Naturally occurring saponins are a large group of triterpene and steroid glycosides characterized by several biological and pharmacological properties. The Medicago genus represents a valuable source of saponins which have been extensively investigated. This review summarizes the chemical features of saponins from Medicago species and their biological activity, with particular attention to their antimicrobial, insecticidal, allelopathic and cytotoxic effects. Influence of saponins on animal metabolism is also reported.
HostettmannK, MarstonA. (1995) Chemistry and Pharmacology of Natural Products. Saponins. PhillipsonJD, BaxterH (Eds). Cambridge University Press, UK.
3.
MilgateJ, RobertsDCK. (1995) The nutritional and biological significance of saponins. Nutritional Research, 8, 1223–1249.
4.
Lacaille-DuboisMA, WagnerH. (2000) Bioactive saponins from plants: an update. In Studies in Natural Products Chemistry. Vol. 21, Atta-ur-Rahman (Ed). Elsevier, London, UK. 633–687.
5.
FrancisG, KeemZ, MakkarHPS, BeckerK. (2002) The biological action of saponins in animal systems. A review. British Journal of Nutrition, 88, 587–605.
6.
SpragSG, LightME, van StadenJ. (2004) Biological activities and distribution of plant saponins. Journal of Ethnopharmacology, 94, 219–243.
7.
TanakaO, TamuraY, MasudaH, MizutaniK. (1996) Application of saponins in food and cosmetics: saponins of Mohave yucca and Sapindus mukurossi. In Advances in Experimental Medicine and Biology. Saponins Used in Food and Agriculture. Vol. 405. WallerGR, YamasakiK. (Eds). Plenum Press, New-York. 1–11.
8.
San MartinR, BrionesR. (2000) Quality control of commercial quillaja (Quillaja saponaria Molina) extracts by reverse phase HPLC. Journal of the Science of Food and Agriculture, 88, 587–605.
JurzystaM, WallerGR. (1996) Antifungal and haemolytic activity of aerial parts of alfalfa (Medicago) species in relation to saponin composition. In Advances in Experimental Medicine and Biology. Saponins Used in Traditional and Modern Medicine. Vol. 404. WallerGR, YamasakiK. (Eds). Plenum Press, New-York. 565–574.
11.
OleszekW. (1996) Alfalfa saponins: structure, biological activity and chemotaxonomy. In Advances in Experimental Medicine and Biology. Saponins used in Food and Agriculture. Vol. 405. WallerGR, YamasakiK. (Eds). Plenum Press, New-York. 155–170.
12.
TavaA, OdoardiM. (1996) Saponins from Medicago spp.: chemical characterization and biological activity against insects. In Advances in Experimental Medicine and Biology. Saponins Used in Food and Agriculture. Vol. 405. WallerGR, YamasakiK. (Eds). Plenum Press, New-York. 97–109.
13.
TimbekovaAE, IsaevMI, AbubakirovNK. (1996) Chemistry and biological activity of triterpenoid glycosides from Medicago sativa. In Advances in experimental medicine and biology. Saponins Used in Food and Agriculture. Vol. 405, WallerGR, YamasakiK (Eds). Plenum Press, New York USA. 171–182.
14.
ZehaviU, PolacheckI. (1996) Saponins as antimycotic agents: glycosides of medicagenic acid. In Advances in Experimental Medicine and Biology. Saponins Used in Traditional and Modern Medicine. Vol. 404. WallerGR, YamasakiK. (Eds). Plenum Press, New-York. 535–546.
15.
OleszekW. (2000) Alfalfa saponins: Chemistry and Application. In: Phytochemicals as Bioactive Agents. Technomic Publ. Comp., Inc., USA, 167–188.
16.
LesinsKA, LesinsI. (1979) Genus Medicago (Leguminosae). A taxogenetic Study. JunkW. (Ed), Publisher, London.
17.
HeynCC. (1963) The Annual Species of Medicago. Magnes Press, Hebrew University, Jerusalem.
18.
PotterGC, KummerowFA. (1954) Chemical similarity and biological activity of the saponins isolated from alfalfa and soybeans. Science, 120, 224–225.
19.
MorrisRJ, DyeWB, GislerDS. (1961) Isolation, purification and structural activity of an alfalfa root saponins. Journal of Organic Chemistry, 26, 1241–1243.
20.
MorrisRJ, HusseyEW. (1965) A natural glycoside of medicagenic acid. An alfalfa blossom saponin. Journal of Organic Chemistry, 30, 166–168.
21.
GestetnerB. (1971) Structure of a saponin from lucerne (Medicago sativa). Phytochemistry, 10, 2221–2223.
22.
