Natural cinnamic acids, synthetic derivatives and hybrids with antimicrobial activity

Molecules

Volumn 19, Issue 12, 2014, Pages 19292-19349

  Guzman, Juan David ^a  

^a UNIVERSIDAD DEL NORTE   (Colombia)

Author keywords

Antimicrobial; Cinnamic acid; Coumaric acids; Hybrids; Tuberculosis

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE; AMIDE; ANTIINFECTIVE AGENT; CINNAMIC ACID; CINNAMIC ACID DERIVATIVE; ESTER;

ALCOHOLS; ALDEHYDES; AMIDES; ANTI-INFECTIVE AGENTS; CINNAMATES; ESTERS;

EID: 84919774843     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules191219292     Document Type: Review

References (166)

1. Xu, Z.; Zhang, D.; Hu, J.; Zhou, X.; Ye, X.; Reichel, K.; Stewart, N.; Syrenne, R.; Yang, X.; Gao, P.; et al. Comparative genome analysis of lignin biosynthesis gene families across the plant kingdom. BMC Bioinform. 2009, 10, S3.
2. Lichtenthaler, H.K.; Schweiger, J. Cell wall bound ferulic acid, the major substance of the blue-green fluorescence emission of plants. J. Plant Physiol. 1998, 152, 272-282.
3. Kroon, P.A.; Williamson, G. Hydroxycinnamates in plants and food: current and future perspectives. J. Sci. Food Agric. 1999, 79, 355-361.
4. Martin-Tanguy, J.; Cabanne, F.; Perdrizet, E.; Martin, C. The distribution of hydroxycinnamic acid amides in flowering plants. Phytochemistry 1978, 17, 1927-1928.
5. Vogt, T. Phenylpropanoid biosynthesis. Mol. Plant 2010, 3, 2-20.
6. Ververidis, F.; Trantas, E.; Douglas, C.; Vollmer, G.; Kretzschmar, G.; Panopoulos, N. Biotechnology of flavonoids and other phenylpropanoid-derived natural products. Part I: Chemical diversity, impacts on plant biology and human health. Biotech. J. 2007, 2, 1214-1234.
7. Solecka, D. Role of phenylpropanoid compounds in plant responses to different stress factors. Acta Physiol. Plant 1997, 19, 257-268.
8. Hyun, M.W.; Yun, Y.H.; Kim, J.Y.; Kim, S.H. Fungal and plant phenylalanine ammonia-lyase. Mycobiology 2011, 39, 257-65.
9. Pittman, S. Cinnamon: It's not just for making cinnamon rolls. Ethnobot. Leafl. 2011, 2000, 11.
10. Wang, R.; Wang, R.; Yang, B. Extraction of essential oils from five cinnamon leaves and identification of their volatile compound compositions. Innov. Food Sci. Emerg. 2009, 10, 289-292.
11. Ooi, L.S.M.; Li, Y.; Kam, S.-L.; Wang, H.; Wong, E.Y.L.; Ooi, V.E.C. Antimicrobial Activities of cinnamon oil and cinnamaldehyde from the Chinese medicinal herb Cinnamomum cassia Blume. Am. J. Chin. Med. 2006, 34, 511-522.
12. Chang, S.-T.; Chen, P.-F.; Chang, S.-C. Antibacterial activity of leaf essential oils and their constituents from Cinnamomum osmophloeum. J. Ethnopharmacol. 2001, 77, 123-127.
13. Shahverdi, A.R.; Monsef-Esfahani, H.R.; Tavasoli, F.; Zaheri, A.; Mirjani, R. Trans-cinnamaldehyde from Cinnamomum zeylanicum bark essential oil reduces the clindamycin resistance of Clostridium difficile in vitro. J. Food Sci. 2007, 72, S055-S058.
14. Clifford, M.N. Chlorogenic acids and other cinnamates-nature, occurrence and dietary burden. J. Sci. Food Agric. 1999, 79, 362-372.
15. Zhang, J.; Yang, J.; Chang, X.; Zhang, C.; Zhou, H.; Liu, M. Ozagrel for acute ischemic stroke: A meta-analysis of data from randomized controlled trials. Neurol. Res. 2012, 34, 346-353.
16. Wilensky, A.J.; Ojemann, L.M.; Friel, P.N.; Almes, M.J.; Levy, R.H.; Dodrill, C.B. Cinromide in epilepsy: A pilot study. Epilepsia 1983, 24, 401-409.
17. Bezerra, D.P.; Pessoa, C.; de Moraes, M.O.; Saker-Neto, N.; Silveira, E.R.; Costa-Lotufo, L.V. Overview of the therapeutic potential of piplartine (piperlongumine). Eur. J. Pharm. Sci. 2012, 48, 453-463.
18. Filho, R.B.; De Souza, M.P.; Mattos, M.E.O. Piplartine-dimer A, a new alkaloid from Piper tuberculatum. Phytochemistry 1981, 20, 345-346.
19. Bezerra, D.P.; Pessoa, C.; de Moraes, M.O.; Silveira, E.R.; Lima, M.A.; Elmiro, F.J.; Costa-Lotufo, L.V. Antiproliferative effects of two amides, piperine and piplartine, from Piper species. Z. Naturforsch. C Biol. Sci. 2005, 60, 539-543.
20. Bezerra, D.P.; Militao, G.C.; de Castro, F.O.; Pessoa, C.; de Moraes, M.O.; Silveira, E.R.; Lima, M.A.; Elmiro, F.J.; Costa-Lotufo, L.V. Piplartine induces inhibition of leukemia cell proliferation triggering both apoptosis and necrosis pathways. Toxicol. In Vitro 2007, 21, 1-8.
