Crystal structure of artemisinic acid: A possible biogenetic precursor of antimalarial artemisinin from Artemisia annua
Abstract
Artemisinic acid [1], a possible biogenetic precursor of the antimalarial artemisinin [2], was isolated from the hexane extract of Artemisia annua. X-ray crystallography of the dimer of artemisinic acid shows that the cyclization during intermolecular hydrogen bonding occurs by the opposite orientation of the alpha, beta-methylene group in each molecule. Complete spectroscopic data of 1 are also given.
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Artemisinic acid, arteannuin B, and artemisinin are the most abundant representatives of the amorphane/cadinane class of natural products from A. annua.
“Artemisinic acid (473) [105,147,148], arteannuin B (462) [105,147,149] and artemisinin (495) [105,147,150] are the most abundant representatives of this class of natural products”
From The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao) (2010) · cites this paper as [148]
Artemisinic acid, arteannuin B, and artemisinin were amongst the first sesquiterpenes to be reported from A. annua.
“and were amongst the first sesquiterpenes to be reported from A. annua.”
From The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao) (2010) · cites this paper as [148]
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- Authors
- Misra, L. N., Ahmad, A., Thakur, R. S., Lotter, H., & Wagner, H.
- Affiliations
- Central Institute of Medicinal and Aromatic Plants (IN)
- Venue
- Journal of Natural Products
- Publisher
- American Chemical Society (ACS)
- Published
- 1993-02
- Volume
- 56
- Issue
- 2
- Pages
- 215-219
- ISSN
- 0163-3864 (ISSN-L)
- 1520-6025
- OpenAlex
- W1987810203
- Cited by
- 32
- References
- 0
- Citations by year
- 2025: 1 · 2024: 1 · 2022: 1 · 2020: 2 · 2019: 2 · 2018: 1 · 2017: 2 · 2014: 1 · 2013: 3 · 2012: 1
- FWCI
- 0.80
- 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 › Phytochemical compounds biological activities
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Bioactive Natural Diterpenoids Research
- Keywords
- artemisinic acid, artemisinin, Artemisia annua, crystal structure, dimers, biogenetic precursor, antimalarial compounds, intermolecular hydrogen bonding, cyclization, natural product isolation
- MeSH terms
- Antimalarials, Crystallization, Cyclization, Drugs, Chinese Herbal, Hydrogen Bonding, Molecular Conformation, Magnetic Resonance Spectroscopy, Sesquiterpenes, X-Ray Diffraction, Artemisinins
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