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Phytochemistry Reviews

, Volume 4, Issue 2–3, pp 177–190 | Cite as

Saponins and Phenolics of Yucca schidigera Roezl: Chemistry and Bioactivity

  • Sonia Piacente
  • Cosimo Pizza
  • Wieslaw Oleszek
Article

Abstract

Yucca schidigera (Agavaceae) is one of the major commercial source of steroidal saponins. Two products of yucca are available on the market. These include dried and finely powdered logs (yucca powder) or mechanically pressed and thermally condensed juice (yucca extract). These products possess the GRAS label which allows their use as foaming agent in soft drink (root beer), pharmaceutical, cosmetic, food, and feeding-stuffs industries. The main application of yucca products is in animal nutrition, in particular as a feed additive to reduce ammonia and fecal odors in animal excreta. The positive effects of dietary supplementation with yucca products on the growth rates, feed efficiency, and health of livestock seem to be due not only to the saponin constituents but also to other constituents. These observations prompted us to investigate the phenolic constituents of Y. schidigera. This study led to the isolation of resveratrol, trans-3,3′,5,5′-tetrahydroxy-4′-methoxystilbene, the sprirobiflavonoid larixinol along with novel phenolic derivatives with very unusual spirostructures, named yuccaols A–E and yuccaone A. Taking into account the multifunctional activities of resveratrol and the novelty of yuccaols A–E, structurally related to resveratrol, a program aimed to evaluate for yucca phenolics some of the activities exerted by resveratrol has been carried out. This review describes the chemistry of yucca saponins and phenolics, summarizes the biological activities of yucca products and constituents and gives an account on the actual and potential applications of yucca products.

Key words

animal nutrition antioxidant activity anti-yeast activity foaming agent furostanol saponins NO production inhibition platelet aggregation inhibition resveratrol spirostanol saponins yuccaols A–E 

