Honokiol, Magnolol and Its Monoacetyl Derivative Show Strong Anti-fungal Effect on Fusarium Isolates of Clinical Relevance

Overview

Journal PLoS One

Specialties General Medicine
Science

Date 2019 Sep 5

PMID 31483823

Citations 16

Authors

Safa Oufensou

Barbara Scherm

Giovanna Pani

Virgilio Balmas

Davide Fabbri

Maria Antonietta Dettori

Paola Carta

Ismael Malbran

Quirico Migheli

Giovanna Delogu

Affiliations

Soon will be listed here.

Abstract

The antifungal activity of magnolol and honokiol, two naturally occurring hydroxylated biphenyls, and of their synthetic derivatives was evaluated on a collection of representative isolates of Fusarium oxysporum, F. solani and F. verticillioides of clinical and ecological concern. The tested compounds were proposed as a 'natural' alternative to conventional fungicides, even though a larger range of concentrations (5-400 μg/ml) was applied. The activity of magnolol and honokiol was compared with that of terbinafine (0.1-10 μg/ml), and fluconazole (1-50 μg/ml), two fungicides widely used in treating fungal infections on humans. Magnolol showed similar fungicidal activity compared to fluconazole, whereas honokiol was more effective in inhibiting mycelium growth compared to this fungicide on all tested clinical Fusarium spp. isolates. Compared to terbinafine, honokiol showed similar antifungal activity when tested on clinical F. solani isolates, whereas magnolol was less effective at all selected concentrations (5-400 μg/ml). The different position of the phenol-OH group, as well as its protection, explain different in vitro activities between magnolol, honokiol, and their derivatives. Furthermore, magnolol showed mycelium dry weight reduction at a concentration of 0.5 mM when tested on a set of agricultural isolates of Fusaria, leading to complete inhibition of some of them. Magnolol and honokiol are proposed as efficient and safe candidates for treating clinically relevant Fusaria.

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References

Hajduk P, Bures M, Praestgaard J, Fesik S . Privileged molecules for protein binding identified from NMR-based screening. J Med Chem. 2000; 43(18):3443-7. DOI: 10.1021/jm000164q. View

Denning D . Echinocandins: a new class of antifungal. J Antimicrob Chemother. 2002; 49(6):889-91. DOI: 10.1093/jac/dkf045. View

Amblard F, Govindarajan B, Lefkove B, Rapp K, Detorio M, Arbiser J . Synthesis, cytotoxicity, and antiviral activities of new neolignans related to honokiol and magnolol. Bioorg Med Chem Lett. 2007; 17(16):4428-31. PMC: 2001289. DOI: 10.1016/j.bmcl.2007.06.024. View

Nucci M, Anaissie E . Fusarium infections in immunocompromised patients. Clin Microbiol Rev. 2007; 20(4):695-704. PMC: 2176050. DOI: 10.1128/CMR.00014-07. View

Ahearn D, Zhang S, Stulting R, Schwam B, Simmons R, Ward M . Fusarium keratitis and contact lens wear: facts and speculations. Med Mycol. 2008; 46(5):397-410. DOI: 10.1080/13693780801961352. View

Greenberg M, Dodds M, Tian M . Naturally occurring phenolic antibacterial compounds show effectiveness against oral bacteria by a quantitative structure-activity relationship study. J Agric Food Chem. 2008; 56(23):11151-6. DOI: 10.1021/jf8020859. View

Bueno J, Martinez C, Zapata B, Sanclemente G, Gallego M, Mesa A . In vitro activity of fluconazole, itraconazole, voriconazole and terbinafine against fungi causing onychomycosis. Clin Exp Dermatol. 2009; 35(6):658-63. DOI: 10.1111/j.1365-2230.2009.03698.x. View

Migheli Q, Balmas V, Harak H, Sanna S, Scherm B, Aoki T . Molecular phylogenetic diversity of dermatologic and other human pathogenic fusarial isolates from hospitals in northern and central Italy. J Clin Microbiol. 2010; 48(4):1076-84. PMC: 2849572. DOI: 10.1128/JCM.01765-09. View

Goswami R, Kistler H . Heading for disaster: Fusarium graminearum on cereal crops. Mol Plant Pathol. 2010; 5(6):515-25. DOI: 10.1111/j.1364-3703.2004.00252.x. View

10.

Hoi C, Ho Y, Baum L, Chow A . Neuroprotective effect of honokiol and magnolol, compounds from Magnolia officinalis, on beta-amyloid-induced toxicity in PC12 cells. Phytother Res. 2010; 24(10):1538-42. DOI: 10.1002/ptr.3178. View

11.

Bringmann G, Gulder T, Gulder T, Breuning M . Atroposelective total synthesis of axially chiral biaryl natural products. Chem Rev. 2010; 111(2):563-639. DOI: 10.1021/cr100155e. View

12.

Zabka M, Pavela R, Gabrielova-Slezakova L . Promising antifungal effect of some Euro-Asiatic plants against dangerous pathogenic and toxinogenic fungi. J Sci Food Agric. 2011; 91(3):492-7. DOI: 10.1002/jsfa.4211. View

13.

Lee Y, Lee Y, Lee C, Jung J, Han S, Hong J . Therapeutic applications of compounds in the Magnolia family. Pharmacol Ther. 2011; 130(2):157-76. DOI: 10.1016/j.pharmthera.2011.01.010. View

14.

Gupta A, Paquet M, Simpson F, Tavakkol A . Terbinafine in the treatment of dermatophyte toenail onychomycosis: a meta-analysis of efficacy for continuous and intermittent regimens. J Eur Acad Dermatol Venereol. 2012; 27(3):267-72. DOI: 10.1111/j.1468-3083.2012.04584.x. View

15.

Scherm B, Balmas V, Spanu F, Pani G, Delogu G, Pasquali M . Fusarium culmorum: causal agent of foot and root rot and head blight on wheat. Mol Plant Pathol. 2013; 14(4):323-41. PMC: 6638779. DOI: 10.1111/mpp.12011. View

16.

Guarro J . Fusariosis, a complex infection caused by a high diversity of fungal species refractory to treatment. Eur J Clin Microbiol Infect Dis. 2013; 32(12):1491-500. DOI: 10.1007/s10096-013-1924-7. View

17.

Chen Y, Tsai K, Chan D, Lan K, Chen C, Yang R . Honokiol, a low molecular weight natural product, prevents inflammatory response and cartilage matrix degradation in human osteoarthritis chondrocytes. J Orthop Res. 2013; 32(4):573-80. DOI: 10.1002/jor.22577. View

18.

Pani G, Scherm B, Azara E, Balmas V, Jahanshiri Z, Carta P . Natural and natural-like phenolic inhibitors of type B trichothecene in vitro production by the wheat (Triticum sp.) pathogen Fusarium culmorum. J Agric Food Chem. 2014; 62(22):4969-78. DOI: 10.1021/jf500647h. View

19.

Sun L, Liao K, Wang D . Effects of magnolol and honokiol on adhesion, yeast-hyphal transition, and formation of biofilm by Candida albicans. PLoS One. 2015; 10(2):e0117695. PMC: 4339376. DOI: 10.1371/journal.pone.0117695. View

20.

Zhang Y, Chen T, Yuan P, Tian R, Hu W, Tang Y . Encapsulation of honokiol into self-assembled pectin nanoparticles for drug delivery to HepG2 cells. Carbohydr Polym. 2015; 133:31-8. DOI: 10.1016/j.carbpol.2015.06.102. View