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从海洋藻类相关真菌 LD-201810 中分离得到的细胞毒性次生代谢产物。

Cytotoxic Secondary Metabolites Isolated from the Marine Alga-Associated Fungus LD-201810.

机构信息

School of Life Sciences, Ludong University, Yantai 264025, China.

Shandong Provincial Key Laboratory of Quality Safty Monitoring and Risk Assessment for Animal Products, Ji'nan 250022, China.

出版信息

Mar Drugs. 2020 May 22;18(5):276. doi: 10.3390/md18050276.

DOI:10.3390/md18050276
PMID:32456085
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7281594/
Abstract

A new pentaketide derivative, penilactonol A (), and two new hydroxyphenylacetic acid derivatives, (2'R)-stachyline B (2) and (2'R)-westerdijkin A (3), together with five known metabolites, bisabolane-type sesquiterpenoids 4-6 and meroterpenoids 7 and 8, were isolated from the solid culture of a marine alga-associated fungus LD-201810. Their structures were elucidated based on extensive spectroscopic analyses, including 1D/2D NMR and high resolution electrospray ionization mass spectra (HRESIMS). The absolute configurations of the stereogenic carbons in 1 were determined by the (Mo(OAc))-induced circular dichroism (CD) and comparison of the calculated and experimental electronic circular dichroism (ECD) spectra, while the absolute configuration of the stereogenic carbon in 2 was established using single-crystal X-ray diffraction analysis. Compounds 2 and 3 adapt the 2'R-configuration as compared to known hydroxyphenylacetic acid-derived and O-prenylated natural products. The cytotoxicity of -8 against human carcinoma cell lines (A549, BT-549, HeLa, HepG2, MCF-7, and THP-1) was evaluated. Compound 3 exhibited cytotoxicity to the HepG2 cell line with an IC value of 22.0 μM. Furthermore, 5 showed considerable activities against A549 and THP-1 cell lines with IC values of 21.2 and 18.2 μM, respectively.

摘要

从一株海洋藻类共生真菌 LD-201810 的固体发酵产物中分离得到一个新的五肽衍生物 penilactonol A ()，两个新的 2'-羟基苯乙酸衍生物 (2'R)-stachyline B (2) 和 (2'R)-westerdijkin A (3)，以及五个已知代谢产物，倍半萜类 4-6 和 Meroterpenoids 7 和 8。基于广泛的光谱分析，包括 1D/2D NMR 和高分辨率电喷雾电离质谱 (HRESIMS)，确定了它们的结构。通过 (Mo(OAc))-诱导圆二色性 (CD) 和计算与实验电子圆二色性 (ECD) 光谱的比较，确定了 1 中手性碳原子的绝对构型，而 2 中手性碳原子的绝对构型则通过单晶 X 射线衍射分析确定。与已知的 2'-羟基苯乙酸衍生和 O-丙二烯基化天然产物相比，化合物 2 和 3 采用 2'R-构型。对 -8 对人癌细胞系（A549、BT-549、HeLa、HepG2、MCF-7 和 THP-1）的细胞毒性进行了评价。化合物 3 对 HepG2 细胞系具有细胞毒性，IC 值为 22.0 μM。此外，化合物 5 对 A549 和 THP-1 细胞系具有相当的活性，IC 值分别为 21.2 和 18.2 μM。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6d45/7281594/ae9a54944882/marinedrugs-18-00276-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6d45/7281594/d5019ca2e391/marinedrugs-18-00276-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6d45/7281594/76a50aabc9ef/marinedrugs-18-00276-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6d45/7281594/d8f0c8e20cb1/marinedrugs-18-00276-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6d45/7281594/4f650b5ff767/marinedrugs-18-00276-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6d45/7281594/ae9a54944882/marinedrugs-18-00276-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6d45/7281594/d5019ca2e391/marinedrugs-18-00276-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6d45/7281594/76a50aabc9ef/marinedrugs-18-00276-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6d45/7281594/d8f0c8e20cb1/marinedrugs-18-00276-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6d45/7281594/4f650b5ff767/marinedrugs-18-00276-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6d45/7281594/ae9a54944882/marinedrugs-18-00276-g005.jpg

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