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Volumn 1760, Issue 9, 2006, Pages 1418-1427

Structure-activity relationships of some hederagenin diglycosides: Haemolysis, cytotoxicity and apoptosis induction

Author keywords

Hederin; Cytotoxicity; Haemolysis; Hederagenin; KB cell; Saponin

Indexed keywords

7 ETHYL 10 HYDROXYCAMPTOTHECIN; 7 ETHYL 10 HYDROXYCAMPTOTHECIN GLUCURONIDE; ALPHA HEDERIN; ARABINOSE; GLUCOSE; GLUCOSIDE; GLYCOSIDE; HEDERAGENIN; SAPONIN; UNCLASSIFIED DRUG;

EID: 33748697487     PISSN: 03044165     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbagen.2006.05.004     Document Type: Article
Times cited : (129)

References (43)
  • 2
    • 0018082759 scopus 로고
    • The susceptibility of cholesterol-depleted erythrocytes to saponin and sapogenin hemolysis
    • Segal R., and Milo-Goldzweig I. The susceptibility of cholesterol-depleted erythrocytes to saponin and sapogenin hemolysis. Biochim. Biophys. Acta 512 (1978) 223-226
    • (1978) Biochim. Biophys. Acta , vol.512 , pp. 223-226
    • Segal, R.1    Milo-Goldzweig, I.2
  • 3
    • 0018576820 scopus 로고
    • Interaction of saponins with red blood cells as well as with the phosphatidylcholine liposomal membranes
    • Nakamura T., Inoue K., Nojima S., Sankawa U., Shoji J., Kawasaki T., et al. Interaction of saponins with red blood cells as well as with the phosphatidylcholine liposomal membranes. J. Pharm. Dyn. 2 (1979) 374-382
    • (1979) J. Pharm. Dyn. , vol.2 , pp. 374-382
    • Nakamura, T.1    Inoue, K.2    Nojima, S.3    Sankawa, U.4    Shoji, J.5    Kawasaki, T.6
  • 4
    • 0016168851 scopus 로고
    • Ultrastructure of membrane lesions in immune lysis, osmotic lysis and drug-induced lysis
    • Seeman P. Ultrastructure of membrane lesions in immune lysis, osmotic lysis and drug-induced lysis. Fed. Proc. 33 (1974) 2116-2124
    • (1974) Fed. Proc. , vol.33 , pp. 2116-2124
    • Seeman, P.1
  • 5
    • 37049052069 scopus 로고
    • Action of saponin on biological cell membranes
    • Glauert A.M., Dingle J.T., and Lucy J.A. Action of saponin on biological cell membranes. Nature 8 (1962) 953-955
    • (1962) Nature , vol.8 , pp. 953-955
    • Glauert, A.M.1    Dingle, J.T.2    Lucy, J.A.3
  • 6
    • 0014581508 scopus 로고
    • Uber die strukturspezifität der saponinhämolyse: I. Triterpensaponine und-aglykone
    • Schlösser E., and Wulff G. Uber die strukturspezifität der saponinhämolyse: I. Triterpensaponine und-aglykone. Z. Naturforsch. 24b (1969) 1284-1290
    • (1969) Z. Naturforsch. , vol.24 b , pp. 1284-1290
    • Schlösser, E.1    Wulff, G.2
  • 8
    • 16644395178 scopus 로고    scopus 로고
    • Synthesis and hemolytic activity of some hederagenin diglycosides
    • Chwalek M., Plé K., and Voutquenne-Nazabadioko L. Synthesis and hemolytic activity of some hederagenin diglycosides. Chem. Pharm. Bull. 52 (2004) 965-971
    • (2004) Chem. Pharm. Bull. , vol.52 , pp. 965-971
    • Chwalek, M.1    Plé, K.2    Voutquenne-Nazabadioko, L.3
  • 9
    • 0029692094 scopus 로고    scopus 로고
    • Structure-activity relationships of synthetic saponins
    • Takechi M., Uno C., and Tanaka Y. Structure-activity relationships of synthetic saponins. Phytochemistry 41 (1996) 121-123
    • (1996) Phytochemistry , vol.41 , pp. 121-123
    • Takechi, M.1    Uno, C.2    Tanaka, Y.3
  • 10
    • 0343114291 scopus 로고    scopus 로고
    • Adjuvant and haemolytic activities of 47 saponins derived from medicinal and food plants
    • Oda K., Matsuda H., Murakami T., Katayama S., Ohgitani T., and Yoshikawa M. Adjuvant and haemolytic activities of 47 saponins derived from medicinal and food plants. J. Biol. Chem. 381 (2000) 67-74
