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Structure type: oligomer
Trivial name: soyasaponin I, astrachrysoside A soyasaponin I, soyasaponin 1, saponin Bb soyasaponin I, soyasaponin Bb
Compound class: saponin glycoside, glycoside, triterpenoid glycoside
Contained glycoepitopes: IEDB_115136,IEDB_136044,IEDB_136105,IEDB_137472,IEDB_140630,IEDB_141794,IEDB_190606,IEDB_225177,IEDB_423153,IEDB_885823,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88

• Article ID: 9733
  Kitagawa I, Taniyama T, Nagahama Y, Okubo K, Yamauchi F, Yoshikawa M "Saponin and sapogenol. XLII. Structures of acetyl-soyasaponins A1, A2, and A3, astringent partially acetylated bisdesmosides of soyasapogenol A, from American soybean, the seeds of Glycine max Merrill" - Chemical and Pharmaceutical Bulletin 36(8) (1988) 2819-2828
  

  By means of high performance liquid chromatography and other methods, three new partially acetylated soyasaponins, named acetyl-soyasaponin A1 (6a), acetyl-soyasaponin A2 (7a), and acetyl-soyasaponin A3 (8a), were isolated from American soybeans, the seeds of Glycine max MERRILL., together with hitherto known soyasaponins I (3), II (4), and III (5). Acetyl-soyasaponins A1,A2,and A3 are noteworthy due to their bitter and astringent tastes, although their parent saponins, soyasaponins A1 (6), A2 (7), and A3 (8), do not show such tastes.By virtue of the photochemical degradation method for the glucuronide linkage and on the basis of 1H- and 13C-nuclear magnetic resonance and secondary ion mass spectrum analyses, structures of acetyl-soyasaponins A1,A2,and A3 have been elucidated as 3-O-[β-D-glucopyranosyl-(1→2)-β-D-galactopyranosyl(1→2)-β-D-glucuronopyranosyl]-22-O-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl(1→3)-α-L-arabinopyranosyl]soyasapogenol A (6a), 3-O-[β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl]-22-O-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl(1→3)-α-L-arabinopyranosyl]soyasapogenol A (7a), and 3-O-[α-L-arabinopyranosyl-(1→2)-β-D-glucuronopy-ranosyl]-22-O-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl(1→3)-α-L-arabinopyranosyl]soyasapogenol A (8a), respectively.

  soybean, Glycine max, acetyl-soyasaponin A2, acetyl-soyasaponin A3, soyasaponin A3, oligoglycoside SIMS, oligoglycoside 13C NMR, glucuronide photolysis

  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003627155
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Osaka University, Japan, Faculty of Agriculture, Tohoku University, Japan
  Methods: 13C NMR, 1H NMR, gel filtration, IR, methanolysis, HPLC, alkaline hydrolysis, methylation analysis, CLC, photolysis
  
   
  
  Glycine max
  CSDB ID 119472 (all data & tools)
• Article ID: 9754
  Kitagawa I, Yoshikawa M, Yosioka I "Structures of three soybean saponins. Soyasaponin I, II, and III" - Chemical and Pharmaceutical Bulletin 22(12) (1974) 3010-3013
  
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Methods: IR, acid hydrolysis, methylation analysis, PMR
  
   
  
  Glycine max
  CSDB ID 118897 (all data & tools)
• Article ID: 9757
  Kitagawa I, Yoshikawa M, Yosioka I "Saponin and sapogenol. XIII. Structures of three soybean saponins: soyasaponin I, soyasaponin II, and soyasaponin III" - Chemical and Pharmaceutical Bulletin 24(1) (1976) 121-129
  

  Soyasaponin I (major), II and III, all of which possess soyasapogenol B (2) as the common aglycone, have been isolated from the MeOH extractive of soybean (Glycine max MERRILL, Leguminosae). On the basis of chemical and physicochemical evidence, the structure of soyasaponin I has been elucidated to be 3-O-[α-L-rhamnopyranosyl(1→2)-β-D-galactopyranosyl(1→2)-β-D-glucuronopyranosyl]-soyasapogenol B (7) and the structures of soyasaponin II and III to be 3-O-[α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranosyl(1→2)-β-D-glucuronopyranosyl]-soyasapogenol B (8) and 3-O-[β-D-galactopyranosyl(1→2)-β-D-glucuronopyranosyl]-soyasapogenol B (9), respectively.

  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003634810
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Osaka University, Japan
  Methods: IR, TLC, acid hydrolysis, methanolysis, methylation analysis, PMR
  
   
  
  Glycine max
  CSDB ID 118915 (all data & tools)
• Article ID: 9843
  Yoshikawa M, Komatsu H, Sakurama T, Nishida N, Yamahara J, Shimada H, Matsuda H, Tani T "Medicinal Foodstuffs. VI. Histamine release inhibitors from kidney bean, the seed of Phaseolus vulgaris L.: Chemical structures of sandosaponins A and B" - Chemical and Pharmaceutical Bulletin 45(5) (1997) 877-882
  

  Two new olean-12-ene-type triterpene oligoglycosides, named sandosaponins A and B, were isolated from kidney bean, the seed of Phaseolus vulgaris L., together with three known saponins, soyasaponins I and V and dehydrosoyasaponin 1. The structures of sandosaponins A and B were determined on the basis of chemical and physicochemical evidence, which included the chemical derivation of sandosapogenol from a known sapogenol, soyasapogenol B. Five saponins obtained from kidney bean were found to inhibit histamine release from rat exudate cells induced by an antigen-antibody reaction and, among them, sandosaponins A and B showed the most potent inhibitory activity.

  sandosaponin, Phaseolus vulgaris, kidney bean, histamine release inhibitor, medicinal foodstuff, antiallergic glycoside

  NCBI PubMed ID: 9178523
  Publication DOI: 10.1248/cpb.45.877
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Kyoto Pharmaceutical University, Kyoto, Japan, Research Laboratories for High Quality of Life, Kyoto, Japan
  Methods: 13C NMR, 1H NMR, TLC, HPLC, enzymatic digestion, bioassays
  
   
  
  Phaseolus vulgaris
  CSDB ID 270796 (all data & tools)
• Article ID: 9976
  Shiraiwa M, Kudo S, Shimoyamada M, Harada K, Okubo K "Composition and structure of 'group A saponin' in soybean seed" - Agricultural and Biological Chemistry 55 (1991) 315-322
  

  The composition of "group A saponin" in the seed hypocotyl of soybean was analyzed, and six kinds of "group A saponins," named Aa, Ab, Ac, Ad, Ae and Af according to their elution order from HPLC, were detected. On the basis of chemical and physicochemical evidence, Aa, Ab, Ae and Af are shown to be identical with the known saponins, acetyl-soyasaponins A_4, A_1, A_5 and A_2, respectively, whilst Ac and Ad were novel saponins possessing different sugar chains. In all these saponins, the terminal sugar of the oligosaccharide chain attached to C-22 of an aglycone (soyasapogenol A) was acetvlated in the soybean seed.

  Journal NLM ID: 0370452
  WWW link: http://ci.nii.ac.jp/lognavi?name=nels&lang=en&type=pdf&id=ART0008332881
  Publisher: Tokyo: Agricultural Chemical Society Of Japan
  Institutions: Department of Food Chemistry, Facultv of Agriculture, Tohoku University, Japan, National Institute of Agrobiological Resources, Ministry of Agriculture, Forestry and Fisheries, Japan
  Methods: 13C NMR, gel filtration, IR, TLC, acid hydrolysis, MS, HPLC
  
   
  
  Glycine max
  CSDB ID 101396 (all data & tools)
• Article ID: 10062
  Ireland PA, Dziedzic SZ "Saponins and sapogenins of chickpea, haricot bean and red kidney bean" - Food Chemistry 23 (1987) 105-116
  

  The saponins of red kidney bean (Phaseolus vulgaris), chick pea (Cicer arientinum) and haricot bean (Phaseolus vulgaris) all contain soyasapogenol B as the only aglycone. The levels of soyasapogenol B estimated were: chick pea, 0·075%; haricot bean, 0·149%; and red kidney bean, 0·102%; on a defatted, dry weight basis. HPLC separation of the saponin preparations indicates the presence of at least five saponins in red kidney bean, five in haricot bean and two in chick pea. Retention time comparison of the saponin preparations indicates the possible presence of soyasaponin I in all three legumes and soyasaponin II in haricot and red kidney beans.

