Bioconversion of arteannuin B to artemisinin
Abstract
Arteannuin B, which co-occurs with artemisinin, the potent antimalarial principle of the Chinese medicinal herb Artemisia annua (Asteraceae), has been converted to the latter using crude and semi-purified cell-free extracts of the leaf homogenates of the plant. Detection procedures to quantitate this bioconversion, including one that is novel which uses gcms, are detailed.
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A large number of other cadinane and amorphane sesquiterpenes have been suggested as late-stage intermediates at or around the juncture between phases 2 and 3 of artemisinin biosynthesis.
“A large number of other cadinane and amorphane sesquiterpenes, including: arteannuin B (462) [248,285]; epi-deoxyarteannuin B (478) [286]; dihydroarteannuin B (479) [249]; dihydro-epi-deoxyarteannuin B (485) [286]; the seco-cadinane (494) [217]; and artemisitene (497) [211,248,284] have also been suggested as late-stage intermediates at or around this point in the biosynthesis”
From The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao) (2010) · cites this paper as [248]
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“annua (Nair and Basile 1993; Martinez and Staba 1988).”
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“…have been conducted to elucidate the biochemical pathway of artemisinin synthesis and its biological regulation with an aim to improve artemisinin contents of the plant (Nair and Basile 1993; Bharel et al. 1998; Covello 2008; Bouwmeester et al. 1999; Graham et al. 2010; Arsenault et al. 2010a, b).”
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“At the same time, Nair and Basile (1993) have realized the in vitro bioconversion of arteannuin B to artemisinin by incubation with a leaf extract of A. annua L., suggesting that arteannuin B may be an intermediate in the bioconversion of artemisinin from artemisinic acid.”
BackgroundState of the art of the production of the antimalarial compound artemisinin in plants
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“annua leaves converted arteannuin B into artemisinin [56].”
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“For example, bioconversion of arteannuin b to artemisinin and conversion of artemisinic acid to arteannuin b and artemisinin were observed from radioactive labelling (Akhila et al. 1987; Nair and Basile 1993; Sangwan et al. 1993).”
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“Chemical synthesis has demonstrated that arteannuin B is another appropriate precursor molecule for the semi-synthesis of artemisinin (Nowak and Lansbury, 1998), and for biotransformation to artemisinin (Akhila et al., 1987; Nair and Basile, 1993; Dhingra and Lakshmi Narasu, 2001).”
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- Authors
- Nair, M. S. R., & Basile, D. V.
- Affiliations
- Lehman College (US)
- Venue
- Journal of Natural Products
- Publisher
- American Chemical Society (ACS)
- Published
- 1993-09
- Volume
- 56
- Issue
- 9
- Pages
- 1559-1566
- ISSN
- 0163-3864 (ISSN-L)
- 1520-6025
- OpenAlex
- W1997110108
- Cited by
- 62
- References
- 0
- Citations by year
- 2025: 1 · 2024: 1 · 2023: 1 · 2022: 1 · 2021: 1 · 2020: 4 · 2019: 2 · 2018: 3 · 2017: 1 · 2016: 2 · 2015: 2 · 2014: 1 · 2013: 2 · 2012: 2
- FWCI
- 0.26
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of Natural Products (publishedVersion)
- PubMed (publishedVersion)
- Funders
- National Institutes of Health
- U.S. Public Health Service (5RO1-A128975)
- National Institute of Allergy and Infectious Diseases
- Walter Reed Army Institute of Research
- 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
- arteannuin B, artemisinin, biotransformation, Artemisia annua, cell-free extracts, antimalarial compounds, natural product transformation
- MeSH terms
- Cell-Free System, Cells, Cultured, Chromatography, Thin Layer, Medicine, Chinese Traditional, Plants, Plants, Medicinal, Sesquiterpenes, Spectrophotometry, Ultraviolet, Ultrafiltration, Artemisinins
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