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2020 | OriginalPaper | Buchkapitel

3. Metabolic and Functional Diversity of Saponins

verfasst von : Mostafa Abdelrahman, Sudisha Jogaiah

Erschienen in: Bioactive Molecules in Plant Defense

Verlag: Springer International Publishing

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Abstract

The ‘saponin’ word is originated from Latin name ‘sāpō’ means ‘soap’, as saponins make foams when they are shaken using water. These are a varied class of surface active and nonvolatile secondary metabolites are broadly dispersed in nature, existing in diverse species of plants, including both monocot and dicot. Saponins are 30-carbon skeleton molecules derived from oxidosqualene precursor that consisted of nonpolar aglycones, to which one or more polar monosugar molecules are attached. The polar (sugar moieties) and nonpolar (aglycones) structures mixture in the saponin compounds describe their soap like behavior in water and provide the base for their biological activities. Although saponin is considered major group of plant natural products, their functions in plant biological process are not fully understood and saponins are usually recognized to have significant functions in plant defense mechanisms against pathogens, herbivores and pests. Saponin compounds have a wide array of characters, such as emulsifying and foaming, bitterness and sweetness, antimicrobial, insecticidal, as well as pharmacological and medicinal properties. Although in the early times it may be suitable to categorize saponin compounds according to their biological and/or physicochemical activities, currently with the high throughput in chemistry and mass spectrometry, the structural diversity of saponin compounds became the main classification scheme. In this chapter, we will try to describe the different types of saponin compounds and their distributions in the different plant species. The new isolated saponin compounds from different plants will also be listed as a source information for future biological studies.

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Literatur
Zurück zum Zitat Abdelrahman M, Hirata S, Ito S, Yamauchi N, Shigyo M (2014) Compartmentation and localization of bioactive metabolites in different organs of Allium roylei. Biosci Biotechnol Biochem 78:1112–1122PubMedCrossRef Abdelrahman M, Hirata S, Ito S, Yamauchi N, Shigyo M (2014) Compartmentation and localization of bioactive metabolites in different organs of Allium roylei. Biosci Biotechnol Biochem 78:1112–1122PubMedCrossRef
Zurück zum Zitat Abdelrahman M, El-Sayed M, Sato S, Hirakawa H, Ito S-I, Tanaka K, Mine Y, Sugiyama N, Suzuki Y, Yamauchi N, Shigyo M (2017a) RNA-sequencing-based transcriptome and biochemical analyses of steroidal saponin pathway in a complete set of Allium fistulosum-A. cepa monosomic addition lines. PLoS One 12:e0181784PubMedPubMedCentralCrossRef Abdelrahman M, El-Sayed M, Sato S, Hirakawa H, Ito S-I, Tanaka K, Mine Y, Sugiyama N, Suzuki Y, Yamauchi N, Shigyo M (2017a) RNA-sequencing-based transcriptome and biochemical analyses of steroidal saponin pathway in a complete set of Allium fistulosum-A. cepa monosomic addition lines. PLoS One 12:e0181784PubMedPubMedCentralCrossRef
Zurück zum Zitat Abdelrahman M, Mahmoud HYAH, El-Sayed M, Tanaka S, Tran LS (2017b) Isolation and characterization of Cepa2, a natural alliospiroside A, from shallot (Allium cepa L. Aggregatum group) with anticancer activity. Plant Physiol Biochem 116:167–173PubMedCrossRef Abdelrahman M, Mahmoud HYAH, El-Sayed M, Tanaka S, Tran LS (2017b) Isolation and characterization of Cepa2, a natural alliospiroside A, from shallot (Allium cepa L. Aggregatum group) with anticancer activity. Plant Physiol Biochem 116:167–173PubMedCrossRef
Zurück zum Zitat Abdelrahman M, Hirata S, Sawada Y, Hirai MY, Sato S, Hirakawa H, Mine Y, Tanaka K, Shigyo M (2019) Widely targeted metabolome and transcriptome landscapes of Allium fistulosum–A. cepa chromosome addition lines revealed a flavonoid hot spot on chromosome 5A. Sci Rep 9:3541PubMedPubMedCentralCrossRef Abdelrahman M, Hirata S, Sawada Y, Hirai MY, Sato S, Hirakawa H, Mine Y, Tanaka K, Shigyo M (2019) Widely targeted metabolome and transcriptome landscapes of Allium fistulosumA. cepa chromosome addition lines revealed a flavonoid hot spot on chromosome 5A. Sci Rep 9:3541PubMedPubMedCentralCrossRef
Zurück zum Zitat Abe I, Rohmer M, Prestwich GC (1993) Enzymatic cyclization of squalene and oxidosqualene to sterols and triterpenes. Chem Rev 93:2189–2206CrossRef Abe I, Rohmer M, Prestwich GC (1993) Enzymatic cyclization of squalene and oxidosqualene to sterols and triterpenes. Chem Rev 93:2189–2206CrossRef
Zurück zum Zitat Adao CR, Da Silva BP, Parente JP (2011) A new steroidal saponin from Allium ampeloprasum var. porrum with antiinflammatory and gastroprotective effects. Phytochem Lett 4:306–310CrossRef Adao CR, Da Silva BP, Parente JP (2011) A new steroidal saponin from Allium ampeloprasum var. porrum with antiinflammatory and gastroprotective effects. Phytochem Lett 4:306–310CrossRef
Zurück zum Zitat Augustin JM, Kuzina V, Andersen SB, Bak S (2011) Molecular activities, biosynthesis and evolution of triterpenoid saponins. Phytochemistry 72:435–457PubMedCrossRef Augustin JM, Kuzina V, Andersen SB, Bak S (2011) Molecular activities, biosynthesis and evolution of triterpenoid saponins. Phytochemistry 72:435–457PubMedCrossRef
Zurück zum Zitat Berhow MA, Wagner ED, Vaughn SF, Plewa MJ (2000) Characterization and antimutagenic activity of soybean saponins. Mutat Res 448:11–22PubMedCrossRef Berhow MA, Wagner ED, Vaughn SF, Plewa MJ (2000) Characterization and antimutagenic activity of soybean saponins. Mutat Res 448:11–22PubMedCrossRef
Zurück zum Zitat Berhow MA, Duval SM, Dobbins TA, Maynes J (2002) Analysis and quantitative determination of group B saponins in processed soybean products. Phytochem Anal 13:343–348PubMedCrossRef Berhow MA, Duval SM, Dobbins TA, Maynes J (2002) Analysis and quantitative determination of group B saponins in processed soybean products. Phytochem Anal 13:343–348PubMedCrossRef
Zurück zum Zitat Challinor VL, De Voss JJ (2013) Open-chain steroidal glycosides, a diverse class of plant saponins. Nat Prod Rep 30:429–454PubMedCrossRef Challinor VL, De Voss JJ (2013) Open-chain steroidal glycosides, a diverse class of plant saponins. Nat Prod Rep 30:429–454PubMedCrossRef
Zurück zum Zitat Chen JT, Li HZ, Wang D, Zhang YJ, Yang CR (2006) New dammarane monodesmosides from the acidic deglycosylation of notoginseng-leaf saponins. Helv Chim Acta 89:1442–1448CrossRef Chen JT, Li HZ, Wang D, Zhang YJ, Yang CR (2006) New dammarane monodesmosides from the acidic deglycosylation of notoginseng-leaf saponins. Helv Chim Acta 89:1442–1448CrossRef
Zurück zum Zitat Chen J, Zhao R, Zeng YM, Meng H, Zuo WJ, Li X, Wang JH (2009) Three new triterpenoid saponins from the leaves and stems of Panax quinquefolium. J Asian Nat Prod Res 11:195–201PubMedCrossRef Chen J, Zhao R, Zeng YM, Meng H, Zuo WJ, Li X, Wang JH (2009) Three new triterpenoid saponins from the leaves and stems of Panax quinquefolium. J Asian Nat Prod Res 11:195–201PubMedCrossRef
