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Rhus hirta (L.) Sudw. – Phytochemical characteristics of the most widely cultivated representative of the Anacardiaceae in the Czech Republic


Authors: Petr Babula 1;  Anna Korvasová 1;  Vojtech Adam 1;  René Kizek 1
Authors‘ workplace: Veterinární a farmaceutická univerzita Brno, Farmaceutická fakulta, Ústav přírodních léčiv 1
Published in: Čes. slov. Farm., 2011; 60, 229-236
Category: Review Articles

Overview

The family Anacardiaceae Lindl. (cashew family, sumac family) is one of the nine families of the order Sapindales Dumortier. It consists of about 600 species classified in 70 genera. Members of the family are shrubs, trees and lianas with pantropical distribution; however, a few species occur in the North Temperate Zone. Some species are used for the production of fruit (mango, mombin), some species are cultivated for edible seeds (pistachio, cashew nuts). Many species are of toxicological importance, especially members of the genus Toxicodendron P. Mill., other species are widely used in folk medicines. This review introduces the most widely cultivated species of the Anacardiaceae family in the Czech Republic and concurrently invasive plant Staghorn Sumac – Rhus hirta (L.) Sudw. The secondary metabolites, their pharmacological properties and pharmaceutical importance of the species are discussed.

Key words:
Rhus hirtaAnacardiaceae – gallotanins – essential oil – folk medicine


Sources

1. Judd, W. S., Campbell, C. S., Kellogg, E. A., Stevens, P. F., Donoghue, M. J.: Plant systematics – a phylogenetic approach. 2nd ed. Sunderland: Sinauer Associates, Inc. 2002; 576 s.

2. Kubát, R., Hrouda, L., Chrtek, J., Kaplan, Z., Kirschner, J., Stěpánek, J.: Klíč ke květeně České republiky. 1. vyd. Praha: Academia 2002; 928 s.

3. Bachelier, J. B., Endress, P. K.: Comparative floral morphology and anatomy of Anacardiaceae and Burseraceae (Sapindales), with a special focus on gynoecium structure and evolution. Bot. J. Linnean Soc. 2009; 159, 499–571.

4. Greco, C. F., Holland, D., Kevan, P. G.: Foraging behaviour of honey bees (Apis mellifera L) on staghorn sumac (Rhus hirta Sudworth (ex-typhina L.)): Differences and dioecy. Can. Entomol. 1996; 128, 355–366.

5. Gallant, J. B., Kemp, J. R., Lacroix, C. R.: Floral development of dioecious staghorn sumac, Rhus hirta (Anacardiaceae). Int. J. Plant Sci. 1998; 159, 539–549.

6. Reveal, J. L.: Rhus-Hirta (L) Sudworth, a newly revived correct name for Rhus-Typhina L. (Anacardiaceae). Taxon 1991; 40, 489–492.

7. Grandtner, M. M.: Elsevier’s dictionary of trees. 1st ed. Radarweg: Elsevier:, B.V. 2005; 1493 s.

8. Pilát, A.: Listnaté stromy a keře našich zahrad a parků. 1. vyd. Praha: Statní zemědělské nakladatelství 1953; 1100 s.

9. Mollerova, J.: Notes on invasive and expansive trees and shrubs. J. For. Sci. 2005; 51, 19–23.

10. Werner, P. A., Harbeck, A. L.: The pattern of tree seedling establishment relative to staghorn sumac cover in Michigan old fields (Rhus typhina). Am. Midl. Nat. 1982; 108, 124–132.

11. Doust, J. L., Doust, L. L.: Modules of production and reproduction in a dioecious clonal shrub, Rhus-Typhina. Ecology 1988; 69, 741–750.

12. Meilleur, A., Veronneau, H., Bouchard, A.: Shrub communities as inhibitors of plant succession in southern Quebec. Environ. Manage. 1994; 18, 907–921.

13. Fan, P., Marston, A.: How can phytochemists benefit from invasive plants? Nat. Prod. Commun. 2009; 4, 1407–1416.

14. Luken, J. O.: Gradual and episodic changes in the structure of Rhus–Typhina clones. Bull. Torrey Bot. Club. 1990; 117, 221–225.

15. Peterson, C. J., Facelli, J. M.: Contrasting germination and seedling growth of Betula-Alleghaniensis and Rhus–Typhina subjected to various amounts and types of plant litter. Am. J. Bot. 1992; 79, 1209–1216.

16. Wang, G. M., Jiang, G. M., Yu, S. L., Li, Y. H., Liu, H.: Invasion possibility and potential effects of Rhus typhina on beijing municipality. J. Integr. Plant Biol. 2008; 50, 522–530.

