Cytotoxic evaluation of new polyhydroxylated steroids from the Red Sea soft coral Litophyton mollis (Macfadyen, 1936)

IF 1.9 3区化学 Q3 CHEMISTRY, APPLIED Natural Product Research Pub Date : 2023-11-14 DOI:10.1080/14786419.2023.2284259

Ahmed H. Eissa , Asmaa M. Abdel-Tawab , El Sayed A.E. Hamed , Fawzia Z. El-Ablack , Seif-Eldin N. Ayyad

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Abstract

An efficient column chromatography of the CH₂Cl₂/MeOH crude extract from the soft coral Litophyton mollis (Macfadyen, 1936) yielded seven steroids, including five 4α-methylated steroids (1–5) and two 19-oxygenated steroids (6–7). Notably, both compounds 3 and 7 are new, identified as (22E)-4α,24-dimethyl-5α-cholesta-22,24(28)-dien-3β,8β-diol (3) and (22E,24R)-7β-acetoxy-24-methyl-cholesta-5,22-dien-3β,19-diol (7). The chemical structures and relative configurations were elucidated through comprehensive spectroscopic analyses, including 1D and 2D NMR, as well as HRESIMS analysis. The cytotoxicity of metabolites 1–7 was evaluated against three cancer cell lines: MCF-7, HepG2, and NCI-1299. Remarkably, metabolites 6 and 7 exhibited strong cytotoxic activity against MCF-7, with IC₅₀ values of 8.6 and 8.4 μM, respectively, while also showing moderate effects against NCI-1299, with IC₅₀ values of 15.7 and 15.1 μM, respectively. Additionally, steroids 4 and 5 displayed weak cytotoxicity against all three cell lines, with IC₅₀ values in the ranges of 34.7–37.5 and 30.8–46.3 μM, respectively.

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来自红海软珊瑚Litophyton mollis的新型多羟基类固醇的细胞毒性评价(Macfadyen, 1936)。

对软珊瑚Litophyton mollis (Macfadyen, 1936)的CH2Cl2/MeOH粗提取物进行高效柱层析，得到7种类固醇，包括5种4α-甲基化类固醇(1-5)和2种19-氧合类固醇(6-7)。值得注意的是，化合物3和7都是新化合物，鉴定为(22E)-4α，24-二甲基-5α-胆固醇-22,24(28)-二烯-3β，8β-二醇(3)和(22E,24R)-7β-乙酰氧基-24-甲基-胆固醇-5,22-二烯-3β，19-二醇(7)。通过综合光谱分析，包括1D和2D NMR以及hresms分析，确定了它们的化学结构和相对构型。代谢产物1-7对三种癌细胞系MCF-7、HepG2和NCI-1299的细胞毒性进行了评估。值得注意的是，代谢物6和7对MCF-7的IC50值分别为8.6和8.4 μM，对NCI-1299的IC50值分别为15.7和15.1 μM，也表现出较强的细胞毒活性。此外，甾体激素4和5对三种细胞系均表现出较弱的细胞毒性，IC50值分别在34.7 ~ 37.5 μM和30.8 ~ 46.3 μM之间。

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来源期刊

Natural Product Research 化学-医药化学

CiteScore

5.10

自引率

9.10%

发文量

605

审稿时长

2.1 months

期刊介绍： The aim of Natural Product Research is to publish important contributions in the field of natural product chemistry. The journal covers all aspects of research in the chemistry and biochemistry of naturally occurring compounds. The communications include coverage of work on natural substances of land and sea and of plants, microbes and animals. Discussions of structure elucidation, synthesis and experimental biosynthesis of natural products as well as developments of methods in these areas are welcomed in the journal. Finally, research papers in fields on the chemistry-biology boundary, eg. fermentation chemistry, plant tissue culture investigations etc., are accepted into the journal. Natural Product Research issues will be subtitled either ""Part A - Synthesis and Structure"" or ""Part B - Bioactive Natural Products"". for details on this , see the forthcoming articles section. All manuscript submissions are subject to initial appraisal by the Editor, and, if found suitable for further consideration, to peer review by independent, anonymous expert referees. All peer review is single blind and submission is online via ScholarOne Manuscripts.