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

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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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“dihydroartemisinic lactone 234(8), 219(10), 216(2), 190(75), 175(20),151(100), 147(10), 145(7), 137(12), 133(15), 131(7), 125(7), 121(12), 119(40), 109(25), 105(50), 95(20), 93(23), 91(40), 81(45), 69(15), 67(20), 55(55), 53(20), 43(20),”
Influential
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“Several terpenoids including artemisinin and some of its precursors and degradation products, has been found in seeds of A. annua (Brown et al., 2003).”
Background
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“This may explain that, althoughA. annua seeds are trichome-absent, several artemisinin precursors are still found in them (Brown et al. 2003).”
Background
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“Vulgaric acid (1) is a member of bicyclic sesquiterpenes (Brown et al. 2003; Peron et al. 2017; Song et al. 2006; Tori et al. 1995; Yang et al. 2016).”
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A Discovery-Based Metabolomic Approach Using UPLC-Q-TOF-MS/MS Reveals Potential Antimalarial Compounds Present in Artemisia annua L.
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“…genistin ( 6 ) [16], quercetin ( 7 ) [17,18], luteolin ( 8 ) [19,20], isorhamnetin ( 9 ) [21,22], lupinalbin A ( 10 ) [23,24], cedrol ( 11 ) [25 – 28], D-pinitol ( 12 ) [29 – 31], stigmasterol ( 13 ) [32 – 34], stigmasterol glucoside ( 14 ) [32], betulinic acid ( 15 ) [35,36], salicylic acid (…”
Inhibition of nitric oxide production by clerodane diterpenoids from leaves and stems of Croton poomae Esser
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“…dos fl avonóides artemetina (6) (Martinez et al., 1987; Agrawal, 1989), crisosplenetina (7) (Sy; Brown, 1998), casticina (8) (Wang et al., 1989; Brown et al., 2003) e penduletina (9) (Wang et al., 1989) e tilirosídeo (11) (Kaouadji, 1990; Markham, 1993; Silva et al., 2005) foram identifi cadas…”
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“69 % indicates a high degree of Scavenging rate = x 100 (3) A1 − A3”
Background
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“…et al., 1994), 5-heneicosyl-1,3-benzenediol (42) (Feresin et al., 2003), phytene-1,2-diol (43) (Rodríguez and Acosta, 1997), phytol (44) (Brown et al., 2003), 2b-(20,4'-hexadiynoyl)-1, 6-dioxaspiro[4,5]deca-3-ene (45) (Zhu et al., 2010), ichthyothereol acetate (46) (Cascon et al.,…”
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Novel process for selective separation of trace artemisitene from artemisinin by ammonium functional ionic liquids
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“The known compounds were identified as 7-hydroxy--dunnione (2) [5], lapachenole (3) [6], tectoquinone (4) [7], 7methoxytectoquinone (5) [8], 1-hydroxytectoquinone (6) [9], 7hydroxytectoquinone (7) [10], aggregatin C (8) [11], aggregatin D (9) [11], halleridone (10) [12], and cedrol (11) [13].”
Activity-guided isolation and identification of antiherpesvirus and antineuroinflammatory active terpenoids from Artemisia vulgaris L. based on the LC-MS/MS molecular network
Liu, T., Dai, M., Zhu, H., Huang, Y., Chen, J., Li, M., Guo, Y., Huang, C., La, C., Wang, Z., et al. (2023) · Phytochemistry · doi:10.1016/j.phytochem.2023.113863 · Cited by 10
Paralemnolins V and W, New Nardosinane-Type Sesquiterpenoids from a Bornean Soft Coral, Lemnalia sp.
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Two new sesquiterpenes from Artemisia annua L.
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Comparison of terpene components from flowers of Artemisia annua
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“Many secondary metabolites of terpene peroxides were isolated from the plant, such as artemisia ketone, artemisinic alcohol, arteannuin B and myrcene hydroperoxide (Bertea et al., 2005; Brown et al., 2003).”
Background
Variation in Terpene and Linear‐Chain Hydrocarbon Content in Yarrow (Achillea millefolium L.) Germplasm from the Rhaetian Alps, Italy
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Background
Chemical Profile Characterization ofArtemisia annuaL. Essential Oils From South India Through GC-FID and GC-MS Analyses
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Background
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Research Progress on Sesquiterpenes from the Genus Ainsliaea
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Comparison of artemisinin content and antioxidant activity from various organs of Artemisia species
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“Additional key words: A. annua, ABTS, anti-malaria, DPPH, HPLC”

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: Physical Sciences › Chemistry › Organic Chemistry › 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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