N-alkylamides from Litsea cubeba (Lour.) Pers. with potential anti-inflammatory activity

References

• Bruno F, Errico S, Pace S, Nawrozkij MB, Mkrtchyan AS, Guida F, Maisto R, Olgaç A, D'Amico M, Maione S, et al. 2018. Structural insight into the optimization of ethyl 5-hydroxybenzo[g]indol-3-carboxylates and their bioisosteric analogues as 5-LO/m-PGES-1 dual inhibitors able to suppress inflammation. Eur J Med Chem. 155:946–960. doi: 10.1016/j.ejmech.2018.05.041.
   PubMed Web of Science ®Google Scholar
• Chen CY, Chang FR, Yen HF, Wu YC. 1998. Amides from stems of Annona cherimola. Phytochemistry. 49(5):1443–1447. doi: 10.1016/S0031-9422(98)00123-X.
   Web of Science ®Google Scholar
• Chen H, Li YJ, Sun YJ, Gong JH, Du K, Zhang YL, Su CF, Han Q, Zheng XK, Feng WS. 2017. Lignanamides with potent antihyperlipidemic activities from the root bark of Lycium chinense. Fitoterapia. 122:119–125. doi: 10.1016/j.fitote.2017.09.004.
   PubMed Web of Science ®Google Scholar
• Dar KB, Bhat AH, Amin S, Masood A, Zargar MA, Ganie SA. 2016. Inflammation: a multidimensional insight on natural anti-inflammatory therapeutic compounds. Curr Med Chem. 23(33):3775–3800.
   PubMed Web of Science ®Google Scholar
• Dinh CP, Ville A, Neukirch K, Viault G, Temml V, Koeberle A, Werz O, Schuster D, Stuppner H, Richomme P, et al. 2020. Structure-based design, semi-synthesis and anti-inflammatory activity of tocotrienolic amides as 5-lipoxygenase inhibitors. Eur J Med Chem. 202:112518. doi: 10.1016/j.ejmech.2020.112518.
   PubMed Web of Science ®Google Scholar
• Du X, Li Y, Xia YL, Ai SM, Liang J, Sang P, Ji XL, Liu SQ. 2016. Insights into protein-ligand interactions: mechanisms, models, and methods. IJMS. 17(2):144. doi: 10.3390/ijms17020144.
   Google Scholar
• Elufioye TO, Habtemariam S, Adejare A. 2020. Chemistry and pharmacology of alkylamides from natural origin. Rev Bras Farmacogn. 30(5):622–640. doi: 10.1007/s43450-020-00095-5.
   PubMedGoogle Scholar
• Franke L, Schwarz O, Müller-Kuhrt L, Hoernig C, Fischer L, George S, Tanrikulu Y, Schneider P, Werz O, Steinhilber D, et al. 2007. Identification of natural-product-derived inhibitors of 5-Lipoxygenase activity by ligand-based virtual screening. J Med Chem. 50(11):2640–2646. doi: 10.1021/jm060655w.
   PubMed Web of Science ®Google Scholar
• Gilbert NC, Bartlett SG, Waight MT, Neau DB, Boeglin WE, Brash AR, Newcomer ME. 2011. The structure of human 5-lipoxygenase. Science. 331(6014):217–219. doi: 10.1126/science.1197203.
   PubMed Web of Science ®Google Scholar
• Gilbert NC, Rui Z, Neau DB, Waight MT, Bartlett SG, Boeglin WE, Brash AR, Newcomer ME. 2012. Conversion of human 5-lipoxygenase to a 15-lipoxygenase by a point mutation to mimic phosphorylation at Serine–663. Faseb J. 26(8):3222–3229. doi: 10.1096/fj.12-205286.
   PubMed Web of Science ®Google Scholar
• Grimm EL, Brideau C, Chauret N, Chan CC, Delorme D, Ducharme Y, Ethier D, Falgueyret JP, Friesen RW, Guay J, et al. 2006. Substituted coumarins as potent 5-lipoxygenase inhibitors. Bioorg Med Chem Lett. 16(9):2528–2531. doi: 10.1016/j.bmcl.2006.01.085.