Zurück zum Zitat Cheng S-B, Wang Y, Zhang Y-F et al (2013) Steroidal saponins from Allii macrostemonis bulbs. Chin Tradit Herb Drug 44:1078–1081 Cheng S-B, Wang Y, Zhang Y-F et al (2013) Steroidal saponins from Allii macrostemonis bulbs. Chin Tradit Herb Drug 44:1078–1081
Zurück zum Zitat Cibulski SP, Mourglia-Ettlin G, Teixeira TF, Quirici L, Roehe PM, Ferreira F, Silveira F (2016) Novel ISCOMs from Quillaja brasiliensis saponins induce mucosal and systemic antibody production, T-cell responses and improved antigen uptake. Vaccine 34:1162–1171PubMedCrossRef Cibulski SP, Mourglia-Ettlin G, Teixeira TF, Quirici L, Roehe PM, Ferreira F, Silveira F (2016) Novel ISCOMs from Quillaja brasiliensis saponins induce mucosal and systemic antibody production, T-cell responses and improved antigen uptake. Vaccine 34:1162–1171PubMedCrossRef
Zurück zum Zitat Cui XM, Jiang ZY, Zeng J, Zhou JM, Chen JJ, Zhang XM, Xu LS, Wang Q (2008) Two new dammarane triterpene glycosides from the rhizomes of Panax notoginseng. J Asian Nat Prod Res 10:845–849PubMedCrossRef Cui XM, Jiang ZY, Zeng J, Zhou JM, Chen JJ, Zhang XM, Xu LS, Wang Q (2008) Two new dammarane triterpene glycosides from the rhizomes of Panax notoginseng. J Asian Nat Prod Res 10:845–849PubMedCrossRef
Zurück zum Zitat de Costa F, Yendo AC, Cibulski SP, Fleck JD, Roehe PM, Spilki FR, Gosmann G, Fett-Neto AG (2016) Alternative inactivated poliovirus vaccines adjuvanted with Quillaja brasiliensis or Quil-a saponins are equally effective in inducing specific immune responses. PLoS One 9:e105374CrossRef de Costa F, Yendo AC, Cibulski SP, Fleck JD, Roehe PM, Spilki FR, Gosmann G, Fett-Neto AG (2016) Alternative inactivated poliovirus vaccines adjuvanted with Quillaja brasiliensis or Quil-a saponins are equally effective in inducing specific immune responses. PLoS One 9:e105374CrossRef
Zurück zum Zitat de Faria JT, de Oliveira EB, Minim VPR, Minim LA (2017) Performance of Quillaja bark saponin and β-lactoglobulin mixtures on emulsion formation and stability. Food Hydrocoll 67:178–188CrossRef de Faria JT, de Oliveira EB, Minim VPR, Minim LA (2017) Performance of Quillaja bark saponin and β-lactoglobulin mixtures on emulsion formation and stability. Food Hydrocoll 67:178–188CrossRef
Zurück zum Zitat Dixit V, Tewari J, Obendorf SK (2010) Fungal growth inhibition of regenerated cellulose nanofibrous membranes containing Quillaja saponin. Arch Environ Contam Toxicol 59:417–423PubMedCrossRef Dixit V, Tewari J, Obendorf SK (2010) Fungal growth inhibition of regenerated cellulose nanofibrous membranes containing Quillaja saponin. Arch Environ Contam Toxicol 59:417–423PubMedCrossRef
Zurück zum Zitat Dou DQ, Chen YJ, Liang LH, Pang FG, Shimizu N, Takeda T (2001) Six new dammarane-type triterpene saponins from the leaves of Panax ginseng. Chem Pharm Bull (Tokyo) 49:442–446CrossRef Dou DQ, Chen YJ, Liang LH, Pang FG, Shimizu N, Takeda T (2001) Six new dammarane-type triterpene saponins from the leaves of Panax ginseng. Chem Pharm Bull (Tokyo) 49:442–446CrossRef
Zurück zum Zitat Fattorusso E, Lanzotti V, Taglialatela-Scafati O, Di Rosa M, Lanaro A (2000) Cytotoxicsaponins from bulbs of Allium porrum L. J Agric Food Chem 48:3455–3462PubMedCrossRef Fattorusso E, Lanzotti V, Taglialatela-Scafati O, Di Rosa M, Lanaro A (2000) Cytotoxicsaponins from bulbs of Allium porrum L. J Agric Food Chem 48:3455–3462PubMedCrossRef
Zurück zum Zitat Fattorusso E, Iorizzi M, Lanzotti V (2002) Chemical composition of shallot (Allium ascalonicum Hort.). J Agric Food Chem 50(20):5686–5690PubMedCrossRef Fattorusso E, Iorizzi M, Lanzotti V (2002) Chemical composition of shallot (Allium ascalonicum Hort.). J Agric Food Chem 50(20):5686–5690PubMedCrossRef
Zurück zum Zitat Fleck JD, Kauffmann C, Spilki F, Lencina CL, Roehe PM, Gosmann G (2006) Adjuvant activity of Quillaja brasiliensis saponins on the immune responses to bovine herpesvirus type 1 in mice. Vaccine 24:7129–7134PubMedCrossRef Fleck JD, Kauffmann C, Spilki F, Lencina CL, Roehe PM, Gosmann G (2006) Adjuvant activity of Quillaja brasiliensis saponins on the immune responses to bovine herpesvirus type 1 in mice. Vaccine 24:7129–7134PubMedCrossRef
Zurück zum Zitat Fleck JD, Betti AH, da Silva FP, Troian EA, Olivaro C, Ferreira F, Verza SG (2019) Saponins from Quillaja saponaria and Quillaja brasiliensis: particular chemical characteristics and biological activities. Molecules 24:171PubMedCentralCrossRef Fleck JD, Betti AH, da Silva FP, Troian EA, Olivaro C, Ferreira F, Verza SG (2019) Saponins from Quillaja saponaria and Quillaja brasiliensis: particular chemical characteristics and biological activities. Molecules 24:171PubMedCentralCrossRef
Zurück zum Zitat Güçlü-Ustündağ O, Mazza G (2007) Saponins: properties, applications and processing. Crit Rev Food Sci Nutr 47:231–258PubMedCrossRef Güçlü-Ustündağ O, Mazza G (2007) Saponins: properties, applications and processing. Crit Rev Food Sci Nutr 47:231–258PubMedCrossRef
Zurück zum Zitat Guo S, Kenne L (2000) Structural studies of triterpenoid saponins with new acyl components from Quillaja saponaria Molina. Phytochemistry 55:419–428PubMedCrossRef Guo S, Kenne L (2000) Structural studies of triterpenoid saponins with new acyl components from Quillaja saponaria Molina. Phytochemistry 55:419–428PubMedCrossRef
Zurück zum Zitat Guo S, Lennart K, Lundgren LN, Rönnberg B, Sundquist BG (1998) Triterpenoid saponins from Quillaja saponaria. Phytochemistry 48:175–180PubMedCrossRef Guo S, Lennart K, Lundgren LN, Rönnberg B, Sundquist BG (1998) Triterpenoid saponins from Quillaja saponaria. Phytochemistry 48:175–180PubMedCrossRef
Zurück zum Zitat Han JY, Kwon YS, Yang DC, Jung YR, Choi YE (2006) Expression and RNA interference-induced silencing of the dammarenediol synthase gene in Panax ginseng. Plant Cell Physiol 47:1653–1662PubMedCrossRef Han JY, Kwon YS, Yang DC, Jung YR, Choi YE (2006) Expression and RNA interference-induced silencing of the dammarenediol synthase gene in Panax ginseng. Plant Cell Physiol 47:1653–1662PubMedCrossRef
Zurück zum Zitat Haralampidis K, Trojanowska M, Osbourn AE (2002) Biosynthesis of triterpenoid saponins in plants. In: Dutta NN et al (eds) History and trends in bioprocessing and biotransformation. Advances in biochemical engineering/biotechnology, vol 75. Springer, Berlin, Heidelberg, pp 31–49 Haralampidis K, Trojanowska M, Osbourn AE (2002) Biosynthesis of triterpenoid saponins in plants. In: Dutta NN et al (eds) History and trends in bioprocessing and biotransformation. Advances in biochemical engineering/biotechnology, vol 75. Springer, Berlin, Heidelberg, pp 31–49
Zurück zum Zitat Higuchi R, Tokimitsu Y, Komori T (1988) An acylated triterpenoid saponin from Quillaja saponaria. Phytochemistry 27:1165–1168CrossRef Higuchi R, Tokimitsu Y, Komori T (1988) An acylated triterpenoid saponin from Quillaja saponaria. Phytochemistry 27:1165–1168CrossRef
