Influence of growing conditions on metabolite profile of Ammi visnaga umbels with special reference to bioactive furanochromones and pyranocoumarins

Phytochemistry

Volumn 95, Issue , 2013, Pages 197-206

  Sellami, Hela Kallel ^a   Napolitano, Assunta ^b   Masullo, Milena ^b   Smiti, Samira ^a   Piacente, Sonia ^b   Pizza, Cosimo ^b  

^a FACULTÉ DES SCIENCES DE TUNIS   (Tunisia)

^b UNIVERSITY OF SALERNO   (Italy)

Author keywords

Ammi visnaga umbels; Furanochromones and pyranocoumarins; HPLC ESI IT MSn; HPLC ESI QqQ MS MS; Hydroponic culture; Hypoxia; Salinity

Indexed keywords

AMMI VISNAGA;

CHROMONE DERIVATIVE; FURAN DERIVATIVE; FURANOCHROMONE; OXYGEN; PLANT EXTRACT; PYRANOCOUMARIN DERIVATIVE; SODIUM CHLORIDE;

AMMI; AMMI VISNAGA UMBELS; ARTICLE; CHEMISTRY; ENVIRONMENT; FURANOCHROMONES AND PYRANOCOUMARINS; GROWTH, DEVELOPMENT AND AGING; HPLC-ESI/IT/MS(N); HPLC-ESI/QQQ/MS/MS; HYDROPONICS; HYPOXIA; INFLORESCENCE; ISOLATION AND PURIFICATION; METABOLISM; PHYSIOLOGICAL STRESS; SALINITY;

AMMI VISNAGA UMBELS; FURANOCHROMONES AND PYRANOCOUMARINS; HPLC-ESI/IT/MS(N); HPLC-ESI/QQQ/MS/MS; HYDROPONIC CULTURE; HYPOXIA; SALINITY;

AMMI; CHROMONES; ENVIRONMENT; FURANS; HYDROPONICS; INFLORESCENCE; OXYGEN; PLANT EXTRACTS; PYRANOCOUMARINS; SALINITY; SODIUM CHLORIDE; STRESS, PHYSIOLOGICAL;

EID: 84893756226     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2013.08.001     Document Type: Article

References (60)