17. Del Tredici, P.: Spontaneous urban vegetation: reflections of change in a globalized world. Nat. Cult. 2010; 5, 299–315.

18. Zhang, C. H., Zheng, Y. Q., Li, J. L., Yan, H. P., Wang, L.: Dispersal of staghorn sumac in Beijing areas. Acta Ecol. Sin. 2005; 25, 978–985.

19. Li, X. J., Baskin, J. M., Baskin, C. C.: Seed morphology and physical dormancy of several North American Rhus species (Anacardiaceae). Seed Sci. Res. 1999; 9, 247–258.

20. Li, X. J., Baskin, J. M., Baskin, C. C.: Physiological dormancy and germination requirements of seeds of several North American Rhus species (Anacardiaceae). Seed Sci. Res. 1999; 9, 237–245.

21. Marks, P. L.: Apparent fire-stimulated germination of Rhus-typhina seeds. Bull. Torrey Bot. Club. 1979; 106, 41–42.

22. Lafleur, P. M., Farnsworth, A. G.: Light interception and canopy radiation balance of staghorn sumac (Rhus typhina). Can. J. For. Res.-Rev. Can. Rech. For. 2008; 38, 1695–1700.

23. Zhang, Z. J., Jiang, C. D., Zhang, J. Z., Zhang, H. J., Shi, L.: Ecophysiological evaluation of the potential invasiveness of Rhus typhina in its non-native habitats. Tree Physiol. 2009; 29, 1307–1316.

24. Sun, T. X., Lu, F. D., Zheng, Y. Q., Zhang, C. H., Li, B. J., Wang, L., Yang, X. Y.: Allelopathic activity of exotic tree Rhus typhina. For. Res. 2010; 23, 195–201.

25. Jaquish, L. L., Ewers, F. W.: Seasonal conductivity and embolism in the roots and stems of two clonal ring-porous trees, Sassafras albidum (Lauraceae) and Rhus typhina (Anacardiaceae). Am. J. Bot. 2001; 88, 206–212.

26. Nelson, W. R.: Planting design: a manual of theory and practice. 2nd ed. Champaign: Stipes Publishing, Llc. 1979; 271 s.

27. Denzel, K., Gross, G. G.: Biosynthesis of gallotannins – enzymatic disproportionation of 1,6-digalloylglucose to 1,2,6-trigalloylglucose and 6-galloylglucose by an acyltransferase from leaves of Rhus-typhina L. Planta. 1991; 184, 285–289.

28. Gross, G. G., Denzel, K.: Biosynthesis of gallotannins – beta-glucogallin-dependent galloylation of 1,6-digalloylglucose to 1,2,6-trigalloylglucose. Zeitschrift fur Naturforschung C. J. Biosci. 1991; 46, 389–394.

29. Werner, I., Bacher, A., Eisenreich, W.: Retrobiosynthetic NMR studies with C-13-labeled glucose – Formation of gallic acid in plants and fungi. J. Biol. Chem. 1997; 272, 25474–25482.

30. Guzik, U., Wojcieszynska, D., Jaroszek, P.: Biosynthesis of gallic acid and its application. Biotechnologia 2010; 1, 119–131.

31. Werner, R. A., Rossmann, A., Schwarz, C., Bacher, A., Schmidt, H. L., Eisenreich, W.: Biosynthesis of gallic acid in Rhus typhina: discrimination between alternative pathways from natural oxygen isotope abundance. Phytochemistry. 2004; 65, 2809–2813.

32. Grundhofer, P., Niemetz, R., Schilling, G., Gross, G. G.: Biosynthesis and subcellular distribution of hydrolyzable tannins. Phytochemistry 2001; 57, 915–927.

33. Denzel, K., Schilling, G., Gross, G. G.: Biosynthesis of gallotannins. Enzymatic conversion of 1,6-digalloylglucose to 1,2,6-trigalloylglucose. Planta 1988; 176, 135–137.

34. Grundhofer, P., Gross, G. G.: Purification of tetragalloylglucose 4-O-galloyltransferase and preparation of antibodies against this key enzyme in the biosynthesis of hydrolyzable tannins. Z. Naturforsch. (C). Biosci. 2000; 55, 582–587.

35. Hagenah, S., Gross, G. G.: Biosynthesis of 1,2,3,6-tetra-o-galloyl-beta-d-glucose. Phytochemistry 1993; 32, 637–641.

36. Rausch, H., Gross, G. G.: Preparation of [C-14]-labelled 1,2,3,4,6-penta-O-galloyl-beta-D-glucose and related gallotannins. Z. Naturforsch. (C). 1996; 51, 473–476.

37. Niemetz, R., Gross, G. G.: Enzymology of gallotannin and ellagitannin biosynthesis. Phytochemistry. 2005; 66, 2001–2011.

