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.
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- 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).