Hydroxylation decoration patterns of flavonoids in horticultural crops: chemistry, bioactivity and biosynthesis
- PMID: 35048127
- PMCID: PMC8945325
- DOI: 10.1093/hr/uhab068
Hydroxylation decoration patterns of flavonoids in horticultural crops: chemistry, bioactivity and biosynthesis
Abstract
Flavonoids are the most widespread polyphenolic compounds and are important dietary constituents present in horticultural crops such as fruits, vegetables, and tea. Natural flavonoids are responsible for important quality traits, such as food colors and beneficial dietary antioxidants and numerous investigations have shown that intake of flavonoids can reduce the incidence of various non-communicable diseases (NCDs). Analysis of the thousands of flavonoids reported so far has shown that different hydroxylation modifications affect their chemical properties and nutritional values. These diverse flavonoids can be classified based on different hydroxylation patterns in the B, C, A rings and multiple structure-activity analyses have shown that hydroxylation decoration at specific positions markedly enhances their bioactivities. This review focuses on current knowledge concerning hydroxylation of flavonoids catalyzed by several different types of hydroxylase enzymes. Flavonoid 3'-hydroxylase (F3'H) and flavonoid 3'5'-hydroxylase (F3'5'H) are important enzymes for the hydroxylation of the B ring of flavonoids. Flavanone 3-hydroxylase (F3H) is key for the hydroxylation of the C ring, while flavone 6-hydroxylase (F6H) and flavone 8-hydroxylase (F8H) are key enzymes for hydroxylation of the A ring. These key hydroxylases in the flavonoid biosynthesis pathway are promising targets for the future bioengineering of plants and mass production of flavonoids with designated hydroxylation patterns of high nutritional importance. In addition, hydroxylation in key places on the ring may help render flavonoids ready for degradation, the catabolic turnover of which may open the door for new lines of inquiry.
© The Author(s) 2022. Published by Oxford University Press. All rights reserved.
Figures
![Figure 1](https://www.ncbi.nlm.nih.gov/pmc/articles/instance/8945325/bin/uhab068f1.gif)
![Figure 2](https://www.ncbi.nlm.nih.gov/pmc/articles/instance/8945325/bin/uhab068f2.gif)
![Figure 3](https://www.ncbi.nlm.nih.gov/pmc/articles/instance/8945325/bin/uhab068f3.gif)
Similar articles
-
Functional analysis of flavonoid 3'-hydroxylase and flavonoid 3',5'-hydroxylases from tea plant (Camellia sinensis), involved in the B-ring hydroxylation of flavonoids.Gene. 2019 Oct 30;717:144046. doi: 10.1016/j.gene.2019.144046. Epub 2019 Aug 18. Gene. 2019. PMID: 31434006
-
The B-ring hydroxylation pattern of anthocyanins can be determined through activity of the flavonoid 3'-hydroxylase on leucoanthocyanidins.Planta. 2014 Nov;240(5):1003-10. doi: 10.1007/s00425-014-2166-3. Epub 2014 Oct 2. Planta. 2014. PMID: 25269395
-
Flower colour and cytochromes P450.Philos Trans R Soc Lond B Biol Sci. 2013 Jan 6;368(1612):20120432. doi: 10.1098/rstb.2012.0432. Print 2013 Feb 19. Philos Trans R Soc Lond B Biol Sci. 2013. PMID: 23297355 Free PMC article. Review.
-
Identification of the molecular basis for the functional difference between flavonoid 3'-hydroxylase and flavonoid 3',5'-hydroxylase.FEBS Lett. 2007 Jul 24;581(18):3429-34. doi: 10.1016/j.febslet.2007.06.045. Epub 2007 Jun 27. FEBS Lett. 2007. PMID: 17612530
-
The antitumor activities of flavonoids.In Vivo. 2005 Sep-Oct;19(5):895-909. In Vivo. 2005. PMID: 16097445 Review.
Cited by
-
Functional Characterization of F3H Gene and Optimization of Dihydrokaempferol Biosynthesis in Saccharomyces cerevisiae.Molecules. 2024 May 8;29(10):2196. doi: 10.3390/molecules29102196. Molecules. 2024. PMID: 38792058 Free PMC article.
-
Insights into the Superrosids phylogeny and flavonoid synthesis from the telomere-to-telomere gap-free genome assembly of Penthorum chinense Pursh.Hortic Res. 2023 Dec 19;11(2):uhad274. doi: 10.1093/hr/uhad274. eCollection 2024 Feb. Hortic Res. 2023. PMID: 38344651 Free PMC article.
-
Multiple Physiological and Biochemical Functions of Ascorbic Acid in Plant Growth, Development, and Abiotic Stress Response.Int J Mol Sci. 2024 Feb 2;25(3):1832. doi: 10.3390/ijms25031832. Int J Mol Sci. 2024. PMID: 38339111 Free PMC article. Review.
-
4-Hydroxyphenylacetate 3-Hydroxylase (4HPA3H): A Vigorous Monooxygenase for Versatile O-Hydroxylation Applications in the Biosynthesis of Phenolic Derivatives.Int J Mol Sci. 2024 Jan 19;25(2):1222. doi: 10.3390/ijms25021222. Int J Mol Sci. 2024. PMID: 38279222 Free PMC article. Review.
-
Enrichment of Water Bodies with Phenolic Compounds Released from Betula and Pinus Pollen in Surface Water.Plants (Basel). 2023 Dec 28;13(1):99. doi: 10.3390/plants13010099. Plants (Basel). 2023. PMID: 38202407 Free PMC article.
References
-
- Crozier A, Jaganath IB, Clifford MN. Dietary phenolics: chemistry, bioavailability and effects on health. Nat Prod Rep. 2009;26:1001–43. - PubMed
-
- Saijo Y, Loo EP. Plant immunity in signal integration between biotic and abiotic stress responses. New Phytol. 2020;225:87–104. - PubMed
-
- Sun CD, Liua Y, Zhan Let al. . Anti-diabetic effects of natural antioxidants from fruits. Trends Food Sci Technol. 2021;117:3–14.
-
- Alseekh S, Perez de Souza L, Benina Met al. . The style and substance of plant flavonoid decoration; towards defining both structure and function. Phytochemistry. 2020;174:112347. - PubMed
LinkOut - more resources
Full Text Sources
Miscellaneous