Journal of APPLIED BIOMEDICINE
ISSN 1214-0287 (on-line)
ISSN 1214-021X (printed)

Volume 4 (2006), No 4, p 171-178




Expectations of biologically active compounds of the genus Magnolia in biomedicine

Jiri Patocka, Jiri Jakl, Anna Strunecka

Address: Jiri Patocka, Department of Radiology and Toxicology, Faculty of Health and Social Studies, University of South Bohemia, 370 01 Ceske Budejovice, Czech Republic
prof.patocka@gmail.com

Received 18th July 2006.
Published online 20th October 2006.

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SUMMARY
Magnolia bark is a highly aromatic herbal material obtained from Magnolia officinalis (and other species) of the family Magnoliaceae. In traditional oriental herbal medicine, particularly Chinese medicine, this drug is used for many purposes, especially as a mild tranquillizer. The principal active compounds are the biphenol compounds, magnolol and honokiol, together with other biologically active compounds, which exert numerous and diverse pharmacological actions. Recent research has produced further evidence for the mechanism of their anti-inflammatory, anti-oxidant, antimicrobial, and antitumour activities, and these will be outlined in this review.

KEY WORDS
herbal tranquillizer; honokiol; Magnolia; magnolol; obovatol; pharmacology


REFERENCES
Ai J, Wang X, Nielsen M: Honokiol and magnolol selectively interact with GABA(A) receptor subtypes in vitro. Pharmacology 63:34-41, 2001.

Amblard F, Delinsky D, Arbiser JL, Schinazi RF: Facile purification of honokiol and its antiviral and cytotoxic properties. J Med Chem 49:3426-3427, 2006.

Azuma H, Garcia-Franco JG, Rico-Gray V, Thien LB: Molecular phylogeny of the Magnoliaceae: the biogeography of tropical and temperate disjunctions. Am J Bot 88:2275-2285, 2001.

Bae EA, Han MJ, Kim NJ, Kim DH: Anti-Helicobacter pylori activity of herbal medicines. Biol Pharm Bull 21:990-992, 1998.

Bastidas Ramirez BE, Navarro Ruiz N, Quezada Arellano JD et al.: Anticonvulsant effects of Magnolia grandiflora L. in the rat. J Ethnopharmacol 61:143-152, 1998.

Bateman J, Chapman RD, Simpson D: Possible toxicity of herbal remedies. Scott Med J 43:7-15, 1998.

Cao JX, Lai GF, Wang YF et al.: A new sesquiterpenoid from Magnolia delavayi. Chin Chem Lett 15:791-793, 2004.

Chang B, Lee Y, Ku Y et al.: Antimicrobial activity of magnolol and honokiol against periodontopathic microorganisms. Planta Med 64:367-369, 1998.

Chang CP, Hsu YC, Lin MT: Magnolol protects against cerebral ischemic injury of rat heat stroke. Clin Exp Pharmacol Physiol 30:387-392, 2003.

Chen C, Xu X, Zhu Y et al.: Determination of honokiol and magnolol in cortex Magnoliae officinalis by capillary electrophoresis with electrochemical detection. J Pharm Biomed Anal 41:1479-1484, 2006.

Chen JH, Wu CC, Hsiao G, Yen MH: Magnolol induces apoptosis in vascular smooth muscle. Naunyn Schmiedebergs Arch Pharmacol 368:127-133, 2003.

Clark AM, El-Feraly FS, Li WS: Antimicrobial activity of phenolic constituents of Magnolia grandiflora L. J Pharm Sci 70:951-952, 1981.

Fong WF, Tse AK, Poon KH, Wang C: Magnolol and honokiol enhance HL-60 human leukemia cell differentiation induced by 1,25-dihydroxyvitamin D3 and retinoic acid. Int J Biochem Cell Biol 37:427-441, 2005.

Fukuyama Y, Otoshi Y, Miyoshi K et al.: Neurotrophic sesquiterpene-neolignans from Magnolia obovata - structure and neurotrophic activity. Tetrahedron 48:377-392, 1992.