  Journal NLM ID: 7702639
  WWW link: 10.1016/0308-8146(87)90004-5
  Publisher: Elsevier Applied Science Publishers
  Institutions: Department of Food Science, Food Studies Building, University of Reading, Reading, Great Britain
  
   
  
  Cicer arietinum, Phaseolus vulgaris
  CSDB ID 126102 (all data & tools)
• Article ID: 10130
  Rao GV, Rao PS, Tomimori T, Kizu H "Soyasaponin-I from the roots of Arachis hypogaea" - Planta Medica 51 (1985) 71-72
  
  NCBI PubMed ID: 17340410
  Publication DOI: 10.1055/s-2007-969400
  Journal NLM ID: 0066751
  Publisher: George Thieme
  Institutions: Department of Chemistry, Kakatiya University, Warangal 506 009, India
  
   
  
  Arachis hypogaea
  CSDB ID 147207 (all data & tools)
• Article ID: 10161
  Shimoyamada M, Kudo S, Okubo K, Yamauchi F, Harada K "Distributions of saponin constituents in some varieties of soybean plant" - Agricultural and Biological Chemistry 54 (1990) 77-81
  

  Saponins are bioactive substances with physiological activities and bitter taste. We investigated the distributions of saponins in soybean plants. Acetyl-soyasaponins A_1 and A_4 occur only in seed hypocotyls of soybean plants. Soyasaponin I was detected in all organs of the plant. However, soyasaponin I levels in plant showed very heterogenous distributions, for example, stem and main root had very low soyasaponin I levels, but nodule and leaf had higher levels.

  Journal NLM ID: 0370452
  WWW link: http://ci.nii.ac.jp/naid/110006324552
  Publisher: Tokyo: Agricultural Chemical Society Of Japan
  Institutions: Tohoku University, Department of Food Chemistry, Faculty of Agriculture, Japan, Kanesa Miso Ltd., Japan, National Institute of Agrobiological Resources, Japan
  Methods: gel filtration, TLC, HPLC
  
   
  
  Glycine max
  CSDB ID 101312 (all data & tools)
• Article ID: 10169
  Shiraiwa M, Harada K, Okubo K "Composition and content of saponins in soybean seed according to variety, cultivation year and maturity" - Agricultural and Biological Chemistry 55 (1991) 323-331
  

  There was a remarkable varietal difference in regard to the composition of "group A saponin" in seed hypocotyls of 457 varieties of soybeans. It was observed that the saponin composition in soybean seed was not affected by the difference in the year of cultivation of the seed, but was peculiar to the variety. The content of total saponin in the seed hypocotyl fraction of soybean ranged from 0.62-6.16%. The content of saponin in soybean seed was more greatly dependant on the variety than on the cultivatation year. In soybean seeds harvested at different degrees of maturity, the saponin content varied with the maturity of seed, although the nature of this variation was insufficient to exert an influence upon the varietal difference.

  Journal NLM ID: 0370452
  WWW link: http://ci.nii.ac.jp/naid/110006325358
  Publisher: Tokyo: Agricultural Chemical Society Of Japan
  Institutions: National Institute of Agrobiological Resources, Ministry of Agriculture, Forestry and Fisheries, Japan, Department of Food Chemistry, Faculty of Agriculture, Tohoku University, Japan
  Methods: TLC, HPLC
  
   
  
  Glycine max
  CSDB ID 101409 (all data & tools)
• Article ID: 10170
  Shimoyamada M, Okubo K "Variation in saponin contents in germinating soybean seeds and effect of light irradiation" - Agricultural and Biological Chemistry 55 (1991) 577-579
  
  Journal NLM ID: 0370452
  WWW link: http://ci.nii.ac.jp/naid/110006325394
  Publisher: Tokyo: Agricultural Chemical Society Of Japan
  Institutions: Department of Food Chemistry, Faculty of Agriculture, Tohoku University, Japan
  Methods: HPLC
  
   
  
  Glycine max
  CSDB ID 101414 (all data & tools)
• Article ID: 10171
  Shiraiwa M, Harada K, Okubo K "Composition and structure of 'Group B saponin' in soybean seed" - Agricultural and Biological Chemistry 55 (1991) 911-917
  

  The composition of "group B saponin" in soybean seed was analyzed by HPLC, and six kinds of "group B saponin," named Ba, Bb, Bb', Bc, Bd and Be according to elution order from HPLC, were detected. Of these saponins, Ba, Bb, Bb' and Bc were identified with soyasaponin V, I, III and II, respectively. Bd and Be were novel saponins possessing soyasapogenol E as the aglycone and the same sugar chain as Ba and Bb, respectively. These saponins were very unstable in the isolated state and had a tendency to form Ba and Bb, respectively. From these results, Bd and Be are presumed to be the precursors of Ba and Bb in soybean seed.

  NCBI PubMed ID: 1368678
  Journal NLM ID: 0370452
  WWW link: http://ci.nii.ac.jp/naid/110006325468
  Publisher: Tokyo: Agricultural Chemical Society Of Japan
  Institutions: National Institute of Agrobiological Resources, Ministry of Agriculture, Forestry and Fisheries, Japan, Department of Food Chemistry, Faculty of Agriculture, Tohoku University, Miyagi, Japan
  Methods: 13C NMR, EI-MS, IR, TLC, acid hydrolysis, HPLC
  
   
  
  Glycine max
  CSDB ID 101418 (all data & tools)
• Article ID: 10172
  Shimoyamada M, Harada K, Okubo K "Saponin composition in developing soybean seed (Glycine max (L.) Merrill, cv. Mikuriyaao)" - Agricultural and Biological Chemistry 55 (1991) 1403-1405
  
  Journal NLM ID: 0370452
  WWW link: http://ci.nii.ac.jp/naid/110006325555
  Publisher: Tokyo: Agricultural Chemical Society Of Japan
  Institutions: National Institute of Agrobiological Resources, Japan, Department of Food Chemistry, Faculty of Agriculture, Tohoku University, Japan
  Methods: biological assays, HPLC
  
   
  
  Glycine max
  CSDB ID 101428 (all data & tools)
• Article ID: 10252
  Oleszek W, Jurzysta M, Price KR, Fenwick GR "High-performance liquid chromatography of alfalfa root saponins" - Journal of Chromatography 519 (1990) 109-116
  

  A method for the separation of individual saponins present in alfalfa roots using high-performance liquid chromatography is described. The derivatized saponins are monitored using UV detection and the potential of the method for the quantitation of intact saponins in plant extracts is discussed.

  Publication DOI: 10.1016/0021-9673(90)85139-M
  Journal NLM ID: 0427043
  Publisher: Amsterdam: Elsevier
  Institutions: AFRC Institute of Food Research, Norwich, UK, Department of Biochemistry, Institute of Soil Science and Plant Cultivation, Pulawy, Poland
  Methods: HPLC
  
   
  
  Medicago sativa
  CSDB ID 138949 (all data & tools)
• Article ID: 10295
  Hayashi H, Sakai T, Fukui H, Tabata K "Formation of soyasaponins in licorice cell suspension cultures" - Phytochemistry 29 (1990) 3127-3129
  

  Cell suspension cultures of licorice (Glycyrrhiza glabra) have been shown to produce soyasaponins I and II, oleanane-type triterpene glycosides, which are known to exist in certain leguminous plants. The soyasaponin content in the licorice cell cultures varied from 0.017 to 1.1% of the dry weight of cells depending on culture strains and were also greatly influenced by plant growth hormones.

  plant cell culture, Leguminosae, triterpenoid saponin, Glycyrrhiza glabra, soyasapogenol B, soyasaponin I, soyasaponin II

  Publication DOI: 10.1016/0031-9422(90)80170-L
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: Faculty of Pharmaceutical Sciences, Kyoto University, Yoshida, Kyoto, Japan
  
   
  
  Glycyrrhiza glabra
  CSDB ID 145622 (all data & tools)
• Article ID: 10321
  Wang HK, He K, Xu HX, Zhang ZL, Wang YF, Kikuchi T, Tezuka Y "The structure of astrachrysosid A and the study of 2D-NMR on astrasieversianin XV and 7,2'-dihydroxy-3',4'-dimethoxy-isoflavane-7-O-β-D-glycoside" - Yao xue xue bao = Acta pharmaceutica Sinica [Chinese] 25 (1990) 445-450
  

  Six compounds were isolated from the root of Astragalus chrysopterus Bunge. One of them was identified as a new triterpenoid glycoside, named astrachrysoside A. Its structure was elucidated as 3-O-[α-L-rhamnopyranosyl (1----2) β-D-xylopyranosyl]-cycloastragenol on the basis of physicochemical evidence and chemical reactions. The others were shown to be known compounds, astrasieversianin XV (II), 7,2'-dihydroxy-3',4'-dimethoxy-isoflavane-7-O-β-D-glucoside (III), soyasaponin I, daucosterol and β-sitosterol. Full assignment of the chemical shift signals of II and III were established by various 2D-NMR techniques.

