Cyclic Triterpenoid Saponins from Campanula lactiflora

Two cyclic natural compounds, 3b-O-[a-L-rhamnopyranosyl- (1 \to 2)-b-D-glucopyranosyl]-13a,14a-epoxy-8a,12b, 15-trihydroxy-(17E,21E)-17,21-campanuldien-6'(30)-olide, called lactifloroside A, 1, and 3b-O-[b-D-glucopyranosyl-(1 \to 2)-b-D-glucopyranosyl]- 13a,14a-epoxy-8a,12b-dihydroxy-(17E,21E)-17,21-campanuldien- 6'(30)-olide, called lactifloroside B, 2, were isolated for the first time from Campanula lactiflora and their structures deduced by high field 1D and 2D 400 MHz NMR, FT-IR, HPLC, GC-MS, (+/-) LC-MS/MS and (+) FAB-MS spectra. The aglycones of the 2 saponins were named 13a,14a-epoxy-3b,8a,12b,15-tetrahydroxy-(17E,21E)- 17,21-campanuldien-30-oic acid and 13a,14a-epoxy-3b,8a, 12b-trihydroxy-(17E,21E)-17,21-campanuldien-30-oic acid, and designated as campanuloic acid and 15-deoxycampanuloic acid, respectively.

Cyclic Triterpenoid Saponins from Campanula lactiflora

Two cyclic natural compounds, 3b-O-[a-L-rhamnopyranosyl- (1 \to 2)-b-D-glucopyranosyl]-13a,14a-epoxy-8a,12b, 15-trihydroxy-(17E,21E)-17,21-campanuldien-6'(30)-olide, called lactifloroside A, 1, and 3b-O-[b-D-glucopyranosyl-(1 \to 2)-b-D-glucopyranosyl]- 13a,14a-epoxy-8a,12b-dihydroxy-(17E,21E)-17,21-campanuldien- 6'(30)-olide, called lactifloroside B, 2, were isolated for the first time from Campanula lactiflora and their structures deduced by high field 1D and 2D 400 MHz NMR, FT-IR, HPLC, GC-MS, (+/-) LC-MS/MS and (+) FAB-MS spectra. The aglycones of the 2 saponins were named 13a,14a-epoxy-3b,8a,12b,15-tetrahydroxy-(17E,21E)- 17,21-campanuldien-30-oic acid and 13a,14a-epoxy-3b,8a, 12b-trihydroxy-(17E,21E)-17,21-campanuldien-30-oic acid, and designated as campanuloic acid and 15-deoxycampanuloic acid, respectively.

___

  • J. Damboldt, Campanula L. In: P.H. Davis, “Flora of Turkey and the East Aegean Islands”, Vol 6, University Press, Edinburgh. p. 2-65, 1977.
  • S.F. Dzhumyrko, E.T. Oganesyan and A.L. Shinkarenko, Khim. Prir. Soedin 5, 440-441 (1969).
  • S.F. Dzhumyrko, Khim. Prir. Soedin 2, 273-274 (1973).
  • N. Yaylı, N. Yıldırım, A. Usta, S. ¨Ozkurt and V. Akg¨un, Turk. J. Chem. 27, 749-755 (2003).
  • N. Yaylı, N. Yıldırım, N. Do˘gan, A. Usta and L. Altun, J. Asian Nat. Prod. Res. 7, 771-775 (2005).
  • F.H. Kong, D.Y. Zhu, R.S. Xu, Z.C. Fu and L.Y. Zhou, Tetrahedron Letters 27, 5765-5768 (1986).
  • R. Kasai, M. Miyakoshi, R.L. Nie, J. Zhou, K. Matsumoto, T. Morita, M. Nishi, K. Miyahara and O. Tanaka, Phytochemistry 27, 1439-1446 (1988).
  • A.F. Barrero and J. Altarejos, Mag. Reson. Chem. 31, 299-308 (1993).
  • S.B. Mahato and S. Sen, Phytochemistry 44, 1185-1236 (1997).
  • S.B. Mahato, S.K. Sarkar and G. Poddar, Phytochemistry 27, 3037-3067 (1988).
  • S.B. Mahato, A.K. Nandy and G. Roy, Phytochemistry 31, 2199-2249 (1992).
  • S.B. Mahato and A.P. Kundu, Phytochemistry 37, 1517-1575 (1994).
  • T. Baykal, T. Panayır, D. Ta¸sdemir, O. Sticher and ˙I. C¸ alı¸s, Phytochemistry 48, 867-873 (1998).
  • M. Konishi, Y. Hano, M. Takayama, T. Nomura, A.S. Hamzah, R.B. Ahmad and H. Jasmani, Phytochemistry , 525-528 (1998).
  • S.S. Yu, Z.Y. Xiao, P. Cai, T.Y. Jiang and J.K. Snyder, Tetrahedron 50, 11601-11612 (1994).
  • N.P. Sahu, Phytochemistry 41, 883-886 (1996).
  • Z. Jia, K. Koike, M. Kudo, H. Li and T. Nikaido, Phytochemistry 48, 529-536 (1998).
  • P.K. Agrawal, Phytochemistry 31, 3307-3330 (1992).
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

Composition and Antimicrobial Activities of Volatile Components of Minuartia meyeri

Nurettin YAYLI, Canan GÜLEÇ, Osman ÜÇÜNCÜ, Ahmet YAŞAR, Serdar ÜLKER, Kamil COŞKUNÇELEBİ, Salih TERZİOĞLU

Kinetics and Mechanism of Oxidation of 1,3--Butylene Glycol by Dihydroxyditellutoargentate(III) in Alkaline Medium

Jin-huan SHAN, Shu-ying HUO, Shi-gang SHEN, Han-wen SUN

First- and Second-Derivative Spectrophotometry for Simultaneous Determination of Copper and Cobalt by 1-(2-Pyridylazo)-2-naphthol in Tween 80 Micellar Solutions

Habibollah ESKANDARI, Ali Ghanbari SAGHSELOO

Structure of 1-(Thiophen-2-ylmethyl)-2-(thiophen-2-yl)-1H-benzimidazole

Necmi DEGE, Memet ŞEKERCİ, Süleyman SERVİ

Heterocyclic Synthesis Using Nitrilimines: Part 5. Synthesis of Some Novel Spiro Heterocycles

Hany M. DALLOUL, Peter H. BOYLE

Synthesis of a Ruthenium Complex Bound to a Polyimide Matrix: Investigating the Catalytic Properties in a Hydrosilylation Reaction

Turgay SEÇKİN, Süleyman KÖYTEPE, İsmail ÖZDEMİR, Bekir ÇETİNKAYA

Synthesis and Characterization of Metal Complexes of Cu(II), Ni(II), Zn(II), Co(II), Mn(II) and Cd(II) with Tetradentate Schiff Bases

Jian-ning LIU, Bo-wan WU, Bing ZHANG, Yongchun LIU

Synthesis and characterization of metal complexes of Cu(II), Ni(II), Co(II), Mn(II) and Cd(II) with tetradentate Schiff bases

Yongchun LIU, Jian-ning LIU, Bing ZHANG, Bo-wan WU

Analysis of Nanoparticle Transmission Electron Microscopy Data Using a Public- Domain Image-Processing Program, Image

Gerd H. WOEHRLE, James E. HUTCHISON, Saim ÖZKAR, Richard G. FINKE

Studies on 2-Ethyl-3-carbmethoxy-4-aryl-5-oxo-1,4,5,6,7,8-hexahydroquinoline Derivatives and Calcium Modulatory Activities

Cihat ŞAFAK, Elvan DOĞAN, Kevser EROL