Skip to main content

Isolation and Identification of Iridoids

  • Chapter
  • First Online:
Pharmacology and Applications of Naturally Occurring Iridoids

Abstract

Diverse pharmacological activities of iridoids encouraged several chemists and pharmacologists for isolation of these compounds in large quantities in pure states for use as chemical standards as well as for further pharmacological studies. The separation and isolation of pure iridoid and secoiridoid glycosides and aglycones from crude plant extracts by conventional chromatographic systems such as thin-layer and column chromatographic methods are time consuming and require large amounts of organic solvents, and numerous chromatographic steps resulting in the lower recovery and higher cost for isolation.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

eBook
USD 16.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Hardcover Book
USD 109.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Chai X, Sui YF, Zheng YH, Yan SL, Zhang X, Gao XM (2010) Biochem Syst Ecol 38:210; Takamura C, Hirata T, Ueda T, Ono M, Miyashita H, Ikeda T, Nohara T (2007) J Nat Prod 70:1312

    Google Scholar 

  2. Gardner DR, Stermitz FR (1988) J Chem Ecol 15:2147; Inouye H, Uobe K, Hirai M (1976) J Chromatogr 118:201

    Google Scholar 

  3. Meinwald J, Jones TH, Eisner T, Hicks K (1977) Proc Natl Acad Sci USA 74:2189

    CAS  PubMed  Google Scholar 

  4. Bolzani VS, Izumisawa CM, Young MCM, Trevisan LMV, Kingston DGI, Gunatilaka AL (1997) Phytochemistry 46:305

    Google Scholar 

  5. Morlock GE, Schwack W (2010) J Chromatogr A 1217:6600; Choma IM, Jesionek W (2015) Chromatogr 2:225

    Google Scholar 

  6. Choma I, Grzelak EM (2011) J Chromatogr A 1218:2684; Marston A (2011) J Chromatogr A 1218:2676

    Google Scholar 

  7. Rodriguez S, Wolfender JL, Hakizamungu E, Hostettmann K (1995) Planta Med 61:362; Luciano JHS, Lima MAS, Silveira ER, Vasconcelos IM, Fernandes GS, de Souza EB (2010) Quim Nova 33:292

