Two azafluoranthene alkaloids and a phytoecdysone from the stems of Cyclea barbata
Abstract
Two new azafluoranthene alkaloids (1 and 2), and a new phytoecdysone (3), were isolated from the stems of Cyclea barbata Miers, together with six known compounds (4-9). Their structures were elucidated by spectroscopic data analysis and comparison with published data. This is the first report of azafluoranthene alkaloids (1 and 2) and phytoecdysones (3, 8, and 9) from Cyclea genus. In in vitro bioassay, four isolates (3, 5, 6, and 9) showed moderate hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced toxicity in HepG2 cells.
Integrity signals
Registry
Cites
Statistics
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?
Cycleasterone A showed moderate hepatoprotective activity against APAP-induced toxicity in HepG2 cells.
“Evaluated hepatoprotective activity against APAP-induced toxicity in HepG2 cells and moderate activity have been observed.”
From The Phytochemical, Biological, and Medicinal Attributes of Phytoecdysteroids: An Updated Review (2021) · cites this paper as [135]
Cites
Bari, L. D., Pescitelli, G., Pratelli, C., Pini, D., & Salvadori, P. A. (2001) · The Journal of Organic Chemistry · doi:10.1021/jo010136v · Cited by 364 · see citing works
Frelek, J., Klimek, A., & Ruśkowska, P. (2003) · Current Organic Chemistry · doi:10.2174/1385272033486576 · Cited by 84 · see citing works
Cytotoxic and Antimalarial Bisbenzylisoquinoline Alkaloids from Cyclea barbata
Lin, L.-Z., Shieh, H.-L., Angerhofer, C. K., Pezzuto, J. M., Cordell, G. A., Xue, L., Johnson, M. E., & Ruangrungsi, N. (1993) · Journal of Natural Products · doi:10.1021/np50091a004 · Cited by 83 · see citing works
Protoberberine alkaloids from Coscinium fenestratum
Pinho, P. M. M., Pinto, M. M. M., Kijjoa, A., Pharadai, K., Dı́az, J. G., & Herz, W. (1992) · Phytochemistry · doi:10.1016/0031-9422(92)80301-t · Cited by 70 · see citing works
Vokáč, K., Buděšńský, M., Harmatha, J., & Kohoutová, J. (1998) · Phytochemistry · doi:10.1016/s0031-9422(98)00448-8 · Cited by 63 · see citing works
Azafluoranthene alkaloids. New structural type
Cava, M. P., Buck, K. T., & DaRocha, A. I. (1972) · Journal of the American Chemical Society · doi:10.1021/ja00771a087 · Cited by 35 · see citing works
Azafluoranthene Alkaloids from Cissampelos pareira.
Morita, H., Matsumoto, K., Takeya, K., & Itokawa, H. (1993) · Chemical and Pharmaceutical Bulletin · doi:10.1248/cpb.41.1307 · Cited by 29 · see citing works
Bisbenzylisoquinoline Alkaloids from Cyclea barbata
Guinaudeau, H., Lin, L., Ruangrungsi, N., & Cordell, G. A. (1993) · Journal of Natural Products · doi:10.1021/np50101a020 · Cited by 24 · see citing works
A Route to Azafluoranthene Natural Products Through Direct Arylation
Ponnala, S., & Harding, W. W. (2013) · European Journal of Organic Chemistry · doi:10.1002/ejoc.201201190 · Cited by 21 · see citing works
Shi, Y., Hu, K., Pescitelli, G., Liu, M., Li, X., Du, X., Xiao, W., Sun, H., & Puno, P. (2018) · Organic Letters · doi:10.1021/acs.orglett.8b00149 · Cited by 21 · see citing works
Studies on Indonesian Medicinal Plants. V. The Alkaloids of Anamirta cocculus
Verpoorte, R., Siwon, J., Tieken, M. E. M., & Svendsen, A. B. (1981) · Journal of Natural Products · doi:10.1021/np50014a013 · Cited by 19 · see citing works
Two New 8-Oxotetrahydroprotoberberine Alkaloids, Gusanlung A and B, fromAcangelisia gusanlung
Zhang, J., & Zhong-liang, C. (1991) · Planta Medica · doi:10.1055/s-2006-960150 · Cited by 18 · see citing works
Berova, N. D., Harada, N., & Nakanishi, K. (2014) · Elsevier eBooks · doi:10.1016/b978-0-12-409547-2.11170-9 · Cited by 10 · see citing works
Flagged first, then by citations
