The DOI matches its Crossref record; 64 of the 65 references it cites were found in a registry or an index.
Terpenoids from the seeds of Artemisia annua
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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In the citing paper
“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]
In the citing paper
“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]
In the citing paper
“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]
In the citing paper
“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]
In the citing paper
“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]
In the citing paper
“Both phytol (550) itself and an authentic sample of phytene-1,2-diol (552) were subsequently obtained as natural products from the seeds of A. annua [9].”
From The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao) (2010) · cites this paper as [9]
In the citing paper
“The structure of the diterpene phytene-1-ol-2-hydroperoxide (553) [9,260] was wrongly assigned as phytene-1,2-diol (552), when it was first described as a natural product from A. annua [261].”
From The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao) (2010) · cites this paper as [9]
In the citing paper
“The structure of 3α,15-dihydroxycedrane (534) from A. annua has been rigorously determined both by 2D-NMR and by synthesis from (+)-β-cedrene [9].”
From The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao) (2010) · cites this paper as [9]
Citations
Cites
Connolly, J. D., & Hill, R. A. (1991) · Springer eBooks · doi:10.1007/978-1-4899-4513-6 · Cited by 633
Mercke, P., Bengtsson, M., Bouwmeester, H. J., Posthumus, M. A., & Brodelius, P. E. (2000) · Archives of Biochemistry and Biophysics · doi:10.1006/abbi.2000.1962 · Cited by 283
Bülow, N., & König, W. Α. (2000) · Phytochemistry · doi:10.1016/s0031-9422(00)00266-1 · Cited by 260
Antimalarial activity of Artemisia annua flavonoids from whole plants and cell cultures
Liu, K. C.-S., Yang, S., ROBERTS, M. F., Elford, B. C., & Phillipson, J. D. (1992) · Plant Cell Reports · doi:10.1007/bf00236389 · Cited by 189
Cytotoxic Terpenoids and Flavonoids from Artemisia annua
Zheng, G.-Q. (1994) · Planta Medica · doi:10.1055/s-2006-959408 · Cited by 139
The mechanism of the spontaneous autoxidation of dihydroartemisinic acid
Sy, L.-K., & Brown, G. D. (2002) · Tetrahedron · doi:10.1016/s0040-4020(01)01193-0 · Cited by 129
Wallaart, T. E., van Uden, W., Lubberink, H. G. M., Woerdenbag, H. J., Pras, N., & Quax, W. J. (1999) · Journal of Natural Products · doi:10.1021/np980370p · Cited by 129
Mercke, P., Crock, J., Croteau, R., & Brodelius, P. E. (1999) · Archives of Biochemistry and Biophysics · doi:10.1006/abbi.1999.1358 · Cited by 127
Studies on the Constituents of Artemisia annua Part II*
You-you, T., Mu-yun, N., Yu-rong, Z., Lan-na, L., Shu-lian, C., Mu-qun, Z., Xiu-zhen, W., Zheng, J., & Xiao-tian, L. (1982) · Planta Medica · doi:10.1055/s-2007-971424 · Cited by 125
Neue furanoeremophilane und andere sesquiterpene aus vertretern der gattung Euryops
Bohlmann, F., & Zdero, C. (1978) · Phytochemistry · doi:10.1016/s0031-9422(00)94305-x · Cited by 112
Research works printed but not linked: 7
- Christofides, 1983, Secondary isotope multiplet NMR spectroscopy of partially labeled entities, Carbon-13 SIMPLE NMR of carbohydrates. Journal of the American Chemical Society, 105, 5099
- Coll, 1989, Tropical marine algae, VI. New monoterpenes from several collections of Chondrococcus hornemanii (Rhodophyta, Gigartinales, Rizophyllidaceae). Australian Journal of Chemistry, 42, 1983
- Jeremic, 1979, Flavonols from Artemisia annua L, Bulletin de la Societe Chimique Beograd 44, 615-618 (Chem. Abs, 92, 211806
- Kuo, 1992, 8α,12-Dihydroxycedrane, Journal of Chemical Research (S), 382
- Piers, 1990, A (Z)-ethylidenecyclopentane annulation method, Total synthesis of (+/−)-anhydrooplopanone, (+/−)-oplopanone, and (+/−)-8-epi-oplopanone. Journal of Organic Chemistry, 55, 2380
- Stefanovic, 1977, Chemical transformations of arteannuin B—cadinane sesquiterpenic lactone—isolated from Artemisia annua L, Bulletin de la Societe Chimique Beograd 42, 227-236. (Chem. Abs, 87, 168213
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Cited by
Sorted by citations
The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao)
Brown, G. D. (2010) · Molecules · doi:10.3390/molecules15117603 · Cited by 363
Self-citationIn vivo transformations of dihydroartemisinic acid in Artemisia annua plants
Brown, G. D., & Sy, L.-K. (2004) · Tetrahedron · doi:10.1016/j.tet.2003.11.070 · Cited by 183
Initial and Bulk Extraction of Natural Products Isolation
Seidel, V. (2012) · Methods in molecular biology · doi:10.1007/978-1-61779-624-1_2 · Cited by 121
Bilia, A. R., de Magalhães, P. M., Bergonzi, M. C., & Vincieri, F. F. (2006) · Phytomedicine · doi:10.1016/j.phymed.2006.01.008 · Cited by 115
Synthesis of highly strained terpenes by non-stop tail-to-head polycyclization
Pronin, S. V., & Shenvi, R. A. (2012) · Nature Chemistry · doi:10.1038/nchem.1458 · Cited by 109
Metadata
- 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)
- 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
- 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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