Zurück zum Zitat Holtshausen L, Chaves AV, Beauchemin KA, McGinn SM, McAllister TA, Odongo NE, Cheeke PR, Benchaar C (2009) Feeding saponin-containing Yucca schidigera and Quillaja saponaria to decrease enteric methane production in dairy cows. J Dairy Sci 92:2809–2821PubMedCrossRef Holtshausen L, Chaves AV, Beauchemin KA, McGinn SM, McAllister TA, Odongo NE, Cheeke PR, Benchaar C (2009) Feeding saponin-containing Yucca schidigera and Quillaja saponaria to decrease enteric methane production in dairy cows. J Dairy Sci 92:2809–2821PubMedCrossRef
Zurück zum Zitat Hong HD, Choi SY, Kim YC, Lee YC, Cho CW (2009) Rapid determination of ginsenosides Rb 1, Rf, and Rg 1 in Korean ginseng using HPLC. J Ginseng Res 33:8–12CrossRef Hong HD, Choi SY, Kim YC, Lee YC, Cho CW (2009) Rapid determination of ginsenosides Rb 1, Rf, and Rg 1 in Korean ginseng using HPLC. J Ginseng Res 33:8–12CrossRef
Zurück zum Zitat Jacobsen NE, Fairbrother WJ, Kensil CR, Lim A, Wheeler DA, Powell MF (1996) Carbohydr Res 280:1–14PubMedCrossRef Jacobsen NE, Fairbrother WJ, Kensil CR, Lim A, Wheeler DA, Powell MF (1996) Carbohydr Res 280:1–14PubMedCrossRef
Zurück zum Zitat Jegal J, Jeong EJ, Yang MH (2019) A review of the different methods applied in ginsenoside extraction from Panax ginseng and Panax quinquefolius roots. Nat Product Commun 14:1–10 Jegal J, Jeong EJ, Yang MH (2019) A review of the different methods applied in ginsenoside extraction from Panax ginseng and Panax quinquefolius roots. Nat Product Commun 14:1–10
Zurück zum Zitat Jiang HP, Qiu YK, Cheng DR, Kang TG, Dou DQ (2008) Structure elucidation and complete NMR spectral assignments of two new dammarane-type tetraglycosides from Panax quinquefolium. Magn Reson Chem 46:786–790PubMedCrossRef Jiang HP, Qiu YK, Cheng DR, Kang TG, Dou DQ (2008) Structure elucidation and complete NMR spectral assignments of two new dammarane-type tetraglycosides from Panax quinquefolium. Magn Reson Chem 46:786–790PubMedCrossRef
Zurück zum Zitat Kahn RA, Durst F (2000) Function and evolution of plant cytochrome P450. Recent Adv Phytochem 34:151–189CrossRef Kahn RA, Durst F (2000) Function and evolution of plant cytochrome P450. Recent Adv Phytochem 34:151–189CrossRef
Zurück zum Zitat Kaku T, Miyata T, Uruno T, Sako I, Kinoshita A (1975) Chemico-pharmacological studies on Saponins of Panax Ginseng C. A. Meyer. I. Chemical part. Arzneimittelforschung 25:343–347PubMed Kaku T, Miyata T, Uruno T, Sako I, Kinoshita A (1975) Chemico-pharmacological studies on Saponins of Panax Ginseng C. A. Meyer. I. Chemical part. Arzneimittelforschung 25:343–347PubMed
Zurück zum Zitat Kato S, Yumoto S, Takada Y, Kono Y, Shimada S, Sakai T, Shimada H, Takahashi K, Adachi T, Tabuchi K, Kikuchi A (2007) A new soybean cultivar ‘Kinusayaka’ lacking three lipoxygenaseisozymes and group a acetyl saponin. Bull Natl Agric Res Cent Tohoku Reg 107:29–42 Kato S, Yumoto S, Takada Y, Kono Y, Shimada S, Sakai T, Shimada H, Takahashi K, Adachi T, Tabuchi K, Kikuchi A (2007) A new soybean cultivar ‘Kinusayaka’ lacking three lipoxygenaseisozymes and group a acetyl saponin. Bull Natl Agric Res Cent Tohoku Reg 107:29–42
Zurück zum Zitat Kereselidze EV, Pkheidze TA, Kemertelidze EP (1970) Diosgenin from Allium albidum. Khim Prir Soedin 6(3):378 Kereselidze EV, Pkheidze TA, Kemertelidze EP (1970) Diosgenin from Allium albidum. Khim Prir Soedin 6(3):378
Zurück zum Zitat Khristulas FS, Gorovits MB, Luchanskaya VN et al (1970) A new steroid sapogenin from Alliumgiganteum. Khim Prir Soedin 6:489 Khristulas FS, Gorovits MB, Luchanskaya VN et al (1970) A new steroid sapogenin from Alliumgiganteum. Khim Prir Soedin 6:489
Zurück zum Zitat Kikuchi A, Tsukamoto C, Tabuchi K, Adachi T, Okubo K (1999) Inheritance and characterization of a null allele for group Aacetyl saponins found in a mutant soybean (Glycine max (L.) Merrill). Breed Sci 49:167–171CrossRef Kikuchi A, Tsukamoto C, Tabuchi K, Adachi T, Okubo K (1999) Inheritance and characterization of a null allele for group Aacetyl saponins found in a mutant soybean (Glycine max (L.) Merrill). Breed Sci 49:167–171CrossRef
Zurück zum Zitat Kim Y-J, Lee OR, Oh JY, Jang M-G, Yang D-C (2014) Functional analysis of 3-hydroxy-3-methylglutaryl coenzyme a reductase encoding genes in triterpene saponin-producing ginseng. Plant Physiol 165:373–387PubMedPubMedCentralCrossRef Kim Y-J, Lee OR, Oh JY, Jang M-G, Yang D-C (2014) Functional analysis of 3-hydroxy-3-methylglutaryl coenzyme a reductase encoding genes in triterpene saponin-producing ginseng. Plant Physiol 165:373–387PubMedPubMedCentralCrossRef
Zurück zum Zitat Kitagawa I, Wang HK, Taniyama T, Yoshikawa AM (1998) Saponin and sapogenol A, soy sapogenol B, and soy sapogenol E oleanene sapogenols from soybean Glycine max. Structures of soy saponin I, soy saponin II, and soy saponin III. Chem Pharm Bull 36:153–161CrossRef Kitagawa I, Wang HK, Taniyama T, Yoshikawa AM (1998) Saponin and sapogenol A, soy sapogenol B, and soy sapogenol E oleanene sapogenols from soybean Glycine max. Structures of soy saponin I, soy saponin II, and soy saponin III. Chem Pharm Bull 36:153–161CrossRef
Zurück zum Zitat Kite GC, Howes MJ, Simmonds MS (2004) Metabolomic analysis of saponins in crude extracts of Quillaja saponaria by liquid chromatography/mass spectrometry for product authentication. Rapid Commun Mass Spect 18:2859–2870CrossRef Kite GC, Howes MJ, Simmonds MS (2004) Metabolomic analysis of saponins in crude extracts of Quillaja saponaria by liquid chromatography/mass spectrometry for product authentication. Rapid Commun Mass Spect 18:2859–2870CrossRef
Zurück zum Zitat Kochan E, Szymańska G, Wielanek M, Wiktorowska-Owczarek A, Jóźwiak-Bębenista M, Grzegorczyk-Karolak I (2019) The content of triterpene saponins and phenolic compounds in American ginseng hairy root extracts and their antioxidant and cytotoxic properties. Plant Cell Tissue Org Cult 138:353–362CrossRef Kochan E, Szymańska G, Wielanek M, Wiktorowska-Owczarek A, Jóźwiak-Bębenista M, Grzegorczyk-Karolak I (2019) The content of triterpene saponins and phenolic compounds in American ginseng hairy root extracts and their antioxidant and cytotoxic properties. Plant Cell Tissue Org Cult 138:353–362CrossRef
Zurück zum Zitat Komakine N, Okasaka M, Takaishi Y, Kawazoe K, Murakami K, Yamada Y (2006) New dammarane-type saponin from roots of Panax notoginseng. J Nat Med 60:137CrossRef Komakine N, Okasaka M, Takaishi Y, Kawazoe K, Murakami K, Yamada Y (2006) New dammarane-type saponin from roots of Panax notoginseng. J Nat Med 60:137CrossRef
Zurück zum Zitat Kravets SD, Vollerner YS, Gorovits MB et al (1990) Steroids of the spirostan and furostan series from plants of the genus Allium. Chem Nat Comp 26:359–373CrossRef Kravets SD, Vollerner YS, Gorovits MB et al (1990) Steroids of the spirostan and furostan series from plants of the genus Allium. Chem Nat Comp 26:359–373CrossRef
Zurück zum Zitat Kushiro T, Ebizuka Y (2010) Triterpenes. In: Mander L, Liu HWB (eds) Comprehensive natural products II: chemistry and biology, vol 1. Elsevier, Oxford, pp 673–708CrossRef Kushiro T, Ebizuka Y (2010) Triterpenes. In: Mander L, Liu HWB (eds) Comprehensive natural products II: chemistry and biology, vol 1. Elsevier, Oxford, pp 673–708CrossRef
