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

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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.

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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

References

  • Anon (2001) ArticleTitleFinal report on the safety assessment of Calendula officinalis extract and Calendula officinalis Int. J. Toxicol. 20 13–20

    Google Scholar 

  • J Barnes L Anderson J Philipson (2002) Herbal Medicines Pharmaceutical Press London 103–106

    Google Scholar 

  • NG Bisset M Wichtl (2001) Herbal Drugs and Phytopharmaceuticals CRC Press Boca Raton 167

    Google Scholar 

  • FZ Dajani RG Bianchi JJ Casler JF Weet (1979) ArticleTitleGastric antiulcer and antisecretory effects of carbenoxolone, aldosterone and desoxycorticosterone in rats Arch. Int. Pharmacodyn. 242 128–138 Occurrence Handle543742 Occurrence Handle1:CAS:528:DyaL3cXhvFWktL0%3D

    PubMed  CAS  Google Scholar 

  • DJ Dargan JH Subak-Sharpe (1985) ArticleTitleThe effect of triterpenoid compounds on uninfected and Herpes Simplex virus-infected cells in culture. I. Effect of cells growth, virus particles and virus replication J. Gen. Virol. 66 1771–1784 Occurrence Handle2991440 Occurrence Handle1:CAS:528:DyaL2MXkvFygtb8%3D Occurrence Handle10.1099/0022-1317-66-8-1771

    Article  PubMed  CAS  Google Scholar 

  • W Eisenreich A Bacher D Arigoni F Rohdich (2004) ArticleTitleBiosynthesis of isoprenoids via the non-mevalonate pathway Cell. Mol. Life Sci. 61 1401–1426 Occurrence Handle10.1007/s00018-004-3381-z Occurrence Handle15197467 Occurrence Handle1:CAS:528:DC%2BD2cXmtFSku74%3D

    Article  PubMed  CAS  Google Scholar 

  • C Farina M Pinza G Pifferi (1998) ArticleTitleSynthesis and anti-ulcer activity of new derivatives of glycyrrhetic, oleanolic and ursolic acid Il Farmaco 53 22–32 Occurrence Handle10.1016/S0014-827X(97)00013-X Occurrence Handle9543723 Occurrence Handle1:CAS:528:DyaK1cXit1eqsbg%3D

    Article  PubMed  CAS  Google Scholar 

  • RSH Finney AI Tarknoy (1960) ArticleTitleThe pharmacological properties of glycyrrhetinic acid hydrogen succinate J. Pharm. Pharmacol. 12 49–53 Occurrence Handle13822948 Occurrence Handle1:CAS:528:DyaF3cXmvFyrtg%3D%3D

    PubMed  CAS  Google Scholar 

  • A Grzelak W Janiszowska (2002) ArticleTitleInitiation and growth characteristics of suspension cultures of Calendula officinalis cells Plant Cell Tiss. Org. 71 29–40 Occurrence Handle1:CAS:528:DC%2BD38Xls1CntLY%3D

    CAS  Google Scholar 

  • H Inoue S Kurosu T Takeuchi T Mori S Shibata (1990) ArticleTitleGlycyrrhetinic acid derivatives anti-nociceptive activity of deoxoglycyrrhetol dihemiphthalate and the related compounds J. Pharm. Pharmacol. 42 199–200 Occurrence Handle1974618 Occurrence Handle1:CAS:528:DyaK3cXkslWisL4%3D

    PubMed  CAS  Google Scholar 

  • W Janiszowska Z Kasprzyk (1974) ArticleTitleTransport of glycosides of oleanolic acid from shoot to root in Calendula officinalis Acta Biochim. Polon. 16 415–421

    Google Scholar 

  • W Janiszowska Z Kasprzyk (1977) ArticleTitleIntracellular distribution and origin of pentacyclic triterpenes in Calendula officinalis leaves Phytochemistry 16 1919–1923 Occurrence Handle1:CAS:528:DyaE1cXkslCksQ%3D%3D

    CAS  Google Scholar 

  • 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.

