CC BY-NC-ND 4.0 · Planta Medica International Open 2020; 07(04): e133-e144
DOI: 10.1055/a-1272-2903
Original Article

Application of UHPLC-ESI-QTOF-MS in Phytochemical Profiling of Sage (Salvia officinalis) and Rosemary (Rosmarinus officinalis)

1   Department of Physiology and Health, Maharishi International University and Health Research Institute, Fairfield, Iowa
,
Yashaswini Sharma
2   Department of Sustainable Living, Maharishi International University, Fairfield, Iowa
,
John Fagan
3   Health Research Institute, Fairfield, Iowa
,
Jim Schaefer
4   Soil Technologies Corp., Fairfield, Iowa
› Author Affiliations
Funding: Special thanks to Health Research Institute, Fairfield, Iowa for funding and providing the facility to analyze the samples

Abstract

UHPLC with QTOF-MS is widely used as a powerful tool for metabolomic analysis. This technology has recently been applied to the analysis of polyphenols in food and herb extracts. Sage (Salvia officinalis) and rosemary (Rosmarinus officinalis), belonging to the family Lamiaceae, are known for their potent antioxidant properties due to the presence of polyphenols. We have developed a sensitive and reproducible UHPLC-QTOF-MS/MS-based method for comprehensive phytochemical profiling and the identification and quantitation of specific polyphenolic compounds present in sage and rosemary leaves. The herbs were extracted ultrasonically using methanol as the solvent. In sage, rosmarinic acid (17 678.7±673.4 µg/g) and 12-methoxy carnosic acid (21 918.3±715.4 µg/g) were found in the highest concentrations among all polyphenols. In contrast, rosmarinic acid (14 311.0±636.4 µg/g), luteolin-3'-acetyl-O-glucuronide (1488.50±47.58 µg/g), and luteolin-7-O-glucuronide (1053.68±68.83 µg/g) were observed in the highest concentrations in rosemary. Sagerinic acid, rosmanol, rosmadial, carnosol, and carnosic acid were found in abundance in both sage and rosemary. The pentacyclic triterpenoid, corosolic acid ([M - H]¯ m/z 471.35), was detected for the first time in both plants. Of the 47 polyphenolic compounds identified in each plant, 38 compounds were found in common in rosemary and sage. A flavonoid compound, baicalin ([M -H]¯ m/z 445.08), was identified for the first time in S. officinalis. Also, pectolinarigenin ([M - H]¯ m/z 313.07), a dimethoxyflavone, was detected for the first time in both sage and rosemary leaves.

Supporting Information



Publication History

Received: 10 March 2020
Received: 14 July 2020

Accepted: 24 September 2020

Article published online:
03 November 2020

© 2020. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/).

