Prenylation of flavonoids by DMATS1 and their anti-inflammatory activities

IF 3.5 2区农林科学 Q1 AGRICULTURE, MULTIDISCIPLINARY

Journal of the Science of Food and Agriculture Pub Date : 2025-02-26 DOI:10.1002/jsfa.14198

Zhengjiao Gao, Dingtao Tang, Bingfeng He, Jiajie Quan, Zhengke Zhang, Yueming Jiang, Bao Yang, Jiali Yang

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引用次数: 0

Abstract

BACKGROUND

Prenylated flavonoids are widely distributed in plants, including fruits and vegetables in the Moraceae and Fabaceae families. These chemicals are potential functional food ingredients owing to their attractive biological activities. However, natural prenylated flavonoids are rare, which limits their application.

RESULTS

Here, we reported the prenylation of apigenin and genistein catalyzed by DMATS1, a dimethylallyl-l-tryptophan synthase from Fusarium fujikuroi. High-performance liquid chromatography–tandem mass spectrometry and nuclear magnetic resonance identified their structure as 6-C-prenylapigenin (6-PA) and 6-C-prenylgenistein (6-PG), respectively. Cell-based assay suggested that both 6-PA and 6-PG induced the proliferation of THP-1 cells under low concentrations and were safe in doses less than 50 μmol L⁻¹. 6-PA and 6-PG exhibited significant anti-inflammatory activity in lipopolysaccharide-stimulated THP-1 cells, and inhibited the production of nitric oxide as well as downregulating the transcriptional levels of pro-inflammatory cytokines, including tumor necrosis factor-α, interleukin-8, and interleukin-1β.

CONCLUSION

The findings suggested that DMATS1 could catalyze the 6-C prenylation of apigenin and genistein, and the generated 6-PA and 6-PG exhibited anti-inflammatory activity, aiding in the recognition of 6-PA and 6-PG as nutraceuticals. © 2025 Society of Chemical Industry.

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DMATS1对类黄酮的烯酰化及其抗炎活性。

背景：烯酰化黄酮类化合物广泛分布于植物中，包括桑科和豆科的水果和蔬菜。这些化学物质因其诱人的生物活性而成为潜在的功能性食品成分。然而，天然的烯丙基类黄酮很少见，这限制了它们的应用。结果：本文报道了一种来自藤黑镰刀菌的二甲基烯丙基色氨酸合成酶DMATS1催化芹菜素和染料木素的戊酰化。高效液相色谱-串联质谱和核磁共振鉴定其结构分别为6-C-prenylapigenin （6-PA）和6-C-prenylgenistein （6-PG）。基于细胞的实验表明，6-PA和6-PG在低浓度下均能诱导THP-1细胞增殖，且剂量小于50 μmol L-1是安全的。6-PA和6-PG在脂多糖刺激的THP-1细胞中表现出显著的抗炎活性，抑制一氧化氮的产生，下调促炎细胞因子（包括肿瘤坏死因子-α、白细胞介素-8和白细胞介素-1β）的转录水平。结论：DMATS1可催化芹菜素和染料木素的6-C烯酰化，生成的6-PA和6-PG具有抗炎活性，有助于6-PA和6-PG作为保健品的识别。©2025化学工业协会。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Journal of the Science of Food and Agriculture 工程技术-农业综合

CiteScore

8.10

自引率

4.90%

发文量

634

审稿时长

3.1 months

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