TimbekovaAE, AbubakirovNK. (1984) Triterpene glycosides from alfalfa. I. Medicoside G. A novel bidesmoside from Medicago sativa. Khimiya Prirodnykh Soedinenii, 451–458.
23.
TimbekovaAE, AbubakirovNK. (1985) Triterpene glycosides from alfalfa. II. Medicoside C. Khimiya Prirodnykh Soedinenii, 805–808.
24.
TimbekovaAE, AbubakirovNK. (1986) Triterpene glycosides from alfalfa. VII. Medicoside I. Khimiya Prirodnykh Soedinenii, 607–610.
25.
TimbekovaAE, AbubakirovNK. (1986) Triterpene glycosides of alfalfa. IV. Medicoside J. Khimiya Prirodnykh Soedinenii, 610–613.
26.
KitagawaI, TaniyamaT, MurakamiT, YoshiharaM, YoshikawaM. (1988) Saponin and sapogenol. XLVI. On the constituents of aerial part of american alfalfa, Medicago sativa L. The structure of dehydrosoyasaponin I. Yakugaku Zasshi, 108, 547–551.
27.
MassiotG, LavaudC, Le Men-OlivierL, van BinstG, MillerSPF, FalesHM. (1988) Structural elucidation of alfalfa root saponins by mass spectrometry and nuclear magnetic resonance analysis. Journal of Chemical Society Perkin TransactionI, 3071–3079.
28.
OleszekW, PriceKR, FenwickGR. (1988) Triterpene saponins from the roots of Medicago lupulina L. (black medic trefoil). Journal of Science of Food and Agriculture, 43, 289–297.
29.
LevyM, ZehaviU, NaimM, PolacheckI. (1989) Isolation, structure determination and antifungal activity of a new alfalfa root saponin. Carbohydrate Research, 193, 115–123.
30.
TimbekovaAE, LarinMF, YagudaevMR, AbubakirovNK. (1989) Triterpene glycosides of alfalfa. V. Medicoside H. Khimiya Prirodnykh Soedinenii, 673–677.
31.
OleszekW, PriceKR, ColquhounIJ, JurzystaM, PloszynskiM, FenwickGR. (1990) Isolation and identification of alfalfa (Medicago sativa L.) root saponins: their activity in relation to a fungal bioassay. Journal of Agricultural and Food Chemistry, 38, 1810–1817.
32.
TimbekovaAE, VerechaginAL, SemenovAA, AbubakirovNK. (1990) Triterpene glycosides of alfalfa. VI. Medicoside LKhimiya Prirodnykh Soedinenii, 221–227.
33.
MahatoSB. (1991) Triterpenoid saponins from Medicago hyspida. Phytochemistry, 30, 3389–3393.
34.
MassiotG, LavaudC, BessonV, Le Men-OlivierL, van BinstG. (1991) Saponins from aerial parts of alfalfa (Medicago sativa). Journal of Agricultural and Food Chemistry, 39, 78–82.
35.
MassiotG, LavaudC, BenkhaledM, Le Men-OlivierL. (1992) Soyasaponin VI, a new maltol conjugate from alfalfa and soyabean. Journal of Natural Products, 55, 1339–1341.
36.
OleszekW, JurzystaM, PloszynskiM, ColoquhounIJ, PriceKR, FenwickGR. (1992) Zahnic acid tridesmoside and other dominant saponins from alfalfa (Medicago sativa L.) aerial parts. Journal of Agricultural and Food Chemistry, 40, 191–196.
37.
TimbekovaAE, ShashkovAS, AbubakirovNK. (1993) Triterpene glycosides from alfalfa. VII. Medicosides E and F. Khimiya Prirodnykh Soedinenii, 701–705.
38.
KinjoJ, UemuraH, NakamuraM, NoharaT. (1994) Two new triterpenoidal glycosides from Medicago polymorpha L. Chemical and Pharmacological Bulletin, 42, 1339–1341.
39.
BialyZ, JurzystaM, OleszekW, PiacenteS, PizzaC. (1999) Saponins in alfalfa (Medicago sativa L.) root and their structural elucidation. Journal of Agricultural and Food Chemistry, 47, 3185–3192.
40.
HuhmanDV, SumnerLW. (2002) Metabolic profiling of saponins in Medicago sativa and Medicago truncatula using HPLC coupled to an electrospray ion-trap mass spectrometer. Phytochemistry, 59, 347–360.
41.
ZbigniewB, JurzystaM, MellaM, TavaA. (2004) Triterpene saponins from aerial parts of Medicago arabica L. Journal of Agricultural and Food Chemistry, 52, 1095–1099.
42.
