The aim of this study was to analyze the effect of solutions containing saturated anacardic acid (AA) on dentine erosion in vitro. AA was chemically isolated from natural cashew nutshell liquid obtained by continuous extraction in a Soxhlet extractor and was fully saturated by catalytic hydrogenation. Matrix metalloproteinase 2 (MMP-2) activity, when exposed to buffers containing 100 µmol/l AA, was analyzed using zymography. Bovine root samples were subjected to erosive demineralization (Sprite Zero™, 4 × 90 s/day) and remineralization with artificial saliva between the erosive cycles for 5 days. The samples were treated as follows, after the first and the last acid exposure (1 min; n = 12/group): (1) 100 µmol/l epigallocatechin-3-gallate (EGCG) (positive control); (2) 0.05% NaF; (3) 100 µmol/l saturated AA; (4) saturated AA and EGCG; (5) saturated AA, EGCG and NaF; (6) untreated (negative control). Dentine erosion was measured using a contact profilometer. Two dentine samples from each group were analyzed using scanning electron microscopy. Saturated AA reduced the activity of MMP-2. ANOVA and Tukey's test revealed that all treatments significantly reduced dentine loss compared to the negative control (6.03 ± 0.98 µm). Solutions containing saturated AA (1.97 ± 1.02 µm) showed the greatest reduction in dentine erosion compared to the NaF (3.93 ± 1.54 µm) and EGCG (3.79 ± 0.83 µm) solutions. Therefore, it may be concluded that AA significantly reduces dentine erosion in vitro, possibly by acting as an MMP-2 inhibitor.

Keywords:
Anacardic acid, Dentine erosion, Epigallocatechin-3-gallate, Erosive tooth wear, Gelatinase, Matrix metalloproteinase
1.
Attin T: Methods for assessment of dental erosion. Monogr Oral Sci 2006;20:152-172.
2.
Attin T, Becker K, Roos M, Attin R, Paqué F: Impact of storage conditions on profilometry of eroded dental hard tissue. Clin Oral Investig 2009;13:473-478.
3.
Buzalaf MA, Kato MT, Hannas AR: The role of matrix metalloproteinases in dental erosion. Adv Dent Res 2012;24:72-76.
4.
Demeule M, Brossard M, Pagé M, Gingras D, Béliveau R: Matrix metalloproteinase inhibition by green tea catechins. Biochim Biophys Acta 2000;1478:51-60.
5.
dos Santos ML, de Magalhães GC: Utilisation of cashew nut shell liquid from Anacardium occidentale as starting material for organic synthesis: a novel route to lasiodiplodin from cardols. J Braz Chem Soc 1999;10:13-20.
6.
Gandhi T, Patel M, Dholakiya BK: Studies on effect of various solvents on extraction of cashew nut shell liquid (CNSL) and isolation of major phenolic constituents from extracted CNSL. J Nat Prod Plant Resour 2012;2:135-142.
7.
Ganss C: Definition of erosion and links to tooth wear. Monogr Oral Sci 2006;20:9-16.
8.
Ganss C, Lussi A, Scharmann I, Weigelt T, Hardt M, Klimek J, Schlueter N: Comparison of calcium analysis, longitudinal microradiography and profilometry for the quantitative assessment of erosion in dentine. Caries Res 2009;43:422-429.
9.
Ganss C, Neutard L, von Hinckeldey J, Klimek J, Schlueter N: Efficacy of a tin/fluoride rinse: a randomized in situ trial on erosion. J Dent Res 2010;89:1214-1218.
10.
Ganss C, Schlueter N, Hardt M, von Hinckeldey J, Klimek J: Effects of toothbrushing on eroded dentine. Eur J Oral Sci 2007;115:390-396.
11.
Hemshekhar M, Sebastin Santhosh M, Kemparaju K, Girish KS: Emerging roles of anacardic acid and its derivatives: a pharmacological overview. Basic Clin Pharmacol Toxicol 2012;110:122-132.
12.
Imfeld T: Dental erosion. Definition, classification and links. Eur J Oral Sci 1996;104:151-155.
13.
Kato MT, Leite AL, Hannas AR, Buzalaf MA: Gels containing MMP inhibitors prevent dental erosion in situ. J Dent Res 2010;89:468-472.
14.
Kato MT, Leite AL, Hannas AR, Calabria MP, Magalhães AC, Pereira JC, Buzalaf MA: Impact of protease inhibitors on dentin matrix degradation by collagenase. J Dent Res 2012;91:1119-1123.
15.
Kato MT, Magalhães AC, Rios D, Hannas AR, Attin T, Buzalaf MA: Protective effect of green tea on dentin erosion and abrasion. J Appl Oral Sci 2009;17:560-564.
16.
Klimek J, Hellwig E, Ahrens G: Fluoride taken up by plaque, by the underlying enamel and by clean enamel from the three fluoride compounds in vitro. Caries Res 1982;16:156-161.
17.
Kontogiorgis CA, Papaioannou P, Hadjipavlou-Litina DJ: Matrix metalloproteinase inhibitors: a review on pharmacophore mapping and (Q)SARs results. Curr Med Chem 2005;12:339-355.
