RESUMEN
Hyperuralones C-H (1-6), six new 1,9-seco-bicyclic polyprenylated acylphloroglucinols (1,9-seco-BPAPs) derived from the normal polyprenylated acylphloroglucinols with a bicyclo[3.3.1]nonane-2,4,9-trione core, together with six known analogues, were isolated from the aerial parts of Hypericum uralum. The structures of 1-6 were elucidated on the basis of the interpretation of NMR and MS spectroscopic data. The structure of attenuatumione B, a known compound isolated from H. attenuatum, was revised to that of a 1,9-seco-BPAP by NMR spectroscopic analysis and previous biomimetic synthesis methods. The inhibitory activities of these isolates on acetylcholinesterase were tested, and compounds 1 and 2 exhibited moderate activities with IC50 values of 9.6 and 7.1 µM, respectively.
Asunto(s)
Inhibidores de la Colinesterasa/aislamiento & purificación , Hypericum/química , Floroglucinol/análogos & derivados , Floroglucinol/aislamiento & purificación , Acetilcolinesterasa/efectos de los fármacos , Inhibidores de la Colinesterasa/química , Inhibidores de la Colinesterasa/farmacología , Humanos , Concentración 50 Inhibidora , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Floroglucinol/químicaRESUMEN
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 Diels-Alder reactions was also proposed. Compound 1 exhibited obviously cytotoxic activities against five human cancer cell lines in vitro (IC50 4.6-14.4 µM).
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Hypericum/química , Floroglucinol/análogos & derivados , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Células HL-60 , Humanos , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Floroglucinol/química , Floroglucinol/aislamiento & purificación , Floroglucinol/farmacologíaRESUMEN
ABSTRACT: Medicinal plants have a long history of use in China to treat diabetic symptoms. Ancient Chinese medical manuscripts and ethnobotanical surveys document plant remedies that continue to be actively used in China for the treatment of diabetic symptoms. Based on a systematic ancient Chinese medical manuscripts review in combination with ethnobotanical survey, 16 medicinal plants for the traditional treatment of diabetic symptoms were identified for the evaluation of anti-insulin resistance bioactivity. The biological activity of 16 medicinal plants was tested on dexamethasone (DXMS)-induced insulin resistant HepG2 cells. The result shows that 11 of the 16 medicinal plants enhanced glucose uptake of DXMS-induced insulin resistant HepG2 cells, thereby demonstrating their ability to increase insulin sensitivity, other five medicinal plants including Astragalus membranaceus were found ineffective. The study shows that ancient Chinese medical manuscripts and ethnobotanical surveys on plants for the prevention and treatment of diabetic symptoms provide a promising knowledge base for drug discovery to mitigate the global diabetes epidemic.
RESUMEN
Nine new polyprenylated acylphloroglucinol derivatives, hypercohins B-J (1-9), and nine known analogues were isolated from the aerial parts of Hypericum cohaerens. The structures of 1-9 were elucidated based on spectroscopic analysis, and the absolute configuration of 1 was confirmed by X-ray crystallographic analysis. The inhibitory activities of these isolates on acetylcholinesterase and five human tumor cell lines were tested, and hypercohins B-D (1-3) exhibited moderate inhibitory activity (IC50 5.8-17.9 µM) against the tested tumor cell lines.