Phenolic compounds of laurus nobilis (review)
https://doi.org/10.19163/2307-9266-2019-7-5-244-259
Abstract
One of the most famous plants of the laurel family (Lauraceae) is Laurus nobilis L.
The aim of the study was to review scientific information on the study of phenolic compounds of wild-growing and cultivated Laurus nobilis L.
Materials and methods. The study was performed using information retrieval (PubMed, ScholarGoogle) and library databases (eLibrary, Cyberleninca), as well as ResearchGate application for semantic search. The research methods are analysis and synthesis of the scientific literature data for the period from 2000 up to the present.
Results. The data presented in the review show that leaves, fruits, and shoots of Laurus nobilis L. are valuable sources of phenolic compounds, such as phenolic acids, flavonoids, and proanthocyanidins. The quantitative content of these groups of substances varies depending on the collecting ground, the source of raw materials (cultivated or wild plants), the time (phase) of their harvesting, the method of drying, extraction from raw materials, etc. Phenolic compounds exhibit a pronounced antioxidant and antiradical activity, have an inhibitory effect on NO production, sodium-potassium adenosine triphosphatase, on tumour cell lines (HeLa, MCF7, NCI-H460 and HCT15), and are characterised by an antibacterial action against gram-positive and gram-negative bacteria.
Conclusion. The analysis of the available scientific information showed that the phenolic compounds of Laurus nobilis L. are one of the main groups of the active compounds of this plant. The use of this information is essential for the development of new effective medicines based on the raw materials of Laurus nobilis L..
About the Authors
D. A. Konovalov
Pyatigorsk Medical and Pharmaceutical Institute – branch of Volgograd State Medical University
Russian Federation
Russian Federation
Dmitry A. Konovalov - Doctor of Science (Phamacy), Professor, Head of Department of Pharmacognosy, Botany and Technology of Phytopreparation.
11, Kalinin ave., Pyatigorsk, Stavropol region, 357532.
Researcher ID: B-7017-2017
Scopus Author ID: 56436041900
N. M. Alieva
Dagestan State Medical University
Russian Federation
Russian Federation
Naida M. Alieva - Senior Lecturer, Department of Normal Physiology.
1, Lenin sq., Makhachkala, Dagestan republic, 367000.
References
1. Marzouki H, Piras A, Salah KBH, Medini H, Pivetta T, Bouzid S, Falconieri D. Essential oil composition and variability of Laurus nobilis L. growing in Tunisia, comparison and chemometric investigation of different plant organs. Natural product research. 2009;23(4):343-54.
2. Barla A, Topcu G, Oksuz S, Tumen G, Kingston DGI. Identi-fication of cytotoxic sesquiterpenes from Laurus nobilis L. Food Chemistry. 2007;104(4):1478-84.
3. Fang F, Sang S, Chen KY, Gosslau A, Ho CT, Rosen RT. Iso¬lation and identification of cytotoxic compounds from Bay leaf (Laurus nobilis). Food Chemistry. 2005;93(3):497-501.
4. Ivanoic J, Misin D, Ristic M, Pesic O, Zizovic I. Supercritical CO2 extract and essential oil of bay (Laurus nobilis L.) - chemical composition and antibacterial activity. Journal of the Serbian Chemical Society. 2010; 75:395-404.
5. Ouchikh O, Chahed T, Ksouri R, Taarit MB, Faleh H, Abdelly C, Kchouk ME, Marzouk B. The effects of extraction method on the measured tocopherol level and antioxidant activity of L. nobilis vegetative organs. Journal of Food Composition and Analysis. 2011;24:103-10.
6. Conforti F, Statti G, Uzunov D, Menichinia F. Comparative chemical composition and antioxidant activities of wild and cultivated Laurus nobilis L. Leaves and Foeniculum vulgare subsp. piperitum (Ucria) Coutinho Seeds. Biological & Pharmaceutical Bulletin. 2006;29:2056-64.
7. Ozcan B, Esen M, Sangun MK, Coleri A, Caliskan M. Effective antibacterial and antioxidant properties of methanolic extract of Laurus nobilis seed oil. Journal of Environmental Biology. 2010;31:637-41.
8. Polovka M, Suhaj M. Detection of caraway and bay leaves irradiation based on their extracts antioxidant properties evaluation. Food Chemistry. 2010;119:391-401.
9. Speroni E, Cervellati R, Dall'Acqua S, Guerra MC, Greco E, Govoni P, Innocenti G. Gastroprotective effect and antioxidant properties of different Laurus nobilis L. leaf extracts. Journal of Medicinal Food. 2011;14:499-504.