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References

  1. Adam, RD 1991The biology of Giardia sppMicrobiol. Rev.55706732PubMedGoogle Scholar
  2. Anthony, NB, Balog, JM, Staudinger, FB, Wall, CV, Walker, RD, Huff, WE 1994Effect of urease inhibitor and ceiling fans on ascites in broilers. 1. Environmental variability and incidence of ascitesPoult. Sci.73801809PubMedGoogle Scholar
  3. Asplund, RO 1991Urease inhibition by extracts and extract fractions from species of the plant genus Yucca J. Anim. Sci.69113Google Scholar
  4. Balog, JM, Anthony, NB, Wall, CV, Walker, RD, Rath, NC, Huff, WE 1994Effect of urease inhibitor and ceiling fans on ascites in broilers. 2. Blood variables, ascites scores and body and organ weightsPoult. Sci.73810816PubMedGoogle Scholar
  5. Blockmans, D, Deckmyn, H, Vermylen, J 1995Platelet activationBlood Rev.9143CrossRefPubMedGoogle Scholar
  6. Buret, A, Gall, DG, Olson, ME 1990Effects of murine giardiasis on growth, intestinal morphology, and disaccharidase activityJ. Parasitol.76403409PubMedGoogle Scholar
  7. Calderon, AA, Zapata, JM, Munoz, R, Pedreno, MA, Ros Barcelo, A 1993Resveratrol production as a part of the hypertensive-like response of grapevine cells to an elicitor from Trichoderma viride New Phytol.124455463Google Scholar
  8. Cheeke, PR 1998Saponins: Surprising benefits of desert plantsThe Linus Pauling Institute NewsletterOregon State UniversityCorvallis, OR45Google Scholar
  9. Cheeke, PR 2000Actual and potential applications of Yucca schidigera and Quillaja saponaria saponins in human and animal nutritionProceedings of the Phytochemical Society of Europe45241254Google Scholar
  10. Cline, JL, Fischer, BA, Trottier, NL, Walker, RD, Easter, RA. 1996Effect of feeding Micro-Aid on stillbirths, preweaning mortality, blood oxygen values of piglets and blood urea nitrogen in sowsJ. Anim. Sci.74189Google Scholar
  11. Colina, JJ, Lewis, AJ, Miller, PS, Fischer, RL 2001Dietary manipulation to reduce aerial ammonia concentrations in nursery pig facilitiesJ. Anim. Sci.7930963103PubMedGoogle Scholar
  12. Czeczot, H, Podsiad, M, Skrzycki, M, Stochmal, A, Oleszek, W 2003Evaluation of the mutagenic activity of phenolics from the bark of Yucca schidigera RoezlActa Polon. Pharm.60357362Google Scholar
  13. Docherty, JJ, Fu, MM, Stiffler, BS, Limperos, RJ, Pokabla, CM, De Lucia, AL 1999Resveratrol inhibition of herpes simplex virus replicationAntiviral Res.43145155CrossRefPubMedGoogle Scholar
  14. Duffy, CF, Killeen, GF, Connolly, CA, Power, RF 2001Effects of dietary supplementation with Yucca schidigera Roezl ex Ortgies and its saponin and non-saponin fractions on rat metabolismJ. Agric. Food Chem.4934083413CrossRefPubMedGoogle Scholar
  15. Farthing, MJG 1994Giardiasis as a diseaseThompson, RCAReynoldson, JALymbery, AJ eds. Giardia: From Molecules to DiseaseUniversity PressCambridge, UK1537Google Scholar
  16. Flaoyen, A, Wilkins, AL, Sandvik, M 2002Ruminal metabolism in sheep of saponins from Yucca schidigera Veter. Res. Commun.26159169Google Scholar
  17. Headon, DR, Buggle, KA, Nelson, AB, Killeen, GF 1991Glycofractions of the Yucca plant and their role in ammonia controlLyons, TP eds. Biotechnology in the Feed IndustryAlltech Technical PublicationsNicholasville, KY95108Google Scholar
  18. Hristov, AN, McAllistar, TA, Van Herk, FH, Cheng, KJ, Newbold, CJ, Cheeke, PR 1999Effect of Yucca schidigera on ruminal fermentation and nutrient digestion in heifersJ. Anim. Sci.7725542563PubMedGoogle Scholar
  19. Hussain, I, Cheeke, PR 1995Effect of dietary Yucca schidigera extract on rumen and blood profiles of steers fed concentrate- or roughage-based dietsAnim. Feed Sci. Technol.51231242CrossRefGoogle Scholar
  20. Hussain, I, Ismail, AM, Cheeke, PR 1996Effects of feeding Yucca schidigera extract in diets varying in crude protein and urea contents on growth performance and cecum and blood urea and ammonia concentrations of rabbitsAnim. Feed Sci. Technol.62121129CrossRefGoogle Scholar
  21. Igile, OG, Oleszek, W, Jurzysta, M, Burda, S, Fafunso, M, Fasanmade, AA 1994Flavonoids from Vernonia amygdalina and their antioxidant activitiesJ. Agric. Food Chem.4224452448CrossRefGoogle Scholar
  22. Jang, M, Udeani, G, Slowing, KV, Thomas, C, Beecher, CWW, Fong, HHS, Farnsworth, NR, Kinghorn, AD, Mehta, RG, Moon, RC, Pezzuto, JM 1997Cancer chemopreventive activity of resveratrol, a natural product derived from grapesScience275218220CrossRefPubMedGoogle Scholar
