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Planta Med 2013; 79(02): 181-188
DOI: 10.1055/s-0032-1328089
Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Simultaneous Determination and Characterization of Tannins and Triterpene Saponins from the Fruits of Various Species of Terminalia and Phyllantus emblica Using a UHPLC-UV-MS Method: Application to Triphala

Bharathi Avula
1   National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, The University of Mississippi, University, MS 38677, USA
,
Yan-Hong Wang
1   National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, The University of Mississippi, University, MS 38677, USA
,
Mei Wang
1   National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, The University of Mississippi, University, MS 38677, USA
,
Yun-Heng Shen
1   National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, The University of Mississippi, University, MS 38677, USA
,
Ikhlas A. Khan
1   National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, The University of Mississippi, University, MS 38677, USA
2   Department of Pharmacognosy, School of Pharmacy, The University of Mississippi, University, MS 38677, USA
› Author Affiliations
Further Information

Publication History

received 29 June 2012
revised 28 October 2012

accepted 30 November 2012

Publication Date:
08 January 2013 (online)

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Abstract

Terminalia species are a rich source of tannins. Many preparations of these species are used in traditional medicine and have many different ethnobotanical applications. A simple UHPLC method was developed for the simultaneous analysis of such hydrolysable tannins and triterpene saponins from the fruit rinds of different species of Terminalia (T. chebula, T. arjuna, T. bellirica) and Phyllantus emblica. A separation by LC was achieved using a reversed-phase column and a water/acetonitrile mobile phase, both containing formic acid, using a gradient system and a temperature of 40 °C. Eight hydrolysable tannins (gallic acid, gallic acid methyl ester, corilagin, chebulagic acid, 1,2,3,6-tetra-O-galloyl-β-D-glucose, ellagic acid, chebulinic acid, and 1,2,3,4,6-penta-O-galloyl-β-D-glucose) and six triterpene saponins (arjunglucoside-I, arjunglucoside-III, chebuloside II, bellericoside, arjunetin, and arjunglucoside-II) could be separated within 20 minutes. The wavelength used for detection with the diode array detector was 254 and 275 nm for tannins and 205 nm for triterpene saponins. The method was validated for linearity, repeatability, limits of detection, and limits of quantification. The developed method is economical, fast, and especially suitable for quality control analysis of tannins and triterpene saponins in various plant samples and commercial products of Terminalia.

Key words

Terminalia - Combretaceae - Phyllantus emblica - tannins - triterpene saponins - UHPLC-UV-MS

Supporting Information

 