21. De, P.; Baltas, M.; Bedos-Belval, F. Cinnamic acid derivatives as anticancer agents - a review. Curr. Med. Chem. 2011, 18, 1672-1703.
22. De, P.; Veau, D.; Bedos-Belval, F.; Chassaing, S.; Baltas, M. Cinnamic derivatives in tuberculosis. In Understanding Tuberculosis-New Approaches to Fighting against Drug Resistance; Cardona, P.-J., Ed.; InTech Publishing: Rijeka, Croatia, 2012; Chapter 15.
23. Wiesner, J.; Mitsch, A.; Wiβner, P.; Jomaa, H.; Schlitzer, M. Structure-activity relationships of novel anti-malarial agents. Part 2: Cinnamic acid derivatives. Bioorg. Med. Chem. Lett. 2001, 11, 423-424.
24. Tawata, S.; Taira, S.; Kobamoto, N.; Zhu, J.; Ishihara, M.; Toyama, S. Synthesis and antifungal activity of cinnamic acid esters. Biosci. Biotechnol. Biochem. 1996, 60, 909-910.
25. Sova, M. Antioxidant and antimicrobial activities of cinnamic acid derivatives. Mini Rev. Med. Chem. 2012, 12, 749-767.
26. Lapeyre, C.; Delomenède, M.; Bedos-Belval, F.; Duran, H.; Nègre-Salvayre, A.; Baltas, M. Design, synthesis, and evaluation of pharmacological properties of cinnamic derivatives as antiatherogenic agents. J. Med. Chem. 2005, 48, 8115-8124.
27. Simonyan, A. Activity of cinnamic acid derivatives and new methods for their synthesis (review). Pharm. Chem. J. 1993, 27, 92-100.
28. Wall, V.M.; Eisenstadt, A.; Ager, D.J.; Laneman, S.A. The Heck reaction and cinnamic acid synthesis by heterogeneous catalysis. Platin. Metals Rev. 1999, 43, 138-144.
29. Sharma, P. Cinnamic acid derivatives: A new chapter of various pharmacological activities. J. Chem. Pharm. Res. 2011, 3, 403-423.
30. Bygbjerg, I.C. Double burden of noncommunicable and infectious diseases in developing countries. Science 2012, 337, 1499-1501.
31. Coker, R.J.; Hunter, B.M.; Rudge, J.W.; Liverani, M.; Hanvoravongchai, P. Emerging infectious diseases in southeast Asia: Regional challenges to control. Lancet 2011, 377, 599-609.
32. Mabey, D.; Peeling, R.W.; Ustianowski, A.; Perkins, M.D. Tropical infectious diseases: Diagnostics for the developing world. Nat. Rev. Microbiol. 2004, 2, 231-240.
33. Fauci, A.S.; Morens, D.M. The perpetual challenge of infectious diseases. N. Eng. J. Med. 2012, 366, 454-461.
34. WHO. The Global Burden of Disease: 2004 Update; World Health Organization: Geneva, Switzerland, 2008; pp. 7-22.
35. Powers, J.H. Antimicrobial drug development-The past, the present, and the future. Clin. Microbiol. Infect. 2004, 10, 23-31.
36. Gold, H.S.; Moellering, R.C. Antimicrobial-drug resistance. N. Eng. J. Med. 1996, 335, 1445-1453.
37. Cohen, M.L. Epidemiology of drug resistance: Implications for a post-Antimicrobial era. Science 1992, 257, 1050-1055.
38. Sotgiu, G.; Centis, R.; D'Ambrosio, L.; Tadolini, M.; Castiglia, P.; Migliori, G.B. Do we need a new Fleming époque: The nightmare of drug-resistant tuberculosis. Int. J. Mycobacteriol. 2013, 2, 123-125.
39. David, M.Z.; Daum, R.S. Community-associated methicillin-resistant Staphylococcus aureus: Epidemiology and clinical consequences of an emerging epidemic. Clin. Microbiol. Rev. 2010, 23, 616-687.
40. MacGowan, A.; Macnaughton, E. Antibiotic resistance. Medicine 2013, 41, 642-648.
41. Hancock, R.E.W. Mechanisms of action of newer antibiotics for Gram-positive pathogens. Lancet Infect. Dis. 2005, 5, 209-218.
42. Korošec, B.; Sova, M.; Turk, S.; Kraševec, N.; Novak, M.; Lah, L.; Stojan, J.; Podobnik, B.; Berne, S.; Zupanec, N.; et al. Antifungal activity of cinnamic acid derivatives involves inhibition of benzoate 4-hydroxylase (CYP53). J. Appl. Microbiol. 2014, 116, 955-966.
43. Jitareanu, A.; Tataringa, G.; Zbancioc, A.M.; Tuchilus, C.; Stanescu, U. Antimicrobial activity of some cinnamic acid derivatives. Rev. Med. Chir. Soc. Med. Nat. Iasi 2011, 115, 965-971.
44. Narasimhan, B.; Belsare, D.; Pharande, D.; Mourya, V.; Dhake, A. Esters, amides and substituted derivatives of cinnamic acid: Synthesis, antimicrobial activity and QSAR investigations. Eur. J. Med. Chem. 2004, 39, 827-834.
45. Hemaiswarya, S.; Doble, M. Synergistic interaction of phenylpropanoids with antibiotics against bacteria. J. Med. Microbiol. 2010, 59, 1469-1476.
46. Wen, A.; Delaquis, P.; Stanich, K.; Toivonen, P. Antilisterial activity of selected phenolic acids. Food Microbiol. 2003, 20, 305-311.
