Caffeic acid derivatives from a hairy root culture of Lactuca virosa

• Autorzy: Stojakowska A. , Malarz J. , Szewczyk A. , Kisiel W.
• Języki publikacji: EN

Abstrakty

EN

In a search for biologically active phenolics, a hydroalcoholic extract from the hairy roots of Lactuca virosa was fractionated by chromatographical methods. The procedure led to the isolation of a substantial amount of 3,5-dicaffeoylquinic acid (3,5-DCQA)—a potent free radical scavenger. An analytical RP-HPLC separation of the hydroalcoholic extract from the hairy roots allowed identification of further hydroxycinnamates: caftaric acid (CTA), chlorogenic acid (5-CQA) and cichoric acid (DCTA), as well as small amounts of unbound phenolic acids. A time course of growth and caffeic acid derivatives accumulation in the hairy root culture was also investigated. The highest contents of the compounds in the examined roots were detected at the logarithmic phase of growth. The average content of 3,5-DCQA in the roots (ca. 2.5% DW) was at least one order of magnitude higher than that found in roots of Lactuca species and callus culture of L. virosa.

• Wydawca: -
• Czasopismo: Acta Physiologiae Plantarum
• Rocznik: 2012
• Tom: 34
• Numer: 1
• Opis fizyczny: p.291-298,fig.,ref.

Twórcy

autor

Stojakowska A.

• Department of Phytochemistry, Institute of Pharmacology, Polish Academy of Sciences, 12 Smetna Street, 30-688 Krakow, Poland

autor

Malarz J.

• Department of Phytochemistry, Institute of Pharmacology, Polish Academy of Sciences, 12 Smetna Street, 30-688 Krakow, Poland

autor

Szewczyk A.

• Chair and Department of Pharmaceutical Botany, Faculty of Pharmacy, Jagiellonian University, Collegium Medicum, 9 Medyczna Street, 30-688 Krakow, Poland

autor

Kisiel W.

• Department of Phytochemistry, Institute of Pharmacology, Polish Academy of Sciences, 12 Smetna Street, 30-688 Krakow, Poland

