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.
Overview
Integrity signals
Registry
Cites
Statistics
Verification
Claims the paper makes
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
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
Terpenoids and Flavonoids from Artemisia Species
Tang, H., Hu, J., Yang, L., & Tan, R. (2000) · Planta Medica · doi:10.1055/s-2000-8538 · Cited by 104
Wallaart, T. E., Pras, N., & Quax, W. J. (1999) · Journal of Natural Products · doi:10.1021/np9900122 · Cited by 101
Artemisitene, a New Sesquiterpene Lactone Endoperoxide fromArtemisia annua
Acton, N., & Klayman, D. L. (1985) · Planta Medica · doi:10.1055/s-2007-969543 · Cited by 100
Terpenoids from Artemisia annua and constituents of its essential oil
Ahmad, A., & Misra, L. N. (1994) · Phytochemistry · doi:10.1016/0031-9422(94)85021-6 · Cited by 87
Coniferaldehyde derivatives from tissue culture of Artemisia annua and Tanacetum parthenium
Sy, L., & Brown, G. D. (1999) · Phytochemistry · doi:10.1016/s0031-9422(98)00607-4 · Cited by 84
Terpenoids of Alisma orientale rhizome and the crude drug alismatis rhizoma
Nakajima, Y., Satoh, Y., Katsumata, M., Tsujiyama, K., Ida, Y., & SHOJI, J. (1994) · Phytochemistry · doi:10.1016/s0031-9422(00)97024-9 · Cited by 82
Volatile constituents of Artemisia annua L. (Asteraceae)
Woerdenbag, H. J., Bos, R., Salomons, M. C., Hendriks, H., Pras, N., & Malingré, T. M. (1993) · Flavour and Fragrance Journal · doi:10.1002/ffj.2730080303 · Cited by 73
Two New Compounds from Artemisia annua
Brown, G. D. (1992) · Journal of Natural Products · doi:10.1021/np50090a006 · Cited by 70
A new type of sesqiterpene lactone isolated from
Jeremić, D., Jokić, A., Behbud, A., & Stefanović, M. (1973) · Tetrahedron Letters · doi:10.1016/s0040-4039(01)96314-2 · Cited by 69
Sy, L., Brown, G. D., & Haynes, R. K. (1998) · Tetrahedron · doi:10.1016/s0040-4020(98)00148-3 · Cited by 66
Three sesquiterpenes from Artemisia annua
Sy, L., & Brown, G. D. (1998) · Phytochemistry · doi:10.1016/s0031-9422(97)01047-9 · Cited by 62
Terpenoids from some Japanese liverworts
Nagashima, F., Toyota, M., & Asakawa, Y. (1990) · Phytochemistry · doi:10.1016/0031-9422(90)83031-u · Cited by 61
[Studies on the constituents of Artemisia annua L. (author's transl)].
Tu, Y. Y., Ni, M., Zhong, Y. R., Li, L., Cui, S.-Y., ZHANG, M., Wang, X. Z., & Liang, X. (1981) · PubMed · Cited by 57
Phytene-1,2-diol from Artemisia annua
Brown, G. D. (1994) · Phytochemistry · doi:10.1016/s0031-9422(00)89762-9 · Cited by 49
Total Synthesis of (+)-Arteanniun M Using the Tandem Oxy-Cope/Ene Reaction
Barriault, L., & Deon, D. H. (2001) · Organic Letters · doi:10.1021/ol015970l · Cited by 47
Barrero, A. F., Herrador, M. M., del Moral, J. F. Q., Álvarez-Manzaneda, R., Portal, D., Gavín, J. A., GRAVALOS, D. G., Simmonds, M. S. J., & Blaney, W. M. (1999) · Phytochemistry · doi:10.1016/s0031-9422(99)00047-3 · Cited by 47
Methoxylated flavones and coumarins from Artemisia annua
Shilin, Y., ROBERTS, M. F., & Phillipson, J. D. (1989) · Phytochemistry · doi:10.1016/s0031-9422(00)97776-8 · Cited by 43
