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环阿屯烷型三萜酸类化合物对生物膜和群体感应的抑制作用来自喀麦隆草原蜂胶:粗提取物的酚类成分分析及抗氧化活性。

Antibiofilm and Anti-Quorum Sensing Potential of Cycloartane-Type Triterpene Acids from Cameroonian Grassland Propolis: Phenolic Profile and Antioxidant Activity of Crude Extract.

机构信息

School of Chemical Engineering and Mineral Industries, University of Ngaoundere, Ngaoundere 454, Cameroon.

Food Quality Control and Analysis Program, Ula Ali Kocman Vocational School, Mugla Sitki Kocman University, Mugla 48147, Turkey.

出版信息

Molecules. 2022 Jul 29;27(15):4872. doi: 10.3390/molecules27154872.

DOI:10.3390/molecules27154872
PMID:35956824
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9369644/
Abstract

Propolis is very popular for its beneficial health properties, such as antimicrobial activity and antioxidant effects. It is one of the most long-serving traditional medicines to mankind due to its interesting chemical diversity and therapeutic properties. The detailed chemical information of propolis samples is very necessary to guarantee its safety and for it to be accepted into health care systems. The phenolic profile of the hydroethanolic extract was determined using HPLC-DAD, and the antioxidant was evaluated using five complementary methods. Triterpenoids were isolated using column chromatography and characterized using H NMR and C NMR. The effects of the extract and the isolated compounds on quorum sensing mediated processes and biofilm formation in bacteria were evaluated. Protocatechic acid (40.76 ± 0.82 µg/g), 4-hydroxybenzoic acid (24.04 ± 0.21 µg/g), vanillic acid (29.90 ± 1.05 µg/g), quercetin (43.53 ± 1.10 µg/g), and luteolin (4.44 ± 0.48 µg/g) were identified and quantified. The extract showed good antioxidant activity in the DPPH, ABTS, CUPRAC, and metal chelating assays, and this antioxidant effect was confirmed by cyclic voltammetry. 27-Hydroxymangiferonic acid (1), Ambolic acid (2), and Mangiferonic acid (3) were isolated from anti-quorum sensing activity at MIC, and it was indicated that the most active sample was the extract with inhibition diameter zone of 18.0 ± 1.0 mm, while compounds , , and had inhibition zones of 12.0 ± 0.5 mm, 9.0 ± 1.0 mm, and 12.3 ± 1.0 mm, respectively. The samples inhibited the PA01 swarming motility at the three tested concentrations (50, 75, and 100 μg/mL) in a dose-dependent manner. The propolis extract was able to inhibit biofilm formation by , , , , and at MIC concentration. Compound proved biofilm inhibition on , , , , and at MIC and MIC/2; compound inhibited the formation of biofilm at MIC on , , , , , and ; and compound inhibited biofilm formation on , , , and and further biofilm inhibition on at MIC/4 and MIC/8. The studied propolis sample showed important amounts of cycloartane-type triterpene acids, and this indicates that there can be significant intra-regional variation probably due to specific flora within the vicinity. The results indicate that propolis and its compounds can reduce virulence factors of pathogenic bacteria.

摘要

蜂胶因其有益的健康特性而非常受欢迎,例如抗菌活性和抗氧化作用。由于其有趣的化学多样性和治疗特性,它是人类使用时间最长的传统药物之一。蜂胶样品的详细化学信息对于保证其安全性和被纳入医疗保健系统非常必要。使用 HPLC-DAD 确定了水醇提取物的酚类谱,并使用五种互补方法评估了抗氧化剂。使用柱层析分离三萜类化合物,并使用 1 H NMR 和 13 C NMR 进行表征。评估了提取物和分离化合物对细菌群体感应介导的过程和生物膜形成的影响。鉴定并定量了原儿茶酸(40.76 ± 0.82 µg/g)、4-羟基苯甲酸(24.04 ± 0.21 µg/g)、香草酸(29.90 ± 1.05 µg/g)、槲皮素(43.53 ± 1.10 µg/g)和木樨草素(4.44 ± 0.48 µg/g)。提取物在 DPPH、ABTS、CUPRAC 和金属螯合测定中表现出良好的抗氧化活性,并且通过循环伏安法证实了这种抗氧化作用。从抗群体感应活性的 MIC 中分离出 27-羟基芒果酸(1)、阿莫比酸(2)和芒果酸(3),结果表明最活跃的样品是提取物,其抑制直径区为 18.0 ± 1.0 mm,而化合物 、 、 和 分别具有 12.0 ± 0.5 mm、9.0 ± 1.0 mm 和 12.3 ± 1.0 mm 的抑制带。样品以剂量依赖性方式抑制三种测试浓度(50、75 和 100 µg/mL)下的 PA01 群集运动。在 MIC 浓度下,蜂胶提取物能够抑制 、 、 、 和 的生物膜形成。化合物 对 、 、 、 和 的 MIC 和 MIC/2 表现出生物膜抑制作用;化合物 抑制 、 、 、 、 和 的生物膜形成,MIC 上;化合物 抑制 、 、 和 的生物膜形成,MIC/4 和 MIC/8 上进一步抑制生物膜形成。研究中的蜂胶样品含有大量环阿尔廷型三萜酸,这表明可能由于附近特定的植物群而存在显著的区域内变异。结果表明,蜂胶及其化合物可以降低致病菌的毒力因子。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a209/9369644/83c49cd10ca1/molecules-27-04872-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a209/9369644/baf12fe86f4f/molecules-27-04872-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a209/9369644/83c49cd10ca1/molecules-27-04872-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a209/9369644/baf12fe86f4f/molecules-27-04872-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a209/9369644/83c49cd10ca1/molecules-27-04872-g002.jpg

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