Isolation and Identification of Dihydroartemisinic Acid Hydroperoxide from Artemisia annua: A Novel Biosynthetic Precursor of Artemisinin
Abstract
Dihydroartemisinic acid hydroperoxide (2) was isolated for the first time as a natural product from the plant Artemisia annua in a 29% yield. Its structure was identified by (1)H and (13)C NMR spectroscopy. Compound 2 is known as an intermediate of the photochemical oxidation of dihydroartemisinic acid (1) leading to artemisinin (3). The presence of 1 and 2 in the plant and the conditions under which 1 can be converted into 2, which can very easily oxidize to 3, provide evidence for a nonenzymatic, photochemical conversion of 1 into 3, in vivo, in the plant.
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Compound 481 has been described independently as a natural product from A. annua.
“Compound 481 has also been described independently as a natural product from A. annua [167,170]”
From The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao) (2010) · cites this paper as [170]
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References 9 · Cited by 101
- Authors
- Wallaart, T. E., Pras, N., & Quax, W. J.
- Affiliations
- University of Groningen (NL)
- Corresponding author
- Pras, Niesko
- ORCID
- Quax, Wim J.
- Venue
- Journal of Natural Products
- Publisher
- American Chemical Society (ACS)
- Published
- 1999-07-31
- Volume
- 62
- Issue
- 8
- Pages
- 1160-1162
- ISSN
- 0163-3864 (ISSN-L)
- 1520-6025
- OpenAlex
- W2075920651
- Cited by
- 101
- References
- 9
- Citations by year
- 2026: 2 · 2025: 3 · 2024: 2 · 2023: 3 · 2022: 5 · 2021: 1 · 2020: 1 · 2019: 3 · 2018: 6 · 2017: 3 · 2016: 1 · 2015: 6 · 2014: 2 · 2013: 8 · 2012: 5
- FWCI
- 0.74
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of Natural Products (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Cancer Research › Sesquiterpenes and Asteraceae Studies
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Plant biochemistry and biosynthesis
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Bioactive Natural Diterpenoids Research
- Keywords
- dihydroartemisinic acid, artemisinin, Artemisia annua, photooxidation, non-enzymatic oxidation, biosynthetic precursors, natural product isolation, structure elucidation
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