    • (2000) J. Biol. Chem. , vol.381 , pp. 67-74
    • Oda, K.1    Matsuda, H.2    Murakami, T.3    Katayama, S.4    Ohgitani, T.5    Yoshikawa, M.6
  • 14
    • 0001664333 scopus 로고
    • Structure-activity relationships of synthetic methyl oleanolate glycosides
    • Takechi M., and Tanaka Y. Structure-activity relationships of synthetic methyl oleanolate glycosides. Phytochemistry 31 (1992) 3789-3791
    • (1992) Phytochemistry , vol.31 , pp. 3789-3791
    • Takechi, M.1    Tanaka, Y.2
  • 16
    • 0014829846 scopus 로고
    • Effect of ester groups on the haemolytic action of sapogenins-II: esterification with bifunctional acids
    • Segal R., Milo-Goldzweig I., Schupper H., and Zaitschek D.V. Effect of ester groups on the haemolytic action of sapogenins-II: esterification with bifunctional acids. Biochem. Pharmacol. 19 (1970) 2501-2507
    • (1970) Biochem. Pharmacol. , vol.19 , pp. 2501-2507
    • Segal, R.1    Milo-Goldzweig, I.2    Schupper, H.3    Zaitschek, D.V.4
  • 17
    • 85010180204 scopus 로고
    • Pericarp saponins of Akebia quinata DECNE. I. Glycosides of hederagenin and oleanolic acid
    • Higuchi R., and Kawasaki T. Pericarp saponins of Akebia quinata DECNE. I. Glycosides of hederagenin and oleanolic acid. Chem. Pharm. Bull. 24 (1976) 1021-1032
    • (1976) Chem. Pharm. Bull. , vol.24 , pp. 1021-1032
    • Higuchi, R.1    Kawasaki, T.2
  • 18
    • 0018820435 scopus 로고
    • Saponins with molluscicidal activity from Hedera helix L.
    • Hostettmann K. Saponins with molluscicidal activity from Hedera helix L. Helv. Chim. Acta 63 (1980) 606-609
    • (1980) Helv. Chim. Acta , vol.63 , pp. 606-609
    • Hostettmann, K.1
  • 21
    • 0035083008 scopus 로고    scopus 로고
    • Kalopanaxsaponin A is a basic saponin structure for the anti-tumor activity of hederagenin monodesmosides
    • Park H.-J., Kwon S.-H., Lee J.-H., Lee K.-H., Miyamoto K., and Lee K.-T. Kalopanaxsaponin A is a basic saponin structure for the anti-tumor activity of hederagenin monodesmosides. Planta Med. 67 (2001) 118-121
    • (2001) Planta Med. , vol.67 , pp. 118-121
    • Park, H.-J.1    Kwon, S.-H.2    Lee, J.-H.3    Lee, K.-H.4    Miyamoto, K.5    Lee, K.-T.6
  • 22
    • 0036676754 scopus 로고    scopus 로고
    • In vitro activity of hederacolchisid A1 compared with other saponins from Hedera colchica against proliferation of human carcinoma and melanoma cells
    • Barthomeuf C., Debiton E., Mshvildadze V., Kemertelidze E., and Balansard G. In vitro activity of hederacolchisid A1 compared with other saponins from Hedera colchica against proliferation of human carcinoma and melanoma cells. Planta Med. 68 (2002) 672-675
    • (2002) Planta Med. , vol.68 , pp. 672-675
    • Barthomeuf, C.1    Debiton, E.2    Mshvildadze, V.3    Kemertelidze, E.4    Balansard, G.5
  • 24
    • 16644396783 scopus 로고    scopus 로고
    • Structure-activity relationship of oleanane disaccharides isolated from Akebia quinata versus cytotoxicity against cancer cells and NO inhibition
    • Jung H.-J., Lee C.O., Lee K.-T., Choi J., and Park H.-J. Structure-activity relationship of oleanane disaccharides isolated from Akebia quinata versus cytotoxicity against cancer cells and NO inhibition. Biol. Pharm. Bull. 27 (2004) 744-747
    • (2004) Biol. Pharm. Bull. , vol.27 , pp. 744-747
    • Jung, H.-J.1    Lee, C.O.2    Lee, K.-T.3    Choi, J.4    Park, H.-J.5
  • 26
    • 0032829501 scopus 로고    scopus 로고
    • Triterpene saponins and lignans from the roots of Pulsatilla chinensis and their cytotoxic activity against HL-60 cells