HuhmanDV, BerhowMA, SumnerLW. (2005) Quantification of saponins in aerial and subterranean tissues of Medicago truncatula. Journal of Agricultural and Food Chemistry, 53, 1914–1920.
43.
KapustaI, BogdanJ, StochmalA, OleszekW. (2005) Determination of saponins in aerial parts of barrel medic (Medicago truncatula) by liquid chromatography-electrospray ionization/mass spectrometry. Journal of Agricultural and Food Chemistry, 53, 7654–7660.
44.
KapustaI, StochmalA, PerroneA, PiacenteS, PizzaC, OleszekW. (2005) Triterpene saponins from barrel medic (Medicago truncatula) aerial parts. Journal of Agricultural and Food Chemistry, 53, 2164–2170.
45.
TavaA, MellaM, AvatoP, ArgentieriMP, BialyZ, JurzystaM. (2005) Triterpene saponins from leaves of Medicago arborea L. Journal of Agricultural and Food Chemistry, 53, 9954–9965.
46.
BialyZ, JurzystaM, MellaM, TavaA. (2006) Triterpene Saponins from the Roots of Medicago hybrida. Journal of Agricultural and Food Chemistry, 54, 2520–2526.
47.
PedersenMW. (1975) Relative quantity and biological activity of saponins in germinated seeds, roots, and foliage of alfalfa. Crop Science, 15, 541–543.
48.
GorskiPM, MierschJ, PloszynskiM. (1991) Production and biological activity of saponins and canaverine in alfalfa seedlings. Journal of Chemical Ecology, 17, 1135–1143.
49.
OleszekW. (1998) Composition and quantitation of saponins in alfalfa (Medicago sativa L.) seedlings. Journal of Agricultural and Food Chemistry, 46, 960–962.
50.
BerrangB, DavisKHJr, WallME, HansonCH, PedersenME. (1974) Saponins of two alfalfa cultivars. Phytochemistry, 13, 2253–2260.
51.
QuaziHM (1975) Effect of cultivar and season on the concentration of saponins in lucerne (Medicago sativa L.). New Zealand Journal of Agricultural Research, 18, 227–232.
52.
TavaA, OleszekW, JurzystaM, BerardoN, OdoardiM. (1993) Alfalfa saponins and sapogenins: isolation and quantification in two different cultivars. Phytochemical Analysis, 4, 269–274.
53.
TavaA, PecettiL. (1998) Hemolytic activity and saponin content in lucerne (Medicago sativa complex) genotypes. Journal of Genetics and Breeding, 52, 33–37.
54.
TavaA, OdoardiM, OleszekW. (1999) Seasonal changes of saponin content in five alfalfa (Medicago sativa) cultivars. Agricoltura Mediterranea, 129, 111–116.
55.
PecettiL.TavaA, RomaniM, De BenedettoMG, CorsiP. (2006) Variety and environment effects on the dynamics of saponins in lucerne (Medicago sativa L.). European Journal of Agronomy, 25, 187–192
56.
JurzystaM, BurdaS, OleszekW, PloszynskiM. (1988) The chemotaxonomic significance of laricytrin and medicagenic acid in the tribe Trigonellae. Canadian Journal of Botany, 66, 363–367.
57.
JurzystaM, SmallE, NozzolilloC. (1988) The evolution of hemolytic saponin content in wild and cultivated alfalfa (Medicago sativa, Fabaceae). Economic Botany, 44, 226–235.
58.
SmallE, JurzystaM, NozzolilloC. (1990) Hemolysis, a sinapomorphic discriminator for an expanded genus Medicago (Leguminosae). Taxon, 37, 354–363.
59.
JurzystaM, BurdaS, OleszekW, PloszynskiM. (1992) Chemical composition of seed saponins as a guide to the classification of Medicago species. Canadian Journal of Botany, 70, 1384–1387.
60.
WalterED, Van AttaGR, ThompsonCR, MaclayWD. (1954) Alfalfa saponins. Journal of the American Chemical Society, 76, 2271–2273.
61.
JurzystaM. (1973) Isolation and chemical characterization of saponins from lucerne seeds (Medicago media Pers.)Acta Societatis Botanicorum Poloniae, 42, 201–207.
62.
GorskyPM, JurzystaM, BurdaS, OleszekW, PloszynnskyM. (1984) Studies on Medicago lupulina saponins. 2. Isolation, chemical characterization and biological activity of saponins from Medicago lupulina tops. Acta Societatis Botanicorum Poloniae, 53, 527–533.
63.
JurzystaM, NowackiE. (1979) Saponins in the genus Medicago. Acta Agrobotanica, 32, 13–17.
64.
