Planta Med 2004; 70(9): 834-840
DOI: 10.1055/s-2004-827232
Original Paper
Physiology, in vitro Biotechnology
© Georg Thieme Verlag KG Stuttgart · New York

Phenylethanoid Glucosides from in vitro Propagated Plants and Callus Cultures of Plantago lanceolata

Anna Budzianowska1 , Lutosława Skrzypczak1 , Jaromir Budzianowski1
  • 1Department of Pharmaceutical Botany, K. Marcinkowski University of Medical Sciences, Poznań, Poland
Part of doctoral thesis of A.B.
Further Information

Publication History

Received: January 9, 2004

Accepted: June 13, 2004

Publication Date:
23 September 2004 (online)

Abstract

The well-known medicinal plant Plantago lanceolata L. (ribwort plantain) was effectively propagated by direct organogenesis from segments of leaves and roots using MS medium supplemented with IAA (11.42 μM), kinetin (9.29 μM) for multiplication and IAA (5.71 μM) for rooting. The plantlets were successfully hardened (80 %) and transferred to field cultivation (100 %). Two lines of callus tissue, derived from leaves and roots, were obtained on MS medium without NH4NO3 and supplemented with 2,4-D (4.52 μM) and kinetin ( 0.46 μM). From plant materials - leaf rosettes from in vitro, leaves from plants in field cultivation obtained by micropropagation, root-derived callus and leaf-derived callus - sixteen phenylethanoid glucosides representing nine different structures were isolated and identified by spectral methods (1D and 2D NMR) as known for the species: lavandulifolioside (1), plantamajoside (2,) acteoside (3); new for the species: leucosceptoside A (4), martynoside (5), desrhamnosylisoacteoside (6), plantainoside D (7), desrhamnosylacteoside (8) and - 2-(4-hydroxyphenyl)ethyl β-D-glucopyranosyl-(1→3)-4-O-trans- and cis-p-coumaroyl-β-D-glucopyranoside (9) - the latter also being found for the first time in nature and named lancetoside. Only plantamajoside (2) and acteoside (3) were common to all plant materials, the former was the main constituent of calli (1.19 - 2.84 % of dry weight), while the latter was the main constituent of the leaves (1.78 - 10.43 % of dry weight). Flavonoids were present only in plants of field cultivation.

References

  • 1 Paper D H, Marchesan M. Spitzwegerich (Plantago lanceolata L.) Inhaltsstoffe - Analytik - Pharmakologie - Standardisierung.  Zeit Phytother. 1999;  20 231-8
  • 2 Murai M, Tamayama Y, Nishibe S. Phenylethanoids in the herb of Plantago lanceolata and inhibitory effect on arachidonic acid-induced mouse ear edema.  Planta Medica. 1995;  61 479-80
  • 3 Bräutigam M, Franz G. Versuche zur Gewebekultur von schleimbildenden pflanzlichen Geweben.  Sci Pharm. 1985;  53 237-46
  • 4 Fons F, Gargadennec A, Gueiffier A, Roussel J L, Andary C. Effects of cinnamic acid on polyphenol production in Plantago lanceolata .  Phytochemistry. 1998;  49 697-702
  • 5 Fons F, Tousch D, Rapior S, Gueiffier A, Roussel J L, Gargadennec A, Andary C. Phenolic profiles of untransformed and hairy root cultures of Plantago lanceolata .  Plant Physiol Biochem. 1999;  37 291-6
  • 6 Murashige T, Skoog F. A revised medium for rapid growth and bioassays with tobacco tissue cultures.  Physiol Plant. 1962;  15 473-97
  • 7 Budzianowski J, Skrzypczak L. Phenylpropanoid esters from Lamium album flowers.  Phytochemistry. 1995;  38 997-1001
  • 8 Mederos S, Martin C, Navarro E, Ayuso M J. Micropropagation of a medicinal plant, Plantago major L.  Biologia Plantarum. 1997/98;  40 465-8
  • 9 Saker M M, Kawashity S A. Tissue culture and flavonoid content of Nepeta and Plantago species endemic in Egypt.  Fitoterapia. 1998;  69 358-64
  • 10 Chang I D, Locy R D. In vitro regeneration of plants of the halophyte Plantago maritima L. from primary explants and callus cultures.  In Vitro Cellular and Developmental Biology (Program Issue World Congress on In Vitro Biology, San Francisco 1996). 1996;  32 91A
  • 11 Makowczynska J, Andrzejewska-Golec E. Somatic embryogenesis in in vitro culture of Plantago asiatica L.  Acta Soc Bot Pol. 2000;  69 245-50
  • 12 Chowdhury A R, Kundu S, Raychaudhuri S S. Regeneration of Plantago ovata Forssk through somatic embryogenesis.  Cytobios. 1996;  85 255-61
  • 13 Basaran A A, Çalis I, Anklin A, Nishibe S, Sticher O. Lavandulifolioside: a new phenylpropanoid glycoside from Stachys lavandulifolia .  Helv Chim Acta. 1988;  71 1483-90
  • 14 Ravn H, Nishibe S, Sasahara M, Xuebo L. Phenolic compounds from Plantago asiatica L.  Phytochemistry. 1990;  29 3627-31
  • 15 Sasaki H, Nishimura H, Chin M, Mitsuhashi H. Hydroxycinnamic acid esters of phenethylalcohol glycosides from Rehmannia glutinosa var. purpurea .  Phytochemistry. 1989;  28 875-9
  • 16 Çalis I, Lahloub M F, Rogenmoser E, Sticher O. Isomartynoside, a phenylpropanoid glycoside from Galeopsis pubescens .  Phytochemistry. 1984;  23 2313-5
  • 17 Shimomura H, Sashida Y, Adachi T. Phenolic glucosides from Prunus grayana .  Phytochemistry. 1987;  26 249-51
  • 18 Miyase T, Ishino M, Akahori C, Ueno A, Ohkawa Y, Tanizawa H. Phenylethanoid glycosides from Plantago asiatica .  Phytochemistry. 1991;  30 2015-8
  • 19 Nishimura H, Sasaki H, Inagaki N, Chin M, Mitsuhashi H. Nine phenethyl alcohol glycosides from Stachys sieboldii .  Phytochemistry. 1991;  30 965-9
  • 20 Sugiyama M, Kikuchi M. Phenylethanoid glycosides from Osmanthus asiaticus .  Phytochemistry. 1993;  32 1553-5
  • 21 Andary C, Motte-Florac M E, Gargadennec A, Wylde R, Heitz A. Les esters caféiques du genre Plantago. Identification et valeur chimiotaxinomique.  Plantes médicinales et phytothérapie. 1988;  22 17-22
  • 22 Tamura Y, Nishibe S. Changes in the concentrations of bioactive compounds in plantain leaves.  J Agric Food Chem. 2002;  50 2514-8

Dr. Anna Budzianowska

Department of Pharmaceutical Botany

K. Marcinkowski University of Medical Sciences

14 ul. Sw. Marii Magdaleny

61-861 Poznan

Poland

Phone: +48-61-852-9057

Fax: +48-61-852-9057

Email: abudzian@amp.edu.pl