1. Adamska, M., Kaczmarek, F., 1974. Occurrence of dihydroseselins in individual organs of Ammi visnaga cultivated in Poland. Herba Colonica 20, 35-39.
2. Abou-Mustafa, E.A., Saleh, N.A.M., Elgamal, M.H.A., Shalaby, N.M.M., Duddeck, H., 1990. A further contribution to the c-pyrone constituents of Ammi visnaga fruits. Planta Med. 56, 134. (Pubitemid 20124716)
3. Alongi, D.M., 2002. Present state and future of the world's mangrove forests. Environ. Conserv. 29, 331-349. (Pubitemid 35447371)
4. Appendino, G., Bianchi, F., Bader, A., Campagnuolo, C., Fattorusso, E., Taglialatela- Scafati, O., Blanco-Molina, M., Macho, A., Fiebich, B.L., Bremner, P., Heinrich, M., Ballero, M., Muäz, E., 2004. Coumarins from Opopanax chironium. New dihydrofuranocoumarins and differential induction of apoptosis by imperatorin and heraclenin. J. Nat. Prod. 67, 532-536. (Pubitemid 38533921)
5. Badawi, M.M., Fayez, M.B.E., 1967. Natural chromones. III. Nuclear magnetic resonance spectra of some natural and synthetic products. Indian J. Chem. 5, 93-96.
6. Balbaa, S.I., Zaki, A.Y., Abdel-Wahab, S.M., 1968. Active constituent of Ammi visnaga fruits collected at different stages of maturity. J. Pharm. Sci. United Arab Republic 9, 15-26.
7. Barkla, B.J., Vera-Estrella, R., Pantoja, O., 2013. Progress and challenges for abiotic stress proteomics of crop plants. Proteomics 13, 1801-1815.
8. BCEOM (Bureau central d′études pour les éuipements d′Outremer), 1995. Etude pour la sauvegarde du Parc National de l′Ichkeul. Rapport de 3è partie: Mesures et études spécifiques. Tunis, Fresenius Consult, CE Salzgitter and Studi, Minist?e de l0Environnementet et de l′Améagement du Territoire, ANPE, Tunis (Tun.), pp. 1-421.
9. Ben Taarit, M., Msaad, K., Hosni, K., Marzouk, B., 2011. Physiological changes and essential oil composition of clary sage (Salvia sclarea L.) rosette leaves as affected by salinity. Acta Physiol. Plant. 33, 153-162.
10. Casagranda, C., Boudouresque, C.F., 2007. Biomass of Ruppia cirrhosa and Potamogeton pectinatus in a Mediterranean brackish lagoon, Lake Ichkeul, Tunisia. Fund. Appl. Limnol. 168, 243-255. (Pubitemid 47515184)
11. Dat, J.F., Capelli, N., Folzer, H., Bourgeade Badot, P.M., 2004. Sensing and signallingduring plant flooding. Plant Physiol. Biochem. 42, 273-282.
12. Drexler, J.Z., Ewel, K.C., 2001. Effect of the 1997-1998 ENSO-related drought on hydrology and salinity in a Micronesian wetland complex. Estuaries 24, 347-356. (Pubitemid 32675732)
13. El-Fiky, F.K., Remmel, R.P., Staba, E.J., 1989. Ammi visnaga: Somatic embryoinduction and furanochromone production in embryos, seedlings, and plants. Planta Med. 55, 446-451.
14. Elgamal, M.H.A., Elewa, N.H., Elkhrisy, E.A.M., Duddeck, H., 1979. Carbon-13 nuclear magnetic resonance spectra. Part XI. Carbon-13 NMR chemical shifts and carbon-proton coupling constants of some furocoumarins and furochromones. Phytochemistry 18, 139-143.
15. Elgamal, M.H.A., Shalaby, N.M.M., El-Hagrassy, A.M., Toth, G., Simon, A., Duddeck, H., 1998. A further contribution to some c-pyrone constituents ofAmmi visnaga. Fitoterapia 69, 549-550. (Pubitemid 29019165)
16. Ghosal, S., Singh, S., Bhagat, M.P., Kumar, Y., 1982. Three chromones from bulbs of Pancratium biflorum. Phytochemistry 21, 2943-2946.
17. Gonzalez, A.G., Galindo, A., Mansilla, H., Gutierrez, A., 1981. Structure of maritimin, a sesquiterpene lactone fromArtemia maritima gallica. Phytochemistry 20, 2367-2369.
18. Gounot, M., Schoenenberger, A., 1967. Carte phyto-évologique de la Tunisie septentrionale, échelle 1/200000. Ann. Inst. Nat. Rech. Agron. Tunisie 40, 425-427.
19. Gouvea, D.R., Gobbo-Neto, L., Lopes, N.P., 2012. The influence of biotic and abiotic factors on the production of secondary metabolites in medicinal plants. In: Cechinel-Filho, V. (Ed.), Plant Bioactives and Drug Discovery: Principles, Practice, and Perspectives. John Wiley & Sons Inc., Hoboken New Jersey, pp. 419-452.
20. Gunaydin, K., Erim, F.B., 2002. Determination of khellin and visnagin in Ammi visnaga fruits by capillary electrophoresis. J. Chromatogr. A 954, 291-294. (Pubitemid 34310202)