10. Ramos C, Teixeira B, Batista I, Matos O, Serrano C, Neng NR, Nogueira, JMF, Nunes ML, Marques M. Antioxidant and antibacterial activity of essential oil and extracts of bay leave Laurus nobilis Linnaeus (Lauraceae) from Portugal. Natural Product Research. 2012;6:518-529.
11. Dall'Acqua S, Cervellati R, Speroni E, Costa S, Guerra MC, Stella L, Greco E, Innocenti G. Phytochemical composition and antioxidant activity of Laurus nobilis L. leaf infusion. Journal of Medicinal Food. 2009;12:869-76.
12. Ghannadi A. Lauri Folium. In: "Iranian Herbal Pharmacopoeia". Tehran: Publications of Iranian Ministry of Health. 2002.
13. Ramling P, Meera M, Priyanka P. Phytochemical and Phar-macological Review on Laurus Nobilis. Int J of Pharm and Chem Sci. 2012;1(2):595-602.
14. Esra K, Ilkay O, Erdem Y. Evaluation of Some Plants Used in Turkish Folk Medicine for Their Anti-inflammatory and An-tinociceptive Activities. Pharmac Biol. 2007;45(7):547-55.
15. Bilen S, Bulut M. Effect of Laurel (Laurus nobilis) on the non-Specific immune responses of rainbow trout (Oncorhynchus mykiss, Walbaum). J of Animal and Veterinary Advances. 2010;9(8):1275-7.
16. Shin J, Oh K, Lee S, Nam K, Koo U, Kim KH, Mar W. Neuroprotective Effect of the n-Hexane Extracts of Laurus nobilis L. in Models of Parkinson's Disease. Biomol Ther. 30. 2011;19(1):118-25.
17. Essential Oil of Laurus nobilis L. from Iran. Iranian Journal of Pharmaceutical Sciences. Iranian J of Pharmac Sci. 2009;5(1):47-50.
18. Saab AM, Tundis R, Loizzo MR, Lampronti I, Borgatti M, Gambari R, Menichini F, Esseily F, Menichini F. Antioxidant and antiproliferative activity of Laurus nobilis L. (Lauraceae) leaves and seeds essential oils against K562 human chronic myelogenous leukaemia cells. Natural Product Research. 2012;26:1741-5.
19. Kaileh M, Berghe WV, Boone E, Essawi T, Haegeman G. Screening of indigenous Palestinian medicinal plants for potential anti-inflammatory and cytotoxic activity. Journal of Ethnopharmacology. 2007;113(3):510-6.
20. Al-Kalaldeh JZ, Abu-Dahab R. Afifi FU. Volatile oil com¬position and antiproliferative activity of Laurus nobilis, - Origanum syriacum, Origanum vulgare, and Salvia triloba against human breast adenocarcinoma cells. Nutrition Research. 2010;30(4):271-8.
21. de Corato U, Maccioni O, Trupo M, Di Sanzo G. Use of essential oil of Laurus nobilis obtained by means of a supercritical carbon dioxide technique against post harvest spoilage fungi. Crop Protection. 2010;29(2):142-7.
22. Millezi AF, Caixeta DS, Rossoni DF, Cardoso MG, Piccoli RG. In vitro antimicrobial properties of plant essential oils Thymus vulgaris, Cymbopogon citratus and Laurus nobilis against five important foodborne pathogens. Ciencia e Tecnologia de Alimentos. 2012;32:167-72.
23. Adwan G, Mhanna M. Synergistic effects of plant extracts and antibiotics on Staphylococcus aureus strains isolated from clinical specimens. Middle-East Journal of Scientific Research. 2008;3:134-9.
24. Al-Hussaini R, Mahasneh AM. Microbial growth and quorum sensing antagonist activities of herbal plants extracts. Molecules. 2009;14(9):3425-35.
25. Fukuyama N, Ino C, Suzuki Y, Kobayashi N, Hamamoto H, Sekimizu K, Orihara Y. Antimicrobial sesquiterpenoids from Laurus nobilis L. Natural Product Research. 2011;25(14):1295-303.
26. Otsuka N, Liu MH, Shiota S, et al. Anti-methicillin resistant Staphylococcus aureus (MRSA) compounds isolated from Laurus nobilis. Biological and Pharmaceutical Bulletin. 2008;31(9):1794-7.
27. Liu MH, Otsuka N, Noyori K, et al. Synergistic effect of kaempferol glycosides purified from Laurus nobilis and fluoroquinolones on methicillin-resistant Staphylococcus aureus. Biological and Pharmaceutical Bulletin. 2009;32, (3):489-92.
28. Ogay MA, Stepanova EF. Razrabotka i issledovaniye gipoglikemicheskogo fitosbora [Development and research of a hypoglycemic phytosborne]. Bulletin of the Voronezh State University. Series: Chemistry. Biology. Pharmacy. 2006;2:332-3.Russian.
