O-Galloyl Flavonoids from Geranium pyrenaicum and Their in vitro Antileishmanial Activity

From the aerial parts of Geranium pyrenaicum Burm., a new flavonol glycoside, kaempferol 3-O-(2'',3''-di-O-galloyl)-{\ss}-D-glucopyranoside (7), along with 6 known related glycosides [kaempferol 3-O-b-D-glucopyranoside (1), quercetin 3-O-b-D-glucopyranoside (2), quercetin 3-O-b-D-galactopyranoside (3), kaempferol 3-O-(2''-O-galloyl)-b-D-glucopyranoside (4), quercetin 3-O-(2''-O-galloyl)-b-D-glucopyranoside (5) and quercetin 3-O-(2'',3''-di-O-galloyl)-{\ss}-D-glucopyranoside (6)] and the ellagitannins corilagin (8) and tellimagrandin I (9) were isolated. Their structures were established from spectroscopic studies (UV, FAB-MS, 1H and 13C-NMR, 1H-1H COSY, HETCOR, HMBC). Compounds 1-7 were evaluated for antileishmanial activity against a panel of Leishmania species (L. major, L. donovani and L. amazonensis), indicating appreciable in vitro activities (IC50 4-27 nM) when compared with Pentostam (IC50 10-11 nM).

O-Galloyl Flavonoids from Geranium pyrenaicum and Their in vitro Antileishmanial Activity

From the aerial parts of Geranium pyrenaicum Burm., a new flavonol glycoside, kaempferol 3-O-(2'',3''-di-O-galloyl)-{\ss}-D-glucopyranoside (7), along with 6 known related glycosides [kaempferol 3-O-b-D-glucopyranoside (1), quercetin 3-O-b-D-glucopyranoside (2), quercetin 3-O-b-D-galactopyranoside (3), kaempferol 3-O-(2''-O-galloyl)-b-D-glucopyranoside (4), quercetin 3-O-(2''-O-galloyl)-b-D-glucopyranoside (5) and quercetin 3-O-(2'',3''-di-O-galloyl)-{\ss}-D-glucopyranoside (6)] and the ellagitannins corilagin (8) and tellimagrandin I (9) were isolated. Their structures were established from spectroscopic studies (UV, FAB-MS, 1H and 13C-NMR, 1H-1H COSY, HETCOR, HMBC). Compounds 1-7 were evaluated for antileishmanial activity against a panel of Leishmania species (L. major, L. donovani and L. amazonensis), indicating appreciable in vitro activities (IC50 4-27 nM) when compared with Pentostam (IC50 10-11 nM).

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  • R. Hegnauer, “Chemotaxonomie der Pflanzen” Vol. VIII, Birkhauser Verlag, Basel, Berlin, 511-516. 1989.
  • T. Baytop, “Therapy with medicinal plants in Turkey (Past and Present)” 2ndNobel Tıp Kitabevleri Ltd., ˙Istanbul, 1999.
  • P.H. Davis, “Geranium” in Flora of Turkey and the East Aegean Islands vol. 2, ed. P.H. Davis, pp. 441-474, University Press, Edinburgh, 1966.
  • H. Ay¸ci¸cek and M. Tany¨uksel, T¨urk Hij. Den. Biyol. Derg. 54, 35-39 (1997).
  • U.Z. Ok, ˙I.C. Balcıo˘glu, A. Taylan ¨Ozkan, S. ¨Ozensoy and Y. ¨Ozbel, Acta Trop. 84, 43-48 (2002). ¨
  • H. Kolodziej, O. Kayser, A.F. Kiderlen, H. Ito, T. Hatano, T. Yoshida and L.Y. Foo, Biol. Pharm. Bull. 24, 1021 (2001).
  • O.A. Radtke, L.Y. Foo, Y. Lu, A.F. Kiderlen and H. Kolodziej, Z. Naturforsch. 58c, 395-400 (2003).
  • K.P. Latte and H. Kolodziej, Phytochemistry 54, 701-708 (2000).
  • C.K. Wilkins and B.A. Bohm, Phytochemistry 15, 211-214 (1976).
  • S. Funayama and H. Hikino, Chem. Pharm. Bull. 27, 2865-2868 (1979).
  • K.R. Markham, B. Ternai, R. Stanley, H. Geiger and T.J. Mabry, Tetrahedron 34, 1389-1397 (1978).
  • T. Isobe, N. Ito and Y. Noda, Phytochemistry 19, 1877 (1980).
  • T. Isobe, T. Fukushige and Y. Noda, Chem. Lett. 27-30 (1979).
  • Y. Amakura, K. Kawada, T. Hatano, I. Agata, T. Sugaya, S. Nishibe, T. Okuda and T. Yoshida, Can. J. Chem. 75, 727-733 (1997).
  • H.Y. Kim, B.H. Moon, H.J. Lee and D.H. Choi, J. Ethnopharmacol. 93, 227-230 (2004).
  • B. Beutler and A. Cerami, Annu. Rev. Immunol. 7, 625-655 (1989).
  • A. Billiau, Adv. Immunol. 62, 61-130 (1996).
  • J. Theza, “The Cytokine Network and Immune Functions”, Oxford University Press, Inc., New York, 1999.
  • M. Helle, L. Boeije and L.A. Aarden, Eur. J. Immunol. 18, 1535-1540 (1988).
  • M. Liu, P. Wilairat, S.L. Croft, A.L. Tan and M. Go, Bioorg. Med. Chem. 11, 2729-2738 (2003).
  • O. Kayser, A.F. Kiderlen, U. Folkens and H. Kolodziej, Planta Med. 65, 316-319 (1999).
  • H. Kolodziej and A.F. Kiderlen, Phytochemistry (in press) (2005).
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK
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