Ent-16β,17-dihydroxy-kauran-19-oic acid (DKA), a kaurane diterpenoid from Sigesbeckia pubescens(Makino) Makino, inhibits the migration of MDA-MB-231 breast cancer

IF 1.9 3区化学 Q3 CHEMISTRY, APPLIED Natural Product Research Pub Date : 2025-02-16 DOI:10.1080/14786419.2023.2287177

Jianbin Wang , Rongxin Liu , Hao Chen , Anqi Chen , Li Chen

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Abstract

Ent-kaurane diterpenoids were studied as a biologically active ingredient group of Sigesbeckia pubescens (Makino) Makino. Here, five known ent-kaurane diterpenoids were isolated and identified, named ent-16β,17-dihydroxy-kauran-19-oic acid (1), ent-16β,17-dihydroxy-kauran-19-oate (2), ent-18-acetoxy-17-hydroxykauran-19-oic acid (3), ent-16β,17,18-trihydroxy-kauran-19 -oic acid (4), and ent-17-hydroxy-kauran-16βH-19-oic acid (5). Their inhibitory effects of these compounds on MDA-MB-231 breast cancer migration were firstly tested in a chemotaxis invasion assay. Among them, compound 1 (DKA) showed superior inhibitory activities with IC₅₀ value of 1.96 µM. Then, a wound healing assay and BALB/c nude mice were used for further studying the inhibitory activity of DKA on MDA-MB-231 breast cancer migration in vitro and in vivo, respectively. The wound healing assay showed that DKA (1, 5, and 25 μM) can significantly inhibit cell migration and the mouse model of lung metastasis showed that DKA (2.5, 5, and 10 mg/kg) could strongly suppress the lung metastasis of MDA-MB-231 breast cancer cells.

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Ent-16β，17-二羟基-山核桃-19-酸(DKA)是一种来自Sigesbeckia pubescens(Makino) Makino的山核桃烷二萜类物质，可抑制MDA-MB-231乳腺癌的迁移。

对正戊烷二萜进行了生物活性研究。本研究分离鉴定了5种已知的对kauran二萜类化合物，分别命名为:t-16β、17-二羟基kauran-19-oic酸(1)、t-16β、17-二羟基kauran-19-oic酸(2)、t-18-乙酰氧基-17-羟基kauran-19-oic酸(3)、t-16β、17,18-三羟基kauran-19-oic酸(4)和t-17-羟基kauran-16 - β h -19-oic酸(5)。通过趋化性侵袭实验，首次检测了这些化合物对MDA-MB-231乳腺癌迁移的抑制作用。其中化合物1 (DKA)的IC50值为1.96µM，具有较强的抑制活性。通过伤口愈合实验和BALB/c裸鼠实验，进一步研究DKA对MDA-MB-231乳腺癌迁移的体外和体内抑制作用。伤口愈合实验显示，DKA(1、5和25 μM)能显著抑制细胞迁移，肺转移小鼠模型显示，DKA(2.5、5和10 mg/kg)能强烈抑制MDA-MB-231乳腺癌细胞的肺转移。

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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.