Abstract
Bioassay-directed fractionation of a methanolic extract from the seeds of Draba nemorosa (Brassicaceae) led to isolation of a new flavonol glycoside, drabanemoroside (5, kaempferol 3-O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranose) along with four known flavonoid derivatives (1–4), four cardenolide glycosides (6–9). Kaempferol glycosides 2 and 5 showed strong cytotoxicity against human small lung cancer cell line A549 and melanoma SK-Mel-2 with an IC50 of 0.5 μg/mL and 1.9 μg/mL, respectively. Cardenolide glycosides 6–9 showed potent cytotoxicity (A549) in the range of 0.01–0.032 μg/mL. Their structures were characterized based on spectroscopic data (2D NMR, HRTOFMS, IR, and UV) and comparison of literature values. The carbohydrate units were also confirmed by comparing the hydrolysate of 5 with authentic monosaccharides.
Similar content being viewed by others
Explore related subjects
Discover the latest articles and news from researchers in related subjects, suggested using machine learning.References
Calis, I., Heilmann, J., Tasdemir, D., Linden, A., Ireland, C. M., and Sticher, O., Flavonoid, iridoid, and lignan glycosides from Putoria calabrica. J. Nat. Prod., 64, 961–964 (2001).
Filigenzi, M. S., Woods, L. W., Booth, M. C., Tor, E. R., and Puschner, B., Determination of strophanthidin in ingesta and plant material by LC-MS/MS. J. Agric. Food Chem., 52, 2174–2178 (2004).
Graham, J. G., Quinn, M. L., Fabricant, D. S., and Farnsworth, N. R., Plants used against cancer — an extension of the work of Jonathan Hartwell. J. Ethnopharmacol., 73, 347–377 (2000).
Ho, J.-C., Chen, C.-M., and Row, L.-C., Flavonoids and benzene derivatives from the flowers and fruit of Tetrapanax papyriferus. J. Nat. Prod., 68, 1773–1775 (2005).
Hou, Y., Cao, S., Brodie, P., Callmander, M., Ratovoson, F., Randrianaivo, R., Rakotobe, E., Rasamison, V. E., Rakotonandrasana, S., TenDyke, K., Suh, E. M., and Kingston, D. G. I., Antiproliferative cardenolide glycosides of Elaeodendron alluaudianum from the Madagascar rainforest. Bioorg. Med. Chem., 17, 2215–2218 (2009).
Karkare, S., Adou, E., Cao, S., Brodie, P., Miller, J. S., Andrianjafy, N. M., Razafitsalama, J., Andriantsiferana, R., Rasamison, V. E., and Kingston, D. G. I., Cytotoxic Cardenolide glycosides of Roupellina (Strophanthus) boivinii from the Madagascar rainforest. J. Nat. Prod., 70, 1766–1770 (2007).
Kim, T. J., Korean Resources Plants. Seoul National University Press, Seoul, Korea, vol. 2, pp. 59, (1996).
Kung, H. P. and Huang, W.-Y., Chemical investigation of Draba nemorosa, L. The isolation of sinapine iodide. J. Am. Chem. Soc., 71, 1836–1837 (1949).
Lee, Y. S., Lee, S., Lee, H. S., Kim, B.-K., Ohuchi, K., and Shin, K. H., Inhibitory effects of isorhamnetin-3-O-β-Dglucoside from Salicornia herbacea on rat lens aldose reductase and sorbitol accumulation in streptozotocininduced diabetic rat tissues. Biol. Pharm. Bull., 28, 916–918 (2005).
Li, T.-M., Li, W.-K., and Yu, J.-G., Flavonoids from Artabotrys hexapetalus. Phytochemistry, 45, 831–833 (1997).
Ly, T. N., Hazama, C., Shimoyamada, M., Ando, H., Kato, K., and Yamauchi, R., Antioxidative compounds from the outer scales of onion. J. Agric. Food Chem., 53, 8183–8189 (2005).
Makarevich, I. F., Alistrenko, A. I., Kobzin, D. A., Chernyaev, Y. A., and Slyusarskaya, T. V., Cardenolide glycosides of Cheiranthus allioni. XVI. Neoevonoside and cellobiosyldigigulomethyloside. Chem. Nat. Comp., 32, 53–55 (1996).
Melero, C. P., Medarde, M., and Feliciano, A. S., A short review on cardiotonic steroids and their aminoguanidine analogues. Molecules, 5, 51–81 (2000).
Moon, S.-S., Rahman, A. A., Kim, J.-Y., and Kee, S.-H., Hanultarin, a cytotoxic lignin as an inhibitor of actin cytoskeleton polymerization from the seeds of Trichosanthes kirilowii. Bioorg. Med. Chem., 16, 7264–7269 (2008).
Nakamura, T., Goda, Y., Sakai, S., Kondo, K., Akiyama, H., and Toyoda, M., Cardenolide glycosides from seeds of Corchorus olitorius. Phytochemistry, 49, 2097–2101 (1998).
Park, Y.-K. and Lee, C. Y., Identification of isorhamnetin 4′-Glucoside in onions. J. Agric. Food Chem., 44, 34–36 (1996).
Rosch, D., Krumbein, A., Mugge, C., and Kroh, L. W., Structural investigations of flavonol glycosides from sea buckthorn (Hippophae rhamnoides) pomace by NMR spectroscopy and HPLC-ESI-MSn. J. Agric. Food Chem., 52, 4039–4046 (2004).
Sanbongi, C., Osakabe, N., Natsume, M., Takizawa, T., Gomi, S., and Osawa, T. Antioxidative polyphenols isolated from Theobroma cacao. J. Agric. Food Chem., 46, 454–457 (1998).
Song, J., Manir, M. M., and Moon, S.-S., Cytotoxic grifolin derivatives from the wild mushroom Boletus pseudocalopus (Basidiomycetes). Chem. Biodivers., 6, 1435–1442 (2009).
Sultan, M. Z., Jeon, Y.-M., and Moon, S.-S., Labdane-type diterpenes active against acne from pine cones (Pinus densiflora). Planta Med., 74. 449–452 (2008).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Moon, SS., Rahman, A.A., Manir, M. et al. Kaempferol glycosides and cardenolide glycosides, cytotoxic constituents from the seeds of Draba nemorosa (Brassicaceae). Arch. Pharm. Res. 33, 1169–1173 (2010). https://doi.org/10.1007/s12272-010-0806-0
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12272-010-0806-0


