The mechanism of the spontaneous autoxidation of dihydroartemisinic acid
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The pattern of transformations of dihydroartemisinic acid (480) observed in vivo very closely paralleled the spontaneous autoxidation chemistry for dihydroartemisinic acid previously demonstrated in vitro.
“The pattern of transformations of dihydroartemisinic acid (480) which was observed in vivo very closely paralleled the spontaneous autoxidation chemistry for dihydroartemisinic acid which had previously been demonstrated in vitro [193,218].”
From The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao) (2010) · cites this paper as [193]
The related seco-cadinane natural product 504 has been reported from the in vitro autoxidation of dihydroartemisinic acid in organic solution.
“(the related seco-cadinane natural product 504 has also been reported from the in vitro autoxidation of dihydroartemisinic acid in organic solution) [193].”
From The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao) (2010) · cites this paper as [193]
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 [193]
The step iii reaction most probably proceeds via an ene-type mechanism similar to the conversion of 480 to 481, apparently without requirement for light, with 3O2 rather than 1O2 as the active species.
“This reaction most probably proceeds via an “ene-type” mechanism similar to that for the conversion of 480 to 481, although apparently without the requirement for light (i.e. 3O2 rather than 1O2 is perhaps the active species) [193,236,304,305].”
From The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao) (2010) · cites this paper as [193]
The evidence for steps ii)-iv) proposed in Scheme 12 comes solely from in vitro studies conducted with the tertiary allylic hydroperoxide 481.
“The evidence for steps ii)-iv) which are proposed in Scheme 12 comes solely from in vitro studies, conducted with the tertiary allylic hydroperoxide 481 [171,236,237,239,254], which can be obtained in good yield from photosensitized oxygenation of 480 [193,218].”
From The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao) (2010) · cites this paper as [193]
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References 40 · Cited by 129
- Authors
- Sy, L.-K., & Brown, G. D.
- Affiliations
- University Grants Committee (HK)
- Corresponding author
- Brown, Geoffrey D
- ORCID
- Brown, Geoffrey D
- Venue
- Tetrahedron
- Publisher
- Elsevier BV
- Published
- 2002-01
- Volume
- 58
- Issue
- 5
- Pages
- 897-908
- ISSN
- 0040-4020 (ISSN-L)
- OpenAlex
- W2080053579
- Cited by
- 129
- References
- 40
- Citations by year
- 2026: 2 · 2025: 6 · 2024: 6 · 2023: 5 · 2022: 2 · 2021: 6 · 2020: 6 · 2019: 3 · 2018: 6 · 2017: 7 · 2016: 5 · 2015: 6 · 2014: 10 · 2013: 10 · 2012: 7
- FWCI
- 1.18
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Tetrahedron (publishedVersion)
- The HKU Scholars Hub (University of Hong Kong) (submittedVersion)
- Funders
- University of Hong Kong
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Cancer Research › Sesquiterpenes and Asteraceae Studies
- Physical Sciences › Chemistry › Organic Chemistry › Oxidative Organic Chemistry Reactions
- Physical Sciences › Chemistry › Organic Chemistry › Chemical Reaction Mechanisms
- Keywords
- dihydroartemisinic acid, artemisinin, autoxidation, oxidation mechanism, Artemisia annua, allylic hydroperoxides, 1,2,4-trioxanes, natural product transformation
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