  NCBI PubMed ID: 2284972
  Journal NLM ID: 21710340R
  Publisher: Beijing: Zhongguo yao xue hui
  Institutions: Shanghai College of Traditional Chinese Medicine
  
   
  
  Astragalus chrysopterus
  CSDB ID 149859 (all data & tools)
• Article ID: 10388
  Kitagawa I, Saito M, Taniyama T, Yoshikawa M "Saponin and sapogenol. XXXIX. Structure of soyasaponin A1, a bisdesmoside of soyasapogenol A, from soybean, the seeds of Glycine max Merrill" - Chemical and Pharmaceutical Bulletin 33 (1985) 1069-1076
  

  Five bioactive triterpene-oligoglycosides, named soyasaponins I, II, III, A_1 (3), and A_2 (2), were isolated from soybean, the seeds of Glycine max MERRILL (Leguminosae). By employing a photochemical degradation method and a lead tetraacetate degradation method, which are two of four selective cleavage methods available for the glucuronide linkage in oligoglycosides, the structure of soyasaponin A_1 was elucidated to be 3-O [β-D-glucopyranosyl(1→2)-β-D-galactopyranosyl(1→2)-β-D-glucuronopyranosyl-22-O-[β-D-glucopyranosyl(1→3)-α-L-arabinopyranosyl]-soyasapogenol A (3).

  soybean, Glycine max, soyasaponin A1, oleanene-bisdesmoside, glukuronide linkage selective cleavage, glukuronide linkage photolysis, glukuronide linkage lead tetraacetate degradation, oleanene-bisdesmoside 13C NMR, triterpene-oligoglycoside biological activity

  Publication DOI: 10.1248/cpb.33.1069
  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003625485
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Osaka University, Japan
  Methods: 13C NMR, IR, acid hydrolysis, methanolysis, alkaline hydrolysis, enzymatic digestion, methylation analysis, reduction, photolysis, lead tetraacetate oxidation
  
   
  
  Glycine max
  CSDB ID 119283 (all data & tools)
• Article ID: 10393
  Taniyama T, Nagahama Y, Yoshikawa M, Kitagawa I "Saponin and sapogenol. XLIII. Acetyl-soyasaponins A4, A5, and A6, new astringent bisdesmosides of soyasapogenol A, from Japanese soybean, the seeds of Glycine max Merrill" - Chemical and Pharmaceutical Bulletin 36 (1988) 2829-2839
  

  In addition to soyasaponins I, II, and III, three new bitter and astringent bisdesmosides named acetyl-soyasaponin A_4(2), acetyl-soyasaponin A_5 (3), and acetyl-soyasaponin A_6 (4) which are characterized by having a fully acetylated terminal xylosyl moiety, have been isolated from a Japanese species of soybean (Tamanishiki strain), the seeds of Glycine max MERRILL, cultivated in Hokkaido Prefecture. By means of photochemical degradation (a selective cleavage method for the glucuronide linkage), and on the basis of physicochemical evidence including ^1H- and ^<13>C-nuclear magnetic resonance analysis, the structures of acetyl-soyasaponins A_4,A_5,and A_6 have been elucidated as 3-O-[β-D-glucopyranosyl(1→2)-β-D-galactopyranosyl(1→2)-β-D-glucuronopyranosyl]-22-O-[2,3,4-tri-O-acetyl-β-D-xylopyranosyl(1→3)-α-L-arabinopyranosyl]soyasapogenol A (2), 3-O-[β-D-galactopyranosyl(1→2)-β-D-glucuronopyranosyl]-22-O-[2,3,4-tri-O-acetyl-β-D-xylopyranosyl(1→3)-α-L-arabinopyranosyl]soyasapogenol A (3), and 3-O-[α-L-arabinopyranosyl-(1→2)-β-D-glucuronopyranosyl]-22-O-[2,3,4-tri-O-acetyl-β-D-xylopyranosyl(1→3)-α-L-arabinopyranosyl]soyasapogenol A (4), respectively.

  soybean, Glycine max, oligoglycoside 13C NMR, glucuronide photolysis, acetyl-soyasaponin A4, acetyl-soyasaponin A5, acetyl-soyasaponin A6, soyasaponin A4, soyasaponin A5, soyasaponin A6

  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003627156
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Osaka University, Osaka, japan
  Methods: 13C NMR, 1H NMR, gel filtration, IR, FAB-MS, methanolysis, alkaline hydrolysis, methylation analysis, reduction, photolysis
  
   
  
  Glycine max
  CSDB ID 119486 (all data & tools)
• Article ID: 10525
  Hayashi H, Fukui H, Tabata M "Distribution pattern of saponins in different organs of Glycyrrhiza glabra" - Planta Medica 59 (1993) 351-353
  

  Soyasaponins were detected by GC and GC-MS in different organs of GLYCYRRHIZA GLABRA, particularly in the seed, hypocotyl and rootlet, whereas glycyrrhizin was detected exclusively in the thickening root and the stolon. An inverse relationship was found between the soyasaponins content and the glycyrrhizin content in the growing stolon and in the roots at different stages of growth.

  distribution, glycyrrhizin, saponin, Glycyrrhiza glabra, soyasapogenol B, soyasaponins, 18β-glycyrrhetinic acid

  NCBI PubMed ID: 17235989
  Publication DOI: 10.1055/s-2006-959699
  Journal NLM ID: 0066751
  Publisher: George Thieme
  Institutions: Faculty of Pharmaceutical Sciences, Kyoto University, Yoshida, Kyoto, Japan, Faculty of Pharmaceutical Sciences, Kyoto University, Yoshida, Kyoto 606, Japan
  
   
  
  Glycyrrhiza glabra
  CSDB ID 147285 (all data & tools)
• Article ID: 10637
  Tsukamoto C, Kikuchi A, Harada K, Kitamura K, Okubo K "Genetic and chemical polymorphisms of saponins in soybean seed" - Phytochemistry 34 (1993) 1351-1356
  

  The variation in saponin composition in soybean seeds is explained by different combinations of five genes controlling the utilization of soyasapogenol glycosides as substrates. The function of these genes is variety-specific and organ-specific. Phenotypes of over 1000 soybeans were classified into eight saponin types, and the frequency of phenotypes was different between the cultivated [Glycine max (L.) Merr.] and the wild soybean (G. soja Sieb. & Zucc.). The AaBc saponin type predominated in G. soja (58.4% of test collections), but was only found in 0.3% of G. max. Four unidentified arabinoside saponins were detected in the seeds of the AaBc type soybeans. The mode of inheritance of saponin types is explained by a combination of co-dominant, dominant and recessive acting genes. The combined chemical and genetic data show that the directed manipulation of soybean saponin composition is a possibility for the future.

  chemical structure, gene expression, triterpenoids, Glycine max, Leguminosae, Glycine soja, sugar chain composition, inheritance

  NCBI PubMed ID: 7764284
  Publication DOI: 10.1016/0031-9422(91)80028-Y
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: Department of Applied Biological Chemistry, Faculty of Agriculture, Tohoku University, Miyagi, Japan, Tohoku National Agricultural Experiment Station, MAFF, Kariwano, Akita, Japan, National Institute of Agrobiological Resources, MAFF, Tsukuba, Japan, National Agriculture Research Center, MAFF, Tsukuba, Japan
  Methods: FAB-MS, TLC, acid hydrolysis, HPLC
  
   
  
  Glycine max, Glycine soja
  CSDB ID 146150 (all data & tools)
• Article ID: 10776
  Oleszek W, Jurzysta M, Ploszynski M, Colquhoun IJ, Price KR, Fenwick GR "Zahnic acid tridesmoside and other dominant saponins from alfalfa (Medicago sativa L.) aerial parts" - Journal of Agricultural and Food Chemistry 40 (1992) 191-196
  

