Abstract
Main conclusion
Steroidal saponins exhibited numerous pharmacological activities due to the modification of their backbone by different cytochrome P450s (P450) and UDP glycosyltransferases (UGTs). Plant-derived steroidal saponins are not sufficient for utilizing them for commercial purpose so in vitro production of saponin by tissue culture, root culture, embryo culture, etc, is necessary for its large-scale production.
Saponin glycosides are the important class of plant secondary metabolites, which consists of either steroidal or terpenoidal backbone. Due to the existence of a wide range of medicinal properties, saponin glycosides are pharmacologically very important. This review is focused on important medicinal properties of steroidal saponin, its occurrence, and biosynthesis. In addition to this, some recently identified plants containing steroidal saponins in different parts were summarized. The high throughput transcriptome sequencing approach elaborates our understanding related to the secondary metabolic pathway and its regulation even in the absence of adequate genomic information of non-model plants. The aim of this review is to encapsulate the information related to applications of steroidal saponin and its biosynthetic enzymes specially P450s and UGTs that are involved at later stage modifications of saponin backbone. Lastly, we discussed the in vitro production of steroidal saponin as the plant-based production of saponin is time-consuming and yield a limited amount of saponins. A large amount of plant material has been used to increase the production of steroidal saponin by employing in vitro culture technique, which has received a lot of attention in past two decades and provides a way to conserve medicinal plants as well as to escape them for being endangered.
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References
Abbassi SJ, Vishwakarma RK, Patel P, Kumari U, Khan BM (2015) Bacopa monniera recombinant mevalonate diphosphate decarboxylase: biochemical characterization. Int J Biol Macromol 79:661–668
Abdelrahman M, El-Sayed M, Sato S, Hirakawa H, Ito SI, Tanaka K, Mine Y, Sugiyama N, Suzuki M, Yamauchi N, Shigyo M (2017) 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:e0181784
Abe I, Rohmer M, Prestwich GD (1993) Enzymatic cyclization of squalene and oxidosqualene to sterols and triterpenes. Chem Rev 93:2189–2206
Acharya D, Mitaine-Offer AC, Kaushik N, Miyamoto T, Paululat T, Mirjolet JF, Duchamp O, Lacaille-Dubois MA (2010) Steroidal saponins from Chlorophytum orchidastrum. J Nat Prod 73:7–11
Adão CR, Pereira da Silva B, Tinoco LW, Parente JP (2012) Haemolytic activity and immunological adjuvant effect of a new steroidal saponin from Allium ampeloprasum var. porrum. Chem Biodivers 9:58–67
Ahn JH, Son KH, Sohn HY, Kwon ST (2005) In vitro culture of adventitious roots from Dioscorea nipponica Makino for the production of steroidal saponins. Kor J Plant Biotechnol 32:217–223
Ahn MJ, Kim CY, Yoon KD, Ryu MY, Cheong JH, Chin YW, Kim J (2006) Steroidal saponins from the rhizomes of Polygonatum sibiricum. J Nat Prod 69:360–364
Akhtar N, Gupta P, Sangwan NS, Sangwan RS, Trivedi PK (2013) Cloning and functional characterization of 3-hydroxy-3-methylglutaryl coenzyme A reductase gene from Withania somnifera: an important medicinal plant. Protoplasma 250:613–622
Akkol EK, Tatli II, Akdemir ZS (2007) Antinociceptive and anti-inflammatory effects of saponin and iridoid glycosides from Verbascum pterocalycinum var. mutense. Hub Mor Z Naturforsch C 62:813–820
Aoyagi K, Beyou A, Moon K, Fang L, Ulrich T (1993) Isolation and characterization of cDNAs encoding wheat 3-hydroxy-3-methylglutaryl coenzyme A reductase. Plant Physiol 102:623–628
Apaya MK, Chichioco-Hernandez CL (2014) New steroidal saponin from Antigonon leptopus Hook. and Arn. Pharmacogn Mag 10:S501–S505
Arendt P, Miettinen K, Pollier J, De Rycke R, Callewaert N, Goossens A (2017) An endoplasmic reticulum-engineered yeast platform for overproduction of triterpenoids. Metab Eng 40:165–175
Augustin JM, Kuzina V, Andersen SB, Bak S (2011) Molecular activities, biosynthesis and evolution of triterpenoid saponins. Phytochemistry 72:435–457
Babiychuk E, Bouvier-Navé P, Compagnon V, Suzuki M, Muranaka T, Van Montagu M, Kushnir S, Schaller H (2008) Albinism and cell viability in cycloartenol synthase deficient Arabidopsis. Plant Signal Behav 3:978–980
Bai H, Li W, Zhao H, Anzai Y, Li H, Guo H, Kato F, Koike K (2014) Isolation and structural elucidation of novel cholestane glycosides and spirostane saponins from Polygonatum odoratum. Steroids 80:7–14
Bak S, Kahn RA, Olsen CE, Halkier BA (1997) Cloning and expression in Escherichia coli of the obtusifoliol 14α-demethylase of Sorghum bicolor (L.) Moench, a cytochrome P450 orthologous to the sterol 14α-demethylases (CYP51) from fungi and mammals. Plant J 11:191–201
Bak S, Beisson F, Bishop G, Hamberger B, Höfer R, Paquette S, Werck-Reichhart D (2011) Cytochromes p450. Arabidopsis Book 9:e0144
Basu S, Jha TB (2015) In vitro root culture: an alternative source of bioactives in the rare aphrodisiac herb Chlorophytum borivilianum Sant et Fern. Plant Tissue Cult Biotech 23:133–146
Belhouchet Z, Sautour M, Miyamoto T, Lacaille-Dubois MA (2008) Steroidal saponins from the roots of Smilax aspera subsp. mauritanica. Chem Pharm Bull (Tokyo) 56:1324–1327
Bhattacharyya MK, Paiva NL, Dixon RA, Korth KL, Stermer BA (1995) Features of the hmg 1 subfamily of genes encoding HMG-CoA reductase in potato. Plant Mol Biol 28:1–15
Bhuvanalakshmi G, Basappa Rangappa KS, Dharmarajan A, Sethi G, Kumar AP, Warrier S (2017) Breast cancer stem-like cells are inhibited by diosgenin, a steroidal saponin, by the attenuation of the Wnt β-catenin signaling via the Wnt antagonist secreted frizzled related protein-4. Front Pharmacol 8:124
Cabello-Hurtado F, Taton M, Forthoffer N, Kahn R, Bak S, Rahier A, Werck-Reichhart D (1999) Optimized expression and catalytic properties of a wheat obtusifoliol 14α-demethylase (CYP51) expressed in yeast. Complementation of erg11Delta yeast mutants by plant CYP51. Eur J Biochem 262:435–446
Cao X, Zong Z, Ju X, Sun Y, Dai C, Liu Q, Jiang J (2010) Molecular cloning, characterization and function analysis of the gene encoding HMG-CoA reductase from Euphorbia Pekinensis Rupr. Mol Biol Rep 37:1559–1567
Challinor VL, De Voss JJ (2013) Open-chain steroidal glycosides, a diverse class of plant saponins. Nat Prod Rep 30:429–454
Challinor VL, Stuthe JM, Bernhardt PV, Lehmann RP, Kitching W, De Voss JJ (2011) Structure and absolute configuration of helosides A and B, new saponins from Chamaelirium luteum. J Nat Prod 74:1557–1560
Challinor VL, Parsons PG, Chap S, White EF, Blanchfield JT, Lehmann RP, De Voss JJ (2012a) Steroidal saponins from the roots of Smilax sp.: structure and bioactivity. Steroids 77:504–511
Challinor VL, Piacente S, De Voss JJ (2012b) NMR assignment of the absolute configuration of C-25 in furostanol steroidal saponins. Steroids 77:602–608
Challinor VL, Stuthe JM, Parsons PG, Lambert LK, Lehmann RP, Kitching W, De Voss JJ (2012c) Structure and bioactivity of steroidal saponins isolated from the roots of Chamaelirium luteum (false unicorn). J Nat Prod 75:1469–1479
Chan JY, Koon JC, Liu X, Detmar M, Yu B, Kong SK, Fung KP (2011) Polyphyllin D, a steroidal saponin from Paris polyphylla, inhibits endothelial cell functions in vitro and angiogenesis in zebrafish embryos in vivo. J Ethnopharmacol 137:64–69
Chen HF, Wang GH, Luo Q, Wang NL, Yao XS (2009) Two new steroidal saponins from Allium macrostemon bunge and their cytotoxity on different cancer cell lines. Molecules 14:2246–2253
Chen G, Chen H, Li W, Pei YH (2011a) Steroidal glycosides from Cynanchum amplexicaule. J Asian Nat Prod Res 13:756–760
Chen PY, Chen CH, Kuo CC, Lee TH, Kuo YH, Lee CK (2011b) Cytotoxic steroidal saponins from Agave sisalana. Planta Med 77:929–933
Chen G, Yi S, Hua HM, Lu X, Pei YH (2012) Two new steroidal glycosides from Cynanchum amplexicaule. J Asian Nat Prod Res 14:559–563
Chen G, Su L, Feng SG, Lu X, Wang H, Pei YH (2013) Furostanol saponins from the fruits of Tribulus terrestris. Nat Prod Res 27:1186–1190
