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Article|17 Aug 2023|OPEN
The parallel biosynthesis routes of hyperoside from naringenin in Hypericum monogynum
Yingying Wang1 , Zhirong Cui1 , Qianqian Li1 , Shuai Zhang1 , Yongyi Li1 , Xueyan Li1 , Lingyi Kong1 , and Jun Luo,1 ,
1Jiangsu Key Laboratory of Bioactive Natural Product Research and State Key Laboratory of Natural Medicines, Department of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing 210009, China
*Corresponding author. E-mail:,

Horticulture Research 10,
Article number: uhad166 (2023)
Views: 128

Received: 24 Feb 2023
Accepted: 09 Aug 2023
Published online: 17 Aug 2023


Hyperoside is a bioactive flavonoid galactoside in both medicinal and edible plants. It plays an important physiological role in the growth of flower buds. However, the hyperoside biosynthesis pathway has not been systematically elucidated in plants, including its original source, Hypericaceae. Our group found abundant hyperoside in the flower buds of Hypericum monogynum, and we sequenced its transcriptome to study the biosynthetic mechanism of hyperoside. After gene screening and functional verification, four kinds of key enzymes were identified. Specifically, HmF3Hs (flavanone 3-hydroxylases) and HmFLSs (flavonol synthases) could catalyze flavanones into dihydroflavonols, as well as catalyzing dihydroflavonols into flavonols. HmFLSs could also convert flavanones into flavonols and flavones with varying efficiencies. HmF3′H (flavonoid 3′-hydroxylase) was found to act broadly on 4′-hydroxyl flavonoids to produce 3′,4′-diydroxylated flavanones, dihydroflavonols, flavonols, and flavones. HmGAT (flavonoid 3-O-galactosyltransferase) would transform flavonols into the corresponding 3-O-galactosides, including hyperoside. The parallel hyperoside biosynthesis routes were thus depicted, one of which was successfully reconstructed in Escherichia coli BL21(DE3) by feeding naringenin, resulting in a hyperoside yield of 25 mg/l. Overall, this research not only helped us understand the interior catalytic mechanism of hyperoside in H. monogynum concerning flower development and bioactivity, but also provided valuable insights into these enzyme families.