JurzystaM. (1979) Haemolytic micromethod for rapid estimation of toxic alfalfa saponins. Acta Agrobotanica, 32, 5–11.
65.
ZimmerDE, PedersonMW, McGuireCF. (1967) A bioassay for alfalfa saponins using the fungus Trichoderma viride Pers. Crop Science, 7, 223–224.
66.
PracrosP. (1988) Mesure de l'activité des saponins de la lucerne par les larves du ver de la farine: Tenebrio molitor L. (Colèoptére, Tenebrionidae). I. Comparaison avec les résultats de divers tests biologiques. Agronomie, 8, 257–263.
67.
NowackaJ, OleszekW. (1994) Determination of alfalfa (Medicago sativa L.) saponins by high performance liquid chromatography. Journal of Agricultural and Food Chemistry, 42, 727–729.
68.
JurzystaM.JurzystaA. (1978) Gas-liquid chromatography of trimethylsilyl ethers of soyasapogenols and medicagenic acid. Journal of Chromatography, 148, 517–520.
69.
RaoD, BorisG. (1987) Simple gas chromatographic method for the determination of medicagenic acid in alfalfa (Medicago sativa). Journal of Chromatography, 410, 169–175.
70.
TavaA, ChiariM, OleszekW. (2000) Separation of alfalfa (Medicago sativa L.) saponins as their borate complexes by capillary electrophoresis. In Saponins in Food, Feedstuffs and Medicinal Plants. Chapter 5, OleszekW, MarstonA (Eds). Kluwer Academic Publishers, Dordrecht The Netherlands. 43–56.
71.
LeeMK, LingYC, JurzystaM, WallerGR. (1996) Saponins from alfalfa, clover, and mungbeans analysed by electrospray ionization-mass spectrometry as compared with positive and negative FAB-mass spectrometry. In Advances in Experimental Medicine and Biology. Saponins Used in Food and Agriculture. Vo l 405, WallerGR, YamasakiK (Eds). Plenum Press, New York USA. 353–364.
72.
AgrawalPK. (1996) A systematic NMR approach for the determination of the molecular structure of steroidal saponins. In Advances in Experimental Medicine and Biology. Saponins Used in Food and Agriculture. Vo l 405, WallerGR, YamasakiK (Eds). Plenum Press, New York USA. 299–315.
73.
MellaM, JurzystaM, RicciM, TavaA. (2002) NMR investigation of saponins and sapogenins from Medicago species. Proceedings of XXXII National Congress on Magnetic Resonance. Pavia, Italy P-3.
74.
TavaA, MellaM, BialyZ, JurzystaM. (2003) Stability of saponins in alcoholic solutions: ester formation as artifacts. Journal of Agricultural and Food Chemistry, 51, 1797–1800.
75.
TorsellKBG. In Natural Product Chemistry - A Mechanistic, Biosynthetic and Ecological Approach. Swedish Pharmaceutica Society, 1997.
76.
MorrisRJ, TankersleyDL. (1963) The synthesis of the β-D-glucoside of medicagenic acid, an alfalfa root saponin. The Journal of Organic Chemistry, 28, 240–242.
77.
NowackiE, JurzystaM, Dietrych-SzostakD. (1976) Zur biosynthese der medicagensaure in keimenden luzernesamen. Biochemie und Physiologie der Pflanzen, 156, 183–186.
78.
SuzukiH, AchnineL, XuR, MatsudaSPT, DixonRA. (2002) A genomic approach to the early stages of triterpene saponin biosynthesis in Medicago truncatula. The Plant Journal, 32, 1033–1048.
79.
OsbournA. (1996) Saponins and plant defence - a soap story. Trends in Plant Science, 1, 4–9.
80.
OsbournA. (2003) Saponins in cereals. Phytochemistry, 62, 1–4.
81.
WinaE, MuetzelS, BeckerK. (2005) The impact of saponin-containing plant materials on ruminant production-A review. Journal of Agricultural and Food Chemistry, 53, 8093–8105.
82.
LevyM, ZehaviU, NaimM, PolacheckI. (1986) An improved procedure for the isolation of medicagenic acid 3-O-β-D-Glucopyranoside from alfalfa roots and its antifungal activity on plant pathogens. Journal of Agricultural and Food Chemistry, 34, 960–963
83.
NonakaM. (1986) Variable sensitivity of Trichoderma viride to Medicago sativa saponins. Phytochemistry, 25, 73–75.
84.
GruizK. (1996) Fungitoxic activity of saponins: practical use and fundamental principles. In Advances in Experimental Medicine and biology. Saponins Used in traditional and modern medicine. Vol. 404. WallerGR, YamasakiK. (Eds). Plenum Press, New-York. 527–534.
85.