Chen Y, Tang YM, Yu SL, Han YW, Kou JP, Liu BL, Yu BY (2015) Advances in the pharmacological activities and mechanisms of diosgenin. Chin J Nat Med 13:578–587
Chen MH, Chen XJ, Wang M, Lin LG, Wang YT (2016) Ophiopogon japonicus—A phytochemical, ethnomedicinal and pharmacological review. J Ethnopharmacol 181:193–213
Cheng ZH, Wu T, Yu BY (2006) Steroidal glycosides from tubers of Ophiopogon japonicus. J Asian Nat Prod Res 8:555–559
Chevallier A (2000) Encyclopedia of herbal medicine. Dorling Kindersley Publishing, New York, p 271
Choi DW, Jung J, Ha YI, Park HW, In DS, Chung HJ, Liu JR (2005) Analysis of transcripts in methyl jasmonate-treated ginseng hairy roots to identify genes involved in the biosynthesis of ginsenosides and other secondary metabolites. Plant Cell Rep 23:557–566
Choi SJ, Choi J, Jeon H, Bae SK, Ko J, Kim J, Yoon KD (2015) Application of high-performance countercurrent chromatography for the isolation of steroidal saponins from Liriope plathyphylla. J Sep Sci 38:18–24
Chung YL, Pan CH, Wang CC, Hsu KC, Sheu MJ, Chen HF, Wu CH (2016) Methyl protodioscin, a steroidal saponin, inhibits neointima formation in vitro and in vivo. J Nat Prod 79:1635–1644
Chye ML, Kush A, Tan CT, Chua NH (1991) Characterization of cDNA and genomic clones encoding 3-hydroxy-3-methylglutaryl-coenzyme A reductase from Hevea brasiliensis. Plant Mol Biol 16:567–577
Ciura J, Szeliga M, Grzesik M, Tyrka M (2017) Next-generation sequencing of representational difference analysis products for identification of genes involved in diosgenin biosynthesis in fenugreek (Trigonella foenum-graecum). Planta 245:977–991
Colmenares AP, Rojas LB, Mitaine-Offer AC, Pouységu L, Quideau S, Miyamoto T, Tanaka C, Paululat T, Usubillaga A, Lacaille-Dubois MA (2013) Steroidal saponins from the fruits of Solanum torvum. Phytochemistry 86:137–143
Cordoba E, Porta H, Arroyo A, San Román C, Medina L, Rodriguez-Concepcion M, León P (2011) Functional characterization of the three genes encoding 1-deoxy-d-xylulose 5-phosphate synthase in maize. J Exp Bot 62:2023–2038
Cui JM, Kang LP, Zhao Y, Zhao JY, Zhang J, Pang X, Yu HS, Jia DX, Liu C, Yu LY, Ma BP (2016) Steroidal saponins from the rhizomes of Aspidistra typica. PLoS ONE 11:e0150595
Dai Z, Cui G, Zhou SF, Zhang X, Huang L (2011) Cloning and characterization of a novel 3-hydroxy-3-methylglutaryl coenzyme A reductase gene from Salvia miltiorrhiza involved in diterpenoid tanshinone accumulation. J Plant Physiol 168:148–157
Dai Z, Liu Y, Zhang X, Shi M, Wang B, Wang D, Huang L, Zhang X (2013) Metabolic engineering of Saccharomyces cerevisiae for production of ginsenosides. Metab Eng 20:146–156
De Lucca AJ, Boue S, Palmgren MS, Maskos K, Cleveland TE (2006) Fungicidal properties of two saponins from Capsicum frutescens and the relationship of structure and fungicidal activity. Can J Microbiol 52:336–342
De Marino S, Festa C, Zollo F, Iorizzi M (2012) Novel steroidal components from the underground parts of Ruscus aculeatus L. Molecules 17:14002–14014
Deng D, Lauren DR, Cooney JM, Jensen DJ, Wurms KV, Upritchard JE, Cannon RD, Wang MZ, Li MZ (2008) Antifungal saponins from Paris polyphylla Smith. Planta Med 74:1397–1402
Dhar N, Rana S, Razdan S, Bhat WW, Hussain A, Dhar RS, Vaishnavi S, Hamid A, Vishwakarma R, Lattoo SK (2014) Cloning and functional characterization of three branch point oxidosqualene cyclases from Withania somnifera (L.) dunal. J Biol Chem 289:17249–17267
Diab Y, Ioannou E, Emam A, Vagias C, Roussis V (2012) Desmettianosides A and B, bisdesmosidic furostanol saponins with molluscicidal activity from Yucca desmettiana. Steroids 77:686–690
Diarra ST, He J, Wang J, Li J (2013) Ethylene treatment improves diosgenin accumulation in in vitro cultures of Dioscorea zingiberensis via up-regulation of CAS and HMGR gene expression. Elect J Biotech 16:1–10
Duckstein SM, Lorenz P, Conrad J, Stintzing FC (2014) Tandem mass spectrometric characterization of acetylated polyhydroxy hellebosaponins, the principal steroid saponins in Helleborus niger L. roots. Rapid Commun Mass Spectrom 28:1801–1812
Ebrahimi MA, Payan A (2013) Induction of callus and somatic embryogenesis from cotyledon explants of Fagonia indica Burm. J Med Plants By Prod 2:209–214
El-Sayed MM, Abdel-Hameed ES, El-Nahas HA, El-Wakil EA (2006) Isolation and identification of some steroidal glycosides of Furcraea selloa. Pharmazie 61:478–482
Eskander J, Lavaud C, Harakat D (2010) Steroidal saponins from the leaves of Agave macroacantha. Fitoterapia 81:371–374
Eskander J, Lavaud C, Harakat D (2011) Steroidal saponins from the leaves of Beaucarnea recurvata. Phytochemistry 72:946–951
Fabris M, Matthijs M, Carbonelle S, Moses T, Pollier J, Dasseville R, Baart GJ, Vyverman W, Goossens A (2014) Tracking the sterol biosynthesis pathway of the diatom Phaeodactylum tricornutum. New Phytol 204:521–535
Folwarczna J, Zych M, Nowińska B, Pytlik M, Bialik M, Jagusiak A, Lipecka-Karcz M, Matysiak M (2016) Effect of diosgenin, a steroidal sapogenin, on the rat skeletal system. Acta Biochim Pol 63:287–295
Fouad MA, Mohamed KM, Kamel MS, Matsunami K, Otsuka H (2008) Cesdiurins I-III, steroidal saponins from Cestrum diurnum L. J Nat Med 62:168–173
Fukushima EO, Seki H, Sawai S, Suzuki M, Ohyama K, Saito K, Muranaka T (2013) Combinatorial biosynthesis of legume natural and rare triterpenoids in engineered yeast. Plant Cell Physiol 54(5):740–749
Fuller S, Stephens JM (2015) Diosgenin, 4-hydroxyisoleucine, and fiber from fenugreek: mechanisms of actions and potential effects on metabolic syndrome. Adv Nutr 6:189–197
Gajdus J, Kaczyński Z, Kawiak A, Lojkowska E, Stefanowicz-Hajduk J, Ochocka JR, Stepnowski P (2014) Isolation and identification of cytotoxic compounds from the rhizomes of Paris quadrifolia L. Pharmacogn Mag 10:S324–S333
Galarraga E, Mitaine-Offer AC, Amaro-Luis JM, Miyamoto T, Tanaka C, Pouységu L, Quideau S, Rojas LB, Lacaille-Dubois MA (2011) Steroidal saponins from the fruits of Cestrum ruizteranianum. Nat Prod Commun 6:1825–1826
Gas-Pascual E, Berna A, Bach TJ, Schaller H (2014) Plant oxidosqualene metabolism: cycloartenol synthase-dependent sterol biosynthesis in Nicotiana benthamiana. PLoS ONE 9:e109156
Gnoula C, Mégalizzi V, De Nève N, Sauvage S, Ribaucour F, Guissou P, Duez P, Dubois J, Ingrassia L, Lefranc F, Kiss R, Mijatovic T (2008) Balanitin-6 and -7: diosgenyl saponins isolated from Balanites aegyptiaca Del. display significant anti-tumor activity in vitro and in vivo. Int J Oncol 32:5–15
Gong Y, Liao Z, Chen M, Zuo K, Guo L, Tan Q, Huang Z, Kai G, Sun X, Tan F, Tang K (2005) Molecular cloning and characterization of a 1-deoxy-d-xylulose 5-phosphate reductoisomerase gene from Ginkgo biloba. DNA Seq 16:111–120
Gruenweller S, Schroeder E, Kesselmeier J (1990) Biological activities of furostanol saponins from Nicotiana tabacum. Phytochemistry 29:2485–2490
Guclu Ustundag O, Mazza G (2007) Saponins: properties, applications and processing. Crit Rev Food Sci Nutr 47:231–258
Guo Y, Liu YX, Kang LP, Zhang T, Yu HS, Zhao Y, Xiong CQ, Ma BP (2013) Two novel furostanol saponins from the tubers of Ophiopogon japonicus. J Asian Nat Prod Res 15:459–465
Guo J, Xu C, Xue R, Jiang W, Wu B, Huang C (2015) Cytotoxic activities of chemical constituents from rhizomes of Anemarrhena asphodeloides and their analogues. Arch Pharm Res 38:598–603
Guo H, Li R, Liu S, Zhao N, Han S, Lu M, Liu X, Xia X (2016) Molecular characterization, expression, and regulation of Gynostemma pentaphyllum squalene epoxidase gene 1. Plant Physiol Biochem 109:230–239
Ha SH, Lee SW, Kim YM, Hwang YS (2001) Molecular characterization of Hmg2 gene encoding a 3-hydroxy-methylglutaryl-CoA reductase in rice. Mol Cells 11:295–302
Ha SH, Kim JB, Hwang YS, Lee SW (2003) Molecular characterization of three 3-hydroxy-3-methylglutaryl-CoA reductase genes including pathogen-induced Hmg2 from pepper (Capsicum annuum). Biochim Biophys Acta 1625:253–260
Han JY, In JG, Kwon YS, Choi YE (2010) Regulation of ginsenoside and phytosterol biosynthesis by RNA interferences of squalene epoxidase gene in Panax ginseng. Phytochemistry 71:36–46
Haralampidis K, Trojanowska M, Osbourn AE (2002) Biosynthesis of triterpenoid saponins in plants. Adv Biochem Eng Biotechnol 75:31–49
