Honokiol Dimers and Magnolol Derivatives with New Carbon Skeletons from the Roots of Magnolia officinalis and Their Inhibitory Effects on Superoxide Anion Generation and Elastase Release
Two honokiol dimers, houpulins A and B (1 and 2), and two magnolol derivatives, houpulins C and D (3 and 4), were isolated and characterized from an ethanol extract obtained from the roots of Magnolia officinalis. The chemical structures were determined based on spectroscopic and physicochemical analyses, which included 1D and 2D NMR, as well as mass spectrometry data. These four oligomers possess new carbon skeletons postulated to be biosynthesized from the coupling of three or four C6-C3 subunits. In addition, the new oligomers were evaluated for inhibition of superoxide anion generation and elastase release, and houpulin B (2) was identified as a new anti-inflammatory lead compound.
References
[1]
Nakazawa T, Yasuda T, Ohsawa K (2003) Metabolites of orally administered Magnolia officinalis extract in rats and man and its antidepressant-like effects in mice. J Pharm Pharmacol 55: 1583–1591.
[2]
Wang Y, Kong L, Chen Y (2005) Behavioural and biochemical effects of fractions prepared from Banxia Houpu decoction in depression models in mice. Phytother Res 19: 526–529.
[3]
Konoshima T, Kozuka M, Tokuda H, Nishino H, Iwashima A, et al. (1991) Studies on inhibitors of skin tumor promotion, IX. Neolignans from Magnolia officinalis. J Nat Prod 54: 816–822.
[4]
Yahara S, Nishiyori T, Kohda A, Nohara T, Nishioka I (1991) Isolation and characterization of phenolic compounds from Magnoliae cortex produced in China. Chem Pharm Bull 39: 2024–2036.
[5]
Syu WJ, Shen CC, Lu JJ, Lee GH, Sun CM (2004) Antimicrobial and cytotoxic activities of neolignans from Magnolia officinalis. Chem. Biodiversity 1: 530–537.
[6]
Youn UJ, Chen QC, Jin WY, Lee IS, Kim HJ, et al. (2007) Cytotoxic lignans from the stem bark of Magnolia officinalis. J Nat Prod 70: 1687–1689.
[7]
Shen CC, Ni CL, Shen YC, Huang YL, Kuo CH, et al. (2009) Phenolic constituents from the stem bark of Magnolia officinalis. J Nat Prod 72: 168–171.
[8]
Bae EA, Han MJ, Kim NJ, Kim DH (1998) Anti-Helicobacter pylori activity of herbal medicines. Biol Pharm Bull 21: 990–992.
[9]
Hu Y, Qiao J, Zhang X, Ge C (2011) Antimicrobial effect of Magnolia officinalis extract against Staphylococcus aureus. J Sci Food Agric 91: 1050–1056.
[10]
Yang SE, Hsieh MT, Tsai TH, Hsu SL (2003) Effector mechanism of magnolol-induced apoptosis in human lung squamous carcinoma CH27 cells. Br J Pharmacol 138: 193–201.
[11]
Vaid M, D.Sharma S, K.Katiyar S (2010) Honokiol, a phytochemical from the Magnolia plant, inhibits photocarcinogenesis by targeting UVB-induced inflammatory mediators and cell cycle regulators: development of topical formulation. Carcinogenesis 31: 2004–2011.
[12]
Shigemura K, Arbiser JL, Sun SY, Zayzafoon M, Johnstone PA, et al. (2007) Honokiol, a natural plant product, inhibits the bone metastatic growth of human prostate cancer cells. Cancer 109: 1279–1289.
[13]
Chen CR, Tan R, Qu WM, Wu Z, Wang Y, et al. (2011) Magnolol, a major bioactive constituent of the bark of Magnolia officinalis, exerts anti-epileptic effects via GABA/benzodiazepine receptor complex in mice. Br J Pharmacol 164: 1534–1546.
[14]
Ho KY, Tsai CC, Chen CP, Huang JS, Lin CC (2001) Antimicrobial activity of honokiol and magnolol isolated from Magnolia officinalis. Phytother. Res. 15: 139–141.
[15]
Chao LK, Liao PC, Ho CL, Wang EI, Chuang CC, et al. (2010) Anti-inflammatory bioactivities of honokiol through inhibition of protein kinase C, mitogen-activated protein kinase, and the NF-κB pathway to reduce LPS-induced TNFα and NO expression. J Agric Food Chem 58: 3472–3478.
[16]
Munroe ME, Businga TR, Kline JN, Bishop GA (2010) Anti-inflammatory effects of the neurotransmitter agonist honokiol in a mouse model of allergic asthma. J Immunol 185: 5586–5597.
[17]
Kouno I, Hashimoto A, Kawano N, Yang CS (1989) New sesqui-neolignan from the pericarps of Illicium macranthum. Chem Pharm Bull 37: 1291–1292.
[18]
Kouno I, Iwamoto C, Kameda Y, Tanaka T, Yang CS (1994) A new triphenyl-type neolignan and a biphenylneolignan from the bark of Illicium simonsii. Chem Pharm Bull 42: 112–114.
[19]
Sy LK, Brown GD (1998) Biomimetic synthesis of Illicium oligomeric neolignans. J Chem Res. Synopses 8: 476–477.
[20]
Yang Y, Zhang T, Xiao L, Chen RY (2010) Two novel flavanes from the leaves of Morus alba L. J Asian Nat Prod Res. 12: 194–198.
[21]
Antus S, Kurtan T, Juhasz L, Kiss L, Hollosi M, et al. (2001) Chiroptical properties of 2,3-dihydrobenzo[b]furan and chromane chromophores in naturally occurring O-heterocycles. Chirality 13: 493–506.
[22]
Yang ML, Kuo PC, Hwang TL, Chiou WF, Qian K, et al. (2011) Synthesis, in vitro anti-inflammatory and cytotoxic evaluation, and mechanism of action studies of 1-benzoyl-β-carboline and 1-benzoyl-3-carboxy-β-carboline derivatives. Bioorg Med Chem 19: 1674–1682.
[23]
Tintinger GR, Steel HC, Theron AJ, Anderson R (2009) Pharmacological control of neutrophil-mediated inflammation: strategies targeting calcium handling by activated polymorphonuclear leukocytes. Drug Des Devel Ther 2: 95–104.