Further ineupatorolide-like germacranolides from Inula cuspidata
Bohlmann, F., Singh, P., & Jakupovic, J. (1982) · Phytochemistry · doi:10.1016/0031-9422(82)80034-4 · Cited by 42
Cadinanes from Artemisia annua that may be intermediates in the biosynthesis of artemisinin
Brown, G. D. (1994) · Phytochemistry · doi:10.1016/s0031-9422(00)89788-5 · Cited by 41
Germacranolides from Artemisia myriantha and their conformation
Wong, H., & Brown, G. D. (2002) · Phytochemistry · doi:10.1016/s0031-9422(01)00479-4 · Cited by 41
The role of the 12-carboxylic acid group in the spontaneous autoxidation of dihydroartemisinic acid
Sy, L.-K., & Brown, G. D. (2002) · Tetrahedron · doi:10.1016/s0040-4020(01)01192-9 · Cited by 36
Self-citationEudesmane sesquiterpenes from Artemisia eriopoda
Hu, J., Bai, S., & Jia, Z. (1996) · Phytochemistry · doi:10.1016/0031-9422(96)00325-1 · Cited by 36
Sy, L.-K., & Brown, G. D. (2001) · Phytochemistry · doi:10.1016/s0031-9422(01)00358-2 · Cited by 36
Misra, L. N., Ahmad, A., Thakur, R. S., Lotter, H., & Wagner, H. (1993) · Journal of Natural Products · doi:10.1021/np50092a005 · Cited by 32
Guaianolides and other constituents of Helianthus microcephalus
Gutierrez, A. B., & Herz, W. (1988) · Phytochemistry · doi:10.1016/0031-9422(88)80131-6 · Cited by 32
Epi-Deoxyarteannuin B and 6,7-Dehydroartemisinic Acid from Artemisia annua
El‐Feraly, F. S., Al-Meshal, I. A., & Khalifa, S. I. (1989) · Journal of Natural Products · doi:10.1021/np50061a031 · Cited by 31
Flavonoids and chromenes from Artemisia annua
Yang, S., ROBERTS, M. F., O’Neill, M. J., Bučar, F., & Phillipson, J. D. (1995) · Phytochemistry · doi:10.1016/0031-9422(94)00591-g · Cited by 31
Artemisinin G: A Sesquiterpene fromArtemisia annua
Wei, Z.-X., Pan, J.-P., & Li, Y. (1992) · Planta Medica · doi:10.1055/s-2006-961470 · Cited by 29
Secondary metabolism in tissue culture of Artemisia annua
Brown, G. D. (1994) · Journal of Natural Products · doi:10.1021/np50109a015 · Cited by 28
Sy, L.-K., Zhu, N.-Y., & Brown, G. D. (2001) · Tetrahedron · doi:10.1016/s0040-4020(01)00711-6 · Cited by 27
Chromenes and benzofurans from Ageratina glechonophylla
González, A. G., Barrera, J. B., Yanes, A. C., Dı́az, J. G., & Pérez, E. M. R. (1989) · Phytochemistry · doi:10.1016/s0031-9422(00)98024-5 · Cited by 26
Annphenone, a phenolic acetophenone from Artemisia annua
Singh, A., Pathak, V., & Agrawal, P. K. (1997) · Phytochemistry · doi:10.1016/s0031-9422(96)00424-4 · Cited by 26
Sy, L.-K., & Brown, G. D. (1999) · Tetrahedron · doi:10.1016/s0040-4020(98)01021-7 · Cited by 25
Volatile Constituents ofArtemisia annua
Woerdenbag, H. J., Bos, R., Salomons, M. C., Hendriks, H., Pras, N., & Malingré, T. M. (1992) · Planta Medica · doi:10.1055/s-2006-961701 · Cited by 25
Sesquiterpene lactones and other constituents from Hymenoxys richardsonii and H. subintegra
Ahmed, A. (1995) · Phytochemistry · doi:10.1016/0031-9422(95)00014-x · Cited by 25
Isolation of (2,8)-germacra-1(11),5(12),6-trien-2-ol acetate from the brown alga
Fattorusso, E., Magno, S., Mayol, L., Amico, V., Oriente, G., Piattelli, M., & Tringali, C. (1978) · Tetrahedron Letters · doi:10.1016/s0040-4039(01)95167-6 · Cited by 21