JurzystaM, BialyZ. (1999) Antifungal and haemolytic activity of roots of alfalfa (Medicago spp.) in relation to saponin composition. In Modern fungicides and antifungal compounds II. LyrH, RusselPE, SislerHD (Eds). Intercept: Andover, UK. 445–451.
86.
GestetnerB, AssaY, HenisY, BirkY, BondiA. (1971) Lucerne saponins IV.- Relationship between their chemical constitution, and haemolytic and antifungal activities. Journal of Agricultural and Food Chemistry, 22, 168–172.
87.
AssaY, GestetnerB, ChetI, HenisY. (1972) Fungistatic activity of Lucerne saponins and digitonin as related to sterols. Life Sciences, 11, Part II, 637–647.
88.
LevanonD, HenisY, OkonY, DovratA. (1982) Alfalfa saponins and microbial transformations of nitrogen in peat. Soil Biology & Biochemistry, 14, 501–504.
89.
MartyniukS, JurzystaM, BialyZ, WróblewskaB. (1995) Alfalfa root saponins affect the growth and sporulation of Cephalosporium gramineum. In Environmental Biotic Factors in Integrated Plant Disease Control. MankaM (Ed). The Polish Phytopathological Society, Poznan. 395–398.
90.
MartyniukS, WróblewskaB, JurzystaM, BialyZ. (1995) Saponins as inhibitors of cereal pathogens: Gaeumannomyces graminis v. tritici and Cephalosporium gramineum. In Modern Fungicides and Antifungal Compounds. LyrH, RusselPE, SislerHD (Eds.) Intercept Ltd., UK.193–197.
91.
MartyniukS, JurzystaM, WróblewskaB. (1999) Influence of powdered aerial parts of various Medicago species on the growth of Gaeumannomyces graminis and Cephalosporium gramineum. Bulletin of the Polish Academy of Sciences, Biological Sciences, 47, 2–4.
92.
SaniewskaA, JurzystaM, BialyZ. (2001) Differential antifungal activity of alfalfa (Medicago sativa L.) saponins originated from roots and aerial parts of some ornamental plant pathogens. Acta Agrobotanica, 54, 31–43.
93.
SaniewskaA, JurzystaM, BialyZ. (2003) The effect of alfalfa (Medicago sativa) saponins on Botrytis tulipae and Phoma narcissi growth. Phytopathologica Polonica, 27, 15–27.
94.
MartyniukS, BialyZ, JurzystaM. (2004) Antifungal activity of aerial parts and saponins of Medicago ssp. against Cephalosporium gramineum. Allelopathy Journal, 13, 75–82.
95.
SaniewskaA, JareckaZ, BialyZ, JurzystaM. (2005) Antifungal activity of saponins from Medicago arabica L. shoots against some pathogens. Allelopathy Journal, 16, 105–112.
96.
PolacheckI, ZehaviU, NaimM, LevyM, EvronR. (1986) Activity of compound G2 isolated from alfalfa roots against medically important yeasts. Antimicrobial Agents and Chemotherapy, 30, 290–294.
97.
PolacheckI, ZehaviU, NaimM, LevyM, EvronR. (1986) The susceptibility of Cryptococcus neoformans to an antimycotic agent (G2) from alfalfa. Zentralblatt fur Bakteriologie, Mikrobiologie und Hygiene. Series A, 261, 481–486.
98.
EvronR, PolacheckI, GuizieM, LevyM, ZehaviU. (1988) Activities of compound G2 isolated from alfalfa roots against dermatophytes. Antimicrobial Agents and Chemotherapy, 32, 1586–1587.
99.
EvronR, GuizieM, ZehaviU, PolacheckI. (1990) Activity of compound G2 isolated from alfalfa roots in experimental dermatophyte infection. Antimicrobial Agents and Chemotherapy, 34, 1600–1601.
100.
PolacheckI, ZehaviU, NaimM, LevyM, EvronR. (1986) The susceptibility of Cryptococcus neoformans to an antimycotic agent (G2) from alfalfa. Zentralblatt fur Bakteriologie, Mikrobiologie und Hygiene. Series A, 261, 481–486.
101.
SpiewakR, SzostakW, JurzystaM, BialyZ. (2000) Inhibiting action of medicagon acid 3-glucoside on the growth of Scropulariopsis brevicaulis in vitro. Abstract Book, 10thInternational Mycological Symposium of PDS – Mycology 2000, Poland, pg 113.
102.
SpiewakR, SzostakW, JurzystaM, BialyZ. (2000) Inhibiting action of medicagon acid 3-glucoside on the growth of Trichophyton mentagrophytes in vitro. Abstract Book, 10thInternational Mycological Symposium of PDS – Mycology 2000, Poland, pg 114.
