Two new glycosides of 30-normedicagenic acid, namely 3-O-[β-D-glucuronopyranosyl methyl ester]-2β,3β-dihydroxy-30-noroleane-12,20(29)-diene-23,28-dioic acid 28-O-β-D-glucopyranosyl ester, and 3-O-β-D-glucopyranosyl-2β,3β-dihydroxy-30-noroleane-12,20(29)-diene-23,28-dioic acid, together with the known 3-O-β-glucopyranosyl-2β,3β-dihydroxy-30-noroleane-12,20(29)-diene-23,28-dioic acid 28-O-β-glucopyranosyl ester, and 3-O-β-glucuronopyranosyl-2β,3β-dihydroxy-30-noroleane-12,20(29)-diene-23,28-dioic acid 28-O-β-glucopyranosyl ester were isolated from the aerial parts of Chenopodium foliosum Asch. The structures of the compounds were determined by means of spectroscopic methods (1D and 2D NMR, UV, IR) and HRMS-ESI. The compounds were tested for cytotoxicity on three leukemic cell lines (BV-173, SKW-3, HL-60). In addition, the saponins showed moderate stimulatory effects on interleukin-2 production in PHA/PMA stimulated Jurkat E6.1 cells.
APGII. (2003) An update of the Angiosperm Phylogeny Group classification for the orders and families of flowering plants: APG II. Botanical Journal of the Linnean Society, 141, 399–436.
2.
KühnU. (1993) Chenopodiaceae. In The families and genera of vascular plants. Vol. 2, KubitzkiK. (Ed.). Springer, Hamburg. 253–281.
3.
PrakashD, PalM. (1998) Chenopodium: seed protein, fractionation and amino acid composition. International Journal of Food Sciences and Nutrition, 49, 271–275
4.
BhargavaA, ShuklaS, OhriD. (2003) Genetic variability and heritability of selected traits during different cuttings of vegetable Chenopodium. Indian Journal of Genetics and Plant Breeding, 63, 359–360.
5.
Kokanova-NedialkovaZ, NedialkovPT, NikolovSD. (2009) The genus Chenopodium: Phytochemistry, ethnopharmacology and pharmacology. Pharmacognosy Review, 3, 280–306.
6.
DembitskyV, ShkrobI, HanusLO. (2008) Ascaridole and related peroxides from the genus Chenopodium. Biomedical papers of the Medical Faculty of the University Palacký, Olomouc, Czechoslovakia, 152, 209–215.
RastrelliL, AquinoR, AbdoS, ProtoM, De SimoneF, De TommasiN. (1998) Studies on the constituents of Amaranthus caudatus leaves: Isolation and structure elucidation of new triterpenoid saponins and ionol-derived glycosides. Journal of Agricultural and Food Chemistry, 46, 1797–1804
9.
JunkuszewM, OleszekW, JurzystaM, PiancenteS, PizzaC. (1998) Triterpenoid saponins from the seeds of Amaranthus cruentus. Phytochemistry, 49, 195–198
10.
De TommasiN, PiacenteS, Gacs-BaitzE, De SimoneF, PizzaC, AquinoR. (1998) Triterpenoid saponins from Spergularia ramosa. Journal of Natural Products, 61, 323–327.
11.
RastrelliL, PizzaC, SaturninoP, SchettinoO, DiniA. (1995) Studies on the constituents of Amaranthus caudatus (kiwicha) seeds. Isolation and characterization of seven new triterpene saponins. Journal of Agricultural and Food Chemistry, 43, 904–909.
12.
MiyaseT, AndohT, UenoA. (1995) Linderniosides A and B, oleanane saponins from Lindernia pyxidaria. Phytochemistry, 40, 1499–1502.
13.
HoyerKK, DoomsH, BarronL, AbbasAK. (2008) Interleukin-2 in the development and control of inflammatory disease. Immunological Reviews, 226, 19–28
14.
OlejniczakK, KasprzakA. (2008) Biological properties of interleukin 2 and its role in pathogenesis of selected diseases - a review. Medical Science Monitor, 14, RA179–189
15.
SmithKA, PopmihajlovZ. (2008) The quantal theory of immunity and the interleukin-2-dependent negative feedback regulation of the immune response. Immunological Reviews, 224, 124–140
16.
WeissA, WiskocilRL, StoboJD. (1984) The role of T3 surface molecules in the activation of human T cells: a two-stimulus requirement for IL 2 production reflects events occurring at a pre-translational level. Journal of Immunology, 133, 123–128.
17.
TanakaT, NakashimaT, UedaT, TomiiK, KounoI. (2007) Facile discrimination of aldose enantiomers by reversed-phase HPLC. Chemical & Pharmaceutical Bulletin, 55, 899–901
18.
MosmannT. (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. Journal of Immunological Methods, 65, 55–63
19.
KonstantinovSM, EiblH, BergerMR. (1999) BCR-ABL influences the antileukaemic efficacy of alkylphosphocholines. British Journal of Haematology, 107, 365–380.
20.
GillisS, WatsonJ. (1980) Biochemical and biological characterization of lymphocyte regulatory molecules. V. Identification of an interleukin 2-producing human leukemia T cell line. Journal of Experimental Medicine, 152, 1709–1719
21.
MangerB, HardyKJ, WeissA, StoboJD. (1986) Differential effect of cyclosporin A on activation signaling in human T cell lines. Journal of Clinical Investigation, 77, 1501–1506
22.
McIntyreCA, HorneCJ, LawryJ, ReesRC. (1994) The detection of intracytoplasmic interleukin-2 in Jurkat E6.1 and human peripheral blood mononuclear cells using direct conjugate, two-colour, immunofluorescent flow cytometry. Journal of Immunological Methods, 169, 213–220.
23.
YesiladaE, ÜstünO, SezikE, TakaishiY, OnoY, HondaG. (1997) Inhibitory effects of Turkish folk remedies on inflammatory cytokines: interleukin-1α, interleukin-1β and tumor necrosis factor-α. Journal of Ethnopharmacology, 58, 59–73
24.
YesiladaE, TaninakaH, TakaishiY, HondaG, SezikE, MomotaH, OhmotoY, TakiT. (2001) In vitro inhibitory effects of Daphne oleoides ssp. oleoides on inflammatory cytokines and activity-guided isolation of active constituents. Cytokine, 13, 359–364.