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  • References

  • 1 Andrews GL, Simons BL, Young BJ, Hawkridge AM, Muddiman DC. Performance characteristics of a new hybrid triple quadrupole time-of-flight tandem mass spectrometer. Anal Chem 2011; 83: 5442-5446
  • 2 Zhu X, Chen Y, Subramanian R. Comparison of information-dependent acquisition, SWATH, and MSAll techniques in metabolite identification study employing ultrahigh-performance liquid chromatography−quadrupole time of-flight mass spectrometry. Anal Chem 2014; 86: 1202-1209
  • 3 Kaufmann A. Combining UHPLC and high-resolution MS: A viable approach for the analysis of complex samples?. Trends in Analytical Chemistry 2014; 63: 113-128
  • 4 Li H, Yao W, Liu Q, Xu J, Bao B, Shan M, Cao Y, Cheng F, Ding A, Zang L. Application of UHPLC-ESI-Q-TOF-MS to identify multiple constituents in processed products of the herbal medicine Ligustri Lucidi Fructus. Molecules 2017; 22: 689
  • 5 Kumar S, Singh A, Kumar B. Identification and characterization of phenolics and terpenoids from ethanolic extracts of Phyllanthus species by HPLC-ESI-QTOF-MS/MS. J Pharm Anal 2017; 2: 214-222
  • 6 Jin Y, Ma Y, Xie W, Hou L, Xu H, Zhang K, Zhang L, Du Y. UHPLC-Q-TOF-MS/MS-oriented characteristic components dataset and multivariate statistical techniques for the holistic quality control of Usnea. RAC Adv 2018; 8: 15487-15500
  • 7 Brighenti V, Groothuisa SF, Prencipe PF, Amir R, Benvenuti F, Pellati F. Metabolite fingerprinting of Punica granatum L. (pomegranate) polyphenols by means of high-performance liquid chromatography with diode array and electrospray ionization-mass spectrometry detection. J Chromatogr A 2017; 1480: 20-31
  • 8 Tzima K, Brunton NP, Rai DK. Qualitative and quantitative analysis of polyphenols in lamiaceae. plants-A review. Plants 2018; 7: 25
  • 9 Cajka T, Fiehn O. Comprehensive analysis of lipids in biological systems by liquid chromatography-mass spectrometry. Trends Analyt Chem 2014; 61: 192-206
  • 10 Genena AK, Hense H, Smânia Junior A, Machado de Souza S. Rosemary (Rosmarinus officinalis): A study of the composition, antioxidant and antimicrobial activities of extracts obtained with supercritical carbon dioxide. Ciência e Tecnol Aliment 2008; 28: 463-469
  • 11 Hamidpour M, Hamidpour R, Hamidpour S, Shahlari M. Chemistry, Pharmacology and Medicinal Property of Sage (Salvia) to Prevent and Cure Illnesses such as Obesity, Diabetes, Depression, Dementia, Lupus, Autism, Heart Disease and Cancer. J Tradit Complement Med 2014; 4: 82-88
  • 12 Ghorbani A, Esmaeilizadeh M. Pharmacological properties of Salvia officinalis and its components. J Tradit Complement Med 2017; 7: 433-440
  • 13 Garcia CSC, Menti C, Lambert APF. Pharmacological perspectives from Brazilian Salvia officinalis (Lamiaceae): Antioxidant, and antitumor in mammalian cells. An Acad Bras de Cienc 2016; 88: 281-292
  • 14 Lopresti AL. Salvia (Sage): A Review of its Potential Cognitive-Enhancing and Protective Effects. Drugs R D 2017; 17: 53-64
  • 15 Sharma Y, Fagan J, Schaefer J. Ethnobotany, phytochemistry, cultivation and medicinal properties of Garden sage (Salvia officinalis L.). J Pharmacogn Phytochem 2019; 8: 3139-3148
  • 16 Miraj S, Kiani S. A review study of therapeutic effects of Salvia officinalis L. Der Pharm Lett 2016; 8: 299-303
  • 17 Hamidpour R. Medicinal Property of Sage (Saliva) for Curing Illnesses Such as Obesity, Diabetes, Depression, Dementia, Lupus, Autism, Heart Disease and Cancer: A Brief Review. Arch. Cancer Res 2015; 3: 41-44
  • 18 Walch S, Tinzoh L, Zimmerman B, Stuhlinger W, Lachenmeier D. Antioxidant Capacity and Polyphenolic Composition as Quality Indicators for Aqueous Infusions of Salvia officinalis L. (sage tea). Front Pharmacol 2011; 2: 79
