Hyperuralones A and B, New Acylphloroglucinol Derivatives with Intricately Caged Cores from Hypericum uralum
| Autor: | Yang Liao, Jun-Zeng Ma, Jing-Jing Zhang, Lixin Yang, Gang Xu, Xing-Wei Yang, Qiu-Li Xiao, Jing Yang |
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| Rok vydání: | 2014 |
| Předmět: |
Annulation
Hypericum uralum Molecular Structure biology Stereochemistry Organic Chemistry HL-60 Cells Phloroglucinol biology.organism_classification Antineoplastic Agents Phytogenic Biochemistry chemistry.chemical_compound Hyperuralone B Biosynthesis chemistry Intramolecular force Humans Molecule Drug Screening Assays Antitumor Physical and Theoretical Chemistry Nuclear Magnetic Resonance Biomolecular Hypericum Human cancer Diels–Alder reaction |
| Zdroj: | Organic Letters. 16:4912-4915 |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | Hyperuralone A (1), a polycyclic polyprenylated acylphloroglucinol possessing an unprecedented tetracyclo[5.3.1.1(4,9).0(4,11)]-dodecane core, was characterized from Hypericum uralum together with hyperuralone B (2), a congener with another complex caged skeleton. Their structures were determined by extensive spectroscopic analysis and ECD calculations. A plausible biosynthetic pathway of their intriguing architectures via intramolecular Die Is Alder reactions was also proposed. Compound 1 exhibited obviously cytotoxic activities against five human cancer cell lines in vitro (IC50 4.6-14.4 mu M). |
| Databáze: | OpenAIRE |
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