Acide rosmarinique

==Nom de la substance==
Acide rosmarinique, "tanin des labiées"
==Famille moléculaire==
Acide phénol dérivé de l'acide cinnamique (polyphénol)
* Existe sous forme d'isomères cis et trans (l'isomère trans de l’acide rosmarinique est l'isomère naturel, exposé à la lumière du jour, il se transforme en isomère cis)
** Sa biosynthèse démarre des acides aminés L-phénylalanine et L-tyrosine
** Métabolisé au niveau du foie en acide férulique, acide caféique et acide coumarique 
* L'acide rosmarinique est un composé polaire, soluble dans les solvants polaires comme l’eau et l’éthanol
* Bien absorbé par le tractus gastro-intestinal et par la peau
==Source végétale==
* Romarin, mélisse, sauges, basilic, menthes, périlla, orthosiphon, lavandes, consoude, sarriette, marrube, hysope, monarde, lycope, origan, brunelle, nombreuses plantes de la famille des Lamiaceae surtout Lamaison JL, Petitjean-Freytet C, Carnat A. Lamiacées médicinales à propriétés antioxydantes, sources potentielles d'acide rosmarinique [Medicinal Lamiaceae with antioxidant properties, a potential source of rosmarinic acid]. Pharm Acta Helv. 1991;66(7):185-8. French. PMID 1763093., de Boraginaceae et d'Apiaceae, Thunbergia laurifolia Lindl. (Acanthaceae)
==Propriétés==
* Anti-oxydant puissant Zheng W, Wang SY. Antioxidant activity and phenolic compounds in selected herbs. J Agric Food Chem. 2001 Nov;49(11):5165-70. PMID 11714298, Adomako-Bonsu AG, Chan SL, Pratten M, Fry JR. Antioxidant activity of rosmarinic acid and its principal metabolites in chemical and cellular systems: Importance of physico-chemical characteristics. Toxicol In Vitro. 2017 Apr;40:248-255. doi: 10.1016/j.tiv.2017.01.016. PMID 28122265, Nunes S, Madureira AR, Campos D, Sarmento B, Gomes AM, Pintado M, Reis F. Therapeutic and nutraceutical potential of rosmarinic acid-Cytoprotective properties and pharmacokinetic profile. Crit Rev Food Sci Nutr. 2017 Jun 13;57(9):1799-1806. doi: 10.1080/10408398.2015.1006768. PMID 26114303, supérieur à la vitamine E , l’activité anti-oxydante de l’acide rosmarinique est due à la présence de quatre groupes hydroxyles dans sa molécule Alicia Caniova, Eva Brandsteterova. HPLC analysis of phenolic acids in Melissa officinalis. Journal of Liquid Chromatography & Related Technologies, Volume 24, Issue 17, 2001, pp 2647-2659 DOI:10.1081/JLC-100106092
* Antiviral (herpès HSV-1) Ansari M, Sharififar F, Arabzadeh AM, Mehni F, Mirtadzadini M, Iranmanesh Z, Nikpour N. In vitro evaluation of anti-herpes simplex-1 activity of three standardized medicinal plants from Lamiaceae. Anc Sci Life. 2014 Jul-Sep;34(1):33-8. doi: 10.4103/0257-7941.150777. PMID 25737608 (virus de l'encéphalite japonaise) Swarup V, Ghosh J, Ghosh S, Saxena A, Basu A. Antiviral and anti-inflammatory effects of rosmarinic acid in an experimental murine model of Japanese encephalitis. Antimicrob Agents Chemother. 2007 Sep;51(9):3367-70. PMID 17576830 texte intégral
* Antibactérien Petersen M, Simmonds MS. Rosmarinic acid. Phytochemistry. 2003 Jan;62(2):121-5. PMID 12482446, potentialise l'activité des antibiotiques vis-à-vis de Staphylococcus aureus résistant à la vancomycine Ekambaram SP, Perumal SS, Balakrishnan A, Marappan N, Gajendran SS, Viswanathan V. Antibacterial synergy between rosmarinic acid and antibiotics against methicillin-resistant Staphylococcus aureus. J Intercult Ethnopharmacol. 2016 Sep 21;5(4):358-363. doi: 10.5455/jice.20160906035020. PMID 27757265; PMCID: PMC5061478., Ekambaram, Sanmugapriya & M, Nathiya & V, Vinodhini & G, Sabari & B., Ajay. (2015). Synergistic effect of rosmarinic acid with antibiotics against Staphylococcus aureus and MRSA.. Chinese Journal of Pharmacology and Toxicology. 29. 58.