Zurück zum Zitat Kushiro T, Ohno Y, Shibuya M, Ebizuka Y (1997) In vitro conversion of 2,3-oxidosqualene into dammarenediol by Panax ginseng microsomes. Biol Pharm Bull 20:292–294PubMedCrossRef Kushiro T, Ohno Y, Shibuya M, Ebizuka Y (1997) In vitro conversion of 2,3-oxidosqualene into dammarenediol by Panax ginseng microsomes. Biol Pharm Bull 20:292–294PubMedCrossRef
Zurück zum Zitat Kuzina V, Ekstrøm CT, Andersen SB, Nielsen JK, Olsen CE, Bak S (2009) Identification of defense compounds in Barbarea vulgaris against the herbivore Phyllotreta nemorum by an ecometabolomic approach. Plant Physiol 151:1977–1990PubMedPubMedCentralCrossRef Kuzina V, Ekstrøm CT, Andersen SB, Nielsen JK, Olsen CE, Bak S (2009) Identification of defense compounds in Barbarea vulgaris against the herbivore Phyllotreta nemorum by an ecometabolomic approach. Plant Physiol 151:1977–1990PubMedPubMedCentralCrossRef
Zurück zum Zitat Kwon HW (2019) Inhibitory effects of ginsenoside Ro on clot retraction through suppressing PI3K/Akt signaling pathway in human platelets. Prev Nutr Food Sci 24:56–63PubMedPubMedCentralCrossRef Kwon HW (2019) Inhibitory effects of ginsenoside Ro on clot retraction through suppressing PI3K/Akt signaling pathway in human platelets. Prev Nutr Food Sci 24:56–63PubMedPubMedCentralCrossRef
Zurück zum Zitat Lanzotti V (2005) Bioactive saponins from Allium and Aster plants. Phytochem Rev 4:95–110CrossRef Lanzotti V (2005) Bioactive saponins from Allium and Aster plants. Phytochem Rev 4:95–110CrossRef
Zurück zum Zitat Lanzotti V (2012) Bioactive polar natural compounds from garlic and onions. Phytochem Rev 11:179–196CrossRef Lanzotti V (2012) Bioactive polar natural compounds from garlic and onions. Phytochem Rev 11:179–196CrossRef
Zurück zum Zitat Lee M, Shon HJ, Choi CS, Hung TM, Min BS, Bae K (2009) Ginsenosides from heat processed ginseng. Chem Pharm Bull 57:92–94CrossRef Lee M, Shon HJ, Choi CS, Hung TM, Min BS, Bae K (2009) Ginsenosides from heat processed ginseng. Chem Pharm Bull 57:92–94CrossRef
Zurück zum Zitat Lee MH, Han JY, Kim HJ, Kim YS, Huh GH, Choi YE (2011) Dammarenediol-II production confers TMV tolerance in transgenic tobacco expressing Panax ginseng dammarenediol-II synthase. Plant Cell Physiol 53:173–182PubMedCrossRef Lee MH, Han JY, Kim HJ, Kim YS, Huh GH, Choi YE (2011) Dammarenediol-II production confers TMV tolerance in transgenic tobacco expressing Panax ginseng dammarenediol-II synthase. Plant Cell Physiol 53:173–182PubMedCrossRef
Zurück zum Zitat Lee DG, Lee J, Cho IH, Kim H-J, Lee S-W, Kim Y-O, Park C-G, Lee S (2017) Ginsenoside Rg12, a new dammarane-type triterpene saponin from Panax ginseng root. J Ginseng Res 41:531–533PubMedCrossRef Lee DG, Lee J, Cho IH, Kim H-J, Lee S-W, Kim Y-O, Park C-G, Lee S (2017) Ginsenoside Rg12, a new dammarane-type triterpene saponin from Panax ginseng root. J Ginseng Res 41:531–533PubMedCrossRef
Zurück zum Zitat Leshem Y, Levin I (1978) The effect of growing alfalfa on subsequent cotton plant development and on nitrate formation in peat soil. Plant Soil 50:323–328CrossRef Leshem Y, Levin I (1978) The effect of growing alfalfa on subsequent cotton plant development and on nitrate formation in peat soil. Plant Soil 50:323–328CrossRef
Zurück zum Zitat Li HZ, Teng RW, Yang CR (2001) A novel hexanordammarane glycoside from the roots of Panax nontoginseng. Chin Chem Lett 12:59–62 Li HZ, Teng RW, Yang CR (2001) A novel hexanordammarane glycoside from the roots of Panax nontoginseng. Chin Chem Lett 12:59–62
Zurück zum Zitat Li GY, Zeng YM, Meng H, Li X, Wang JH (2009) A new triterpenoid saponin from the leaves and stems of Panax quinquefolium L. Chin Chem Lett 20:1207–1210CrossRef Li GY, Zeng YM, Meng H, Li X, Wang JH (2009) A new triterpenoid saponin from the leaves and stems of Panax quinquefolium L. Chin Chem Lett 20:1207–1210CrossRef
Zurück zum Zitat Liao PY, Wang D, Zhang YJ, Yang CR (2008) Dammarane-type glycosides from steamed notogensing. J Agric Food 56:1751–1756CrossRef Liao PY, Wang D, Zhang YJ, Yang CR (2008) Dammarane-type glycosides from steamed notogensing. J Agric Food 56:1751–1756CrossRef
Zurück zum Zitat Lu JM, Jiang J, Jamaluddin MS, Liang Z, Yao Q, Chen C (2019) Ginsenoside Rb1 blocks ritonavir-induced oxidative stress and ENOS downregulation through activation of estrogen receptor-beta and upregulation of SOD in human endothelial cells. Int J Mol Sci 20:294PubMedCentralCrossRef Lu JM, Jiang J, Jamaluddin MS, Liang Z, Yao Q, Chen C (2019) Ginsenoside Rb1 blocks ritonavir-induced oxidative stress and ENOS downregulation through activation of estrogen receptor-beta and upregulation of SOD in human endothelial cells. Int J Mol Sci 20:294PubMedCentralCrossRef
Zurück zum Zitat Luo HM, Sun C, Sun YZ, Wu Q, Li Y, Song JY, Niu YY, Cheng X, Xu HX, Li CY et al (2011) Analysis of the transcriptome of Panax notoginseng root uncovers putative triterpene saponin–biosynthetic genes and genetic markers. BMC Genome 12:S5CrossRef Luo HM, Sun C, Sun YZ, Wu Q, Li Y, Song JY, Niu YY, Cheng X, Xu HX, Li CY et al (2011) Analysis of the transcriptome of Panax notoginseng root uncovers putative triterpene saponin–biosynthetic genes and genetic markers. BMC Genome 12:S5CrossRef
Zurück zum Zitat MacDonald RS, Guo JY, Copeland J, Browning JD, Sleper JD, Rottinghaus GE, Berhow MA (2005) Environmental influences on isoflavones and saponins in soybeans and their role in colon cancer. J Nutr 135:1239–1242PubMedCrossRef MacDonald RS, Guo JY, Copeland J, Browning JD, Sleper JD, Rottinghaus GE, Berhow MA (2005) Environmental influences on isoflavones and saponins in soybeans and their role in colon cancer. J Nutr 135:1239–1242PubMedCrossRef
Zurück zum Zitat Maier C, Conrad J, Carle R, Weiss J, Schweiggert RM (2015) Phenolic constituents in commercial aqueous Quillaja (Quillaja saponaria Molina) wood extracts. J Agric Food Chem 63:1756–1762PubMedCrossRef Maier C, Conrad J, Carle R, Weiss J, Schweiggert RM (2015) Phenolic constituents in commercial aqueous Quillaja (Quillaja saponaria Molina) wood extracts. J Agric Food Chem 63:1756–1762PubMedCrossRef
Zurück zum Zitat Mohanan P, Subramaniyam S, Mathiyalagan R, Yang DC (2018) Molecular signaling of Ginsenosides Rb1, Rg1, and Rg3 and their mode of actions. J Ginseng Res 42:123–132PubMedCrossRef Mohanan P, Subramaniyam S, Mathiyalagan R, Yang DC (2018) Molecular signaling of Ginsenosides Rb1, Rg1, and Rg3 and their mode of actions. J Ginseng Res 42:123–132PubMedCrossRef
Zurück zum Zitat Moses T, Papadopoulou KK, Osbourn A (2014) Metabolic and functional diversity of saponins, biosynthetic intermediates and semi-synthetic derivatives. Crit Rev Biochem Mol Biol 49:439–462PubMedPubMedCentralCrossRef Moses T, Papadopoulou KK, Osbourn A (2014) Metabolic and functional diversity of saponins, biosynthetic intermediates and semi-synthetic derivatives. Crit Rev Biochem Mol Biol 49:439–462PubMedPubMedCentralCrossRef
