Journal
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
Volume 69, Issue 47, Pages 14231-14240Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.jafc.1c06094
Keywords
prenyltransferase; 6-prenylnaringenin; promiscuous kinase; isopentenyl phosphate kinase
Funding
- National Natural Science Foundation of China [21978135]
- Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD)
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The study showed that prenylation can provide flavonoids with specific activities and pharmacological properties, and successfully synthesized 6-prenylnaringenin in Escherichia coli with the highest yield.
Prenyl groups increase the lipophilicity of flavonoids, endowing them with a special activity, selectivity, and pharmacological properties by prenylation. Herein, a novel prenyltransferase (ShFPT) gene from Streptomyces sp. NT11 was expressed in Escherichia coli, and its biochemical characteristics were determined. ShFPT exhibited high selectivity to prenylate naringenin at C-6 to generate 6-prenylnaringenin. The optimal activity was observed at pH 6.0 and 55 degrees C. The K-cat and K-m for naringenin were 0.0095 s(-1) and 0.20 mM, respectively. Several promiscuous kinase and isopentenyl phosphate kinase genes were screened to develop the most efficient dimethylallyl diphosphate (DMAPP) synthesis pathway for 6-prenylnaringenin synthesis in E. coli. The 6-prenylnaringenin production was improved by changing the induction strategies and optimizing the bioconversion conditions. Finally, 6-prenylnaringenin production reached the highest yield of 69.9 mg/L with average productivity of 4.0 mg/L/h after 16 h incubation, which is the highest yield for any prenylated flavonoid reported to date in E. coli. Therefore, this study provides an efficient method for 6-prenylnaringenin production and reveals the DMAPP synthesis pathway.
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