其中大量的菲和 9,10-二氢菲。这些化合物具有化学分类学意义并且还具有有趣的药理活性。目前的研究重点是来自Juncus gerardii的菲的分离、结构测定和药理研究。已从该植物的甲醇提取物中分离出 26 种化合物，包括 23 种菲。12 种化合物，菲属gerardiins A–L ( 1 – 12 )，作为新的天然产物获得。十一种菲 [effusol ( 13 ), dehydroeffusol ( 14 ), effususin A ( 15 )), compressin A, 7-羟基-2-甲氧基-1-甲基-5-乙烯基-9,10-二氢菲, juncusol, 2-羟基-7-羟基甲基-1-甲基-5-乙烯基-9,10-二氢菲, 2,7-dihydroxy-5-formyl-1-methyl-9,10-dihydrophenanthrene, effususol A, 2,7-dihydroxy-5-hydroxymethyl-1-methyl-9,10-dihydrophenanthrene, and jinflexin C], 1 - O - p -coumaroyl-3- O -feruloyl-glycerol, 以及黄酮类芹菜素和木犀草素是首次从该植物中分离得到。使用 MTT 活力测定法测试了 23 种分离的菲在小鼠 (4T1) 和人 (MDA-MB-231) 三阴性乳腺癌细胞和非肿瘤（D3，人脑微血管内皮）细胞系中的细胞毒性。所得结果表明二聚化合物gerardiins I ( 9)、J ( 10 )、 K ( 11 ) 和 L ( 12 )，从 effusol 和 dehydroeffusol 生物遗传学衍生，对肿瘤和非肿瘤细胞系都有细胞毒性，而单体化合物没有或非常低的细胞毒性。阻抗测量与所进行的 MTT 测定的结果一致。
更新日期：2020-10-26
中文翻译：
来自盐生植物 Juncus gerardii 的 Gerardiins A-L 和结构相关的菲及其对三阴性乳腺癌细胞的细胞毒性
Juncaceae 中的物种积累了不同类型的次生代谢物，其中大量的菲和 9,10-二氢菲。这些化合物具有化学分类学意义并且还具有有趣的药理活性。目前的研究重点是来自Juncus gerardii的菲的分离、结构测定和药理研究。已从该植物的甲醇提取物中分离出 26 种化合物，包括 23 种菲。12 种化合物，菲属gerardiins A–L ( 1 – 12 )，作为新的天然产物获得。十一种菲 [effusol ( 13 ), dehydroeffusol ( 14 ), effususin A ( 15 )), compressin A, 7-羟基-2-甲氧基-1-甲基-5-乙烯基-9,10-二氢菲, juncusol, 2-羟基-7-羟基甲基-1-甲基-5-乙烯基-9,10-二氢菲, 2,7-dihydroxy-5-formyl-1-methyl-9,10-dihydrophenanthrene, effususol A, 2,7-dihydroxy-5-hydroxymethyl-1-methyl-9,10-dihydrophenanthrene, and jinflexin C], 1 - O - p -coumaroyl-3- O -feruloyl-glycerol, 以及黄酮类芹菜素和木犀草素是首次从该植物中分离得到。使用 MTT 活力测定法测试了 23 种分离的菲在小鼠 (4T1) 和人 (MDA-MB-231) 三阴性乳腺癌细胞和非肿瘤（D3，人脑微血管内皮）细胞系中的细胞毒性。所得结果表明二聚化合物gerardiins I ( 9)、J ( 10 )、 K ( 11 ) 和 L ( 12 )，从 effusol 和 dehydroeffusol 生物遗传学衍生，对肿瘤和非肿瘤细胞系都有细胞毒性，而单体化合物没有或非常低的细胞毒性。阻抗测量与所进行的 MTT 测定的结果一致。
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