Isolation and Identification of Dihydroartemisinic Acid from Artemisia annua and Its Possible Role in the Biosynthesis of Artemisinin
Abstract
Dihydroartemisinic acid (2) was isolated as a natural product from Artemisia annua in a 66% yield, and its structure was confirmed by 1H and 13C NMR spectroscopy. Compound 2 could be chemically converted to artemisinin (4) under conditions that may also be present in the living plant. The results suggest that the conversion of 2 into 4 in the living plant might be a nonenzymatic conversion.
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The final transformations to artemisinin (495) in phase 3 may be non-enzymatic, supported by in vivo and in vitro studies under conditions relevant to the living plant.
“The proposal that the final transformations to artemisinin (495) in phase 3 may be non-enzymatic also receives strong support both from in vivo studies [168,185] and from experiments which have been performed in vitro [167,193,218], under conditions that are relevant to the living plant.”
From The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao) (2010) · cites this paper as [167]
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 [167]
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- Authors
- Wallaart, T. E., van Uden, W., Lubberink, H. G. M., Woerdenbag, H. J., Pras, N., & Quax, W. J.
- Affiliations
- University of Groningen (NL)
- Department of Pharmaceutical Biology, University Centre for Pharmacy, Groningen Institute for Drug Studies, University of Groningen, A. Deusinglaan 1, NL-9713 AV Groningen, The Netherlands
- Venue
- Journal of Natural Products
- Publisher
- American Chemical Society (ACS)
- Published
- 1999-02-04
- Volume
- 62
- Issue
- 3
- Pages
- 430-433
- ISSN
- 0163-3864 (ISSN-L)
- 1520-6025
- OpenAlex
- W2132259321
- Cited by
- 129
- References
- 13
- Citations by year
- 2024: 4 · 2023: 4 · 2022: 1 · 2021: 4 · 2020: 2 · 2019: 5 · 2018: 5 · 2017: 7 · 2016: 3 · 2015: 4 · 2014: 5 · 2013: 9 · 2012: 8
- FWCI
- 1.11
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of Natural Products (publishedVersion)
- PubMed (publishedVersion)
- University of Groningen research database (University of Groningen / Centre for Information Technology) (submittedVersion)
- 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 › Phytochemical compounds biological activities
- Keywords
- dihydroartemisinic acid, artemisinin, Artemisia annua, artemisinin biosynthesis, natural product isolation, structure elucidation, sesquiterpene lactones
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