  23. Jayatilake, GS, Jayasuriya, H, Lee, ES, Koonchanok, NM, Geahlen, RL, Ashendel, CL, McLaughlin, JL, Chang, CJ 1993Kinase inhibitors from Polygonum cuspidatum J. Nat. Prod.5618051810CrossRefPubMedGoogle Scholar
  24. Jeandet, PR, Bessis, M, Sbaghi, M, Meunier, PJ 1995Production of the phytoalexin resveratrol by grapes as a response of grapevine cells to Botrytis attack under natural conditionsPhytopathology143135139Google Scholar
  25. Kaya, S, Erdogan, Z, Erdogan, S 2003Effect of different dietary levels of Yucca schidigera powder on the performance, blood parameters and egg yolk cholesterol of laying quailsJ. Vet. Med. A501417CrossRefGoogle Scholar
  26. Killeen, GF, Buggle, KA, Hynes, MJ, Walsh, GA, Power, RF, Headon, DR 1994Influence of Yucca schidigera preparations on the activity of urease from Bacillus pasteurii J. Sci. Food Agric.65433440Google Scholar
  27. Killeen, GF, Connolly, CR, Walsh, GA, Duffy, CE, Headon, DR, Power, RF 1998aThe effects of dietary supplementation with Yucca schidigera extracts or fractions thereof on nitrogen metabolism and gastrointestinal fermentation processes in the ratJ. Sci. Food Agric.769199CrossRefGoogle Scholar
  28. Killeen, GF, Madigan, CA, Connolly, CR, Walsh, GA, Clark, C, Hynes, MJ, Timmins, BF, James, P, Headon, DR, Power, RF 1998bAntimicrobial saponins of Yucca schidigera and the implications of their in vitro properties for their in vivo impactJ. Agric. Food Chem.4631783186CrossRefGoogle Scholar
  29. Kim, SW, Park, SK, Kang, S, Kang, HC, Oh, HJ, Bae, CY, Bae, DH 2003Hypocholesterolemic property of Yucca schidigera and Quillaia saponaria extracts in human bodyArch. Pharm. Res.2610421046PubMedGoogle Scholar
  30. Kimura, Y, Okuda, H, Kubo, M 1995Effects of stilbenes isolated from medicinal plants on arachidonate metabolism and degranulation in human polymorphonuclear leukocytesJ. Ethnopharmacol.45131139CrossRefPubMedGoogle Scholar
  31. Kroll, MH, Schafer, AJ 1995The analysis of ligand–receptor interaction in platelet activationImmunopharmacology293165Google Scholar
  32. Langcake, P, Price, RJ 1976The production of resveratrol by Vitis vinifera and other members of the Vitaceae as a response to infection and injuryPhysiol. Plant. Pathol.97786CrossRefGoogle Scholar
  33. Levy-Toledano, S 1999Platelet signal transduction pathways: Could we organize them into a hierarchyHaemostasis29415PubMedGoogle Scholar
  34. Mader, TL, Brumm, MC 1987Effect of feeding sarsaponin in cattle and swine dietsJ. Anim. Sci.65915PubMedGoogle Scholar
  35. Makkar, HPS, Sen, S, Blummel, M, Becker, K 1998Effect of fractions containing saponins from Yucca schidigera, Quillaia saponaria, and Acacia auriculoformis on rumen fermentationJ. Agric. Sci.4643244328Google Scholar
  36. Marzocco, S, Piacente, S, Pizza, C, Oleszek, W, Stochmal, A, Pinto, A, Sorrentino, R, Autore, G 2004Inhibition of inducible nitric oxide synthase expression by yuccaol C from Yucca schidigera RoezlLife Sci.7514911501PubMedGoogle Scholar
  37. McAllister, TA, Annett, CB, Cockwill, CL, Olson, ME, Wang, Y 2001Studies on the use of Yucca schidigera to control giardiosisVet. Parasitol.978599PubMedGoogle Scholar
  38. Miyakoshi, M, Tamura, Y, Masuda, H, Mizutani, K, Tanaka, O, Ikeda, T, Ohtani, K, Kasai, R, Yamasaki, K 2000Antiyeast steroidal saponins from Yucca schidigera (Mohave yucca), a new anti-food-deteriorating agentJ. Nat. Prod.63332338CrossRefPubMedGoogle Scholar
  39. Nathan, C 1997Inducible nitric oxide synthase. What difference does it make?J. Clin. Invest.10024172423PubMedCrossRefGoogle Scholar
  40. O’Handley, RM, Cockwill, C, McAllister, TA, Jelinski, M, Morck, DW, Olson, ME 1999Duration of naturally acquired giardiosis and cryptosporidiosis in dairy calves and their association with diarrheaJ. Am. Vet. Med. Assoc.214391396PubMedGoogle Scholar
  41. Olas, B, Wachowicz, B, Saluk-Juszczak, J, Zielinski, T, Kaca, W, Buczynski, A 2001Antioxidant activity of resveratrol in endotoxin-stimulated blood plateletsCell Biol. Toxicol.17117125CrossRefPubMedGoogle Scholar
  42. Olas, B, Wachowicz, B, Stochmal, A, Oleszek, W 2002Anti-platelet effects of different phenolic compounds from Yucca schidigera RoezlBark. Platelets13167173Google Scholar
  43. Olas, B, Wachowicz, B, Stochmal, A, Oleszek, W 2003Inhibition of oxidative stress in blood platelets by different phenolics from Yucca schidigera RoezlBark. Nutr.19633640Google Scholar