Hayes PY, Lambert LK, Lehmann R, Penman K, Kitching W, De Voss JJ (2007) Complete (1)H and (13)C assignments of the four major saponins from Dioscorea villosa (wild yam). Magn Reson Chem 45:1001–1005
Hayes PY, Jahidin AH, Lehmann R, Penman K, Kitching W, De Voss JJ (2008) Steroidal saponins from the roots of Asparagus racemosus. Phytochemistry 69:796–804
Hayes PY, Lehmann R, Penman K, Kitching W, De Voss JJ (2009) Steroidal saponins from the roots of Trillium erectum (Beth root). Phytochemistry 70:105–113
He H, Sun YP, Zheng L, Yue ZG (2015) Steroidal saponins from Paris polyphylla induce apoptotic cell death and autophagy in A549 human lung cancer cells. Asian Pac J Cancer Prev 16:1169–1173
Hong XX, Luo JG, Guo C, Kong LY (2012) New steroidal saponins from the bulbs of Lilium brownii var. viridulum. Carbohydr Res 361:19–26
Hostettmann K, Marston A (1995) Saponins. Cambridge University Press, Cambridge
Hostettmann K, Marston A (2005) Saponins, chemistry and pharmacology of natural products. Cambridge University Press, Cambridge
Huang X, Kong L (2006) Steroidal saponins from roots of Asparagus officinalis. Steroids 71:171–176
Huang W, Zou K (2015) Cytotoxicity of the saponin TTB2 on Ewing sarcoma cells. Exp Ther Med 10:625–628
Huang HL, Liu RH, Shao F (2009) Structural determination of two new steroidal saponins from Smilax china. Magn Reson Chem 47:741–745
Huang HC, Lin MK, Hwang SY, Hwang TL, Kuo YH, Chang CI, Ou CY, Kuo YH (2013) Two anti-inflammatory steroidal saponins from Dracaena angustifolia Roxb. Molecules 18:8752–8763
Ikenaga T, Oyama T, Muranaka T (1995) Growth and steroidal saponin production in hairy root cultures of Solanum aculeatissimum. Plant Cell Rep 14:413–417
Ikenaga T, Handayani R, Oyama T (2000) Steroidal saponin production in callus cultures of Solanum aculeatissimum Jacq. Plant Cell Rep 19:1240–1244
Inoue K, Shimomura K, Kobayashi S, Sankawa U, Ebizuka Y (1996) Conversion of furostanol glycoside to spirostanol glycoside by β-glucosidase in Costus speciosus. Phytochemistry 41:725–727
Ivanova A, Mikhova B, Klaiber I, Dinchev D, Kostova I (2009) Steroidal saponins from Smilax excelsa rhizomes. Nat Prod Res 23:916–924
Ivanova T, Dimitrova D, Gussev C, Bosseva Y, Stoeva T (2015) Ex situ conservation of Ruscus aculeatus L.—ruscogenin biosynthesis, genome-size stability and propagation traits of tissue-cultured clones. Biotechnol Biotechnol Equip 29:27–32
Jain AK, Vincent RM, Nessler CL (2000) Molecular characterization of a hydroxymethylglutaryl-CoA reductase gene from mulberry (Morus alba L.). Plant Mol Biol 42:559–569
Jayachandran KS, Vasanthi AH, Gurusamy N (2016) Steroidal saponin diosgenin from Dioscorea bulbifera protects cardiac cells from hypoxia-reoxygenation Injury through modulation of pro-survival and pro-death molecules. Pharmacogn Mag 12:14–20
Jeena GS, Fatima S, Tripathi P, Upadhyay S, Shukla RK (2017) Comparative transcriptome analysis of shoot and root tissue of Bacopa monnieri identifies potential genes related to triterpenoid saponin biosynthesis. BMC Genom 18:490
Jiang D, Rong Q, Chen Y, Yuan Q, Shen Y, Guo J, Yang Y, Zha L, Wu H, Huang L, Liu C (2017) Molecular cloning and functional analysis of squalene synthase (SS) in Panax notoginseng. Int J Biol Macromol 95:658–666
Jin H, Gong Y, Guo B, Qiu C, Liu D, Miao Z, Sun X, Tang K (2006) Isolation and characterization of a 2C-methyl-d-erythritol 2, 4-cyclodiphosphate synthase gene from Taxus media. Mol Biol (Mosk) 40:1013–1020
Jin YL, Kuk JH, Oh KT, Kim YJ, Piao XL, Park RD (2007) A new steroidal saponin, yuccalan, from the leaves of Yucca smalliana. Arch Pharm Res 30:543–546
Jones RN, Katzenellenbogen E, Dobriner K (1953) Steroid metabolism. XVII. The infrared absorption spectra of the steroid sapogenins. J Am Chem Soc 75:158–166
Kalita R, Patar L, Shasany AK, Modi MK, Sen P (2015) Molecular cloning, characterization and expression analysis of 3-hydroxy-3-methylglutaryl coenzyme A reductase gene from Centella asiatica L. Mol Biol Rep 42:1431–1439
Kalra S, Kumar S, Lakhanpal N, Kaur J, Singh K (2013) Characterization of Squalene synthase gene from Chlorophytum borivilianum (Sant. and Fernand.). Mol Biotechnol 54:944–953
Kaneda N, Nakanishi H, Staba EJ (1987) Steroidal constituents of Yucca shidigera plants and tissue cultures. Phytochemistry 26:1425–1429
Kang LP, Ma BP, Shi TJ, Zhang J, Xiong CQ (2006) Two new furostanol saponins from the rhizomes of Anemarrhena asphodeloides. Yao Xue Xue Bao 41:527–532
Kang YJ, Chung HJ, Nam JW, Park HJ, Seo EK, Kim YS, Lee D, Lee SK (2011) Cytotoxic and antineoplastic activity of timosaponin A-III for human colon cancer cells. J Nat Prod 74:701–706
Kang LP, Liu YX, Eichhorn T, Dapat E, Yu HS, Zhao Y, Xiong CQ, Liu C, Efferth T, Ma BP (2012a) Polyhydroxylated steroidal glycosides from Paris polyphylla. J Nat Prod 75:1201–1205
Kang LP, Wang YZ, Feng B, Huang HZ, Zhou WB, Zhao Y, Xiong CQ, Tan DW, Song XB, Ma BP (2012b) Structure elucidation and complete NMR spectral assignments of glucosylated saponins of cantalasaponin I. Magn Reson Chem 50:79–83
Kang LP, Zhang J, Cong Y, Li B, Xiong CQ, Zhao Y, Tan DW, Yu HS, Yu ZY, Cong YW, Liu C, Ma BP (2012c) Steroidal glycosides from the rhizomes of Anemarrhena asphodeloides and their antiplatelet aggregation activity. Planta Med 78:611–616
Kang LP, Wu KL, Yu HS, Pang X, Liu J, Han LF, Zhang J, Zhao Y, Xiong CQ, Song XB, Liu C, Cong YW, Ma BP (2014) Steroidal saponins from Tribulus terrestris. Phytochemistry 107:182–189
Kawabata T, Cui MY, Hasegawa T, Takano F, Ohta T (2011) Anti-inflammatory and anti-melanogenic steroidal saponin glycosides from Fenugreek (Trigonella foenum-graecum L.) seeds. Planta Med 77:705–710
Keim V, Manzano D, Fernández FJ, Closa M, Andrade P, Caudepón D, Bortolotti C, Vega MC, Arró M, Ferrer A (2012) Characterization of Arabidopsis FPS isozymes and FPS gene expression analysis provide insight into the biosynthesis of isoprenoid precursors in seeds. PLoS ONE 7:e49109
Kim SM, Kuzuyama T, Chang YJ, Kim SU (2006) Cloning and characterization of 2-C-methyl-d-erythritol 2,4-cyclodiphosphate synthase (MECS) gene from Ginkgo biloba. Plant Cell Rep 25:829–835
Kim TD, Han JY, Huh GH, Choi YE (2011) Expression and functional characterization of three squalene synthase genes associated with saponin biosynthesis in Panax ginseng. Plant Cell Physiol 52:125–137
Kim CS, Kim SY, Moon E, Lee MK, Lee KR (2013) Steroidal constituents from the leaves of Hosta longipes and their inhibitory effects on nitric oxide production. Bioorg Med Chem Lett 15:1771–1775
Kim YJ, Lee OR, Oh JY, Jang MG, Yang DC (2014) Functional analysis of 3-hydroxy-3-methylglutaryl coenzyme A reductase encoding genes in triterpene saponin-producing ginseng. Plant Physiol 165:373–387
Kim JE, Go J, Koh EK, Song SH, Sung JE, Lee HA, Kim DS, Son HJ, Lee HS, Lee CY, Hong JT, Hwang DY (2016) Diosgenin effectively suppresses skin inflammation induced by phthalic anhydride in IL-4/Luc/CNS-1 transgenic mice. Biosci Biotechnol Biochem 80:891–901
Kime B, Barminas JT, Nkafamiya II, Akinterinwa A (2015) Extraction and evaluation of a saponin-based surfactant from Balanites aegyptiaca plant as an emulsifying agent. Int J Innov Sci Eng Technol 2:733–737
Kirmizibekmez H, Masullo M, Festa M, Capasso A, Piacente S (2014) Steroidal glycosides with antiproliferative activities from Digitalis trojana. Phytother Res 28:534–538
Kitagawa I (2002) Licorice root. A natural sweetener and an important ingredient in Chinese medicine. Pure Appl Chem 74:1189–1198
Kochan E, Szymczyk P, Kuźma Ł, Lipert A, Szymańska G (2017) Yeast extract stimulates ginsenoside production in hairy root cultures of American ginseng cultivated in shake flasks and nutrient sprinkle bioreactors. Molecules 22(6):880
Kohara A, Nakajima C, Hashimoto K, Ikenaga T, Tanaka H, Shoyama Y, Yoshida S, Muranaka T (2005) A novel glucosyltransferase involved in steroid saponin biosynthesis in Solanum aculeatissimum. Plant Mol Biol 57:225–239
Kornobis E, Cabellos L, Aguilar F, Frias-Lopez C, Rozas J, Marco J, Zardoya R (2015) TRUFA: a user-friendly web server for de novo RNA-seq analysis using cluster computing. Evol Bioinform 11:97–104