  • 19 Minaiyan M, Ghannadi AR, Afsharipour M, Mahzouni P. Effects of extract and essential oil of Rosmarinus officinalis L. on TNBS-induced colitis in rats. Res Pharm Sci 2011; 6: 13-21
  • 20 Orhan I, Aslan S, Kartal M, Şener B, Baser KHC. Inhibitory effect of Turkish Rosmarinus officinalis L. on acetylcholinesterase and butyrylcholinesterase enzymes. Food Chem 2008; 108: 663-668
  • 21 Al Sereitia MR, Abu-Amerb KM, Sena P. Pharmacology of rosemary (Rosmarinus officinalis Linn.) and its therapeutic potentials. Indian J Exp Biol 1999; 37: 124-131
  • 22 Jordan MJ, Lax V, Rota MC, Loran S, Sotomayor JA. Effect of bioclimatic area on the essential oil composition and antibacterial activity of Rosmarinus officinalis L. Food Control 2013; 30: 463-468
  • 23 Kontogianni VG, Tomic G, Nikolic I, Nerantzaki AA, Sayyad N, Stosic-Grujicic S, Stojanovic I, Gerothanassis IP, Tzakos AG. Phytochemical profile of Rosmarinus officinalis and Salvia officinalis extracts and correlation to their antioxidant and anti-proliferative activity. Food Chem 2013; 136: 120-129
  • 24 Lu Y, Foo LY. Polyphenolics of Salvia–a review. Phytochem 2002; 59: 117-140
  • 25 Neagu E, Paun G, Radu GL. Chemical composition and antioxidant activity of Salvia officinalis concentrated by ultrafiltration. Rom Biotechnol Lett 2014; 19: 9203-9211
  • 26 Borras-Linares I, Stojanovic Z, Quirantes-Pine R, Arráez-Román D, Švarc-Gajić J, Fernández-Gutiérrez A, Segura-Carretero A. Rosmarinus officinalis leaves as a natural source of bioactive compounds. Int J Mol Sci 2014; 15: 20585-20606
  • 27 Mena P, Cirlini M, Tassotti M, Herrlinger KA, Dall’Asta C, DelRio D. Phytochemical profiling of flavonoids, phenolic acids, terpenoids, and volatile fraction of a rosemary (Rosmarinus officinalis L.) extract. Molecules 2016; 21: 1576
  • 28 Zimmermann BF, Walch SG, Tinzoh LN, Stühlinger W, Lachenmeier DW. Rapid UHPLC determination of polyphenols in aqueous infusions of Salvia officinalis L. (sage tea). J Chromatogr B 2011; 879: 2459-2464
  • 29 Jensen PK, Wujcik CE, McGuire MK, McGuire MA. Validation of reliable and selective methods for direct determination of glyphosate and aminomethylphosphonic acid in milk and urine using LC-MS/MS. J Environ Sci Health B 2016; 51: 254-259
  • 30 Hamrouni-Sellami I, Rahali FZ, Rebey IB, Bourgou S, Limam F, Marzouk B. Total phenolics, flavonoids, and antioxidant activity of Sage (Salvia officinalis L.) plants as affected by different drying methods. Food Bioprocess Technol 2013; 6: 806-817
  • 31 Martins N, Barros L, Santos-Buelga C, Henriques M, Silva S, Ferreira ICFR. Evaluation of bioactive properties and phenolic compounds in different extracts prepared from Salvia officinalis L. Food Chem 2015; 170: 378-385
  • 32 Madala NE, Piater L, Dubery I, Steenkamp P. Distribution patterns of flavonoids from three Momordica species by ultra-high performance liquid chromatography quadrupole time of flight mass spectrometry: A metabolomics profiling approach. Rev Bras Farmacogn 2016; 26: 507-513
  • 33 Mercolini L, Protti M, Saracino MA, Mandrone M, Antognoni F. Analytical profiling of bioactive phenolic compounds in argan (Argania spinosa) leaves by combined microextraction by packed sorbent (MEPS) and LC-DAD-MS/MS. Phytochem Anal 2016; 27: 41-49
  • 34 Neumann S, Bocker S. Computational mass spectrometry for metabolomics: identification of metabolites and small molecules. Anal Bioanal Chem 2010; 398: 2779-2788
  • 35 Cajka T, Fiehn O. Toward merging untargeted and targeted methods in mass spectrometry-based metabolomics and lipidomics. Anal Chem 2015; 88: 524-545