HoughtonPJ, PatelN, CheungCY, JurzystaM, BialyZ. (2005) Antifungal activity of saponins from Medicago species. Abstract Book, 53rdGA Annual Congress, Florence, p. 192.
105.
HoaglandR. (2001) Effects of alfalfa saponins on in vitro physiological activity of soil and rhizosphere bacteria. Journal of Crop Protection, 4, 349–361.
ApplebaumSW, MarcoS, BirkY. (1969) Saponins as a possible factor of resistance of legume seed to attack of insects. Journal of Agricultural and Food Chemistry, 17, 618–621.
108.
AgrelliJ, OleszekW, StochmalA, OlsenM, AndersonP. (2003) Herbivore-induced responses in alfalfa (Medicago sativa). Journal of Chemical Ecology, 29, 303–320.
109.
ApplebaumSW, BirkY. (1979) In Herbivores. Their Interaction with Secondary Plant Metabolites. RosenthalGA, JanzenDH (Eds). Academic Press, New York. 539–566.
110.
OakenfullD, SidhuGS. (1989) Saponins. In Toxicant of Plant Origin. Volume II. Glycosides.CheekePR (Ed), CRC Press, Boca Raton, Florida (USA), 97–141.
111.
SutherlandORW, HutchinsRFN, GreenfieldWJ. (1982) Effect of lucerne saponins and lotus condensed tannins of survival of grass grub, Costelytra zealandica. New Zealand Journal of Zoology, 9, 511–516.
112.
HorberE, LeathKT, BerrangB, MacarianV, HansonCH. (1974) Biological activities of saponin components from DuPuits and Lahontan alfalfa. Entomology Experimental & Application, 17, 410–424.
113.
PracrosP. (1988) Mesure de l'activitè des saponines de la luzerne par les larves du ver de farine: Tenebrio molitor L. (Coléoptère, Tenebriolidae). II – Recherche des fractions de saponines responsables des effets antinutritionnelles observès. Agronomie, 8, 793–799.
114.
WaligoraD, KrzymanskaJ. (1994) The influence of secondary plant substances: glucosinolates, alkaloids and saponins on the feeding of Colorado potato beetle (Leptinotarsa decemlineata Say). Proc. XXXIV Session IOR, vol. II, Poznan, pp. 9–12.
115.
SzczepanikM, KrystkowiakK, JurzystaM, BialyZ. (2001) Biological activity of saponins from alfalfa tops and roots against colorado potato beele larvae. Acta Agrobotanica, 54, 35–45.
116.
SzczepanikM, BialyZ, JurzystaM. (2004) The insecticidal activity of saponins from varius Medicago spp. against Colorado potato beetle, Leptinotarsa decemlineata Say. Allelopathy Journal, 14, 177–186.
117.
PuszkarL, JastrzebskiA, JurzystaM, BialyZ. (1994) Alfalfa saponins as a chance in the integrated hop protection. Proc. XXXIV Session IOR, vol. II, Poznan, pp. 255–259.
118.
NozzolilloC, ArnasonJT, CamposC, DonskovN, JurzystaM. (1997) Alfalfa leaf saponins and insect resistance. Journal of Chemical Ecology, 21, 995–1002.
119.
AdelMM, Sehnalf, JurzystaM. (2000) Effects of alfalfa saponins on the moth Spodoptera littoralis. Journal of Chemical Ecology, 26, 1065–1078.
120.
PodolskaG, BialyZ, JurzystaM, WallerGR. (2003) Effect of application of alfalfa root saponins aqueous solution on the plant structure, yield and quality of winter wheat. Allelopathy Journal, 11, 171–184.
121.
WallerGR. (1989) Biochemical frontiers of allelopathy. Biologia Plantarum, 31, 418–447.
122.
OleszekW, JurzystaM, GorskiPM. (1992) Alfalfa saponins the allelopathic agents. In Allelopathy: Basic and Applied Aspects.RizviSJH, RizviV. (Eds). Chapman & Hall, London. 151–167.
123.
OleszekW. (1993) Allelopathic potential of alfalfa (Medicago sativa) saponins: their relation to antifungal and hemolytic activites. Journal of Chemical Ecology, 19, 1063–1074.
124.
OleszekW, HoaglandRE, ZablotowiczRM. (1999) Ecological significance of plant saponins. In: Principles and Practices in Plant Ecology. Allelochemical Interactions. InderjitDakshini KMM, FoyCL (Eds.). CRC Press LLC, Washington DC, 451–465.
125.