Kostadinova EP, Alipieva KI, Kokubun T, Taskova RM, Handjieva NV (2007) Phenylethanoids, iridoids and a spirostanol saponin from Veronica turrilliana. Phytochemistry 68:1321–1326
Kougan GB, Miyamoto T, Tanaka C, Paululat T, Mirjolet JF, Duchamp O, Sondengam BL, Lacaille-Dubois MA (2010) Steroidal saponins from two species of Dracaena. J Nat Prod 73:1266–1270
Kowalczyk M, Pecio Ł, Stochmal A, Oleszek W (2011) Qualitative and quantitative analysis of steroidal saponins in crude extract and bark powder of Yucca schidigera Roezl. J Agric Food Chem 59:8058–8064
Kumar S, Kalra S, Singh B, Kumar A, Kaur J, Singh K (2016) RNA-Seq mediated root transcriptome analysis of Chlorophytum borivilianum for identification of genes involved in saponin biosynthesis. Funct Integr Genom 16:37–55
Kumari U, Vishwakarma RK, Sonawane P, Abbassi S, Khan BM (2015) Biochemical characterization of recombinant mevalonate kinase from Bacopa monniera. Int J Biol Macromol 72:776–783
Kuo CI, Chao CH, Lu MK (2012) Effects of auxins on the production of steroidal alkaloids in rapidly proliferating tissue and cell cultures of Solanum lyratum. Phytochem Anal 23:400–404
Kuroda M, Ori K, Mimaki Y (2006) Ornithosaponins A–D, four new polyoxygenated steroidal glycosides from the bulbs of Ornithogalum thyrsoides. Steroids 71:199–205
Lai W, Wu Z, Lin H, Li T, Sun L, Chai Y, Chen W (2010) Anti-ischemia steroidal saponins from the seeds of Allium fistulosum. J Nat Prod 73:1053–1057
Lakshmi V, Kumar R, Pandey K, Joshi BS, Roy R, Madhusudanan KP, Tiwari P, Srivastava AK (2009) Structure and activities of a steroidal saponin from Chlorophytum nimonii (Grah) Dalz. Nat Prod Res 23:963–972
Laranjeira S, Amorim-Silva V, Esteban A, Arró M, Ferrer A, Tavares RM, Botella MA, Rosado A, Azevedo H (2015) Arabidopsis squalene epoxidase 3 (SQE3) complements SQE1 and is important for embryo development and bulk squalene epoxidase activity. Mol Plant 8:1090–1102
Lee B, Trinh HT, Jung K, Han SJ, Kim DH (2010) Inhibitory effects of steroidal timosaponins isolated from the rhizomes of Anemarrhena asphodeloides against passive cutaneous anaphylaxis reaction and pruritus. Immunopharmacol Immunotoxicol 32:357–363
Lee CL, Hwang TL, He WJ, Tsai YH, Yen CT, Yen HF, Chen CJ, Chang WY, Wu YC (2013) Anti-neutrophilic inflammatory steroidal glycosides from Solanum torvum. Phytochemistry 95:315–321
Li X, Sun H, Ye Y, Chen F, Pan Y (2006) C-21 steroidal glycosides from the roots of Cynanchum chekiangense and their immunosuppressive activities. Steroids 71:61–66
Li H, Huang W, Wen Y, Gong G, Zhao Q, Yu G (2010) Anti-thrombotic activity and chemical characterization of steroidal saponins from Dioscorea zingiberensis CH Wright. Fitoterapia 81:1147–1156
Li N, Zhang L, Zeng KW, Zhou Y, Zhang JY, Che YY, Tu PF (2013) Cytotoxic steroidal saponins from Ophiopogon japonicus. Steroids 78:1–7
Li XJ, Wang L, Xue PF, Xie HX, Wei H, Wang J (2015a) New steroidal glycosides from Hosta plantaginea (Lam.) Aschers. J Asian Nat Prod Res 17:224–231
Li Y, Liu C, Xiao D, Han J, Yue Z, Sun Y, Fan L, Zhang F, Meng J, Zhang R, Wang Z, Mei Q, Wen A (2015b) Trillium tschonoskii steroidal saponins suppress the growth of colorectal cancer cells in vitro and in vivo. J Ethnopharmacol 168:136–145
Li Y, Wang X, He H, Zhang D, Jiang Y, Yang X, Wang F, Tang Z, Song X, Yue Z (2015c) Steroidal saponins from the roots and rhizomes of Tupistra chinensis. Molecules 20:13659–13669
Li JL, Gao ZB, Zhao WM (2016) Identification and evaluation of antiepileptic activity of C21 steroidal glycosides from the roots of Cynanchum wilfordii. J Nat Prod 79:89–97
Liang M, Zheng Z, Yuan Y, Kong L, Shen Y, Liu R, Zhang C, Zhang W (2007) Identification and quantification of C21 steroidal saponins from Radix Cynanchi Atrati by high-performance liquid chromatography with evaporative light scattering detection and electrospray mass spectrometric detection. Phytochem Anal 18:428–435
Liang Y, Jiang X, Hu Q, Li X, Yin H, Li D, Zhang Y, Liu X (2014) Cloning and characterization of 3-hydroxy-3-methylglutaryl-CoA reductase (HMGR) gene from Paris fargesii Franch. Indian J Biochem Biophys 51:201–206
Lin JT, Yang DJ (2008) Determination of steroidal saponins in different organs of yam (Dioscorea pseudojaponica Yamamoto). Food Chem 108:1068–1074
Lin S, Wang D, Yang D, Yao J, Tong Y, Chen J (2007) Characterization of steroidal saponins in crude extract from Dioscorea nipponica Makino by liquid chromatography tandem multi-stage mass spectrometry. Anal Chim Acta 599:98–106
Lin T, Huang HL, Liu RH, Shu JC, Ren G, Shao F, Liu LS (2012) Steroidal saponins and pregnane glycosides from Smilax microphylla. Magn Reson Chem 50:813–817
Liu HY, Ni W, Hao XJ, Chen CX (2006) Steroidal saponins from Tacca plantaginea. J Asian Nat Prod Res 8:293–298
Liu T, Chen G, Yi GQ, Xu JK, Zhang TL, Hua HM, Pei YH (2010a) New pregnane and steroidal glycosides from Tribulus terrestris L. J Asian Nat Prod Res 12:209–214
Liu T, Lu X, Wu B, Chen G, Hua HM, Pei YH (2010b) Two new steroidal saponins from Tribulus terrestris L. J Asian Nat Prod Res 12:30–35
Liu H, Chou GX, Wang JM, Ji LL, Wang ZT (2011) Steroidal saponins from the rhizomes of Dioscorea bulbifera and their cytotoxic activity. Planta Med 77:845–848
Liu CX, Guo ZY, Xue YH, Zhang HY, Zhang HQ, Zou K, Huang NY (2012a) Tupisteroide A–C, three new polyhydroxylated steroidal constituents from the roots of Tupistra chinensis. Magn Reson Chem 50:320–324
Liu X, Zhang H, Niu XF, Xin W, Qi L (2012b) Steroidal saponins from Smilacina japonica. Fitoterapia 83:812–816
Liu QB, Peng Y, Li LZ, Gao PY, Sun Y, Yu LH, Song SJ (2013) Steroidal saponins from Anemarrhena asphodeloides. J Asian Nat Prod Res 15:891–898
Liu L, Zhao YL, Cheng GG, Chen YY, Qin XJ, Song CW, Yang XW, Liu YP, Luo XD (2014) Limonoid and steroidal saponin from Azadirachta indica. Nat Prod Bioprospect 4:335–340
Liu JY, Lu L, Kang LP, Liu YX, Zhao Y, Xiong CQ, Zhang YQ, Yu LY, Ma BP (2015a) Selective glycosylation of steroidal saponins by Arthrobacter nitroguajacolicus. Carbohydr Res 402:71–76
Liu Y, Ouyang Y, Wang ZQ, Qiao L, Li S, Zhao SH, Liu MY (2015b) A new C21 steroidal saponins from Periplocae Cortex. Zhongguo Zhong Yao Za Zhi 40:455–457
Liu T, Li X, Xie S, Wang L, Yang S (2016a) RNA-seq analysis of Paris polyphylla var. yunnanensis roots identified candidate genes for saponin synthesis. Plant Divers 38:163–170
Liu Y, Tian X, Hua D, Cheng G, Wang K, Zhang L, Tang H, Wang M (2016b) New steroidal saponins from the rhizomes of Paris delavayi and their cytotoxicity. Fitoterapia 111:130–137
Liu M, Li LN, Pan YT, Kong JQ (2017) cDNA isolation and functional characterization of squalene synthase gene from Ornithogalum caudatum. Protein Expr Purif 130:63–72
Lorent JH, Quetin-Leclercq J, Mingeot-Leclercq MP (2014) The amphiphilic nature of saponins and their effects on artificial and biological membranes and potential consequences for red blood and cancer cells. Org Biomol Chem 12:8803–8822
Lu Y, Luo J, Huang X, Kong L (2009) Four new steroidal glycosides from Solanum torvum and their cytotoxic activities. Steroids 74:95–101
Lu Y, Chen CX, Ni W, Hua Y, Liu HY (2010) Spirostanol tetraglycosides from Ypsilandra thibetica. Steroids 75:982–987
Lu Y, Luo J, Kong L (2011) Steroidal alkaloid saponins and steroidal saponins from Solanum surattense. Phytochemistry 72:668–673
Luo Y, Shen HY, Zuo WJ, Wang H, Mei WL, Dai HF (2015) A new steroidal saponin from dragon’s blood of Dracaena cambodiana. J Asian Nat Prod Res 17:409–414
Ma S, Kou J, Yu B (2011) Safety evaluation of steroidal saponin DT-13 isolated from the tuber of Liriope muscari (Decne.) Baily. Food Chem Toxicol 49:2243–2251
Maldonado-Mendoza IE, Vincent RM, Nessler CL (1997) Molecular characterization of three differentially expressed members of the Camptotheca acuminata 3-hydroxy-3-methylglutaryl CoA reductase (HMGR) gene family. Plant Mol Biol 34:781–790
Mandal D, Banerjee S, Mondal NB, Chakravarty AK, Sahu NP (2006) Steroidal saponins from the fruits of Asparagus racemosus. Phytochemistry 67:1316–1321
Marshall JG, Staba EJ (1976) Hormonal effects on diosgenin biosynthesis and growth in Dioscorea deltoidea tissue cultures. Phytochemistry 15:53–55
