https://scholars.lib.ntu.edu.tw/handle/123456789/629782
Title: | Luteolin Phosphate Derivatives Generated by Cultivating Bacillus subtilis var. Natto BCRC 80517 with Luteolin | Authors: | Tsai, Hsin-Ya Chen, Ming-Yu Hsu, Chen Kuan, Kai-Yuan Chang, Chi-Fon Wang, Che-Wei Hsu, Chao-Ping NAN-WEI SU |
Keywords: | Bacillus subtilis; bioconversion; biophosphorylation; luteolin; luteolin phosphates; phosphate transesterification | Issue Date: | 20-Jul-2022 | Publisher: | AMER CHEMICAL SOC | Journal Volume: | 70 | Journal Issue: | 28 | Source: | Journal of agricultural and food chemistry | Abstract: | Luteolin (LUT), a plant-derived flavone, exhibits various bioactivities; however, the poor aqueous solubility hampers its applications. Here, we revealed bioconversion of LUT by Bacillus subtilis BCRC 80517, yielding three water-soluble phosphate conjugates. These derivatives were identified as luteolin 4'-O-phosphate (L4'P), luteolin 3'-O-phosphate (L3'P), and luteolin 7-O-phosphate (L7P) by LC-ESI-MS/MS and NMR. Besides, we found that Bacillus subtilis BCRC 80517 was able to convert different levels of LUT but showed a limited conversion rate. By observing bacterial morphology with transmission electron microscopy and confocal fluorescence microscopy, we found that LUT disrupted the bacterial membrane integrity, which explained the incomplete conversion. Additionally, we revealed a spontaneous intramolecular transesterification of L4'P to L3'P, the thermodynamically more stable form, under acidic conditions and proposed the possible mechanism involving a cyclic phosphate as the intermediate. This study provides insight into development of a potent structural modification strategy to enhance the solubility of LUT through biophosphorylation. |
URI: | https://scholars.lib.ntu.edu.tw/handle/123456789/629782 | ISSN: | 0021-8561 | DOI: | 10.1021/acs.jafc.2c03524 |
Appears in Collections: | 農業化學系 |
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