  A zahnic acid tridesmoside, 3-0-[β-D-glucopyranosyl(1-2)-β-D-glucopyranosyl-(1-2)-β-D-glucopyranosyl]-2β,3β,16α-trihydroxyolean-12-ene-23,28-dioic acid-23-O-α-L-arabinopyranosyl-28-O-[β-D-apiofuranosyl-(l-3)-β-D-xylopyranosyl(l-4)-α-L-rhamnopyranosyl(l-2)-α-L-arabinoside], has been identified as the main saponin present in the aerial parts of alfalfa by a combination of chromatographic, chemical, and spectroscopic techniques. Moreover, four medicagenic acid glycosides and soyasaponin I have been isolated from the same source and identified. Three of the medicagenic acid glycosides are identical to those previously found in alfalfa roots, while the fourth has been identified as 2-β-hydroxy-3-β-O-glucuronopyranosyl 28-O-[α-L-rhamnopyranosyl(1-2)-α-L-arabinopyranoside]olean-12-en-23-oic acid. Biological activity was measured using the fungus Trichoderma viride, and hemolytic activity was assessed using a hemolytic test. The zahnic acid glycoside did not inhibit fungal growth over a wide range of concentrations and exhibited only weak hemolytic activity.

  Publication DOI: 10.1021/jf00014a005
  Journal NLM ID: 0374755
  Publisher: American Chemical Society
  Methods: 13C NMR, FAB-MS, GC-MS, TLC, acid hydrolysis, GC, HPLC, alkaline hydrolysis, biological assay, LC, HRPLC
  
   
  
  Medicago sativa
  CSDB ID 131263 (all data & tools)
• Article ID: 10851
  Kinjo J, Kishida F, Watanabe K, Hashimoto F, Nohara T "Five new triterpene glycosides from Russell lupine" - Chemical and Pharmaceutical Bulletin 42 (1994) 1874-1878
  

  In a continuing study on the ingredients of Lupinus genus, we examined the oligoglycoside constituents of the Russell lupine (L. polyphyllus×L. arboreus hybrid). Five new oleanene glycosides, called Lupinosides PA_<1-5> (1-5), together with three known ones were isolated. Their structures of 1-5 were determined to be 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glactopyranosyl-(1→2)-β-D-glucuronopyranosyl soyasapogenol A 21-O-β-D-xylopyranoside (1), 3-O-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl soyasapogenol A 21-O-β-D-xylopyranoside (2), 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl kudzusapogenol A 21-O-β-D-xylopyranoside (3), 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl soyasapogenol B 22-O-α-L-rhamnopyranoside (4), and 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl soyasapogenol B 22-O-β-D-glucopyranosyl-(1→4)-α-L-rhamnopyranoside (5), respectively.

  Leguminosae, oleanene glycoside, lupinoside, Russell lupine, Lupinus polyphyllus x L. arboreus

  NCBI PubMed ID: 7954941
  Publication DOI: 10.1248/cpb.42.1874
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Kumamoto University, Japan
  Methods: 13C NMR, 1H NMR, EI-MS, IR, FAB-MS, TLC, acid hydrolysis, HPLC, enzymatic digestion, CC
  
   
  
  Lupinus polyphyllus * Lupinus arboreus
  CSDB ID 220470 (all data & tools)
• Article ID: 10873
  Nishida K, Ohta Y, Araki Y, Ito M, Nagamura Y, Ishiguro I "Inhibitory effects of 'group A saponin' and 'group B saponin' fractions from soybean seed hypocotyls on radical-initiated lipid peroxidation in mouse liver microsomes" - Journal of Clinical Biochemistry and Nutrition 15 (1993) 175-184
  

  We examined the inhibitory effects of "group A saponin" and "group B saponin" fractions, which were extracted and separated from soybean seed hypocotyls, on water-soluble 2,2'-azobis(2-amidino-propane) (AAPH)- and lipid-soluble 2,2'-azobis(2,4-dimethylvaleronitrile) (AMVN)-initiated lipid peroxidation reactions that were conducted with mouse liver microsomes. The simultaneous addition of the group A saponin fraction dose-dependently inhibited AAPH- or AMVN-initiated lipid peroxidation in microsomes more strongly than that of the group B saponin fraction. The group A saponin fraction inhibited the AAPH-initiated lipid peroxidation with a lag, phase, while it immediately blocked the AMVN-initiated lipid peroxidation. The group A saponin fraction inhibited microsomal AAPH-initiated lipid peroxidation even when added to the reaction mixture after the lag phase period. Microsomes pretreated with the group A saponin fraction showed inhibition of AAPH-initiated lipid peroxidation with a prolonged lag phase, and the saponin fraction-pretreated microsomes showed inhibition of the AMVN-initiated lipid peroxidation in which a lag phase was found. These results indicate that in mouse liver microsomes, the group A saponin fraction from soybean seed hypocotyls, which is present outside and/or near the microsomal membranes, inhibits AAPH-initiated lipid peroxidation by inhibiting the initiation and propagation of this reaction, while it prevents microsomal AMVN-initiated lipid peroxidation mainly by inhibiting the propagation of this reaction. In addition, the present results indicate that the group A saponin fraction can inhibit AAPH- or AMVN-initiated lipid peroxidation in mouse liver microsomes by its presence within the membranes and/or by binding to them.

  Antioxidant, lipid peroxidation, soyasaponin, soybean seed hypocotyl, liver microsome (mouse)

  Journal NLM ID: 8700907
  Publisher: Institute Of Applied Biochemistry
  Institutions: Department of Biochemistry, School of Medicine, Fujita Health University, Toyoake, Japan, Department of Internal Medicine, School of Medicine, Fujita Health University, Toyoake, Japan, Department of Clinical Chemistry, School of Health Sciences, Fujita Health University, Toyoake, Japan
  Methods: gel filtration, TLC, HPLC, CC, biological assay
  
   
  
  Glycine max
  CSDB ID 139479 (all data & tools)
• Article ID: 10911
  Tsurumi S, Tsujino Y "Chromosaponin I stimulates the growth of lettuce roots" - Physiologia Plantarum 93 (1995) 785-789
  

  A γ-pyronyl triterpenoid saponin termed chromosaponin 1 (CSI), a conjugate of soyasaponin I and γ-pyrone, was found at 3 mM to stimulate the growth of lettuce root (Lactuca sativa L. ev. Grand Rapids) to about 190% of the control. Since CSI is an amphipathic reductant, the stimulating effect of this saponin was compared with other reductants and other surface-active compounds. Trolox (2-carboxy-2.5.7.8-tetraamethyl-6-chromanol). another amphipathic reductant, also stimulated root growth, while other hydrophilic reductants including ascorbate. NADPH, NADH and glutathione did not. Some surfactants promoted root growth but their stimulating effects were smaller than the optimum effect of CSI. These results suggest a possible Function of CSI as an amphipathic reductant in root growth regulation.

  lettuce, surfactant, saponin, chromosaponin I, Lacuna sativa, reductant, root growth, Trolox

  Publication DOI: 10.1111/j.1399-3054.1995.tb05132.x
  Journal NLM ID: 1256322
  Publisher: Copenhagen: Scandinavian Society For Plant Physiology
  Institutions: Graduate School of Science and Technology, Kobe University, Kobe, Japan
  Methods: HPLC, alkaline hydrolysis, bioassay
  
   
  
  Pisum sativum
  CSDB ID 245320 (all data & tools)
• Article ID: 11177
  Arao T, Kinjo J, Nohara T, Isobe R "Oleanene-type triterpene glycosides from Puerariae radix. IV. Six new saponins from Pueraria lobata" - Chemical and Pharmaceutical Bulletin 45(2) (1997) 362-366
  

  From Puerariae Radix, the root of Pueraria lobata (Leguminosae), six new oleanene-type triterpene glycosides, called kudzusaponins A1 (1), A2 (2), Ar (3), SA4 (5), and SB1 (6) were isolated together with kudzusaponin A3 (7), soyasaponins SA3 (8), and I (9). The structures of 1-6 were determined to be 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-arabinopyranosyl-(1→2)β-D-glucuronopyranosy l kudzusapogenol A 22-O-β-D-xylopyranoside, 3-O-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl kudzusapogenol A, 3-O-β-D-glucopyranosyl-(1→2)-β-D-glucuronopyranosyl kudzusapogenol A, 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-glucoronopyranosyl kudzusapogenol A, 3-O-β-D-glucuronopyranosyl[(1→2)-β-D-glucuronopyranosyl soyasapogenol A22-O-α-L-arabinopyranoside, and 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl (β-fabatriosyl) soyasapogenol B 22-O-α-L-arabinopyranoside, respectively.