18.
Kreulen CM, van't Spijker A, Rodriguez JM, Bronkhorst EM, Creugers NH, Bartlett DW: Systematic review of the prevalence of tooth wear in children and adolescents. Caries Res 2010;44:151-159.
19.
Logrado LP, Santos CO, Romeiro LA, Costa AM, Ferreira JR, Cavalcanti BC, Manoel de Moraes O, Costa-Lotufo LV, Pessoa C, Dos Santos ML: Synthesis and cytotoxicity screening of substituted isobenzofuranones designed from anacardic acids. Eur J Med Chem 2010;45:3480-3489.
20.
Magalhães AC, Levy FM, Rizzante FA, Rios D, Buzalaf MA: Effect of NaF and TiF(4) varnish and solution on bovine dentin erosion plus abrasion in vitro. Acta Odontol Scand 2012;70:160-164.
21.
Magalhães AC, Wiegand A, Rios D, Buzalaf MA, Lussi A: Fluoride in dental erosion. Monogr Oral Sci 2011;22:158-170.
22.
Magalhães AC, Wiegand A, Rios D, Hannas A, Attin T, Buzalaf MA: Chlorhexidine and green tea extract reduce dentin erosion and abrasion in situ. J Dent 2009;37:994-998.
23.
Meurman JH, Drysdale T, Frank RM: Experimental erosion of dentin. Scand J Dent Res 1991;99:457-462.
24.
Mjör IA: Pulp-dentin biology in restorative dentistry. Part 5: Clinical management and tissue changes associated with wear and trauma. Quintessence Int 2001;32:771-788.
25.
Omanakuttan A, Nambiar J, Harris RM, Bose C, Pandurangan N, Varghese RK, Kumar GB, Tainer JA, Banerji A, Perry JJ, Nair BG: Anacardic acid inhibits the catalytic activity of matrix metalloproteinase-2 and matrix metalloproteinase-9. Mol Pharmacol 2012;82:614-622.
26.
Paramashivappa R, Phani Kumar P, Subba Rao PV, Srinivasa Rao A: Synthesis of sildenafil analogues from anacardic acid and their phosphodiesterase-5 inhibition. J Agric Food Chem 2002;50:7709-7713.
27.
Schlueter N, Glatzki J, Klimek J, Ganss C: Erosive-abrasive tissue loss in dentine under simulated bulimic conditions. Arch Oral Biol 2012;57:1176-1182.
28.
Schlueter N, Hara A, Shellis RP, Ganss C: Methods for the measurement and characterization of erosion in enamel and dentine. Caries Res 2011;45:13-23.
29.
Sulkala M, Tervahartiala T, Sorsa T, Larmas M, Salo T, Tjäderhane L: Matrix metalloproteinase-8 (MMP-8) is the major collagenase in human dentin. Arch Oral Biol 2007;52:121-127.
30.
Sulkala M, Wahlgren J, Larmas M, Sorsa T, Teronen O, Salo T, Tjäderhane L: The effects of MMP inhibitors on human salivary MMP activity and caries progression in rats. J Dent Res 2001;80:1545-1549.
31.
Sullivan JT, Richards CS, Lloyd HA, Krishna G: Anacardic acid: molluscicide in cashew nut shell liquid. Planta Med 1982;44:175-177.
32.
Tjäderhane L, Larjava H, Sorsa T, Uitto VJ, Larmas M, Salo T: The activation and function of host matrix metalloproteinases in dentin matrix breakdown in caries lesions. J Dent Res 1998;77:1622-1629.
33.
Vempati RK, Srinivasa RA, Reddy NS, Naresh VV, Dubey PK: Synthesis of novel quinoline carboxylic acids from anacardic acid. Der Pharma Chemica 2012;4:248-254.
34.
Verma RP, Hansch C: Matrix metalloproteinases (MMPs): chemical-biological functions and (Q)SARs. Bioorg Med Chem 2007;15:2223-2268.
© 2014 S. Karger AG, Basel
2014
Copyright / Drug Dosage / Disclaimer
Copyright: All rights reserved. No part of this publication may be translated into other languages, reproduced or utilized in any form or by any means, electronic or mechanical, including photocopying, recording, microcopying, or by any information storage and retrieval system, without permission in writing from the publisher.
Drug Dosage: The authors and the publisher have exerted every effort to ensure that drug selection and dosage set forth in this text are in accord with current recommendations and practice at the time of publication. However, in view of ongoing research, changes in government regulations, and the constant flow of information relating to drug therapy and drug reactions, the reader is urged to check the package insert for each drug for any changes in indications and dosage and for added warnings and precautions. This is particularly important when the recommended agent is a new and/or infrequently employed drug.
Disclaimer: The statements, opinions and data contained in this publication are solely those of the individual authors and contributors and not of the publishers and the editor(s). The appearance of advertisements or/and product references in the publication is not a warranty, endorsement, or approval of the products or services advertised or of their effectiveness, quality or safety. The publisher and the editor(s) disclaim responsibility for any injury to persons or property resulting from any ideas, methods, instructions or products referred to in the content or advertisements.
You do not currently have access to this content.