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Licorice β-amyrin 11-oxidase, a cytochrome P450 with a key role in the biosynthesis of the triterpene sweetener glycyrrhizin
Open accessAbstract
Glycyrrhizin, a major bioactive compound derived from the underground parts of Glycyrrhiza (licorice) plants, is a triterpene saponin that possesses a wide range of pharmacological properties and is used worldwide as a natural sweetener. Because of its economic value, the biosynthesis of glycyrrhizin has received considerable attention. Glycyrrhizin is most likely derived from the triterpene β-amyrin, an initial product of the cyclization of 2,3-oxidosqualene. The subsequent steps in glycyrrhizin biosynthesis are believed to involve a series of oxidative reactions at the C-11 and C-30 positions, followed by glycosyl transfers to the C-3 hydroxyl group; however, no genes encoding relevant oxidases or glycosyltransferases have been identified. Here we report the successful identification of CYP88D6 , a cytochrome P450 monooxygenase (P450) gene, as a glycyrrhizin-biosynthetic gene, by transcript profiling-based selection from a collection of licorice expressed sequence tags (ESTs). CYP88D6 was characterized by in vitro enzymatic activity assays and shown to catalyze the sequential two-step oxidation of β-amyrin at C-11 to produce 11-oxo-β-amyrin, a possible biosynthetic intermediate between β-amyrin and glycyrrhizin. CYP88D6 coexpressed with β-amyrin synthase in yeast also catalyzed in vivo oxidation of β-amyrin to 11-oxo-β-amyrin. CYP88D6 expression was detected in the roots and stolons by RT-PCR; however, no amplification was observed in the leaves or stems, which is consistent with the accumulation pattern of glycyrrhizin in planta . These results suggest a role for CYP88D6 as a β-amyrin 11-oxidase in the glycyrrhizin pathway.
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Thimmappa, R., Geisler, K., Louveau, T., O'Maille, P., & Osbourn, A. (2014) · Annual Review of Plant Biology · doi:10.1146/annurev-arplant-050312-120229 · Cited by 803
Plant terpenes: defense responses, phylogenetic analysis, regulation and clinical applications
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The cytochrome P450 superfamily: Key players in plant development and defense
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Self-citationCYP716A Subfamily Members are Multifunctional Oxidases in Triterpenoid Biosynthesis
Fukushima, E. O., Seki, H., Ohyama, K., Ono, E., Umemoto, N., Mizutani, M., Saito, K., & Muranaka, T. (2011) · Plant and Cell Physiology · doi:10.1093/pcp/pcr146 · Cited by 309
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Metadata
- Authors
- Seki, H., Ohyama, K., Sawai, S., Mizutani, M., Ohnishi, T., Sudo, H., Akashi, T., Aoki, T., Saito, K., & Muranaka, T.
- Venue
- Proceedings of the National Academy of Sciences
- Published
- 2008-09-16
- Volume
- 105
- Issue
- 37
- Pages
- 14204-14209
- ISSN
- 0027-8424 (ISSN-L)
- 1091-6490
- OpenAlex
- W2070429529
- Cited by
- 388
- References
- 31
- FWCI
- 6.08
- Type
- journal article
- Language
- en
- Open access
- green
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- Seki, H., Ohyama, K., Sawai, S., Mizutani, M., Ohnishi, T., Sudo, H., Akashi, T., Aoki, T., Saito, K., & Muranaka, T. (2008). Licorice β-amyrin 11-oxidase, a cytochrome P450 with a key role in the biosynthesis of the triterpene sweetener glycyrrhizin. Proceedings of the National Academy of Sciences. https://doi.org/10.1073/pnas.0803876105
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