Advertisement

Phytochemistry Reviews

, Volume 4, Issue 2–3, pp 151–158 | Cite as

Saponins in Calendula officinalis L. – Structure, Biosynthesis, Transport and Biological Activity

  • Anna Szakiel
  • Dariusz Ruszkowski
  • Wirginia Janiszowska
Article

Abstract

Trends in research on Calendula officinalis L. saponins performed in Department of Plant Biochemistry at Warsaw University are reviewed. Calendula officinalis, a well known medicinal plant, contains significant amounts of oleanane saponins, which form two distinct series of related compounds, called “glucosides” and “glucuronides” according to the structure of the respective precursor. Both series differ in the pathway of their biosynthesis and further metabolism, i.e. the rate of formation and stages of possible degradation; distribution in the single cell and in the whole plant, including accumulation sites; and the possible physiological role played in the plant according to appropriate biological activities.

Key words

biosynthesis oleanolic acid glycosides structure transport 

Abbreviations

ADP

adenosine 5′-diphosphate

ATP

adenosine 5′-triphosphate

Gal

galactose

Glc

glucose

GlcUA

glucuronic acid

MVA

mevalonic acid

OL

oleanolic acid

Pi

inorganic phosphate

PPi

inorganic pyrophosphate

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Anon,  2001Final report on the safety assessment of Calendula officinalis extract and Calendula officinalis Int. J. Toxicol.201320Google Scholar
  2. Barnes, J, Anderson, L, Philipson, J 2002Herbal MedicinesPharmaceutical PressLondon103106Google Scholar
  3. Bisset, NG, Wichtl, M 2001Herbal Drugs and PhytopharmaceuticalsCRC PressBoca Raton167Google Scholar
  4. Dajani, FZ, Bianchi, RG, Casler, JJ, Weet, JF 1979Gastric antiulcer and antisecretory effects of carbenoxolone, aldosterone and desoxycorticosterone in ratsArch. Int. Pharmacodyn.242128138PubMedGoogle Scholar
  5. Dargan, DJ, Subak-Sharpe, JH 1985The effect of triterpenoid compounds on uninfected and Herpes Simplex virus-infected cells in culture. I. Effect of cells growth, virus particles and virus replicationJ. Gen. Virol.6617711784PubMedCrossRefGoogle Scholar
  6. Eisenreich, W, Bacher, A, Arigoni, D, Rohdich, F 2004Biosynthesis of isoprenoids via the non-mevalonate pathwayCell. Mol. Life Sci.6114011426CrossRefPubMedGoogle Scholar
  7. Farina, C, Pinza, M, Pifferi, G 1998Synthesis and anti-ulcer activity of new derivatives of glycyrrhetic, oleanolic and ursolic acidIl Farmaco532232CrossRefPubMedGoogle Scholar
  8. Finney, RSH, Tarknoy, AI 1960The pharmacological properties of glycyrrhetinic acid hydrogen succinateJ. Pharm. Pharmacol.124953PubMedGoogle Scholar
  9. Grzelak, A, Janiszowska, W 2002Initiation and growth characteristics of suspension cultures of Calendula officinalis cellsPlant Cell Tiss. Org.712940Google Scholar
  10. Inoue, H, Kurosu, S, Takeuchi, T, Mori, T, Shibata, S 1990Glycyrrhetinic acid derivatives anti-nociceptive activity of deoxoglycyrrhetol dihemiphthalate and the related compoundsJ. Pharm. Pharmacol.42199200PubMedGoogle Scholar
  11. Janiszowska, W, Kasprzyk, Z 1974Transport of glycosides of oleanolic acid from shoot to root in Calendula officinalis Acta Biochim. Polon.16415421Google Scholar
  12. Janiszowska, W, Kasprzyk, Z 1977Intracellular distribution and origin of pentacyclic triterpenes in Calendula officinalis leavesPhytochemistry1619191923Google Scholar
  13. Janiszowska W, Jurzysta M & Kasprzyk Z (1987) Biological activities of oleanolic acid glycosides from Calendula officinalis. 13th Conference on Isoprenoids. Poznań, Poland. Abstacts p. 100.Google Scholar
  14. Janiszowska, W, Szakiel, A 1991The transport of [3−3H]oleanolic acid and its monoglycosides to isolated vacuoles of protoplasts from Calendula officinalis leavesPhytochemistry929932997Google Scholar
  15. Kasprzyk, Z, Wojciechowski, Z 1967The structure of triterpenic glycosides from the flowers of Calendula officinalis L.Phytochemistry66975CrossRefGoogle Scholar
  16. Kasprzyk, Z, Wojciechowski, Z, Janiszowska, W 1970Incorporation of 1−14C-acetate into glycosides of Calendula officinalis Phytochemistry9561564CrossRefGoogle Scholar
  17. Kasprzyk, Z, Janiszowska, W, Sobczyk, E 1973Metabolism of the new series of oleanolic acid glycosides in Calendula officinalis Acta Biochim. Polon.20231235PubMedGoogle Scholar
  18. Kohlmunzer, S 1998Pharmacognosis. Handbook for pharmacy studentsPZWLWarsaw319321Google Scholar
  19. Liu, J 1995Pharmacology of oleanolic acid and ursolic acid.J. Ethnopharmacol.495768CrossRefPubMedGoogle Scholar