    Google Scholar 

  8. Yadav D, Gupta M (2013) J Planar Chromatogr 26:10

    Google Scholar 

  9. Ferreira JLP, Amaral ACF, Araujo RB, Carvalho JR, Proenca CEB, Fraga SAPM, Silva JRA (2009) Int J Bot 5:171

    CAS  Google Scholar 

  10. Ersoz T, Berkman MZ, Tasdemir D, Ireland CM, Calis I (2000) J Nat Prod 63:1449

    Google Scholar 

  11. Sunghwa F, Koketsu M (2009) Nat Prod Res 23:1408

    CAS  PubMed  Google Scholar 

  12. Saleem M, Akhtar N, Riaz N, Ali MS, Jabbar A (2011) J Asian Nat Prod Res 13:1122

    CAS  PubMed  Google Scholar 

  13. Silva JRA, Amaral ACF, Silveira CV, Rezende CM, Pinto AC (2007) Acta Amazonica 37:119

    CAS  Google Scholar 

  14. Wu HK, Chuang WC, Sheu SJ (1998) J Chromatogr A 803(1–2):179

    CAS  Google Scholar 

  15. Kabzinski AKM, Rozga M, Wysokinska H, Skrzypck Z (1997) Herba Pol 43:437

    CAS  Google Scholar 

  16. Baghdikian B, Lanhers MC, Fleurentin J, Olivier E, Maillard C, Balansard G, Montier F (1997) Planta Med 63:171

    CAS  PubMed  Google Scholar 

  17. Bicchi C, Binello A, Rubiolo P (2000) Phytochem Anal 11:179

    CAS  Google Scholar 

  18. Jensen SR, Gotfredsen CH, Grayer RJ (2008) Biochem Syst Ecol 36:207

    CAS  Google Scholar 

  19. Bianco A, De Luca A, Mazzei RA, Nicoletti M, Passacantilli P, Lima RAD (1994) Phytochemistry 35:1485

    CAS  Google Scholar 

  20. Yu Y, Xie ZL, Gao H, Ma WW, Dai Y, Wang Y, Zhong Y, Yao XS (2009) J Nat Prod 72:1459

    CAS  PubMed  Google Scholar 

  21. Franzyk H, Jensen SR, Stermitz FR (1998) Phytochemistry 49:2025

    CAS  Google Scholar 

  22. Kirmizibekmez H, Ariburnu E, Masullo M, Festa M, Capasso A, Yesilada E, Piacente S (2012) Fitoterapia 83:130

    CAS  PubMed  Google Scholar 

  23. Tascova R, Handjieva N, Peev D, Popov S (1998) Phytochemistry 49:1323

    Google Scholar 

  24. Alipieva KI, Jensen SR, Franzyk H, Handjieva N, Evstatievac LN (2000) Z Naturforsch 55:137

    CAS  Google Scholar 

  25. Ito Y (2005) J Chromatogr A 1065:145

    CAS  PubMed  Google Scholar 

  26. Tanimura T, Pisano JJ, Ito Y, Bowman RL (1970) Science 169:54

    CAS  PubMed  Google Scholar 

  27. Hostettmann K (1980) Planta Med 39:1

    CAS  Google Scholar 

  28. Otsuka H, Kashima N, Nakamoto K (1996) Phytochemistry 42:1435

    CAS  Google Scholar 

  29. Nahrstedt A, Rockenbach J, Wray V (1995) Phytochemistry 39:375

    CAS  Google Scholar 

  30. Kanemoto M, Matsunami K, Otsuka H, Shinzato T, Ishigaki C, Takeda Y (2008) Phytochemistry 69:2517

    CAS  PubMed  Google Scholar 

  31. Inoue K, Nishioka T, Tanahashi T, Inouye H (1982) Phytochemistry 21:2305

    CAS  Google Scholar 

  32. Otsuka H, Sasaki Y, Kubo N, Yamasaki K, Takeda Y, Seki T (1991) J Nat Prod 54:547

    CAS  Google Scholar 

  33. Potterat O, Msonthi JD, Hostettmann K (1988) Phytochemistry 27:2677

    CAS  Google Scholar 

  34. Hostettmann K, Hostettmann-Kaldas M, Sticher O (1979) Helv Chim Acta 62:2079

    CAS  Google Scholar 

  35. Ito Y, Bowman RL (1970) J Chromatogr Sci 8:315; Ito Y (1981) J Chromatogr A 214:122

    Google Scholar 

  36. Ito Y (1988) Principles and instrumentations of counter-current chromatography. In: Mandava NB (ed) Counter current chromatography. Theory and practice. Marcel Dekker, New York, p 443

    Google Scholar 

  37. Zhou T, Fan G, Hong Z, Chai Y, Wu Y (2005) J Chromatogr A 1100:76

    CAS  PubMed  Google Scholar 

  38. Liang J, He J, Zhu S, Zhao W, Zhang Y, Ito Y, Sun W (2013) J Liquid Chromatogr Relat Technol 36:983

    CAS  Google Scholar 

  39. Yue HL, Zhao XH, Wang QL, Tao YD (2013) J Chromatogr B 936:57

    CAS  Google Scholar 

  40. Wang Y, Chen Y, Deng L, Cai S, Liu J, Li W, Du L, Cui G, Xu X, Lu T, Chen P, Zhang H (2015) Phytochem Anal 26:202

    CAS  PubMed  Google Scholar 

  41. Tong S, Chen L, Zhang Q, Liu J, Yan J, Ito Y (2015) J Chromatogr Sci 53:725

    CAS  PubMed  Google Scholar 

  42. Lu Q, Sun Y, Shu Y, Tan S, Yin L, Guo Y, Tang L (2016) Molecules 21:1234

    PubMed Central  Google Scholar 

  43. Inouye H, Uobe K, Hirai M, Masuda Y, Hashimoto K (1976) J Chromatogr 118:201

    CAS  PubMed  Google Scholar 

  44. Weiss I, Hofferberth J, Ruther J, Stokl J (2015) Front Ecol Evol 3:19

    Google Scholar 

  45. Graham K (1998) Biotechnol Appl Biochem 27:9

    Google Scholar 

  46. Suomi J, Siren H, Hartonen K, Riekkola ML (2000) J Chromatogr A 868:73

    CAS  PubMed  Google Scholar 

  47. Suomi J, Wiedmer SK, Jussila M, Riekkola ML (2002) J Chromatogr A 970:287

    CAS  PubMed  Google Scholar 

  48. Wu HK, Chuang WC, Sheu SJ (1998) J Chromatogr A 803:179

    CAS  Google Scholar 

  49. Harput US, Varel M, Nagatsu A, Saracoglu I (2004) Phytochemistry 65:2135; Tanahashi T, Takenaka Y, Okazaki N, Koge M, Nagakura N, Nishi T (2009) Phytochemistry 70:2072

