Comprehensive chemical profiling of Picrorhiza kurroa royle ex benth using NMR, HPTLC and LC-MS/MS techniques

Combinatorial Chemistry and High Throughput Screening

Volumn 19, Issue 3, 2016, Pages 200-215

  Kumar, Dinesh ^a   Kumar, Rakesh ^a   Singh, Bikram ^a   Ahuja, Paramvir Singh ^a  

^a CSIR INSTITUTE OF HIMALAYAN BIORESOURCE TECHNOLOGY   (India)

Author keywords

HPTLC; LC MS MS; Metabolic profiling; NMR; Picrorhiza kurroa

Indexed keywords

ACETOPHENONE; ACID; ALANINE; APOCYNIN; CAFFEIC ACID; CATALPOL; CINNAMIC ACID; COUMARIC ACID; CUCURBITACIN; CUCURBITACIN GLYCOSIDE; FERULIC ACID; FLAVONOID; GALLIC ACID; GLYCINE; GLYCOSIDE; IRIDOID; ISOLEUCINE; KUTKOSIDE; LEUCINE; MANNITOL; PHENYLALANINE; PICRORHIZA KURROA EXTRACT; PICROSIDE I; RHAMNOSE; SHIKIMIC ACID; SYRINGIC ACID; TERPENOID; TYROSINE; VALINE; VANILLIC ACID; PLANT EXTRACT;

ARTICLE; BIOSYNTHESIS; DRUG QUALITY; HIGH PERFORMANCE THIN LAYER CHROMATOGRAPHY; LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PICRORHIZA KURROA; PLANT LEAF; PRIORITY JOURNAL; RHIZOME; SPECIES DIVERSITY; TANDEM MASS SPECTROMETRY; CHEMICAL STRUCTURE; CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METABOLISM;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PICRORHIZA; PLANT EXTRACTS; PLANT LEAVES; RHIZOME; TANDEM MASS SPECTROMETRY;

EID: 84964438004     PISSN: 13862073     EISSN: 18755402     Source Type: Journal    
DOI: 10.2174/1386207319666160114092538     Document Type: Article

References (66)