Bisnor-cadinanes from Artemisia annua and definitive 13C NMR assignments of β-arteether
Misra, L. N., Ahmad, A., Thakur, R. S., & Jakupovic, J. (1993) · Phytochemistry · doi:10.1016/0031-9422(93)85111-4 · Cited by 21
α- and β-Myrcene hydroperoxide from Artemisia annua
Rücker, G., Mayer, R., & Manns, D. (1987) · Journal of Natural Products · doi:10.1021/np50050a038 · Cited by 20
Sy, L., Cheung, K., Zhu, N., & Brown, G. D. (2001) · Tetrahedron · doi:10.1016/s0040-4020(01)00633-0 · Cited by 20
Biomimetic synthesis of arteannuin h and the 3,2-rearrangement of allylic hydroperoxides
Sy, L., Ngo, K., & Brown, G. D. (1999) · Tetrahedron · doi:10.1016/s0040-4020(99)00987-4 · Cited by 19
Synthesis of 6,7-dehydroartemisinic acid
Sy, L.-K., & Brown, G. D. (2001) · Journal of the Chemical Society, Perkin Transactions 1 · doi:10.1039/b104471k · Cited by 19
Self-citationNgo, K., & Brown, G. D. (1999) · Tetrahedron · doi:10.1016/s0040-4020(99)00986-2 · Cited by 17
Wong, H.-F., & Brown, G. D. (2002) · Journal of Chemical Research · doi:10.3184/030823402103170376 · Cited by 17
Self-citationEpimerization in acid degradation products of artemisinin
Hui, S.-M., Ngo, K., & Brown, G. D. (1997) · Journal of the Chemical Society Perkin Transactions 1 · doi:10.1039/a702714a · Cited by 15
Annuadiepoxide, a new polyacetylene from the aerial parts of Artemisia annua
Manns, D., & Hartmann, R. (1992) · Journal of Natural Products · doi:10.1021/np50079a003 · Cited by 15
Acid-catalysed rearrangement of caryophyllene oxide
Tsui, W.-Y., & Brown, G. D. (1996) · Journal of the Chemical Society Perkin Transactions 1 · doi:10.1039/p19960002507 · Cited by 13
Leino, R. P., Luttikhedde, H. J. G., Långstedt, L., & Penninkangas, A. (2002) · Tetrahedron Letters · doi:10.1016/s0040-4039(02)00766-9 · Cited by 8
Autoxidation of allohimachalol
Ngo, K., & Brown, G. D. (1999) · Tetrahedron · doi:10.1016/s0040-4020(99)00938-2 · Cited by 7
Chemical transformations of arteannuin B
Gai, Y., Ya-Ping, Z., & Liang-Quan, L. (1983) · Acta Chimica Sinica · doi:10.1002/cjoc.19830010106 · Cited by 6
Coumarins from Artemisia annua
Saitbaeva, I. M., & Sidyakin, G. P. (1970) · Chemistry of Natural Compounds · doi:10.1007/bf00565356 · Cited by 5
ChemInform Abstract: 8α,12‐Dihydroxycedrane: A New Sesquiterpene from Juniperus chinensis Linn.
Kuo, Y., & CHEN, W. ‐. (1993) · ChemInform · doi:10.1002/chin.199311255 · Cited by 5
Baeva, R. T., Nabizade, L. I., Zapesochnaya, G. G., & Karryev, M. O. (1988) · Chemistry of Natural Compounds · doi:10.1007/bf00596766 · Cited by 5
Ngo, K., & Brown, G. D. (2000) · Journal of Chemical Research · doi:10.3184/030823400103166599 · Cited by 5
Wong, H., & Brown, G. D. (2002) · ChemInform · doi:10.1002/chin.200228231 · Cited by 3
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
- Wu, 1984, Studies on structure and synthesis of arteanuin and its related compound, Acta Chimica Sinica, 42, 596
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
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review