Zurück zum Zitat Mostafa A, Jogaiah S, El-Sayed M, Ito S-I et al (2013a) Aginoside saponin, a potent antifungal compound, and secondary metabolite analyses from Allium nigrum L. Phytochem Lett 6:274–280CrossRef Mostafa A, Jogaiah S, El-Sayed M, Ito S-I et al (2013a) Aginoside saponin, a potent antifungal compound, and secondary metabolite analyses from Allium nigrum L. Phytochem Lett 6:274–280CrossRef
Zurück zum Zitat Mostafa A, Sudisha J, El-Sayed M, Ito S-I, Ikeda T, Yamauchi N, Shigyo M (2013b) Aginoside saponin, a potent antifungal compound, and secondary metabolite analyses from Allium nigrum L. Phytochem Lett 6:274–280CrossRef Mostafa A, Sudisha J, El-Sayed M, Ito S-I, Ikeda T, Yamauchi N, Shigyo M (2013b) Aginoside saponin, a potent antifungal compound, and secondary metabolite analyses from Allium nigrum L. Phytochem Lett 6:274–280CrossRef
Zurück zum Zitat Nakamura S, Sugimoto S, Matsuda H, Yoshikawa M (2007a) Medicinal flowers. XVII. New dammarane-type triterpene glycosides from flower buds of American ginseng, Panax quinquefolium L. Chem Pharm Bull (Tokyo) 55:1342–1348CrossRef Nakamura S, Sugimoto S, Matsuda H, Yoshikawa M (2007a) Medicinal flowers. XVII. New dammarane-type triterpene glycosides from flower buds of American ginseng, Panax quinquefolium L. Chem Pharm Bull (Tokyo) 55:1342–1348CrossRef
Zurück zum Zitat Nakamura S, Sugimoto S, Matsuda H, Yoshikawa M (2007b) Structures of dammarane-type triterpene triglycosides from the flower buds of Panax ginseng. Heterocycles 71:577–588CrossRef Nakamura S, Sugimoto S, Matsuda H, Yoshikawa M (2007b) Structures of dammarane-type triterpene triglycosides from the flower buds of Panax ginseng. Heterocycles 71:577–588CrossRef
Zurück zum Zitat Nguyen HT, Song GY, Kang HK, Kim YH (2010a) New dammarane saponins from the steamed ginseng leaves. Bull Kor Chem Soc 31:2094–2096CrossRef Nguyen HT, Song GY, Kang HK, Kim YH (2010a) New dammarane saponins from the steamed ginseng leaves. Bull Kor Chem Soc 31:2094–2096CrossRef
Zurück zum Zitat Nguyen HT, Song GY, Kim JA, Hyun JH, Kang HK, Kim YH (2010b) Dammarane-type saponins from the flower buds of Panax ginseng and their effects on human leukemia cells. Bioorg Med Chem Lett 20:309–314PubMedCrossRef Nguyen HT, Song GY, Kim JA, Hyun JH, Kang HK, Kim YH (2010b) Dammarane-type saponins from the flower buds of Panax ginseng and their effects on human leukemia cells. Bioorg Med Chem Lett 20:309–314PubMedCrossRef
Zurück zum Zitat Niu YY, Luo HM, Sun C, Yang T-J, Dong L, Huang LF, Chen SL (2014) Expression profiling of the triterpene saponin biosynthesis genes FPS, SS, SE, and DS in the medicinal plant Panax notoginseng. Gene 533:295–303PubMedCrossRef Niu YY, Luo HM, Sun C, Yang T-J, Dong L, Huang LF, Chen SL (2014) Expression profiling of the triterpene saponin biosynthesis genes FPS, SS, SE, and DS in the medicinal plant Panax notoginseng. Gene 533:295–303PubMedCrossRef
Zurück zum Zitat Nord LI, Kenne L (2000) Novel acetylated triterpenoid saponins in a chromatographic fraction from Quillaja saponaria Molina. Carbohydr Res 329:817–829PubMedCrossRef Nord LI, Kenne L (2000) Novel acetylated triterpenoid saponins in a chromatographic fraction from Quillaja saponaria Molina. Carbohydr Res 329:817–829PubMedCrossRef
Zurück zum Zitat Nyberg NT, Baumann H, Kenne L (2003) Solid-phase extraction NMR studies of chromatographic fractions of saponins from Quillaja saponaria. Anal Chem 75:268–274PubMedCrossRef Nyberg NT, Baumann H, Kenne L (2003) Solid-phase extraction NMR studies of chromatographic fractions of saponins from Quillaja saponaria. Anal Chem 75:268–274PubMedCrossRef
Zurück zum Zitat Okubo K, Iijima M, Kobayashi Y, Yoshikoshi M, Uchida T, Kudou S (1992) Components responsible for the undesirable taste of soybean seeds. Biosci Biotechnol Biochem 56:99–103CrossRef Okubo K, Iijima M, Kobayashi Y, Yoshikoshi M, Uchida T, Kudou S (1992) Components responsible for the undesirable taste of soybean seeds. Biosci Biotechnol Biochem 56:99–103CrossRef
Zurück zum Zitat Oleszek W (1993) Allelopathic potentials of alfalfa (Medicago sativa) saponins: their relation to antifungal and hemolytic activities. J Chem Ecol 19:1063–1074PubMedCrossRef Oleszek W (1993) Allelopathic potentials of alfalfa (Medicago sativa) saponins: their relation to antifungal and hemolytic activities. J Chem Ecol 19:1063–1074PubMedCrossRef
Zurück zum Zitat Panneerselvam K, Tsukamoto C, Honda N et al (2013) Saponin polymorphism in the Korean wild soybean (Glycine soja Sieb. and Zucc.). Plant Breed 132:121–126CrossRef Panneerselvam K, Tsukamoto C, Honda N et al (2013) Saponin polymorphism in the Korean wild soybean (Glycine soja Sieb. and Zucc.). Plant Breed 132:121–126CrossRef
Zurück zum Zitat Parente JP, Da Silva BP (2009) Bioactive complex triterpenoid saponins from the Leguminosae family. Nat Prod Commun 4:143–155PubMed Parente JP, Da Silva BP (2009) Bioactive complex triterpenoid saponins from the Leguminosae family. Nat Prod Commun 4:143–155PubMed
Zurück zum Zitat Park IH, Han SB, Kim JM, Piao LZ, Kwon SW, Kim NY, Kang TL, Park MK, Park JH (2002a) Four new acetylated ginsenosides from processed ginseng (sun ginseng). Arch Pharm Res 25:837–841PubMedCrossRef Park IH, Han SB, Kim JM, Piao LZ, Kwon SW, Kim NY, Kang TL, Park MK, Park JH (2002a) Four new acetylated ginsenosides from processed ginseng (sun ginseng). Arch Pharm Res 25:837–841PubMedCrossRef
Zurück zum Zitat Park IH, Kim NY, Han SB, Kim JM, Kwon SW, Kim HJ, Park MK, Park JH (2002b) Three new dammarane glycosides from heat processed ginseng. Arch Pharm Res 25:428–432PubMedCrossRef Park IH, Kim NY, Han SB, Kim JM, Kwon SW, Kim HJ, Park MK, Park JH (2002b) Three new dammarane glycosides from heat processed ginseng. Arch Pharm Res 25:428–432PubMedCrossRef
Zurück zum Zitat Patel SS, Savjani JK (2015) Systematic review of plant steroids as potential anti-inflammatory agents: current status and future perspectives. Phytopharmacology 4:121–125 Patel SS, Savjani JK (2015) Systematic review of plant steroids as potential anti-inflammatory agents: current status and future perspectives. Phytopharmacology 4:121–125
Zurück zum Zitat Pen B, Sar C, Mwenya B, Kuwaki K, Morikawa R, Takahashi J (2006) Effects of Yucca schidigera and Quillaja saponaria extracts on in vitro ruminal fermentation and methane emission. Anim Feed Sci Technol 129:175–186CrossRef Pen B, Sar C, Mwenya B, Kuwaki K, Morikawa R, Takahashi J (2006) Effects of Yucca schidigera and Quillaja saponaria extracts on in vitro ruminal fermentation and methane emission. Anim Feed Sci Technol 129:175–186CrossRef
Zurück zum Zitat Qiu F, Ma ZZ, Xu SX, Yao XS, Che CT, Chen YJ (2001) A pair of 24-hydroperoxyl epimeric dammarane saponins from flower-buds of Panax ginseng. J Asian Nat Prod Res 3:235–240PubMedCrossRef Qiu F, Ma ZZ, Xu SX, Yao XS, Che CT, Chen YJ (2001) A pair of 24-hydroperoxyl epimeric dammarane saponins from flower-buds of Panax ginseng. J Asian Nat Prod Res 3:235–240PubMedCrossRef
Zurück zum Zitat Reichert CL, Salminen H, Bönisch GB, Schäfer C, Weissa J (2019) Concentration effect of Quillaja saponin - co-surfactant mixtures on emulsifying properties. Colloid Interface Sci 519:71–80CrossRef Reichert CL, Salminen H, Bönisch GB, Schäfer C, Weissa J (2019) Concentration effect of Quillaja saponin - co-surfactant mixtures on emulsifying properties. Colloid Interface Sci 519:71–80CrossRef