1. Kopka, J.; Fernie, A.; Weckwerth, W.; Gibon, Y.; Stitt, M. Metabolite profiling in plant biology: platforms and destinations. Genome Biol., 2004, 5, 109.1-109.9.
2. Ali, K.; Maltese, F.; Fortes, A.M.; Pais, M.S.; Verpoorte, R.; Choi, Y.H. Pre-analytical method for NMR-based grape metabolic fingerprinting and chemometrics. Analytica Chimica Acta, 2011, 703, 179-186.
3. Zulak, K.G.; Weljie, A.M.; Vogel, H.J.; Facchini, P.J. Quantitative 1H NMR metabolomics reveals extensive metabolic reprogramming of primary and secondary metabolism in elicitortreated opium poppy cell cultures. BMC Plant Biol., 2008, 8, 5.
4. Son, H-S.; Kim, K.M.; Van Den Berg, F.; Hwang, G-S.; Park, WM.; Lee, C-H.; Hong, Y-S. 1H nuclear magnetic resonanc based metabolomic characterization of wines by grape varieties and production areas. J. Agric. Food Chem., 2008, 56, 8007-8016.
5. Li, F.; Gonzalez, F. J.; Ma, X. LC-MS-based metabolomics in profiling of drug metabolism and bioactivation. Acta Pharmaceutica Sinca B, 2012, 2, 118-125.
6. Silas, G.V.B.; Mas, S.; Akesson, M.; Smedsgaard, J.; Nielsen, J. Mass spectrometry in metabolome analysis. Mass Spect. Rev., 2005, 24, 613-346.
7. Krug, D.; Zurek, G.; Revermann, O.; Vos, M.; Velicer, G.J.; Muller, R. Discovering the hidden secondary metabolome of Myxococcus xanthus: A study of intraspecific diversity. Appl. Environ. Microbiol., 2008, 74, 3058-3068.
8. Chothani, D.L.; Patel, M.B.; Mishra, S.H. HPTLC fingerprint profile and isolation of marker compound of Ruellia tuberose. Chromatograp. Res. Intl., 2012, 1-6.
9. Giri, L.; Andola, H.C.; Purohit, V.K.; Rawat, M.S.M.; Rawal, R.S.; Bhatt, I.D. Chromatographic and spectral fingerprinting standardization of traditional medicines: An overview as modern tools. Res. J. Phytochemistry, 2010, 4, 234-241.
10. Zhang, H.; Zhang, Z. Handbook of Chinese Traditional Medicine Resources. Science Press, Beijing 1994, 1149.
11. Huang, S-X.; Zhou, Y.; Nie, Q-J.; Ding, L-S.; Peng, S-L. Two new iridoid glucosides from Picrorhiza scrophulariiflora. J. Asian Nat. Prod. Res. 2006, 8, 259-263.
12. Singh, N.; Gupta, A. P.; Singh, B.; Kaul, V. K. Quantification of Picroside-I and Picroside-II in Picrorhiza kurroa by HPTLC. J. Liq. Chromatogr. Relat. Technol. 28, 2005, 1679-1691.
13. Thapliyal, S.; Mahadevan, N.; Nanjan, M. J. Analysis of Picroside I and Kutkoside in Picrorhiza kurroa and its formulation by HPTLC. Int. Res. J. Pharm., Biomed. Sci., 2012, 3, 25-30.
14. Stuppner, H.; Wagner, H. New cucurbitacin glycosides from Picrorhiza kurroa, Planta Med., 1989, 55, 559-563.
15. Stuppner, H.; Kaehlig, H.; Seligmann, O.; Wagner, H. Minor cucurbitacin glycosides from Picrorhiza kurroa, Phytochem, 1990, 29, 1633-1637.
16. Stuppner, H.; Muller, E.; Wagner, H. Cucurbitacins from Picrorhiza kurroa". Phytochem, 1991, 30, 305-310.
17. Sah, J.N.; Varshney, V.K. Chemical constituents of Picrorhiza genus: a Review. Am. J. Essential Oils Nat. Products., 2013, 1, 22-37.
18. Kumar, R.; Bhandari, P.; Singh, B.; Ahuja, P.S. Evaluation of Picrorhiza kurroa accessions for growth and quality in north western Himalayas. J. Med. Plants Res., 2012, 6, 2660-2665.
19. Parkash, J.K.S.; Kalita, P.J.; Devi, M.; Pathania, J.; Joshi, R.; Dutt, S. Comparative proteome analysis of Picrorhiza kurrooa Royle ex Benth. in response to drought. J. Proteome Sci. Comput. Biol., 2014, 2. 3
20. Kumar, R.; Bhandari, P.; Singh, B.; Ahuja, P. S. Evaluation of Picrorhiza kurroa accessions for growth and quality in north western Himalayas. J. Med. Plants Res., 2012, 6, 2660-2665.
21. Kumar, V.; Sood, H.; Sharma, M.; Chauhan, R.S. A proposed biosynthetic pathway of picrosides linked through the detection of biochemical intermediates in the endangered medicinal herb Picrorhiza kurroa. Phytochem. Anal., 2013, 24(6), 598-602.
22. Gaidamauskas, E.; Norkus, E.; Vaiciuniene, J.; Crans, D. C.; Vuorinen, T.; Jaciauskien, J.; Baltrunas, G. Evidence of two-step deprotonation of D-mannitol in aqueous solution. Carbohydr. Res., 2005, 340, 1553-1556.
