Effects of Magnolol, Honokiol, Obovatol, 4-O-methylhonokiol against

bacteria.
2018-04-01, Cu Trung Dang, Biotech Lab, YU

Purpose:
Based on data from previous studies to figure out the appropriate inhibition
concentration of compounds for the antibiofilm activities test with A. baumannii
without cell growth.
Conclusions:
Magnolol, Honokiol, Obovatol, 4-O-methylhonokiol are isolated from the genus
Magnolia (Table 1). These natural product compounds significantly effect on
antifungal, antimicrobial, antibacterial, antibiofilm activity.
Table 1 : Information of compounds
Structure
Information
IUPAC name: 4-Allyl-2-(5-allyl-2-hydroxy-phenyl)phenol
Formula: C18H18O2
MW: 266.34
Source : Isolated from the genus Magnolia.
Solubility: Soluble in DMSO, 100% ethanol or methanol.
Long term Storage: -20°C
Handling: Protect from light
Magnolol
IUPAC name: 2-(4-hydroxy-3-prop-2-enyl-phenyl)- 4-prop-
2-enyl-phenol
Formula: C18H18O2
MW: 266.3
Source : Isolated from the genus Magnolia
Solubility: Soluble in DMSO, 100% ethanol or methanol
Longterm Storage: -20°C
Handling: Protect from light
Honokiol
IUPAC name: 5-Prop-2-enyl-3-(4-prop-2-
enylphenoxy)benzene-1,2-diol
Formula: C18H18O3
MW: 282.3
Source : Isolated from the genus Magnolia
Solubility: Soluble in DMSO, 100% ethanol or methanol
Longterm Storage: -20°C
Handling: Protect from light
Obovatol
IUPAC name: 2-(4-Methoxy-3-prop-2-enylphenyl)-4-prop-
2-enylphenol.
Formula: C19H20O2
MW: 280.3
Source : Isolated from the genus Magnolia
Solubility: Soluble in DMSO, 100% ethanol or methanol
Longterm Storage: -20°C
4-O-methylhonokiol
Handling: Protect from light
 The phenolic compounds were reported to exhibit potent antibacterial activities
against Gram-positive bacteria, Streptococcus mutans,[19,20,21,22] and periodontopathic
microorganism such as Polyphyromonas gingivalis, Prevotella intermedia,
Actinobacillus actinomycetemcomitans, Capnocytophaga gingivalis, and Veillonella
disper [18]. Magnolol, honokiol, obovatol, 4-O-methylhonokiol have a variety of
pharmacological activities, including antiinflammatory effects[23,25], antimicrobial
activity[14,24]. In addition, magnolol and honokiol have been known to show high
antimicrobial activity against several microorganisms[1,2,18,24]. Magnolol was reported
to exhibit potent antibacterial activity against several microorganisms, including
methicillin-resistant S. aureus, vancomycin-resistant enterococci and Candida
albicans[3,24]. Previous report also showed that magnolol inhibited biofilm formation by
several bacteria, such as Streptococcus mutans, Streptococcus sanguis, Actinomyces
naeslundii, Actinomyces viscosus, Enterococcus faecalis, and Fusobacterium
nucleatum[16,17].
Based on previous studies, effects of compounds on batceria strains are listed in
Table 2.

Table 2: MIC/EC and MBC/MFC of compounds.

MIC: Minimum inhibition concentration.