* Anti-asthénique
* Anti-inflammatoire Rocha J, Eduardo-Figueira M, Barateiro A, Fernandes A, Brites D, Bronze R, Duarte CM, Serra AT, Pinto R, Freitas M, Fernandes E, Silva-Lima B, Mota-Filipe H, Sepodes B. Anti-inflammatory effect of rosmarinic acid and an extract of Rosmarinus officinalis in rat models of local and systemic inflammation. Basic Clin Pharmacol Toxicol. 2015 May;116(5):398-413. doi: 10.1111/bcpt.12335. PMID 25287116., Wendy Pearson, Ronald S Fletcher, Laima S Kott, Mark B Hurtig. Protection against LPS-induced cartilage inflammation and degradation provided by a biological extract of Mentha spicata. BMC Complementary and Alternative Medicine. May 2010 , Colica, C., Di Renzo, L., Aiello, V., De Lorenzo, A., & Abenavoli, L. (2018). Rosmarinic acid as potential anti-inflammatory agent. Reviews on Recent Clinical Trials, 13(4), 240-242.pdf, augmente la production de prostaglandine E2 et réduit la production de leucotriène B4 dans les polynucléaires
* Antalgique Lucarini R, Bernardes WA, Ferreira DS, Tozatti MG, Furtado R, Bastos JK, Pauletti PM, Januário AH, Silva ML, Cunha WR. In vivo analgesic and anti-inflammatory activities of Rosmarinus officinalis aqueous extracts, rosmarinic acid and its acetyl ester derivative. Pharm Biol. 2013 Sep;51(9):1087-90. doi: 10.3109/13880209.2013.776613. PMID 23738822., intérêt dans les douleurs neuropathiques Ghasemzadeh Rahbardar M, Amin B, Mehri S, Mirnajafi-Zadeh SJ, Hosseinzadeh H. Anti-inflammatory effects of ethanolic extract of Rosmarinus officinalis L. and rosmarinic acid in a rat model of neuropathic pain. Biomed Pharmacother. 2017 Feb;86:441-449. doi: 10.1016/j.biopha.2016.12.049. PMID 28012923., Rahbardar MG, Amin B, Mehri S, Mirnajafi-Zadeh SJ, Hosseinzadeh H. Rosmarinic acid attenuates development and existing pain in a rat model of neuropathic pain: An evidence of anti-oxidative and anti-inflammatory effects. Phytomedicine. 2018 Feb 1;40:59-67. doi: 10.1016/j.phymed.2018.01.001. PMID 29496176., Boonyarikpunchai W, Sukrong S, Towiwat P. Antinociceptive and anti-inflammatory effects of rosmarinic acid isolated from Thunbergia laurifolia Lindl. Pharmacol Biochem Behav. 2014 Sep;124:67-73. doi: 10.1016/j.pbb.2014.05.004. PMID 24836183., Ghasemzadeh MR, Amin B, Mehri S, Mirnajafi-Zadeh SJ, Hosseinzadeh H. Effect of alcoholic extract of aerial parts of Rosmarinus officinalis L. on pain, inflammation and apoptosis induced by chronic constriction injury (CCI) model of neuropathic pain in rats. J Ethnopharmacol. 2016 Dec 24;194:117-130. doi: 10.1016/j.jep.2016.08.043. PMID 27566199.
* L'effet antalgique est comparable à celui du piroxicam Moradi Mohsen, Mashhadi Akbar Boojar Mahdi, Saberi Mehdi, Rahimi Salkuyeh Hamidreza, Ghorbani Maryam, Amanpour Hasan, Salem Fateme. Comparison of Analgesic Effect of Rosmarinic Acid With Piroxicam in Mice. Int J Basic Sci Med 2022/3/31;7(1):28-33. https://ijbsm.zbmu.ac.ir/PDF/ijbsm-23575
* Inhibe le système du complément
* Anti-allergique Takano H, Osakabe N, Sanbongi C, Yanagisawa R, Inoue K, Yasuda A, Natsume M, Baba S, Ichiishi E, Yoshikawa T. Extract of Perilla frutescens enriched for rosmarinic acid, a polyphenolic phytochemical, inhibits seasonal allergic rhinoconjunctivitis in humans. Exp Biol Med (Maywood). 2004 Mar;229(3):247-54. PMID 14988517, Makino T, Furuta Y, Wakushima H, Fujii H, Saito K, Kano Y. Anti-allergic effect of Perilla frutescens and its active constituents. Phytother Res. 2003 Mar;17(3):240-3. PMID 12672153, Sanbongi C, Takano H, Osakabe N, Sasa N, Natsume M, Yanagisawa R, Inoue KI, Sadakane K, Ichinose T, Yoshikawa T. Rosmarinic acid in perilla extract inhibits allergic inflammation induced by mite allergen, in a mouse model. Clin Exp Allergy. 2004 Jun;34(6):971-7. PMID 15196288, Osakabe N, Takano H, Sanbongi C, Yasuda A, Yanagisawa R, Inoue K, Yoshikawa T. Anti-inflammatory and anti-allergic effect of rosmarinic acid (RA); inhibition of seasonal allergic rhinoconjunctivitis (SAR) and its mechanism. Biofactors. 2004;21(1-4):127-31. PMID 15630183
* Hépatoprotecteur Osakabe N, Yasuda A, Natsume M, Sanbongi C, Kato Y, Osawa T, Yoshikawa T. Rosmarinic acid, a major polyphenolic component of Perilla frutescens, reduces lipopolysaccharide (LPS)-induced liver injury in D-galactosamine (D-GalN)-sensitized mice. Free Radic Biol Med. 2002 Sep 15;33(6):798-806. PMID 12208367
* Néphroprotecteur, atténue la néphrotoxicité induite par le cadmium Joardar S, Dewanjee S, Bhowmick S, Dua TK, Das S, Saha A, De Feo V. Rosmarinic Acid Attenuates Cadmium-Induced Nephrotoxicity via Inhibition of Oxidative Stress, Apoptosis, Inflammation and Fibrosis. Int J Mol Sci. 2019 Apr 24;20(8):2027. doi: 10.3390/ijms20082027. PMID 31022990 PMCID: PMC6514581
* Atténue la fibrose pulmonaire induite par la radiothérapie thoracique Zhang T, Ma S, Liu C, Hu K, Xu M, Wang R. Rosmarinic Acid Prevents Radiation-Induced Pulmonary Fibrosis Through Attenuation of ROS/MYPT1/TGFβ1 Signaling Via miR-19b-3p. Dose Response. 2020 Oct 19;18(4):1559325820968413. doi: 10.1177/1559325820968413. PMID 33149731; PMCID: PMC7580151.
