Deoxyarteannuin B, dihydro-deoxyarteannuin B and trans-5-hydroxy-2-isopropenyl-5-methylhex-3-en-1-ol from Artemisia anuua
Abstract
The amorphane sesquiterpenes, deoxyarteannuin B and dihydro-deoxyarteannuin B, were isolated from Artemisia annua and their structures mainly determined by two-dimensional NMR spectoscopic analyses. The irregular monoterpene, trans-5-hydroxy-2-isopropenyl-5-methylhex-3-en-1-ol, was also characterized in the same way, and its structure was confirmed by synthesis from lavandulol. All of these natural products are suggested to be formed by autoxidation reactions. Full assignments of the 1H and 13C resonances for the known natural products epi-deoxyarteannuin B and isoannulide, determined by the same methodology, are also reported.
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The lavandulane tertiary allylic alcohol 279 and its secondary allylic alcohol analogue 280 are proposed to be derived from lavandulol by spontaneous autoxidation reactions yielding allylic hydroperoxide intermediates.
“Both the lavandulane tertiary allylic alcohol 279 and its secondary allylic alcohol analogue 280 have been proposed to be derived from the precursor, lavandulol, by spontaneous autoxidation reactions which yield allylic hydroperoxide intermediates as shown in Scheme 3 [129].”
From The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao) (2010) · cites this paper as [129]
A biomimetic synthesis supported the derivation of 279 and 280 from lavandulol by spontaneous autoxidation: photooxygenation of racemic lavandulol yielded both hydroperoxide intermediates expected from reaction of singlet oxygen with the tri-substituted double bond in lavandulol.
“This suggestion was supported by a biomimetic synthesis, in which photooxygenation of racemic lavandulol yielded both of the hydroperoxide intermediates expected from the reaction of singlet oxygen with the tri-substituted double bond in this precursor.”
From The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao) (2010) · cites this paper as [129]
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- Authors
- Sy, L.-K., & Brown, G. D.
- Affiliations
- University of Hong Kong (HK)
- Corresponding author
- Brown, Geoffrey D
- ORCID
- Brown, Geoffrey D
- Venue
- Phytochemistry
- Publisher
- Elsevier BV
- Published
- 2001-12
- Volume
- 58
- Issue
- 8
- Pages
- 1159-1166
- ISSN
- 0031-9422 (ISSN-L)
- OpenAlex
- W2095312356
- Cited by
- 36
- References
- 18
- Citations by year
- 2026: 2 · 2025: 1 · 2024: 2 · 2023: 2 · 2022: 1 · 2021: 1 · 2020: 1 · 2018: 3 · 2017: 2 · 2016: 2 · 2015: 1 · 2014: 1 · 2012: 1
- FWCI
- 0.76
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Phytochemistry (publishedVersion)
- PubMed (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
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Bioactive Natural Diterpenoids Research
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Phytochemical compounds biological activities
- Keywords
- Artemisia annua, lavandulol, autoxidation, natural product isolation, structure elucidation
- MeSH terms
- Sesquiterpenes, Terpenes, Artemisia, Artemisinins, Monoterpenes
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