Cited by
Sorted by citations
The Phytochemical, Biological, and Medicinal Attributes of Phytoecdysteroids: An Updated Review
Das, N., Mishra, S. K., Bishayee, A., Ali, E. S., & Bishayee, A. (2021) · Acta Pharmaceutica Sinica B · doi:10.1016/j.apsb.2020.10.012 · Cited by 115 · see citing works
“These ecdysteroids are 11a-hydroxyrubrosterone (130)(104), dacryhainansterone (131)(105), calonysterone (132)(105), cyanosterone A (133)(106), cyanosterone B (134)(107), 22-oxo-ajugasterone C (135)(108), 22-oxo-20-hydroxyecdysone (136)(108), ajugasterone C 2acetate (137)(109), shidasterone3-acetate (138)(109), isolate…”
BackgroundArif, Y., Singh, P., Bajguz, A., & Hayat, S. (2022) · International Journal of Molecular Sciences · doi:10.3390/ijms23158664 · Cited by 50 · see citing works
Hepatoprotective natural products
Bachar, S. C., Bachar, R., Jannat, K., Jahan, R., & Rahmatullah, M. (2020) · Annual reports in medicinal chemistry · doi:10.1016/bs.armc.2020.06.003 · Cited by 21 · see citing works
Hao, D., Xu, L., Zheng, Y., Lyu, H.-Y., & Xiao, P. (2022) · Chinese Journal of Integrative Medicine · doi:10.1007/s11655-022-3576-x · Cited by 12 · see citing works
Cyclea barbata L. Miers.: Penggunaan tradisional, fitokimia, dan aktivitas farmakologi
Febrianto, S., Praharsini, F. V., Annas, Z. F., & Hanifa, N. I. (2022) · Sasambo Journal of Pharmacy · doi:10.29303/sjp.v3i2.178 · Cited by 4 · see citing works
Ren, W., Tian, Z., Dong, M., Ma, Y., Xu, L., Jiang, H., & Liu, Y. (2020) · Biochemical Systematics and Ecology · doi:10.1016/j.bse.2020.104047 · Cited by 3 · see citing works
Antibacterial and Antitumor Activities of Synthesized Sarumine Derivatives
Yang, F., Jia, B., Wen, H., Yang, X., & Ma, Y. (2024) · International Journal of Molecular Sciences · doi:10.3390/ijms252212412
Spectroscopic Techniques for the Characterization of Ecdysteroids
Pogam, P. L., & Beniddir, M. A. (2026) · Springer eBooks · doi:10.1007/978-981-95-8423-9_2
Fylaktakidou, K. C., Manta, S., Koumbis, A. E., & Varvoglis, A. G. (2026) · Phytochemistry · doi:10.1016/j.phytochem.2026.115045
- Authors
- Wang, X.-J., Zhang, Q., Peng, Y.-R., Li, L., Qu, J., Liu, Y.-B., Xu, S., Ma, S.-G., Li, Y., Zou, Z.-M., Wang, R.-B., & Yu, S.-S.
- Affiliations
- State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China;
- Guangxi University of Chinese Medicine (CN)
- Chinese Academy of Medical Sciences & Peking Union Medical College (CN)
- Corresponding author
- Yu, Shi-Shan
- Venue
- Journal of Asian Natural Products Research
- Publisher
- Informa UK Limited
- Published
- 2019-02-09
- Volume
- 21
- Issue
- 3
- Pages
- 217-226
- ISSN
- 1028-6020 (ISSN-L)
- 1477-2213
- OpenAlex
- W2913429906
- Cited by
- 9
- References
- 13
- Citations by year
- 2026: 2 · 2024: 1 · 2022: 3 · 2020: 3
- FWCI
- 1.11
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of Asian Natural Products Research (publishedVersion)
- PubMed (publishedVersion)
- Funders
- Natural Science Foundations of China
- Young Elite Scientists Sponsorship Program by CAST (QNRC001)
- Topics
- Life Sciences › Agricultural and Biological Sciences › Plant Science › Phytochemistry and Biological Activities
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Phytochemical Studies and Bioactivities
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Biochemistry › Traditional and Medicinal Uses of Annonaceae
- Keywords
- phytoecdysone, Cyclea barbata, natural product isolation, structure elucidation, hepatoprotection, HepG2 cells, stem
- MeSH terms
- Alkaloids, Antineoplastic Agents, Phytogenic, Cell Survival, Ecdysone, Humans, Models, Molecular, Phytosterols, Molecular Structure, Cyclea, Hep G2 Cells
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