Cytotoxic Terpenoids and Flavonoids from Artemisia annua
Abstract
The cytotoxic activity of nine terpenoids and flavonoids isolated from Artemisia annua was tested in vitro on several human tumor cell lines. These compounds are artemisinin, deoxyartemisinin, artemisinic acid, arteannuin-B, stigmasterol, friedelin, friedelan-3 beta-ol, artemetin, and quercetagetin 6,7,3',4'-tetramethyl ether. Friedelane-type triterpenoids were isolated for the first time from this plant. Artemisinin and quercetagetin 6,7,3',4'-tetramethyl ether showed significant cytotoxicity against P-388, A-549, HT-29, MCF-7, and KB tumor cells.
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Artemisinic acid, arteannuin B, and artemisinin are the most abundant representatives of the amorphane/cadinane class of natural products from A. annua.
“Artemisinic acid (473) [105,147,148], arteannuin B (462) [105,147,149] and artemisinin (495) [105,147,150] are the most abundant representatives of this class of natural products”
From The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao) (2010) · cites this paper as [105]
Artemisinic acid, arteannuin B, and artemisinin were amongst the first sesquiterpenes to be reported from A. annua.
“and were amongst the first sesquiterpenes to be reported from A. annua.”
From The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao) (2010) · cites this paper as [105]
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Li, H., Yu, Y., Wang, Z., Yang, J., Xiao, W. L., & Yao, X. (2014) · Magnetic Resonance in Chemistry · doi:10.1002/mrc.4168 · Cited by 12 · see citing works
Gaspar‐Pintiliescu, A., Seciu‐Grama, A., Miculescu, F., et al. (2018) · Journal of Bioactive and Compatible Polymers · doi:10.1177/0883911518783216 · Cited by 12 · see citing works
Wu, Y., Jiang, X., Zhang, L., & Zhou, Y. (2018) · Journal of Essential Oil Bearing Plants · doi:10.1080/0972060x.2019.1574244 · Cited by 12 · see citing works
Natural products targeting ferroptosis pathways in cancer therapy (Review)
Na, X., Li, L., Liu, D., He, J., Zhang, L., & Zhou, Y. (2024) · Oncology Reports · doi:10.3892/or.2024.8782 · Cited by 13 · see citing works
“The common structure of a peroxide‑internal bridge is essential for the anti‑tumor effects of ARTCs (88,89) ARTCs can cause cell cycle arrest of tumor cells (90), inhibit angiogenesis (91), inhibit cell metastasis and invasion (92), cause DNA damage (93) and induce apoptosis and ferroptosis (25,94).”
BackgroundZhu, X., Bi, C., Cao, W. W., et al. (2024) · Journal of Materials Chemistry B · doi:10.1039/d4tb01237b · Cited by 10 · see citing works
Cao, Y., Tan, X., Zhan, G., Li, Q., Wang, H., & Li, Z. (2022) · AIChE Journal · doi:10.1002/aic.17711 · Cited by 10 · see citing works
Two new sesquiterpene lactones and other chemical constituents of Artemisia roxbughiana
Phan, M. G., Tran, T. T. N., Phan, T. S., Otsuka, H., & Matsunami, K. (2012) · Biochemical Systematics and Ecology · doi:10.1016/j.bse.2012.07.027 · Cited by 10 · see citing works
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Artemisia annua organic solvent extract, processed by supercritical CO2
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Preliminary Case Series of Artemisinin for Prostate Cancer in a Naturopathic Practice
Yarnell, E. L. (2015) · Journal of Restorative Medicine · doi:10.14200/jrm.2015.4.0103 · Cited by 8 · see citing works
“Quercetagetin 6,7,3′,4′-tetramethyl ether, a flavonoid from Artemisia annua, has also been shown to be cytoxic in vitro against several cancer cell lines.(3)”
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“absinthium have been reported to contain flavonoids [26-28], thymol, and carvacrol as well as other phenolic compounds [29].”
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- Authors
- Zheng, G.-Q.
- Venue
- Planta Medica
- Publisher
- Georg Thieme Verlag KG
- Published
- 1994-02
- Volume
- 60
- Issue
- 01
- Pages
- 54-57
- ISSN
- 0032-0943 (ISSN-L)
- 1439-0221
- OpenAlex
- W2094117413
- Cited by
- 139
- References
- 0
- Citations by year
- 2025: 2 · 2024: 8 · 2023: 3 · 2022: 7 · 2021: 6 · 2020: 9 · 2019: 1 · 2018: 6 · 2017: 8 · 2016: 7 · 2015: 8 · 2014: 11 · 2013: 4 · 2012: 5
- FWCI
- 0.67
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Planta Medica (publishedVersion)
- PubMed (publishedVersion)
- Funders
- National Institutes of Health (1r43ca056262-01a1)
- National Cancer Institute (CA 56262)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Cancer Research › Sesquiterpenes and Asteraceae Studies
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Phytochemical compounds biological activities
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Natural product bioactivities and synthesis
- Keywords
- Artemisia annua, cytotoxicity, terpenoids, flavonoids, artemisinin, artemisinic acid, arteannuin B, stigmasterol, friedelin, artemetin, quercetagetin, anticancer activity, human cancer cell lines
- MeSH terms
- Animals, Antineoplastic Agents, Phytogenic, Drugs, Chinese Herbal, Flavonoids, Humans, Leukemia P388, Terpenes, Tumor Cells, Cultured, Molecular Structure, Mice
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