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Proteasome-inhibitory and cytotoxic constituents of Garcinia lateriflora: absolute configuration of caged xanthones |
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| Authors: | Yulin Ren Esperanza J Carcache de Blanco Leonardus BS Kardono Heebyung Chai Norman R Farnsworth Steven M Swanson Yuanqing Ding Jannie PJ Marais A Douglas Kinghorn |
| Institution: | a Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH 43210, USA b Program for Collaborative Research in the Pharmaceutical Sciences, University of Illinois at Chicago, Chicago, IL 60612, USA c Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, USA d Division of Pharmacy Practice and Administration, College of Pharmacy, The Ohio State University, Columbus, OH 43210, USA e Research Center for Chemistry, Indonesian Institute of Science, Serpong, Tangerang 15310, Indonesia f Herbarium Bogoriense, Research Center for Biology, Indonesian Institute of Science, Bogor 16122, Indonesia g Campus Chemical Instrument Center, The Ohio State University, Columbus, OH 43210, USA h National Center for Natural Products, Research Institute of Pharmaceutical Sciences, School of Pharmacy, The University of Mississippi, University, MS 38677, USA i Department of Pharmacognosy, School of Pharmacy, The University of Mississippi, University, MS 38677, USA |
| Abstract: | A new biflavonoid (1), a new xanthone enantiomer (2), five new caged xanthones (3-7), and several known compounds were isolated from the stem bark of Garcinia lateriflora, collected in Indonesia. The structures of the new compounds were determined by analysis of spectroscopic data, and the absolute configuration of the caged xanthones was shown for the first time at carbons 5, 7, 8, 8a, 10a, and 27, by analysis of COSY and NOESY NMR and ECD spectra. The biflavonoids exhibited proteasome-inhibitory activity, and the known compound, morelloflavone (8) was found to have the greatest potency (IC50=1.3 μM). The caged xanthones were cytotoxic toward HT-29 cells, with the known compound, morellic acid (10) being the most active (ED50=0.36 μM). However, when tested in an in vivo hollow fiber assay, it was inactive at the highest dose tested (20 mg/kg). |
| Keywords: | Garcinia lateriflora Biflavonoids Caged xanthones Proteasome inhibition Cytotoxicity |
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