Structure, Bioactivity and Analytical Methods for the Determination of Yucca Saponins

Yucca is one of the main sources of steroidal saponins, hence different extracts are commercialized for use as surfactant additives by beverage, animal feed, cosmetics or agricultural products. For a deeper understanding of the potential of the saponins that can be found in this genus, an exhaustive review of the structural characteristics, bioactivities and analytical methods that can be used with these compounds has been carried out, since there are no recent reviews on the matter. Thus, a total of 108 saponins from eight species of the genus Yucca have been described. Out of these, the bioactivity of 68 saponins derived from the isolation of Yucca or other genera has been evaluated. Regarding the evaluation and quality control of the saponins from this genus LC-MS technique is the most often used. Nevertheless, the development of methods for their routine analysis in commercial preparations are needed. Moreover, most of the studies found in the literature have been carried out on Y. schidigera extract, since is the most often used for commercial purposes. Only eight of the 50 species that belong to this genus have been studied, which clearly indicates that the identification of saponins present in Yucca genus is still an unresolved question.

[1]  M. Alagawany,et al.  Yucca schidigera Usage for Healthy Aquatic Animals: Potential Roles for Sustainability , 2021, Animals : an open access journal from MDPI.

[2]  M. Bryś,et al.  Saponins as Modulators of the Blood Coagulation System and Perspectives Regarding Their Use in the Prevention of Venous Thromboembolic Incidents , 2020, Molecules.

[3]  S. El-Hawary,et al.  LC–MS/MS and GC–MS profiling as well as the antimicrobial effect of leaves of selected Yucca species introduced to Egypt , 2020, Scientific Reports.

[4]  Yi Zhang,et al.  Identification and Structural Analysis of Spirostanol Saponin from Yucca schidigera by Integrating Silica Gel Column Chromatography and Liquid Chromatography/Mass Spectrometry Analysis , 2020, Molecules.

[5]  D. Y. Lee,et al.  Characterization of spirostanol glycosides and furostanol glycosides from anemarrhenae rhizoma as dual targeted inhibitors of 5-lipoxygenase and Cyclooxygenase-2 by employing a combination of affinity ultrafiltration and HPLC/MS. , 2020, Phytomedicine : international journal of phytotherapy and phytopharmacology.

[6]  Jing Xu,et al.  Steroidal saponins and sapogenins from fenugreek and their inhibitory activity against α-glucosidase , 2020, Steroids.

[7]  D. Shou,et al.  Timosaponin AIII attenuates inflammatory injury in AGEs-induced osteoblast and alloxan-induced diabetic osteoporosis zebrafish by modulating the RAGE/MAPK signaling pathways. , 2020, Phytomedicine : international journal of phytotherapy and phytopharmacology.

[8]  Min Liu,et al.  Identification of a novel BACE1 inhibitor, timosaponin A-III, for treatment of Alzheimer's disease by a cell extraction and chemogenomics target knowledgebase-guided method. , 2020, Phytomedicine : international journal of phytotherapy and phytopharmacology.

[9]  Wenjie Mei,et al.  Cardioprotective effects of timosaponin B-II isolated from Anemarrhena rhizome in a zebrafish model. , 2020, Die Pharmazie.

[10]  Qi Liu,et al.  Optimization of extraction for Anemarrhena asphodeloides Bge. using silica gel-based vortex-homogenized matrix solid-phase dispersion and rapid identification of antioxidant substances. , 2020, Journal of separation science.

[11]  Yiguang Jin,et al.  Nasal timosaponin BII dually sensitive in situ hydrogels for the prevention of Alzheimer's disease induced by lipopolysaccharides. , 2020, International journal of pharmaceutics.

[12]  Yun-fang Zhao,et al.  Cytotoxic steroidal saponins from the rhizome of Anemarrhena asphodeloides , 2019, Steroids.

[13]  R. Suzuki,et al.  Improving quality control of yucca extracts used as food additives by screening antimicrobial activity using NMR metabolomics , 2019, Journal of Natural Medicines.

[14]  R. H. Khalil,et al.  Estimating the effective level of Yucca schidigera extract for improvement of the survival, haematological parameters, immunological responses and Water quality of European seabass juveniles (dicentrarchus labrax) , 2019, Aquaculture Reports.

