Difference (from prior minor revision) Changed: 14c14 < These observations suggest that the soyasaponins may be an important dietary chemopreventive agent against colon cancer, after alteration by microflora.({{Gurfinkel DM, Rao AV.Soyasaponins: the relationship between chemical structure and colon anticarcinogenic activity. to > These observations suggest that the soyasaponins may be an important dietary chemopreventive agent against colon cancer, after alteration by microflora.({{Gurfinkel DM, Rao AV. Soyasaponins: the relationship between chemical structure and colon anticarcinogenic activity. Changed: 16c16 < Soyasaponins appear to be hepatoprotective. ({{Kinjo J, Hirakawa T, Tsuchihashi R, Nagao T, Okawa M, Nohara T, Okabe H.Hepatoprotective constituents in plants. 14. Effects of soyasapogenol B, sophoradiol, and their glucuronides on the cytotoxicity of tert-butyl hydroperoxide to HepG2 cells. to > Soyasaponins appear to be hepatoprotective. ({{Kinjo J, Hirakawa T, Tsuchihashi R, Nagao T, Okawa M, Nohara T, Okabe H. Hepatoprotective constituents in plants. 14. Effects of soyasapogenol B, sophoradiol, and their glucuronides on the cytotoxicity of tert-butyl hydroperoxide to HepG2 cells. Changed: 20c20 < * Medicago hispida {{Mahato SB. Triterpenoid saponins from Medicago hispida.Phytochemistry. 1991;30(10):3389-93}}(Alfalfa variant) to > * Medicago hispida {{Mahato SB. Triterpenoid saponins from Medicago hispida. Phytochemistry. 1991;30(10):3389-93}}(Alfalfa variant) Changed: 23c23 < Although soyasaponins are bioactive, there is evidence of rather limited intestinal absorption. ({{Hu J, Reddy MB, Hendrich S, Murphy PA.Soyasaponin I and sapongenol B have limited absorption by Caco-2 intestinal cells and limited bioavailability in women. J Nutr. 2004 Aug;134(8):1867-73}}) However, since they are typically found in lectin-containing legumes, and [[Lectins, induced changes in intestinal permiability|lectins induce increased gut permiability]], it could be conjectures that soyasaponin isolates may not be as easily assimilated as instead when present in the intact whole food. to > Although soyasaponins are bioactive, there is evidence of rather limited intestinal absorption. ({{Hu J, Reddy MB, Hendrich S, Murphy PA. Soyasaponin I and sapongenol B have limited absorption by Caco-2 intestinal cells and limited bioavailability in women. J Nutr. 2004 Aug;134(8):1867-73}}) However, since they are typically found in lectin-containing legumes, and [[Lectins, induced changes in intestinal permeability|lectins induce increased gut permeability]], it could be conjectures that soyasaponin isolates may not be as easily assimilated as instead when present in the intact whole food. Changed: 32c32 < * A growing number of reports demonstrate that hypersialylation, which is observed in certain pathological processes, such as oncogenic transformation, tumor metastasis, and invasion, is associated with enhanced sialyltransferase (ST) activity. There is therefore a need for the development of ST inhibitors to modulate ST activity and thus alleviate the disease processes caused by STs. In the present study, soyasaponin I had been discovered to be a potent and specific ST inhibitor by screening strategy from 7500 samples including micribial extracts and natural products. Kinetic analysis shows that it is a CMP-Neu5Ac competitive inhibitor with for ST3Gal I with an inhibition constant (K(i)) of 2.1 microM. In addition, it is only active against ST, but not against the other tested glycosyltransferases and glycosidases. Our study is the first report to discover ST inhibitor by screening method and also to provide the new chemical structure information that should be useful in the development of other novel ST inhibitors to > * A growing number of reports demonstrate that hypersialylation, which is observed in certain pathological processes, such as oncogenic transformation, tumor metastasis, and invasion, is associated with enhanced sialyltransferase (ST) activity. There is therefore a need for the development of ST inhibitors to modulate ST activity and thus alleviate the disease processes caused by STs. In the present study, soyasaponin I had been discovered to be a potent and specific ST inhibitor by screening strategy from 7500 samples including microbial extracts and natural products. Kinetic analysis shows that it is a CMP-Neu5Ac competitive inhibitor with for ST3Gal I with an inhibition constant (K(i)) of 2.1 microM. In addition, it is only active against ST, but not against the other tested glycosyltransferases and glycosidases. Our study is the first report to discover ST inhibitor by screening method and also to provide the new chemical structure information that should be useful in the development of other novel ST inhibitors Changed: 42c42 < * OBJECTIVE: Sialylation involving tumor formation and invasive behavior goes along with altered sialyltransferase (ST) activity. A potent ST inhibitor, soyasaponin I (SsaI), was discovered to selectively inhibit the cellular alpha2,3-sialyltranserase activity. In this study, we further test the effects of SsaI on modifying the metastatic and invasive behaviors of cancer cell lines. METHODS: Nonmetastatic breast cancer cell line, MCF-7, and highly metastastic breast cancer cell line, MDA-MB-231, were used to investigate the effects of SsaI on tumor cells. RESULTS: SsaI did not affect cell growth cycle and also failed to inhibit cell growth in this study (the concentration of SsaI < or=100 muM). SsaI was as predicted to successfully inhibit cellular alpha2,3-ST activity and depressed the dose-dependent tumor cell surface alpha2,3-sialic acid expression. In addition, different