23. Bieleski, R.L. Sugar Alcohols. In: Encyclopedia of Plant Physiology, New Series. Loewus, F., Tanner, W., Eds., Springer-Verlag: Berlin13A, 1982, pp. 158-192.
24. Lewis, D.H. Physiology and metabolism of alditols. In storage carbohydrates in vascular plants. Lewis, D.H. Ed., Cambridge University Press: Cambridge 1984, pp. 157-179.
25. Ikeda, M.; Bhattacharjee, A.K.; Kondoh, T.; Nagashima, T.; Tamaki, N. Synergistic effect of cold mannitol and Na+/Ca2+ exchange blocker on blood-brain barrier opening. Biochem. Biophys. Res. Commun., 2002, 291, 669-674.
26. Wang, M.; Etu, J.; Joshi, S. Enhanced disruption of the blood brain barrier by intracarotid mannitol injection during transient cerebral hypoperfusion in rabbits. J. Neurosurg. Anesthesiol., 2007, 19, 249-256.
27. Chen, X.; Bao, J.; Guo, J.; Ding, Q.; Lu, J.; Huang, M.; Wang, Y. Biological activities and potential molecular targets of cucurbitacins: a focus on cancer. Anticancer Drugs 2012, 23, 777-787.
28. Alghasham, A. A. Cucurbitacins - a promising target for cancer therapy. Int. J. Health Sci., 2013, 7, 77-89.
29. Tatli, I.I.; Akdemir, Z.S.; Bedir, E.; Khan, I.E.; Saponin, iridoid, phenylethanoid and monoterpene glycosides from Verbascum pterocalycinum var. Mutense. Turk J. Chem., 2004, 28, 111-122.
30. Crombie, L.; King, R. W.; Whiting, D. A. Carbon-13-magnetic resonance spectra. Synthetic presqualene esters, related cyclopropanes and isoprenoids. J. Chem. Soc. Perkin Trans., 1975, 1, 913-915.
31. Tundis, R.; Loizzo, M.R.; Menichini, F.; Statti, G.A.; Menichini, F. Biological and pharmacological activities of iridoids: recent developments. Mini Rev. Med. Chem., 2008, 8, 399-420.
32. Dinda, B.; Chowdhury, D.R.; Monhata, B.C. Naturally occuring iridoids, secoiridoids and their bioactivity. An update review, part 3. Chem. Pharm. Bull. (Tokyo), 2009, 58, 765-796.
33. Jansen, S.R. Plant iridoids, their biosynthesis and distribution in angiosperms. Ecological chemistry and biochemistry of plant terpenoids. Clarence Press: 1991, 133-158.
34. Bianco, A.; Marini, E.; Nicoletti, S. F.; Garbarino, J.; Piovano, M.; Chamy, M. Bis-iridoid glucosides from the roots of Argylia radiate. Phytochemistry, 1992, 31, 4203-4206.
35. Damtoft, S. Biosynthesis of catalpol. Phytochemistry, 1994, 35, 1187-1189.
36. Ronsted, N.; Gobel, E.; Franzyk, H.; Jansen, S. R.; Olsen, C. E. Chemotaxonomy of Plantago. Iridoid glucosides and caffeoyl phenylethanoid glycosides. Phytochem., 2000, 55, 337-348.
37. Singh, G.; Rawat, P.; Maurya, R. Constituents of Cissus quadrangularis. Nat. Prod. Res., 2007, 21, 522-528.
38. Young, H.S.; Kim M.S.; Park, H.J.; Chung, H.Y.; Choi, J.S. Phytochemical study on Catalpa ovate. Arch. Pharm. Res., 1992, 15(4), 322-327.
39. Sticher, O.; Afifi-Yazar, F. U. Minecoside and verminoside, two new iridoid glucosides from Veronica officinalis L. (Scrophulariaceae). Helv. Chim. Acta., 1979, 62, 535-539.
40. Niyonzima, G.; Pieters, L.; Balde, A.M.; Claeys, M.; Laekeman, G.M.; Vlietinck, A. J. Isolation of 6-O-Caffeoyl catalpol and some other compounds from Spathodea campanulata. Planta Med., 1991, 57, 85-A86.
41. Elusiyan, C.A.; Ani N.C.; Adewunmi, C.O.; Olugbade, T.A. Distribution of Iridiod glucosides and anti-oxidant compounds in Spathodea Campanulata Parts. Afr. J. Tradit. Complement Altern. Med., 2011, 8, 27-33.
42. Calis, I.; Kirmizibekmez, H.; Sticher, O. Iridoid Glycosides from Globularia trichosantha. J. Nat. Prod., 2001, 64, 60-64.
43. Compadre C.M.; Jauregui, J.F., Nathan, P.J.; Enriguez, R.G.; Isolation of 6-O-(p-coumaroyl)-catalpol from Tabebuia rosea. Planta Med., 1982, 46, 42-44.
44. Rastogi, R.P.; Sen, A.B.; Dhar, M.L. Constitution of Kutkin, the Bitter Glucoside of Picrorhiza kurroa Benth. J. Sci. Industr. Res., 1955, 14B, 512-519.
45. Basu, K.; Gupta, B.D.; Ghosal, S. Structure of kutkin, the bitter glucoside of Picrorhiza kurroa Royle ex Benth. J. Org. Chem., 35, 1970, 3159-3161.
46. Singh, G.B.; Bani, S.; Singh, S.; Khajuria, A.; Sharma, M.L.; Gupta, B.D.; Banerjee S. K. Anti-inflammatory activity of iridoids Kutkin, Picroside 1 and Kutkoside from Picrorhiza kurrooa. Phytother. Res., 1993, 7, 402-407.