    Google Scholar 

  50. Dinda B, Debnath S, Majumder S, Sato N, Harigaya Y (2011) Chin Chem Lett 22:1233; Li N, Di L, Gao WC, Wang KJ, Zu LB (2012) J Nat Prod 75:1723; Dinda B, Debnath S, Harigaya Y (2007) Chem Pharm Bull 55:159

    Google Scholar 

  51. El-Naggar LJ, Beal JL (1980) J Nat Prod 43:649; Boros CA, Stermitz FR (1990) J Nat Prod 53:1055; Dinda B, Debnath S, Harigaya Y (2007) Chem Pharm Bull 55:159

    Google Scholar 

  52. Su BN, Pawlus AD, Jung HA, Keller WJ, McLaughlin JL, Kinghorn AD (2005) J Nat Prod 68:592; Gardner DR, Narum J, Zook D, Stermitz FR (1987) J Nat Prod 50:485

    Google Scholar 

  53. Itoh A, Kumashiro T, Yamaguchi M, Nagakura N, Mizushina Y, Nishi T, Tanahashi T (2005) J Nat Prod 68:848; Garcia J, Chulia AJ (1986) Planta Med 52:327; Damtoft S, Jensen SR, Nielsen BJ (1981) Phytochemistry 20:2717

    Google Scholar 

  54. Kuwajima H, Uemura T, Takaishi K, Inoue K, Inouye H (1988) Phytochemistry 27:1757

    CAS  Google Scholar 

  55. Calis I, Sticher O (1984) Phytochemistry 23:2539

    CAS  Google Scholar 

  56. Nishimura H, Sasaki H, Morota T, Chin M, Mitsuhashi H (1989) Phytochemistry 28:2705

    CAS  Google Scholar 

  57. Manguro LOA, Lemmen P, Hao P (2011) Rec Nat Prod 5:147

    CAS  Google Scholar 

  58. Ilieva E, Handjieva N, Popov S (1992) Z Naturforsch 47c:791

    Google Scholar 

  59. Ersoz T, Berkman MZ, Tasdemir D, Calis I, Ireland CM (2002) Turk J Chem 26:179

    CAS  Google Scholar 

  60. Jensen HFW, Jensen SR, Nielsen BJ (1987) Phytochemistry 26:3353

    CAS  Google Scholar 

  61. Handjieva NV, Ilieva EI, Spassov SL, Popov S (1993) Tetrahedron 49:9261

    CAS  Google Scholar 

  62. Ersoz T, Ivancheva S, Akbay P, Sticher O, Calis I (2001) Z Naturforsch 56c:695

    Google Scholar 

  63. Tzakou O, Mylonas P, Vagias C, Petrakis PV (2007) Z Naturforsch 62c:597

    Google Scholar 

  64. Paik YS, Lee CM, Cho MH, Hahn TR (2001) J Agric Food Chem 49:430

    CAS  PubMed  Google Scholar 

  65. Pandey AK, Siddiqui SA, Dwivedi A, Raj K, Misra N (2011) Spectroscopy 25:287

    CAS  Google Scholar 

  66. Damtoft S, Hansen SB, Jacobsen B, Jensen SR, Nielsen BJ (1984) Phytochemistry 23:2387

    CAS  Google Scholar 

  67. Calis I, Heilmann J, Tasdemir D, Linden A, Ireland CM, Sticher O (2001) J Nat Prod 64:961

    CAS  PubMed  Google Scholar 

  68. Abe F, Chen RF, Yamauchi T (1988) Chem Pharm Bull 38:2784

    Google Scholar 

  69. Haron FF, Sijam K, Omar D, Rahmani M (2013) J Biol Sci 13:158

    CAS  Google Scholar 

  70. Abe F, Mori T, Yamauchi T (1984) Chem Pharm Bull 32:2947

    CAS  Google Scholar 

  71. Ma WG, Fuzzati N, Wolfender JL, Hostettmann K, Yang CR (1994) Helv Chim Acta 77:1660

    CAS  Google Scholar 

  72. Mpondo EM, Chulia AJ (1988) Planta Med 54:185

    Google Scholar 

  73. Hu JF, Starks CM, Williams RB, Rice SM, Norman VL, Olson KM, Hough GW, Goering MG, O’Neil-Johnson M, Eldridge GR (2009) Helv Chim Acta 92:273