[15]  Jing-yi Tang,et al.  Antiangiogenesis effect of timosaponin AIII on HUVECs in vitro and zebrafish embryos in vivo , 2019, Acta Pharmacologica Sinica.

[16]  L. Herfindal,et al.  Cytotoxic saponins and other natural products from flowering tops of Narthecium ossifragum L. , 2019, Phytochemistry.

[17]  Zhe Wang,et al.  Furostanol saponins from Chinese onion induce G2/M cell-cycle arrest and apoptosis through mitochondria-mediate pathway in HepG2 cells , 2019, Steroids.

[18]  Y. Kim,et al.  The enhancing immune response and anti-inflammatory effects of Anemarrhena asphodeloides extract in RAW 264.7 cells. , 2019, Phytomedicine : international journal of phytotherapy and phytopharmacology.

[19]  Shaojiang Song,et al.  Timosaponin AIII, a steroidal saponin, exhibits anti-tumor effect on taxol-resistant cells in vitro and in vivo , 2019, Steroids.

[20]  Yun‐Cheol Na,et al.  Apoptosis and G2/M cell cycle arrest induced by a timosaponin A3 from Anemarrhena asphodeloides Bunge on AsPC-1 pancreatic cancer cells. , 2019, Phytomedicine : international journal of phytotherapy and phytopharmacology.

[21]  Hua Zhou,et al.  Discovery of cardio-protective constituents of Gualou Xiebai Decoction, a classical traditional Chinese medicinal formula. , 2019, Phytomedicine : international journal of phytotherapy and phytopharmacology.

[22]  P. Kiem,et al.  Degalactotigonin, a Steroidal Glycoside from Solanum nigrum, Induces Apoptosis and Cell Cycle Arrest via Inhibiting the EGFR Signaling Pathways in Pancreatic Cancer Cells , 2018, BioMed research international.

[23]  Guo-Dong Yao,et al.  Timosaponin AIII: A novel potential anti-tumor compound from Anemarrhena asphodeloides , 2018, Steroids.

[24]  Yi Zhang,et al.  Separation and Bioactive Assay of 25R/S-Spirostanol Saponin Diastereomers from Yucca schidigera Roezl (Mojave) Stems , 2018, Molecules.

[25]  Yu Jin,et al.  Anti-Inflammatory Activities of Compounds Isolated from the Rhizome of Anemarrhena asphodeloides , 2018, Molecules.

[26]  Hyun Pyo Kim,et al.  Therapeutic Potential of the Rhizomes of Anemarrhena asphodeloides and Timosaponin A-III in an Animal Model of Lipopolysaccharide-Induced Lung Inflammation , 2018, Biomolecules & therapeutics.

[27]  Yi Zhang,et al.  Spirostane-Type Saponins Obtained from Yucca schidigera , 2018, Molecules.

[28]  Ping Li,et al.  Comparison of &agr;‐glucosidase inhibitory effect and bioactive constituents of Anemarrhenae Rhizoma and Fibrous Roots , 2017, Journal of pharmaceutical and biomedical analysis.

[29]  Q. Jia,et al.  Degalactotigonin, a Natural Compound from Solanum nigrum L., Inhibits Growth and Metastasis of Osteosarcoma through GSK3β Inactivation–Mediated Repression of the Hedgehog/Gli1 Pathway , 2017, Clinical Cancer Research.

[30]  Deng-sheng Sun,et al.  Improved performance and immunological responses as a result of dietary Yucca schidigera extract supplementation in broilers , 2017 .

[31]  Yihai Wang,et al.  Potential Anti-inflammatory Steroidal Saponins from the Berries of Solanum nigrum L. (European Black Nightshade). , 2017, Journal of agricultural and food chemistry.

[32]  B. Simpson,et al.  Systematics and character evolution of the genus Yucca (Agavaceae): Evidence from morphology and molecular analyses , 2017 .

[33]  M. Roller,et al.  Rapid, cost-effective and accurate quantification of Yucca schidigera Roezl. steroidal saponins using HPLC-ELSD method. , 2017, Food chemistry.

