[en] Further to a systematic chemotaxonomic study of Uzbek Haplophyllum A. Juss. plants selected on ethnopharmacological data, 14 alkaloids were screened for their cytotoxic properties. As a first selection for interesting compounds, each alkaloid was tested against two human cancer cell lines (HeLa and HCT-116), using WST-1 reagent. Of the 14 alkaloids, 5 were cytotoxic when tested against the HeLa line with an IC50 < 100 microM. These five compounds consisted of three furoquinolines: skimmianine; haplopine and gamma-fagarine and two pyranoquinolones: flindersine and haplamine. Only haplamine was active against the HCT-116 line. The cytotoxic properties of these five alkaloids were further investigated against five additional human cancer cell lines. Their structure-activity relationships will be discussed. Of these five pre-selected alkaloids, only haplamine showed significant cytotoxic activity against all the tested cell lines. This is the first report of the cytotoxic activity of haplamine. Finally, this pyranoquinolone alkaloid was tested here against 14 different cancer cell lines and against normal skin fibroblasts.
Research Center/Unit :
CIRM - Laboratoire de Pharmacognosie - Laboratoire de chimie médicale
V.I. Akhmedjanova, I.A. Bessonova, and S.Yu. Yunusov Alkaloids of Haplophyllum perforatum Khimiya Prirodnykh Soedinenii 3 1976 320 328
V.I. Akhmedjanova, I.A. Bessonova, and S.Yu. Yunusov Alkaloids of Haplophyllum foliosum Khimiya Prirodnykh Soedinenii 6 1980 803 805
V.I. Akhmedjanova, I.A. Bessonova, and S.Yu. Yunusov The structure of leptomerine Khimiya Prirodnykh Soedinenii 1 1986 84 86
Kh.S. Akhmedkhodzhaeva, and A.G. Kurmukov Pharmacology of haplamine Doklady Akademii Nauk UzSSR 8 1975 36
E.Kh. Batirov, A.D. Matkarimov, V.M. Malikov, and E. Seitmuratov Haplophyllum obtusifoliumcoumarins Khimiya Prirodnykh Soedinenii 6 1982 691 695
I.A. Bessonova Components of Haplophyllum bucharicum Chemistry of Natural Compounds (Translation of Khimiya Prirodnykh Soedinenii) 36 2000 323 324
Z.Sh. Faizutdinova, I.A. Bessonova, and S.Yu. Yunusov Structures of perforine and haplophyllidine Khimiya Prirodnykh Soedinenii 6 1968 360 367
J.G. Graham, M.L. Quinn, D.S. Fabricant, and N.R. Farnsworih Plants used against cancer - an extension of the work of Jonaihan Hartwell Journal of Ethnopharmacology 73 2000 347 377
W.D. MacRae, and G.H.N. Towers Biological activities of lignans Phytochemistry 23 1984 1207 1220
E.F. Nesmelova, D.M. Razakova, V.I. Akhmedzhanova, and A.I. Bessonova Diphyllin from Haplophyllum albertii-regelii H. bucharicum and H. perforatum Khimiya Prirodnykh Soedinenii 5 1983 643 644
N. Shobana, P. Yersoda, and P. Shanmugan A convenient approach to the synthesis of prenyl-, furo- and pyranoquinoline alkaloids of the Rutaceae Tetrahedron 45 1989 757 762
C.C. Townsend Hooker's Icones Plantarium, vol. XL (parts I-III): Taxonomic Revision of the Genus Haplophyllum 1986 Bentham-Moxon Trustees Whitstable pp. 336
M.P. Yuldashev Flavonoids and coumarins of Haplophyllum leptomerum and H. dubium Chemistry of natural compounds 38 2002 192 193
S.Yu. Yunusov, and G.P. Sidyakin Alkaloids of Haplophyllum species. II Zhurnal Obshchei Khimii 25 1955 2009 2016