Hegnauer R: Chemotaxonomie der Pflanzen 9; Birkhauser Verlag, Basel, Boston, Berlin 1990.

Ho KY, Tsai CC, Chen CP et al.: Antimicrobial activity of honokiol and magnolol isolated from Magnolia officinalis. Phytother Res 15:139-141, 2001.

Hong-Yen H, Chau-Shin H: Commonly Used Chinese Herb Formulas with Illustrations. Oriental Healing Arts Institute, Long Beach, CA 1980.

Horigome H, Homma M, Hiran T et al.: Magnolol from Magnolia officinalis inhibits 11 beta-hydroxysteroid dehydrogenase without increases of corticosterone and thymocyte apoptosis in mice. Planta Med 67:33-37, 2001.

Hsu MF, Lu MC, Tsao LT et al.: Mechanisms of the influence of magnolol on eicosanoid metabolism in neutrophils. Biochem Pharmacol 67:831-840, 2004.

Hu S: The Economic botany of Magnoliaceae. In: Liu Y, Fan H, Chen Z et al. (eds). Proceedings of the Internetional Symposium on the Family Magnoliaceae, Science Press, Beijing 2000.

Hunt D: Magnolias and their allies. The International Dendrology Society and the Magnolia Society, Milborne Port 1998.

Hwang EI, Kwon BM, Lee SH et al.: Obovatols, new chitin synthase 2 inhibitors of Saccharomyces cerevisiae from Magnolia obovata. J Antimicrob Chemother 49:95-101, 2002.

Ikeda K, Nagase H: Magnolol has the ability to induce apoptosis in tumor cells. Biol Pharm Bull 25:1546-1549, 2002.

Ikeda K, Sakai Y, Nagase H: Inhibitory effect of magnolol on tumour metastasis in mice. Phytother Res 17:933-937, 2003.

Ito K, Iida T, Ichino K et al. Obovatol and obovatal, novel biphenyl ether lignans from the leaves of Magnolia obovata Thunb Chem Pharm Bull 30:3347-3353, 1982.

IUCN Red List of Threatened Species. IUCN 2004. http://www.iucnredlist.org/

Jinping S: Jingning Magnolia officinalis development project, Jingning Science and Technology Development Department, Zhejiang, China 2000.

Kim S, Mark WC, Parks CR: Phylogentic relationships in family Magnoliaceae inferred from ndhF sequences. Am J Bot 88:717-728, 2001.

Kong ZL, Tzeng SC, Liu YC: Cytotoxic neolignans: an SAR study. Bioorg Med Chem Lett 15:163-166, 2005.

Kwon BM, Kim MK, Lee SH et al.: Acyl-CoA cholesterol acyltransferase inhibitors from Magnolia obovata. Planta Med 63: 550-551, 1997.

Kuribara H, Kishi E, Hattori N et al.: Application of the elevated plus-maze test in mice for evaluation of the content of honokiol in water extracts of magnolia. Phytother Res 13:593-596, 1999.

Lee J, Jung E, Park J et al.: Anti-inflammatory effect of magnolol and honokiol are mediated through inhibition of the downstream pathway of MEKK-1 in NF-kappa B activation signaling. Planta Med 71:338-343, 2005.

Lee MM, Huang HM, Hsieh MT et al.: Antiinflammatory and neuroprotective effects of magnolol in chemical hypoxia in rat cultured cortical cells in hypoglycemic media. Chin J Physiol 43:61-67, 2000.

Li CY, Wang Y, Hu MK: Allylmagnolol, a novel magnolol derivative as potent antioxidant. Bioorg Med Chem 11:3665-3671, 2003.

Li J, Tanaka M, Kurasawa K et al.: Lignan and neolignan derivatives from Magnolia denudata. Chem Pharm Bull (Tokyo) 53:235-237, 2005.

