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Development of an analytical method for the quantification of oleanonic acid from mastic gum using HPLC/PDA

  • Hak-Dong Lee (Department of Plant Science and Technology, Chung-Ang University) ;
  • Chang-Dae Lee (Department of Plant Science and Technology, Chung-Ang University) ;
  • So Yeon Choi (Vitalabs Co. Ltd.) ;
  • Sanghyun Lee (Department of Plant Science and Technology, Chung-Ang University)
  • Received : 2023.01.11
  • Accepted : 2023.02.05
  • Published : 2023.12.31

Abstract

A simple and accurate method was developed for the quantitative analysis of oleanonic acid (OA) from mastic gum. The analysis was carried out using reverse-phase high-performance liquid chromatography combined with a photodiode array detector (HPLC/PDA). Our optimized method was validated by measuring various parameters, using an INNO C18 column fitted with a gradient elution system. The results revealed limits of detection and quantification of 0.34 and 1.042 ㎍/mL, respectively. The OA calibration curve exhibited excellent linearity over the concentration range of 0.0625 to 2.0 mg/mL, with r2 =0.9996. Accuracy tests revealed a high recovery rate of 99.44-103.66%, with precision values below 0.15%. These results suggest that the present analytical method can identify and quantify OA in mastic gum with high precision. The HPLC approach developed in this study might be applied to routine analyses and large-scale extraction procedures for OA content quantification.

Keywords

Acknowledgement

This study was funded by a grant of Vitalabs Co. Ltd, Seoul, Republic of Korea.