47. Kujumgiev, A.; Tsvetkova, I.; Serkedjieva, Y.; Bankova, V.; Christov, R.; Popov, S. Antibacterial, antifungal and antiviral activity of propolis of different geographic origin. J. Ethnopharmacol. 1999, 64, 235-240.
48. Simone-Finstrom, M.; Spivak, M. Propolis and bee health: The natural history and significance of resin use by honey bees. Apidologie 2010, 41, 295-311.
49. Bankova, V.; Christov, R.; Kujumgiev, A.; Marcucci, M.C.; Popov, S. Chemical composition and antibacterial activity of Brazilian propolis. Z. Naturforsch. C Bio. Sci. 1995, 50, 167-172.
50. Bankova, V.S.; Popov, S.S.; Marekov, N.L. Isopentenyl cinnamates from poplar buds and propolis. Phytochemistry 1989, 28, 871-873.
51. Bankova, V.S.; de Castro, S.L.; Marcucci, M.C. Propolis: Recent advances in chemistry and plant origin. Apidologie 2000, 31, 3-16.
52. Mohammadzadeh, S.; Shariatpanahi, M.; Hamedi, M.; Ahmadkhaniha, R.; Samadi, N.; Ostad, S.N. Chemical composition, oral toxicity and antimicrobial activity of Iranian propolis. Food Chem. 2007, 103, 1097-1103.
53. Stepanović, S.; Antić, N.; Dakić, I.; Švabić-Vlahović, M. In vitro antimicrobial activity of propolis and synergism between propolis and antimicrobial drugs. Microbiol. Res. 2003, 158, 353-357.
54. Koo, H.; Gomes, B.P.F.A.; Rosalen, P.L.; Ambrosano, G.M.B.; Park, Y.K.; Cury, J.A. In vitro antimicrobial activity of propolis and Arnica montana against oral pathogens. Arch. Oral Biol. 2000, 45, 141-148.
55. Hewitt, W.; Vincent, S. Theory and Application of Microbiological Assay; Academic Press: San Diego, CA, USA, 1989; pp. 1-37.
56. Olasupo, N.A.; Fitzgerald, D.J.; Gasson, M.J.; Narbad, A. Activity of natural antimicrobial compounds against Escherichia coli and Salmonella enterica serovar Typhimurium. Lett. Appl. Microbiol. 2003, 37, 448-451.
57. Rastogi, N.; Domadia, P.; Shetty, S.; Dasgupta, D. Screening of natural phenolic compounds for potential to inhibit bacterial cell division protein FtsZ. Ind. J. Exp. Biol. 2008, 46, 783-787.
58. Alves, M.J.; Ferreira, I.C.; Froufe, H.J.; Abreu, R.M.; Martins, A.; Pintado, M. Antimicrobial activity of phenolic compounds identified in wild mushrooms, SAR analysis and docking studies. J. Appl. Microbiol. 2013, 115, 346-357.
59. Prasad, V.G.N.V.; Krishna, B.V.; Swamy, P.L.; Rao, T.S.; Rao, G.S. Antibacterial synergy between quercetin and polyphenolic acids against bacterial pathogens of fish. Asian Pac. J. Trop. Dis. 2014, 4 (Suppl. 1), S326-S329.
60. Guzman, J.D.; Mortazavi, P.N.; Munshi, T.; Evangelopoulos, D.; McHugh, T.D.; Gibbons, S.; Malkinson, J.; Bhakta, S.2-Hydroxy-substituted cinnamic acids and acetanilides are selective growth inhibitors of Mycobacterium tuberculosis. MedChemComm 2014, 5, 47-50.
61. Guzman, J.D.; Evangelopoulos, D.; Gupta, A.; Birchall, K.; Mwaigwisya, S.; Saxty, B.; McHugh, T.D.; Gibbons, S.; Malkinson, J.; Bhakta, S. Antitubercular specific activity of ibuprofen and the other 2-arylpropanoic acids using the HT-SPOTi whole-cell phenotypic assay. BMJ Open 2013, 3, e002672-e002685.
62. Rastogi, N.; Goh, K.S.; Horgen, L.; Barrow, W.W. Synergistic activities of antituberculous drugs with cerulenin and trans-cinnamic acid against Mycobacterium tuberculosis. FEMS Immunol. Med. Microbiol. 1998, 21, 149-157.
63. Chen, Y.L.; Huang, S.T.; Sun, F.M.; Chiang, Y.L.; Chiang, C.J.; Tsai, C.M.; Weng, C.J. Transformation of cinnamic acid from trans- to cis-form raises a notable bactericidal and synergistic activity against multiple-drug resistant Mycobacterium tuberculosis. Eur. J. Pharm. Sci. 2011, 43, 188-194.
64. Warbasse, J.P. Cinnamic acid in the treatment of tuberculosis. Ann. Surg. 1894, 19, 102-111.
65. Bisogno, F.; Mascoti, L.; Sanchez, C.; Garibotto, F.; Giannini, F.; Kurina-Sanz, M.; Enriz, R. Structure-antifungal activity relationship of cinnamic acid derivatives. J. Agric. Food Chem. 2007, 55, 10635-10640.
66. Schmidt, E.; Bail, S.; Friedl, S.M.; Jirovetz, L.; Buchbauer, G.; Wanner, J.; Denkova, Z.; Slavchev, A.; Stoyanova, A.; Geissler, M. Antimicrobial activities of single aroma compounds. Nat. Prod. Commun. 2010, 5, 1365-1368.