Lin SY, Chang YT, Liu JD et al.: Molecular mechanisms of apoptosis induced by magnolol in colon and liver cancer cells. Mol Carcinog 32:7-83, 2001.

Lin SY, Liu JD, Chang HC et al.: Magnolol suppresses proliferation of cultured human colon and liver cancer cells by inhibiting DNA synthesis and activating apoptosis. J Cell Biochem 84:532-544, 2002.

Lin YR, Chen HH, Ko CH, Chan MH: Neuroprotective activity of honokiol and magnolol in cerebellar granule cell damage. Eur J Pharmacol 537:64-69, 2006.

Liou KT, Shen YC, Chen CF et al.: The antiinflammatory effect of honokiol on neutrophils: mechanisms in the inhibition of reactive oxygen species production. Eur J Pharmacol 475:19-27, 2003.

Liu L, Wu X, Fan X, Hu Z: Separation and determination of honokiol and magnolol in herbal medicines by flow injection-capillary electrophoresis. Anal Bioanal Chem 384:1533-1539, 2006.

Luo XD, Wu SH, Ma YB et al.: Sesquiterpenoids from Magnolia grandiflora. Planta Med 67:354-357, 2001.

Maruyama Y, Kuribara H, Morita M et al.: Identification of magnolol and honokiol as anxiolytic agents in extracts of Saiboku-to, an oriental herbal medicine. J Nat Prod 61:135-138, 1998.

Matsuda H, Kageura T, Oda M et al.: Effects of constituents from the bark of Magnolia obovata on nitric oxide production in lipopolysaccharide-activated macrophages. Chem Pharm Bull (Tokyo) 49:716-720, 2001.

Matsui N, Nakashima H, Ushio Y et al.: Neurotrophic effect of magnolol in the hippocampal CA1 region ofsenescenceaccelerated mice (SAMP1). Biol Pharm Bull 28:1762-1765, 2005.

Park EJ, Zhao YZ, Na M et al.: Protective effects of honokiol and magnolol on tertiary butyl hydroperoxide- or D-galactosamine-induced toxicity in rat primary hepatocytes. Planta Med 69:33-37, 2003.

Park J, Lee J, Jung E et al.: In vitro antibacterial and anti-inflammatory effects of honokiol and magnolol against Propionibacterium sp. Eur J Pharmacol 496:189-195, 2004.

Patocka J, Strunecka A, Jakl J: Magnolia can be not only beatiful, but also helpful. Psychiatrie 6:247-251, 2002.

Pharmacopoeia of the PRC (English edition). People's Medical Publishing House, Beijing 1988.

Shih HC, Wei YH, Lee CH: Magnolol alters the course of endotoxin tolerance and provides early protection against endotoxin challenge following sublethal hemorrhage in rats. Shock 22:358-363, 2004.

Squires RF, Ai J, Witt MR et al.: Honokiol and magnolol increase the number of [3H] muscimol binding sites three-fold in rat forebrain membranes in vitro using a filtration assay, by allosterically increasing the affinities of low-affinity sites. Neurochem Res 24:1593-1602, 1999.

Tachikawa E, Takahashi M, Kashimoto T: Effects of extract and ingredients isolated from Magnolia obovata Thunberg on catecholamine secretion from bovine adrenal chromaffin cells. Biochem Pharmacol 60:433-440, 2000.

Tsai SK, Huang SS, Hong CY: Myocardial protective effect of honokiol: an active component in Magnolia officinalis. Planta Med 62:503-506, 1996.

Tsai SK, Huang CH, Huang SS et al.: Antiarrhythmic effect of magnolol and honokiol during acute phase of coronary occlusion in anesthetized rats: influence of L-NAME and aspirin. Pharmacology 59:227-233, 1999.

Wang JP, Ho TF, Chang LC, Chen CC: Antiinflammatory effect of magnolol, isolated from Magnolia officinalis, on A23187-induced pleurisy in mice. J Pharm Pharmacol 47:857-860, 1995.