  • 36 Dunn WB, Erban A, Weber RJM, Creek DJ, Brown M, Breitling R, Hankemeier T, Goodacre R, Neumann S, Kopka J, Viant MR. Mass appeal: Metabolite identification in mass spectrometry-focused untargeted metabolomics. Metabolomics 2012; 9: 44-66
  • 37 Lee B, Lim C, Lim S, Cho S. Baicalin administered orally after ischemia/reperfusion alleviated brain injury in mice by inhibiting inflammation and edema. Nat Prod Commun 2019; 14: 1934578X19843032
  • 38 Sowndhararajan K, Deepa P, Kim M, Park JS, Kim S. Neuroprotective and cognitive enhancement potentials of Baicalin: A review. Brain Sci 2018; 8: 104
  • 39 Borras-Linares I, Arraez-Roman D, Herrero M, Ibanez E, Segura-Carretero A, Fernandez-Gutierrez A. Comparison of different extraction procedures for the comprehensive characterization of bioactive phenolic compounds in Rosmarinus officinalis by reversed-phase high-performance liquid chromatography with diode array detection coupled to electrospray time-of-flight mass spectrometry. J Chromatogr A 2011; 1218: 7682-7690
  • 40 Lim H, Son KH, Chang HW, Bae K, Kang SS, Kim HP. Anti-inflammatory activity of pectolinarigenin and pectolinarin isolated from Cirsium chanroenicum. Biol Pharm Bull 2008; 31: 2063-2067
  • 41 Patel K, Gadewar M, Tahilyani V, Patel DK. A review on pharmacological and analytical aspects of diosmetin: a concise report. Chin J Integr Med 2013; 19: 792-800
  • 42 Wang J, Xu J, Gong X, Yang M, Zhang C, Li M. Antioxidative phenolic compounds from sage (Salvia officinalis). J Agric Food Chem 1998; 46: 4869-4873
  • 43 Lu Y, Foo LY. Rosmarinic acid derivatives from Salvia officinalis. Phytochem 1999; 51: 91-94
  • 44 Cuvelier M, Richard H, Berset C. Antioxidative activity and phenolic composition of pilot-plant and commercial extracts of sage and rosemary. JAOCS 1996; 73: 645-652
  • 45 Hossain MB, Rai DK, Brunton NP, Martin-Diana AB, Barry-Ryan AC. Characterization of phenolic composition in Lamiaceae spices by LC-ESI-MS/MS. J Agric Food Chem 2010; 58: 10576-10581
  • 46 Jakovljevic M, Jokic S, Molnar M, Jasic M, Babic J, Jukic H, Banjari I. Bioactive Profile of Various Salvia officinalis L. Preparations. Plants 2019; 8: 55
  • 47 Abdollahi-Ghehi H, Sonboli A, Ebrahimi SN, Esmaeili MA, Mirjalili MH. Triterpenic Acid Content and Cytotoxicity of Some Salvia Species from Iran. Nat Prod Commun 2019; 14: 1934578x19842722
  • 48 Wen CC, Kuo YH, Jan JT, Linag PH, Wang SY, Liu HG, Lee CK, Chang ST, Kuo CJ, Lee SS, Hou CC, Hsiao PW, Chien SC, Shyur LF, Yang NS. Specific plant terpenoids and lignoids possess potent antiviral activities against severe acute respiratory syndrome coronavirus. J Med Chem 2007; 50: 4087-4095
  • 49 Bahadori MB, Dinparast L, Valizadeh H, Farimani MM, Ebrahimi SN. Bioactive constituents from roots of Salvia syriaca L.: Acetylcholinesterase inhibitory activity and molecular docking studies. S Afr J Bot 2016; 106: 1-4
  • 50 Saeidnia S, Ghamarinia M, Gohari AR, Shakeri A. Terpenes From the Root of Salvia hypoleuca Benth. Daru 2012; 20: 66
  • 51 Alqahtani A, Hamid K, Kam A, Wong KH, Abdelhak Z, Razmovski-Naumovski V, Chan K, Li KM, Groundwater PW, Li GQ. The pentacyclic triterpenoids in herbal medicines and their pharmacological activities in diabetes and diabetic complications. Curr Med Chem 2013; 20: 908-931
  • 52 Laszczyk MN. Pentacyclic triterpenes of the lupane, oleanane and ursane group as tools in cancer therapy. Planta Med 2009; 75: 1549-1560
  • 53 Xie C, Zhong D, Yu K, Chen X. Recent advances in metabolite identification and quantitative bioanalysis by LC–Q-TOF MS. Bioanalysis 2012; 4: 937-959
  • 54 Gifford I, Battenberg K, Vaniya A, Wilson A, Tian L, Fiehn O, Berry AM. Distinctive patterns of flavonoid biosynthesis in roots and nodules of Datisca glomerata and Medicago spp. revealed by metabolomic and gene expression profiles. Front Plant Sci 2018; 9: 1463