Physalins with anti-inflammatory activity are present in Physalis alkekengi var. franchetii and can function as Michael reaction acceptors

Hehner, 1999, The anti-inflammatory sesquiterpene lactone parthenolide inhibits NF-κB by targeting the IκB kinase complex, J Immunol, 163, 5617, 10.4049/jimmunol.163.10.5617 Delhase, 1999, Positive and negative regulation of IκB kinase activity through IKKβ subunit phosphorylation, Science, 284, 309, 10.1126/science.284.5412.309 Pasparakis, 2006, Dissection of the NF-kappaB signalling cascade in transgenic and knockout mice, Cell Death Differ, 13, 861, 10.1038/sj.cdd.4401870 Liang, 2006, Inhibition of transcription factor NF-κB signaling proteins IKKβ and p65 through specific cysteine residues by epoxyquinone A monomer: Correlation with its anti-cancer cell growth activity, Biochem Pharmacol, 71, 634, 10.1016/j.bcp.2005.11.013 Srinivasan, 2009, Structure-activity relationship studies of chalcone leading to 3-hydroxy-4, 3′, 4′, 5′- tetramethoxychalcone and its analogues as potent Nuclear Factor κB inhibitors and their anticancer activities, J Med Chem, 52, 7228, 10.1021/jm901278z Kaileh, 2007, Withaferin A strongly elicits I kappa B kinase beta hyperphosphorylation concomitant with potent inhibition of its kinase activity, J Biol Chem, 282, 4253, 10.1074/jbc.M606728200 Harikumar, 2009, Modification of the cysteine residues in IκBα kinase and NF-κB (p65) by xanthohumol leads to suppression of NF-κB-regulated gene products and potentiation of apoptosis in leukemia cells, Blood, 113, 2003, 10.1182/blood-2008-04-151944 Powers, 2002, Irreversible inhibitors of serine, cysteine, and threonine proteases, Chem Rev, 102, 4639, 10.1021/cr010182v Rossi, 2000, Anti-inflammatory cyclopentenone prostaglandins are direct inhibitors of I kappa B kinase, Nature, 403, 103, 10.1038/47520 Kapahi, 2000, Inhibition of NF-kappa B activation by arsenite through reaction with a critical cysteine in the activation loop of I kappa B kinase, J Biol Chem, 275, 36062, 10.1074/jbc.M007204200 Pandey, 2007, Butein, a tetrahydroxychalcone, inhibits nuclear factor (NF)-kappaB and NF-kappaB-regulated gene expression through direct inhibition of I kappa B alpha kinase beta on cysteine 179 residue, J Biol Chem, 282, 17340, 10.1074/jbc.M700890200 Reynaert, 2004, Nitric oxide represses inhibitory kappaB kinase through S-nitrosylation, Proc Natl Acad Sci USA, 101, 8945, 10.1073/pnas.0400588101 Huang, 2011, Synthesis and antiproliferative activity of some steroidal lactams, Steroids, 76, 1346, 10.1016/j.steroids.2011.06.013 Kawai, 1994, Crystal structures of 5α, 6α-epoxy and 2, 3-dihydro derivatives of physalin B, a 13, 14-seco-16, 24-cyclosteroid, and their 1H NMR spectra analysis, Soc Jpn, 67, 222, 10.1246/bcsj.67.222 Guimara˜es ET, Lima MS, Santos LA, Ribeiro IM, Tomassini TB, Soares MB, et al. Activity of physalins purified from Physalis angulata in vitro and in vivo models of cutaneous leishmaniasis. J Antimicrob Chemother 2009; 64: 84–87. Soares, 2003, Inhibition of macrophage activation and lipopolysaccaride-induced death by seco-steroids purified from Physalis angulata L., Eur J Pharmacol, 459, 107, 10.1016/S0014-2999(02)02829-7 Magalhães, 2006, In-vitro and in-vivo antitumour activity of physalins B and D from Physalis angulata, J Pharm Pharmacol, 58, 235, 10.1211/jpp.58.2.0011 Vieira, 2005, Mechanisms of the anti-inflammatory effects of the natural secosteroids physalins in a model of intestinal ischaemia and reperfusion injury, Brit J Pharmacol, 146, 244, 10.1038/sj.bjp.0706321 Ma, 2009, Characterization of tanshinones with quinone reductase induction activity from radix Salvia miltiorrhiza by liquid chromatography/tandem mass spectrometry, Rapid Commun Mass Spectrom, 23, 2857, 10.1002/rcm.4195 Dirsch, 1998, The Griess assay: suitable for a bio-guided fractionation of anti-inflammatory plant extracts?, Plant Medica, 64, 423, 10.1055/s-2006-957473 Mstsuura T, Kawai M, Nakashima R. Bitter principles of Physalis alkekengi var. franchetii: Structure of physalin A. Tetrahedron Lett 1969; 14: 1083–1086. Kawai, 1992, Physalins N and O from Physalis alkekengi, Phytochemistry, 31, 4299, 10.1016/0031-9422(92)80462-N Kawai, 1987, A new physalin from Physalis alkekengi: structure of physalin L., Phytochemistry, 26, 3313, 10.1016/S0031-9422(00)82495-4 Row, 1980, New physalins from Physalis angulata and Physalis lancifolia. Structure and reactions of physalins D, I, G and K, Phytochemistry, 19, 1175, 10.1016/0031-9422(80)83078-0 Böhme, 2010, Thiol reactivity and its impact on the ciliate toxicity of α,β-unsaturated aldehydes, ketones, and esters, Chem Res Toxicol, 23, 1905, 10.1021/tx100226n Straus, 2000, 15-Deoxy-Δ12, 14-prostaglandin J2 inhibits multiple steps in the NF-κB signaling pathway, Proc Natl Acad Sci, 97, 4844, 10.1073/pnas.97.9.4844 Luo, 2007, Sites of alkylation of human Keap1 by natural chemoprevention agents, J Am Soc Mass Spectrom, 18, 2226, 10.1016/j.jasms.2007.09.015