  tandem mass spectrometry, Leguminosae, triterpenoidal saponin, Pueraria lobata, oleanene-type triterpene bisdesmoside, kudzusaponin

  NCBI PubMed ID: 9118450
  Publication DOI: 10.1248/cpb.45.362
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Kumamoto University, Japan.
  Methods: 13C NMR, 1H NMR, FAB-MS, sugar analysis, TLC, GC, MS/MS, chemical methods, HPLC, extraction, CID-MS
  
   
  
  Pueraria lobata, Pueraria radix
  CSDB ID 60593 (all data & tools)
• Article ID: 11350
  Kinjo J, Hatakeyama M, Udayama M, Tsutanaga Y, Yamashita M, Nohara T, Yoshiki Y, Okubo K "HPLC profile analysis of oleanene-glucuronides in several edible beans" - Bioscience, Biotechnology, and Biochemistry 62(3) (1998) 429-433
  

  HPLC analysis and yield of oleanene-glucuronide (OG) was done on some commercially available edible beans: seeds of Glycine max, Glycine max cv. Kuromame, Phaseolus vulgaris cv. Torosuku, Phaseolus vulgaris cv. Toramame, Phaseolus vulgaris cv. Taishokintoki, Phaseolus coccineus cv. Ooshirobana, Phaseolus coccineus cv. Murasakihanamame, Vigna unguiculata cv. Chuguro, Vigna angularis cv. Dainagon, Arachis hypogaea, Pisum sativum, and Vicia faba. All the beans listed above have OG, though in varying the amounts. Furthermore the HPLC profiles of beans belonging to the same genus were very similar except for that of the Vigna genus. There was no great difference of the HPLC profiles with respect to the cultivated varieties, The structures of the major OGs in each type of beans were identified as soyasaponins I (1) and V (2), and phaseoside I (3) (Phaseolus vulgaris and P. coccineus); 1 and soyasaponin II (4) (Glycine max); 1 and 2 (Vigna unguiculata); 1 (Pisum sativum, Arachis hypogaea and Vicia faba). In contrast, those in Dainagon (Vigna angularis cv. Dainagon) were identified as azukisaponins II (5) and VI (6).

  Leguminosae, triterpene saponin, oleanene glucuronide, HPLC analysis, bean

  NCBI PubMed ID: 9571771
  Publication DOI: 10.1271/bbb.62.429
  Journal NLM ID: 9205717
  Publisher: Japan Society for Bioscience, Biotechnology, and Agrochemistry
  Institutions: Faculty of Pharmaceutical Sciences, Kumamoto University, Kumamoto, Japan, Department of Environmental Bioremediation, Graduate School of Agricultrue, Tohoku University, Sendai, Japan
  Methods: 13C NMR, 1H NMR, HPLC, extraction, optical rotation measurement, CC, FB-MS
  
   
  
  Phaseolus vulgaris, Phaseolus coccineus, Glycine max, Vigna unguiculata, Vicia faba, Arachis hypogaea, Pisum sativum
  CSDB ID 61377 (all data & tools)
• Article ID: 11397
  Kinjo J, Imagire M, Udayama M, Arao T, Nohara T "Structure-hepatoprotective relationships study of soyasaponins I-IV having soyasapogenol B as aglycone" - Planta Medica 64(3) (1998) 233-236
  

  As a part of our study on the leguminous plants, we investigated the constituents of the aerial parts of Glycine soya. We isolated and identified four known saponins, soyasaponins I, II, III, and IV which have the same aglycone, soyasapogenol B, As a part of our studies concerning hepatoprotective drugs, we also examined the hepatoprotective actions of these saponins towards immunologically induced liver injury on primary cultured rat hepatocytes, The action of soyasaponin II was almost comparable with that of soyasaponin I, whereas those of soyasaponin III and IV were more effective than soyasaponins I and II. This means that the disaccharide group shows greater action than the trisaccharide group. Futhermore, the saponin having a hexosyl unit shows a slightly greater action than that of the pentosyl unit in each disaccharide group or trisaccharide group. Structure-activity relationships suggest that the sugar moiety linked at C-3 may play an important role in hepatoprotective actions of soybean saponins.

  hepatoprotective activity, Leguminosae, triterpenoidal saponin, soyasaponin, primary cultured rat hepatocytes, immunological liver injury, Glycine soya

  NCBI PubMed ID: 9581521
  Publication DOI: 10.1055/s-2006-957416
  Journal NLM ID: 0066751
  Publisher: George Thieme
  Correspondence: Kinjo J
  Institutions: Department of Microbiology and Molecular Genetics, Oklahoma State University, Stillwater, USA, National Research Council Associate, c/o GED, US EPA Gulf Breeze, USA, The Volcani Center, Agricultural Organization, Bet Dagan, Israel and 4USDA-ARS Western Regional Research Center, Albany, CA, USA
  Methods: 13C NMR, 1H NMR, FAB-MS, HPLC, extraction, optical rotation measurement, CC, hepatoprotective assay, statisitical analysis
  
   
  
  Glycine soya
  CSDB ID 61601 (all data & tools)
• Article ID: 11605
  Kinjo J, Udayama M, Hatakeyama M, Ikeda T, Sohno Y, Yoshiki Y, Okubo K, Nohara T "Hepatoprotective effects of oleanene glucuronides in several edible beans" - Shōyakugaku Zasshi = Natural Medicines 53(3) (1999) 141-144
  

  We examined the hepatoprotective effects of oleanene glucuronides (OGs) prepared from some Japanese edible beans. Total OGs from soybean (seeds of Glycine max), adzuki bean (seeds of Vigna angularis), kidney bean (seeds of Phaseolus vulgaris) and scarlet runner bean (seeds of Phaseolus coccineus) showed a hepatoprotective action at 500 μg/ml. The order of potency was adzuki bean OG ≥ kidney bean OG ≥ soybean OG » scarlet runner bean OG. Purified OGs obtained from these beans also showed hepatoprotective actions at 500 μM. The order of potency was soyasaponin I > soyasaponin V > azukisaponin VI > phaseoside I. The difference in the potency of total OG of each bean seemed to reflect the composition of pure OG.

  hepatoprotective activity, Leguminosae, triterpenoidal saponin, oleanene glucuronide, edible bean

  Journal NLM ID: 9441222
  WWW link: https://dl.ndl.go.jp/info:ndljp/pid/10759457
  Publisher: Kyoto: Nihon Shōyaku Gakkai
  Institutions: Faculty of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-Honmachi, Kumamoto 862-0973, Japan, Department of Environmental Bioremediation, Graduate School of Agriculture, Tohoku University, Tsutsumidori, 1-1 Amamiya-machi, Sendai 981-0912
  Methods: HPLC, statistical analysis, hepatoprotective activity assay
  
   
  
  Glycine max, Vigna angularis, Phaseolus vulgaris, Phaseolus coccineus
  CSDB ID 62201 (all data & tools)
• Article ID: 11677
  Kinjo J, Aoki K, Okawa M, Shii Y, Hirakawa T, Nohara T, Nakajima Y, Yamazaki T, Hosono T, Someya M, Niiho Y, Kurashige "HPLC profile analysis of hepatoprotective oleanene-glucuronides in Puerariae Flos" - Chemical and Pharmaceutical Bulletin 47(5) (1999) 708-710
  

  In order to confirm the constitution of hepatoprotective oleanene glucuronide (OG), HPLC profile analyses of the total OG fractions of both Puerariae Thomsonii Flos (the flowers of Pueraria thomsonii) and Puerariae Lobatae Flos (the flowers of P. lobata) were performed. No remarkable difference in the HPLC profiles with respect to OGs in the flowers was shown, in contrast to those of the roots. By repeated chromatography of the total OG fraction of Puerariae Thomsonii Flos, soyasaponin I (1), kaikasaponin III (2) and kakkasaponin I (3), which had been already isolated from Puerariae Lobatae Flos, were obtained. The hepatoprotective activity of 2 towards immunologically induced liver injury was significantly more effective than that of 1. This information supported previously obtained structure- hepatoprotective relationship data which was measured on another model. The structure-activity relationship information which suggested that the hydroxymethyl group of the galactosyl unit would enhance the hepatoprotective activity was also substantiated.

