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从(Blume)Spreng.(芸香科)中分离得到一种具有其他潜在生物活性次生代谢产物的新型天然化合物。

Isolation and Characterization of One New Natural Compound with Other Potential Bioactive Secondary Metabolites from (Blume) Spreng. (Family: Rutaceae).

机构信息

Department of Pharmaceutical Chemistry, University of Dhaka, Dhaka 1000, Bangladesh.

School of Cancer and Pharmaceutical Science, King's College London, 150 Stamford Street, London SE1 9NH, UK.

出版信息

Molecules. 2023 Feb 27;28(5):2207. doi: 10.3390/molecules28052207.

DOI:10.3390/molecules28052207
PMID:36903452
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10005784/
Abstract

(Blume) Spreng is a plant in the Rutaceae family and a species in the Glycosmis genus that has received little attention. Therefore, this research aimed to report the chemical and biological analysis of (Blume) Spreng. The chemical analysis involved the isolation and characterization of secondary metabolites through an extensive chromatographic study, and the structures of these metabolites were elucidated on the basis of a detailed analysis of NMR and HRESIMS spectroscopic data and by comparison with those of related compounds reported in the literature. Different partitions of the crude ethyl acetate (EtOAc) extract were evaluated for antioxidant, cytotoxic, and thrombolytic potentials. In chemical analysis, one new phenyl acetate derivative, namely 3,7,11,15-tetramethylhexadec-2-en-1-yl 2-phenylacetate (1), along with four known compounds N-methyl-3-(methylthio)-N-(2-phenylacetyl) acrylamide (2), penangin (3), β-Caryophyllene oxide (4), and acyclic diterpene-phytol (5) were isolated for the first time from the stem and leaf of the plant. The ethyl acetate fraction showed significant free radical scavenging activity with an IC value of 11.536 µg/mL compared to standard ascorbic acid (4.816 µg/mL). In the thrombolytic assay, the dichloromethane fraction showed the maximum thrombolytic activity of 16.42% but was still insignificant compared to the standard streptokinase (65.98%). Finally, in a brine shrimp lethality bioassay, the LC values of dichloromethane, ethyl acetate, and aqueous fractions were found to be 0.687 µg/mL, 0.805 µg/mL, and 0.982 µg/mL which are significant compared to the standard vincristine sulfate of 0.272 µg/mL.

摘要

Blume Spreng 是芸香科植物甘橘属的一种植物,目前研究较少。因此,本研究旨在报道 Blume Spreng 的化学和生物分析。化学分析涉及通过广泛的色谱研究分离和鉴定次生代谢产物,这些代谢产物的结构是基于对 NMR 和 HRESIMS 光谱数据的详细分析以及与文献中报道的相关化合物的比较来阐明的。粗乙酸乙酯(EtOAc)提取物的不同部分用于评估抗氧化、细胞毒性和溶栓潜力。在化学分析中,首次从该植物的茎和叶中分离得到一种新的苯乙酸酯衍生物,即 3,7,11,15-四甲基-2-烯-1-基 2-苯乙酸酯(1),以及四种已知化合物 N-甲基-3-(甲硫基)-N-(2-苯乙酰基)丙烯酰胺(2)、penangin(3)、β-石竹烯氧化物(4)和无环二萜植物醇(5)。与标准抗坏血酸(4.816μg/mL)相比,乙酸乙酯部分显示出显著的自由基清除活性,IC 值为 11.536μg/mL。在溶栓试验中,二氯甲烷部分显示出最大的溶栓活性,为 16.42%,但与标准链激酶(65.98%)相比仍不显著。最后,在盐水虾致死生物测定中,发现二氯甲烷、乙酸乙酯和水相部分的 LC 值分别为 0.687μg/mL、0.805μg/mL 和 0.982μg/mL,与标准硫酸长春新碱(0.272μg/mL)相比均具有显著差异。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f96e/10005784/41e9ed75dd4f/molecules-28-02207-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f96e/10005784/acac064fe67e/molecules-28-02207-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f96e/10005784/bfb06e80906f/molecules-28-02207-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f96e/10005784/b586335e6d6a/molecules-28-02207-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f96e/10005784/4f606f4efaa4/molecules-28-02207-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f96e/10005784/41e9ed75dd4f/molecules-28-02207-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f96e/10005784/acac064fe67e/molecules-28-02207-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f96e/10005784/bfb06e80906f/molecules-28-02207-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f96e/10005784/b586335e6d6a/molecules-28-02207-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f96e/10005784/4f606f4efaa4/molecules-28-02207-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f96e/10005784/41e9ed75dd4f/molecules-28-02207-g005.jpg

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