2010216-41-6

Upstream product

• 147782-04-5 garcinol 
• 219538-86-0 guttiferone F 

Relevant academic research and scientific papers

Chemical studies on antioxidant mechanism of garcinol: Analysis of radical reaction products of garcinol and their antitumor activities

Garcinol (1), a polyisoprenylated benzophenone, purified from Garcinia indica fruit rind, displays antioxidant properties and is thought to act as an antioxidant in biological systems. However, the mechanisms of its antioxidant reactions remain unknown. The objective of this study was to characterize the reaction products of garcinol with a stable radical, 2,2-diphenyl-1-picrylhydrazyl (DPPH). Structural elucidation of these products can provide insights into specific mechanisms of antioxidant reactions. Two major reaction products, GDPPH-1 (2) and GDPPH-2 (3), were isolated and identified for the first time. Their structures were determined on the basis of detailed high field 1D and 2D spectral analysis. The identification of these products provides the first unambiguous proof that the principal sites of antioxidant reactions are on the 1,3-diketone and the phenolic ring part of 1. The induction of apoptosis in human leukemia HL-60 cells, the inhibition of NO generation, the effects on the activity of MMP, and the inhibitory effects on H2O2 production of TPA-stimulate HL-60 cells by 1 and its two oxidant products (2 and 3) were investigated and would also be discussed in this paper.

Chemical studies on antioxidant mechanism of garcinol: Analysis of radical reaction products of garcinol with peroxyl radicals and their antitumor activities

Antioxidant actions of garcinol (1), a polyisoprenylated benzophenone, purified from Garcinia indica fruit rind, are believed to contribute to its chemopreventive activity. However, the mechanisms of its antioxidant reactions remain unclear. The objective of this study was to characterize the reaction products of garcinol with peroxyl radicals generated by thermolysis of the azo initiator azo-bis-isobutyrylnitrile (AIBN). Structure elucidation of these products can provide insights into specific mechanisms of antioxidant reactions. Four reaction products (2-5) were isolated and identified. Their structures were determined on the basis of detailed high field 1D and 2D spectral analysis. The identification of these products provides the first unambiguous proof that the double bond of the isopentenyl group is a principal site of the antioxidant reaction of 1. The induction of apoptosis in human leukemia HL-60 cells, the inhibition of NO generation, and the inhibition of LPS-induced iNOS gene expression by Western blot analysis by 1 and its four oxidation products (2-5) were investigated.

Prenylated benzoylphloroglucinols and biphenyl derivatives from the leaves of Garcinia multiflora Champ

Garcimultiflorones H-J (1-3), three new polyprenylated benzoylphloroglucinols, multiflorabiphenyls B-D (4-6), three new biphenyl derivatives, and six known compounds, were isolated from an acetone extract of the leaves of Garcinia multiflora by bioassay-guided fractionation. The structures of the new compounds were elucidated by extensive 1D and 2D NMR spectroscopic analyses and mass spectrometry, and the absolute configurations of compounds 1-3 were determined by the comparison of experimental and calculated electronic circular dichroism (ECD) spectra. All of the isolates were evaluated for cytotoxic activities against several human cancer cell lines. Garcimultiflorone I (2) exhibited significant inhibitory activity against the SGC7901 and HCT116 cell lines, with IC50 values of 4.20 and 5.96 μM, respectively. A cell cycle analysis using flow cytometry showed that the compound arrests the cell cycle at the G1 phase and induces cell death. Moreover, Bcl-2, caspase-3, caspase-9, and PARP western blotting suggested that compound 2 can induce apoptosis. Taken together, these results suggest that compound 2 has anticancer activity that targets the cell cycle through apoptosis signalling pathways.