Zurück zum Zitat Roner MR, Sprayberry J, Spinks M, Dhanji S (2007) Antiviral activity obtained from aqueous extracts of the Chilean soapbark tree (Quillaja saponaria Molina). J Gen Virol 88:275–285PubMedCrossRef Roner MR, Sprayberry J, Spinks M, Dhanji S (2007) Antiviral activity obtained from aqueous extracts of the Chilean soapbark tree (Quillaja saponaria Molina). J Gen Virol 88:275–285PubMedCrossRef
Zurück zum Zitat Roner MR, Tam KI, Kiesling-Barrager M (2010) Prevention of rotavirus infections in vitro with aqueous extracts of Quillaja Saponaria Molina. Future Med Chem 2:1083–1097PubMedCrossRef Roner MR, Tam KI, Kiesling-Barrager M (2010) Prevention of rotavirus infections in vitro with aqueous extracts of Quillaja Saponaria Molina. Future Med Chem 2:1083–1097PubMedCrossRef
Zurück zum Zitat Sadeghi M, Zolfaghari B, Senatore M, Lanzotti V (2013) Spirostane, furostane and cholestane saponins from Persian leek with antifungal activity. Food Chem 141:1512–1521PubMedCrossRef Sadeghi M, Zolfaghari B, Senatore M, Lanzotti V (2013) Spirostane, furostane and cholestane saponins from Persian leek with antifungal activity. Food Chem 141:1512–1521PubMedCrossRef
Zurück zum Zitat San Martín R, Briones R (1999) Industrial uses and sustainable supply of Quillaja saponaria (Rosaceae) saponins. Econ Bot 53:302–311CrossRef San Martín R, Briones R (1999) Industrial uses and sustainable supply of Quillaja saponaria (Rosaceae) saponins. Econ Bot 53:302–311CrossRef
Zurück zum Zitat Sang S, Mao S, Lao A, Chen Z, Ho CT (2001) Four new steroidal saponins from the seeds of Allium tuberosum. J Agric Food Chem 49:1475–1478PubMedCrossRef Sang S, Mao S, Lao A, Chen Z, Ho CT (2001) Four new steroidal saponins from the seeds of Allium tuberosum. J Agric Food Chem 49:1475–1478PubMedCrossRef
Zurück zum Zitat Sasama H, Takada Y, Ishimoto M, Kitamura K, Tsukamoto C (2010) Estimation of the mutation site of a soyasapogenol A-deficient soybean [Glycine max (L.) Merr.] by LC-MS/MS profile analysis. In: Cadwallader KR, Chang S (eds) Chemistry, texture, and flavor of soy, vol 1059. American Chemical Society, New York, pp 91–102 Sasama H, Takada Y, Ishimoto M, Kitamura K, Tsukamoto C (2010) Estimation of the mutation site of a soyasapogenol A-deficient soybean [Glycine max (L.) Merr.] by LC-MS/MS profile analysis. In: Cadwallader KR, Chang S (eds) Chemistry, texture, and flavor of soy, vol 1059. American Chemical Society, New York, pp 91–102
Zurück zum Zitat Sasama T, Ono E, Takagi K, Takada Y, Horikawa M, Nakamoto Y et al (2012) The Sg-1 glycosyltransferase locus regulates structural diversity of triterpenoid saponins of soybean. Plant Cell 24:2123–2138PubMedPubMedCentralCrossRef Sasama T, Ono E, Takagi K, Takada Y, Horikawa M, Nakamoto Y et al (2012) The Sg-1 glycosyltransferase locus regulates structural diversity of triterpenoid saponins of soybean. Plant Cell 24:2123–2138PubMedPubMedCentralCrossRef
Zurück zum Zitat Shi J, Arunasalam K, Yeung D et al (2004) Saponins from edible legumes: chemistry, processing, and health benefits. J Med Food 7:67–78PubMedCrossRef Shi J, Arunasalam K, Yeung D et al (2004) Saponins from edible legumes: chemistry, processing, and health benefits. J Med Food 7:67–78PubMedCrossRef
Zurück zum Zitat Shi Z-Y, Zeng J-Z, Wong AST (2019) Chemical structures and pharmacological profiles of ginseng saponins. Molecules 24:2443PubMedCentralCrossRef Shi Z-Y, Zeng J-Z, Wong AST (2019) Chemical structures and pharmacological profiles of ginseng saponins. Molecules 24:2443PubMedCentralCrossRef
Zurück zum Zitat Shimoyamada M, Kudou S, Okubo K, Yamauchi F, Harada K (1990) Distribution of saponin constituents in some varieties of soybean plant. Agric Biol Chem 54:77–81 Shimoyamada M, Kudou S, Okubo K, Yamauchi F, Harada K (1990) Distribution of saponin constituents in some varieties of soybean plant. Agric Biol Chem 54:77–81
Zurück zum Zitat Shin KC, Oh DK (2016) Classification of glycosidases that hydrolyze the specific positions and types of sugar moieties in ginsenosides. Crit Rev Biotechnol 36:1036–1049PubMedCrossRef Shin KC, Oh DK (2016) Classification of glycosidases that hydrolyze the specific positions and types of sugar moieties in ginsenosides. Crit Rev Biotechnol 36:1036–1049PubMedCrossRef
Zurück zum Zitat Shiraiwa M, Yamauchi F, Harada K, Okubo K (1990) Inheritance of “group A saponin” in soybean seed. Agric Biol Chem 54:1347–1352 Shiraiwa M, Yamauchi F, Harada K, Okubo K (1990) Inheritance of “group A saponin” in soybean seed. Agric Biol Chem 54:1347–1352
Zurück zum Zitat Shiraiwa S, Harada K, Okubo K (1991a) Composition and content of saponins in soybean seed according to variety, cultivation year and maturity. Agric Biol Chem 55:323–331 Shiraiwa S, Harada K, Okubo K (1991a) Composition and content of saponins in soybean seed according to variety, cultivation year and maturity. Agric Biol Chem 55:323–331
Zurück zum Zitat Shiraiwa M, Harada K, Okubo K (1991b) Composition andstructure of “group B saponin” in soybean seed. Agric Biol Chem 55:911–917PubMed Shiraiwa M, Harada K, Okubo K (1991b) Composition andstructure of “group B saponin” in soybean seed. Agric Biol Chem 55:911–917PubMed
Zurück zum Zitat Sobolewska D, Janeczko Z, Podolak I et al (2009) Densitometric analysis of diosgenin in methanolic extracts of Allium ursinum collected at different times during plant development. J Planar Chromatogr 22:305–307CrossRef Sobolewska D, Janeczko Z, Podolak I et al (2009) Densitometric analysis of diosgenin in methanolic extracts of Allium ursinum collected at different times during plant development. J Planar Chromatogr 22:305–307CrossRef
Zurück zum Zitat Sobolewska D, Michalska K, Podolak I, Grabowska K (2016) Steroidal saponins from the genus Allium. Phytochem Rev 15:1–35PubMedCrossRef Sobolewska D, Michalska K, Podolak I, Grabowska K (2016) Steroidal saponins from the genus Allium. Phytochem Rev 15:1–35PubMedCrossRef
Zurück zum Zitat Sparg SG, Light ME, van Staden J (2004) Biological activities and distribution of plant saponins. J Ethnopharmacol 94:219–243PubMedCrossRef Sparg SG, Light ME, van Staden J (2004) Biological activities and distribution of plant saponins. J Ethnopharmacol 94:219–243PubMedCrossRef
Zurück zum Zitat Sugimoto S, Nakamura S, Matsuda H, Kitagawa N, Yoshikawa M (2009) Chemical constituents from seeds of Panax ginseng: structure of new dammarane-type triterpene ketone, panaxadione, and HPLC comparisons of seeds and flesh. Chem Pharm Bull 57:283–287CrossRef Sugimoto S, Nakamura S, Matsuda H, Kitagawa N, Yoshikawa M (2009) Chemical constituents from seeds of Panax ginseng: structure of new dammarane-type triterpene ketone, panaxadione, and HPLC comparisons of seeds and flesh. Chem Pharm Bull 57:283–287CrossRef
Zurück zum Zitat Szakiel A, Pączkowski C, Henry M (2011) Influence of environmental abiotic factors on the content of saponins in plants. Phytochem Rev 10:471–491CrossRef Szakiel A, Pączkowski C, Henry M (2011) Influence of environmental abiotic factors on the content of saponins in plants. Phytochem Rev 10:471–491CrossRef