  20. Mahato, SB, Nandy, AK, Roy, G 1992TriterpenoidsPhytochemistry3521992249Google Scholar
  21. Miles, DH, Kokpol, U, Zalkow, LH, Steindel, SJ, Nabors, JB 1974Tumor inhibitors. I. Preliminary investigation of antitumors activitity of Saracenia flava J. Pharmacol. Sci.63613615Google Scholar
  22. Nishino, H, Nishino, A, Takayasu, J, Hasegawa, T, Iwashima, A, Hitahahayashi, K, Iwata, S, Shibata, S 1988Inhibition of the tumor-promoting action of 12-O-tetradecanoylphorbol-13-acetate by some oleanane-type triterpenoid compoundsCancer Res.4852105215PubMedGoogle Scholar
  23. Oda, K, Matsuda, H, Murakami, T, Katayama, S, Ohgitani, T, Yoshikawa, M 2000Adjuvant and haemolytic activities of 43 saponins derived from medicinal and food plantsBiol. Chem.3816774CrossRefPubMedGoogle Scholar
  24. Paulsen, E 2002Contact sensitization from Compositae-containing herbal remedies and cosmeticsContact Derm.47189198PubMedGoogle Scholar
  25. Pauthe-Dayde, D, Rochd, M, Henry, M 1990Triterpenoid saponin production in callus and multiple shoot cultures of Gypsophilla spPhytochemistry29483487Google Scholar
  26. Pinducciu, G, Serra, C, Cagetti, MG, Cotti, M, Deida, D, Pinza, M 1995Selective antimicrobial activity of triterpene derivates on oral bacteriaMed. Microbiol. Lett.48390Google Scholar
  27. Ruszkowski, D, Szakiel, A, Janiszowska, W 2003Metabolism of [3−3H]oleanolic acid in Calendula officinalis L. rootsActa Physiol. Plant.25311317Google Scholar
  28. Ruszkowski D, Chołuj A, Doligalska M & Janiszowska W (2004a) The reduction of nematode infective stages viability under oleanolic acid glycosides of Calendula officinalis L. roots. International Conference on Saponins, Puławy, Poland. Abstracts p. 105.Google Scholar
  29. Ruszkowski D, Uniewicz K, Auguścińska E & Janiszowska W (2004b) The allelopathic properties of oleanolic acid 3-O-monoglucoside secreted by roots of Calendula officinalis to the soil. Second European Allelopathy Symposium, Puławy, Poland. Abstracts p. 101.Google Scholar
  30. Sashida, Y, Ogawa, K, Yamanouchi, T, Tanaka, H, Shoyama, I, Nishioka, I 1994Triterpenoids from callus tissue of Actinidia polygama Phytochemistry33377380Google Scholar
  31. Serra, C, Lampis, G, Pompei, R, Pinza, M 1994Antiviral activity of new triterpene derivatiesPharmacol Res.29359366PubMedGoogle Scholar
  32. Szakiel, A, Kasprzyk, Z 1989Distribution of oleanolic acid glycosides in vacuoles and cell walls isolated from protoplasts and cells of Calendula officinalis leavesSteroids53501511CrossRefPubMedGoogle Scholar
  33. Szakiel, A, Wasiukiewicz, I, Janiszowska, W 1995Metabolism of [3−3H]oleanolic acid in the isolated Calendula officinalis leaf cells and transport of the synthesized glycosides to the cell wall and the extracellular spaceActa Biochim. Polon.422529PubMedGoogle Scholar
  34. Szakiel, A, Janiszowska, W 2002The mechanism of oleanolic acid monoglycosides transport into vacuoles isolated from Calendula officinalis leaf protoplastsPlant Physiol. Biochem.40203209CrossRefGoogle Scholar
  35. Szakiel, A, Grzelak, A, Dudek, P, Janiszowska, W 2003aBiosynthesis of oleanolic acid and its glycosides in Calendula officinalis suspension culturePlant Physiol. Biochem.41271275CrossRefGoogle Scholar
  36. Szakiel, A, Ruszkowski, D, Janiszowska, W 2003bExcretion of oleanolic acid glycosides to the medium from the roots of marigold Calendula officinalis L. Pol. JNat. Sci. 11216Google Scholar
  37. Subba Rao, G, Sinsheimer, JF, Cochran, KW 1974Antiviral activity of triterpenoid saponins containing acylated β-amyrin aglyconesJ. Pharmacol. Sci.63471473Google Scholar
  38. Tanaka, S, Uno, C, Akimoto, M, Tabata, M, Honda, C, Kamisako, W 1991Anti-allergic effect of bryonolic acid from Luffa cylindrical cell suspension culturePlanta Med.57527530PubMedGoogle Scholar
  39. Wichtl, M 1994Herbal Drugs and PhytopharmaceuticalsMedpharm Scientific PublisherStuttgart446Google Scholar
  40. Wojciechowski, Z 1975Biosynthesis of oleanolic acid glycosides by subcellular fractions of Calendula officinalis seedlingsPhytochemistry1417491753CrossRefGoogle Scholar
  41. Wojciechowski, Z, Jelonkiewicz-Konador, A, Tomaszewski, M, Jankowski, J, Kasprzyk, Z 1971The structure of glycosides of oleanolic acid isolated from the roots of Calendula officinalis Phytochemistry1011211124CrossRefGoogle Scholar

Copyright information

© Springer 2005

Authors and Affiliations

  • Anna Szakiel
    • 1
  • Dariusz Ruszkowski
    • 1
  • Wirginia Janiszowska
    • 1
  1. 1.Department of Plant BiochemistryWarsaw UniversityWarszawaPoland

Personalised recommendations