  • W Janiszowska A Szakiel (1991) ArticleTitleThe transport of [3−3H]oleanolic acid and its monoglycosides to isolated vacuoles of protoplasts from Calendula officinalis leaves Phytochemistry 9 2993–2997

    Google Scholar 

  • Z Kasprzyk Z Wojciechowski (1967) ArticleTitleThe structure of triterpenic glycosides from the flowers of Calendula officinalis L. Phytochemistry 6 69–75 Occurrence Handle10.1016/0031-9422(67)85009-X Occurrence Handle1:CAS:528:DyaF2sXlt12gsQ%3D%3D

    Article  CAS  Google Scholar 

  • Z Kasprzyk Z Wojciechowski W Janiszowska (1970) ArticleTitleIncorporation of 1−14C-acetate into glycosides of Calendula officinalis Phytochemistry 9 561–564 Occurrence Handle10.1016/S0031-9422(00)85690-3 Occurrence Handle1:CAS:528:DyaE3cXktlagurw%3D

    Article  CAS  Google Scholar 

  • Z Kasprzyk W Janiszowska E Sobczyk (1973) ArticleTitleMetabolism of the new series of oleanolic acid glycosides in Calendula officinalis Acta Biochim. Polon. 20 231–235 Occurrence Handle4749664 Occurrence Handle1:CAS:528:DyaE2cXhsVKh

    PubMed  CAS  Google Scholar 

  • S Kohlmunzer (1998) Pharmacognosis. Handbook for pharmacy students PZWL Warsaw 319–321

    Google Scholar 

  • J Liu (1995) ArticleTitlePharmacology of oleanolic acid and ursolic acid. J. Ethnopharmacol. 49 57–68 Occurrence Handle10.1016/0378-8741(95)90032-2 Occurrence Handle8847885 Occurrence Handle1:CAS:528:DyaK28Xht12gtL4%3D

    Article  PubMed  CAS  Google Scholar 

  • SB Mahato AK Nandy G Roy (1992) ArticleTitleTriterpenoids Phytochemistry 35 2199–2249

    Google Scholar 

  • DH Miles U Kokpol LH Zalkow SJ Steindel JB Nabors (1974) ArticleTitleTumor inhibitors. I. Preliminary investigation of antitumors activitity of Saracenia flava J. Pharmacol. Sci. 63 613–615 Occurrence Handle1:CAS:528:DyaE2cXksVGnsLw%3D

    CAS  Google Scholar 

  • H Nishino A Nishino J Takayasu T Hasegawa A Iwashima K Hitahahayashi S Iwata S Shibata (1988) ArticleTitleInhibition of the tumor-promoting action of 12-O-tetradecanoylphorbol-13-acetate by some oleanane-type triterpenoid compounds Cancer Res. 48 5210–5215 Occurrence Handle3409245 Occurrence Handle1:CAS:528:DyaL1MXhvVWktA%3D%3D

    PubMed  CAS  Google Scholar 

  • K Oda H Matsuda T Murakami S Katayama T Ohgitani M Yoshikawa (2000) ArticleTitleAdjuvant and haemolytic activities of 43 saponins derived from medicinal and food plants Biol. Chem. 381 67–74 Occurrence Handle10.1515/BC.2000.009 Occurrence Handle10722052 Occurrence Handle1:CAS:528:DC%2BD3cXit1ymt78%3D

    Article  PubMed  CAS  Google Scholar 

  • E Paulsen (2002) ArticleTitleContact sensitization from Compositae-containing herbal remedies and cosmetics Contact Derm. 47 189–198 Occurrence Handle12492516

    PubMed  Google Scholar 

  • D Pauthe-Dayde M Rochd M Henry (1990) ArticleTitleTriterpenoid saponin production in callus and multiple shoot cultures of Gypsophilla sp Phytochemistry 29 483–487 Occurrence Handle1:CAS:528:DyaK3cXhsFGhurc%3D

    CAS  Google Scholar 

  • G Pinducciu C Serra MG Cagetti M Cotti D Deida M Pinza (1995) ArticleTitleSelective antimicrobial activity of triterpene derivates on oral bacteria Med. Microbiol. Lett. 4 83–90 Occurrence Handle1:CAS:528:DyaK2MXlvVehsL4%3D

    CAS  Google Scholar 

  • D Ruszkowski A Szakiel W Janiszowska (2003) ArticleTitleMetabolism of [3−3H]oleanolic acid in Calendula officinalis L. roots Acta Physiol. Plant. 25 311–317 Occurrence Handle1:CAS:528:DC%2BD2cXmsVagtg%3D%3D

    CAS  Google Scholar 

  • 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.

  • 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.