EC: Experiment concentration .
MBC/MFC: Minimum bactericidal/Fungicidal concentration.
Activities Agents Strains MIC MBC/MFC Refer
µg/ml µg/ml ence
Magnolol T. mentarophytes KTTC 6077 50 [1]
M. gypseum KCTC 1252 50
E. Floccosum KCTC 1246 25
C. neoforman KCTC 7224 >200
A. nigger KCTC 1700 100
C. albicans KCTC 1940 25
T. mentarophytes KTTC 6077 25
Honokiol M. gypseum KCTC 1252 25
E. Floccosum KCTC 1246 25
Antifungal
C. neoforman KCTC 7224 50
A. nigger KCTC 1700 50
C. albicans KCTC 1940 25
C albicans YL 313 64 [6]
C albicans YL 317 64
C albicans YL 318 64
C albicans YL 319 128
C albicans YL 325 128
C albicans YL 328 64
 C albicans YL 331 128
C albicans YL 336 128
C albicans YL 338 64
C albicans YL 339 64
C albicans YL 342 128
C albicans YL 345 128
C albicans YL 346 128
C albicans YL 349 64
C albicans YL 351 128
C albicans YL 353 64
C albicans YL 358 64
C albicans YL 360 64
C albicans YL 363 128
C albicans YL 366 64
C albicans YL 370 128
C albicans YL 371 64
C albicans TW 00313 64
C albicans TW 07239 64
Magnolol B. bronchiseptica ATCC 4617 25 [2]
S. typhi ATCC 6539 >100
B. subtilis ATCC 6633 25
S. marcescens ATCC 8100 25
M. llluteus ATCC 9341 25
K. pneumoniae ATCC 10031 25
M. flavus ATCC 10240 25
B. cereus ATCC 11778 25
S. flexneii ATCC 12022 >100
S. epidermidis ATCC 12228 >100
E. aerogenes ATCC 13048 >100
P. vulgaris ATCC 13315 100
P. intermedia ATCC 25611 25
E. coli ATCC 25922 >100
S. aureus ATCC 25923 38
Antimicrobial
P. aeruginosa ATCC 27853 >100
A. actinomycetemcomitance ATCC 25
29523
P. gingivalis ATCC 33277 25
B. bronchiseptica ATCC 4617 50
Honokiol S. typhi ATCC 6539 100
B. subtilis ATCC 6633 25
S. marcescens ATCC 8100 100
M. llluteus ATCC 9341 25
K. pneumoniae ATCC 10031 100
M. flavus ATCC 10240 25
B. cereus ATCC 11778 25
S. flexneii ATCC 12022 >100
 S. epidermidis ATCC 12228 >100
E. aerogenes ATCC 13048 >100
P. vulgaris ATCC 13315 >100
P. intermedia ATCC 25611 25
E. coli ATCC 25922 >100
S. aureus ATCC 25923 50
P. aeruginosa ATCC 27853 >100
A. actinomycetemcomitance ATCC 25
29523
P. gingivalis ATCC 33277 25
S. aureus ATCC 6538P 13.31 26.63 [5]
B. subtilius ATCC 6633 8.26 16.78
P. acnes ATCC 6919 4.13 16.78
P. granulosum ATCC 25564 8.26 16.78
E. coli 8739
P. aeruginosa ATCC 27853
C. anbicans ATCC10231 26.63 53.27
F. neoformans ATCC 34144 6.66 13.32
A. niger ATCC 10254 53.27 106.54
T. mentagrophytes KCTC 6077 13.32 13.32
Magnolol P. acnes ATCC 6919 9 [3]
P. granulosum ATCC 25564 9
Honokiol P. acnes ATCC 6919 4
P. granulosum ATCC 25564 3
Compound A. baumannii N/A [10]
: Magnolol,
Antibacterial Honokiol
Obovatol E. coli ATCC 25922 >512 [14]
P. aeruginosa ATCC 14028 >512
S. typhimurium ATCC 278553 >512
S. typhimurium SL 1344 >512
S. aureus ATCC 6538p 32
Magnolol C. albicans SC5314 8-64 [9]
S. mutans MT 8148 5-20 [12]
C. albicans ATCC 90028 160 [15]
C. krusei ATCC 6258 80
Antibiofilm
C. dubliniensis MYA 646 20
C. glabrata ATCC 90030 40

Honokiol C. albicans SC5314 8-64 [9]