Bibliografia

• Abbasi BH, Tian C-L, Murch SJ, Saxena PK, Liu C-Z (2007) Lightenhanced caffeic acid derivatives biosynthesis in hairy root cultures of Echinacea purpurea. Plant Cell Rep 26:1367–1372
• Basnet P, Matsushige K, Hase K, Kadota S, Namba T (1996) Four di-O-caffeoyl quinic acid derivatives from propolis. Potent hepatoprotective activity in experimental liver injury models. Biol Pharm Bull 19:1479–1484
• Cavin C, Delannoy M, Malnoe A, Debefve E, Touche A, Courtois D, Schilter B (2005) Inhibition of the expression and activity of cyclooxygenase-2 by chicory extract. Biochem Biophys Res Commun 327:742–749
• Chiang YM, Chuang D-Y, Wang S-Y, Kuo Y-H, Tsai P-W, Shyur L-F (2004) Metabolite profiling and chemopreventive bioactivity of plant extracts from Bidens pilosa. J Ethnopharm 95:409–419
• Degl’Innocenti E, Pardossi A, Tattini M, Guidi L (2008) Phenolic compounds and antioxidant power in minimally processed salad. J Food Biochem 32:642–653
• Ekiert H, Szewczyk A, Kuś A (2009) Free phenolic acids in Ruta graveolens L. in vitro culture. Pharmazie 64:694–696
• Ellnain-Wojtaszek M, Zgórka G (1999) High performance liquid chromatography and thin-layer chromatography of phenolic acids from Ginkgo biloba L. leaves collected within vegetative period. J Liq Chrom Tech 22:1457–1471
• Grass S, Zidorn C, Blattner FR, Stuppner H (2006) Comparative molecular and phytochemical investigation of Leontodon autumnalis (Asteraceae, Lactuceae) populations from Central Europe. Phytochemistry 67:122–131
• Hung TM, Na MK, Thuong PT, Su ND, Sok DE, Song KS, Seong YH, Bae KH (2006) Antioxidant activity of caffeoyl quinic acid derivatives from the roots of Dipsacus asper Wall. J Ethnopharm 108:188–192
• Islam MS, Yoshimoto M, Yahara S, Okuno S, Ishiguro K, Yamakawa O (2002) Identification and characterization of foliar polyphenolic composition in sweetpotato (Ipomea batatas L.) genotypes. J Agric Food Chem 50:3718–3722
• Jeong J-A, Wu C-H, Murthy HN, Hahn E-J, Paek K-Y (2009) Application of an airlift bioreactor system for the production of adventitious root biomass and caffeic acid derivatives of Echinacea purpurea. Biotechnol Bioprocess Eng 14:91–98
• Kim HJ, Lee YS (2005) Identification of new dicaffeoylquinic acids from Chrysanthemum morifolium and their antioxidant activities. Planta Med 71:871–876
• Kim S–S, Park R-Y, Jeon H-J, Kwon Y-S, Chun W (2005) Neuroprotective effects of 3,5-dicaffeoylquinic acid on hydrogen peroxide-induced cell death in SH-SY5Y cells. Phytother Res 19:243–245
• Kisiel W, Stojakowska A, Malarz J, Kohlmünzer S (1995) Sesquiterpene lactones in Agrobacterium rhizogenes-transformed hairy root culture of Lactuca virosa. Phytochemistry 40:1139–1140
• Kodoma M, Wada H, Otani H, Kohmoto K, Kimura Y (1998) 3,5-Di-O-caffeoylquinic acid, an infection-inhibiting factor from Pyrus pyrifolia induced by infection with Alternaria alternata. Phytochemistry 47:371–373
• Leiss KA, Maltese F, Choi YH, Verpoorte R, Klinkhamer PGL (2009) Identification of chlorogenic acid as a resistance factor for thrips in Chrysanthemum. Plant Physiol 150:1567–1575
• Li W–W, Barz W (2006) Structure and accumulation of phenolics in elicited Echinacea purpurea cell cultures. Planta Med 72:248–254
• Liu C-Z, Abbasi BH, Gao M, Murch SJ, Saxena PK (2006) Caffeic acid derivatives production by hairy root cultures of Echinacea purpurea. J Agric Food Chem 54:8456–8460
• Llorach R, Martínez-Sánchez A, Tomás-Barberán FA, Gil MI, Ferreres F (2008) Characterisation of polyphenols and antioxidant properties of five lettuce varieties and escarole. Food Chem 108:1028–1038
• McDougall B, King PJ, Wu B-W, Hostomsky Z, Reinecke MG, Robinson WE Jr (1998) Dicaffeoylquinic and dicaffeoyltartaric acids are selective inhibitors of human immunodeficiency virus type I integrase. Antimicrob Agents Chemother 42:140–146
• Murashige T, Skoog F (1962) A revised medium for rapid growth and bioassays with tobacco tissue cultures. Physiol Plant 15:473–497
• Nicolle C, Carnat A, Fraisse D, Lamaison J-L, Rock E, Michel H, Amouroux P, Remesy C (2004) Characterisation and variation of antioxidant micronutrients in lettuce (Lactuca sativa folium). J Sci Food Agric 84:2061–2069
• Ohnishi M, Morishita H, Iwahashi H, Toda S, Shirataki Y, Kimura M, Kido R (1994) Inhibitory effects of chlorogenic acids on linoleic acid peroxidation and haemolysis. Phytochemistry 36:579–583
• Olmos A, Giner RM, Recio MC, Ríos JL, Gil-Benso R, Máñez S (2008) Interaction of dicaffeoylquinic derivatives with peroxynitrite and other reactive nitrogen species. Arch Biochem Biophys 475:66–71
• Park KH, Park M, Choi SE, Jeong MS, Kwon JH, Oh MH, Choi HK, Seo SJ, Lee MW (2009) The anti-oxidative and anti-inflammatory effects of caffeoyl derivatives from the roots of Aconitum koreanum R. Raymond Biol Pharm Bull 32:2029–2033
• Pauli GF, Poetsch F, Nahrstedt A (1998) Structure assignment of natural quinic acid derivatives using proton nuclear magnetic resonance techniques. Phytochem Anal 9:177–185
• Pellati F, Benvenuti S, Magro L, Melegari M, Soragni F (2004) Analysis of phenolic compounds and radical scavenging activity of Echinacea spp. J Pharm Biomed Anal 35:289–301
• Ribas-Agustí A, Gratacós-CubarsíM, Sárraga C, García-Regueiro J -A, Castellari M (2011). Analysis of eleven phenolic compounds including novel p-coumaroyl derivatives in lettuce (Lactuca sativa L.) by ultra-high-performance liquid chromatography with photodiode array and mass spectrometry detection. Phytochem Anal. doi:10.1002/pca.1318
• Robinson WE Jr, Reinecke MG, Abdel-Malek S, Jia Q, Chow SA (1996) Inhibitors of HIV-1 replication that inhibit HIV integrase. Proc Natl Acad Sci 93:6326–6331
• Spitaler R, Schlorhaufer PD, Ellmerer EP, Merfort I, Bortenschleger S, Stuppner H, Zidorn C (2006) Altitudinal variation of secondary metabolite profiles in flowering heads of Arnica montana cv. ARBO Phytochem 67:409–417
• Stojakowska A, Kisiel W (2000) Neolignan glycosides from a cell suspension culture of Lactuca virosa. Pol J Chem 74:153–155
• Stojakowska A, Malarz J (2000) Flavonoid production in transformed root cultures of Scutellaria baicalensis. J Plant Physiol 156:121–125
• Stojakowska A, Malarz J, Kisiel W (1994) Sesquiterpene lactones in tissue culture of Lactuca virosa. Planta Med 60:93–94
• Stojakowska A, Malarz J, Kisiel W (1999) Lactuca virosa L. (bitter lettuce): In vitro culture and production of sesquiterpene lactones. In: Bajaj YPS (ed) Biotechnology in agriculture and forestry. Medicinal and aromatic plants XI, vol 43. Springer-Verlag, Heidelberg, pp 261–273
• Tamaki H, Robinson RW, Anderson JL, Stoewsand GS (1995) Sesquiterpene lactones in virus-resistant lettuce. J Agric Food Chem 43:6–8
• Tamura H, Akioka T, Ueno K, Chujyo T, Okazaki K-I, King PJ, Robinson WE Jr (2006) Anti-human immunodeficiency virus activity of 3, 4, 5-tricaffeoylquinic acid in cultured cells of lettuce leaves. Mol Nutr Food Res 50:396–400
• Wesołowska A, Nikiforuk A, Michalska K, Kisiel W, Chojnacka-Wójcik E (2006) Analgesic and sedative activities of lactucin and some lactucin-like guaianolides in mice. J Ethnopharmacol 107:254–258
• Wu C-H, Murthy HN, Hahn E-J, Paek KY (2007) Enhanced production of caftaric acid, chlorogenic acid and cichoric acid in suspension cultures of Echinacea purpurea by the manipulation of incubation temperature and photoperiod. Biochem Eng J 36:301–303
• Zha R-P, Xu W, Wang W-Y, Dong L, Wang Y-P (2007) Prevention of lipopolisaccharide-induced injury by 3,5-dicaffeoylquinic acid in endothelial cells. Acta Pharmacol Sin 28:1143–1148

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