38. Niemetz, R., Gross, G. G.: Gallotannin biosynthesis: beta-glucogallin: hexagalloyl 3-O-galloyltransferase from Rhus typhina leaves. Phytochemistry. 2001; 58, 657–661.

39. Niemetz, R., Gross, G. G.: Gallotannin biosynthesis: Purification of beta-glucogallin: 1,2,3,4,6-pentagalloyl-beta-D-glucose galloyltransferase from sumac leaves. Phytochemistry 1998; 49, 327–332.

40. Niemetz, R., Gross, G. G.: Gallotannin biosynthesis: A new beta-glucogallin-dependent galloyltransferase from sumac leaves acylating gallotannins at positions 2 and 4. J. Plant Physiol. 1999; 155, 441–446.

41. Frohlich, B., Niemetz, R., Gross, G. G.: Gallotannin biosynthesis: two new galloyltransferases from Rhus typhina leaves preferentially acylating hexa- and heptagalloylglucoses. Planta 2002; 216, 168–172.

42. Grundhofer, P., Gross, G. G.: Immunocytochemical studies on the origin and deposition sites of hydrolyzable tannins. Plant Sci. 2001; 160, 987–995.

43. Cornthwaite, D., Haslam, E.: Gallotannins 9. Biosynthesis of Gallic Acid in Rhus Typhina. J. Chem. Soc. 1965; 89, 3008–3011.

44. Schilling, N., Ferguson, J. A., Kandler, O.: Rapidly Synthesized Tannin in Leaves of Rhus-Typhina. Phytochemistry. 1972; 11, 873.

45. Islambekov, S. Y., Mavlyanov, S. M., Kamaev, F. G., Ismailov, A. I.: Phenolic compounds of sumac. Chem. Nat. Compounds. 1994; 30, 37–39.

46. Poma, K.: Production of tannins in suspension-cultures of Rhus-Typhina L. Acta Bot. Neerl. 1987; 36, 309–309.

47. Schmidt, J., Porzel, A., Adam, G.: 3 alpha,20-dihydroxy-3 beta,25-epoxylupane, a triterpene from Rhus typhina. Phytochemistry 1998; 49, 2049–2051.

48. Connolly, J. D., Hill, R. A.: Triterpenoids. Nat. Prod. Rep. 2001; 18, 131–147.

49. Kossah, R., Nsabimana, C., Zhang, H., Chen, W.: Optimization of extraction of polyphenols from syrian sumac (Rhus Coriaria L.) and chinese sumac (Rhus Typhina L.) fruits. Res. J. Phytochem. 2010; 4, 146–153.

50. Buziashvili, I. S., Komissarenko, N. F., Kolesnikov, D, G.: Phenolic Compounds of Rhus typhina and R. aromatica. Khimiya Prir. Soedin. 1973, 555–556.

51. Correia, S. D. J., David, J. P., David, J. M.: Secondary metabolites from species of Anacardiaceae. Quim. Nova. 2006; 29, 1287–1300.

52. Buziashvili, I. S., Komissarenko, N. F., Kolesnikov, D. G.: Phenolic compounds of Rhus typhina and R. aromatica. Chem. Nat. Compounds. 1975; 9, 524.

53. Pislarasu, N., Mircea, C.: Contributions to the pharmacognostic study of Rhus typhina L. flowers and fruit (Rumanian). Farmacia 1975; 23, 183–190.

54. Carr, M. E., Roth, W. B., Bagby, M. O.: Potential resource materials from Ohio plants. Econ. Bot. 1986; 40, 434–441.

55. Udagama-Randeniya, P., Savidge, R.: Electrophoretic analysis of coniferyl alcohol oxidase and related laccases. Electrophoresis 1994; 15, 1072–1077.

56. Bestmann, H.-J., Classen, B., Kobold, U., Vostrowsky, O., Klingauf, F., Stein, U.: Steam volatile constituents from leaves of Rhus typhina. Phytochemistry 1988; 27, 85–90.

57. Tischer, J.: On some ingredients of the fruits of staghorn sumac (Rhus typhina L.). Die Pharmazie 1960; 15, 83–89.

58. Kossah, R., Nsabimana, C., Zhao, J., Chen, H., Tian, F., Zhang, H., Chen, W.: Comparative study on the chemical composition of Syrian sumac (Rhus coriaria L.) and Chinese sumac (Rhus typhina L.) fruits. Pak. J. Nutr. 2009; 8, 1570–1574.

59. Rayne, S., Mazza, G.: Biological activities of extracts of sumac (Rhus spp.): a review. Plant Foods Hum. Nutr. 2007; 62, 165–175.