  • References

  • 1 Kirtikar KR. Indian medicinal plants. 2nd. edition. Uttranchal, India: Oriental Enterprises; 2001: 1415-1439
    Search in Google Scholar
  • 2 Ahmad I, Mehmood Z, Mohammad F. Screening of some Indian medicinal plants for their antimicrobial properties. J Ethnopharmacol 1998; 62: 183-193
    CrossrefPubMedSearch in Google Scholar
  • 3 Jagetia GC, Malagi KJ, Baliga MS, Venkatesh P, Veruva RR. Triphala, an ayurvedic rasayana drug, protects mice against radiation-induced lethality by free-radical scavenging. J Altern Complement Med 2004; 10: 971-978
    CrossrefPubMedSearch in Google Scholar
  • 4 Chattopadhyay RR, Bhattacharyya SK. Terminalia chebula: an update. Pharmacogn Rev 2007; 1: 151-156
    PubMedSearch in Google Scholar
  • 5 Juang LJ, Sheu SJ. Chemical identification of the sources of commercial Fructus Chebulae. Phytochem Anal 2005; 16: 246-251
    CrossrefPubMedSearch in Google Scholar
  • 6 Han Q, Song J, Qiao C, Wong L, Xu H. Preparative isolation of hydrolysable tannins chebulagic acid and chebulinic acid from Terminalia chebula by high-speed counter-current chromatography. J Sep Sci 2006; 29: 1653-1657
    CrossrefPubMedSearch in Google Scholar
  • 7 Mahajan A, Pai N. Simultaneous isolation and identification of phytoconstituents from Terminalia chebula by preparative chromatography. J Chem Pharm Res 2010; 2: 97-103
    PubMedSearch in Google Scholar
  • 8 Pandey G, Pandey SP. Phytochemical and toxicity study of Emblica officinalis (amla). Int Res J Pharm 2011; 2: 270-272
    PubMedSearch in Google Scholar
  • 9 Gupta PC. Biological and pharmacological properties of Terminalia chebula Retz. (Haritaki)- An overview. Int J Pharm Pharm Sci 2012; 4: 62-68
    PubMedSearch in Google Scholar
  • 10 Sumitra M, Manikandan P, Kumar DA, Arutselvan N, Balakrishna K, Manohar BM, Puvanakrishnan R. Experimental myocardial necrosis in rats: role of arjunolic acid on platelet aggregation, coagulation and antioxidant status. Mol Cell Biochem 2001; 224: 135-142
    CrossrefPubMedSearch in Google Scholar
  • 11 Kaur S, Jaggi RK. Antinociceptive activity of chronic administration of different extracts of Terminalia bellerica Roxb. and Terminalia chebula Retz. fruits. Indian J Exp Biol 2010; 48: 925-930
    PubMedSearch in Google Scholar
  • 12 Khatoon S, Singh N, Srivastava N, Rawat AKS, Mehrotra S. Chemical evaluation of seven Terminalia species and quantification of important polyphenols by TLC. J Planar Chromatogr Mod TLC 2008; 21: 167-171
    CrossrefPubMedSearch in Google Scholar
  • 13 Jeganathan NS, Kannan K. HPTLC method for estimation of ellagic acid and gallic acid in Triphala churanam formulations. Res J Phytochem 2008; 2: 1-9
    PubMedSearch in Google Scholar
  • 14 Singh DP, Govindarajan R, Rawat AKS. High-performance liquid chromatography as a tool for the chemical standardisation of Triphala – an Ayurvedic formulation. Phytochem Anal 2008; 19: 164-168
    CrossrefPubMedSearch in Google Scholar
  • 15 Patel MG, Patel VR, Patel RK. Development and validation of improved RP-HPLC method for identification and estimation of ellagic and gallic acid in Triphala churna . Int J ChemTech Res 2010; 2: 1486-1493
    PubMedSearch in Google Scholar
  • 16 Tanaka T, Nonaka G, Nishioka I. Tannins and related compounds. XLII. Isolation and characterization of four new hydrolyzable tannins, terflavins A and B, tergallagin and tercatain from the leaves of Terminalia catappa L. Chem Pharm Bull 1986; 34: 1039-1049
    CrossrefPubMedSearch in Google Scholar
  • 17 Juang LJ, Sheu SJ, Lin TC. Determination of hydrolyzable tannins in the fruit of Terminalia chebula Retz. by high-performance liquid chromatography and capillary electrophoresis. J Sep Sci 2004; 27: 718-724
    CrossrefPubMedSearch in Google Scholar
  • 18 Pfundstein B, El DSK, Hull WE, Haubner R, Erben G, Owen RW. Polyphenolic compounds in the fruits of Egyptian medicinal plants (Terminalia bellerica, Terminalia chebula and Terminalia horrida): characterization, quantitation and determination of antioxidant capacities. Phytochemistry 2010; 71: 1132-1148