  44. Oleszek, W, Sitek, M, Stochmal, A, Piacente, S, Pizza, C, Cheeke, P 2001aSteroidal saponins of Yucca schidigera RoezlJ. Agric. Food Chem.4943924396Google Scholar
  45. Oleszek, W, Sitek, M, Stochmal, A, Piacente, S, Pizza, C, Cheeke, P 2001bResveratrol and other phenolics from the bark of Yucca schidigera RoezlJ. Agric. Food Chem.49747752Google Scholar
  46. Olson, ME, McAllister, TA, Deselliers, L, Morck, DW, Cheng, KJ, Buret, AG, Ceri, H 1995Effects of giardiasis on production in a domestic ruminant (lamb) modelAm. J. Vet. Res.5614701474PubMedGoogle Scholar
  47. Olson, ME, Thorlakson, CL, Deselliers, L, Morck, DW, McAllister, TA 1997 Giardia and Cryptosporidium in Canadian farm animalsVet. Parasitol.68375381PubMedGoogle Scholar
  48. Orsini, F, Pellizzoni, F, Verotta, L, Aburjai, T, Rogers, CB 1997Isolation, synthesis and antiplatelet aggregation activity of resveratrol 3-O-β-d-glucopyranosideJ. Nat. Prod.6010821087CrossRefPubMedGoogle Scholar
  49. Peestok, LA 1979An investigation into the application of Yucca schidigera extracts to biological waste treatmentsMiami UniversityOxford, OHM. Sc.Google Scholar
  50. Pendurthi, UR, Williams, JT, Rao, LV 1999Resveratrol, a polyphenolic compound found in wine, inhibits tissue factor expression in vascular cells: A possible mechanism for the cardiovascular benefits associated with moderate consumption of wineArterioscler. Thromb. Vasc. Biol.19419426PubMedGoogle Scholar
  51. Piacente, S, Bifulco, G, Pizza, C, Stochmal, A, Oleszek, W 2002A novel phenolic spiro derivative, yuccaone A, from Yucca schidigera barkTetrahedron Lett.4391339136CrossRefGoogle Scholar
  52. Piacente, S, Montoro, P, Oleszek, W, Pizza, C 2004 Yucca schidigera bark: Phenolic constituents and antioxidant activityJ. Nat. Prod.67882885CrossRefPubMedGoogle Scholar
  53. Pietta, PG, Simonetti, P, Mauri, PL 1998Antioxidant activity of selected medicinal plantsJ. Agric. Food Chem.4644874490CrossRefGoogle Scholar
  54. Pratt DE (1992) Phenolic compounds in food and their effects on health. In: Huang MT & Lee CY (eds) Symp. Ser. 507, American Chemical Society Books Vol. II (54 p.) Washington, DCGoogle Scholar
  55. Re, R, Pellegrini, N, Proteggente, A, Pannala, A, Yang, M, Rice-Evans, C 1999Antioxidant activity applying an improved ABTS radical cation decolorization assayFree Radic. Biol. Med.2612311237CrossRefPubMedGoogle Scholar
  56. Ruetten, H, Thiemermann, C 1997Prevention of the expression of inducible nitric oxide synthase and the down-regulation of the activation of NF-kB in macrophages by resveratrolBr. J. Pharmacol.126673680Google Scholar
  57. Shen, Z, Haslam, E, Falshaw, CP, Begley, MJ 1986Procyanidins and polyphenols of Larix gmelini barkPhytochemistry2526292635CrossRefGoogle Scholar
  58. Siemann, EH, Creasy, LL 1992Concentration of the phytoalexin resveratrol in wineAm. J. Enol. Vitic.434952Google Scholar
  59. Surh, YJ, Hurh, YJ, Kang, JY, Lee, E, Kong, G, Lee, SJ 1999Resveratrol, an antioxidant present in red wine, induces apoptosis in human promyelocytic leukemia (HL-60) cellsCancer Lett.140110CrossRefPubMedGoogle Scholar
  60. Tanaka, O, Tamura, Y, Masuda, H, Mizutani, K 1996Application of saponins in food and cosmetics: Saponins of Mohave yucca and Sapindus mukurossiWaller, GRYamasaki, K eds. Saponins used in Food and AgriculturalPlenum PressNew York111Google Scholar
  61. Tsai, SH, Lin Shiau, SH, Lin, JK 1999Suppression of nitric oxide synthase and the down-regulation of the activation of Nf-κB in macrophages by resveratrolBr. J. Pharmacol126673680CrossRefPubMedGoogle Scholar
  62. Uenobe, F, Nakamura, S, Miyazawa, M 1997Antimutagenic effect of resveratrol against Trp-P-1Mutat. Res.373197200PubMedGoogle Scholar
  63. Wallace, RJ, Arthaud, L, Newbold, CJ 1994Influence of Yucca schidigera extract on ruminal ammonia concentrations and ruminal microorganismsAppl. Environ. Microbiol.6017621767PubMedGoogle Scholar
  64. Zbikowska, HM, Olas, B, Wachowicz, B, Krajewski, T 1999Response of blood platelets to resveratrolPlatelets10247252PubMedGoogle Scholar

Copyright information

© Springer 2005

Authors and Affiliations

  1. 1.Dipartimento di Scienze FarmaceuticheUniversità degli Studi di SalernoFisciano (Salerno)Italy
  2. 2.Department of BiochemistryInstitute of Soil Science and Plant CultivationPulawyPoland

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