67. Lou, Z.; Wang, H.; Rao, S.; Sun, J.; Ma, C.; Li, J. p-Coumaric acid kills bacteria through dual damage mechanisms. Food Control 2012, 25, 550-554.
68. Barber, M.S.; McConnell, V.S.; DeCaux, B.S. Antimicrobial intermediates of the general phenylpropanoid and lignin specific pathways. Phytochemistry 2000, 54, 53-56.
69. Parkar, S.G.; Stevenson, D.E.; Skinner, M.A. The potential influence of fruit polyphenols on colonic microflora and human gut health. Int. J. Food Microbiol. 2008, 124, 295-298.
70. Tunçel, G.; Nergiz, C. Antimicrobial effect of some olive phenols in a laboratory medium. Lett. Appl. Microbiol. 1993, 17, 300-302.
71. García-Ruiz, A.; Bartolomé, B.; Cueva, C.; Martín-Álvarez, P.J.; Moreno-Arribas, M.V. Inactivation of oenological lactic acid bacteria (Lactobacillus hilgardii and Pediococcus pentosaceus) by wine phenolic compounds. J. Appl. Microbiol. 2009, 107, 1042-1053.
72. Stead, D. The effect of hydroxycinnamic acids on the growth of wine-spoilage lactic acid bacteria. J. Appl. Bacteriol. 1993, 75, 135-141.
73. Zabka, M.; Pavela, R. Antifungal efficacy of some natural phenolic compounds against significant pathogenic and toxinogenic filamentous fungi. Chemosphere 2013, 93, 1051-1056.
74. Puupponen-Pimiä, R.; Nohynek, L.; Alakomi, H.-L.; Oksman-Caldentey, K.-M. Bioactive berry compounds-Novel tools against human pathogens. Appl. Microbiol. Biotechnol. 2005, 67, 8-18.
75. Gasparetto, J.C.; Guimarães de Francisco, T.M.; Campos, F.R.; Pontarolo, R. Development and validation of two methods based on high-performance liquid chromatography-tandem mass spectrometry for determining 1,2-benzopyrone, dihydrocoumarin, o-coumaric acid, syringaldehyde and kaurenoic acid in guaco extracts and pharmaceutical preparations. J. Sep. Sci. 2011, 34, 740-748.
76. Herald, P.J.; Davidson, P.M. Antibacterial activity of selected hydroxycinnamic acids. J. Food Sci. 1983, 48, 1378-1379.
77. Georgiev, L.; Chochkova, M.; Ivanova, G.; Najdenski, H.; Ninova, M.; Milkova, T. Radical scavenging and antimicrobial activities of cinnamoyl amides of biogenic monoamines. Riv. Ital. Sost. Grasse 2012, 89, 91-102.
78. De Vita, D.; Friggeri, L.; D'Auria, F.D.; Pandolfi, F.; Piccoli, F.; Panella, S.; Palamara, A.T.; Simonetti, G.; Scipione, L.; di Santo, R.; et al. Activity of caffeic acid derivatives against Candida albicans biofilm. Bioorg. Med. Chem. Lett. 2014, 24, 1502-1505.
79. Borges, A.; Ferreira, C.; Saavedra, M.J.; Simoes, M. Antibacterial activity and mode of action of ferulic and gallic acids against pathogenic bacteria. Microb. Drug Resist. 2013, 19, 256-265.
80. Nakauchi, M.; Ikemoto, S.; Yamanishi, H.; Ozaki, Y.; Tsuno, T.; Nomura, E.; Hosoda, A.; Taniguchi, H. Antimicrobial activities of synthetic ferulic acid derivatives. Food Preserv. Sci. 2002, 28, 183-188.
81. Ergün, B.; Çoban, T.; Onurdag, F.; Banoglu, E. Synthesis, antioxidant and antimicrobial evaluation of simple aromatic esters of ferulic acid. Arch. Pharm. Res. 2011, 34, 1251-1261.
82. Klančnik, A.; Možina, S.S.; Zhang, Q. Anti-Campylobacter activities and resistance mechanisms of natural phenolic compounds in Campylobacter. PLoS One 2012, 7, e51800.
83. Engels, C.; Schieber, A.; Gänzle, M. Sinapic acid derivatives in defatted Oriental mustard (Brassica juncea L.) seed meal extracts using UHPLC-DAD-ESI-MS n and identification of compounds with antibacterial activity. Eur. Food Res. Technol. 2012, 234, 535-542.
84. Nakazono, Y.; Watanabe, Y.; Hashinaga, F.; Tadera, K. Studies on antimicrobial and antioxidative substance of Yuzu (Citrus junos hort. ex Tanaka) seed. J. Biol. Sci. 2006, 6, 135-139.
85. Cheng, M.-J.; Wu, M.-D.; Yanai, H.; Su, Y.-S.; Chen, I.-S.; Yuan, G.-F.; Hsieh, S.-Y.; Chen, J.-J. Secondary metabolites from the endophytic fungus Biscogniauxia formosana and their antimycobacterial activity. Phytochem. Lett. 2012, 5, 467-472.
86. Tonari, K.; Mitsui, K.; Yonemoto, K. Structure and antibacterial activity of cinnamic acid related compounds. J. Oleo Sci. 2002, 51, 271-273.
87. Feasley, C.F.; Gwynn, B.H.; Degering, F.; Tetrault, P.A. Bacteriostatic properties of phenylacetic acid. Effect of ortho-substituents on. J. Am. Pharm. Assoc. 1941, 30, 41-45.