    CAS  Google Scholar 

  74. Levy GC, Nelson GL (1972) Carbon-13 nuclear resonance for organic chemists. Wiley, New York; Stothers JB (1972) Carbon-13 NMR spectroscopy. In: Organic chemistry. A series of monographs, vol 24. Academic Press, New York

    Google Scholar 

  75. Chaudhuri RK, Afifi-Yazar FU, Sticher O, Winkler T (1980) Tetrahedron 36:2317; Damtoft S, Jensen SR, Nielsen BJ (1981) Phytochemistry 20:2717; Chaudhuri RK, Afifi-Yazar FU, Sticher O (1979) Helv Chim Acta 62:1603; Bianco A, Passacantilli P (1980) Gazz Chim Ital 110:547

    Google Scholar 

  76. Chaudhuri RK, Afifi-Yazar FU, Sticher O, Winkler T (1980) Tetrahedron 36:2317

    CAS  Google Scholar 

  77. Damtoft S, Jensen SR, Nielsen BJ (1981) Phytochemistry 20:2717; Bianco A, Massa M, Oguakwa JU, Passacantilli P (1981) Phytochemistry 20:1871

    Google Scholar 

  78. Tanaka N, Tanaka T, Fujioka T, Fujii H, Mihashi K, Shimomura K, Ishimaru K (2001) Phytochemistry 57:1287; Calis I, Lahoub MF, Sticher O (1984) Helv Chim Acta 67:160

    Google Scholar 

  79. Gardner DR, Narum J, Zook D, Stermitz FR (1987) J Nat Prod 50:485

    CAS  Google Scholar 

  80. Dinda B, Debnath S, Harigaya Y (2007) Chem Pharm Bull 55:159

    CAS  PubMed  Google Scholar 

  81. Chaudhuri RK, Sticher O, Winkler T (1979) Tetrahedron Lett 20:3149

    Google Scholar 

  82. Dinda B, Debnath S, Banik R (2011) Chem Pharm Bull 59:803; Dinda B, Debnath S, Harigaya Y (2007) Ibid 55:159, 689

    Google Scholar 

  83. Damtoft S, Frederiksen LB, Jensen SR (1994) Phytochemistry 35:1259; Sticher O, Afifi-Yazar FU (1979) Helv Chim Acta 62:530

    Google Scholar 

  84. Malheiros A, Schuquel ITA, Vidotti GJ (1997) Quim Nova 20:457

    CAS  Google Scholar 

  85. Junior P (1983) Planta Med 47:161

    CAS  PubMed  Google Scholar 

  86. Modaressi M, Delazar A, Nazemiyeh W, Fathi-Azad F, Smith E, Rahman MM, Gibbons S, Nahar L, Sarkar SD (2009) Phytother Res 23:99; Gariboldi P, Jommi G, Verotti L (1986) Phytochemistry 25:865

    Google Scholar 

  87. Nicoletti M, Tomassini L, Garbarino JA, Piovano M, Chamy MC (1989) Biochem Syst Ecol 17:569

    CAS  Google Scholar 

  88. Martin GE, Zekter AS (1988) Two-dimensional NMR method for establishing molecular connectivity. VCH, New York, p 59

    Google Scholar 

  89. Keeler J (2010) Understanding NMR spectroscopy, 2nd edn. Wiley, New York

    Google Scholar 

  90. Scarpati ML, Guiso M (1969) Gazz Chim Ital 99:1150; Boros CA, Stermitz FR (1990) J Nat Prod 53:1055

    Google Scholar 

  91. Guvenalp Z, Ozbek H, Unsalar T, Kazaz C, Omur Demirezer L (2006) Turk J Chem 30:391

    CAS  Google Scholar 

  92. Kock M, Reif B, Fenical W, Griesinger C (1996) Tetrahedron Lett 37:363

    Google Scholar 

  93. Biemann K (1962) Mass spectrometry. McGraw-Hill, New York; Beynon JH, Saunders RA, Williams AE (1968) Mass spectra of organic molecules. Elsevier, London

