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2013 | 60 | 3 | 467-473
Article title

Production of oleanolic acid glycosides by hairy root established cultures of Calendula officinalis L.

Content
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EN
Abstracts
EN
In order to initiate hairy root culture initiation cotyledons and hypocotyls of Calendula officinalis L. were infected with Agrobacterium rhizogenes strain ATCC 15834 or the same strain containing pCAMBIA 1381Z vector with β-glucuronidase reporter gene under control of promoter of NIK (Nematode Induced Kinase) gene. The efficiency of induction of hairy roots reached 33.8% for cotyledons and 66.6% for hypocotyls together for both transformation experiments. Finally, eight control and nine modified lines were established as a long-term culture. The hairy root cultures showed the ability to synthesize oleanolic acid mainly (97%) as glycosides; control lines contained it at the average 8.42 mg · g-1 dry weight in tissue and 0.23 mg · dm-3 in medium; modified lines: 4.59 mg · g-1 for the tissue, and 0.48 mg · dm-3 for the medium. Additionally lines showed high positive correlation between dry/fresh weight and oleanolic acid concentration in tissue. Using the Killiani mixture in acidic hydrolysis of oleanolic acid glycosides released free aglycones that were partially acetylated in such conditions.
Year
Volume
60
Issue
3
Pages
467-473
Physical description
Dates
published
2013
received
2013-04-23
revised
2013-07-05
accepted
2013-07-13
(unknown)
2013-09-13
References
  • Andersen F, Bergfeld W, Belsito D, Hill R, Klaassen C, Liebler D, Marks J, Shank R, Slaga T, Snyder P (2010) Final report of the Cosmetic Ingredient Review Expert Panel amended safety assessment of Calendula officinalis-derived cosmetic ingredients. Int J Toxicol 29: 221S-243S.
  • Assefa H, Nimrod A, Walker L, Sindelar R (1999) Synthesis and evaluation of potential complement inhibitory semisynthetic analogs of oleanolic acid. Bioorg Med Chem Lett 9: 1889-1894.
  • Dedio I, Kozłowski J (1998) Influence of climate and fertilization on the content of oleanolic acid in inflorescences marigold Calendula officinalis L. Herba Pol 44: 103-107 (in Polish).
  • Długosz M, Wiktorowska E, Janiszowska W (2009) Induction of hairy roots in Calendula officinalis capable of biosynthesizing oleanolic acid glycosides. Acta Biochim Polon 56 (Suppl 2:) 73-74.
  • Doligalska M, Jóźwicka K, Kiersnowska M, Mroczek A, Pączkowski C, Janiszowska W (2011) Triterpenoid saponins affect the function of P-glycoprotein and reduce the survival of the free-living stages of Heligmosomoides bakeri. Vet Parasitol 179: 144-151.
  • EMEA (1999) (The European Agency for the Evaluation of Medicinal Products). C. officinalis (use in veterinary homeopathy). Summary Report. EMEA/MRL/683/99/FINAL, August 1999.
  • Grzelak A, Janiszowska W (2002) Initiation and growth characteristic of suspension culture of Calendula officinalis cells. Plant Cell Tiss Org Cult 71: 29-40.
  • Guillon S, Trémouillaux-Guiller J, Pati PK, Rideau M, Gantet P (2006) Harnessing the potential of hairy roots: dawn of a new era. Trends Biotechnol 24: 403-409.
  • Guinot P, Gargadennec A, Valette G, Fruchier A, Andary C (2008) Primary flavonoids in marigold dye: extraction, structure and involvement in the dyeing process. Phytochem Anal 19: 46-51.
  • Janiszowska W, Kasprzyk Z (1977) Intracellular distribution and origin of pentacyclic triterpenes in Calendula officinalis leaves. Phytochem 16: 1919-1923.
  • Jefferson RA, Kavanagh TA, Bevan MW (1987) GUS-fusions: β-glucuronidase as a sensitive and versatile gene fusion marker in higher plants. EMBO J 6: 3901-3907.
  • Kashiwada Y, Wang HK, Nagao T, Kitanaka S, Yasuda I, Fujioka T (1998) Anti-AIDS agents. Anti-HIV activity of oleanolic acid, pomolic acid, and structurally related triterpenoids. J Nat Prod 61: 1090-1095.
  • Kasprzyk Z, Fonberg-Broczek M (1967) The changes of the level of triterpenoids in Calendula officinalis during vegetation. Physiol Plant 20: 321-329.