[34]  F. Pedreschi,et al.  A systematic approach for the chromatographic fractionation and purification of major steroid saponins in commercial extracts of Yucca schidigera Roezl. , 2017, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[35]  Kyoung Jin Park,et al.  Allimacrosides A–E, new steroidal glycosides from Allium macrostemon Bunge , 2017, Steroids.

[36]  Chao Yang,et al.  Timosaponin AIII induces antiplatelet and antithrombotic activity via Gq-mediated signaling by the thromboxane A2 receptor , 2016, Scientific Reports.

[37]  U. K. Marelli,et al.  Evaluation of uttroside B, a saponin from Solanum nigrum Linn, as a promising chemotherapeutic agent against hepatocellular carcinoma , 2016, Scientific Reports.

[38]  Bikram Singh,et al.  Saponins of Agave: Chemistry and bioactivity. , 2016, Phytochemistry.

[39]  F. Pedreschi,et al.  TLC fingerprint of phenolics and saponins in commercial extracts of Yucca schidigera Roezl. , 2016 .

[40]  Jie Wu,et al.  Steroids from the rhizome of Anemarrhena asphodeloides and their cytotoxic activities. , 2016, Bioorganic & medicinal chemistry letters.

[41]  K. Nho,et al.  Induction of mitochondria-dependent apoptosis in HepG2 human hepatocellular carcinoma cells by timosaponin A-III. , 2016, Environmental toxicology and pharmacology.

[42]  T. Jha,et al.  Chenopodium album metabolites act as dual topoisomerase inhibitors and induce apoptosis in the MCF7 cell line , 2016 .

[43]  F. Pedreschi,et al.  MALDI-TOF mass spectrometry and reversed-phase HPLC-ELSD chromatography for structural and quantitative studies of major steroid saponins in commercial extracts of Yucca schidigera Roezl. , 2016, Journal of pharmaceutical and biomedical analysis.

[44]  C. Che,et al.  Identification of “sarsasapogenin-aglyconed” timosaponins as novel Aβ-lowering modulators of amyloid precursor protein processing† †Electronic supplementary information (ESI) available: ESI includes experimental procedures for biology and chemistry experiments, synthetic figures, NMR data and mass s , 2016, Chemical science.

[45]  S. Drusch,et al.  Interfacial Properties of Saponin Extracts and Their Impact on Foam Characteristics , 2016, Food Biophysics.

[46]  Zhan-qiang Ma,et al.  Cardioprotective effects of timosaponin B II from Anemarrhenae asphodeloides Bge on isoproterenol-induced myocardial infarction in rats. , 2015, Chemico-biological interactions.

[47]  Zhilong Chen,et al.  Electrospinning preparation of timosaponin B-II-Loaded PLLA nanofibers and their antitumor recurrence activities in vivo , 2015 .

[48]  Lifeng Han,et al.  Steroidal saponins from Tribulus terrestris. , 2014, Phytochemistry.

[49]  T. Jha,et al.  Spermicidal and Contraceptive Potential of Desgalactotigonin: A Prospective Alternative of Nonoxynol-9 , 2014, PloS one.

[50]  Y. Mimaki,et al.  Steroidal glycosides from the underground parts of Yucca glauca and their cytotoxic activities. , 2014, Phytochemistry.

[51]  Fei Li,et al.  Protective effects of timosaponin B-II on high glucose-induced apoptosis in human umbilical vein endothelial cells. , 2014, Environmental toxicology and pharmacology.

[52]  A. Stochmal,et al.  Bioactive steroidal saponins from Agave offoyana flowers. , 2013, Phytochemistry.

[53]  Jie Zhang,et al.  Analytical and semipreparative separation of 25 (R/S)-spirostanol saponin diastereomers using supercritical fluid chromatography. , 2013, Journal of separation science.

[54]  Chong-ren Yang,et al.  New Steroidal Saponins from the Leaves of Yucca elephantipes , 2013 .

[55]  S. Kim,et al.  Steroidal constituents from the leaves of Hosta longipes and their inhibitory effects on nitric oxide production. , 2013, Bioorganic & medicinal chemistry letters.

[56]  Fredyc Díaz Castillo,et al.  Actividad antiinflamatoria, antioxidante y antibacteriana de dos especies del género Tabebuia , 2013 .