21. Gunaydin, K., Beyazit, N., 2004. The chemical investigations on the ripe fruits of Ammi visnaga (Lam.) Lamarck growing in Turkey. Nat. Prod. Res. 18, 169-175. (Pubitemid 38213216)
22. Horchani, F., Aschi-Smiti, S., 2010. Prolonged root hypoxia effects on enzymes involved in nitrogen assimilation pathway in tomato plants. Plant Signaling Behav. 5, 1583-1589.
23. Jackson, M.B., 2002. Long-distance signalling from roots to shoots assessed: theflooding story. J. Exp. Bot. 53, 175-181. (Pubitemid 34140363)
24. Jain, S.M., Saxena, P.K., 2009. Protocols for in vitro cultures and secondary metabolite analysis of aromatic and medicinal plants. Methods in molecularbiology. Humana Press, New York.
25. Karawya, M.S., Sina, A., Nour, G., 1969. Determination of dihydroseselins in fruits and extracts of Ammi visnaga; Giza, Egypt. J. Pharm. Sci. 58, 1545-1547.
26. Kim, Y.K., Kim, Y.S., Ryu, S.Y., 2007. Antiproliferative effect of furanocoumarins from the root of Angelica dahurica on cultured human tumor cell lines. Phytother. Res. 21, 288-290.
27. Kim, M.K., Yang, D.H., Jung, M., Jung, E.H., Eom, H.Y., Suh, J.H., Min, J.W., Kim, U., Min, H., Kim, J., Han, S.B., 2011. Simultaneous determination of chromones and coumarins in Radix Saposhnikoviae by high performance liquid chromatography with diode array and tandem mass detectors. J. Chromatogr. A 1218, 6319-6330.
28. Kleiner, H.E., Xia, X., Sonoda, J., Zhang, J., Pontius, E., Abey, J., Evans, R.M., Moore, D.D., DiGiovanni, J., 2008. Effects of naturally occurring coumarins on hepatic drug-metabolizing enzymes in mice. Toxicol. Appl. Pharmacol. 232, 337-350.
29. Kondo, Y., Takemoto, T., 1972. Constituents of Cimicifuga species. VIII. Structure of cimifugin, new bitter principle from Cimicifuga simplex. Chem. Pharm. Bull. 20, 1940-1944.
30. Kopp, B., Kubelka, E., Reich, C., Robien, W., Kubelka, W., 1991. 4H-Chromenone glycosides from Eranthis hyemalis (L.) salisbury. javascript. Helv. Chim. Acta 74, 611-616.
31. Kovacs, J.M., Wang, J., Blanco-Correa, M., 2001. Mapping disturbances in a mangrove forest using multi-data landsat TM imagery. Environ. Manage. 27, 763-776. (Pubitemid 32332568)
32. Króaicka, A., Staniszewska, I., Maliński, E., Szafranek, J., Lojkowska, E., 2003. Stimulation of furanochromone accumulation in callus cultures of Ammi visnaga L. by addition of elicitors. Pharmazie 58, 590-592. (Pubitemid 37012243)
33. Kursinszki, L., Troilina, J., Szõke, E., 1998. Determination of visnagin in Ammi visnaga hairy root cultures using solid-phase extraction and high-performance liquid chromatography. Microchem. J. 59, 392-398. (Pubitemid 128419249)
34. Li, W., Wang, Z., Sun, Y., Chen, L., Hand, L., Zheng, Y., 2011. Application of response surface methodology to optimise ultrasonic-assisted extraction of four chromones in Radix Saposhnikoviae. Phytochem. Anal. 22, 313-321.
35. Li, Y., Zhao, L., Zhang, H., Jia, J., Lv, L., Zhou, G., Chai, Y., Zhang, G., 2012. Comparative pharmacokinetics of prim-O-glucosylcimifugin and cimifugin by liquid chromatography-mass spectrometry after oral administration of Radix Saposhnikoviae extract, cimifugin monomer solution and prim-Oglucosylcimifugin monomer solution to rats. Biomed. Chromatogr. 26, 1234-1240.
36. Liu, R., Wu, S., Sun, A., 2008. Separation and purification of four chromones from Radix Saposhnikoviae by high-speed counter-current. Chromatogr. Phytochem.Anal. 19, 206-211. (Pubitemid 351722093)
37. Macias, F.A., Massanet, G.M., Rodriguez-Luis, F., Salva, J., Fronczek, F.R., 1989. Carbon-13 NMR of coumarins. II. Khellactones: spectroscopic criteria to establish the relative configuration of the dihydropyran ring. Magn. Res.Chem. 27, 653-658.
38. Mancini, P., Rodighiero, P., Pastorini, G., Guiotto, A., 1987. Proton NMR spectra of pyranocoumarins. Magn. Reson. Chem. 25, 740-742.
39. Máquez, N., Sancho, R., Ballero, M., Bremner, P., Appendino, G., Fiebich, B.L., Heinrich, M., Muñoz, E., 2004. Imperatorin inhibits T-cell proliferation by targeting the transcription factor NFAT. Planta Med. 70, 1016-1021. (Pubitemid 39587033)