Zurück zum Zitat Takada Y, Sayama T, Kikuchi A, Kato S, Tatsuzaki N, Nakamoto Y, Suzuki A, Tsukamoto C, Ishimoto M (2010) Genetic analysis of variation in sugar chain composition atthe C-22 position of group A saponins in soybean, Glycine max (L.). Merrill. Breed Sci 60:3–8CrossRef Takada Y, Sayama T, Kikuchi A, Kato S, Tatsuzaki N, Nakamoto Y, Suzuki A, Tsukamoto C, Ishimoto M (2010) Genetic analysis of variation in sugar chain composition atthe C-22 position of group A saponins in soybean, Glycine max (L.). Merrill. Breed Sci 60:3–8CrossRef
Zurück zum Zitat Takada Y, Tayama I, Sayama T, Sasama H, Sarut M, Kikuchi A, Ishimoto M, Tsukamoto C (2012) Genetic analysis of variations in the sugar chain composition at the C-3 position of soybean seed saponins. Breed Sci 61:639–645PubMedPubMedCentralCrossRef Takada Y, Tayama I, Sayama T, Sasama H, Sarut M, Kikuchi A, Ishimoto M, Tsukamoto C (2012) Genetic analysis of variations in the sugar chain composition at the C-3 position of soybean seed saponins. Breed Sci 61:639–645PubMedPubMedCentralCrossRef
Zurück zum Zitat Tam KI, Roner MR (2011) Characterization of in vivo anti-rotavirus activities of saponin extracts from Quillaja saponaria Molina. Antivir Res 90:231–241PubMedCrossRef Tam KI, Roner MR (2011) Characterization of in vivo anti-rotavirus activities of saponin extracts from Quillaja saponaria Molina. Antivir Res 90:231–241PubMedCrossRef
Zurück zum Zitat Taniyama T, Yoshikawa M, Kitagawa I (1988a) Saponinand sapogenol. XLIV. Soyasaponin composition in soybeans of variousorigins and soyasaponin content in various organs of soybean. Structure of soyasaponin V from soybean hypocotyl. Yakugaku Zasshi 108:562–571PubMedCrossRef Taniyama T, Yoshikawa M, Kitagawa I (1988a) Saponinand sapogenol. XLIV. Soyasaponin composition in soybeans of variousorigins and soyasaponin content in various organs of soybean. Structure of soyasaponin V from soybean hypocotyl. Yakugaku Zasshi 108:562–571PubMedCrossRef
Zurück zum Zitat Taniyama T, Nagahama Y, Yoshikawa M, Kitagawa I (1988b) 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. Chem Pharm Bull (Tokyo) 36:2829–2839CrossRef Taniyama T, Nagahama Y, Yoshikawa M, Kitagawa I (1988b) 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. Chem Pharm Bull (Tokyo) 36:2829–2839CrossRef
Zurück zum Zitat Tansakul P, Shibuya M, Kushiro T, Ebizuka Y (2006) Dammarenediol-II synthase, the first dedicated enzyme for ginsenoside biosynthesis, in Panax ginseng. FEBS Lett 580:5143–5149PubMedCrossRef Tansakul P, Shibuya M, Kushiro T, Ebizuka Y (2006) Dammarenediol-II synthase, the first dedicated enzyme for ginsenoside biosynthesis, in Panax ginseng. FEBS Lett 580:5143–5149PubMedCrossRef
Zurück zum Zitat Teng RW, Ang C, McManus D, Armstrong D, Mau S, Bacic A (2004a) Regioselective acylation of ginsenosides by Novozyme 435 to generate molecular diversity. Helv Chim Acta 87:1860–1872CrossRef Teng RW, Ang C, McManus D, Armstrong D, Mau S, Bacic A (2004a) Regioselective acylation of ginsenosides by Novozyme 435 to generate molecular diversity. Helv Chim Acta 87:1860–1872CrossRef
Zurück zum Zitat Teng RW, Li HZ, Wang DZ, Yang CR (2004b) Hydrolytic reaction of plant extracts to generate molecular diversity: new dammarane glycosides from the mild acid hydrolysate of root saponins of Panax notoginseng. Helv Chim Acta 87:1270–1278CrossRef Teng RW, Li HZ, Wang DZ, Yang CR (2004b) Hydrolytic reaction of plant extracts to generate molecular diversity: new dammarane glycosides from the mild acid hydrolysate of root saponins of Panax notoginseng. Helv Chim Acta 87:1270–1278CrossRef
Zurück zum Zitat Tsukamoto C, Kikuchi A, Harada K et al (1993) Genetic and chemical polymorphisms of saponins in soybean seed. Phytochemistry 34:1351–1356PubMedCrossRef Tsukamoto C, Kikuchi A, Harada K et al (1993) Genetic and chemical polymorphisms of saponins in soybean seed. Phytochemistry 34:1351–1356PubMedCrossRef
Zurück zum Zitat Tsuno Y, Fujimatsu T, Endo K, Sugiyama A, Yazaki K (2018) Soyasaponins: a new class of root exudates in soybean (Glycine max). Plant Cell Physiol 59:366–375PubMedCrossRef Tsuno Y, Fujimatsu T, Endo K, Sugiyama A, Yazaki K (2018) Soyasaponins: a new class of root exudates in soybean (Glycine max). Plant Cell Physiol 59:366–375PubMedCrossRef
Zurück zum Zitat Tung NH, Song GY, Park YJ, Kim YH (2009) Two new dammarane-type saponins from the leaves of Panax ginseng. Chem Pharm Bull (Tokyo) 57:1412–1414CrossRef Tung NH, Song GY, Park YJ, Kim YH (2009) Two new dammarane-type saponins from the leaves of Panax ginseng. Chem Pharm Bull (Tokyo) 57:1412–1414CrossRef
Zurück zum Zitat Tung NH, Song GY, Nhiem NX, Ding Y, Tai BH, Jin LG, Lim CM, Hyun JW, Park CJ, Kang HK, Kim YH (2010) Dammarane-type saponins from the flower buds of Panax ginseng and their intracellular radical scavenging capacity. J Agric Food Chem 58:868–874PubMedCrossRef Tung NH, Song GY, Nhiem NX, Ding Y, Tai BH, Jin LG, Lim CM, Hyun JW, Park CJ, Kang HK, Kim YH (2010) Dammarane-type saponins from the flower buds of Panax ginseng and their intracellular radical scavenging capacity. J Agric Food Chem 58:868–874PubMedCrossRef
Zurück zum Zitat Turner TR, Ramakrishnan K, Walshaw J et al (2013) Comparative meta-transcriptomics reveals kingdom level changes in the rhizosphere microbiome of plants. ISME J 7:2248–2258PubMedPubMedCentralCrossRef Turner TR, Ramakrishnan K, Walshaw J et al (2013) Comparative meta-transcriptomics reveals kingdom level changes in the rhizosphere microbiome of plants. ISME J 7:2248–2258PubMedPubMedCentralCrossRef
Zurück zum Zitat Wang J, Li W, Li X (1998) A new saponin from the leaves and stems of Panax quinquefolium L. collected in Canada. J Asian Nat Prod Res 1:93–97PubMedCrossRef Wang J, Li W, Li X (1998) A new saponin from the leaves and stems of Panax quinquefolium L. collected in Canada. J Asian Nat Prod Res 1:93–97PubMedCrossRef
Zurück zum Zitat Wang JH, Li W, Sha Y, Tezuka Y, Kadota S, Li X (2001a) Triterpenoid saponins from leaves and stems of Panax quinquefolium L. J Asian Nat Prod Res 3:123–130PubMedCrossRef Wang JH, Li W, Sha Y, Tezuka Y, Kadota S, Li X (2001a) Triterpenoid saponins from leaves and stems of Panax quinquefolium L. J Asian Nat Prod Res 3:123–130PubMedCrossRef
Zurück zum Zitat Wang JH, Sha Y, Tezuka Y, Kadota S, Li X (2001b) Quinquenoside L9 from leaves and stems of Panax quinquefolium L. J Asian Nat Prod Res 3:293–297PubMedCrossRef Wang JH, Sha Y, Tezuka Y, Kadota S, Li X (2001b) Quinquenoside L9 from leaves and stems of Panax quinquefolium L. J Asian Nat Prod Res 3:293–297PubMedCrossRef
Zurück zum Zitat Wang XY, Wang D, Ma XX, Zhang Y-J, Yang C-R (2008) Two new dammarane-type bisdesmosides from the fruit pedicels of Panax notoginseng. Helv Chim Acta 91:60–66CrossRef Wang XY, Wang D, Ma XX, Zhang Y-J, Yang C-R (2008) Two new dammarane-type bisdesmosides from the fruit pedicels of Panax notoginseng. Helv Chim Acta 91:60–66CrossRef