    CrossrefPubMedSearch in Google Scholar
  • 19 Yao QQ, Zuo CX. Chemical studies on the constituents of Phyllanthus urinaria L. Yao Xue Xue Bao 1993; 28: 829-835
    PubMedSearch in Google Scholar
  • 20 Liu X, Cui C, Zhao M, Wang J, Luo W, Yang B, Jiang Y. Identification of phenolics in the fruit of emblica (Phyllanthus emblica L.) and their antioxidant activities. Food Chem 2008; 109: 909-915
    CrossrefPubMedSearch in Google Scholar
  • 21 Wang W, Ali Z, Li XC, Shen Y, Khan IA. Triterpenoids from two Terminalia species. Planta Med 2010; 76: 1751-1754
    Thieme ConnectPubMedSearch in Google Scholar
  • 22 Wang W, Ali Z, Li XC, Shen Y, Khan IA. 18,19-secooleanane type triterpene glycosyl esters from the bark of Terminalia arjuna . Planta Med 2010; 76: 903-908
    Thieme ConnectPubMedSearch in Google Scholar
  • 23 Yoshida T, Amakura Y, Yoshimura M. Structural features and biological properties of ellagitannins in some plant families of the order Myrtales. Int J Mol Sci 2010; 11: 79-106
    CrossrefPubMedSearch in Google Scholar
  • 24 Haslam E, Uddin M. Gallotannins. XV. Some observations on the structure of chebulinic acid and its derivatives. J Chem Soc C 1967; 2381-2384
    CrossrefPubMedSearch in Google Scholar
  • 25 Wilkins CK, Bohm BA. Complex ellagitannins from Tellima grandiflora . Planta Med 1976; 30: 72-74
    Thieme ConnectPubMedSearch in Google Scholar
  • 26 Yoshida T, Hatano T, Okuda T, Memon MU, Shingu T, Inoue K. Spectral and chromatographic analyses of tannins. I. Carbon-13 nuclear magnetic resonance spectra of hydrolyzable tannins. Chem Pharm Bull 1984; 32: 1790-1799
    CrossrefPubMedSearch in Google Scholar
  • 27 ICH. Validation of analytical procedures: text and methodology. ICH Harmonized Tripartite Guidelines 2005. Available at http://www.ich.org/fileadmin/Public_Web_Site/ICH_Products/Guidelines/Quality/Q2_R1/Step4/Q2_R1__Guideline.pdf Accessed December 18, 2012
    PubMed
  • 28 Zhu H, Wei W, Zhou M, Yang D, Fan X, Liu J. Chemical constituents of Phyllanthus niruri L. Tianran Chanwu Yanjiu Yu Kaifa 2011; 23: 401-403
    PubMedSearch in Google Scholar
  • 29 Reddy KK, Rajadurai S, Sastry KNS, Nayudamma Y. Dhava tannins. I. The isolation and constitution of a gallotannin from dhava (Anogeissus latifolia). Aust J Chem 1964; 17: 238-245
    PubMedSearch in Google Scholar
  • 30 Aaby K, Ekeberg D, Skrede G. Characterization of phenolic compounds in strawberry (Fragaria ananassa) fruits by different HPLC detectors and contribution of individual compounds to total antioxidant capacity. J Agric Food Chem 2007; 55: 4395-4406
    CrossrefPubMedSearch in Google Scholar
  • 31 Barreto JC, Trevisan MTS, Hull WE, Erben G, de Brito ES, Pfundstein B, Wuertele G, Spiegelhalder B, Owen RW. Characterization and quantitation of polyphenolic compounds in bark, kernel, leaves, and peel of mango (Mangifera indica L.). J Agric Food Chem 2008; 56: 5599-5610
    CrossrefPubMedSearch in Google Scholar
  • 32 Owen RW, Haubner R, Hull WE, Erben G, Spiegelhalder B, Bartsch H, Haber B. Isolation and structure elucidation of the major individual polyphenols in carob fibre. Food Chem Toxicol 2003; 41: 1727-1738
    CrossrefPubMedSearch in Google Scholar
  • 33 Hatano T, Yoshida T, Shingu T, Okuda T. Carbon-13 nuclear magnetic resonance spectra of hydrolyzable tannins. III. Tannins having 1C4 glucose and C-glucosidic linkage. Chem Pharm Bull 1988; 36: 3849-3856
    CrossrefPubMedSearch in Google Scholar
  • 34 Barry KM, Davies NW, Mohammed CL. Identification of hydrolysable tannins in the reaction zone of Eucalyptus nitens wood by high performance liquid chromatography-electrospray ionization mass spectrometry. Phytochem Anal 2001; 12: 120-127
    CrossrefPubMedSearch in Google Scholar
  • 35 Isobe R, Tanaka T, Nonaka G, Nishioka I. Tannins and related compounds. LXXX. A new method for structural study of hydrolyzable tannins by negative ion fast atom bombardment mass spectrometry. Chem Pharm Bull 1989; 37: 1748-1750
    CrossrefPubMedSearch in Google Scholar