40. Martelli, P., Bovalini, L., Ferri, S., Franchi, G.G., 1984. Rapid separation and quantitative determination of khellin and visnagin in Ammi visnaga (L.) Lam. fruits by highperformance liquid chromatography. J. Chromatogr. 301, 297-302.
41. Marumoto, S., Miyazawa, M., 2010. b-secretase inhibitory effects of furanocoumarins from the root of Angelica dahurica. Phytother. Res. 24, 510-513.
42. Mendez, J., Rubido, J., 1979. Coumarins of Angelica pachycarpa fruits. javascript. Planta Med. 36, 219-220.
43. Miftakhova, A.F., Burasheva, G.Sh., Abilov, Zh.A., Ahmad, V.U., Zahid, M., 2001. Coumarins from the aerial part of Halocnemum strobilaceum. Fitoterapia 72, 319-321. (Pubitemid 32273483)
44. Munns, R., 2005. Genes and salt tolerance: bringing them together. New Phytol. 167, 645-663. (Pubitemid 43923804)
45. Napolitano, A., Akay, S., Mari, A., Bedir, E., Pizza, C., Piacente, S., 2013. An analytical approach based on ESI-MS, LC-MS and PCA for the qualiquantitative analysis of cycloartane derivatives in Astragalus spp. J. Pharm. Biomed. Anal. 85C, 46-54.
46. Niccolai, N., Bovalini, L., Martelli, P., 1986. The mechanisms of interaction between furanochromones and DNA. A heteronuclear overhauser effect study on the khellin-thymidine model system. Biophys. Chem. 24, 217-220. (Pubitemid 16004625)
47. Pederson, O., Vos, H., Colmer, T.D., 2006. Oxygen dynamics during submergence in the halophytic stem succulent Halosarcia pergranulata. Plant, Cell Environ. 29, 1388-1399. (Pubitemid 43855755)
48. Pedneault, K., Leonhart, S., Gosselin, A., Angers, P., Papadopoulos, A.P., Dorais, M., 2002. Variations in concentration of active compounds in four hydroponicallyand field-grown medicinal plant species. Acta Horticulturae 580, 255-262.
49. Perrone, A., Muzashvili, T., Napolitano, A., Skhirtladze, A., Kemertelidze, E., Pizza, C., Piacente, S., 2009. Steroidal glycosides from the leaves of Ruscus colchicus: Isolation and structural elucidation based on a preliminary liquid chromatography-electrospray ionization tandem mass spectrometry profiling. Phytochemistry 70, 2078-2088.
50. Petinatti Pavarini, D., Petinatti Pavarini, S., Niehues, M., Peporine Lopes, N., 2012. Exogenous influences on plant secondary metabolite levels. Anim. Feed Sci. Technol. 176, 5-16.
51. Saglio, P.H., Pradet, A., 1980. Soluble sugars, respiration, and energy charge during aging of excised maize root tips. Plant Physiol. 66, 516-519.
52. Supniewska, H., 1956. Ammi visnaga. II. Determination of khelline content in plants cultivated in Poland. Dissert. Pharm. 8, 63-74.
53. Supniewska, H., 1957. Khellin content in Ammi visnaga adapted to Polish climatic conditions. B. Acad. Pol. Sci. Biol. 5, 67-70.
54. Um, Y.R., Kong, C.-S., Lee, J.I., Kim, Y.A., Nam, T.J., Seo, Y., 2010. Evaluation of chemical constituents from Glehnia littoralis for antiproliferative activity against HT-29 human colon cancer cells. Process Biochem. 45, 114-119.
55. UNEP-WCMC (United Nations Environment Programme-World Conservation Monitoring Centre). 2008. Ichkeul National Park, Tunisia. Available from: http://www.eoearth.org/article/Ichkeul-National-Park,-Tunisia.
56. Van Dongen, K., 1952. The action of khellin on fibrillation of the heart. Arch. Int. Pharmacodyn. Ther. 88, 458-460.
57. Vij, S., Tyagi, A.K., 2007. Emerging trends in the functional genomics of the abiotic stress response in crop plants. Plant Biotechnol. J. 5, 361-380. (Pubitemid 46558322)
58. Voesenek, L.A., Colmer, T.D., Pierik, R., Millenaar, F.F., Peeters, A.J., 2006. How plants cope with complete submergence. New Phytol. 170, 213-226.
59. Zgáka, G., Dragan, T., Glowniak, K., Basiura, E., 1998. Determination of furanochromones and pyranocoumarins in drugs and Ammi visnaga fruits by combined solid-phase extraction-high-performance liquid chromatography and thin-layer chromatography-high-performance liquid chromatography. J. Chromatogr. A 797, 305-309. (Pubitemid 28156973)
60. Zheng, Z.G., Wang, R.S., Cheng, H.Q., 2011. Isolated perfused lung extraction and HPLC-ESIMSn analysis for predicting bioactive components of Saposhnikoviae Radix. J. Pharm. Biomed. Anal. 54, 614-618.