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两种翼籽木属植物中的贝壳杉烷型二萜的晶体结构与细胞毒性

Crystal Structures and Cytotoxicity of ent-Kaurane-Type Diterpenoids from Two Aspilia Species.

机构信息

Department of Chemistry, University of Nairobi, P. O. Box 30197, 00100 Nairobi, Kenya.

Department of Chemistry, University of Jyvaskyla, P.O. Box 35, 40014 Jyvaskyla, Finland.

出版信息

Molecules. 2018 Dec 4;23(12):3199. doi: 10.3390/molecules23123199.

DOI:10.3390/molecules23123199
PMID:30518152
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6321058/
Abstract

A phytochemical investigation of the roots of led to the isolation of -kaurane-type diterpenoids and additional phytochemicals (⁻). The structures of the isolated compounds were elucidated based on Nuclear Magnetic Resonance (NMR) spectroscopic and mass spectrometric analyses. The absolute configurations of seven of the -kaurane-type diterpenoids (⁻, and ) were determined by single crystal X-ray diffraction studies. Eleven of the compounds were also isolated from the roots and the aerial parts of . The literature NMR assignments for compounds and were revised. In a cytotoxicity assay, 12α-methoxy--kaur-9(11),16-dien-19-oic acid () (IC = 27.3 ± 1.9 µM) and 9β-hydroxy-15α-angeloyloxy--kaur-16-en-19-oic acid () (IC = 24.7 ± 2.8 µM) were the most cytotoxic against the hepatocellular carcinoma (Hep-G2) cell line, while 15α-angeloyloxy-16β,17-epoxy--kauran-19-oic acid () (IC = 30.7 ± 1.7 µM) was the most cytotoxic against adenocarcinomic human alveolar basal epithelial (A549) cells.

摘要

对 led 的根部进行植物化学研究,分离得到了 -kaurane 型二萜类化合物和其他植物化学物质(⁻)。根据核磁共振(NMR)光谱和质谱分析确定了分离化合物的结构。通过单晶 X 射线衍射研究确定了七种 -kaurane 型二萜类化合物(⁻、和 )的绝对构型。从根和地上部分也分离出了 11 种化合物。还修订了化合物 和 的文献 NMR 分配。在细胞毒性测定中,12α-甲氧基--kaur-9(11),16-二烯-19-酸()(IC = 27.3 ± 1.9 µM)和 9β-羟基-15α-angeloyloxy--kaur-16-烯-19-酸()(IC = 24.7 ± 2.8 µM)对肝癌(Hep-G2)细胞系的细胞毒性最强,而 15α-angeloyloxy-16β,17-epoxy--kauran-19-oic 酸()(IC = 30.7 ± 1.7 µM)对腺癌细胞(A549)的细胞毒性最强。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/485a/6321058/cbcfb23038a9/molecules-23-03199-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/485a/6321058/f6d867add856/molecules-23-03199-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/485a/6321058/708f296374c3/molecules-23-03199-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/485a/6321058/d0bf5807c1e1/molecules-23-03199-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/485a/6321058/cbcfb23038a9/molecules-23-03199-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/485a/6321058/f6d867add856/molecules-23-03199-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/485a/6321058/708f296374c3/molecules-23-03199-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/485a/6321058/d0bf5807c1e1/molecules-23-03199-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/485a/6321058/cbcfb23038a9/molecules-23-03199-g004.jpg

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