concentrations of SsaI did stimulate MCF-7 cell adhesion to collagen type I linearly and significantly enhanced cell adhesion to the Matrigel-matrix. Furthermore, SsaI significantly decreased MDA-MB-231 cell migration. Reverse transcriptase polymerase chain reaction for evaluating mRNA expression of ST3Gal I, III and IV showed that SsaI also down-regulated the expression of ST3Gal IV but did not affect the other two. CONCLUSIONS: The results showed that SsaI was implicated in the invasive behavior of tumor cells, suggesting that altered alpha2,3-sialylation pathway played a crucial role in the adhesion and tumor metastases. SsaI is a good candidate for studying the biological roles of ST, and might provide a new preventive strategy in tumor metastasis. to > * OBJECTIVE: Sialylation involving tumor formation and invasive behavior goes along with altered sialyltransferase (ST) activity. A potent ST inhibitor, soyasaponin I (SsaI), was discovered to selectively inhibit the cellular alpha2,3-sialyltranserase activity. In this study, we further test the effects of SsaI on modifying the metastatic and invasive behaviors of cancer cell lines. METHODS: Nonmetastatic breast cancer cell line, MCF-7, and highly metastatic breast cancer cell line, MDA-MB-231, were used to investigate the effects of SsaI on tumor cells. RESULTS: SsaI did not affect cell growth cycle and also failed to inhibit cell growth in this study (the concentration of SsaI < or=100 muM). SsaI was as predicted to successfully inhibit cellular alpha2,3-ST activity and depressed the dose-dependent tumor cell surface alpha2,3-sialic acid expression. In addition, different concentrations of SsaI did stimulate MCF-7 cell adhesion to collagen type I linearly and significantly enhanced cell adhesion to the Matrigel-matrix. Furthermore, SsaI significantly decreased MDA-MB-231 cell migration. Reverse transcriptase polymerase chain reaction for evaluating mRNA expression of ST3Gal I, III and IV showed that SsaI also down-regulated the expression of ST3Gal IV but did not affect the other two. CONCLUSIONS: The results showed that SsaI was implicated in the invasive behavior of tumor cells, suggesting that altered alpha2,3-sialylation pathway played a crucial role in the adhesion and tumor metastases. SsaI is a good candidate for studying the biological roles of ST, and might provide a new preventive strategy in tumor metastasis. C O N T E N T S
See Also
DescriptionSoyasaponins are bioactive compounds found in many legumes. Results from in vitro fermentation suggested that colonic microflora readily hydrolyzed the soyasaponins to [Aglycone? aglycones]. DiscussionSoyasaponins appear to be significant inhibitors of sialyltransferase, which may indicate a significant role in cancer chemotherapeutics and prevention. These observations suggest that the soyasaponins may be an important dietary chemopreventive agent against colon cancer, after alteration by microflora.(1) Soyasaponins appear to be hepatoprotective. (2, 3 ) Although soyasaponins are bioactive, there is evidence of rather limited intestinal absorption. (6) However, since they are typically found in lectin-containing legumes, and [Lectins, induced changes in intestinal permeability? lectins induce increased gut permeability], it could be conjectures that soyasaponin isolates may not be as easily assimilated as instead when present in the intact whole food. AbstractsSoyasaponin I, a potent and specific sialyltransferase inhibitorBiochem Biophys Res Commun. 2001 Jun 8;284(2):466-9. Wu CY, Hsu CC, Chen ST, Tsai YC. Institute of Biochemistry, National Yang-Ming University, Taipei, Taiwan.
Human fecal metabolism of soyasaponin IJ Agric Food Chem. 2004 May 5;52(9):2689-96. Hu J, Zheng YL, Hyde W, Hendrich S, Murphy PA. Department of Food Science and Human Nutrition, and College of Veterinary Medicine, Iowa State University, 2312 Food Science Building, Ames, Iowa 50011, USA.
Soyasaponin-I-modified invasive behavior of cancer by changing cell surface sialic acidsGynecol Oncol. 2005 Feb;96(2):415-22. Hsu CC, Lin TW, Chang WW, Wu CY, Lo WH, Wang PH, Tsai YC. Institute of Biochemistry, National Yang-Ming University, Taipei, Taiwan.
Soyasaponin I decreases the expression of alpha2,3-linked sialic acid on the cell surface and suppresses the metastatic potential of B16F10 melanoma cellsBiochem Biophys Res Commun. 2006 Mar 10;341(2):614-9. Epub 2006 Jan 13. Chang WW, Yu CY, Lin TW, Wang PH, Tsai YC. Institute of Biochemistry and Molecular Biology, National Yang-Ming University, Taipei, Taiwan, ROC.
References1. Gurfinkel DM, Rao AV. Soyasaponins: the relationship between chemical structure and colon anticarcinogenic activity. Nutr Cancer. 2003;47(1):24-33. 2. Kinjo J, Hirakawa T, Tsuchihashi R, Nagao T, Okawa M, Nohara T, Okabe H. Hepatoprotective constituents in plants. 14. Effects of soyasapogenol B, sophoradiol, and their glucuronides on the cytotoxicity of tert-butyl hydroperoxide to HepG2 cells. Biol Pharm Bull. 2003 Sep;26(9):1357-60 3. Kinjo J, Imagire M, Udayama M, Arao T, Nohara T. Structure-hepatoprotective relationships study of soyasaponins I-IV having soyasapogenol B as aglycone. Planta Med. 1998 Apr;64(3):233-6 4. Mahato SB. Triterpenoid saponins from Medicago hispida. Phytochemistry. 1991;30(10):3389-93 5. Oleszek W, Stochmal A. Triterpene saponins and flavonoids in the seeds of Trifolium species. Phytochemistry. 2002 Sep;61(2):165-70 6. Hu J, Reddy MB, Hendrich S, Murphy PA. Soyasaponin I and sapongenol B have limited absorption by Caco-2 intestinal cells and limited bioavailability in women. J Nutr. 2004 Aug;134(8):1867-73 |
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