The role of the 12-carboxylic acid group in the spontaneous autoxidation of dihydroartemisinic acid
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The final steps in the conversion of DHAA to artemisinin are considered to be non-enzymatic and may be extracellular.
“the final steps in the conversion of DHAA to artemisinin are considered to be non-enzymatic and may be extracellular (17, 18).”
From <i>Artemisia annua</i> mutant impaired in artemisinin synthesis demonstrates importance of nonenzymatic conversion in terpenoid metabolism (2016) · cites this paper as [18]
In vivo and in vitro formation of low abundance by-products derived from other intermediates of artemisinin synthesis have previously been reported.
“In vivo and in vitro formation of low abundance by-products derived from other intermediates of artemisinin synthesis have previously been reported (12, 17, 18).”
From <i>Artemisia annua</i> mutant impaired in artemisinin synthesis demonstrates importance of nonenzymatic conversion in terpenoid metabolism (2016) · cites this paper as [18]
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 [218]
The formyl group in compound 505 is probably derived from oxidative rearrangements, deriving from the 5-position of an appropriate bicyclic precursor.
“Similarly, the formyl group in 1-oxo-2β-[3-butanone]-3α-methyl-6β-[2-propanol formyl ester]-cyclohexane (505) [218] is probably also derived from oxidative rearrangements, this time deriving from the 5-position of an appropriate bicyclic precursor”
From The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao) (2010) · cites this paper as [218]
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 [218]
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 [218]
Understanding of how the spontaneous autoxidation of natural products such as 480 occurs in the absence of a photosensitizer or other additional chemical reagents, leading to highly oxidized products such as 495, is still incomplete.
“It should be noted that our understanding of how the spontaneous autoxidation of natural products such as 480 occurs in the absence of a photosensitizer [388] (or, indeed, any other additional chemical reagents [218]), leading to highly oxidized products such as 495, is still incomplete.”
From The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao) (2010) · cites this paper as [218]
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- 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
- 909-923
- ISSN
- 0040-4020 (ISSN-L)
- OpenAlex
- W1969943057
- Cited by
- 36
- References
- 21
- Citations by year
- 2025: 1 · 2024: 2 · 2023: 2 · 2021: 2 · 2020: 1 · 2019: 1 · 2018: 2 · 2017: 3 · 2016: 1 · 2015: 1 · 2013: 3 · 2012: 3
- FWCI
- 1.97
- 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
- Physical Sciences › Chemistry › Organic Chemistry › Oxidative Organic Chemistry Reactions
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Cancer Research › Sesquiterpenes and Asteraceae Studies
- Physical Sciences › Chemistry › Organic Chemistry › Chemical Reaction Mechanisms
- Keywords
- dihydroartemisinic acid, artemisinin, allylic hydroperoxides, 1,2,4-trioxanes, molecular oxygen, cyclization, artemisinin biosynthesis
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