Zurück zum Zitat Wang J-R, Yamasaki Y, Tanaka T, Kouno I, Jiang Z-H (2009) Dammarane-type triterpene saponins from the flowers of Panax notoginseng. Molecules 14:2087–2094PubMedPubMedCentralCrossRef Wang J-R, Yamasaki Y, Tanaka T, Kouno I, Jiang Z-H (2009) Dammarane-type triterpene saponins from the flowers of Panax notoginseng. Molecules 14:2087–2094PubMedPubMedCentralCrossRef
Zurück zum Zitat Wojciechowski K (2013) Surface activity of saponin from Quillaja bark at the air/water and oil/water interfaces. Colloids Surf B Biointerfaces 108:95–102PubMedCrossRef Wojciechowski K (2013) Surface activity of saponin from Quillaja bark at the air/water and oil/water interfaces. Colloids Surf B Biointerfaces 108:95–102PubMedCrossRef
Zurück zum Zitat Wong AST, Che CM, Leung KW (2015) Recent advances in ginseng as cancer therapeutics: a functional and mechanistic overview. Nat Prod Rep 32:256–272PubMedCrossRef Wong AST, Che CM, Leung KW (2015) Recent advances in ginseng as cancer therapeutics: a functional and mechanistic overview. Nat Prod Rep 32:256–272PubMedCrossRef
Zurück zum Zitat Wu W, Zhang Q, Zhu Y et al (2008) Comparative metabolic profiling reveals secondary metabolites correlated with soybean salt tolerance. J Agric Food Chem 56:11132–11138PubMedCrossRef Wu W, Zhang Q, Zhu Y et al (2008) Comparative metabolic profiling reveals secondary metabolites correlated with soybean salt tolerance. J Agric Food Chem 56:11132–11138PubMedCrossRef
Zurück zum Zitat Xu J, Chu Y, Liao B, Xiao S, Yin Q, Bai R, Su H, Dong L, Li X, Qian J et al (2017) Panax Ginseng genome examination for ginsenoside biosynthesis. Gigascience 6:1–15PubMedPubMedCentralCrossRef Xu J, Chu Y, Liao B, Xiao S, Yin Q, Bai R, Su H, Dong L, Li X, Qian J et al (2017) Panax Ginseng genome examination for ginsenoside biosynthesis. Gigascience 6:1–15PubMedPubMedCentralCrossRef
Zurück zum Zitat Yang XW, Li LY, Tian JM, Zhang ZW, Ye JM, Gu WF (2000) Ginsenoside-Rg6, a novel triterpenoid saponin from the stem-leaves of Panax ginseng CAMey. Chin Chem Lett 11:909–912 Yang XW, Li LY, Tian JM, Zhang ZW, Ye JM, Gu WF (2000) Ginsenoside-Rg6, a novel triterpenoid saponin from the stem-leaves of Panax ginseng CAMey. Chin Chem Lett 11:909–912
Zurück zum Zitat Yang J-L, Hu Z-F, Zhang T-T, Gu A-D, Gong T, Zhu P (2018) Progress on the studies of the key enzymes of ginsenoside biosynthesis. Molecules 23:589PubMedCentralCrossRef Yang J-L, Hu Z-F, Zhang T-T, Gu A-D, Gong T, Zhu P (2018) Progress on the studies of the key enzymes of ginsenoside biosynthesis. Molecules 23:589PubMedCentralCrossRef
Zurück zum Zitat Yoshikawa M, Morikawa T, Yashiro K, Murakami T, Matsuda H (2001) Bioactive saponins and glycosides. XIX. Notoginseng (3): immunological adjuvant activity of notoginsenosides and related saponins: structures of notoginsenosides-L, -M, and -N from the roots of Panax notoginseng (Burk.) F.H. Chen. Chem Pharm Bull (Tokyo) 49:1452–1456CrossRef Yoshikawa M, Morikawa T, Yashiro K, Murakami T, Matsuda H (2001) Bioactive saponins and glycosides. XIX. Notoginseng (3): immunological adjuvant activity of notoginsenosides and related saponins: structures of notoginsenosides-L, -M, and -N from the roots of Panax notoginseng (Burk.) F.H. Chen. Chem Pharm Bull (Tokyo) 49:1452–1456CrossRef
Zurück zum Zitat Yoshikawa M, Morikawa T, Kashima Y, Ninomiya K, Matsuda H (2003) Structures of new dammarane-type triterpene saponins from the flower buds of Panax notoginseng and hepatoprotective effects of principal ginseng saponins. J Nat Prod Res 66:922–927CrossRef Yoshikawa M, Morikawa T, Kashima Y, Ninomiya K, Matsuda H (2003) Structures of new dammarane-type triterpene saponins from the flower buds of Panax notoginseng and hepatoprotective effects of principal ginseng saponins. J Nat Prod Res 66:922–927CrossRef
Zurück zum Zitat Yoshikawa M, Sugimoto S, Nakamura S, Sakumae H, Matsuda H (2007a) Medicinal flowers. XVI. New dammarane-type triterpene tetraglycosides and gastroprotective principles from flower buds of Panax ginseng. Chem Pharm Bull 55:1034–1038CrossRef Yoshikawa M, Sugimoto S, Nakamura S, Sakumae H, Matsuda H (2007a) Medicinal flowers. XVI. New dammarane-type triterpene tetraglycosides and gastroprotective principles from flower buds of Panax ginseng. Chem Pharm Bull 55:1034–1038CrossRef
Zurück zum Zitat Yoshikawa M, Sugimoto S, Nakam S, Matsuda H (2007b) Medicinal flowers. XI. Structures of new dammarane-type triterpene diglycosides with hydroperoxide group from flower buds of Panax ginseng. Chem Pharm Bull (Tokyo) 55:571–576CrossRef Yoshikawa M, Sugimoto S, Nakam S, Matsuda H (2007b) Medicinal flowers. XI. Structures of new dammarane-type triterpene diglycosides with hydroperoxide group from flower buds of Panax ginseng. Chem Pharm Bull (Tokyo) 55:571–576CrossRef
Zurück zum Zitat Yuan L, Ji TF, Li CJ, Wang AG, Yang JB, Su YL (2009) Two new steroidal saponins from the seeds of Allium cepa L. J Asian Nat Prod Res 11:213–218PubMedCrossRef Yuan L, Ji TF, Li CJ, Wang AG, Yang JB, Su YL (2009) Two new steroidal saponins from the seeds of Allium cepa L. J Asian Nat Prod Res 11:213–218PubMedCrossRef
Zurück zum Zitat Zhao Y, Wang W, Han L, Rayburn ER, Hill DL, Wang H, Zhang R (2007) Isolation, structural determination, and evaluation of the biological activity of 20(S)-25-methoxyl-dammarane-3beta, 12beta, 20-triol [20(S)-25-OCH3-PPD], a novel natural product from Panax notoginseng. Med Chem 3:51–60PubMedCrossRef Zhao Y, Wang W, Han L, Rayburn ER, Hill DL, Wang H, Zhang R (2007) Isolation, structural determination, and evaluation of the biological activity of 20(S)-25-methoxyl-dammarane-3beta, 12beta, 20-triol [20(S)-25-OCH3-PPD], a novel natural product from Panax notoginseng. Med Chem 3:51–60PubMedCrossRef
Zurück zum Zitat Zhu S, Zou K, Fushimi H, Cai S, Komatsu K (2004) Comparative study on triterpene saponins of ginseng drugs. Planta Med 70:666–677PubMedCrossRef Zhu S, Zou K, Fushimi H, Cai S, Komatsu K (2004) Comparative study on triterpene saponins of ginseng drugs. Planta Med 70:666–677PubMedCrossRef
Zurück zum Zitat Zou K, Zhu S, Meselhy Tohda M, Cai S, Komatsu K (2002a) Dammarane-type saponins from Panax japonicus and their neurite outgrowth activity in SK-N-SH cells. J Nat Prod 65:1288–1292PubMedCrossRef Zou K, Zhu S, Meselhy Tohda M, Cai S, Komatsu K (2002a) Dammarane-type saponins from Panax japonicus and their neurite outgrowth activity in SK-N-SH cells. J Nat Prod 65:1288–1292PubMedCrossRef
Zurück zum Zitat Zou K, Zhu S, Tohda C, Cai S, Komatsu K (2002b) Dammarane-type Triterpene Saponins from Panax japonicas. J Nat Prod 65:346–351PubMedCrossRef Zou K, Zhu S, Tohda C, Cai S, Komatsu K (2002b) Dammarane-type Triterpene Saponins from Panax japonicas. J Nat Prod 65:346–351PubMedCrossRef
Metadaten
Titel
Metabolic and Functional Diversity of Saponins
verfasst von
Mostafa Abdelrahman
Sudisha Jogaiah
Copyright-Jahr
2020
DOI
https://doi.org/10.1007/978-3-030-61149-1_3

    Marktübersichten

    Die im Laufe eines Jahres in der „adhäsion“ veröffentlichten Marktübersichten helfen Anwendern verschiedenster Branchen, sich einen gezielten Überblick über Lieferantenangebote zu verschaffen.