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Article: Structurally diverse spirocyclic polycyclic polyprenylated acylphloroglucinols from Hypericum ascyron Linn. and their anti-tumor activity

TitleStructurally diverse spirocyclic polycyclic polyprenylated acylphloroglucinols from Hypericum ascyron Linn. and their anti-tumor activity
Authors
KeywordsHCT116 cells
Hypericaceae
Hypericum ascyron Linn.
Polycyclic polyprenylated acylphloroglucinols
Spirocyclic polyprenylated acylphloroglucinols
Zebrafish model
Issue Date2023
Citation
Phytochemistry, 2023, v. 212, article no. 113727 How to Cite?
AbstractTen 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 Identifierhttp://hdl.handle.net/10722/343424
ISSN
2023 Impact Factor: 3.2
2023 SCImago Journal Rankings: 0.667

 

DC FieldValueLanguage
dc.contributor.authorHu, Ya Li-
dc.contributor.authorYue, Grace Gar Lee-
dc.contributor.authorLi, Xing Ren-
dc.contributor.authorXu, Gang-
dc.contributor.authorLau, Clara Bik San-
dc.date.accessioned2024-05-10T09:08:01Z-
dc.date.available2024-05-10T09:08:01Z-
dc.date.issued2023-
dc.identifier.citationPhytochemistry, 2023, v. 212, article no. 113727-
dc.identifier.issn0031-9422-
dc.identifier.urihttp://hdl.handle.net/10722/343424-
dc.description.abstractTen 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.languageeng-
dc.relation.ispartofPhytochemistry-
dc.subjectHCT116 cells-
dc.subjectHypericaceae-
dc.subjectHypericum ascyron Linn.-
dc.subjectPolycyclic polyprenylated acylphloroglucinols-
dc.subjectSpirocyclic polyprenylated acylphloroglucinols-
dc.subjectZebrafish model-
dc.titleStructurally diverse spirocyclic polycyclic polyprenylated acylphloroglucinols from Hypericum ascyron Linn. and their anti-tumor activity-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1016/j.phytochem.2023.113727-
dc.identifier.pmid37207991-
dc.identifier.scopuseid_2-s2.0-85159598352-
dc.identifier.volume212-
dc.identifier.spagearticle no. 113727-
dc.identifier.epagearticle no. 113727-

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