Terpenoids from the seeds of Artemisia annua

Brown, Geoffrey D.; Liang, Guang-Yi; Sy, Lai-King

doi:10.1016/s0031-9422(03)00294-2

Cited by 153Sesquiterpenes and Asteraceae StudiesPlant biochemistry and biosynthesisPhytochemistry and Biological Activities

Terpenoids from the seeds of Artemisia annua

Brown, Geoffrey D., Liang, Guang-Yi, Sy, Lai-King·2003·Phytochemistry

DOI 10.1016/s0031-9422(03)00294-2

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Abstract

Fourteen sesquiterpenes, three monoterpenes and one diterpene natural product have been isolated from the seeds of Artemisia annua. The possible biogenesis of some of these natural products are discussed by reference to recently reported experimental results for the autoxidation of dihydroartemisinic acid and other terpenoids from Artemisia annua.

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Ponticaepoxide (121) and annuadiepoxide (122) have been isolated from both leaves and seeds of A. annua.
“which have been isolated from both leaves [67] and seeds [9] of A. annua.”
From The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao) (2010) · cites this paper as [9]
The secondary and tertiary allylic hydroperoxides α- and β-myrcene hydroperoxide have been isolated from A. annua on more than one occasion.
“The secondary and tertiary allylic hydroperoxides, α- and β-myrcene hydroperoxide (265 and 264), have been isolated from A. annua on more than one occasion [9,114]”
From The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao) (2010) · cites this paper as [9]
Reduction of the hydroperoxide in 414 would result in the allylic alcohol group observed in 5α-hydroxy-eudesma-4(15),11-diene (413).
“It has been suggested that reduction of the hydroperoxide in 414 would then result in the allylic alcohol group observed in the natural product 5α-hydroxy-eudesma-4(15),11-diene (413), as shown in Scheme 4 [9].”
From The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao) (2010) · cites this paper as [9]
The isolation of eudesmane allylic hydroperoxide (414) from A. annua is significant, as its structure suggests formation by spontaneous autoxidation of selina-4,11-diene (422).
“The isolation of the eudesmane allylic hydroperoxide (414) from A. annua is significant, as its structure is suggestive of formation by spontaneous autoxidation of the hydrocarbon precursor selina-4,11-diene (422) [9].”
From The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao) (2010) · cites this paper as [9]
The unusual carbon skeleton of 503 might have arisen from an amorphane precursor in which the A ring has been contracted from six to five atoms by carbon-carbon bond migration of C-3 from C-4 to C-5.
“Similarly, the unusual carbon skeleton of 503 might also have arisen from an amorphane precursor, in which the A ring has been contracted from six to five atoms, as a result of carbon-carbon bond migration of C-3 from C-4 to C-5 [9].”
From The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao) (2010) · cites this paper as [9]

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Authors: Brown, G. D., Liang, G.-Y., & Sy, L.-K.
Affiliations: University Grants Committee (HK)
Corresponding author: Brown, Geoffrey D.
ORCID: Brown, Geoffrey D.
Venue: Phytochemistry
Publisher: Elsevier BV
Published: 2003-09
Volume: 64
Issue: 1
Pages: 303-323
ISSN: 0031-9422 (ISSN-L)
DOI: 10.1016/s0031-9422(03)00294-2
OpenAlex: W2014117923
Cited by: 153
References: 65
Citations by year: 2026: 2 · 2025: 7 · 2024: 6 · 2023: 6 · 2022: 5 · 2021: 15 · 2020: 4 · 2019: 9 · 2018: 7 · 2017: 6 · 2016: 12 · 2015: 5 · 2014: 7 · 2013: 10 · 2012: 16
FWCI: 1.36
Type: journal article
Language: en
Open access: closed
Licence: www.elsevier.com/tdm/userlicense/1.0/ (tdm)
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 › Plant biochemistry and biosynthesis
Life Sciences › Agricultural and Biological Sciences › Plant Science › Phytochemistry and Biological Activities
Keywords: Artemisia annua, seeds, sesquiterpenes, monoterpenes, diterpenoids, autoxidation, dihydroartemisinic acid, natural product isolation
MeSH terms: Models, Molecular, Magnetic Resonance Spectroscopy, Oxidation-Reduction, Seeds, Stereoisomerism, Terpenes, Artemisia annua, Artemisinins

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Terpenoids from the seeds of Artemisia annua

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