   PubMed Web of Science ®Google Scholar
• Guo Q, Zeng KW, Gao XL, Zhu ZX, Zhang SY, Chai XY, Tu PF. 2015. Chemical constituents with NO production inhibitory and cytotoxic activities from Litsea cubeba. J Nat Med. 69(1):94–99. doi: 10.1007/s11418-014-0872-6.
   PubMed Web of Science ®Google Scholar
• Hieke M, Greiner C, Thieme TM, Schubert-Zsilavecz M, Werz O, Zettl H. 2011. A novel class of dual mPGES-1/5-LO inhibitors based on the α-naphthyl pirinixic acid scaffold. Bioorg Med Chem Lett. 21(5):1329–1333. doi: 10.1016/j.bmcl.2011.01.049.
   PubMed Web of Science ®Google Scholar
• Hsu KC, HuangFu WC, Lin TE, Chao MW, Sung TY, Chen YY, Pan SL, Lee JC, Tzou SC, Sun CM, et al. 2020. A site-moiety map and virtual screening approach for discovery of novel 5-LOX inhibitors. Sci Rep. 10(1):10510. doi: 10.1038/s41598-020-67420-9.
   PubMed Web of Science ®Google Scholar
• Huang FC, Shoupe TS, Lin CJ, Lee TDY, Chan WK, Tan J, Schnapper M, Suh JT, Gordon RJ, Sonnino PA, et al. 1989. Differential effects of a series of hydroxamic acid derivatives on 5-lipoxygenase and cyclooxygenase from neutrophils and 12-lipoxygenase from platelets and their in vivo effects on inflammation and anaphylaxis. J Med Chem. 32(8):1836–1842. doi: 10.1021/jm00128a027.
   PubMed Web of Science ®Google Scholar
• Jiang M, Zhang W, Yang X, Xiu F, Xu H, Ying X, Stien D. 2018. An isoindole alkaloid from Portulaca oleracea L. Nat Prod Res. 32(20):2431–2436. doi: 10.1080/14786419.2017.1419226.
   PubMed Web of Science ®Google Scholar
• Koeberle A, Muñoz E, Appendino GB, Minassi A, Pace S, Rossi A, Weinigel C, Barz D, Sautebin L, Caprioglio D, et al. 2014. SAR Studies on Curcumin’s pro-inflammatory targets: discovery of prenylated pyrazolocurcuminoids as potent and selective novel inhibitors of 5-lipoxygenase. J Med Chem. 57(13):5638–5648. doi: 10.1021/jm500308c.
   PubMed Web of Science ®Google Scholar
• Koeberle A, Werz O. 2014. Multi-target approach for natural products in inflammation. Drug Discov Today. 19(12):1871–1882. doi: 10.1016/j.drudis.2014.08.006.
   PubMed Web of Science ®Google Scholar
• Kolasa T, Gunn DE, Bhatia P, Woods KW, Gane T, Stewart AO, Bouska JB, Harris RR, Hulkower KI, Malo PE, et al. 2000. Heteroarylmethoxyphenylalkoxyiminoalkylcarboxylicacids as leukotriene biosynthesis inhibitors. J Med Chem. 43(4):690–705. doi: 10.1021/jm9904102.
   PubMed Web of Science ®Google Scholar
• Kong DG. 2015. Research on chemical constituents of Litsea glutinosa and Litsea garrettii. [master’s thesis]. Jinan: Shandong University of Traditional Chinese Medicine.
   Google Scholar
• Liao PC, Yang TS, Chou JC, Chen J, Lee SC, Kuo YH, Ho CL, Chao LKP. 2015. Anti-inflammatory activity of neral and geranial isolated from fruits of Litsea cubeba Lour. J Funct Foods. 19:248–258. doi: 10.1016/j.jff.2015.09.034.