MishustinBN, NaumovaAN. (1955) Secretion of toxic substances by alfalfa and their effect on cotton and soil microflora. Akademia Nauk USSR Izvestija, Seriya Biologicheskaya, 6, 3–9.
126.
GuenziWD, KehrWR, McCallaTM. (1964) Water-soluble phytotoxic substances in alfalfa forage:variation with variety, cutting, year, and stage of growth. Agronomy Journal, 56, 499–500.
127.
OleszekW, JurzystaM. (1987) The allelopathic potential of alfafa root medicagenic acid glycosides and their fate in soil environments. Plant and Soil, 98, 67–80.
128.
Wyman-SimpsonCL, WallerGR, JurzystaM, McPhersonJK, YoungCC. (1991) Biological activity and chemical isolation of root saponins of six cultivars of alfalfa (Medicago sativa L.). Plant and Soil, 135, 83–94.
129.
WallerGR, JurzystaM, ThorneRLZ. (1993) Allelopathic activity of root saponins from alfalfa (Medicago sativa L.) on weeds and wheat. Botany Bulletin Academia Sinica, 34, 1–11.
130.
WallerGR, JurzystaM, ThorneRLZ. (1995) Root saponins from alfalfa (Medicago sativa L.) and their allelopathic activity on weeds and wheat. Allelopathy Journal, 2, 21–30.
ChungI-M, SeiglerD, MillerDA, KyungS-H. (2000) Autotoxic compounds from fresh alfalfa leaf extracts: identification and biological activity. Journal of Chemical Ecology, 26, 315–327.
135.
XuanTD, TsuzukiE, TeraoH, MatsuoM, KhanhTD. (2003) Correlation between growth inhibitory exhibition and suspected allelochemicals (phenolic compounds) in the extract of alfalfa (Medicago sativa L.). Plant Production Science, 6, 165–171.
136.
PriceKR, JohnsonIT, FenwickGR. (1987) The chemistry and biological significance of saponins in food and feedstuffs. CRC Critical Reviews in Food Science and Nutrition, 26, 27–135.
137.
CheekePR. (1996) Biological effects of feed and forage saponins and their impacts on animal production. In Advances in experimental medicine and biology. Saponins Used in Food and Agriculture. Vo l 405, WallerGR, YamasakiK (Eds). Plenum Press, New York USA. 377–385.
138.
SenS, MakkarHPS, BeckerK. (1998) Alfalfa saponins and their implication in animal nutrition. Journal of Agricultural and Food Chemistry, 46, 131–140.
139.
LuCD, JorgensenNA. (1987) Alfalfa saponins affect site and extent of nutrient digestion in ruminants. Journal of Nutrition, 117, 919–927.
140.
LuCD, TsaiLS, SchaeferDM, JorgensenNA. (1987) Alteration of fermentation in continuous culture of mixed rumen bacteria. Journal of Dairy Science, 70, 799–805.
141.
WallaceRJ, McEwanNR, McIntoshFM, TeferedegneB, NewboldCJ. (2002) Natural products as manipulators of rumen fermentation. Asian-Australian Journal of Animal Science, 15, 1458–1468.
142.
PedersenMW, ZimmerDE, McAllisterDR, AndersonJO, WildingMD, TaylorGA, McGuireCF. (1967) Comparative studies of several alfalfa varieties using chemical and biochemical assay. Crop Science, 7, 349–352.
143.
PedersenMW, WangL. (1971) Modification of saponin content of alfalfa through selection. Crop Science, 11, 833–835.
144.
HowardRE. (1988) Antiquality factors and nonnutritive chemical components. In Alfalfa and alfalfa Improvements.HansonAA, BarnesDK, HillRRJr. (Eds). ASA Inc. CSSA Inc. SSSA Inc. Publishers, Madison, USA. 493–514.
145.
MajakW, FesserAC, GoplenBP, PedersenMW. (1980) Relationship between ruminant bloat and composition of alfalfa herbage. II. Saponins. Canadian Journal of Animal Science, 60, 699–708.
146.
OleszekW, Nowacka-ZaborskaJM, MintaM, ZmudzkiJ. (1995) Effect of alfalfa saponin-zanhic acid tridesmoside on hamsters (Mesocricetus auratus). In Current trends in Fruit and Vegetable Phytochemistry. Garcia-VigueraC, CastanerM, GilMI, FerrerasF, Tomas-BarberanFA (Eds). Consejo Superior Investigaciones Cientificas, Madrid, Spain. 293–297.
147.
OleszekW, NowackaJ, GeeJM, WortleyGM, JohnsonIT. (1994) Effects of some purified alfalfa (Medicago sativa) saponins on transmural potential difference in mammalian small intestine. Journal of Science of Food and Agriculture, 65, 35–39.