Masullo M, Pizza C, Piacente S (2016) Ruscus genus: a rich source of bioactive steroidal saponins. Planta Med 82:1513–1524
Matsuo Y, Watanabe K, Mimaki Y (2008) New steroidal glycosides from rhizomes of Clintonia udensis. Biosci Biotechnol Biochem 72:1714–1721
Moehs CP, Allen PV, Friedman M, Belknap WR (1997) Cloning and expression of solanidine UDP-glucose glucosyltransferase from potato. Plant J 11:227–236
Moharram FA, EI-Shenawy SM (2007) Antinociceptive and anti-inflammatory steroidal saponins from Dracaena ombet. Planta Med 73:1101–1106
Montes EG, Mitaine-Offer AC, Amaro-Luis JM, Paululat T, Delaude C, Pouységu L, Quideau S, Rojas LB, Delemasure S, Dutartre P, Lacaille-Dubois MA (2014) Acylated oleanane-type saponins from Ganophyllum giganteum. Phytochemistry 98:236–242
Morrissey JP, Osbourn AE (1999) Fungal resistance to plant antibiotics as a mechanism of pathogenesis. Microbiol Mol Biol Rev 63:708–724
Moses T, Papadopoulou KK, Osbourn A (2014a) Metabolic and functional diversity of saponins, biosynthetic intermediates and semi-synthetic derivatives. Crit Rev Biochem Mol Biol 49:439–462
Moses T, Pollier J, Almagro L, Buyst D, Van Montagu M, Pedreño MA, Martins JC, Thevelein JM, Goossens A (2014b) Combinatorial biosynthesis of sapogenins and saponins in Saccharomyces cerevisiae using a C-16α hydroxylase from Bupleurum falcatum. Proc Natl Acad Sci USA 111(4):1634–1639
Mskhiladze L, Kutchukhidze J, Chincharadze D, Delmas F, Elias R, Favel A (2008a) In vitro antifungal and antileishmanial activities of steroidal saponins from Allium leucanthum C. Koch—a Caucasian endemic species. Georgian Med News 154:39–43
Mskhiladze L, Legault J, Lavoie S, Mshvildadze V, Kuchukhidze J, Elias R, Pichette A (2008b) Cytotoxic steroidal saponins from the flowers of Allium leucanthum. Molecules 13:2925–2934
Munafo JP, Ramanathan A, Jimenez LS, Gianfagna TJ (2010) Isolation and structural determination of steroidal glycosides from the bulbs of Easter lily (Lilium longiflorum Thunb.). J Agric Food Chem 58:8806–8813
Nakamura S, Hongo M, Sugimoto S, Matsuda H, Yoshikawa M (2008) Steroidal saponins and pseudoalkaloid oligoglycoside from Brazilian natural medicine, “fruta do lobo” (fruit of Solanum lycocarpum). Phytochemistry 69:1565–1572
Nakayasu M, Kawasaki T, Lee HJ, Sugimoto Y, Onjo M, Muranaka T, Mizutani M (2015) Identification of furostanol glycoside 26-O-β-glucosidase involved in steroidal saponin biosynthesis from Dioscorea esculenta. Plant Biotechnol 32:299–308
Napolitano A, Muzashvili T, Perrone A, Pizza C, Kemertelidze E, Piacente S (2010) Steroidal glycosides from Ruscus ponticus. Phytochemistry 72:651–661
Naveed MA, Riaz N, Saleem M, Jabeen B, Ashraf M, Ismail T, Jabbar A (2014) Longipetalosides A–C, new steroidal saponins from Tribulus longipetalus. Steroids 83:45–51
Nelson D (2006) Plant cytochrome P450 s from moss to poplar. Phytochem Rev 5:193–204
Nian H, Qin LP, Chen WS, Zhang QY, Zheng HC, Wang Y (2006) Protective effect of steroidal saponins from rhizome of Anemarrhena asphodeloides on ovariectomy-induced bone loss in rats. Acta Pharmacol Sin 27:728–734
Nikam TD, Ebrahimi MA, Patil VA (2009) Embryogenic callus culture of Tribulus terrestris L. a potential source of harmaline, harmine and diosgenin. Plant Biotechnol Rep 3:243–250
Nohara T, Ono M, Ikeda T, Fujiwara Y, El-Aasr M (2010) The tomato saponin, esculeoside A. J Nat Prod 73:1734–1741
Nohara T, Fujiwara Y, Zhou JR, Urata J, Ikeda T, Murakami K, El-Aasr M, Ono M (2015) Saponins, esculeosides B-1 and B-2, in tomato juice and sapogenol, esculeogenin B1. Chem Pharm Bull (Tokyo) 63:848–850
Ohnishi T, Yokota T, Mizutani M (2009) Insights into the function and evolution of P450 s in plant steroid metabolism. Phytochemistry 70:1918–1929
Ohno M, Ono M, Nohara T (2011) New solanocapsine-type tomato glycoside from ripe fruit of Solanum lycopersicum. Chem Pharm Bull (Tokyo) 59:1403–1405
Ohtsuki T, Sato M, Koyano T, Kowithayakorn T, Kawahara N, Goda Y, Ishibashi M (2006) Steroidal saponins from Calamus insignis, and their cell growth and cell cycle inhibitory activities. Bioorg Med Chem 14:659–665
Osbourn AE (1996) Preformed antimicrobial compounds and plant defense against fungal attack. Plant Cell 8:1821–1831
Osbourn AE (2003) Saponins in cereals. Phytochemistry 62:1–4
Palazón J, Moyano E, Bonfill M, Osuna LT, Cusidó RM, Pinol MT (2006) Effect of organogenesis on steroidal saponin biosynthesis in calli cultures of Ruscus aculeatus. Fitoterapia 77:216–220
Pan X, Chen M, Liu Y, Wang Q, Zeng L, Li L, Liao Z (2008) A new isopentenyl diphosphate isomerase gene from Camptotheca acuminata: cloning, characterization and functional expression in Escherichia coli. DNA Seq 19:98–105
Pan ZH, Li Y, Liu JL, Ning DS, Li DP, Wu XD, Wen YX (2012) A cytotoxic cardenolide and a saponin from the rhizomes of Tupistra chinensis. Fitoterapia 83:1489–1493
Pang X, Wen D, Zhao Y, Xiong CQ, Wang XQ, Yu LY, Ma BP (2015) Steroidal saponins obtained by biotransformation of total furostanol glycosides from Dioscorea zingiberensis with Absidia coerulea. Carbohydr Res 402:236–240
Paquette SM, Bak S, Feyereisen R (2000) Intron–exon organization and phylogeny in a large superfamily, the paralogous cytochrome P450 genes of Arabidopsis thaliana. DNA Cell Biol 19:307–317
Pecio Ł, Jędrejek D, Masullo M, Piacente S, Oleszek W, Stochmal A (2012) Revised structures of avenacosides A and B and a new sulfated saponin from Avena sativa L. Magn Reson Chem 50:755–758
Peng YR, Li YB, Liu XD, Zhang JF, Duan JA (2008) Antitumor activity of C-21 steroidal glycosides from Cynanchum auriculatum Royle ex Wight. Phytomedicine 15:1016–1020
Pereira BD, Valente AP, Parente JP (2004) A new steroidal saponin from Agave shrevei. Nat Prod Res 20:385–390
Pérez AJ, Calle JM, Simonet AM, Guerra JO, Stochmal A, Macías FA (2013) Bioactive steroidal saponins from Agave offoyana flowers. Phytochemistry 95:298–307
Pérez AJ, Simonet AM, Calle JM, Pecio Ł, Guerra JO, Stochmal A, Macías FA (2014) Phytotoxic steroidal saponins from Agave offoyana leaves. Phytochemistry 105:92–100
Perez-Labrada K, Brouard I, Estévez S, Marrero MT, Estévez F, Bermejo J, Rivera DG (2012) New insights into the structure–cytotoxicity relationship of spirostan saponins and related glycosides. Bioorg Med Chem 20:2690–2700
Phillips MA, D’Auria JC, Gershenzon J, Pichersky E (2008) The Arabidopsis thaliana type I isopentenyl diphosphate isomerases are targeted to multiple subcellular compartments and have overlapping functions in isoprenoid biosynthesis. Plant Cell 20:677–696
Pise MV, Rudra JA, Upadhyay A (2015) Immunomodulatory potential of shatavarins produced from Asparagus racemosus tissue cultures. J Nat Sci Biol Med 6:415–420
Qin Y, Wu X, Huang W, Gong G, Li D, He Y, Zhao Y (2009) Acute toxicity and sub-chronic toxicity of steroidal saponins from Dioscorea zingiberensis C.H.Wright in rodents. J Ethnopharmacol 126:543–550
Qin XJ, Sun DJ, Ni W, Chen CX, Hua Y, He L, Liu HY (2012) Steroidal saponins with antimicrobial activity from stems and leaves of Paris polyphylla var. yunnanensis. Steroids 77:1242–1248
Qin XJ, Yu MY, Ni W, Yan H, Chen CX, Cheng YC, He L, Liu HY (2016) Steroidal saponins from stems and leaves of Paris polyphylla var. yunnanensis. Phytochemistry 121:20–29
Qu Y, Zhang Y, Pei L, Wang Y, Gao L, Huang Q, Ojika M, Sakagami Y, Qi J (2011) New neuritogenic steroidal saponin from Ophiopogon japonicus (Thunb.) Ker-Gawl. Biosci Biotechnol Biochem 75:1201–1204
Rahman SU, Ismail M, Khurram M, Haq IU (2015) Pharmacognostic and ethnomedicinal studies on Trillium govanianum. Pak J Bot 47:187–192
Ramalingam M, Kim SJ (2016) Pharmacological activities and applications of spicatoside A. Biomol Ther (Seoul) 24:469–474
Ramos-Valdivia AC, van der Heijden R, Verpoorte R, Camara B (1997) Purification and characterization of two isoforms of isopentenyl-diphosphate isomerase from elicitor-treated Cinchona robusta cells. Eur J Biochem 249:161–170
Razdan S, Bhat WW, Rana S, Dhar N, Lattoo SK, Dhar RS, Vishwakarma RA (2013) Molecular characterization and promoter analysis of squalene epoxidase gene from Withania somnifera (L.) Dunal. Mol Biol Rep 40:905–916