88. Kanao, S.; Kashino, S.; Haisa, M. Topochemical studies. XIII. Structures of 3-bromocinnamic acid and 3-chlorocinnamic acid. Acta Crystallograph. Sect. C Cryst. Struct. Commun. 1990, 46, 2436-2438.
89. Schaldach, B.; Grützmacher, H.F. The fragmentations of substituted cinnamic acids after electron impact. Org. Mass Spectrom. 1980, 15, 175-181.
90. Newby, B.M.Z.; Cutright, T.; Barrios, C.; Xu, Q. Zosteric acid-An effective antifoulant for reducing fresh water bacterial attachment on coatings. J. Coat. Technol. Res. 2006, 3, 69-76.
91. Villa, F.; Pitts, B.; Stewart, P.; Giussani, B.; Roncoroni, S.; Albanese, D.; Giordano, C.; Tunesi, M.; Cappitelli, F. Efficacy of zosteric acid sodium salt on the yeast biofilm model Candida albicans. Microb. Ecol. 2011, 62, 584-598.
92. Feresin, G.E.; Tapia, A.; Gimenez, A.; Ravelo, A.G.; Zacchino, S.; Sortino, M.; Schmeda-Hirschmann, G. Constituents of the Argentinian medicinal plant Baccharis grisebachii and their antimicrobial activity. J. Ethnopharmacol. 2003, 89, 73-80.
93. Hermans, D.; Martel, A.; van Deun, K.; van Immerseel, F.; Heyndrickx, M.; Haesebrouck, F.; Pasmans, F. The cinnamon-oil ingredient trans-cinnamaldehyde fails to target Campylobacter jejuni strain KC 40 in the broiler chicken cecum despite marked In vitro activity. J. Food Prot. 2011, 74, 1729-1734.
94. Tesaki, S.; Tanabe, S.; Ono, H.; Fukushi, E.; Kawabata, J.; Watanabe, M. 4-Hydroxy-3-nitrophenylacetic and sinapic acids as antibacterial compounds from mustard seeds. Biosci. Biotechnol. Biochem. 1998, 62, 998-1000.
95. Olthof, M.R.; Hollman, P.C. H.; Katan, M.B. Chlorogenic acid and caffeic acid are absorbed in humans. J. Nutr. 2001, 131, 66-71.
96. Zhu, X.; Zhang, H.; Lo, R. Phenolic compounds from the leaf extract of artichoke (Cynara scolymus L.) and their antimicrobial activities. J. Agric. Food Chem. 2004, 52, 7272-7278.
97. Daglia, M.; Papetti, A.; Grisoli, P.; Aceti, C.; Spini, V.; Dacarro, C.; Gazzani, G. Isolation, identification, and quantification of roasted coffee antibacterial compounds. J. Agric. Food Chem. 2007, 55, 10208-10213.
98. Xia, D.; Wu, X.; Shi, J.; Yang, Q.; Zhang, Y. Phenolic compounds from the edible seeds extract of Chinese Mei (Prunus mume Sieb. et Zucc) and their antimicrobial activity. LWT-Food Sci. Technol. 2011, 44, 347-349.
99. Fiamegos, Y.C.; Kastritis, P.L.; Exarchou, V.; Han, H.; Bonvin, A.M.J.J.; Vervoort, J.; Lewis, K.; Hamblin, M.R.; Tegos, G.P. Antimicrobial and efflux pump inhibitory activity of caffeoylquinic acids from Artemisia absinthium against Gram-positive pathogenic bacteria. PLoS One 2011, 6, e18127.
100. Lou, Z.; Wang, H.; Zhu, S.; Ma, C.; Wang, Z. Antibacterial activity and mechanism of action of chlorogenic acid. J. Food Sci. 2011, 76, M398-M403.
101. Zhang, M.; Liu, W.-X.; Zheng, M.-F.; Xu, Q.-L.; Wan, F.-H.; Wang, J.; Lei, T.; Zhou, Z.-Y.; Tan, J.-W. Bioactive quinic acid derivatives from Ageratina adenophora. Molecules 2013, 18, 14096-14104.
102. Kang, K.; Jang, S.; Kim, B.-K.; Park, M. Antibacterial phenylpropanoid glycosides from Paulownia tomentosa Steud. Arch. Pharm. Res. 1994, 17, 470-475.
103. Svetaz, L.; Tapia, A.; López, S.N.; Furlán, R.L.E.; Petenatti, E.; Pioli, R.; Schmeda-Hirschmann, G.; Zacchino, S.A. Antifungal chalcones and new caffeic acid esters from Zuccagnia punctata acting against soybean infecting fungi. J. Agric. Food Chem. 2004, 52, 3297-3300.
104. Abedini, A.; Roumy, V.; Mahieux, S.; Biabiany, M.; Standaert-Vitse, A.; Riviere, C.; Sahpaz, S.; Bailleul, F.; Neut, C.; Hennebelle, T. Rosmarinic acid and its methyl ester as antimicrobial components of the hydromethanolic extract of Hyptis atrorubens Poit. (Lamiaceae). Evid. Based Complement. Altern. Med. 2013, 2013, 604536:1-604536:11.
105. Lin, L.; Zhu, D.; Zou, L.; Yang, B.; Zhao, M. Antibacterial activity-guided purification and identification of a novel C-20 oxygenated ent-kaurane from Rabdosia serra (Maxim.) Hara. Food Chem. 2013, 139, 902-909.
106. Gohari, A.R.; Saeidnia, S.; Shahverdi, A.R.; Yassa, N.; Malmir, M.; Mollazade, K.; Naghinejad, A.R. Phytochemistry and antimicrobial compounds of Hymenocrater calycinus. EurAsian J. Biosci. 2009, 3, 64-68.