    • Mimaki Y., Kuroda M., Asano T., and Sashida Y. Triterpene saponins and lignans from the roots of Pulsatilla chinensis and their cytotoxic activity against HL-60 cells. J. Nat. Prod. 62 (1999) 1279-1283
    • (1999) J. Nat. Prod. , vol.62 , pp. 1279-1283
    • Mimaki, Y.1    Kuroda, M.2    Asano, T.3    Sashida, Y.4
  • 27
    • 0034089427 scopus 로고    scopus 로고
    • Essential moiety for antimutagenic and cytotoxic activity of hederagenin monodesmosides and bidesmosides isolated from the stem bark of Kalopanax pictus
    • Lee K.-T., Sohn I.-C., Park H.-J., Kim D.-W., Jung G.-O., and Park K.-Y. Essential moiety for antimutagenic and cytotoxic activity of hederagenin monodesmosides and bidesmosides isolated from the stem bark of Kalopanax pictus. Planta Med. 66 (2000) 329-332
    • (2000) Planta Med. , vol.66 , pp. 329-332
    • Lee, K.-T.1    Sohn, I.-C.2    Park, H.-J.3    Kim, D.-W.4    Jung, G.-O.5    Park, K.-Y.6
  • 28
    • 21344452084 scopus 로고    scopus 로고
    • Effects of α-hederin and thymoquinone, constituents of Nigella sativa, on Human cancer cell lines
    • Rooney S., and Ryan M.F. Effects of α-hederin and thymoquinone, constituents of Nigella sativa, on Human cancer cell lines. Anticancer Res. 25 (2005) 2199-2204
    • (2005) Anticancer Res. , vol.25 , pp. 2199-2204
    • Rooney, S.1    Ryan, M.F.2
  • 29
    • 0035098984 scopus 로고    scopus 로고
    • Extraction, isolation and characterisation of antitumor principle, α-hederin, from the seeds of Nigella sativa
    • Muthu Kumara S.S., and Kwong Huat B.T. Extraction, isolation and characterisation of antitumor principle, α-hederin, from the seeds of Nigella sativa. Planta Med. 67 (2001) 29-32
    • (2001) Planta Med. , vol.67 , pp. 29-32
    • Muthu Kumara, S.S.1    Kwong Huat, B.T.2
  • 30
    • 0029895874 scopus 로고    scopus 로고
    • Cytotoxicity of triterpenoid saponins. Part 1 : activities against tumor cells in vitro and hemolytical index
    • Bader G., Plohmann B., Hiller K., and Franz G. Cytotoxicity of triterpenoid saponins. Part 1 : activities against tumor cells in vitro and hemolytical index. Pharmazie 51 (1996) 414-417
    • (1996) Pharmazie , vol.51 , pp. 414-417
    • Bader, G.1    Plohmann, B.2    Hiller, K.3    Franz, G.4
  • 31
    • 2442684643 scopus 로고    scopus 로고
    • Synthesis of α-hederin, δ-hederin, and related triterpenoid saponins
    • Plé K., Chwalek M., and Voutquenne-Nazabadioko L. Synthesis of α-hederin, δ-hederin, and related triterpenoid saponins. Eur. J. Org. Chem. (2004) 1588-1603
    • (2004) Eur. J. Org. Chem. , pp. 1588-1603
    • Plé, K.1    Chwalek, M.2    Voutquenne-Nazabadioko, L.3
  • 32
    • 17044377772 scopus 로고    scopus 로고
    • Synthesis of l-arabinopyranose containing hederagenin saponins
    • Plé K., Chwalek M., and Voutquenne-Nazabadioko L. Synthesis of l-arabinopyranose containing hederagenin saponins. Tetrahedron 61 (2005) 4347-4362
    • (2005) Tetrahedron , vol.61 , pp. 4347-4362
    • Plé, K.1    Chwalek, M.2    Voutquenne-Nazabadioko, L.3
  • 33
    • 0014515315 scopus 로고
    • Interaction of saponins with cholesterol, lecithin and albumin
    • Schlösser E. Interaction of saponins with cholesterol, lecithin and albumin. Can. J. Physiol. Pharmacol. 47 (1969) 487-490
    • (1969) Can. J. Physiol. Pharmacol. , vol.47 , pp. 487-490
    • Schlösser, E.1
  • 34
    • 0025918120 scopus 로고
    • Membrane cell permeabilization with saponin and multiparametric analysis by flow cytometry
    • Jacob M.C., Favre M.J.C., and Bensa J.C. Membrane cell permeabilization with saponin and multiparametric analysis by flow cytometry. Cytometry 12 (1991) 550-558
    • (1991) Cytometry , vol.12 , pp. 550-558
    • Jacob, M.C.1    Favre, M.J.C.2    Bensa, J.C.3
