Artemisia annua L. (Asteraceae) trichome‐specific cDNAs reveal CYP71AV1, a cytochrome P450 with a key role in the biosynthesis of the antimalarial sesquiterpene lactone artemisinin
Open accessAbstract
Artemisinin, a sesquiterpene lactone endoperoxide derived from the plant Artemisia annua, forms the basis of the most important treatments of malaria in use today. In an effort to elucidate the biosynthesis of artemisinin, an expressed sequence tag approach to identifying the relevant biosynthetic genes was undertaken using isolated glandular trichomes as a source of mRNA. A cDNA clone encoding a cytochrome P450 designated CYP71AV1 was characterized by expression in Saccharomyces cerevisiae and shown to catalyze the oxidation of the proposed biosynthetic intermediates amorpha‐4,11‐diene, artemisinic alcohol and artemisinic aldehyde. The identification of the CYP71AV1 gene should allow for the engineering of semi‐synthetic production of artemisinin in appropriate plant or microbial hosts.
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The enzymatic steps involved in production of the non-phytotoxic precursors amorpha-4,11-diene (A-4,11-D) and dihydroartemisinic acid (DHAA) have been elucidated.
“Although the enzymatic steps involved in production of the non-phytotoxic precursors amorpha-4,11-diene (A-4,11-D) and dihydroartemisinic acid (DHAA) have been elucidated (12-15)”
From <i>Artemisia annua</i> mutant impaired in artemisinin synthesis demonstrates importance of nonenzymatic conversion in terpenoid metabolism (2016) · cites this paper as [13]
The Introduction and Results (§3.3; page unavailable) identify amorpha-4,11-diene synthase and show CYP71AV1 catalyzing an oxidation of amorpha-4,11-diene. But the Discussion (§4; page unavailable) says the subsequent route involving dihydroartemisinic acid is less clear, so the paper does not establish that all enzymatic steps to both precursors have been elucidated. It also does not describe the precursors as non-phytotoxic. (LLM, conf=0.88)
Experimental — accuracy not yet measuredThe production of artemisinin occurs in specialized 10-cell biseriate glandular trichomes present on the leaves, stems and inflorescences of Artemisia annua.
“The production of artemisinin occurs in specialized 10-cell biseriate glandular trichomes present on the leaves, stems and inflorescences of Artemisia annua (13).”
From <i>Artemisia annua</i> mutant impaired in artemisinin synthesis demonstrates importance of nonenzymatic conversion in terpenoid metabolism (2016) · cites this paper as [13]
The Introduction describes 10-celled biseriate glandular trichomes, and §3.1 reports evidence of artemisinin-pathway biosynthetic activity in trichomes isolated from flower buds. The copy does not establish that artemisinin production occurs in trichomes on leaves and stems, so the stated distribution is not fully supported. Page numbers were not provided. (LLM, conf=0.86)
Experimental — accuracy not yet measuredCYP71AV1 catalyses the three-step conversion of amorpha-4,11-diene to artemisinic acid.
“We have chosen to target CYP71AV1, which catalyses the three-step conversion of amorpha-4,11-diene to artemisinic acid (13, 26, 27).”
From <i>Artemisia annua</i> mutant impaired in artemisinin synthesis demonstrates importance of nonenzymatic conversion in terpenoid metabolism (2016) · cites this paper as [13]
Compared to WT and heterozygous material, the juvenile leaves of cyp71av1-1 contain significantly elevated levels of amorpha-4,11-diene (A-4,11-D).
“Compared to WT and heterozygous material, the juvenile leaves of cyp71av1-1 contain significantly elevated levels of the first committed metabolite in the artemisinin pathway, amorpha4,11-diene (A-4,11-D; Fig. 1A i), Supplemental T ables 2 and 4), consistent with the reported in vitro activity of CYP71AV1 (13, 26, 27).”
From <i>Artemisia annua</i> mutant impaired in artemisinin synthesis demonstrates importance of nonenzymatic conversion in terpenoid metabolism (2016) · cites this paper as [13]
Amorpha-4,11-diene is hydroxylated to artemisinic alcohol by the cytochrome P450 dependent hydroxylase CYP71AV1.
“In the following step, amorpha-4,11-diene is hydroxylated to yield artemisinic alcohol. This reaction is catalyzed by a cytochrome P450 dependent hydroxylase (CYP71AV1) [12].”
From Relative expression of genes of terpene metabolism in different tissues of Artemisia annuaL (2011) · cites this paper as [12]
These three sequential oxidations of amorpha-4,11-diene (451) produce artemisinic acid (473) via artemisinic alcohol (458) and artemisinic aldehyde (460), with the exocyclic 11,13-double bond remaining intact.
“These three sequential oxidations of amorpha-4,11-diene (451) produce artemisinic acid (473) via artemisinic alcohol (458) and artemisinic aldehyde (460) [196] (note that the exocyclic 11,13-double bond remains intact in this route).”
From The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao) (2010) · cites this paper as [196]
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- Authors
- Teoh, K. H., Polichuk, D. R., Reed, D. W., Nowak, G., & Covello, P. S.
- Affiliations
- Plant Biotechnology Institute (CA)
- Corresponding author
- Covello, Patrick S.
- ORCID
- Reed, Darwin W.
- Venue
- FEBS Letters
- Publisher
- Wiley
- Published
- 2006-01-30
- Volume
- 580
- Issue
- 5
- Pages
- 1411-1416
- ISSN
- 0014-5793 (ISSN-L)
- 1873-3468
- OpenAlex
- W1969962785
- Cited by
- 409
- References
- 25
- Citations by year
- 2026: 8 · 2025: 20 · 2024: 10 · 2023: 19 · 2022: 15 · 2021: 14 · 2020: 20 · 2019: 20 · 2018: 19 · 2017: 18 · 2016: 31 · 2015: 27 · 2014: 21 · 2013: 27 · 2012: 26
- FWCI
- 8.51
- Type
- journal article
- Language
- en
- Open access
- bronze
- doi.org
- Locations
- FEBS Letters (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Plant biochemistry and biosynthesis
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Cancer Research › Sesquiterpenes and Asteraceae Studies
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Plant tissue culture and regeneration
- Keywords
- Artemisia annua, artemisinin biosynthesis, CYP71AV1, cytochrome P450, sesquiterpene lactones, glandular trichomes, expressed sequence tags, endoperoxides, antimalarial compounds
- MeSH terms
- Antimalarials, Cloning, Molecular, Cytochrome P-450 Enzyme System, Epithelial Cells, Oxidation-Reduction, Plant Proteins, Plants, Medicinal, Sesquiterpenes, DNA, Complementary, DNA, Plant, Artemisia annua, Artemisinins
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