107. Grunberger, D.; Banerjee, R.; Eisinger, K.; Oltz, E.M.; Efros, L.; Caldwell, M.; Estevez, V.; Nakanishi, K. Preferential cytotoxicity on tumor cells by caffeic acid phenethyl ester isolated from propolis. Experientia 1988, 44, 230-232.
108. Velazquez, C.; Navarro, M.; Acosta, A.; Angulo, A.; Dominguez, Z.; Robles, R.; Robles-Zepeda, R.; Lugo, E.; Goycoolea, F.M.; Velazquez, E.F.; et al. Antibacterial and free-radical scavenging activities of Sonoran propolis. J. Appl. Microbiol. 2007, 103, 1747-1756.
109. Ango, P.Y.; Kapche, D.W.F.G.; Kuete, V.; Ngadjui, B.T.; Bezabih, M.; Abegaz, B.M. Chemical constituents of Trilepisium madagascariense (Moraceae) and their antimicrobial activity. Phytochem. Lett. 2012, 5, 524-528.
110. Chien, Y.C.; Lin, C.H.; Chiang, M.Y.; Chang, H.S.; Liao, C.H.; Chen, I.S.; Peng, C.F.; Tsai, I.L. Secondary metabolites from the root of Ehretia longiflora and their biological activities. Phytochemistry 2012, 80, 50-57.
111. Khatkar, A.; Nanda, A.; Kumar, P.; Narasimhan, B. Synthesis, antimicrobial evaluation and QSAR studies of p-coumaric acid derivatives. Arab. J. Chem. 2014, in press.
112. Lakshmanan, D.; Werngren, J.; Jose, L.; Suja, K.P.; Nair, M.S.; Varma, R.L.; Mundayoor, S.; Hoffner, S.; Kumar, R.A. Ethyl p-methoxycinnamate isolated from a traditional anti-tuberculosis medicinal herb inhibits drug resistant strains of Mycobacterium tuberculosis in vitro. Fitoterapia 2011, 82, 757-761.
113. Dyer, L.A.; Richards, J.; Dodson, C.D. Isolation, synthesis, and evolutionary ecology of Piper amides. In Piper: A Model Genus for Studies of Phytochemistry, Ecology, and Evolution; Dyer, L.A., Palmer, A.D.N., Eds.; Springer: New York, NY, USA, 2004; pp. 117-139.
114. Naika, R.; Prasanna, K.; Ganapathy, P. Antibacterial activity of piperlongumine an alkaloid isolated from the methanolic root extract of Piper longum L. Pharmacophore 2010, 1, 141-148.
115. Navickiene, H.M.D.; Alécio, A.C.; Kato, M.J.; Bolzani, V.D.S.; Young, M.C.M.; Cavalheiro, A.J.; Furlan, M. Antifungal amides from Piper hispidum and Piper tuberculatum. Phytochemistry 2000, 55, 621-626.
116. Vasques da Silva, R.; Debonsi Navickiene, H.M.; Kato, M.J.; Bolzani, V.D.S.; Méda, C.I.; Young, M.C.M.; Furlan, M. Antifungal amides from Piper arboreum and Piper tuberculatum. Phytochemistry 2002, 59, 521-527.
117. Rukachaisirikul, T.; Siriwattanakit, P.; Sukcharoenphol, K.; Wongvein, C.; Ruttanaweang, P.; Wongwattanavuch, P.; Suksamrarn, A. Chemical constituents and bioactivity of Piper sarmentosum. J. Ethnopharmacol. 2004, 93, 173-176.
118. Tuntiwachwuttikul, P.; Phansa, P.; Pootaeng-On, Y.; Taylor, W.C. Chemical constituents of the roots of Piper sarmentosum. Chem. Pharm. Bull. 2006, 54, 149-151.
119. Samwel, S.; Odalo, J.O.; Nkunya, M.H.; Joseph, C.C.; Koorbanally, N.A. Toussaintines A-E: Antimicrobial indolidinoids, a cinnamoylhydrobenzofuranoid and a cinnamoylcyclohexenoid from Toussaintia orientalis leaves. Phytochemistry 2011, 72, 1826-1832.
120. Jantan, I.B.; Karim Moharam, B.A.; Santhanam, J.; Jamal, J.A. Correlation between chemical composition and antifungal activity of the essential oils of eight Cinnamomum species. Pharm. Biol. 2008, 46, 406-412.
121. Ali, S.; Khan, A.; Ahmed, I.; Musaddiq, M.; Ahmed, K.; Polasa, H.; Rao, L.V.; Habibullah, C.; Sechi, L.; Ahmed, N. Antimicrobial activities of eugenol and cinnamaldehyde against the human gastric pathogen Helicobacter pylori. Ann. Clin. Microbiol. Antimicrob. 2005, 4, 20-27.
122. Cox, S.D.; Markham, J.L. Susceptibility and intrinsic tolerance of Pseudomonas aeruginosa to selected plant volatile compounds. J. Appl. Microbiol. 2007, 103, 930-936.
123. Pei, R.-S.; Zhou, F.; Ji, B.-P.; Xu, J. Evaluation of combined antibacterial effects of eugenol, cinnamaldehyde, thymol, and carvacrol against E. coli with an improved method. J. Food Sci. 2009, 74, M379-M383.
124. Domadia, P.; Swarup, S.; Bhunia, A.; Sivaraman, J.; Dasgupta, D. Inhibition of bacterial cell division protein FtsZ by cinnamaldehyde. Biochem. Pharmacol. 2007, 74, 831-840.