  hepatoprotective activity, triterpenoidal saponin, Pueraria lobata, oleanene glucuronide, Pueraria thomsonii, HPLC profile analysis

  NCBI PubMed ID: 10361701
  Publication DOI: 10.1248/cpb.47.708
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-Honmachim Kumamoto 862-0973, Japan, Tsukuba Research Institute, Ohta's Isan Co., Ltd., 957 Shishiko, Ushiku, Ibaraki 300-1231, Japan
  Methods: HPLC, hepatoprotective activity assay
  
   
  
  Pueraria thomsonii, Pueraria lobata
  CSDB ID 62485 (all data & tools)
• Article ID: 11741
  Simonet AM, Stochmal A, Oleszek W, Macías FA "Saponins and polar compounds from Trifolium resupinatum" - Phytochemistry 51(8) (1999) 1065-1067
  

  In addition to the known soyasaponin I, 3-O-[α-L-rhamnopyranosyl(1→2)-β-D-galactopyranosyl(1→2-β-D-glucuronopyranosyl]-22-O-[β-D-glucuronopyranosyl(1→2)-β-D-glucopyranosyl]soyasapogenol B, soyasaponin II, 3-O-β-D-glucopyranosyl sitosterol, 3-O-β-D-glucopyranosyl stigmasterol and 3-O-α-L-arabinopyranosyl-(1→6)-β-D-glucopyranosyl]oct-1-ene-3-ol, the new saponin, 3-O-α-L-rhamnopyranosyl(1→2)-β-D-galactopyranosyl(1→2)-β-D-glucuronopyranosyl]-22-O-β-D-glucopyranosyl soyasapogenol B (2) was isolated and characterised from the seed saponins fraction of Trifolium resupinatum. The structural determination is based on spectroscopic methods (including DQF-COSY, HETCOR, TOCSY, ROESY and NOEs experiments).

  glycosides, saponins, Leguminosae, clover seeds, Persian clover, Trifolium resupinatum

  Publication DOI: 10.1016/S0031-9422(99)00192-2
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Correspondence: Macías FA
  Institutions: Departamento de Quı́mica Orgánica, Facultad de Ciencias, Universidad de Cádiz, C/República Saharaui s/n, Apdo. 40, 11510-Puerto Real, Cádiz, Spain, Department of Biochemistry, Institute of Soil and Plant Cultivation, ul., Czartoryskich 8, Osada Palacowa, 24-100, Pulawy, Poland
  Methods: 13C NMR, 1H NMR, FAB-MS, acid hydrolysis, optical rotation measurement, ROESY, TOCSY, DQF-COSY, HETCOR
  
   
  
  Trifolium resupinatum
  CSDB ID 62741 (all data & tools)
• Article ID: 11987
  Ahamed A, Tsurumi S, Ozaki M, Amakawa T "Chromosaponin I stimulates the sugar taste receptor cells of the blowfly, Phormia regina" - Comparative Biochemistry and Physiology. Part A, Physiology 125(3) (2000) 343-349
  

  Chromosaponin I (CSI), a gamma-pyronyl-triterpenoid saponin isolated from pea and other leguminous plants, stimulates the growth of roots in a variety of plants. In the present work, we introduce CSI as a sugar taste substance for the blowfly, Phormia regina. The blowfly has taste chemosensilla on the labellum. The sensory receptor cells in the chemosensillum are highly specialized for the tastes of sugar, salt and water, respectively. Application of CSI induced the feeding response of blowflies including full proboscis extension. CSI also induced impulses of the sugar taste receptor cell in the LL-type sensillum. The optimum concentration of CSI in these responses was 0.1 mM which is much lower than that of sucrose. Based on the comparison of dose-response relationships, CSI is 100 times more effective than sucrose in stimulating the sugar taste receptor cells. CSI-induced impulses appeared after a significant latency compared with sucrose. As far as we know, this is the first report describing that a natural saponin induces sugar responses in insects. CSI is a unique saponin because of its bifunctional property in plants and insects.

  triterpenoid, soyasaponin I, chromosaponin I, blowfly, electrophysiological response, Phormia regina, proboscis extension reflex, sugar taste, transduction mechanism

  NCBI PubMed ID: 10794963
  Publication DOI: 10.1016/s1095-6433(00)00164-1
  Journal NLM ID: 9516062
  Publisher: New York Ny: Elsevier Science
  Correspondence: tsurumis@scitec.kobe-u.ac.jp
  Institutions: Graduate School of Science and Technology, Kobe University, Kobe, Japan, Radioisotope Research Center, Kobe University, Kobe, Japan, Department of Applied Biology, Faculty of Textile Science, Kyoto Institute of Technology, Kyoto, Japan, Faculty of Human Development, Kobe University, Kobe, Japan
  Methods: biological assays, alkaline hydrolysis, extraction, CC
  
   
  
  Pisum sativum
  CSDB ID 64686 (all data & tools)
• Article ID: 12035
  Berhow MA, Wagner ED, Vaughn SF, Plewa MJ "Characterization and antimutagenic activity of soybean saponins" - Mutation Research 448(1) (2000) 11-22
  

  An extract was prepared from a commercial soybean-processing by-product (soybean molasses) and was fractionated into purified chemical components. In previous work, this extract (phytochemical concentrate, PCC) repressed induced genomic DNA damage, whole cell clastogenicity and point mutation in cultured mammalian cells. In the current study, a chemical fraction was isolated from PCC using preparative high-performance liquid chromatography (HPLC). This fraction, PCC100, repressed 2-acetoxyacetylaminofluorene (2AAAF)-induced DNA damage in Chinese hamster ovary (CHO) cells as measured by single cell gel electrophoresis (alkaline Comet assay). Using liquid chromatography-electrospray ionization-mass spectroscopy and 1H and 13C nuclear magnetic resonance (NMR) spectroscopy, PCC100 was shown to consist of a mixture of group B soyasaponins and 2,3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP) soyasaponins. These include soyasaponins I, II, III, IV, V, Be, βg, βa, γg and γa. Purified soyasapogenol B aglycone prepared from fraction PCC100 demonstrated significant antigenotoxic activity against 2AAAF. To our knowledge, these data demonstrate for the first time the antimutagenic activity of soybean saponins in mammalian cells.

  soybean, Glycine max, soyasaponins, antimutagenic activity

  NCBI PubMed ID: 10751618
  Publication DOI: 10.1016/s0027-5107(99)00225-0
  Journal NLM ID: 0400763
  Publisher: Elsevier
  Correspondence: m-plewa@uiuc.edu
  Institutions: United States Department of Agriculture, Agricultural Research Service, National Center for Agricultural Utilization Research, Peoria, IL, USA, Department of Crop Sciences, College of Agricultural, Consumer and Environmental Sciences, University of Illinois at Urbana-Champaign, Urbana, USA
  Methods: 13C NMR, 1H NMR, TLC, acid hydrolysis, biological assays, HPLC, extraction, mutation analysis, CC, LC-ESI-MS, GC-CI-MS, cytotoxicity assay, evaporation, gel electrophoresis
  
   
  
  Glycine max
  CSDB ID 64923 (all data & tools)
• Article ID: 12236
  Hirakawa T, Okawa M, Kinjo J, Nohara T "A new oleanene glucuronide obtained from the aerial parts of Melilotus officinalis" - Chemical and Pharmaceutical Bulletin 48(2) (2000) 286-287
  

  A new oleanene glucuronide called melilotus-saponin O2 (1) was isolated together with three known ones (soyasaponin i, astragaloside VIII, wistariasaponin D) form the aerial parts of Melilotus officinalis (L>) PALLAS (Leguminosae). The structure of 1 was determined to be 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranosyl-(1→2)-β-D-glucuronopyranosyl melilotigenin by spectroscopic and chemical methods.