  • Killiani H (1930) Uber Digitalinum Verum. Bet. Deutsch Chem. Ges 63: 2866-2869.
  • Kowalski R (2007) Studies of selected plant raw materials as alternative sources of triterpenes of oleanolic and ursolic acid types. J Agric Food Chem 55: 656-662.
  • Lin-Shiang S, Shih-Yow H (2006) Lateral root bridging as a strategy to enhance L-DOPA production in Stizolobium hassjoo hairy root cultures by using a mesh hindrance mist trickling bioreactor. Biotechnol and Bioenerg 94: 441-447.
  • Liu J (1995) Pharmacology of oleanolic acid and ursolic acid. J Ethnopharmacol 49: 57-68.
  • Liu J (2005) Oleanolic acid and ursolic acid: Research perspectives. J Ethnopharmacol 100: 92-94.
  • Mrugasiewicz K, Lutomski J, Mścisz A (1979) Method for determination of oleanosides in Calendula officinalis L. Herba Pol 25: 107-112 (in Polish).
  • Muley BP, Khadabadi SS, Banarase NB (2009) Phytochemical constituents and pharmacological activities of C. officinalis Linn (Asteraceae): A review. Trop J Pharm Res 8: 455-465.
  • Murashige T, Skoog F (1962) A revised medium for rapid growth and bioassays with tobacco tissue cultures. Physiol Plant 15: 473-497.
  • Piccaglia, R, Venturi G (1998) Dye plants: a renewable source of natural colours. Agro Food Ind Hi-Tech 9: 27-30.
  • Pellegrino AP, Joaquim DRG, Shepherd SLK (1992) In vitro culture of four medicinal Asteraceae species for Agrobacterium rhizogenes transformation. Acta Hort 502: 299-302.
  • Re TA, Mooney D, Antignac E, Dufour E, Bark I, Srinivasan V, Nohynek G (2009) Application of the threshold of toxicological concern approach for the safety evaluation of calendula flower (Calendula officinalis) petals and extracts used in cosmetic and personal care products. Food Chem Toxicol 47: 1246-1254.
  • Święcicka M, Filipecki M, Lont D, Van Vliet J, Qin L, Goverse A, Bakker J, Helder J (2009) Dynamics in the tomato root transcriptome on infection with the potato cyst nematode Globodera rostochiensis. Mol Plant Pathol 10: 487-500.
  • Szakiel A, Pączkowski C, Henry M (2011) Influence of environmental abiotic factors on the content of saponins in plants. Phytochem Rev 10: 471-491.
  • Szakiel A, Ruszkowski D, Grudniak A, Kurek A, Wolska K, Doligalska M (2008) Antibacterial and antiparasitic activity of oleanolic acid and its glycosides isolated from marigold (Calendula officinalis). Planta Med 74: 1709-1715.
  • Szakiel A, Ruszkowski D, Janiszowska W (2005) Saponins in Calendula officinalis L. - structure, biosynthesis, transport and biological activity. Phytochem Rev 4: 151-158.
  • Triplett BA, Moss SC, Bland JM, Dowd MK (2008) Induction of hairy root cultures from Gossypium hirsutum and Gossypium barbadense to produce gossypol and related compounds. In Vitro Cell Dev-Plant 44: 508-517.
  • Wiktorowska E, Długosz M, Janiszowska W (2010) Significant enhancement of oleanolic acid accumulation by biotic elicitors in cell suspension cultures of Calendula officinalis L. Enzyme Microb Technol 46: 14-20.
  • Yoo KH, Park J-H, Cui EJ, Kim KI, Kim JY, Kim J, Hong SG, Baek NI, Chung IS (2012) 3-O-acetyloleanolic acid induces apoptosis in human colon carcinoma Hct-116 cells. Phytother Res published online 10.1002/ptr.4616.
  • Zhang YN, Zhang W, Hong D, Shi L, Shen Q, Li JY, Li J, Hua LH (2008) Oleanolic acid and its derivatives: New inhibitor of protein tyrosine phosphatase 1B with cellular activities. Bioorg Med Chem 16: 8697-8705.
  • Zhu YM, Shen JK, Wang HK, Cosentino LM, Lee KH (2001) Synthesis and anti-HIV activity of oleanolic acid derivatives. Bioorg Med Chem Lett 11: 3115-3118.
Document Type
Publication order reference
YADDA identifier
bwmeta1.element.bwnjournal-article-abpv60p467kz
Identifiers
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