Rezgui A, Mitaine-Offer AC, Pertuit D, Miyamoto T, Tanaka C, Delemasure S, Dutartre P, Lacaille-Dubois MA (2013) Steroidal saponins from Dracaena marginata. Nat Prods Commun 8:157–160
Rezgui A, Mitaine-Offer AC, Paululat T, Delemasure S, Dutartre P, Lacaille-Dubois MA (2014) Cytotoxic steroidal glycosides from Allium flavum. Fitoterapia 93:121–125
Rezgui A, Mitaine-Offer AC, Miyamoto T, Tanaka C, Lacaille-Dubois MA (2015) Spirostane-type saponins from Dracaena fragrans “Yellow Coast”. Nat Prod Commun 10:37–38
Ribeiro PR, Araújo AJ, Costa-Lotufo LV, Braz-Filho R, Nobre Junior HV, da Silva CR, de Andrade Neto JB, Silveira ER, Lima MA (2016) Spirostanol glucosides from the leaves of Cestrum laevigatum L. Steroids 106:35–40
Rojas R, Alba J, Magaña-Plaza I, Cruz F, Ramos-Valdivia AC (1999) Stimulated production of diosgenin in Dioscorea galeottiana cell suspension cultures by abiotic and biotic factors. Biotechnol Lett 21:907–911
Rong Q, Xu Q, Liu C, Huang L (2011) Cloning and characterization of 3-hydroxy-3-methylglutary CoA reductase cDNA of Glycyrrhiza uralensis. Zhongguo Zhong Yao Za Zhi 36:1275–1279
Rong Q, Jiang D, Chen Y, Shen Y, Yuan Q, Lin H, Zha L, Zhang Y, Huang L (2016) Molecular cloning and functional analysis of squalene synthase 2 (SQS2) in Salvia miltiorrhiza Bunge. Front Plant Sci 7:1274
Sautour M, Miyamoto T, Lacaille-Dubois MA (2006) Bioactive steroidal saponins from Smilax medica. Planta Med 72:667–670
Sautour M, Miyamoto T, Lacaille-Dubois MA (2007) Steroidal saponins from Asparagus acutifolius. Phytochemistry 68:2554–2562
Sawai S, Saito K (2011) Triterpenoid biosynthesis and engineering in plants. Front Plant Sci 2:25
Schuler M (1996) Plant cytochrome P450 monooxygenases. Crit Rev Plant Sci 15:235–284
Schulte AE, van der Heijden R, Verpoorte R (2000) Purification and characterization of mevalonate kinase from suspension-cultured cells of Catharanthus roseus (L) G Don. Arch Biochem Biophys 378:287–298
Shao B, Guo H, Cui Y, Ye M, Han J, Guo D (2007) Steroidal saponins from Smilax china and their anti-inflammatory activities. Phytochemistry 68:623–630
Sharma U, Saini R, Kumar N, Singh B (2009) Steroidal saponins from Asparagus racemosus. Chem Pharm Bull (Tokyo) 57:890–893
Sharma U, Kumar N, Singh B (2012) Furostanol saponin and diphenylpentendiol from the roots of Asparagus racemosus. Nat Prod Commun 7:995–998
Sharma M, Ahuja A, Gupta R, Mallubhotla S (2015) Enhanced bacoside production in shoot cultures of Bacopa monnieri under the influence of abiotic elicitors. Nat Prod Res 29:745–749
Shen G, Pang Y, Wu W, Liao Z, Zhao L, Sun X, Tang K (2006) Cloning and characterization of a root-specific expressing gene encoding 3-hydroxy-3-methylglutaryl coenzyme A reductase from Ginkgo biloba. Mol Biol Rep 33:117–127
Shen S, Chen CJ, Bu R, Ga L, Li GY, Tan Y, Li X, Wang JH (2011) Three new steroidal saponins from Fritillaria pallidiflora. J Asian Nat Prod Res 13:1014–1022
Shen S, Li G, Huang J, Chen C, Ren B, Lu G, Tan Y, Zhang J, Li X, Wang J (2012) Steroidal saponins from Fritillaria pallidiflora Schrenk. Fitoterapia 83:785–794
Shen HY, Zuo WJ, Wang H, Zhao YX, Guo ZK, Luo Y, Li XN, Dai HF, Mei WL (2014) Steroidal saponins from dragon’s blood of Dracaena cambodiana. Fitoterapia 94:94–101
Shen T, Qiu F, Chen M, Lan XZ, Liao ZH (2015) Cloning and functional characterization of a cDNA encoding isopentenyl diphosphate isomerase involved in taxols biosynthesis in Taxus media. Yao Xue Xue Bao 50:621–626
Shu W, Wu C, Zhang Y, Ye WC, Zhou G (2013) Two new steroidal glycosides isolated from the aerial part of Solanum torvum Swartz. Nat Prod Res 27:1982–1986
Shwe HH, Aye M, Sein MM, Htay KT, Kreitmeier P, Gertsch J, Reiser O, Heilmann J (2010) Cytotoxic steroidal saponins from the rhizomes of Tacca integrifolia. Chem Biodivers 7:610–622
Si YA, Yan H, Ni W, Liu ZH, Lu TX, Cheng CX, Liu HY (2014) Two new steroidal saponins from Ypsilandra thibetica. Nat Prod Bioprospect 4:315–318
Singh P, Singh G, Bhandawat A, Singh G, Parmar R, Seth R, Sharma RK (2017) Spatial transcriptome analysis provides insights of key gene(s) involved in steroidal saponin biosynthesis in medicinally important herb Trillium govanianum. Sci Rep 7:45295
Skhirtladze A, Perrone A, Montoro P, Benidze M, Kemertelidze E, Pizza C, Piacente S (2011) Steroidal saponins from Yucca gloriosa L. rhizomes: LC–MS profiling, isolation and quantitative determination. Phytochemistry 72:126–135
Sobolewska D, Janeczko Z, Kisiel W, Podolak I, Galanty A, Trojanowska D (2006) Steroidal glycosides from the underground parts of Allium ursinum L. and their cytostatic and antimicrobial activity. Acta Pol Pharm 63:219–223
Sobolewska D, Michalska K, Podolak I, Grabowska K (2016) Steroidal saponins from the genus Allium. Phytochem Rev 15:1–35
Su L, Chen G, Feng SG, Wang W, Li ZF, Chen H, Liu YX, Pei YH (2009) Steroidal saponins from Tribulus terrestris. Steroids 74:399–403
Sun LX, Fu WW, Li W, Bi KS, Wang MW (2006) Diosgenin glucuronides from Solanum lyratum and their cytotoxicity against tumor cell lines. Z Naturforsch C 61:171–176
Sun Z, Huang X, Kong L (2010) A new steroidal saponin from the dried stems of Asparagus officinalis L. Fitoterapia 81:210–213
Sun K, Cao S, Pei L, Matsuura A, Xiang L, Qi J (2013) A steroidal saponin from Ophiopogon japonicus extends the lifespan of yeast via the pathway involved in SOD and UTH1. Int J Mol Sci 14:4461–4475
Sun CL, Ni W, Yan H, Liu ZH, Yang L, Si YA, Hua Y, Chen CX, He L, Zhao JH, Liu HY (2014) Steroidal saponins with induced platelet aggregation activity from the aerial parts of Paris verticillata. Steroids 92:90–95
Suzuki M, Kamide Y, Nagata N, Seki H, Ohyama K, Kato H, Masuda K, Sato S, Kato T, Tabata S, Yoshida S, Muranaka T (2004) Loss of function of 3-hydroxy-3-methylglutaryl coenzyme A reductase 1 (HMG1) in Arabidopsis leads to dwarfing, early senescence and male sterility, and reduced sterol levels. Plant J 37:750–761
Tabopda TK, Mitaine-Offer AC, Tanaka C, Miyamoto T, Mirjolet JF, Duchamp O, Ngadjui BT, Lacaille-Dubois MA (2014) Steroidal saponins from Dioscorea preussii. Fitoterapia 97:198–203
Tabopda TK, Mitaine-Offer AC, Paululat T, Delemasure S, Dutartre P, Ngadjui BT, Lacaille-Dubois MA (2016) Steroidal saponins from Chlorophytum deistelianum. Phytochemistry 126:34–40
Tan DW, Kang LP, Lü N, Zhang J, Ma BP (2006) Study on steroidal saponins of Dioscorea septemloba thumb. Zhong Yao Cai 29:1176–1179
Tang W, Newton RJ (2006) Mevalonate kinase activity during different stages of plant regeneration from nodular callus cultures in white pine (Pinus strobus). Tree Physiol 26:195–200
Tapondjou LA, Ponou KB, Teponno RB, Mbiantcha M, Djoukeng JD, Nguelefack TB, Watcho P, Cadenas AG, Park HJ (2008) In vivo anti-inflammatory effect of a new steroidal saponin, mannioside A, and its derivatives isolated from Dracaena mannii. Arch Pharm Res 31:653–658
Tapondjou LA, Jenett-Siems K, Böttger S, Melzig MF (2013) Steroidal saponins from the flowers of Dioscorea bulbifera var. sativa. Phytochemistry 95:341–350
Tapondjou LA, Siems KJ, Böttger S, Melzig MF (2015) Steroidal saponins from the mesocarp of the fruits of Raphia farinifera (Arecaceae) and their cytotoxic activity. Nat Prod Commun 10:1941–1944
Temraz AE, Gindi OD, Kadry HA, De Tommasi N, Braca A (2006) Steroidal saponins from the aerial parts of Tribulus alatus Del. Phytochemistry 67:1011–1018
Timité G, Mitaine-Offer AC, Miyamoto T, Tanaka C, Mirjolet JF, Duchamp O, Lacaille-Dubois MA (2013) Structure and cytotoxicity of steroidal glycosides from Allium schoenoprasum. Phytochemistry 88:61–66
Tiski I, Marraccini P, Pot D, Vieira LG, Pereira LF (2011) Characterization and expression of two cDNA encoding 3-hydroxy-3-methylglutaryl coenzyme A reductase isoforms in coffee (Coffea arabica L.). OMICS 15:719–727
Tong QY, He Y, Zhao QB, Qing Y, Huang W, Wu XH (2012) Cytotoxicity and apoptosis-inducing effect of steroidal saponins from Dioscorea zingiberensis Wright against cancer cells. Steroids 77:1219–1227
Tong YR, Su P, Zhao YJ, Zhang M, Wang XJ, Hu TY, Gao W, Huang LQ (2015) Cloning and expression analysis of 4- (cytidine-5-diphospho) -2-C-methyl-D-erythritol kinase gene in Tripterygium wilfordii. Zhongguo Zhong Yao Za Zhi 40:4165–4170