29. Ogay MA, Stepanova EF, Larionov LP, Petrov AYu. Farmakologicheskiye issledovaniya i tekhnologiya fitogeley dlya korrektsii posledstviy sakharnogo diabeta [Pharmacological research and phytogel technology for the correction of diabetes mellitus]. Bulletin of Voronezh State University. Series: Chemistry. Biology. Pharmacy. 2009;2:171-3. Russian.
30. Pat. 2071783 Russia, MKI 6 A 61 K 35/78. Sposob polucheniya sredstva dlya lecheniya sakharnogo diabeta [A method of obtaining funds for the treatment of diabetes]. Babyakin F, Naydanova LF, Mazurov VI, Ruzhenkov DV, Kirichenko NN. No. 93044820/14; Claim 09/07/93; Publ. 01/20/97, Bull. Number 2. Russian.
31. Pat. 2176895 Russia, IPC: 7A 23L 1/30 A, 7A 61K 35/78 B.32. Biologicheski aktivnaya pishchevaya dobavka i sposob povysheniya umstvennoy i fizicheskoy rabotosposobnosti cheloveka [Dietary supplement and method of increasing mental and physical health of a person]. Smirnov VM. Date of registration: 11.22.1999. Application Number: 99124708/13.
32. Diaaz-Maroto M; Rez-Coello M; Cabezudo M. Effect of drying method on the volatiles in bay leaf (Laurus nobilis L.). J Agric Food Chem. 2002;50:4520-4.
33. Nasukhova NM, Konovalov DA. Dinamika nakopleniya efirnogo masla v list'yakh lavra blagorodnogo [The dynamics of the accumulation of essential oil in the leaves of laurel noble]. Bulletin of the Volgograd State Medical University. 2014;S:94-5.
34. Konovalov DA, Nasuhova NM. Sesquiterpene lactones of leaves and fruits of Laurus nobilis L. Pharmacy & Pharmacology. 2014;2(2(3)):23-33. Russian. https://doi.org/10.19163/2307-9266-2014-2-2(3)-23-33
35. El-Feraly S; Benigni D. Sesquiterpene lactones of Laurus nobilis leaves. J Nat Prod. 1980;43:527-31.
36. Matsuda H; Kagerura T; Toguchida I; Ueda H; Morikawa T; Yoshikawa M. Inhibitory Effects of sesquiterpene from Bay leaf on nitric oxide production in lipopolysaccharide-activated macrophages: structure requirement and role of heat shock protein induction. Life Sci. 2000;66:2151-7.
37. Senchenko SP, Nasuhova NM, Agova LA, Konovalov DA. Using HPLC and capillary electrophoresis for quantifying costunolide and dehydrocostuslatone in Laurel leaves. Bulletin of the Volgograd State Medical University. 2014;4(52):18-20. Russian.
38. Yoshikawa M,Shimoda H, Uemura T, Morikawa T, Kawahara Y, Matsuda H. Alcohol absorption inhibitors from Bay leaf (Laurus nobilis): Structure-requirements of sesquiterpenes for the activity. Bioorg. Med. Chem. 2000;8:2071-7.
39. Rasul A, Parveen S, Ma T. Costunolide: A novel anti-cancer sesquiterpene lactone. Bangladesh Journal of Pharmacology.2012;7(1):6-13.
40. Lin X, Peng Z, Su C. Potential anti-cancer activities and mechanisms of costunolide and dehydrocostuslactone. International journal of molecular sciences. 2015;16(5):10888-906.
41. Emam AM, Mohamed MA, Diab YM, Megally NY. Isolation and structure elucidation of antioxidant compounds from leaves of Laurus nobilis and Emex spinosus. Drug Discoveries & Therapeutics. 2010;4:202-207.
42. Kaurinovic B, Popovic M, Vlaisavljevic S. In vitro and in vivo effects of Laurus nobilis L. leaf extracts. Molecules. 2010;15:3378-90.
43. Nesterova OV, Dobrokhotov DA, Didmanidze IO. Analysis of phytochemical features and some of the quality index¬es of Laurus nobilis leaves. Questions of quality of medicines. 2015;1(6):23-30. Russian.
44. Kang Yu KW, Jun WJ, Chang IS, Han SB, Kim HY, Cho HY. Iso-lation and characterization of alkyl peroxy radical scavenging compound from leaves of Laurus nobilis. Biol Pharm Bull. 2002;25(1):102-8.
45. de Marino S, Borbone N, Zollo F, Ianaro A, Di Meglio P, Iorizzi M. Megastigmane and Phenolic Components from Laurus nobilis L. Leaves and Their Inhibitory Effects on Nitric Oxide Production. J Agric Food Chem. 2004;52:7525-31.