[57]  C. Lavaud,et al.  Steroidal saponins from the leaves of Yucca de-smetiana and their in vitro antitumor activity: structure activity relationships through a molecular modeling approach , 2013, Medicinal Chemistry Research.

[58]  Seema Patel Yucca: A medicinally significant genus with manifold therapeutic attributes , 2012, Natural Products and Bioprospecting.

[59]  E. Ioannou,et al.  Desmettianosides A and B, bisdesmosidic furostanol saponins with molluscicidal activity from Yucca desmettiana , 2012, Steroids.

[60]  G. Gu,et al.  Facile Synthesis and Antitumor Activities of Timosaponin AIII and Its Analogs , 2012 .

[61]  L. Kang,et al.  Steroidal glycosides from the rhizomes of Anemarrhena asphodeloides and their antiplatelet aggregation activity. , 2012, Planta medica.

[62]  Ł. Pecio,et al.  Qualitative and quantitative analysis of steroidal saponins in crude extract and bark powder of Yucca schidigera Roezl. , 2011, Journal of agricultural and food chemistry.

[63]  Jenn-Wen Huang,et al.  Identification of the Solanum nigrum extract component involved in controlling cabbage black leaf spot disease. , 2011, Journal of agricultural and food chemistry.

[64]  S. Piacente,et al.  Steroidal saponins from Yucca gloriosa L. rhizomes: LC-MS profiling, isolation and quantitative determination. , 2011, Phytochemistry.

[65]  É. Kemertelidze,et al.  Steroidal Glycosides from the Leaves of Yucca Gloriosa L. , 2011 .

[66]  S. Piacente,et al.  Determination of steroidal glycosides in Yucca gloriosa flowers by LC/MS/MS. , 2010, Journal of pharmaceutical and biomedical analysis.

[67]  Yuxi Wang,et al.  A modified spectrophotometric assay to estimate deglycosylation of steroidal saponin to sapogenin by mixed ruminal microbes. , 2010, Journal of the science of food and agriculture.

[68]  G. G. Ortega,et al.  Evaluation of foam properties of saponin from Ilex paraguariensis A. St. Hil. (Aquifoliaceae) fruits , 2010 .

[69]  É. Kemertelidze,et al.  Steroid compounds from Yucca gloriosa L. introduced into Georgia and their applications , 2009, Pharmaceutical Chemistry Journal.

[70]  S. Kang,et al.  Rat Growth‐Hormone Release Stimulators from Fenugreek Seeds , 2008, Chemistry & biodiversity.

[71]  L. Kong,et al.  Steroids from the roots of Asparagus officinalis and their cytotoxic activity. , 2008, Journal of integrative plant biology.

[72]  Xing-Cong Li,et al.  Steroidal saponins from the stem of Yucca elephantipes. , 2008, Phytochemistry.

[73]  Guanghui Wang,et al.  New furostanol saponins from the bulbs of Allium macrostemon Bunge and their cytotoxic activity. , 2007, Die Pharmazie.

[74]  R. Park,et al.  A new steroidal saponin, yuccalan, from the leaves ofYucca smalliana , 2007, Archives of pharmacal research.

[75]  J. Vincken,et al.  Saponins, classification and occurrence in the plant kingdom. , 2007, Phytochemistry.

[76]  J. Simmons-Boyce,et al.  Steroidal Saponins and Sapogenins from the Agavaceae Family , 2007 .

[77]  S. Piacente,et al.  Furostanol saponins from Yucca gloriosa L. rhizomes , 2006 .

[78]  M. Lacaille‐Dubois,et al.  Bioactive steroidal saponins from Smilax medica. , 2006, Planta medica.

[79]  Xing-Cong Li,et al.  Antifungal Activity of C-27 Steroidal Saponins , 2006, Antimicrobial Agents and Chemotherapy.

[80]  P. Karpov,et al.  A steroid glycoside from the seeds ofYucca macrocarpa , 1998, Chemistry of Natural Compounds.

[81]  S. Piacente,et al.  Anti-inflammatory and anti-arthritic effects of yucca schidigera: A review , 2006, Journal of Inflammation.

[82]  S. Piacente,et al.  Saponins and Phenolics of Yucca schidigera Roezl: Chemistry and Bioactivity , 2005, Phytochemistry Reviews.