  • 35
    • 0028816214 scopus 로고
    • Haemolytic time course differences between steroid and triterpenoid saponins
    • Takechi M., and Tanaka Y. Haemolytic time course differences between steroid and triterpenoid saponins. Planta Med. 61 (1995) 76-77
    • (1995) Planta Med. , vol.61 , pp. 76-77
    • Takechi, M.1    Tanaka, Y.2
  • 37
  • 38
    • 0036956250 scopus 로고    scopus 로고
    • The biological action of saponins in animal systems: a review
    • Francis G., Kerem Z., Makkar H.P.S., and Becker K. The biological action of saponins in animal systems: a review. Br. J. Nutr. 88 (2002) 587-605
    • (2002) Br. J. Nutr. , vol.88 , pp. 587-605
    • Francis, G.1    Kerem, Z.2    Makkar, H.P.S.3    Becker, K.4
  • 39
    • 0242333898 scopus 로고    scopus 로고
    • Cell-cycle-dependent three-dimensional redistribution of nuclear proteins, P120, pKi-67, and SC 35 splicing factor, in the presence of the topoisomerase I inhibitor camptothecin
    • Elias E., Lalun N., Lorenzato M., Blache L., Chelidze P., O'Donohue M.-F., Ploton D., and Bobichon H. Cell-cycle-dependent three-dimensional redistribution of nuclear proteins, P120, pKi-67, and SC 35 splicing factor, in the presence of the topoisomerase I inhibitor camptothecin. Exp. Cell Res. 291 (2003) 176-188
    • (2003) Exp. Cell Res. , vol.291 , pp. 176-188
    • Elias, E.1    Lalun, N.2    Lorenzato, M.3    Blache, L.4    Chelidze, P.5    O'Donohue, M.-F.6    Ploton, D.7    Bobichon, H.8
  • 40
    • 0035106655 scopus 로고    scopus 로고
    • Investigations of the mechanism of membrane activity of selected triterpenoid saponins
    • Melzig M.F., Bader G., and Loose R. Investigations of the mechanism of membrane activity of selected triterpenoid saponins. Planta Med. 67 (2001) 43-48
    • (2001) Planta Med. , vol.67 , pp. 43-48
    • Melzig, M.F.1    Bader, G.2    Loose, R.3
  • 41
    • 27744592640 scopus 로고    scopus 로고
    • Antitumor activity of Pulsatilla koreana saponins and their structure-activity relationship
    • Bang S.-C., Lee J.-H., Kim G.-H., Yoon M.-Y., and Ahn B.-Z. Antitumor activity of Pulsatilla koreana saponins and their structure-activity relationship. Chem. Pharm. Bull. 53 (2005) 1451-1454
    • (2005) Chem. Pharm. Bull. , vol.53 , pp. 1451-1454
    • Bang, S.-C.1    Lee, J.-H.2    Kim, G.-H.3    Yoon, M.-Y.4    Ahn, B.-Z.5
  • 42
    • 12844251367 scopus 로고    scopus 로고
    • Structure-function relationship for saponin effects on cell cycle arrest and apoptosis in the human 1547 osteosarcoma cells: a molecular modelling approach of natural molecules structurally close to diosgenin
    • Trouillas P., Corbière C., Liagre B., Duroux J.-L., and Beneytout J.-L. Structure-function relationship for saponin effects on cell cycle arrest and apoptosis in the human 1547 osteosarcoma cells: a molecular modelling approach of natural molecules structurally close to diosgenin. Bioorg. Med. Chem. 13 (2005) 1141-1149
    • (2005) Bioorg. Med. Chem. , vol.13 , pp. 1141-1149
    • Trouillas, P.1    Corbière, C.2    Liagre, B.3    Duroux, J.-L.4    Beneytout, J.-L.5
  • 43
    • 22144498387 scopus 로고    scopus 로고
    • Proapoptotic triterpene electrophiles (Avicins) form channels in membranes : cholesterol dependence
    • Li X.X., Davis B., Haridas V., Gutterman J.U., and Colombini M. Proapoptotic triterpene electrophiles (Avicins) form channels in membranes : cholesterol dependence. Biophys. J. 88 (2005) 2577-2584
    • (2005) Biophys. J. , vol.88 , pp. 2577-2584
    • Li, X.X.1    Davis, B.2    Haridas, V.3    Gutterman, J.U.4    Colombini, M.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.