Abstract
To search for cytotoxic components fromAllium victorialis, MTT assays on each extract and an isolated component, gitogenin 3-O-lycotetroside, were performed against cancer cell lines. Cytotoxicities of most extract were shown to be comparatively weak, though IC50 values of CHCl3 fraction was found to be <31.3–368.4 μg/ml. From the incubated methanol extract at 36°C, eleven kinds of organosulfuric flavours were predictable by GC-MS performance. The most abundant peak was revealed to be 2-vinyl-4H-1,3-dithiin (1) by its mass spectrum. Further, this extract showed significant cytotoxicities toward cancer cell lies. Silica gel column chromatography of the n-butanol fraction led to the isolation of gitogenin 3-O-lycotetroside (3) along with astragalin (4) and kaempferol 3, 4′-di-O-β-D-glucoside (5). This steroidal saponin exhibited significant cytotoxic activities (IC50, 6.51–36.5 μg/ml) over several cancer cell lines. When compound3 was incubated for 24 h with human intestinal bacteria, a major metabolite was produced and then isolated by silica gel column chromatography. By examining parent- and prominent ion peak in FAB-MS spectrum of the metabolite, the structure was speculated not to be any of prosapogenins of3, suggesting that spiroketal ring were labile to the bacterial reaction. These suggest that disulfides produced secondarily are the antitumor principles.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Agrawal, P. K., Carbon-13 NMR of flavonoids, Elsevier, Amsterdam, p. 334–334, 1989.
Chalier, B., Perarnau, J. M. and Viel, J. F., Garlic, onion and cereal fibre as protective factors for breast cancer: a French case-control study.Eur. J. Epidemiol., 14, 737–747 (1998).
Denizot, F. and Lang, R. J., Rapid colorimetric assay for cell growth and survival: modification to the tetrazolium dye procedure giving improved sensitivity and reliability.J. Immunol. Methods, 89, 271–277 (1996).
Harris, W. S., Dujovne, C. A., Winsor, S. L., Gerround, L. L., Newton, F. A. and Gelfand R. A., Inhibiting cholesterol absorption with CP-88,818 (β-tigogenin cellobioside; tiqueside): Studies in normal and hyperlipidemic subjects.J. Cardiovasic Pharmacol., 30, 55–60 (1997).
Hikino, H., Tohkin, M., Kiso, Y., Namiki, T., Nishimura, S. and Takeyama, K., Antihepatotoxic actions ofAllium sativum Bulbs.Planta Med., 52, 163–168 (1986).
Kim, D. H., Yu, K. W., Bae, E. A., Park, H. J. and Choi, J. W., Metabolism of kalopanaxsaponin B and H by human intestinal bacteria and antidiabetic activity of their metabolites.Biol. Pharm. Bull., 21, 360–365 (1998).
Kim, J. I., Lee, S. H., Park, J. H., Park, H. J. and Lee, K. T., Induction of differentiation on the human histocytic lymphoma cell line U-937 by costunolide.Kor. J. Pharmacogn., 30, 7–11 (1999).
Lawson, L. D., Wang, Z. J. and Hughes, B. G., γ-Glutamyl-S-alkylcysteines in garlic and other Allium spp.: Precursors of age-dependent trans-1-propenyl thiosulfinates.J. Nat. Prod., 54, 436–444 (1991).
Lee, C. B., Plant illustration in Korea, Hyangmunsa, Seoul, 1985.
Liakopoulou-Kyriakides, M., Sinakos, Z. and Kyriakidids D. A., Identification of alliin, a constituent ofAllium cepa with an inhibitory effect on platelet aggregation.Phytochemistry, 24, 600–601 (1985).
Mahato, S. B. and Majumdar, I., Review articles number 84. Current trends in microbial steroid biotransformation. Phytochemistry, 34, 883–898 (1993).
Matsuura, H., Ushiroguch, T., Itakura, Y. and Fuwa, T., Further studies on steroidal glycosides from bulbs, roots and leaves ofAllium sativum.Chem. Pharm. Bull., 37, 2741–2743 (1989).
Mimaki, Y., Kumoto, T., Kuroda, M., Sashida, Y., Satomi, Y., Nishino, A. and Nishino, H., Steroidal saponins from Hosta Longipes and phospholipid metabolism of HeLa cells.Phytochemistry, 42, 1065–1070 (1996).
Moon, K. S., Usage and Components of Herbal Medicine, Scientific Encyclopedia Co., Pyongyang, 671–672, 1984.
Munday, J. S., James, K. A., Fray, L. M., Kirkwood, S. W. and Thomson, K. G., Daily supplementation with aged garlic extract, but not raw garlic, protects low density lipoprotein against in vitro oxidation.Atherosclerosis, 143, 399–404 (1999).
Mutsch-Eckner, M., Erdelmeier, C. A. J. and Sticher, O. A novel amino acid glycoside and three amino acids fromAllium sativum.J. Nat. Prod., 56, 864–869 (1993).
Nakano, K., Matsuda, E., Tsurumi, K., Yamasaki, T., Murakami, K., Takaishi, Y. and Tomimatsu, T., The steroidal glycosides of the flowers ofYucca gloriosa.Phytochemistry, 27, 3235–3239 (1989).
Nishimura, H., Wijaya, C. H. and Mizutani, J., Volatile flavor components and antithrombotic agents: Vinyldithiins fromAllium victorialis.J. Agric. Food. Chem., 36, 563–566 (1988).
Park, H. J., Young, H. S., Park, K. Y., Rhee, S. H., Chung, H. Y. and Choi, J. S., Flavonoids from the whole plants ofOrostachys japonicus.Arch. Pharm. Res., 14, 167–171 (1991).
Peng, J., Yao, X., Okada, Y. and Okuyama, T., Further studies on new furostanol saponins from the bulbs ofAllium macrostemon.Chem Pharm. Bull., 42(10): 2180–2182 (1994).
Petit, G. R., Doubek, D. L. and Herald, D. L., Isolation and structure of cytostatic steroidal saponins from the african medicinal plantBalanites aegyptica.J. Nat. Prod., 54, 1491–1502 (1991).
Siegers, C. P., Steffen, B., Robke, A. and Pentz, R., The effects of garlic preparations against human tumor cell proliferation.Phytomedicine, 6, 7–11 (1999).
Singh, A. and Shukla, Y., Antitumor activity of diallyl sulfide in two-stage mouse skin model of carcinogenesis.Biomed Environ. Sci., 11, 258–263, (1998).
Son, K. H., Do, J. C. and Kang, S. S., Steroidal saponins from the rhizomes ofPolygonatum sibiricum.J. Nat. Prod., 53, 333–339 (1990).
Wijaya, C. H., Muchtani, D., Lalel, H. J., H. J., Zakaria, F. and Kowara, S., Antiplatelet aggregation potencies of some Allium spp. grown in Indonesia.Nat. Prod. Sci., 2, 37–42 (1996).
Wu, J. L., Chou, C. C., Chen, M. H. and Wu, C. M., Volatile flavor compounds from shallots.J. Food Sci., 47, 606–608 (1982).
Yoshida, T., Saito, T. and Kadoya, S., New acylated flavonol glucosides inAllium tuberosum, Chem. Pharm. Bull., 35, 97–107 (1987).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Lee, KT., Choi, JH., Kim, DH. et al. Constitutents and the antitumor principle ofAllium victorialis var.platyphyllum . Arch Pharm Res 24, 44–50 (2001). https://doi.org/10.1007/BF02976492
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02976492