   Web of Science ®Google Scholar
• Lin B, Sun LN, Xin HL, Nian H, Song HT, Jiang YP, Wei ZQ, Qin LP, Han T. 2016. Anti-inflammatory constituents from the root of Litsea cubeba in LPS-induced RAW 264.7 macrophages. Pharm Biol. 54(9):1741–1747. doi: 10.3109/13880209.2015.1126619.
   PubMed Web of Science ®Google Scholar
• Medzhitov R. 2008. Origin and physiological roles of inflammation. Nature. 454(7203):428–435. doi: 10.1038/nature07201.
   PubMed Web of Science ®Google Scholar
• Meirer K, Rödl CB, Wisniewska JM, George S, Häfner AK, Buscató EL, Klingler FM, Hahn S, Berressem D, Wittmann SK, et al. 2013. Synthesis and structure–activity relationship studies of novel dual inhibitors of soluble epoxide hydrolase and 5-lipoxygenase. J Med Chem. 56(4):1777–1781. doi: 10.1021/jm301617j.
   PubMed Web of Science ®Google Scholar
• Morphy R, Rankovic Z. 2005. Designed multiple ligands. An emerging drug discovery paradigm. J Med Chem. 48(21):6523–6543. doi: 10.1021/jm058225d.
   PubMed Web of Science ®Google Scholar
• Moser D, Wisniewska JM, Hahn S, Achenbach J, Buscató E, Klingler FM, Hofmann B, Steinhilber D, Proschak E. 2012. Dual-target virtual screening by pharmacophore elucidation and molecular shape filtering. ACS Med Chem Lett. 3(2):155–158. doi: 10.1021/ml200286e.
   PubMed Web of Science ®Google Scholar
• Pan PC, Cheng MJ, Peng CF, Huang HY, Chen JJ, Chen IS. 2010. Secondary metabolites from the roots of Litsea hypophaea and their antitubercular activity. J Nat Prod. 73(5):890–896. doi: 10.1021/np100022s.
   PubMed Web of Science ®Google Scholar
• Patil KR, Mahajan UB, Unger BS, Goyal SN, Belemkar S, Surana SJ, Ojha S, Patil CR. 2019. Animal models of inflammation for screening of anti-inflammatory drugs: implications for the discovery and development of phytopharmaceuticals. IJMS. 20(18):4367. doi: 10.3390/ijms20184367.
   Google Scholar
• Prasher P, Singh, P, Pooja. 2014. Lead modification: amino acid appended indoles as highly effective 5-LOX inhibitors. Bioorg Med Chem. 22(5):1642–1648., doi: 10.1016/j.bmc.2014.01.027.
   PubMed Web of Science ®Google Scholar
• Qu YH. 2015. Study on the Chemical Constituents of Litsea cubeba. [master’s thesis]. Heilongjiang University of Chinese Medicine: Haerbin.
   Google Scholar
• Ratnasooriya WD, Pieris KPP. 2005. Attenuation of persistent pain and hyperalgesia by Spilanthes acmella. flowers in rats. Pharm Biol. 43(7):614–619. doi: 10.1080/13880200500301944.
   Web of Science ®Google Scholar
• Ren HC, Tan RD, Zhang QY, Chen W, Liang H. 2012. Chemical constituents of Pilea cavaleriei subsp. cavaleriei. Chin J Chin Mater Med. 37(17):2581–2584.
   Google Scholar
• Ribeiro D, Freitas M, Tomé SM, Silva AMS, Porto G, Cabrita EJ, Marques MMB, Fernandes E. 2014. Inhibition of LOX by flavonoids: a structure–activity relationship study. Eur J Med Chem. 72:137–145. doi: 10.1016/j.ejmech.2013.11.030.
   PubMed Web of Science ®Google Scholar
• Satoh Y, Stanton JL, Hutchison AJ, Libby AH, Kowalski TJ, Lee WH, White DH, Kimble EF. 1993. Substituted chromenes as potent, orally active 5-lipoxygenase inhibitors. J Med Chem. 36(23):3580–3594. doi: 10.1021/jm00075a013.