* Neuroprotecteur par activation de Nrf2/HO-1, et inhibition de la voie NF-κB Ma Z, Lu Y, Yang F, Li S, He X, Gao Y, Zhang G, Ren E, Wang Y, Kang X. Rosmarinic acid exerts a neuroprotective effect on spinal cord injury by suppressing oxidative stress and inflammation via modulating the Nrf2/HO-1 and TLR4/NF-κB pathways. Toxicol Appl Pharmacol. 2020 Apr 19;397:115014. doi: 10.1016/j.taap.2020.115014. PMID 32320792.
* Potentialités dans la maladie d'Alzheimer, activité anticholinestérasique Dastmalchi K, Ollilainen V, Lackman P, Boije af Gennäs G, Dorman HJ, Järvinen PP, Yli-Kauhaluoma J, Hiltunen R. Acetylcholinesterase inhibitory guided fractionation of Melissa officinalis L. Bioorg Med Chem. 2009 Jan 15;17(2):867-71. PMID 19070498
* Anticarcinogène Osakabe N, Yasuda A, Natsume M, Yoshikawa T. Rosmarinic acid inhibits epidermal inflammatory responses: anticarcinogenic effect of Perilla frutescens extract in the murine two-stage skin model. Carcinogenesis. 2004 Apr;25(4):549-57. PMID 14729597, inhibe le développement des métastases de cancer du sein Xu Y, Jiang Z, Ji G, Liu J. Inhibition of Bone Metastasis from Breast Carcinoma by Rosmarinic Acid. Planta Med 2010; 76: 956–962
==Effet thérapeutique==
* Prévention des cancers, viroses, maladies inflammatoires et allergiques
==Effets indésirables==
==Bibliographie==
* Gábor Janicsák, Imre Máthé, Vilmos Miklóssy-Vári, Gerald Blunden. Comparative studies of the rosmarinic and caffeic acid contents of Lamiaceae species. Biochemical Systematics and Ecology, Volume 27, Issue 7, 1999, Pages 733-738, https://doi.org/10.1016/S0305-1978(99)00007-1.
* Al-Dhabi, N. A., Arasu, M. V., Park, C. H., & Park, S. U. (2014). Recent studies on rosmarinic acid and its biological and pharmacological activities. EXCLI journal, 13, 1192.
* Christine M. Kaefer and John A. Milner. The Role of Herbs and Spices in Cancer Prevention. J Nutr Biochem. 2008 June; 19(6): 347–361. http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2771684/pdf/nihms53681.pdf/?tool=pmcentrez
* H. Bult, A. G. Herman, and M. Rampart. Modification of endotoxin-induced haemodynamic and haematological changes in the rabbit by methylprednisolone, F(ab')2 fragments and rosmarinic acid. Br J Pharmacol. 1985 February; 84(2): 317–327.
* Nakatani N. Phenolic antioxidants from herbs and spices. Biofactors. 2000;13(1-4):141-6. PMID 11237173
* Alica Ziaková, Eva Brandsˇteterová. Application of different preparation techniques for extraction of phenolic antioxidants from lemon balm (Melissa officinalis ) before HPLC analysis. Journal of Liquid Chromatography & Related Technologies, Volume 25, Issue 19, 2002, pp 3017-3032 DOI:10.1081/JLC-120015888
* Penchev Petko Ivanov. Étude des procédés d’extraction et de purification de produits bioactifs à partir de plantes par couplage de techniques séparatives à basses et hautes pressions. Thèse de Doctorat de l’Université de Toulouse (Génie des Procédés et de l'Environnement), juillet 2010
Catégorie:Principes actifs