    Google Scholar 

  94. Bentley TW, Johnstone RAW, Grimshaw J (1967) J Chem Soc C 2234

    Google Scholar 

  95. Bleotu A, Mandravel C, Ciuculescu C (2006) Roum Biotechnol Lett 11:2643

    CAS  Google Scholar 

  96. Popov S, Handjieva NV (1983) Mass Spectrom Rev 2:481

    CAS  Google Scholar 

  97. Lu CM, Lin LC, Tsai CH (2014) Molecules 19:21560; Es-Safi NE, Kerhous L, Ducrot PH (2007) Rapid Commun Mass Spectrom 21:1165

    Google Scholar 

  98. Zhou T, Liu H, Wen J, Fan G, Chai Y, Wu Y (2010) Rapid Commun Mass Spectrom 24:2520; Li CM, Zhang XL, Xue XY, Zhang FF, Xu Q, Liang XM (2008) Rapid Commun Mass Spectrom 22:1941

    Google Scholar 

  99. Ren L, Xue X, Zhang F, Wang Y, Liu Y, Li C, Liang X (2007) Rapid Commun Mass Spectrom 21:3039

    CAS  PubMed  Google Scholar 

  100. Li Y, Zhao Y, Zhang YM, Wang MJ, Sun WJ (2009) Carbohydr Res 344:2270

    CAS  PubMed  Google Scholar 

  101. Li ZM, Chen JJ, Li Y, Gao K, Chang J, Yao XJ (2009) Tetrahedron Lett 50:4132

    CAS  Google Scholar 

  102. Karasawa S, Yoza K, Tung NH, Uto T, Morinaga O, Suzuki M, Kwofie KD, Amoa-Bosompem M, Boakye DA, Ayi I, Adegle R, Sakyimah M, Ayertey F, Aboagye F, Appiah AA, Owusu KBA, Tuffour I, Atchoglo P, Frempong KK, Anyan WK, Appiah-Opong R, Nyarko AK, Yamashita T, Yamaguchi Y, Edoh D, Koram K, Yamaoka S, Ohta N, Shoyama Y (2015) Tetrahedron Lett 56:7158

    CAS  Google Scholar 

  103. Li M, Jia Z, Zhang R, Hu Z, Tian X (2008) Carbohydr Res 343:561

    CAS  PubMed  Google Scholar 

  104. Liang G, Xu B, Pan W, Cao P, Zhang Y, Lu Y, Wu Y, Hao X (2009) Nat Prod Res 23:1

    CAS  PubMed  Google Scholar 

  105. Sarma S, Gupta BD, Kant R, Gupta VK (2014) J Crystallogr 2014:745074

    Google Scholar 

  106. Foderaro TA, Stermitz FR, Hope H (1992) Tetrahedron Lett 33:2953

    CAS  Google Scholar 

  107. Uesato S, Shan X, Inouye H, Shingu T, Inoue M, Doi M (1987) Phytochemistry 26:561

    CAS  Google Scholar 

  108. Yu Y, Song W, Zhu C, Lin S, Zhao F, Wu X, Yue Z, Liu B, Wang S, Yuan S, Hou Q, Shi J (2011) J Nat Prod 74:2151

    CAS  PubMed  Google Scholar 

  109. Chen L, Su B, Wang J, Wen A (2014) Asian J Chem 26:8274

    Google Scholar 

  110. Geng CA, Zhang XM, Shen Y, Zuo AX, Liu JF, Ma YB, Luo J, Jiang ZY, Chen JJ (2009) Org Lett 11:4838

    CAS  PubMed  Google Scholar 

  111. Geng CA, Wang LJ, Zhang XM, Ma YB, Huang XY, Luo J, Guo RH, Zhou J, Shen Y, Zuo AX, Jiang ZY, Chen JJ (2011) Chem Eur J 17:3893

    CAS  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Biswanath Dinda .

Rights and permissions

Reprints and permissions

Copyright information

© 2019 Springer Nature Switzerland AG

About this chapter

Check for updates. Verify currency and authenticity via CrossMark

Cite this chapter

Dinda, B. (2019). Isolation and Identification of Iridoids. In: Pharmacology and Applications of Naturally Occurring Iridoids. Springer, Cham. https://doi.org/10.1007/978-3-030-05575-2_3

Download citation

Publish with us

Policies and ethics