title: Chemical and biological characterization of oleanane triterpenoids from soy.
abstract: Soyasaponins are a group of complex and structural diverse oleanane triterpenoids found in soy (Glycine max) and other legumes. They are primarily classified into two main groups - group A and B - based on the attachment of sugar moieties at positions C-3 and C-22 of the ring structures. Group A soyasaponins are bidesmosidic, while group B soyasaponins are monodesmosidic. Group B soyasaponins are further classified into two subcategories known as 2,3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP) and non-DDMP conjugated molecules. The preparation and purification of soyasaponin molecules is complicated by the presence of bioactive soy isoflavones, which often overlap with soyasaponin in polarity and must removed from extracts before biological assessment. Soyasaponin extracts, aglycones of group A and B and individual group B soyasaponins such as soyasaponin I have been reported to posses specific bioactive properties, such as in vitro anti-cancer properties by modulating the cell cycle and inducing apoptosis. The isolation, chemical characterization and detection strategies by HPLC and HPLC-MS are reviewed, along with the reported bioactive effects of soyasaponin extracts and individual molecules in cultured cancer cell experiments.
authors.affiliation: Department of Chemistry, National University of Singapore, Science Drive 4, 117543, Singapore.
authors.forename: Wei
authors.initials: W
authors.lastname: Zhang
authors.forename: David G
authors.initials: DG
authors.lastname: Popovich
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects; D045744:Cell Line, Tumor; D002851:Chromatography, High Pressure Liquid; D006801:Humans; D015394:Molecular Structure; D009828:Oleanolic Acid / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D012503:Saponins / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D013025:Glycine max / Q000737:chemistry*
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D012503:Saponins; D009828:Oleanolic Acid
references.citation: J Agric Food Chem. 2002 Nov 20;50(24):6951-9
references.pmid: 12428942
references.citation: J Agric Food Chem. 2009 May 13;57(9):3620-5
references.pmid: 19338335
references.citation: Curr Drug Metab. 2008 Dec;9(10):996-1009
references.pmid: 19075616
references.citation: Biosci Biotechnol Biochem. 1992 Jan;56(1):142-3
references.pmid: 1368127
references.citation: Clin Exp Metastasis. 2003;20(4):375-83
references.pmid: 12856725
references.citation: Nutr Cancer. 1997;27(2):206-9
references.pmid: 9121951
references.citation: Int J Food Sci Nutr. 2005 Nov;56(7):501-19
references.pmid: 16503561
references.citation: Exp Toxicol Pathol. 2007 Sep;59(1):35-42
references.pmid: 17582751
references.citation: J Nutr. 2005 May;135(5):1239-42
references.pmid: 15867311
references.citation: Carcinogenesis. 2006 Feb;27(2):298-306
references.pmid: 16113053
references.citation: J Agric Food Chem. 2003 Jun 4;51(12):3520-4
references.pmid: 12769517
references.citation: Nutr Cancer. 1995;23(3):259-70
references.pmid: 7603886
references.citation: J Chromatogr. 1985 May 29;325(1):275-81
references.pmid: 4040526
references.citation: Food Chem Toxicol. 2002 Dec;40(12):1767-74
references.pmid: 12419690
references.citation: J Agric Food Chem. 2005 Mar 23;53(6):1914-20
references.pmid: 15769113
references.citation: Phytochemistry. 2004 Feb;65(3):337-44
references.pmid: 14751305
references.citation: Nutr Cancer. 2003;47(1):24-33
references.pmid: 14769534
references.citation: Biochem Biophys Res Commun. 2006 Mar 10;341(2):614-9
references.pmid: 16427612
references.citation: Arch Biochem Biophys. 2002 Oct 1;406(1):1-8
references.pmid: 12234484
references.citation: J Agric Food Chem. 2004 May 5;52(9):2689-96
references.pmid: 15113177
references.citation: Carcinogenesis. 2005 Jan;26(1):159-67
references.pmid: 15471899
references.citation: Biochem Biophys Res Commun. 2001 Jun 8;284(2):466-9
references.pmid: 11394903
references.citation: J Chromatogr A. 2006 Mar 3;1108(1):31-7
references.pmid: 16448660
references.citation: Planta Med. 1996 Jun;62(3):252-5
references.pmid: 8693040
references.citation: Phytochem Anal. 2002 Nov-Dec;13(6):343-8
references.pmid: 12494753
references.citation: J Mass Spectrom. 1999 Aug;34(8):804-12
references.pmid: 10423561
references.citation: Nutr Cancer. 2001;39(1):132-8
references.pmid: 11588895
references.citation: Can J Physiol Pharmacol. 2004 Mar;82(3):183-90
references.pmid: 15052284
references.citation: Int J Cancer. 1995 Nov 15;63(4):551-9
references.pmid: 7591266
references.citation: J Agric Food Chem. 2002 Jan 30;50(3):426-30
references.pmid: 11804507
references.citation: Agric Biol Chem. 1991 Apr;55(4):911-7
references.pmid: 1368678
references.citation: Food Chem Toxicol. 1995 May;33(5):357-66
references.pmid: 7759019
references.citation: J Agric Food Chem. 2003 Mar 26;51(7):1797-800
references.pmid: 12643632
references.citation: Cancer Lett. 1993 Dec 20;75(3):143-9
references.pmid: 8313349
references.citation: J AOAC Int. 2004 Sep-Oct;87(5):1189-94
references.pmid: 15493677
references.citation: J Agric Food Chem. 2008 Apr 23;56(8):2603-8
references.pmid: 18361499
references.citation: Food Chem Toxicol. 2009 Sep;47(9):2202-8
references.pmid: 19520140
references.citation: Biosci Biotechnol Biochem. 1998 Dec;62(12):2291-9
references.pmid: 9972256
references.citation: J Agric Food Chem. 2002 Apr 24;50(9):2587-94
references.pmid: 11958627
references.citation: J Agric Food Chem. 2006 Mar 22;54(6):2035-44
references.pmid: 16536572
references.citation: J Agric Food Chem. 2003 Sep 24;51(20):5888-94
references.pmid: 13129290
references.citation: Gynecol Oncol. 2005 Feb;96(2):415-22
references.pmid: 15661230
references.citation: J Agric Food Chem. 2005 May 18;53(10):3923-30
references.pmid: 15884818
references.citation: Cell Death Differ. 2005 Nov;12 Suppl 2:1528-34
references.pmid: 16247500
references.citation: J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Feb 1;846(1-2):169-75
references.pmid: 16978933
references.citation: Int J Oncol. 2002 Jul;21(1):165-70
references.pmid: 12063564
references.citation: J Chromatogr A. 2005 Apr 29;1072(2):185-93
references.pmid: 15887487