Wang JP, Hsu MF, Raung SL et al.: Antiinflammatory and analgesic effects of magnolol. Naunyn Schmiedebergs Arch Pharmacol 346:707-712, 1992.

Watanabe K, Watanabe H, Goto Y et al.: Pharmacological properties of magnolol and honokiol extracted from Magnolia officinalis - central depressant effects. Planta Med 49:103-108, 1983.

Yang MH, Blunden G, Patel AV et al.: Coumarins and sesquiterpene lactones from Magnolia grandiflora leaves. Planta Med 60:390-390, 1994.

Yang SE, Hsieh MT, Tsai TH, Hsu SL: Effector mechanism of magnolol-induced apoptosis in human lung squamous carcinoma CH27 cells. Br J Pharmacol 138:193-201, 2003.

Zhong WB, Wang CY, Ho KJ et al.: Magnolol induces apoptosis in human leukemia cells via cytochrome C release and caspase activation. Anticancer Drugs 14:211-217, 2003.
CITED

DePorter TL, Landsberg GM, Araujo JA, Ethier JL, Bledsoe DL. Harmonease Chewable Tablets reduces noise-induced fear and anxiety in a laboratory canine thunderstorm simulation: A blinded and placebo-controlled study. J Veterinary Behav: Clin Applicat Res. 7: 225-232, 2012.

Alexeev M, Grosenbaugh DK, Mott DD, Fisher JL. The natural products magnolol and honokiol are positive allosteric modulators of both synaptic and extra-synaptic GABA(A) receptors. Neuropharmacol. 62: 2507-2514, 2012.

Stevenson CL. Advances in Peptide Pharmaceuticals. Curr Pharm Biotechnol. 10: 122-137, 2009.

Havel J, Li R, Macka M. CE study of neuroprotective humanin peptide and its derivatives: Interactions with phosphate, sulphate, alkylsulphonates and sulphated-beta-CD. Electrophoresis. 29: 665-671, 2008.

Thompson SM, Sinha S, Topp EM, Camarda KV. A molecular design approach to peptide drug stabilization. Conference Information: Annual Meeting of the American-Institute-for-Chemical-Engineers (AIChE), Oct 30-Nov 04, 2005 Cincinnati, OH. Mol Simul. 32: 291-295, 2006.

Antonyan AA, Sharoyan SG, Harutyunyan AA, Mardanyan SS. Influence of aluminum toxicosis on the activity of adenosine deaminase and dipeptidyl peptidases II and IV. Neurochem J. 3: 118-121, 2009.

Kunesova G, Hlavacek J, Patocka J, Kunesova G, Evangelou A, Zikos C, Benaki D, Paravatou-Petsotas M, Pelecanou M, Livaniou E, Slaninova J. The multiple T-maze in vivo testing of the neuroprotective effect of humanin analogues. Pept. 29: 1982-1987, 2008.

Natarajan S, Shanmugiahthevar KP, Kasi PD. Cholinesterase inhibitors from Sargassum and Gracilaria gracilis: Seaweeds inhabiting South Indian coastal areas (Hare Island, Gulf of Mannar). Nat Prod Res. 23: 355-369, 2009.

Tiwari S, Kolay S, Ghosh KK, Kuca K, Marek J. Kinetic study of the reactions of p-nitrophenyl acetate and p-nitrophenyl benzoate with oximate nucleophiles. Int J Chem Kinet. 41: 57-64, 2009.

Pohanka M, Jun D, Kalasz H, Kuca K. Cholinesterase biosensor construction - A review. Protein Pept Lett. 15: 795-798, 2008.

Kuca K, Stodulka P, Hrabinova M, Hanusova P, Jun D, Dolezal B. Preparation of oxime HI-6 (dichloride and dimethanesulphonate)-antidote against nerve agents. Defence Sci J. 58: 399-404, 2008.