125. Kim, H.O.; Park, S.W.; Park, H.D. Inactivation of Escherichia coli O157:H7 by cinnamic aldehyde purified from Cinnamomum cassia shoot. Food Microbiol. 2004, 21, 105-110.
126. Shimizu, I.; Isshiki, Y.; Nomura, H.; Sakuda, K.; Sakuma, K.; Kondo, S. The antibacterial activity of fragrance ingredients against Legionella pneumophila. Biol. Pharm. Bull. 2009, 32, 1114-1117.
127. Kwon, J.A.; Yu, C.B.; Park, H.D. Bacteriocidal effects and inhibition of cell separation of cinnamic aldehyde on Bacillus cereus. Lett. Appl. Microbiol. 2003, 37, 61-65.
128. Jia, P.; Xue, Y.J.; Duan, X.J.; Shao, S.H. Effect of cinnamaldehyde on biofilm formation and sarA expression by methicillin-resistant Staphylococcus aureus. Lett. Appl. Microbiol. 2011, 53, 409-416.
129. Xing, F.; Hua, H.; Selvaraj, J.N.; Zhao, Y.; Zhou, L.; Liu, X.; Liu, Y. Growth inhibition and morphological alterations of Fusarium verticillioides by cinnamon oil and cinnamaldehyde. Food Control 2014, 46, 343-350.
130. Shreaz, S.; Sheikh, R.A.; Rimple, B.; Hashmi, A.A.; Nikhat, M.; Khan, L.A. Anticandidal activity of cinnamaldehyde, its ligand and Ni(II) complex: Effect of increase in ring and side chain. Microb. Pathog. 2010, 49, 75-82.
131. Ferhout, H.; Bohatier, J.; Guillot, J.; Chalchat, J.C. Antifungal activity of selected essential oils, cinnamaldehyde and carvacrol against Malassezia furfur and Candida albicans. J. Essent. Oil Res. 1999, 11, 119-129.
132. Rajput, S.B.; Karuppayil, S.M. Small molecules inhibit growth, viability and ergosterol biosynthesis in Candida albicans. Springer Plus 2013, 2, 26-28.
133. Yen, T.-B.; Chang, S.-T. Synergistic effects of cinnamaldehyde in combination with eugenol against wood decay fungi. Bioresour. Technol. 2008, 99, 232-236.
134. Hsu, F.-L.; Chang, H.-T.; Chang, S.-T. Evaluation of antifungal properties of octyl gallate and its synergy with cinnamaldehyde. Bioresour. Technol. 2007, 98, 734-738.
135. Chen, S.; Huang, H.-Y.; Cheng, M.-J.; Wu, C.-C.; Ishikawa, T.; Peng, C.-F.; Chang, H.-S.; Wang, C.-J.; Wong, S.-L.; Chen, I.-S. Neolignans and phenylpropanoids from the roots of Piper taiwanense and their antiplatelet and antitubercular activities. Phytochemistry 2013, 93, 203-209.
136. + extrusion activity and ultrastructure of Candida. J. Med. Microbiol. 2013, 62, 232-240.
137. Meerungrueang, W.; Panichayupakaranant, P. Antimicrobial activities of some Thai traditional medical longevity formulations from plants and antibacterial compounds from Ficus foveolata. Pharm. Biol. 2014, 52, 1104-1109.
138. Morozumi, S. Isolation, purification, and antibiotic activity of o-methoxycinnamaldehyde from cinnamon. Appl. Environ. Microbiol. 1978, 36, 577-583.
139. Sharma, U.; Sood, S.; Sharma, N.; Rahi, P.; Kumar, R.; Sinha, A.; Gulati, A. Synthesis and SAR investigation of natural phenylpropene-derived methoxylated cinnamaldehydes and their novel Schiff bases as potent antimicrobial and antioxidant agents. Med. Chem. Res. 2013, 22, 5129-5140.
140. Cheng, S.-S.; Liu, J.-Y.; Tsai, K.-H.; Chen, W.-J.; Chang, S.-T. Chemical composition and mosquito larvicidal activity of essential oils from leaves of different Cinnamomum osmophloeum provenances. J. Agric. Food Chem. 2004, 52, 4395-4400.
141. Caredda, A.; Marongiu, B.; Porcedda, S.; Soro, C. Supercritical carbon dioxide extraction and characterization of Laurus nobilis essential oil. J. Agric. Food Chem. 2002, 50, 1492-1496.
142. Simić, A.; Soković, M.; Ristić, M.; Grujić-Jovanović, S.; Vukojević, J.; Marin, P. The chemical composition of some Lauraceae essential oils and their antifungal activities. Phytother. Res. 2004, 18, 713-717.
143. Koga, T.; Matsuse, I.; Teramoto, Y.; Ueda, S. Synthesis and antimycotic activity of cinnamyl benzoate. J. Ferment. Bioengineer. 1993, 76, 524-526.
144. Aziz, A.N.; Ibrahim, H.; Rosmy Syamsir, D.; Mohtar, M.; Vejayan, J.; Awang, K. Antimicrobial compounds from Alpinia conchigera. J. Ethnopharmacol. 2013, 145, 798-802.
145. Roy, S.K.; Pahwa, S.; Nandanwar, H.; Jachak, S.M. Phenylpropanoids of Alpinia galanga as efflux pump inhibitors in Mycobacterium smegmatis mc2 155. Fitoterapia 2012, 83, 1248-1255.
146. Jiang, Z.; Jiang, H.; Xie, P. Antifungal activities against Sclerotinia sclerotiorum by Cinnamomum cassia oil and its main components. J. Essent. Oil Res. 2013, 25, 444-451.