  • Y Sashida K Ogawa T Yamanouchi H Tanaka I Shoyama I Nishioka (1994) ArticleTitleTriterpenoids from callus tissue of Actinidia polygama Phytochemistry 33 377–380

    Google Scholar 

  • C Serra G Lampis R Pompei M Pinza (1994) ArticleTitleAntiviral activity of new triterpene derivaties Pharmacol Res. 29 359–366 Occurrence Handle7971687 Occurrence Handle1:CAS:528:DyaK2MXot1SnsA%3D%3D

    PubMed  CAS  Google Scholar 

  • A Szakiel Z Kasprzyk (1989) ArticleTitleDistribution of oleanolic acid glycosides in vacuoles and cell walls isolated from protoplasts and cells of Calendula officinalis leaves Steroids 53 501–511 Occurrence Handle10.1016/0039-128X(89)90028-7 Occurrence Handle2799856 Occurrence Handle1:CAS:528:DyaK3cXlt1WqsA%3D%3D

    Article  PubMed  CAS  Google Scholar 

  • A Szakiel I Wasiukiewicz W Janiszowska (1995) ArticleTitleMetabolism 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 space Acta Biochim. Polon. 42 25–29 Occurrence Handle7653156 Occurrence Handle1:CAS:528:DyaK2MXmtFKgsL4%3D

    PubMed  CAS  Google Scholar 

  • A Szakiel W Janiszowska (2002) ArticleTitleThe mechanism of oleanolic acid monoglycosides transport into vacuoles isolated from Calendula officinalis leaf protoplasts Plant Physiol. Biochem. 40 203–209 Occurrence Handle10.1016/S0981-9428(02)01370-0 Occurrence Handle1:CAS:528:DC%2BD38XitFWrs7k%3D

    Article  CAS  Google Scholar 

  • A Szakiel A Grzelak P Dudek W Janiszowska (2003a) ArticleTitleBiosynthesis of oleanolic acid and its glycosides in Calendula officinalis suspension culture Plant Physiol. Biochem. 41 271–275 Occurrence Handle10.1016/S0981-9428(03)00018-4 Occurrence Handle1:CAS:528:DC%2BD3sXjtVKhur4%3D

    Article  CAS  Google Scholar 

  • A Szakiel D Ruszkowski W Janiszowska (2003b) ArticleTitleExcretion of oleanolic acid glycosides to the medium from the roots of marigold Calendula officinalis L. Pol. J Nat. Sci. 1 1 216

    Google Scholar 

  • G Subba Rao JF Sinsheimer KW Cochran (1974) ArticleTitleAntiviral activity of triterpenoid saponins containing acylated β-amyrin aglycones J. Pharmacol. Sci. 63 471–473

    Google Scholar 

  • S Tanaka C Uno M Akimoto M Tabata C Honda W Kamisako (1991) ArticleTitleAnti-allergic effect of bryonolic acid from Luffa cylindrical cell suspension culture Planta Med. 57 527–530 Occurrence Handle1818343 Occurrence Handle1:CAS:528:DyaK38Xht1Smur0%3D

    PubMed  CAS  Google Scholar 

  • M Wichtl (1994) Herbal Drugs and Phytopharmaceuticals Medpharm Scientific Publisher Stuttgart 446

    Google Scholar 

  • Z Wojciechowski (1975) ArticleTitleBiosynthesis of oleanolic acid glycosides by subcellular fractions of Calendula officinalis seedlings Phytochemistry 14 1749–1753 Occurrence Handle10.1016/0031-9422(75)85287-3 Occurrence Handle1:CAS:528:DyaE2MXlslCjtbw%3D

    Article  CAS  Google Scholar 

  • Z Wojciechowski A Jelonkiewicz-Konador M Tomaszewski J Jankowski Z Kasprzyk (1971) ArticleTitleThe structure of glycosides of oleanolic acid isolated from the roots of Calendula officinalis Phytochemistry 10 1121–1124 Occurrence Handle10.1016/S0031-9422(00)89949-5 Occurrence Handle1:CAS:528:DyaE3MXktlWhur0%3D

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Plant Biochemistry, Warsaw University, ul. Miecznikowa 1, 02-096, Warszawa, Poland

    Anna Szakiel, Dariusz Ruszkowski & Wirginia Janiszowska

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  1. Anna Szakiel
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  2. Dariusz Ruszkowski
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  3. Wirginia Janiszowska
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Correspondence to Wirginia Janiszowska.

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Szakiel, A., Ruszkowski, D. & Janiszowska, W. Saponins in Calendula officinalis L. – Structure, Biosynthesis, Transport and Biological Activity. Phytochem Rev 4, 151–158 (2005). https://doi.org/10.1007/s11101-005-4053-9

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