46. Skerget M, Kotnik P, Hadolin M, Hras AR, Simonic M, & Knez Z. Phenols, proanthocyanidins, flavones and flavonols in some plant materials and their antioxidant activities. Food chemistry. 2005;89(2):191-8.
47. Longo L, Vasapollo G. Anthocyanins from bay (Laurus nobilis L.) berries. Journal of agricultural and food chemistry. 2005;53(20), 8063-7.
48. Papageorgiou V, Mallouchos A, Komaitis M. Investigation of the Antioxidant Behavior of Air- and Freeze-Dried Aro¬matic Plant Materials in Relation to Their Phenolic Content and Vegetative Cycle. J Agric Food Chem. 2008;56:5743-52.
49. Singleton VL, Rossi JA. Colorimetry of total phenolics with phosphomolybdic-phosphotungstic acid reagents. American journal of Enology and Viticulture. 1965;16(3):144-58.
50. Cannac M, Ferrat L, Barboni T, Pergent G, Pasqualini V. The influence of tissue handling on the flavonoid con¬tent of the aquatic plant Posidonia oceanic. J Chem Ecol. 2007;33:1083-8.
51. Moure A, Cruz JM, Franco D, Dominguez JM, Sineiro J, Dominguez H, Jose Nunez M, Parajo JC. Natural antioxidants from residuals sources. Food Chem. 2001;72:145-71.
52. Muchuweti M, Kativu E, Mupure CH, Chidewe C, Ndhlala AR, Benhura MAN. Phenolic composition and antioxidant properties of some spices. American Journal of Food Technology. 2007;2(5):414-20.
53. Unver A, Arslan D, Ozcan MM, Akbulut M. Phenolic con¬tent and antioxidant activity of some spices. World Applied Sciences Journal. 2009;6(3):373-7.
54. Lu M, Yuan B, Zeng M, Chen J. Antioxidant capacity and major phenolic compounds of spices commonly consumed in China. Food Research International. 2011;44(2):530-6.
55. Lee S, Chung SCh, Lee SH, Park W, Oh I, Mar W, Shin J, Oh KB. Acylated kaempferol glycosides from Laurus nobilis leaves and their inhibitory effects on Na+/K+-adenosine triphosphatase. Biol Pharm Bull. 2012;35(3):428-32.
56. Pacifico S, Gallicchio M, Lorenz P, Duckstein SM, Potenza N, Galasso S, Marciano S, Fiorentino A, Stintzing FC, Monaco P. Neuroprotective Potential of Laurus nobilis Antioxidant Polyphenol-Enriched Leaf Extracts. Chemical research in toxicology. 2014;27(4):611-26.
57. Dias MI, Barros L, Duenas M, Alves RC, Oliveira MBP, Santos-Buelga C, Ferreira IC. Nutritional and antioxidant contributions of Laurus nobilis L. leaves: would be more suitable a wild or a cultivated sample? Food chemistry. 2014;156:339-46.
58. Dias MI, Barreira J, Calhelha RC, Queiroz MJR, Oliveira MBPP, Sokovic M, Ferreira IC. Two-dimensional PCA high-lights the differentiated antitumor and antimicrobial activity of methanolic and aqueous extracts of Laurus nobilis L. from different origins. BioMed research international. 2014; 2014:10.
59. Muniz-Marquez DB, Marti'nez-Avila GC, Wong-Paz JE, Belmares-Cerda R, Rodriguez-Herrera R, Aguilar CN. Ultra-sound-assisted extraction of phenolic compounds from Laurus nobilis L. and their antioxidant activity. Ultrasonics sonochemistry. 2013;20(5):1149-54.
60. Musienko SG, Kyslychenko VS. The quantitative content of the main groups of biologically active substances in the bay laurel raw material. Pharmacy Bulletin. 2014;4(80):22-4. Ukrainian.
61. Musienko SH, Kyslychenko VS. Study of phenolic compounds of raw bay laurel. Collection of scientific works of NMAPE em. PL Shupik. 2014;23(4):341-344. Ukrainian.
62. Vinha AF, Guido LF, Costa AS, Alves RC, Oliveira MBP. Monomeric and oligomeric flavan-3-ols and antioxidant activity of leaves from different Laurus sp. Food & function. 2015;6(6):1944-1949.
Review
For citations:
Konovalov D.A., Alieva N.M. Phenolic compounds of laurus nobilis (review). Pharmacy & Pharmacology. 2019;7(5):244-259. https://doi.org/10.19163/2307-9266-2019-7-5-244-259
Views:
1667
Email this article 