60. Chaiyasut, C., Kusirisin, W., Lailerd, N., Larttrakarnnon, L., Suttajit, M., Srichairatanakool, S.: Effect of Phenolic Compounds of Thai Indigenous Plants on Oxidative stress in Streptozocin-Induced Diabetic Rats. Evid. Compl. Alt. Med. 2011; in press.

61. Ippen, H.: Contact allergy to anacardiaceae. A review and case studies of poison ivy allergy in Central Europe. Derm. Ber. Umw. 1983; 31, 140–148.

62. Borchardt, J. R., Wyse, D. L., Sheaffer, C. C., Kauppi, K. L., Fulcher, R. G., Ehlke, N. J., Biesboer, D. D., Bey, R. F.: Antioxidant and antimicrobial activity of seed from plants of the Mississippi river basin. J. Med. Plants Res. 2009; 3, 707–718.

63. McCune, L. M., Johns, T.: Antioxidant activity in medicinal plants associated with the symptoms of diabetes mellitus used by the Indigenous Peoples of the North American boreal forest. J. Ethnopharmacol. 2002; 82, 197–205.

64. Jedinak, A., Valachova, M., Maliar, T., Sturdik, E.: Antiprotease activity of selected Slovak medicinal plants. Pharmazie. 2010; 65, 137–140.

65. Kossah, R., Zhang, H., Chen, W.: Antimicrobial and antioxidant activities of Chinese sumac (Rhus typhina L.) fruit extract. Food Control. 2011; 22, 128–132.

66. Song, M. Y., Jeong, G. S., Kwon, K. B., Ka, S. O., Jang, H. Y., Park, J. W., Kim, Y. C., Park, B. H.: Sulfuretin protects against cytokine-induced beta-cell damage and prevents streptozotocin-induced diabetes. Exp. Mol. Med. 2010; 42, 628–638.

67. Lee, J. C., Kim, J., Lim, K. T., Yang, M. S., Jang, Y. S.: Ethanol fluted extract of Rhus verniciflua Stokes showed both antioxidant and cytotoxic effects on mouse thymocytes depending on the dose and time of the treatment. J. Biochem. Mol. Biol. 2001; 34, 250–258.

68. Kim, J. H., Jung, C. H., Jang, B. H., Go, H. Y., Park, J. H., Choi, Y. K., Il Hong, S., Shin, Y. C., Ko, S. G.: Selective cytotoxic effects on human cancer cell lines of phenolic-rich ethyl-acetate fraction from Rhus verniciflua Stokes. Am. J. Chin. Med. 2009; 37, 609–620.

69. Li, Y., Kim, J., Li, J., Liu, X., Himmeldrik, K., Ren, Y., Wagner, T. E., Chen, X.: Natural anti-diabetic compound 1,2,3,4,6-penta-O-galloyl-D-glucopyranose binds to insulin receptor and activates insulin-mediated glucose transport signaling pathway. Biochem. Biophys. Res. Commun. 2005; 336, 430–437.

70. Jayanegara, A., Togtokhbayar, N., Makkar, H. P. S., Becker, K.: Tannins determined by various methods as predictors of methane production reduction potential of plants by an in vitro rumen fermentation system. Anim. Feed Sci. Technol. 2009; 150, 230–237.

71. Muetzel, S., Becker, K.: Extractability and biological activity of tannins from various tree leaves determined by chemical and biological assays as affected by drying procedure. Anim. Feed Sci. Technol. 2006; 125, 139–149.

72. Takemoto, J. K., Davies, N. M.: Method development for beta-glucogallin and gallic acid analysis: Application to urinary pharmacokinetic studies. J. Pharm. Biomed. Anal. 2011; 54, 812–816.

73. Erichsen-Brown, C.: Medicinal and other uses of North American plants: a historical survey with special reference to the Eastern Indian tribes. 1st ed. Toronto: Breezy Creeks Press 1989; 512 s.

74. Harper-Lore, B., Wilson, M.: Roadside use of native plants. 1st ed. Washington, D. C.: Island Press 1999; 665 s.

75. Moerman, D. E.: Native American Ethnobotany, 5th ed. Portland: Timber Press., Inc., USA 2004; 933 s.

76. McCune, L. M., Johns, T.: Antioxidant activity relates to plant part, life form and growing condition in some diabetes remedies. J. Ethnopharmacol. 2007; 112, 461–469.

77. Ligor, M., Buszewski, B.: Application of TLC and OPLC in the determination of pigments from natural products. J Planar Chromatogr. – Modern TLC. 2001; 14, 334–337.

78. Moerman, D. E.: Native American Food Plants: An Ethnobotanical Dictionary. 1st ed. Portland: Timber Press, Inc. 2010; 455 s.

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