148.
MalinowMR, McLaughlinP, PapworthL, StaffordC, KohlerGO, LivingstonAL, CheekePR. (1977) Effects of alfalfa saponins on intestinal cholesterol adsorption in rats. The American Journal of Clinical Nutrition, 30, 2061–2067.
149.
MalinowMR, ConnorWE, McLaughlinP, StaffordC, LinDS, LivingstonAL, KohlerGO, McNultyWP. (1981) Cholesterol and bile acid balance in Macaca fascicularis: effects of alfalfa saponins. The Journal of Clinical Investigation, 67, 156–162.
150.
SrokaZ, JurzystaM, TylczJ, Rzadkowska-BodalskaH. (1997) Stimulation of pancreatic lipase activity by saponins isolated from M. sativa L. Zeitschrift fur Naturforschung, 52c, 235–239.
151.
BaderG, PlohmannB, HillerK, FranzF. (1996) Cytotoxicity of triterpenoid saponins. Part 1: activities against tumor cells in vitro and haemolytic index. Pharmazie, 51, 414–417.
152.
SinguaroliI. (2002) Attività citotossica di saponine da M. sativa in linee tumorali umane. Doctoral Thesis. Università degli Studi di Pavia, Facoltà di Farmacia, Dipartimento di Farmacologia Sperimentale ed Applicata.
153.
GaidiG, CorreiaM, ChauffertB, BeltramoJL, WagnerH, Lacaille-DuboisMA. (2002) Saponin-mediated potentiation of cisplatin accumulation and cytotoxicity in human colon cancer cells. Planta Medica, 68, 70–72.
154.
MessinaMJ, PerskyV, SetchellKDR, BarnesS. (1994) Soy intake and cancer risk: a review of the in vitro and in vivo data. Nutrition and Cancer, 21, 113–131.
155.
RaoAV, SungMK. (1995) Saponins as anticarcinogens. Journal of Nutrition, 125, 117s–124s.
156.
FournierDB, ErdmanJWJr, GordonGB. (1998) Soy, its components, and cancer prevention: a review of the in vitro, animal, and human data. Cancer Epidemiology Biomarkers Prevention, 7, 1055–1065.
157.
GestneterB, BirkY, TencerY. (1968) Soybean saponins. Fate of ingested soybean saponins and the physiological aspect of their hemolytic activity. Journal of Agricultural and Food Chemistry, 16, 1031–1035.
158.
SungMK, KendallCWC, KooMM, RaoAV. (1995) Effect of soybean saponins and gypsophylla saponin on growth and viability of colon carcinoma cells in culture. Nutrition and Cancer, 23, 259–270.
159.
OhYJ, SungMK. (2001) Soybean saponins inhibit cell proliferation by suppressing PKC activation and induce differentiation of HT-21 human colon adenocarcinoma cells. Nutrition and Cancer, 39, 132–138.
160.
KoratkarR, RaoAV. (1997) Effect of soya bean saponins on azoxymethane-induced preneoplastic lesions in the colon of mice. Nutrition and Cancer, 27, 206–209.
161.
KonoshimaT, KokumaiM, KozukaM, TokudaH, NishinoH, IwashimaA. (1992) Anti-tumor-promoting activities of afromosin and soyasaponin I isolated from Wisteria brachybotrys. Journal of Natural Products, 55, 1776–1778.
162.
EliasR, De MeoM, Vidal-OllivierE, LagetM, BalansardG, DumenilG. (1990) Antimutagenic activity of some saponins isolated from Calendula officinalis L., C. arvensis L. and Hedera helix L. Mutagenesis, 5, 327–331.
163.
DanloyS, Quetin-LeclercqJ, CouckeP, De Pauw-GilletMC, EliasR, BalansardG, AngenotL, BassleerR. (1994) Effects of α-hederin, a saponin extracted from Hedera helix, on a cell cultured in vitro. Planta Medica, 60, 45–49.
164.
ParkHJ, KwonSH, LeeJH, LeeKH, MiyamotoKI, LeeKT. (2001) Kalopanaxsaponin A is a basic saponin structure for the anti-tumor activity of hederagenin monodesmosides. Planta Medica, 67, 118–121.
165.
KonoshimaT, KozukaM, HarumaM, ItoK. (1991) Constituents of leguminous plants, XIII. New triterpenoid saponins from Wisteria brachybotrys. Journal of Natural Products, 54, 830–836.
166.
CzeczotH, Rahden-StaronI, OleszekW, JurzystaM. (1994) Isolation and studies of the mutagenic activity of saponins in the Aimes test. Acta Poloniae Pharmaceutica – Drug Research, 51, 133–136.