Tong Y, Zhang M, Su P, Zhao Y, Wang X, Zhang X, Gao W, Huang L (2016) Cloning and functional characterization of an isopentenyl diphosphate isomerase gene from Tripterygium wilfordii. Biotechnol Appl Biochem 63:863–869
Uchida H, Sugiyama R, Nakayachi O, Takemura M, Ohyama K (2007) Expression of the gene for sterol-biosynthesis enzyme squalene epoxidase in parenchyma cells of the oil plant, Euphorbia tirucalli. Planta 226:1109–1115
Upadhyay S, Phukan UJ, Mishra S, Shukla RK (2014) De novo leaf and root transcriptome analysis identified novel genes involved in steroidal sapogenin biosynthesis in Asparagus racemosus. BMC Genom 15:746
Vieira Júnior GM, da Rocha CQ, de Souza Rodrigues T, Hiruma-Lima CA, Vilegas W (2015) New steroidal saponins and antiulcer activity from Solanum paniculatum L. Food Chem 186:160–167
Vincken JP, Heng L, de Groot A, Gruppen H (2007) Saponins, classification and occurrence in the plant kingdom. Phytochemistry 68:275–297
Vishwakarma RK, Patel KA, Sonawane P, Singh S, Ruby Kumari U, Agrawal DC, Khan BM (2012) Molecular characterization of farnesyl pyrophosphate synthase from Bacopa monniera by comparative modeling and docking studies. Bioinformation 8:1075–1081
Waheed A, Barker J, Barton SJ, Owen CP, Ahmed S, Carew MA (2012) A novel steroidal saponin glycoside from Fagonia indica induces cell-selective apoptosis or necrosis in cancer cells. Eur J Pharm Sci 47:464–473
Wang Y, McAllister TA (2010) A modified spectrophotometric assay to estimate deglycosylation of steroidal saponin to sapogenin by mixed ruminal microbes. J Sci Food Agric 90:1811–1818
Wang W, Meng H (2015) Cytotoxic, anti-inflammatory and hemostatic spirostane-steroidal saponins from the ethanol extract of the roots of Bletilla striata. Fitoterapia 101:12–18
Wang Y, Guo B, Zhang F, Yao H, Miao Z, Tang K (2007) Molecular cloning and functional analysis of the gene encoding 3-hydroxy-3-methylglutaryl coenzyme A reductase from hazel (Corylus avellana L. Gasaway). J Biochem Mol Biol 40:861–869
Wang D, Li D, Zhu W, Zhang J, Peng P (2009a) Steroidal saponins from the rhizomes of Polygonatum odoratum. Nat Prod Res 23:940–947
Wang Y, Qiu C, Zhang F, Guo B, Miao Z, Sun X, Tang K (2009b) Molecular cloning, expression profiling and functional analyses of a cDNA encoding isopentenyl diphosphate isomerase from Gossypium barbadense. Biosci Rep 29:111–119
Wang YZ, Feng B, Huang HZ, Kang LP, Cong Y, Zhou WB, Zou P, Cong YW, Song XB, Ma BP (2010) Glucosylation of steroidal saponins by cyclodextrin glucanotransferase. Planta Med 76:1724–1731
Wang K, Sasaki T, Li W, Li Q, Wang Y, Asada Y, Kato H, Koike K (2011a) Two novel steroidal alkaloid glycosides from the seeds of Lycium barbarum. Chem Biodivers 8:2277–2284
Wang KW, Zhang H, Shen LQ, Wang W (2011b) Novel steroidal saponins from Liriope graminifolia (Linn.) Baker with anti-tumor activities. Carbohydr Res 346:253–258
Wang H, Zhai Z, Li N, Jin H, Chen J, Yuan S, Wang L, Zhang J, Li Y, Yun J, Fan J, Yi J, Ling R (2013) Steroidal saponin of Trillium tschonoskii reverses multidrug resistance of hepatocellular carcinoma. Phytomedicine 20:985–991
Wang JJ, Liu YX, Wen D, Yu HS, Kang LP, Pang X, Ma BP, Chen YD (2014a) Study on steroidal saponins from Dioscorea zingiberensis and their platelet aggregation activities. Zhongguo Zhong Yao Za Zhi 39:3782–3787
Wang QJ, Zheng LP, Zhao PF, Zhao YL, Wang JW (2014b) Cloning and characterization of an elicitor-responsive gene encoding 3-hydroxy-3-methylglutaryl coenzyme A reductase involved in 20-hydroxyecdysone production in cell cultures of Cyanotis arachnoidea. Plant Physiol Biochem 84:1–9
Wang Y, Li X, Sun H, Yi K, Zheng J, Zhang J, Hao Z (2014c) Biotransformation of steroidal saponins in sisal (Agave sisalana Perrine) to tigogenin by a newly isolated strain from a karst area of Guilin, China. Biotechnol Biotechnol Equip 28:1024–1033
Wang P, Wei Y, Fan Y, Liu Q, Wei W, Yang C, Zhang L, Zhao G, Yue J, Yan X, Zhou Z (2015a) Production of bioactive ginsenosides Rh2 and Rg3 by metabolically engineered yeasts. Metab Eng 29:97–105
Wang X, Chen D, Wang Y, Xie J (2015b) De novo transcriptome assembly and the putative biosynthetic pathway of steroidal sapogenins of Dioscorea composita. PLoS ONE 10:e0124560
Wang YH, Niu HM, Zhang ZY, Hu XY, Li H (2015c) Medicinal values and their chemical bases of Paris. Zhongguo Zhong Yao Za Zhi 40:833–839
Wang Y, Xu L, Lou LL, Song SJ, Yao GD, Ge MY, Hayashi T, Tashiro SI, Onodera S, Ikejima T (2016a) Timosaponin AIII induces apoptosis and autophagy in human melanoma A375-S2 cells. Arch Pharm Res 40:69–78
Wang ZF, Wang BB, Zhao Y, Wang FX, Sun Y, Guo RJ, Song XB, Xin HL, Sun XG (2016b) Furostanol and spirostanol saponins from Tribulus terrestris. Molecules 21:E429
Williams JR, Gong H (2007) Biological activities and syntheses of steroidal saponins: the shark-repelling pavoninins. Lipids 42:77–86
Wu JJ, Cheng KW, Zuo XF, Wang MF, Li P, Zhang LY, Wang H, Ye WC (2010) Steroidal saponins and ecdysterone from Asparagus filicinus and their cytotoxic activities. Steroids 75:734–739
Wu X, Wang L, Wang GC, Wang H, Dai Y, Ye WC, Li YL (2012a) New steroidal saponins and sterol glycosides from Paris polyphylla var. yunnanensis. Planta Med 78:1667–1675
Wu X, Wang L, Wang H, Dai Y, Ye WC, Li YL (2012b) Steroidal saponins from Paris polyphylla var. yunnanensis. Phytochemistry 81:133–143
Wu XH, Wang CZ, Zhang J, Wang SQ, Han L, Zhang YW, Yuan CS (2014a) Effects of smilaxchinoside A and smilaxchinoside C, two steroidal glycosides from Smilax riparia, on hyperuricemia in a mouse model. Phytother Res 28:1822–1828
Wu XH, Zhang J, Wang SQ, Yang VC, Anderson S, Zhang YW (2014b) Riparoside B and timosaponin J, two steroidal glycosides from Smilax riparia, resist to hyperuricemia based on URAT1 in hyperuricemic mice. Phytomedicine 21:1196–1201
Xiao X, Zou J, Bui-Nguyen TM, Bai P, Gao L, Liu J, Liu S, Xiao J, Chen X, Zhang X, Wang H (2012) Paris saponin II of Rhizoma Paridis—a novel inducer of apoptosis in human ovarian cancer cells. Biosci Trends 6:201–211
Xie BB, Liu HY, Ni W, Chen CX, Lü Y, Wu L, Zheng QT (2006) Five new steroidal compounds from Ypsilandra thibetica. Chem Biodivers 3:1211–1218
Xie BB, Liu HY, Ni W, Chen CX (2009) Ypsilandrosides C–G, five new spirostanol saponins from Ypsilandra thibetica. Steroids 74:950–955
Xie WL, Jiang R, Shen XL, Chen ZY, Deng XM (2015) Diosgenin attenuates hepatic stellate cell activation through transforming growth factor-β/Smad signaling pathway. Int J Clin Exp Med 8:20323–20329
Xing Z, Long Y, Lao F, He S, Liang N, Li B (2012) Effect of endophytic fungi on expression amount of key enzyme genes in saponins biosynthesis and Eleutherococcus senticosus saponins content. Zhongguo Zhong Yao Za Zhi 37:2041–2045
Xu DP, Hu CY, Wei L, Pang ZJ (2007a) Isolation and structure determination of steroidal saponin from Dioscorea zingiberensis. Yao Xue Xue Bao 42:1162–1165
Xu FQ, Zhong HM, Liu HY, Liu HQ, Chen CX (2007b) Steroidal saponins from Lysimachia Paridiformis. J Asian Nat Prod Res 9:493–497
Xu TH, Xu YJ, Xie SX, Zhao HF, Han D, Li Y, Niu JZ, Xu DM (2008) A novel steroidal glycoside, ophiofurospiside A from Ophiopogon japonicus (Thunb.) Ker-Gawl. J Asian Nat Prod Res 10:415–418
Xu DP, Hu CY, Wang L, Wang XC, Pang ZJ (2009a) Isolation and structure determination of steroidal saponin from Dioscorea zingiberensis. Yao Xue Xue Bao 44:56–59
Xu DP, Hu CY, Zhang Y (2009b) Two new steroidal saponins from the rhizome of Polygonatum sibiricum. J Asian Nat Prod Res 11:1–6
Xu YJ, Xu TH, Liu Y, Xie SX, Si YS, Xu DM (2009c) Two new steroidal glucosides from Tribulus terrestris L. J Asian Nat Prod Res 11:548–553
Xu M, Zhang YJ, Li XC, Jacob MR, Yang CR (2010) Steroidal saponins from fresh stems of Dracaena angustifolia. J Nat Prod 73:1524–1528
Xu Y, Liu J, Liang L, Yang X, Zhang Z, Gao Z, Sui C, Wei J (2014) Molecular cloning and characterization of three cDNAs encoding 1-deoxy-d-xylulose-5-phosphate synthase in Aquilaria sinensis (Lour.) Gilg. Plant Physiol Biochem 82:133–141
Yada H, Kimura T, Suzuki M, Ohnishi-Kameyama M, Shinmoto H (2010) New steroidal saponin from Hosta sieboldiana. Biosci Biotechnol Biochem 74:861–864
