Synthesis and activities of derivatives of magnolol and honokiol

LI Xiaodi; GUO Xinglong; DAI Rongji; LYU Fang; CONG Lin; DENG Yulin

doi:10.11665/j.issn.1000-5048.20170505

Journal of China Pharmaceutical University > 2017 > 48(5): 536-542. > DOI: 10.11665/j.issn.1000-5048.20170505

LI Xiaodi, GUO Xinglong, DAI Rongji, LYU Fang, CONG Lin, DENG Yulin. Synthesis and activities of derivatives of magnolol and honokiol[J]. Journal of China Pharmaceutical University, 2017, 48(5): 536-542. DOI: 10.11665/j.issn.1000-5048.20170505

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Synthesis and activities of derivatives of magnolol and honokiol

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Abstract

Based on the chemical structures of magnolol and honokiol, a series of small molecular derivatives were designed for the treatment of Alzheimer′s disease. Through the Discovery Studio, five compounds( 6a - 6e )exhibited the inhibitory activity against Aβ and Tau proteins in all of the designed compounds. Then the five compounds are chemically synthesized and their biological activities were tested by thioflavin T. The result showed that compound 6a had inhibitory effect on the aggregation of two kinds of target proteins at the concentration of 100 μmol/L, which deserves further research.
- magnolol,
- honokiol,
- derivative,
- Alzheimer′s disease,
- Aβ protein inhibitor,
- synthesis,
- activity

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[1]	Bothwell M,Giniger E.Alzheimer′s disease:neurodevelopment converges with neurodegeneration[J].Cell,2000,102(3):271-273.
[2]	Cummings JL.The Neuropsychiatric inventory:assessing psychopathology in dementia patients[J].Neurology,1997,48(6):10-16.
[3]	Ballard C,Gauthier S,Corbett A,et al.Alzheimer′s disease[J].Lancet,2011,377:1019-1031.
[4]	Torreilles F,Touchon J.Pathogenic theories and intrathecal analysis of sporadic form of Alzheimer′s disease[J].Prog Neuroboil,2002,66(3):191-203.
[5]	Schneider LS,Mangialasche F,Andreasen N,et al.Clinical trials and late-stage drug development for Alzheimer′s disease:an appraisal from 1984 to 2014[J].J Intern Med,2014,275(3):251-283.
[6]	Lin YR,Chen HH,Ko CH,et al.Effects of honokiol and magnolol on acute and inflammatory pain models in mice[J].Life Sci,2007,81(13):1071-1078.
[7]	Munroe ME,Arbiser JL,Bishop GA,et al.Honokiol,a natural plant product,inhibits inflammatory signals and alleviates inflammatory arthritis[J].J Immunol,2007,179(2):753-763.
[8]	Zhou HY,Shin EM,Guo LY,et al.Anti-inflammatory activity of 4-methoxyhonokiol is a function of the inhibition of iNOS and COX-2 expression in RAW 264.7 macrophages via NF-kappaB,JNK and p38MAPK inactivation[J].Eur J Pharmacol,2008,586(1/2/3):340-349.
[9]	Dikalov S,Losik T,Arbiser JL.Honokiol is a potent scavenger of superoxide and peroxyl radicals[J].Biochem Pharmacol,2008,76(5):589-596.
[10]	Park EJ, Min HY, Chung HJ, et al. Down-regulation of c-Src/EGFR-mediated signaling activation is involved in the honokiol-incluced cell cycle arrest and apoptosis in MDA-MB-231 human breast cancer cells[J].Cancer Lett,2009,277(2):133-140.
[11]	Han LL,Xie LP,Li LH,et al.Reactive oxygen species production and Bax/Bcl-2 regulation in honokiol-incluced apoptosis in human hepatocellular carcinoma SMMC-7721 cells[J].Environ Toxicol Pharmacol,2009,281(1):97-103.
[12]	Fried LE,Arbiser JL.Honokiol,a multifunctional antiangiogenic and antitumor agent[J].Antioxid Redox Signal,2009,11(5):1139-1148.
[13]	Harada S,Kishimoto M,Kobayashi M,et al.Honokiol suppresses the development of post-ischemic glucose intolerance and neuronal damage in mice[J].J Nat Med,2012,66(4):591-599.
[14]	Hoi CP,Ho YP,Baum L,et al.Neuroprotective effect of honokiol and magnolol,compounds from Magnolia officinalis,on beta-amyloid-induced toxicity in PC12 cells[J].Phytother Res,2010,24(10):1538-1542.
[15]	Hu Z,Bian X,Liu X,et al.Honokiol protects brain against ischemia-reperfusion injury in rats through disrupting PSD95-nNOS interaction[J].Brain Res,2013,1491:204-212.
[16]	Zhang P,Liu X,Zhu Y,et al.Honokiol inhibits the inflammatory reaction during cerebral ischemia reperfusion by suppressing NF-kappaB activation and cytokine production of glial cells[J].Neurosci Lett,2013,534:123-127.
[17]	Lee YJ, Choi DY, Han SB, et al. Inhibitory effect of ethanol extract of Magnolia officinalis on memory impairment and amyloidogenesis in a transgenic mouse model of Alzheimer′s disease via regulating β-secretase activity[J].Phytother Res,2012,26(12):1884-1892.
[18]	Matsui N,Takahashi K,Takeichi M,et al.Magnolol and honokiol prevent learning and memory impairment and cholinergic deficit in SAMP8 mice[J].Brain Res,2009,1305(11):108-117.
[19]	Fujita S,Taira J.Biphenyl compounds are hydroxyl radical scavengers:their effective inhibition for UV-induced mutation in Salmonella typhimurium TA102[J].Free Radical Bio Med,1994,17(3):273-277.
[20]	Esumia T,Makadoa G,Zhaia H,et al.Efficient synthesis and structure-activity relationship of honokiol,a neurotrophic biphenyl-type neolignan[J].Bioorg Med Chem Lett,2004,14(10):2621-2625.
[21]	Matos K,Soderquist JA.Alkylboranes in the Suzuki-Miyaura coupling:stereohemical and mechanistic[J].J Org Chem,1998,63(3):461-470.

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Synthesis and activities of derivatives of magnolol and honokiol

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