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马齿苋中阿魏酰酰胺的紫外光转化及其对白细胞介素-6诱导的信号转导和转录激活因子3激活的抑制作用研究。

Study of the UV Light Conversion of Feruloyl Amides from Portulaca oleracea and Their Inhibitory Effect on IL-6-Induced STAT3 Activation.

作者信息

Hwang Joo Tae, Kim Yesol, Jang Hyun-Jae, Oh Hyun-Mee, Lim Chi-Hwan, Lee Seung Woong, Rho Mun-Chual

机构信息

Natural Product Research Center, Korea Research Institute of Bioscience and Biotechnology, 181 Ipsin-gil, Jeongeup-si, Jeonbuk 56212, Korea.

College of Agriculture and Life Sciences, Chungnam National University, 99 Daehak-ro, Yuseong-gu, Daejeon 300-764, Korea.

出版信息

Molecules. 2016 Jun 30;21(7):865. doi: 10.3390/molecules21070865.

DOI:10.3390/molecules21070865
PMID:27376259
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6273636/
Abstract

Two new feruloyl amides, N-cis-hibiscusamide (5) and (7'S)-N-cis-feruloylnormetanephrine (9), and eight known feruloyl amides were isolated from Portulaca oleracea L. and the geometric conversion of the ten isolated feruloyl amides by UV light was verified. The structures of the feruloyl amides were determined based on spectroscopic data and comparison with literature data. The NMR data revealed that the structures of the isolated compounds showed cis/trans-isomerization under normal laboratory light conditions. Therefore, cis and trans-isomers of feruloyl amides were evaluated for their convertibility and stability by UV light of a wavelength of 254 nm. After 96 h of UV light exposure, 23.2%-35.0% of the cis and trans-isomers were converted to trans-isomers. Long-term stability tests did not show any significant changes. Among all compounds and conversion mixtures collected, compound 6 exhibited the strongest inhibition of IL-6-induced STAT3 activation in Hep3B cells, with an IC50 value of 0.2 μM. This study is the first verification of the conversion rates and an equilibrium ratio of feruloyl amides. These results indicate that this natural material might provide useful information for the treatment of various diseases involving IL-6 and STAT3.

摘要

从马齿苋中分离出两种新的阿魏酰酰胺，即N-顺式木槿酰胺（5）和（7'S）-N-顺式阿魏酰去甲肾上腺素（9），以及八种已知的阿魏酰酰胺，并验证了十种分离出的阿魏酰酰胺在紫外光下的几何构型转化。基于光谱数据并与文献数据进行比较确定了阿魏酰酰胺的结构。核磁共振数据表明，分离出的化合物的结构在正常实验室光照条件下会发生顺/反异构化。因此，通过波长为254 nm的紫外光评估了阿魏酰酰胺顺式和反式异构体的可转化性和稳定性。紫外光照射96小时后，23.2%-35.0%的顺式和反式异构体转化为反式异构体。长期稳定性测试未显示任何显著变化。在收集的所有化合物和转化混合物中，化合物6对Hep3B细胞中IL-6诱导的STAT3激活表现出最强的抑制作用，IC50值为0.2μM。本研究首次验证了阿魏酰酰胺的转化率和平衡比。这些结果表明，这种天然物质可能为治疗涉及IL-6和STAT3的各种疾病提供有用信息。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a40/6273636/c5b97988844b/molecules-21-00865-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a40/6273636/e9ec716ae32d/molecules-21-00865-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a40/6273636/2dfd90d7c1ca/molecules-21-00865-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a40/6273636/1f809695a21c/molecules-21-00865-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a40/6273636/f5ea722f2144/molecules-21-00865-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a40/6273636/c5b97988844b/molecules-21-00865-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a40/6273636/e9ec716ae32d/molecules-21-00865-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a40/6273636/2dfd90d7c1ca/molecules-21-00865-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a40/6273636/1f809695a21c/molecules-21-00865-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a40/6273636/f5ea722f2144/molecules-21-00865-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a40/6273636/c5b97988844b/molecules-21-00865-g005.jpg

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