Anti-inflammatory Phloroglucinols and Terpenoids from Garcinia subelliptica

Abstract

Three new phloroglucinols, garcinielliptones K (1), L (2), and M (3), and two new terpenoids, garcinielliptones N (4) and O (5), have been isolated from the seeds of Garcinia subelliptica. The structures of 1-5 including their relative configurations were elucidated by spectroscopic methods and supported by computer-generated molecular modeling. Compounds 2 and 3 showed potent inhibitory effects on the release of beta-glucuronidase, and on beta-glucuronidase and histamine, respectively, from peritoneal mast cells stimulated with p-methoxy-N-methylphenethylamine (compound 48/80) in a concentration-dependent manner. Compounds 2 and 3 showed potent effects on NO production in culture media of RAW 264.7 cells in response to lipopolysaccharide (LPS). Compound 2 also showed a potent effect on NO production in culture media of N9 cells in response to LPS/interferon-gamma (IFN-gamma).

Lipoxygenase inhibiting activity of some Malaysian plants

“…Garcinia species have been reported to contain phloroglucinols (garcinielliptones A, B, C, D, F, H, I, K, L & M), terpenoids (garcinielliptone E, G, J, N & O), xanthones (mangostins), and their derivatives, and some have been shown to possess anti-inflammatory effects (Gopalakrishnan et al, 1980;Shankaranarayan et al, 1979;Weng et al, 2003aWeng et al, , 2003bWeng et al, , 2004. The pericarp of G. mangostana containing high levels of xanthones has been shown to be highly effective in scavenging free radicals and suppressing the production of pro-inflammatory cytokines (Chomnawang et al, 2007).…”

An overview on genus garcinia: phytochemical and therapeutical aspects

“…In addition, Garsubellin A exhibited the antiinflammatory property by the inhibition of release of b-glucuronidase and histamine. The compound found to be more potent than the reference standard mepacrine (Weng et al 2003(Weng et al , 2004. These results suggested that phloroglucinols could be very effective in treating inflammation and neurodegenerative diseases.…”

Complete assignment of the 1H and 13C NMR spectra of garciniaphenone and keto‐enol equilibrium statements for prenylated benzophenones

“…[8] There is a great number of researchers dealing with compounds extracted from Garcinia species concerning biological properties, and the anti-inflammatory potentials of such substances are already known, which contribute to the antiphlogistic activity of resins from Garcinia species and explain the rational use of these plants in folk medicine. [9,10] Polyprenylated benzophenones are substances biologically active from Guttiferae family. Some of them were isolated from Symphonia globulifera, Garcinia livingstonei, Garcinia ovalifolia and Clusia rosea as HIV-inhibitory compounds.…”