  Leguminosae, triterpene saponin, oleanene glucuronide, Melilotus officinalis, melilotus-saponin, melilotigenin

  NCBI PubMed ID: 10705521
  Publication DOI: 10.1248/cpb.48.286
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Kumamoto University, Kumamoto, Japan
  Methods: 13C NMR, 1H NMR, methylation, FAB-MS, TLC, acid hydrolysis, HPLC, enzymatic digestion, extraction, optical rotation measurement, reduction, CC, derivatization, evaporation, HR-FAB-MS
  
   
  
  Melilotus officinalis
  CSDB ID 65792 (all data & tools)
• Article ID: 12294
  Kinjo J, Yokomizo K, Hirakawa T, Shii Y, Nohara T, Uyeda M "Anti-herpes virus activity of fabaceous triterpenoidal saponins" - Biological and Pharmaceutical Bulletin 23(7) (2000) 887-889
  

  Anti-herpes simplex virus type 1 (HSV-1) activity of oleanane-type triterpenoidal saponins obtained from some fabaceous plants were examined. Among sophoradiol glycosides, the order of potency was kaikasaponins III>I>>sophoradiol monoglucuronide. It was suggested that the trisaccharide group showed greater action than the disaccharide group. Neither the monoglucuronide of sophoradiol nor that of soyasapogenol B showed activity. Among the trisaccharide group of soyasapogenol B, the order of activity was azukisaponin V>soyasaponin II>astragaloside VIII>>soyasaponin I. Therefore, the saponin having a glucosyl unit in the central sugar moiety seemed to show greater action. In comparison with the activities for a group having the same trisaccharide, the potency of the sapogenol moieties was found to be in the order of soyasapogenol E>sophoradiol>>soyasapogenol B. Hence, the carbonyl group at C-22 would be more effective than the hydroxyl group in anti-HSV-1 activity, while the hydroxyl group at C-24 could reduce the activity.

  structure-activity relationship, Fabaceae, triterpenoidal saponin, anti-herpes simplex virus activity, oleanane-type triterpene

  NCBI PubMed ID: 10919372
  Publication DOI: 10.1248/bpb.23.887
  Journal NLM ID: 9311984
  Publisher: Pharmaceutical Society of Japan
  Correspondence: Nohara T
  Institutions: Laboratory of Natural Medicines, Faculty of Pharmaceutical Sciences, Kumamoto University, Kumamoto, Japan, Laboratory of Pharmaceutical Microbiology, Faculty of Pharmaceutical Sciences, Kumamoto University, Kumamoto, Japan
  Methods: cytotoxicity assay, optical density measurement, antiviral assay
  
   
  
  (plant)
  CSDB ID 66028 (all data & tools)
• Article ID: 12609
  Rao AV, Gurfinkel DM "The bioactivity of saponins: triterpenoid and steroidal glycosides" - Drug Metabolism and Drug Interactions 17(1-4) (2000) 211-235
  

  Triterpenoid and steroidal glycosides, referred to collectively as saponins, are bioactive compounds present naturally in many plants. They have considerable potential as pharmaceutical and/or nutraceutical agents in natural or synthetic form. Saponins, from a variety of sources, have been shown to have hypocholesterolemic, anticoagulant, anticarcinogenic, hepatoprotective, hypoglycemic, immunomodulatory, neuroprotective, anti-inflammatory and anti-oxidant activity. This paper reviews saponin research of the last decade, focussing on developments in understanding their mechanism of action and structure-activity relationships. Virtually all of this work has used animal and in vitro models. To date there are very few human data.

  immunomodulation, hypoglycemic activity, antiinflammatory activity, anti-oxidant activity, Hepatoprotection, steroidal glycosides, saponins, neuroprotection, triterpenoid glycosides, hypocholesterolemic activity, anti-coagulation, anticarcinogen

  NCBI PubMed ID: 11201296
  Publication DOI: 10.1515/dmdi.2000.17.1-4.211
  Journal NLM ID: 8904736
  Publisher: Berlin: De Gruyter
  Correspondence: v.rao@utoronto.ca
  Institutions: Department of Nutritional Sciences, University of Toronto, Toronto, Canada
  
   
  
  Glycine max
  CSDB ID 67381 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: astragaloside IV, astragalus saponin AS I, cycloastragenol
Compound class: saponin glycoside, glycoside, triterpenoid glycoside
Contained glycoepitopes: IEDB_114701,IEDB_142488,IEDB_146664,IEDB_167188,IEDB_174332,IEDB_983931,SB_192

• Article ID: 11372
  Bedir E, Calis I, Zerbe O, Sticher O "Cyclocephaloside I: A novel cycloartane-type glycoside from Astragalus microcephalus" - Journal of Natural Products 61(4) (1998) 503-505
  

  A novel cycloartane-type glycoside, cyclocephaloside I (1) was isolated from the roots of Astragalus microcephalus in addition to known glycosides cyclocanthoside E (2) and astragaloside IV (3). The structure of 1 was determined by spectral (IR, H-1 and C-13 NMR, and FABMS) and chemical (acetylation) methods and established as 20,25-epoxy-3 beta-(beta-D-xylopyranosyl)oxy-6 alpha-(beta-D-glucopyranosyl)oxy-cycloartane-16 beta,24 alpha-diol.

  NMR, cycloartane, Astraglus

  Publication DOI: 10.1021/np9704011
  Journal NLM ID: 7906882
  Publisher: American Society of Pharmacognosy
  Correspondence: Calis I
  Institutions: Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University, Ankara, Turkey, Swiss Federal Institute of Technology (ETH) Zürich, Department of Pharmacy, Zürich, Switzerland
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, extraction, optical rotation measurement, acetylation, ROESY, TOCSY, HMBC, HMQC, COSY, MPLC
  
   
  
  Astragalus microcephalus
  CSDB ID 61474 (all data & tools)
• Article ID: 11375
  Bedir E, Calis I, Aquino R, Piacente S, Pizza C "Cycloartane triterpene glycosides from the roots of Astragalus brachypterus and Astragalus microcephalus" - Journal of Natural Products 61(12) (1998) 1469-1472
  

  Three new cycloartane-type triterpene glycosides, brachyosides A (1), B (3), and C (2), from the roots of Astragalus brachypterus and one new glycoside, cyclocephaloside II (4), from the roots of Astragalusmicrocephalus have been isolated together with five known saponins, astragalosides I, II, and IV, cyclocanthoside E, and cycloastragenol. The structures of the new compounds were established as 3-O-[beta-D-xylopyranosyl(1-->3)-beta-D-xylopyranosyl-6-O-beta-D-gluc opyranosyl-3beta,6alpha,16beta,24(S),25-pentahydrox ycycloartane (1), 3-O-beta-D-xylopyranosyl-6-O-beta-D-glucopyranosyl-24-O-beta-D-glucop yranosyl-3beta,6alpha,16beta,24(S),25-pentahydroxyc ycloartane (2), 20(R),24(S)-epoxy-6-O-beta-D-glucopyranosyl-3beta,6alpha,16beta , 25-tetrahydroxycycloartane (3), and 20(R), 24(S)-epoxy-3-O-(4'-O-acetyl)-beta-D-xylopyranosyl-6-O-beta-D-glucopy ranosyl-3beta,6alpha,16beta,25-tetrahydroxycycloart ane (4). For the structure elucidations, 1D- and 2D-NMR experiments and FABMS were used.

  NMR, spectroscopy

  NCBI PubMed ID: 9868145
  Publication DOI: 10.1021/np9801763
  Journal NLM ID: 7906882
  Publisher: American Society of Pharmacognosy
  Correspondence: Calis I
  Institutions: Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University, Ankara, Turkey, Facoltà di Farmacia, Università degli Studi di Salerno, Penta di Fisciano, Salerno, Italy
  Methods: 13C NMR, 1H NMR, FAB-MS, extraction, optical rotation measurement, TOCSY, CC, DQF-COSY, HMBC, DEPT, HOHAHA, HSQC
  
   
  
  Astragalus microcephalus
  CSDB ID 61484 (all data & tools)
• Article ID: 11735
  Bedir E, Calis I, Aquino R, Piacente S, Pizza C "Trojanoside H: a cycloartane-type glycoside from the aerial parts of Astragalus trojanus" - Phytochemistry 51(8) (1999) 1017-1020
  

  A novel cycloartane-type glycoside was isolated from the aerial parts of Astragalus trojanus along with the known glycosides astragaloside II, astragaloside IV, astragaloside VII, brachyoside B, brachyoside C and the pterocarpan derivative maackiain. The structure of 1 was determined by spectral methods (1-D and 2-D NMR, and FABMS) and established as 3-O-β-[α-L-arabinopyranosyl(1→2)β-D-xylopyranosyl]-6-O-β-D-glucopyranosyl-20(R),24(S)-epoxy-3β,6α,16β,25-tetrahydroxycycloartane.

