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- Publisher Website: 10.1016/j.phytochem.2023.113727
- Scopus: eid_2-s2.0-85159598352
- PMID: 37207991
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Article: Structurally diverse spirocyclic polycyclic polyprenylated acylphloroglucinols from Hypericum ascyron Linn. and their anti-tumor activity
Title | Structurally diverse spirocyclic polycyclic polyprenylated acylphloroglucinols from Hypericum ascyron Linn. and their anti-tumor activity |
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Authors | |
Keywords | HCT116 cells Hypericaceae Hypericum ascyron Linn. Polycyclic polyprenylated acylphloroglucinols Spirocyclic polyprenylated acylphloroglucinols Zebrafish model |
Issue Date | 2023 |
Citation | Phytochemistry, 2023, v. 212, article no. 113727 How to Cite? |
Abstract | Ten spirocyclic polycyclic polyprenylated acylphloroglucinols (PPAP), hunascynols A–J (1–10), and 12 known analogs were isolated from the aerial parts of Hypericum ascyron Linn. Compounds 1 and 2, which share a 1,2-seco-spirocyclic PPAP skeleton, could be derived from spirocyclic PPAP, with a common octahydrospiro[cyclohexan-1,5′-indene]-2,4,6-trione core, through a cascade of Retro-Claisen, keto-enol tautomerism, and esterification reactions. Aldolization of normal spirocyclic PPAP yielded 3, which has a caged framework with a 6/5/6/5/6 ring system. The structures of these compounds were determined using spectroscopy and X-ray diffraction. The inhibitory activities of all isolates were tested in three human cancer cell lines and a zebrafish model. Compounds 1 and 2 displayed moderate cytotoxicity against HCT116 cells (IC50 6.87 and 9.86 μM, respectively). The mechanisms of these compounds were evaluated using Western blot assays. Compounds 3 and 5 inhibited the growth of sub-intestinal vessels in zebrafish embryos. Further, the target genes were screened using real-time PCR. |
Persistent Identifier | http://hdl.handle.net/10722/343424 |
ISSN | 2023 Impact Factor: 3.2 2023 SCImago Journal Rankings: 0.667 |
DC Field | Value | Language |
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dc.contributor.author | Hu, Ya Li | - |
dc.contributor.author | Yue, Grace Gar Lee | - |
dc.contributor.author | Li, Xing Ren | - |
dc.contributor.author | Xu, Gang | - |
dc.contributor.author | Lau, Clara Bik San | - |
dc.date.accessioned | 2024-05-10T09:08:01Z | - |
dc.date.available | 2024-05-10T09:08:01Z | - |
dc.date.issued | 2023 | - |
dc.identifier.citation | Phytochemistry, 2023, v. 212, article no. 113727 | - |
dc.identifier.issn | 0031-9422 | - |
dc.identifier.uri | http://hdl.handle.net/10722/343424 | - |
dc.description.abstract | Ten spirocyclic polycyclic polyprenylated acylphloroglucinols (PPAP), hunascynols A–J (1–10), and 12 known analogs were isolated from the aerial parts of Hypericum ascyron Linn. Compounds 1 and 2, which share a 1,2-seco-spirocyclic PPAP skeleton, could be derived from spirocyclic PPAP, with a common octahydrospiro[cyclohexan-1,5′-indene]-2,4,6-trione core, through a cascade of Retro-Claisen, keto-enol tautomerism, and esterification reactions. Aldolization of normal spirocyclic PPAP yielded 3, which has a caged framework with a 6/5/6/5/6 ring system. The structures of these compounds were determined using spectroscopy and X-ray diffraction. The inhibitory activities of all isolates were tested in three human cancer cell lines and a zebrafish model. Compounds 1 and 2 displayed moderate cytotoxicity against HCT116 cells (IC50 6.87 and 9.86 μM, respectively). The mechanisms of these compounds were evaluated using Western blot assays. Compounds 3 and 5 inhibited the growth of sub-intestinal vessels in zebrafish embryos. Further, the target genes were screened using real-time PCR. | - |
dc.language | eng | - |
dc.relation.ispartof | Phytochemistry | - |
dc.subject | HCT116 cells | - |
dc.subject | Hypericaceae | - |
dc.subject | Hypericum ascyron Linn. | - |
dc.subject | Polycyclic polyprenylated acylphloroglucinols | - |
dc.subject | Spirocyclic polyprenylated acylphloroglucinols | - |
dc.subject | Zebrafish model | - |
dc.title | Structurally diverse spirocyclic polycyclic polyprenylated acylphloroglucinols from Hypericum ascyron Linn. and their anti-tumor activity | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1016/j.phytochem.2023.113727 | - |
dc.identifier.pmid | 37207991 | - |
dc.identifier.scopus | eid_2-s2.0-85159598352 | - |
dc.identifier.volume | 212 | - |
dc.identifier.spage | article no. 113727 | - |
dc.identifier.epage | article no. 113727 | - |