S. mutans MT 8148 5-20 [12]
Reference
1. Bang, K. H. et al. Antifungal activity of magnolol and honokiol. Arch Pharm
Res Vol 23, No 1, 46-49, 2000.
2. Ho, K. Y. et al. Antimicrobial activity of honokiol and magnolol isolated from
Magnolia officinalis. Phytother. Res. 15, 139-141, 2001.
3. Park, J. et al. In vitro antibacterial and anti-inflammatory effects of honokiol
and magnolol against Propionbacyerium sp. European Journal of
Phamacology 496, 189-195, 2004.
4. Syu, W. J. et al. Antimicrobial and cytotoxic activities of neolignans from
Magnolia officinalis. Chemistry & Biodiversity, Vol. 1, 530-537, 2004.
5. Kim, Y. S. et al. Synthesis and microbiological evaluation of honokiol
derivatives as new antimicrobial agents. Arch Pharm Res Vol 33, No 1, 61-65,
2010.
6. Jin, J., Guo, N., Zhang, J. et al. The synery of honokiol an fluconazole against
clinical isolates of azole-resistant Candida albicans. Letters in Applied
Microbiology 51, 351-357, 2010.
7. Jacobo-Salcedo, M. del R., Alonso-Castro, A. J. et al. Antimicrobial and
cyttoxic effects of Mexican medicinal plants. NPC, Vol. 6, No. 12, 1925-1928,
2011.
8. Wang, D., Jin, Q., Xiang, H. et al. Transcriptional and function analysis of the
effects of manolol: Inhibition of autolysis and biofilm in Staphylococcus
aureus. PLoS ONE, Vol. 6, Issue 10, 2011.
9. 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 10(2), 2015.
10. Tiwari, V., Roy, R., Tiwari, M.. Antimicrobial active herbal compounds gainst
Acinetobacter baumannii an other pathogens. Frontier in Microbiology, Vol. 6,
Article 618, 2015.
11. Cui, J., Ren, B., Tong, Y. et al. Synergistic combinations of antifungals and
anti-virulence agents to fight against Candida albicans. LLC, Vol. 6:4, 362-
371, 2015.
12. Yuuki, S., Hisanori, D., Masataka, O. et al. Anti-biofilm and bactericidal
effects of magnolia bark-derived magnolol and honokiol on Streptococcus
mutans. Microbiol Immunol, 60, 10-16, 2016.
13. Poivre, M., Duez, P.. Biologycal activity and toxicity of the Chinese herb
Magnolia officinalis Rehder & E. Wilson (Houpo) and its constituents. Journal
of Zhejiang University-SCIENCE B, 18(3), 194-214, 2017.
14. Choi, W. S., Lee, T. H., Son, S. J. et al. Inhibitory effect of obovatol from
Magnolia obovata on the Salmonella type III secretion system. The journal of
 antibiotics, 70, 1065-1069, 2017.
15. Zhou, P., Fu, J., Hua, H., Liu, X.. In vitro inhibitory activities of magnolol
against Candida spp. Dove press journal: Drug design, Development and
therapy, 11, 2653-2661, 2017.
16. Feng, J., Li, JU., Jou, XD. Effects of the active compounds of M. officinalis
on cariogenic bacteria. Journal of Sichuan university, Medical science edition,
38(3), 456-458, 2007
17. Ma, R. et al. Effect of compound Chinese traditional medicine on infected root
canal bacteria biofilm. Shanghai Journal of Stomatology, 19(4), 415-418, 2010
18. Chang, B. S., Lee, Y. M., Ku, Y., Bae, K. H. and Chung, C. P. Antimicrobial
activity of magnolol and honokiol against periodontopathic microorganisms.
Planta Medica, 64, 367-369 , 1998.
19. Namba, T., Tsunezuka, M., Bae, K. H. and Hattori, M. Studies on dental caries
prevention by traditional Chinese medicines (part I), Screening of crude drugs
for antibacterial action against Streptococcus mutans. Shoyaku Zasshi, 35,
295-302 1981.
20. Namba, T., Tsunezuka, M. and Hattori, M., Dental caries by traditional
Chinese medicines (part II), Potent antibacterial action of Magnoliae Cortex
extracts against Streptococcus mutans. Planta Medica, 44, 100-106, 1982.
21. Bae, K., Yoo, B., Lee, M. and Seo, W., Antimicrobial activities of
hydroxybiphenyl derivatives (I), Antibacterial activities and HPLC
determination of magnolol and honokiol. Arch. Pharm. Res., 8, 85-89 (1985)
22. Seo, W. J., Koo, S. H. and Bae, K. H., Antimicrobial activity of
hydroxybiphenyl derivatives. Arch. Pharm. Res., 9, 127-130 (1986).
23. Wang, JP. et al. Anti-inflammatory effects of magnolol, isolated freom
Magnolia officinalis, on A23187-induce pleurisy in mice. JPharm Pharmacol
47, 857-860, 1995.
24. Clark, AM. Et al. Antimicrobial activity of phenolic constituents of Magnolia
grandiflora. J Pharm Sci 70, 951-952, 1981.
25. Lee, YJ., Lee, YM. Et al. Therapeutic applications of compounds in the
Magnolia family. Pharmacol Ther, 130(2):157–176, 2011.