47. Upadhyay, D.; Prasad, P.D.; Anandjiwala, S.; Nivasrkar M. Comparative pharmacokinetic profiles of picrosides I and II from kutkin, Picrorhiza kurroa extract and its formulation in rats. Fitoterapia, 2013, 85, 76-83.
48. Stefanska, J.; Pawliczak, R. Apocynin: Molecular Aptitudes. Mediators of Inflammation. 2008,1-10. http://dx.doi.org/10.1155/2008/106507
49. Huang, S.; Liao, X.; Nie, Q.; Ding, L.; Peng. S. Phenyl and phenylethyl glycosides from Picrorhiza scrophulariiflora. Helv. Chim. Acta., 2004, 87, 598-604.
50. Dorsch, W.; Muller, A.; Christoffel, V.; Stuppner, H.; Antus, S.; Gottsegen, A.; Wagner, H. Antiasthmatic acetophenones-an in vivo study on structure activity relationship. Phytomedicine, 1994, 1, 47-54.
51. Kumar, N.; Kumar, T.; Sharma, S. K. Phytopharmacological review on genus Picrorhiza. Int. J. Universal Pharmacy Bio Sci., 2013, 2, 334-347.
52. Kant, K.; Walia, M.; Agnihotri, V.K.; Pathania, V.; Singh, B. Evaluation of antioxidant activity of Picrorhiza Kurroa (Leaves) extracts. Indian J. Pharm. Sci., 2013, 75, 324-329.
53. Hans, L. Picein and piceol concentrations in Norway spruce. Ecotoxicol. Environ. Saf., 1990, 19, 301-309.
54. Liu, M.; Yang, S.; Jin, L.; Hu, D.; Wu, Z.; Yang, S. Chemical constituents of the ethyl acetate extract of Belamcanda chinensis (L.) DC roots and their antitumor activities. Molecules, 2012, 17, 6156-6169.
55. Zira, A.; Magiatis, P.; Haroutounian, S.A.; Skaltsounis, A.L.; Mikros, E. 1H NMR-based metabonomics for the classification of Greek wines according to variety, region and vintage. Comparison with HPLC Data. J. Agric. Food Chem., 2009, 57(23), 11067-11074.
56. Burns, D.C.; Ellis, D.A.; March, R.E. A predictive tool for assessing 13C NMR chemical shifts of flavonoids. Magn. Reson. Chem., 2007, 45, 835-845.
57. Owen, R. W.; Haubner, R.; Mier, W.; Giacosa, A.; Hull, W. E.; Spiegelhalder, B.; Bartsch, H. Isolation, structure elucidation and antioxidant potential of the major phenolic and flavonoid compounds in brined olive drupes. Food Chem. Toxicol., 2003, 41, 703-717.
58. Svehlikova, V.; Bennett, R. N.; Mellon, F.A.; Needs, P. W.; Piacente, S.; Kroon, P. A.; Bao, Y. Isolation, identification and stability of acylated derivatives of apigenin 7-O-glucoside from chamomile (Chamomilla recutita [L.] Rauschert). Phytochem, 2004, 65, 2323-2332.
59. Bochkov, D.V.; Sysolyatin, S.V.; Kalashnikov, A.I.; Surmacheva, I.A. Shikimic acid: review of its analytical, isolation, and purification techniques from plant and microbial sources. J. Chem. Biol., 2012, 5, 5-17.
60. Mulas, G.; Galaffu, M. G.; Pretti, L.; Nieddu, G.; Mercenaro, L.; Tonelli, R.; Anedda, R. NMR analysis of seven selections of vermentino grape berry: Metabolites composition and development. J. Agric. Food Chem., 2011, 59, 793-802.
61. Usuki, T.; Yasuda, N.; Yoshizawa-Fujita, M.; Rikukawa, M. Extraction and isolation of shikimic acid from Ginkgo biloba leaves utilizing an ionic liquid that dissolves cellulose. Chem. Commun. (Camb)., 2011, S1-S9.
62. Gahlan, P.; Russiachand, S.H.; Shankar, R.; Sharma, N.; Kumari, A.; Chawla, V.; Ahuja, P.S.; Kumar, S. De novo sequencing and characterization of Picrorhiza kurrooa transcriptome at two temperatures showed major transcriptome adjustments. BMC Genomics, 2012, 13, 126.
63. Dewick, P.M. The shikimate pathway: aromatic amino acids and phenylpropanoids. Medicinal natural products. John Wiley & Sons, Ltd. 2002, 4.
64. Damtoft, S.; Jensen, S. R.; Nielsen, B. Iridoid glycosides from Utricularia australis and Pinguicula vulgaris (Lentibulariaceae). Phytochem, 1985, 24, 2281-2283.
65. Sarg, T.; Salama, O.; El-Domiaty, M.; Bishr, M.; El, S.; Mansour, S. S.; Weight, E. Iridoid glucosides from Gentiana kurroo Royle. Alexandria J. Pharm. Sci., 1991, 5, 82-86.
66. Bhandari, P.; Kumar, N.; Singh, B.; Ahuja, P.S. Online HPLCDPPH method for antioxidant activity of Picrorhiza kurroa Royle ex Benth. and characterization of kutkoside by Ultra-Performance LC-electrospray ionization quadrupole time-of-flight mass spectrometry. Indian J. Exp. Biol., 2010, 48, 323-328.