Planta Med 2009; 75(2): 163-167
DOI: 10.1055/s-0028-1088391
Natural Product Chemistry
Original Paper
© Georg Thieme Verlag KG Stuttgart · New York

Biologically Active Triterpenoids from Cephalaria ambrosioides

Sofia Pasi1 , Nektarios Aligiannis1 , Harris Pratsinis1 , 2 , Alexios-Leandros Skaltsounis1 , Ioanna B. Chinou1
  • 1Department of Pharmacognosy and Natural Products Chemistry, School of Pharmacy, University of Athens, Athens, Greece
  • 2Present address: Laboratory of Cell Proliferation & Ageing, Institute of Biology, NCSR ”Demokritos”, Athens, Greece
Weitere Informationen

Publikationsverlauf

Received: May 18, 2007 Revised: September 29, 2008

Accepted: October 6, 2008

Publikationsdatum:
16. Januar 2009 (online)

Abstract

The roots of Cephalaria ambrosioides yielded a new triterpene, 6α-hydroxyhederagenic acid (1), in addition to the known triterpene hederagenic acid (2) and four corresponding saponins, leontoside A (or akeboside Stb) (3), kalopanax saponin A (or α-hederin) (4), saponin PG (or sapindoside B) (5), and dipsacoside B (6). Their structures have been elucidated on the basis of their spectral data (MS, 1 D and 2 D NMR) and by some chemical transformations. The extract and all isolated compounds were evaluated for their antimicrobial, molluscicidal and in vitro cytotoxic activities. All compounds showed strong antimicrobial activity (MIC values 1.80 – 2.50 μg/mL), with 5 and 6 exhibiting activities comparable to those of standard antibiotics. Moreover, compounds 35 were active against all assayed cancer cell lines, whereas compounds 3 and 4 exhibited higher activities against Biomphalaria glabrata snails, with minimum inhibitory concentrations of 5.4 and 6.2 μg/mL, respectively.

References

  • 1 Grauter W, Burdet H M. Dipsacaceae. In: Greuter W, Raus T, editors Med. Checklist Notulae 11. Berlin; Willdenowia 1985: 15 (71 – 2)
  • 2 Ferguson I K. Flora Europaea, Vol. 3. In: Tutin TG, Heywood VH, Burges NA, Moore DM, Valentine SM, Webb DA, editors London; Cambridge University Press 1972: 145
  • 3 Aliev A M, Movsumov I S. Biologically active substances from several representatives of the genus Cephalaria. .  Azerb Med Zh. 1981;  58 36-40
  • 4 Kirmizigul S, Anil H. Triterpenoid saponins from Cephalaria transsylvanica. .  J Nat Prod. 1996;  59 415-8
  • 5 Passi S, Aligiannis N, Skaltsounis A L, Chinou I B. A new lignan-glycoside and other constituents from Cephalaria ambrosioides. .  Nat Prod Lett. 2002;  16 365-70
  • 6 Graikou K, Aligiannis N, Chinou I B, Harvala C. Cantleyoside-dimethyl-acetal and other iridoid glucosides from Pterocephalus perennis– Antimicrobial activities.  Z Natuforsch C. 2002;  57 95-9
  • 7 Papalexandrou A, Magiatis P, Perdetzoglou D, Skaltsounis A L, Chinou I B, Harvala C. Iridoids from Scabiosa variifolia growing in Greece.  Biochem Syst Ecol. 2003;  31 91-3
  • 8 Magiatis P, Pratsinis H, Kalpoutzakis E, Konstantinidou A, Davaris P, Skaltsounis A L. Hydrolyzable tannins, the active constituents of three Greek Cytinus taxa against several tumor cell lines.  Biol Pharm Bull. 2001;  24 707-9
  • 9 Melliou E, Chinou I. Chemistry and bioactivity of Royal Jelly from Greece.  J Agric Food Chem. 2005;  53 8987-92
  • 10 Hostettmann K, Kizu H, Tomimori T. Molluscicidal properties of various saponins.  Planta Med. 1982;  44 34-5
  • 11 Treyvaud V, Martson A, Dyatmiko W, Hostettmann K. Molluscicidal saponins from Phytolacca icosandra. .  Phytochemistry. 2000;  55 603-9
  • 12 Agarwal S K, Rastogi R P. Hederagenic acid and other constituents of Viburnum erubescens. .  Phytochemistry. 1974;  13 666-8
  • 13 Shao C J, Kasai R, Ohtani K, Xu J D, Tanaka O. Saponins from leaves of Kalopanax septemlobus (Thunb) Koidz.: structures of Kalopanax-saponins La, Lb and Lc.  Chem Pharm Bull. 1989;  37 3251-4
  • 14 Kinjo J, Uemura H, Nakamura M, Nohara T. Two new triterpenoidal glycosides from Medicago polymorpha L.  Chem Pharm Bull. 1994;  42 1339-41
  • 15 Kong J, Li X G, Wei B Y, Yang C R. Triterpenoid glycosides from Decaisnea fargesii. .  Phytochemistry. 1993;  33 427-30
  • 16 Sawada H, Miyakoshi M, Isoda S, Ida Y, Shoji J. Saponins from leaves of Acanthopanax sieboldianus. .  Phytochemistry. 1993;  34 1117-21
  • 17 Li X G, Yang C R, Liu Y Q, Kasai R, Ohtani K, Yamashaki K. et al . Triterpenoid glycosides from Anemoclema glaucifolium. .  Phytochemistry. 1995;  39 1175-9
  • 18 Kamilov K M, Putieva Z M, Khalmatov K K, Abubakirov N K. Hederagonic acid of Dipsacus azureus. Chem Nat Compd (Engl.  Transl.) 1986; 22 : 741 – 2 Khim Prir Soedin. 1986;  22 797-8
  • 19 Putieva Z M, Mukhamedziev M M. Triterpene glycosides of Dipsacus azureus. Chem Nat Compd (Engl.  Transl.) 1998; 34 : 341 – 2 Khim Prir Soedin . 1998;  3 379-81
  • 20 Hegnauer R. Dipsacaceae, Vol. IV. Chemotaxonomie der Pflanzen VIII. Heidelberg; Birkhäuser Verlag 1989: 389-92
  • 21 Miyakoshi M, Shirasuna K, Hirai Y, Shingu K, Isoda S, Shoji J. et al . Triterpenoid saponins of Acanthopanax nipponicus leaves.  J Nat Prod. 1999;  62 445-8
  • 22 Wang Y, Zhang Y, Zhu Z, Zhu Z, Zhu S, Li Y. et al . Exploration of the correlation between the stucture, hemolytic activity and cytotoxicity of steroid saponins.  Bioorg Med Chem. 2007;  15 2528-32

Prof. Dr. Ioanna B. Chinou

Department of Pharmacognosy and Chemistry of Natural Products

School of Pharmacy

University of Athens

University Campus of Zografou

157 71 Athens

Greece

Telefon: +30-210-727-4595

Fax: +30-210-727-4115

eMail: ichinou@pharm.uoa.gr