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雪通内酯A - F：来自毛瓣金花茶（Roxb. Craib.）的高度氧化羊毛甾烷型和环阿尔廷烷型三萜类化合物

Xuetonglactones A-F: Highly Oxidized Lanostane and Cycloartane Triterpenoids From Roxb. Craib.

作者信息

Shehla Nuzhat, Li Bin, Cao Liang, Zhao Jianping, Jian Yuqing, Daniyal Muhammad, Wahab Atia-Tul, Khan Ikhlas A, Liao Duan-Fang, Rahman Atta-Ur, Choudhary M Iqbal, Wang Wei

机构信息

TCM and Ethnomedicine Innovation and Development International Laboratory, Academician Atta-ur-Rahman Belt and Road Traditional Medicine Research Center, School of Pharmacy, Hunan University of Chinese Medicine, Changsha, China.

International Center for Chemical and Biological Sciences, H. E. J. Research Institute of Chemistry, University of Karachi, Karachi, Pakistan.

出版信息

Front Chem. 2020 Jan 21;7:935. doi: 10.3389/fchem.2019.00935. eCollection 2019.

DOI:10.3389/fchem.2019.00935
PMID:32039154
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6990113/
Abstract

Xuetonglactones A-F (-), six unreported highly oxidized lanostane- and cycloartane-type triterpenoids along with 22 known scaffolds (-) were isolated from the stems of (Roxb.) Craib. Compared with previous congeners, xuetonglactone A (), possesses an unprecedented 20,21-α-epoxide, and xuetonglactone D () features an unusual 19-α-hydroperoxyl moiety. The structures and the absolute configurations of the compounds were established by extensive one- and two-dimensional NMR, and electronic circular dichroism (ECD) spectroscopic analysis, with those of and confirmed by single-crystal X-ray diffraction technique. Compounds and exhibited inhibition of iNOS activity in LPS-induced macrophages with IC values of 22.0, and 17.0 μg/mL, respectively. While compounds , , , and showed potent cytotoxic activities against human cervical cancer cell lines (HeLa) with the IC values of 4.0, 5.8, 5.0, and 6.4 μM, and against human gastric cancer cells (BGC 823) with the IC values of 2.0, 5.0, 2.5, and 2.0 μM, respectively. Moreover, plausible biogenetic pathways of (-) were also proposed.

摘要

从（Roxb.）Craib的茎中分离出雪通内酯A - F（-），六种未报道的高度氧化的羊毛甾烷型和环阿尔廷烷型三萜类化合物以及22种已知骨架（-）。与先前的同系物相比，雪通内酯A（）具有前所未有的20,21-α-环氧结构，雪通内酯D（）具有不寻常的19-α-氢过氧基部分。通过广泛的一维和二维核磁共振以及电子圆二色（ECD）光谱分析确定了这些化合物的结构和绝对构型，其中和的结构通过单晶X射线衍射技术得到证实。化合物和在脂多糖诱导的巨噬细胞中表现出对诱导型一氧化氮合酶（iNOS）活性的抑制作用，IC值分别为22.0和17.0μg/mL。而化合物、、、对人宫颈癌细胞系（HeLa）表现出较强的细胞毒活性，IC值分别为4.0、5.8、5.0和6.4μM，对人胃癌细胞（BGC 823）的IC值分别为2.0、5.0、2.5和2.0μM。此外，还提出了（-）可能的生源合成途径。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e51/6990113/88ada1cba2de/fchem-07-00935-g0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e51/6990113/711ba7aa80a8/fchem-07-00935-g0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e51/6990113/144b7937ba96/fchem-07-00935-g0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e51/6990113/d4f2f8824677/fchem-07-00935-g0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e51/6990113/4a87f919870d/fchem-07-00935-g0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e51/6990113/06d5c07cf0e7/fchem-07-00935-g0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e51/6990113/88ada1cba2de/fchem-07-00935-g0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e51/6990113/711ba7aa80a8/fchem-07-00935-g0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e51/6990113/144b7937ba96/fchem-07-00935-g0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e51/6990113/d4f2f8824677/fchem-07-00935-g0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e51/6990113/4a87f919870d/fchem-07-00935-g0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e51/6990113/06d5c07cf0e7/fchem-07-00935-g0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e51/6990113/88ada1cba2de/fchem-07-00935-g0005.jpg

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