Yan Y, Zhang JX, Liu KX, Huang T, Yan C, Huang LJ, Liu S, Mu SZ, Hao XJ (2014) Seco-pregnane steroidal glycosides from the roots of Cynanchum atratum and their anti-TMV activity. Fitoterapia 97:50–63
Yang QX, Yang CR (2006) Cytotoxic steroidal saponins from Polygonatum punctatum. Chem Biodivers 3:1349–1355
Yang SL, Liu XK, Wu H, Wang HB, Qing C (2009) Steroidal saponins and cytoxicity of the wild edible vegetable—Smilacina atropurpurea. Steroids 74:7–12
Yang J, Wang P, Wu W, Zhao Y, Idehen E, Sang S (2016) Steroidal saponins in oat bran. J Agric Food Chem 64:1549–1556
Ye Y, Chen F, Sun H, Li X, Xu S (2008) Stemucronatoside K, a novel C(21) steroidal glycoside from Stephanotis mucronata, inhibited the cellular and humoral immune response in mice. Int Immunopharmacol 8:1231–1238
Ye Y, Qu Y, Tang R, Cao S, Yang W, Xiang L, Qi J (2013) Three new neuritogenic steroidal saponins from Ophiopogon japonicus (Thunb.) Ker-Gawl. Steroids 78:1171–1176
Yen CT, Lee CL, Chang FR, Hwang TL, Yen HF, Chen CJ, Chen SL, Wu YC (2012) Indiosides G–K: steroidal glycosides with cytotoxic and anti-inflammatory activities from Solanum violaceum. J Nat Prod 75:636–643
Yen PH, Chi VT, Kiem PV, Tai BH, Quang TH, Nhiem NX, Anh HL, Ban NK, Thanh BV, Minh CV, Park S, Kim SH (2016) Spirostanol saponins from Tacca vietnamensis and their anti-inflammatory activity. Bioorg Med Chem Lett S0960–894:30533–30539
Yin HX, Xue D, Bai N, Chen C, Chen Y, Zhang H (2008) Isolation and identification of major steroidal saponins of Paris polyphylla Smith var stenophylla Franch. Sichuan Da Xue Xue Bao Yi Xue Ban 39:485–488
Yokosuka A, Mimaki Y (2009) Steroidal saponins from the whole plants of Agave utahensis and their cytotoxic activity. Phytochemistry 70:807–815
Yokosuka A, Jitsuno M, Yui S, Yamazaki M, Mimaki Y (2009) Steroidal glycosides from Agave utahensis and their cytotoxic activity. J Nat Prod 72:1399–1404
Yoon KD, Chin YW, Yang MH, Choi J, Kim J (2012) Application of high-speed countercurrent chromatography–evaporative light scattering detection for the separation of seven steroidal saponins from Dioscorea villosa. Phytochem Anal 23:462–468
Yu JQ, Deng AJ, Qin HL (2013) Nine new steroidal glycosides from the roots of Cynanchum stauntonii. Steroids 78:79–90
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 11:213–218
Yuan JC, Zhang J, Wang FX, Pang X, Zhao Y, Xiong CQ, Ma BP (2014) New steroidal glycosides from the rhizome of Anemarrhena asphodeloides. J Asian Nat Prod Res 16:901–909
Yuan YL, Guo CR, Cui LL, Ruan SX, Zhang CF, Ji D, Yang ZL, Li F (2015) Timosaponin B-II ameliorates diabetic nephropathy via TXNIP, mTOR, and NF-κB signaling pathways in alloxan-induced mice. Drug Des Devel Ther 9:6247–6258
Zeng KW, Song FJ, Li N, Dong X, Jiang Y, Tu PF (2015) ASC, a bioactive steroidal saponin from Ophitopogin japonicas, inhibits angiogenesis through interruption of Src tyrosine kinase-dependent matrix metalloproteinase pathway. Basic Clin Pharmacol Toxicol 116:115–123
Zha L, Liu S, Su P, Yuan Y, Huang L (2016) Cloning, prokaryotic expression and functional analysis of squalene synthase (SQS) in Magnolia officinalis. Protein Expr Purif 120:28–34
Zhang Y, Li HZ, Zhang YJ, Jacob MR, Khan SI, Li XC, Yang CR (2006) Atropurosides A–G, new steroidal saponins from Smilacina atropurpurea. Steroids 71:712–719
Zhang Y, Zhang YJ, Jacob MR, Li XC, Yang CR (2008) Steroidal saponins from the stem of Yucca elephantipes. Phytochemistry 69:264–270
Zhang L, Liu JY, Xu LZ, Yang SL (2009a) Chantriolide C, a new withanolide glucoside and a new spirostanol saponin from the rhizomes of Tacca chantrieri. Chem Pharm Bull (Tokyo) 57:1126–1128
Zhang T, Liu H, Liu XT, Chen XQ, Wang Q (2009b) Steroidal saponins from the rhizomes of Paris delavayi. Steroids 74:809–813
Zhang LJ, Yu HS, Kang LP, Feng B, Quan B, Song XB, Ma BP, Kang TG (2012a) Two new steroidal saponins from the biotransformation product of the rhizomes of Dioscorea nipponica. J Asian Nat Prod Res 14:640–646
Zhang T, Kang LP, Yu HS, Liu YX, Zhao Y, Xiong CQ, Zhang J, Zou P, Song XB, Liu C, Ma BP (2012b) Steroidal saponins from the tuber of Ophiopogon japonicus. Steroids 77:1298–1305
Zhang C, Feng S, Zhang L, Ren Z (2013a) A new cytotoxic steroidal saponin from the rhizomes and roots of Smilax scobinicaulis. Nat Prod Res 27:1255–1260
Zhang J, Li H, Li H, Lu Z, Shi J, Xu Z (2013b) Screening and condition optimization of a strain for efficiently biotransformation of saponins in Dioscorea zingiberensis into diosgenin. Sheng Wu Gong Cheng Xue Bao 29:848–852
Zhang R, Huang B, Du D, Guo X, Xin G, Xing Z, Liang Y, Chen Y, Chen Q, He Y, Huang W (2013c) Anti-thrombosis effect of diosgenyl saponins in vitro and in vivo. Steroids 78:1064–1070
Zhang H, Chen L, Kou JP, Zhu DN, Qi J, Yu BY (2014a) Steroidal sapogenins and glycosides from the fibrous roots of Polygonatum odoratum with inhibitory effect on tissue factor (TF) procoagulant activity. Steroids 89:1–10
Zhang L, Wang JT, Zhang DW, Zhang G, Guo SX (2014b) Molecular characterization of a HMG-CoA reductase gene from a rare and endangered medicinal plant, Dendrobium officinale. Yao Xue Xue Bao 49:411–418
Zhang H, Su YF, Yang FY (2016a) Three new steroidal saponins from Helleborus thibetanus. Nat Prod Res 30:1724–1730
Zhang Y, Yang CR, Zhang YJ (2016b) Steroidal saponins from the rhizomes of Polygonatum prattii. J Asian Nat Prod Res 18:268–273
Zhao Y, Kang LP, Liu YX, Zhao Y, Xiong CQ, Ma BP, Dong FT (2007) Three new steroidal saponins from the rhizome of Paris polyphylla. Magn Reson Chem 45:739–744
Zhao Y, Kang LP, Liu YX, Liang YG, Tan DW, Yu ZY, Cong YW, Ma BP (2009) Steroidal saponins from the rhizome of Paris polyphylla and their cytotoxic activities. Planta Med 75:356–363
Zhao YJ, Chen X, Zhang M, Su P, Liu YJ, Tong YR, Wang XJ, Huang LQ, Gao W (2015) Molecular cloning and characterisation of farnesyl diphosphate synthase from Tripterygium wilfordii. PLoS ONE 10:e0125415
Zhao H, Tang Q, Mo C, Bai L, Tu D, Ma X (2017) Cloning and characterization of squalene synthase and cycloartenol synthase from Siraitia grosvenorii. Acta Pharm Sin B 7:215–222
Zheng J, Zheng Y, Zhi H, Dai Y, Wang N, Wu L, Fan M, Fang Y, Zhao S, Zhang K (2013) Two new steroidal saponins from Selaginella uncinata (Desv.) spring and their protective effect against anoxia. Fitoterapia 88:25–30
Zheng L, Zhou Y, Zhang JY, Song M, Yuan Y, Xiao YJ, Xiang T (2014) Two new steroidal saponins from the rhizomes of Dioscorea zingiberensis. Chin J Nat Med 12:142–147
Zhou LB, Chen DF (2008) Steroidal saponins from the roots of Asparagus filicinus. Steroids 73:83–87
Zhou X, He X, Wang G, Gao H, Zhou G, Ye W, Yao X (2006) Steroidal saponins from Solanum nigrum. J Nat Prod 69:1158–1163
Zhou LB, Chen TH, Bastow KF, Shibano M, Lee KH, Chen DF (2007) Filiasparosides A–D, cytotoxic steroidal saponins from the roots of Asparagus filicinus. J Nat Prod 70:1263–1267
Zhou ZL, Feng ZC, Fu CY, Zhang HL, Xia JM (2012) Steroidal and phenolic glycosides from the bulbs of Lilium pumilum DC and their potential Na +/K + ATPase inhibitory activity. Molecules 17:10494–10502
Zhu YL, Huang W, Ni JR, Liu W, Li H (2010) Production of diosgenin from Dioscorea zingiberensis tubers through enzymatic saccharification and microbial transformation. Appl Microbiol Biotechnol 85:1409–1416
Zhu L, Tan J, Wang B, Guan L, Liu Y, Zheng C (2011) In-vitro antitumor activity and antifungal activity of pennogenin steroidal saponins from Paris Polyphylla var. yunnanensis. Iran J Pharm Res 10:279–286
Zhu GL, Hao Q, Li RT, Li HZ (2014) Steroidal saponins from the roots of Asparagus cochinchinensis. Chin J Nat Med 12:213–217
Zou K, Wang J, Du M, Li Q, Tu G (2006) A pair of diastereoisomeric steroidal saponins from cytotoxic extracts of Tupistra chinensis rhizomes. Chem Pharm Bull (Tokyo) 54:1440–1442
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Upadhyay, S., Jeena, G.S., Shikha et al. Recent advances in steroidal saponins biosynthesis and in vitro production. Planta 248, 519–544 (2018). https://doi.org/10.1007/s00425-018-2911-0
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DOI: https://doi.org/10.1007/s00425-018-2911-0