Kuca K, Jun D, Bajgar J. Structural factors influencing potency of currently used acetylc holineste rase reactivators for treatment of cyclosarin intoxications. Curr Pharm Des. 13: 3445-3452, 2007.

Musilek K, Holas O, Kuca K, Jun D, Dohnal V, Dolezal M. Synthesis of a novel series of non-symmetrical bispyridinium compounds bearing a xylene linker and evaluation of their reactivation activity against tabun and paraoxon-inhibited acetylcholinesterase. J Enzyme Inhib Med Chem. 22: 425-432, 2007.

Kassa J, Karasova J. The evaluation of the neuroprotective effects of bispyridinium oximes in Tabun-poisoned rats. J Toxicol Environ Health Part A. 70: 1556-1567, 2007.

Kuca K, Racakova V, Jun D. Structure-activity relationships for in vitro oxime reactivation of chlorpyrifos-inhibited acetylcholinesterase. Chem Papers. 61: 256-261, 2007.

Wang J, Gu JD, Leszczynski J, Feliks M, Sokalski WA. Oxime-induced reactivation of sarin-inhibited AChE: A theoretical mechanisms study. J Phys Chem B. 111: 2404-2408, 2007.

Bajgar J, Fusek J, Bartosova L, Jun D, Kuca K. Evaluation of reactivation test in anaesthetized dogs with experimental intoxication with nerve agents. J Appl Toxicol. 26: 439-443, 2006.

Skwarzec B, Kabat K, Astel A. Seasonal and spatial variability of Po-210, U-238 and Pu239+240 levels in the river catchment area assessed by application of neural-network based classification. J Environ Radioact. 100: 167-175, 2009.

Tutu H, Cukrowska EM, Dohnal V, Havel J. Application of artificial neural networks for classification of uranium distribution in the Central Rand goldfield, South Africa. Environ Model Assess. 10: 143-152, 2005.

Nunez MC, Garcia-Rubino ME, Conejo-Garcia A, Cruz-Lopez O, Kimatrai M, Gallo MA, Espinosa A, Campos JM. Homochiral drugs: a demanding tendency of the pharmaceutical industry. Curr Medic Chem. 16: 2064-2074, 2009.

Kovalenko LP, Shipaeva EV, Balakshin VV, Presnova GA, Chistyakov AN, Klodt PM, Kudrin VS, Durnev AD. Antiallergenic activity of birch bark dry extract with at least 70% betulin content. Pharm Chem J. 43: 110-114, 2009.

Szakiel A, Mroczek A. Distribution of triterpene acids and their derivatives in organs of cowberry (Vaccinium vitis-idaea L.) plant. Acta Biochim Pol. 54: 733-740, 2007.

Saha MR, Alam MA, Akter R, Jahangir R. In vitro free radical scavenging activity of Ixora coccinea L. Bangladesh J Pharmacol. 3: 90-96, 2008.

Gauthier C, Legault J, Piochon M, Lavoie S, Tremblay S, Pichette A. Synthesis, cytotoxicity, and haemolytic activity of chacotrioside lupane-type neosaponins and their germanicane-type rearrangement products. Bioorg Med Chem Lett. 19: 2310-2314, 2009.

Rhourri-Frih B, Chaimbault P, Claude B, Lamy C, Andre P, Lafosse M. Analysis of pentacyclic triterpenes by LC-MS. A comparative study between APCI and APPI. J Mass Spectrom. 44: 71-80, 2009.

Dehelean CA, Soica C, Peev C, Gruia AT, Seclaman E. Physico-chemical and molecular analysis of antitumoral pentacyclic triterpenes in complexation with gamma-cyclodextrin. Rev Chim. 59: 887-890, 2008.