   PubMed Web of Science ®Google Scholar
• Sinha S, Manju SL, Doble M. 2019. Chalcone-thiazole hybrids: rational design, synthesis, and lead identification against 5-lipoxygenase. ACS Med Chem Lett. 10(10):1415–1422. doi: 10.1021/acsmedchemlett.9b00193.
   PubMed Web of Science ®Google Scholar
• Sun J, Gu YF, Su XQ, Li MM, Huo HX, Zhang J, Zeng KW, Zhang Q, Zhao YF, Li J, et al. 2014. Anti-inflammatory lignanamides from the roots of Solanum melongena L. Fitoterapia 98:110–116. doi: 10.1016/j.fitote.2014.07.012.
   PubMed Web of Science ®Google Scholar
• Tan CM, Chen GS, Chen CS, Chang PT, Chern GW. 2011. Design, synthesis and biological evaluation of benzo[1.3.2]dithiazolium ylide 1,1-dioxide derivatives as potential dual cyclooxygenase-2/5-lipoxygenase inhibitors. Bioorg Med Chem. 19(21):6316–6328. doi: 10.1016/j.bmc.2011.09.003.
   PubMed Web of Science ®Google Scholar
• Thangapandian S, John S, Sakkiah S, Lee KW. 2011. Pharmacophore-based virtual screening and Bayesian model for the identification of potential human leukotriene A4 hydrolase inhibitors. Eur J Med Chem. 46(5):1593–1603. doi: 10.1016/j.ejmech.2011.02.007.
   PubMed Web of Science ®Google Scholar
• Vieider L, Romp E, Temml V, Fischer J, Kretzer C, Schoenthaler M, Taha A, Hernández-Olmos V, Sturm S, Schuster D, et al. 2019. Synthesis, biological evaluation and structure–activity relationships of diflapolin analogues as dual sEH/FLAP inhibitors. ACS Med Chem Lett. 10(1):62–66. doi: 10.1021/acsmedchemlett.8b00415.
   PubMed Web of Science ®Google Scholar
• Wang YH, Shi M, Niu HM, Yang J, Xia MY, Luo JF, Chen YJ, Zhou YP, Li H. 2018. Substituting one Paris for another? In vitro cytotoxic and in vivo antitumor activities of Paris forrestii, a substitute of Paris polyphylla var. yunnanensis. J Ethnopharmacol. 218:45–50. doi: 10.1016/j.jep.2018.02.022.
   PubMed Web of Science ®Google Scholar
• Wang YS, Wen ZQ, Li BT, Zhang HB, Yang JH. 2016. Ethnobotany, phytochemistry, and pharmacology of the genus Litsea: an update. J Ethnopharmacol. 181:66–107. doi: 10.1016/j.jep.2016.01.032.
   PubMed Web of Science ®Google Scholar
• Wu ZY. 1982. Delectis Florae Republicae Popularis Sinicae Academiae Sinicae Edita. Flora Reipublicae Popularis Sinicae. Science Press, Beijing. 32: p. 261. [Chinese]
   Google Scholar
• Xia H, Xia GY, Wang LY, Wang M, Wang YN, Lin PC, Lin S. 2021. Bioactive sesquineolignans from the twigs of Litsea cubeba. Chin. J. Nat. Med. 19(10):796–800.
   PubMed Web of Science ®Google Scholar
• Xia-Hou ZR, Feng XF, Mei YF, Zhang YY, Yang T, Pan J, Yang JH, Wang YS. 2022. 5-Demethoxy-10-ethoxyexotimarin F, a new coumarin with MAO-B inhibitory potential from Murraya exotica L. Molecules. 27(15):4950. doi: 10.3390/molecules27154950.
   PubMed Web of Science ®Google Scholar
• Zhu CL, Yang PM. 2007. Isolation and structure identification of Litsea cubeba. Chin J Pharm. 38(8):558–560.
   Google Scholar