147. Mehta, G.; Singh, V. Hybrid systems through natural product leads: An approach towards new molecular entities. Chem. Soc. Rev. 2002, 31, 324-334.
148. Meunier, B. Hybrid molecules with a dual mode of action: Dream or reality? Acc. Chem. Res. 2008, 41, 69-77.
149. Wang, L.-J.; Geng, C.-A.; Ma, Y.-B.; Luo, J.; Huang, X.-Y.; Chen, H.; Zhou, N.-J.; Zhang, X.-M.; Chen, J.-J. Design, synthesis, and molecular hybrids of caudatin and cinnamic acids as novel anti-hepatitis B virus agents. Eur. J. Med. Chem. 2012, 54, 352-365.
150. Voisin-Chiret, A.S.; Bazin, M.-A.; Lancelot, J.-C.; Rault, S. Synthesis of new L-ascorbic ferulic acid hybrids. Molecules 2007, 12, 2533-2545.
151. Teixeira, J.; Silva, T.; Benfeito, S.; Gaspar, A.; Garrido, E.M.; Garrido, J.; Borges, F. Exploring nature profits: Development of novel and potent lipophilic antioxidants based on galloyl-cinnamic hybrids. Eur. J. Med. Chem. 2013, 62, 289-296.
152. Pérez, B.; Teixeira, C.; Gut, J.; Rosenthal, P.J.; Gomes, J.R.B.; Gomes, P. Cinnamic acid/chloroquinoline conjugates as potent agents against chloroquine-resistant Plasmodium falciparum. ChemMedChem 2012, 7, 1537-1540.
153. Pérez, B.C.; Teixeira, C.; Figueiras, M.; Gut, J.; Rosenthal, P.J.; Gomes, J.R.B.; Gomes, P. Novel cinnamic acid/4-aminoquinoline conjugates bearing non-proteinogenic amino acids: Towards the development of potential dual action antimalarials. Eur. J. Med. Chem. 2012, 54, 887-899.
154. Springer, D.M.; Luh, B.-Y.; Goodrich, J.; Bronson, J.J. Anti-MRSA cephems. Part 2: C-7 cinnamic acid derivatives. Bioorg. Med. Chem. 2003, 11, 265-279.
155. Michalska, K.; Karpiuk, I.; Król, M.; Tyski, S. Recent development of potent analogues of oxazolidinone antibacterial agents. Bioorg. Med. Chem. 2013, 21, 577-591.
156. Jasir, A.; Kasprzykowski, F.; Kasprzykowska, R.; Lindström, V.; Schalén, C.; Grubb, A. New antimicrobial cystatin C-based peptide active against gram-positive bacterial pathogens, including methicillin-resistant Staphylococcus aureus and multiresistant coagulase-negative staphylococci. Acta Pathol. Microbiol. Immunol. Scand. 2003, 111, 1004-1010.
157. Sato, K.; Shimizu, T.; Dimova, V.; Tomioka, H. Antimicrobial activities of cinnamyl rifamycin derivatives, T-9 and T-11, against Mycobacterium tuberculosis and Mycobacterium avium complex (MAC) with special reference to the activities against intracellular MAC. Microbiol. Immunol. 2006, 50, 621-623.
158. Velichka, D.; Ivana, A.; Haruaki, T.; Katsumasa, S.; Venkata, R.; Nadadhur, G.; Donna, D.; Todor, K.; Arvind, D.; Yurii, F.; et al. Experimental and clinical studies on Rifacinna-The new effective antituberculous drug (review). Recent Pat. Antiinfect. Drug Discover. 2010, 5, 76-90.
159. Reddy, V.M.; Nadadhur, G.; Daneluzzi, D.; Dimova, V.; Gangadharam, P.R. Antimycobacterial activity of a new rifamycin derivative, 3-(4-cinnamylpiperazinyl iminomethyl) rifamycin SV (T9). Antimicrob. Agents Chemother. 1995, 39, 2320-2324.
160. Dhople, A.M. Comparative In vitro activities of rifamycin analogues against Mycobacterium leprae. Indian J. Lepr. 1997, 69, 377-384.
161. De, P.; Koumba Yoya, G.; Constant, P.; Bedos-Belval, F.; Duran, H.; Saffon, N.; Daffé, M.; Baltas, M. Design, synthesis, and biological evaluation of new cinnamic derivatives as antituberculosis agents. J. Med. Chem. 2011, 54, 1449-1461.
162. TBAlliance. Isoniazid. Tuberculosis 2008, 88, 112-116.
163. TBAlliance. Cycloserine. Tuberculosis 2008, 88, 100-101.
164. Bairwa, R.; Kakwani, M.; Tawari, N.R.; Lalchandani, J.; Ray, M.K.; Rajan, M.G. R.; Degani, M.S. Novel molecular hybrids of cinnamic acids and guanylhydrazones as potential antitubercular agents. Bioorg. Med. Chem. Lett. 2010, 20, 1623-1625.
165. Slavchev, I.; Dobrikov, G.M.; Valcheva, V.; Ugrinova, I.; Pasheva, E.; Dimitrov, V. Antimycobacterial activity generated by the amide coupling of (-)-fenchone derived aminoalcohol with cinnamic acids and analogues. Bioorg. Med. Chem. Lett. 2014, in press.
166. Tanachatchairatana, T.; Bremner, J.B.; Chokchaisiri, R.; Suksamrarn, A. Antimycobacterial activity of cinnamate-based esters of the triterpenes betulinic, oleanolic and ursolic acids. Chem. Pharm. Bull. 2008, 56, 194-198.