  isoflavone, Leguminosae, Astragalus trojanus, cycloartane type glycoside, trojanoside H, maackiain

  Publication DOI: 10.1016/S0031-9422(99)00035-7
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Correspondence: Çalis I
  Institutions: Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University, Ankara, Turkey, Dipartimento di Scienze Farmaceutiche, Università degli Studi di Salerno, 84084 Penta di Fisciano, Salerno, Italy
  Methods: 13C NMR, 1H NMR, FAB-MS, optical rotation measurement, ROESY, TOCSY, DQF-COSY, HMBC, HSQC
  
   
  
  Astragalus trojanus
  CSDB ID 62718 (all data & tools)
• Article ID: 11830
  Bedir E, Calis I, Aquino R, Piacente S, Pizza C "Secondary metabolites from the roots of Astragalus trojanus" - Journal of Natural Products 62(4) (1999) 563-568
  

  Six novel cycloartane-type glycosides were isolated from the roots of Astragalus trojanus. Two of these, compounds 1 and 2, have (20R,24S)-epoxy-3β,6α,16β,25-tetrahydroxycycloartane as the aglycon, while compounds 3-6 possess 3β,6α,16β,(24S),25-pentahydroxycycloartane as the aglycon. The saccharide moieties linked to the C-3, C-6, and C-24 or C-25 positions of the aglycons in 1-6 contained either xylopyranose, glucopyranose, rhamnopyranose, or arabinopyranose units. Structure elucidation of compounds 1-6 was accomplished through the extensive use of 1D and 2D NMR techniques. In addition, a new oleanene glycoside (7) and a new tryptophan derivative (8) were also isolated and characterized.

  glycoside, cycloartane, Astragalus trojanus

  NCBI PubMed ID: 10217709
  Publication DOI: 10.1021/np980399t
  Journal NLM ID: 7906882
  Publisher: American Society of Pharmacognosy
  Correspondence: Çalis I
  Institutions: Dipartimento di Scienze Farmaceutiche, Università degli Studi di Salerno, 84084 Penta di Fisciano, Salerno, Italy, epartment of Pharmacognosy, Faculty of Pharmacy, Hacettepe University, Ankara, Turkey
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, optical rotation measurement, TOCSY, DQF-COSY, HMBC, HOHAHA, HSQC
  
   
  
  Astragalus trojanus
  CSDB ID 63173 (all data & tools)
• Article ID: 12024
  Bedir E, Pugh N, Calis I, Pasco DS, Khan IA "Immunostimulatory effects of cycloartane-type triterpene glycosides from Astragalus species" - Biological and Pharmaceutical Bulletin 23(7) (2000) 834-837
  

  In the course of our research on the oligoglycosidic constituents of Turkish Astragalus species, we have isolated a number of cycloartane-type triterpene glycosides. The current study examines the immunostimulatory effects of nineteen of these cycloartane-type compounds using a transcription-based bioassay for Nuclear Factor kappa B (NF-κB) activation in a human macrophage/monocyte cell line, THP-1. All compounds were inactive at 100 μg/ml except astragaloside I which increased NF-κB directed luciferase expression to levels about 65% as compared with maximal stimulation by E. coli lipopolysaccharide (LPS) at 10 μg/ml. None of the compounds were active at low dosage levels (0.1 μg/ml) in combination with 50 ng/ml LPS. Astragaloside I also increased mRNA expression of the inflammatory cytokines interleukin-1β (IL-1β) and tumor necrosis factor-α (TNF-α) as measured using reverse transcriptase-polymerase chain reaction (RT)-PCR. Based on these results it is clear that certain structural features are required for immunostimulation of cycloartane-type triterpene glycosides.

  macrophage, immunostimulatory, THP-1, Astragalus, astragaloside I, nuclear factor kappa B (NF-κB)

  NCBI PubMed ID: 10919362
  Publication DOI: 10.1248/bpb.23.834
  Journal NLM ID: 9311984
  Publisher: Pharmaceutical Society of Japan
  Correspondence: Bedir E ; Caliş I ; Khan IA
  Institutions: Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University, Ankara, Turkey, National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, The University of Missisippi, Missisippi, USA, Department of Pharmacognosy, School of Pharmacy, The University of Missisippi, Missisippi, USA
  Methods: 13C NMR, 1H NMR, NMR-2D, IR, PCR, MS, RT-PCR, macrophage activity assay
  
   
  
  Astragalus microcephalus, Astragalus melanophrurius
  CSDB ID 64866 (all data & tools)
• Article ID: 12662
  Press JB, Reynolds RC, May RD, Marciani DJ "Structure/function relationships of immunostimulating saponins" - Book: Studies in Natural Products Chemistry (2000) Vol. 24, Chapter E, 131-174
  

  Saponins are widely distributed plant glycosides comprising either steroidal or triterpene aglycones linked to carbohydrate chains. The triterpene saponins from Quillaja saponaria Molina, Gypsophila sp., and Saponaria officinalis, have unique immunostimulating and immunomodulating properties. Analysis of their structure/function relationships shows common structural characteristics (i.e. a triterpene aglycone containing an aldehyde group at C-4, and oligosaccharide chains attached to positions 3 and 28) that appear to account for these saponins’ effects on the immune system. The crucial role of the saponin's triterpene imine-forming carbonyl group in immune stimulating and modulating activities is supported by the following: i) saponins lacking such an aldehyde group are devoid of these activities, and ii) modification of the quillaja saponin's aldehyde group results in the loss of such activities. The oligosaccharide chains of these saponins appear to mediate targeting of saponins to antigen presenting cells (APCs), thus enhancing their immunological properties. The saponins from Quillaja saponaria Molina also contain two acyl moieties: a normonoterpene carboxylic acid and a normonoterpene carboxylic acid glycoside, which are linked linearly to a fucosyl residue attached at position C-28. These acyl groups appear to be responsible for the stimulation of cytotoxic T cells (CTLs) against exogenous antigens. Removal of the acyl moieties by mild basic hydrolysis yields deacylated quillaja saponins that are structurally and functionally comparable to the non-acylated Gypsophila sp. and Saponaria officinalis saponins; all these non-acylated saponins stimulate a poor primary immune response. Replacement of the quillaja saponin's acyl moieties with other hydrophobic groups alters their immune stimulating and modulating properties.

  plant, Immunomodulating activity, saponins

  Publication DOI: 10.1016/S1572-5995(00)80045-9
  Publisher: New York: Elsevier
  Editors: Atta-ur-Rahman
  Institutions: Galenica Pharmaceuticals, Inc., Frederick, USA, Southern Research Institute, Birmingham, USA
  
   
  
  Astragalus membranaceus
  CSDB ID 67776 (all data & tools)
• Article ID: 12852
  Yao M, Qi Y, Bi K, Wang X, Luo X, Che C "A precolumn derivatization high-performance liquid chromatographic method with improved sensitivity and specificity for the determination of astragaloside IV in Radix astragali" - Journal of Chromatographic Science 38(8) (2000) 325-328
  

  A reversed-phase high-performance liquid chromatographic method is developed for the determination of astragaloside (AGS) IV, which is known as the active constituent of Radix Astragali. The method uses precolumn derivatization with benzoyl chloride to form the benzoyl ester of AGS IV quantitatively and is carried out with a wide-ranging concentration (0.004-0.080 mg/mL) of the derivatized AGS IV. The eluent consists of 90% methanol, 4% tetrahydrofuran, 6% water, and 0.2% triethylamine, with vitamin D3 added as the internal standard.

  derivatives, RP-HPLC, Radix astragali, astragaloside IV, benzoylation

  NCBI PubMed ID: 10955506
  Publication DOI: 10.1093/chromsci/38.8.325
  Journal NLM ID: 0173225
  Publisher: Oxford: Oxford University Press
  Institutions: Shenyang Pharmaceutical University, Shenyang, China, Department of Chemistry, Hong Kong University of Science & Technology, School of Chinese Medicine, The Chinese University of Hong Kong, Shatin, Hong Kong, China
  Methods: HPLC, derivatization
  
   
  
  Astragalus membranaceus, Astragalus mongholicus, Astragalus chrysopterus, Astragalus ernestii
  CSDB ID 68732 (all data & tools)