References

  1. Lemonakis N, Magiatis P, Kostomitsopoulos N, Skaltsounis AL, Tamvakopoulos C (2011) Oral administration of Chios mastic gum or extracts in mice: Quantification of triterpenic acids by liquid chromatography-tandem mass spectrometry. Planta Med 77: 1916-1923. doi: 10.1055/s0031-1279996
  2. Paraschos S (2010) Phytochemical and pharmacological study of Chios mastic gum. National and Kapodistrian University of Athens. Athens, Greece
  3. Pachi VK, Mikropoulou EV, Gkiouvetidis P, Siafakas K, Argyropoulou A, Angelis A, Mitakou S, Halabalaki M (2020) Traditional uses, phytochemistry and pharmacology of Chios mastic gum (Pistacia lentiscus var. chia, Anacardiaceae): A review. J Ethnopharmacol 254: 112485. doi: 10.1016/j.jep.2019.112485
  4. Browicz K (1987) Pistacia lentiscus cv. Chia (Anacardiaceae) on Chios island. Plant Syst Evol 155: 189-195. doi: 10.1007/BF00936298
  5. Ierapetritis D (2010) The geography of the Chios mastic trade from the 17th through to the 19th century. Ethnobot Res Appl 8: 153-167
  6. Zacharopoulos C, Barbikas E (2008) Chios Mastiha Historic and Folkloric references. The Chios Mastiha Growers Association, Chios. 2-37
  7. Koutsoudaki C, Krsek M, Rodger A (2005) Chemical composition and antibacterial activity of the essential oil and the gum of Pistacia lentiscus var. chia. J Agric Food Chem 53: 7681-7685. doi: 10.1021/jf050639s
  8. Tabanca N, Nalbantsoy A, Kendra PE, Demirci F, Demirci B (2020) Chemical characterization and biological activity of the mastic gum essential oils of Pistacia lentiscus var. chia from Turkey. Molecules 25: 2136. doi: 10.3390/molecules25092136
  9. Andrikopoulos NK, Kaliora AC, Assimopoulou AN, Papapeorgiou VP (2003) Biological activity of some naturally occurring resins, gums and pigments against in vitro LDL oxidation. Phyther Res 17: 501-507
  10. Dedoussis GVZ, Kaliora AC, Psarras S, Chiou A, Mylona A, Papadopoulos NG, Andrikopoulos NK (2004) Antiatherogenic effect of Pistacia lentiscus via GSH restoration and downregulation of CD36 mRNA expression. Atherosclerosis 174: 293-303. doi: 10.1016/j.atherosclerosis.2004.02.011
  11. Janakat S, Al-Merie H (2002) Evaluation of hepatoprotective effect of Pistacia lentiscus, Phillyrea latifolia and Nicotiana glauca. J Ethnopharmacol 83: 135-138. doi: 10.1016/s0378-8741(02)00241-6
  12. Kartalis A, Didagelos M, Georgiadis I, Benetos G, Smyrnioudis N, Marmaras H, Voutas P, Zotika C, Garoufalis S, Andrikopoulos G (2016) Effects of Chios mastic gum on cholesterol and glucose levels of healthy volunteers: A prospective, randomized, placebo-controlled, pilot study (CHIOS-MASTIHA). Eur J Prev Cardiol 23: 722-729. doi: 10.1177/2047487315603186
  13. Al-Said MS, Ageel AM, Parmar NS, Tariq M (1986) Evaluation of mastic, a crude drug obtained from Pistacia lentiscus for gastric and duodenal anti-ulcer activity. J Ethnopharmacol 15: 271-278. doi: 10.1016/0378-8741(86)90165-0
  14. Barton DHR, Seoane E (1956) Triterpenoids. Part XXII. The constitution and stereochemistry of masticadienonic acid. J Chem Soc 169: 4133-4135
  15. Assimopoulou AN, Papageorgiou VP (2005) GC-MS analysis of penta-and tetra-cyclic triterpenes from resins of Pistacia species. Part I. Pistacia lentiscus v ar. chia. Biomed. Chromatogr 19: 285-311. doi: 10.1002/bmc.454
  16. Marner FJ, Freyer A, Lex J (1991) Triterpenoids from gum mastic, the resin of Pistacia lentiscus. Phytochemistry 30: 3709-3712. doi: 10.1016/0031-9422(91)80095-I
  17. Rodriguez-Rodriguez R, Ruiz-Gutierrez V (2010) Functional properties of pentacyclic triterpenes contained in pomace olive oil. Functional properties of pentacyclic triterpenes contained in pomace olive oil: Olives and olive oil in health and disease prevention. Academic Press, London, pp 1431-1438. doi: 10.1016/B978-0-12-374420-3.00159-5
  18. Liu J (1995) Pharmacology of oleanolic acid and ursolic acid. J Ethnopharmacol 49: 57-68. doi: 10.1016/0378-8741(95)90032-2
  19. Howes MJR (2018) Phytochemicals as anti-inflammatory nutraceuticals and phytopharmaceuticals. Immunity and Inflammation in Health and Disease: Emerging Roles of Nutraceuticals and Functional Foods in Immune Support. Academic Press, London, pp 363-388
  20. Teodoro T, Zhang L, Alexander T, Yue J, Vranic M, Volchuk A (2008) Oleanolic acid enhances insulin secretion in pancreatic β-cells. FEBS Lett 582: 1375-1380. doi: 10.1016/j.febslet.2008.03.026
  21. Scalon Cunha LC, Andrade E Silva ML, Cardoso Furtado NAJ, Vinholis HC, Gomes Martins CH, da Silva Filho A, Cunha WR (2007) Antibacterial activity of triterpene acids and semi-synthetic derivatives against oral pathogens. Zeitschrift fur Naturforsch - Sect C J Biosci 62: 668-672. doi: 10.1515/znc-2007-9-1007
  22. Herrera MD, Rodriguez-Rodriguez R, Ruiz-Gutierrez V (2006) Functional properties of pentacyclic triterpenes contained in "Orujo" olive oil. Curr Nutr Food Sci 2: 45-49
  23. Guimaraes AG, Serafini MR, Quintans-Junior LJ (2014) Terpenes and derivatives as a new perspective for pain treatment: A patent review. Expert Opin Ther Pat 24: 243-265. doi: 10.1517/13543776.2014.870154
  24. ICH Q2B(R1) (2005) ICH guideline on validation of analytical procedure methodology. ICH Guidelines, ICH Steering Committee, Brussels, Belgium
  25. Jin Y, Zhao J, Jeong KM, Yoo DE, Han SY, Choi SY, Ko DH, Kim H, Sung NH, Lee J (2017) A simple and reliable analytical method based on HPLC-UV to determine oleanonic acid content in Chios gum mastic for quality control. Arch Pharm Res 40: 49-56. doi: 10.1007/s12272-016-0853-2
  26. Mahato SB, Sen S (1997) Advances in triterpenoid research. Phytochemistry 44: 1185-1236. doi: 10.1016/S0031-9422(96)00639-5
  27. Wang Z, Wang H, Kang Z, Wu Y, Xing Y, Yang Y (2020) Antioxidant and anti-tumour activity of triterpenoid compounds isolated from Morchella mycelium. Arch Microbiol 202: 1677-1685. doi: 10.1007/s00203-020-01876-1
  28. Huang MT, Badmaev V, Ding Y, Liu Y, Xie JG, Ho CT (2000) Antitumor and anti-carcinogenic activities of triterpenoid, β-boswellic acid. Biofactors 13: 225-230. doi: 10.1002/biof.5520130135
  29. Fourie TG, Snyckers FO (1989) A pentacyclic triterpene with anti-inflammatory and analgesic activity from the roots of Commiphora merkeri. J Nat Prod 52: 1129-1131. doi: 10.1021/np50065a034
  30. Nozaki H, Matsuura Y, Hirono S, Kasai R, Chang JJ, Lee KH (1990) Antitumor agents, 116. Cytotoxic triterpenes from Maytenus diversifolia. J Nat Prod 53: 1039-1041. doi: 10.1021/np50070a050
  31. Lee HD, Paje LA, Choi J, Kim J, Yu AR, Bae MJ, Lee S (2021) HPLC/DAD Method Validation of 6-Hydroxyluteolin 7-O-Glucoside Analysis from Salvia plebeia. Korean J Pharmacogn 52: 186-191
  32. Lee HD, Paje LA, Lee S, Kang KS, Hong K, Kwon H, Lee S (2021) Optimization of an analytical HPLC-DAD method for detecting hydroxycinnamic acid derivatives from mixtures of Saussurea grandifolia and Taraxacum coreanum. Appl Biol Chem 64: 1-7. doi: 10.1186/s13765-021-00622-5