[83]  A. Favel,et al.  Antifungal activity of steroidal glycosides from Yucca gloriosa L. , 2005, Phytotherapy research : PTR.

[84]  J. van Staden,et al.  Biological activities and distribution of plant saponins. , 2004, Journal of ethnopharmacology.

[85]  T. Ohtsuki,et al.  New chlorogenin hexasaccharide isolated from Agave fourcroydes with cytotoxic and cell cycle inhibitory activities. , 2004, Bioorganic & medicinal chemistry.

[86]  P. Kintya,et al.  The structure of yuccoside E from Yucca filamentosa , 1975, Chemistry of Natural Compounds.

[87]  Ying-Jun Zhang,et al.  Spirostanol and furostanol glycosides from the fresh tubers of Polianthes tuberosa. , 2004, Journal of natural products.

[88]  T. Nohara,et al.  Cytotoxic activity of steroidal glycosides from solanum plants. , 2003, Biological & pharmaceutical bulletin.

[89]  Y. Ohizumi,et al.  Two steroidal saponins from Camassia cusickii induce L1210 cell death through the apoptotic mechanism. , 2001, Canadian journal of physiology and pharmacology.

[90]  Y. Mimaki,et al.  Cytotoxic activities and structure-cytotoxic relationships of steroidal saponins. , 2001, Biological & pharmaceutical bulletin.

[91]  S. Piacente,et al.  Steroidal saponins of Yucca schidigera Roezl. , 2001, Journal of agricultural and food chemistry.

[92]  V. Wray,et al.  Application of MS and NMR to the structure elucidation of complex sugar moieties of natural products: exemplified by the steroidal saponin from Yucca filamentosa L. , 2001, Phytochemistry.

[93]  H. Sakagami,et al.  Steroidal glycosides from the bulbs of Camassia leichtlinii and their cytotoxic activities. , 2001, Chemical & pharmaceutical bulletin.

[94]  Ricardo San Martin,et al.  Quality control of commercial quillaja (Quillaja saponaria Molina) extracts by reverse phase HPLC , 2000 .

[95]  K. Saito,et al.  Spectrophotometric determination of saponin in Yucca extract used as food additive. , 2000, Journal of AOAC International.

[96]  K. Yamasaki,et al.  Antiyeast steroidal saponins from Yucca schidigera (Mohave yucca), a new anti-food-deteriorating agent. , 2000, Journal of natural products.

[97]  P. Cheeke Actual and potential applications of Yucca schidigera and Quillaja saponaria saponins in human and animal nutrition , 2000 .

[98]  Y. Mimaki,et al.  Steroidal saponins from the rhizomes of Hosta sieboldii and their cytostatic activity on HL-60 cells. , 1998, Phytochemistry.

[99]  K. Koike,et al.  Steroidal glycosides from the underground parts of Hosta plantaginea var. japonica and their cytostatic activity on leukaemia HL-60 cells. , 1997, Phytochemistry.

[100]  C. Yang,et al.  Inhibitory effects of some steroidal saponins on human spermatozoa in vitro. , 1996, Planta medica.

[101]  J. Sakakibara,et al.  A spirostanol glycoside from Yucca aloifolia. , 1992, Phytochemistry.

[102]  J. Sakakibara,et al.  A new spirostanol glycoside from Yucca aloifolia , 1991 .

[103]  Y. Takaishi,et al.  12-Hydroxy steroidal glycosides from the caudex of Yucca gloriosa. , 1991, Phytochemistry.

[104]  Y. Takaishi,et al.  12-Keto steroidal glycosides from the caudex of Yucca gloriosa. , 1991, Phytochemistry.

[105]  O. P. Sati,et al.  A new molluscicidal spirostanol glycoside of Yucca aloifolia. , 1990 .

[106]  Y. Takaishi,et al.  The steroidal glycosides of the flowers of Yucca gloriosa , 1988 .

[107]  J C Baccou,et al.  Spectrophotometric method for the determination of total steroidal sapogenin. , 1977, The Analyst.

[108]  J. Ross,et al.  An apparatus for comparison of foaming properties of soaps and detergents , 1941 .