Soica C, Dehelean CA, Ordodi V, Antal D, Vlaia V. Complexation with hydroxypropyl-gamma-cyclodextrin of birch tree extract - Physico-chemical characterisation of their binary products. Rev Chim. 59: 678-681, 2008.

da Costa HNR, dos Santos MC, Alcantara AFD, Silva MC, Franca R, Pilo-Veloso D. Chemical constituents and antiedematogenic activity of Peltodon radicans (Lamiaceae). Quim Nova. 31: 744-750, 2008.

de Souza MT, Buzzi FDC, Filho VC, Hess S, Delle Monache F, Niero R. Phytochemical and Antinociceptive properties of Matayba elaeagnoides Radlk. Barks. Zeitschrift Naturforschung C-A J Biosci. 62: 550-554, 2007.

Paduch R, Kandefer-Szerszen M, Trytek M, Fiedurek J. Terpenes: substances useful in human healthcare. Arch Immunol Ther Exp. 55: 315-327, 2007.

Pandey R, Verma RK, Gupta MM. High-performance thin-layer chromatographic method for quantitative determination of 4 alpha-methyl-24 beta-ethyl-5 alpha-cholesta-14,25-dien-3 beta-ol, 24 beta-ethylcholesta-5,9(11),22E-trien-3 beta-ol, and betulinic acid in Clerodendrum inerme. J Separation Sci. 30: 2086-2091, 2007.

Lucquin A, March RJ, Cassen S: Analysis of adhering organic residues of two "coupes-a-socles" from the Neolithic funerary site "La Hougue Bie" in Jersey: evidences of birch bark tar utilisation. J Archeolog Sci. 34: 704-710, 2007.

Toker Z. Variation of total hypericin, phenolic and flavonoid compounds in Hypericum triquetrifolium during its phenological cycle. Pharm Biol. 47: 285-288, 2009.

Mccue PP, Phang JM. Identification of Human Intracellular Targets of the Medicinal Herb St. John's Wort by Chemical-Genetic Profiling in Yeast. J Agric Food Chem. 56: 11011-11017, 2008.

Odabas MS, Radusiene J, Cirak C, Camas N. Prediction models for the phenolic contents in some Hypericum species from Turkey. Asian J Chem. 20: 4792-4802, 2008.

Kacar O, Goksu E, Azkan N. Effects of morphogenetic and diurnal variability on the hypericin content in St. John's Wort (Hypericum perforatum L.). African J Biotechnol. 7: 2163-2168, 2008.

Cirak C, Radusiene J, Camas N. Pseudohypericin and hyperforin in two Turkish Hypericum species: Variation among plant parts and phenological stages. Biochem Syst Ecol. 36: 377-382, 2008.

Ayan AK, Cirak C. Hypericin and pseudohypericin contents in some Hypericum species growing in Turkey. Pharm Biol. 46: 288-291, 2008.

Cirak C, Radusiene J, Arslan B. Variation of bioactive substances in Hypericum montbretii during plant growth. Nat Prod Res. 22: 246-252, 2008.

Cirak C, Radusiene J, Janullis V, Lvanauskas L, Arslan B. Chemical constituents of some Hypericum species growing in Turkey. J Plant Biol. 50: 632-635, 2007.

Cirak C, Radusiene J. Variation of hyperforin in Hypericum monthretii during its phenological cycle. Nat Prod Res. 21: 1151-1156, 2007.

Jung HJ, Park K, Lee IS, Kim HS, Yeo SH, Woo ER, Lee DG. S-Phase accumulation of Candida albicans by anticandidal effect of amentoflavone isolated from Selaginella tamariscina. Biol Pharm Bull. 30: 1969-1971, 2007.

Patocka J, Hon Z, Streda L, Kuca K, Jun D. Biohazards of protein biotoxins. Defence Sci J. 57: 825-837, 2007.

Lopes-Lutz D, Mckay T, Kolodziejczyk PP. Distribution of volatiles in Artemisia cana. Pharm Biol. 46: 373-376, 2008.

Blagojevic P, Radulovic N, Palic R, Stojanovic G. Chemical composition of the essential oils of Serbian wild-growing Artemisia absinthium and Artemisia vulgaris. J Agric Food Chem. 54: 4780-4789, 2006.

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