PHENOLIC CONTENT IN THE NEEDLES OF CRYPTOMERIA JAPONICA (THUNB. EX L. F.) D. DON, CUPRESSOCYPARIS × LEYLANDII (A.B. JACKS. & DALLIM.) DALLIM. “CASTLEWELLAN GOLD“ AND SEQUOIADENDRON GIGANTEUM (LINDL.) J. BUCHHOLZ
DOI:
https://doi.org/10.54652/rsf.2014.v44.i2.100Keywords:
Cupressaceae, giant sequoia, gymnosperm, Leyland cypress, phenolic compounds, spectrophotometry, sugiAbstract
UDK: 581.19:547.56:582.477
Various phenolic compounds can be found in a gymnosperms and have been related to their bioactive properties, esspecially as a allelochemicals. Total phenol, flavonoid (flavone and flavonol) and protoanthocyanindin content was estimated quantitatively by using spectrophotometric method in the needle methanol extracts of mature Cryptomeria japonica, Cupressocyparis × leylandii „Castewellan Gold“ and Sequoiadendron giganteum individuals. Although there is a strong intraspecific variability on the basis of the studied group of compounds, Duncan's test showed that C. japonica is clearly distinguishable from the other two taxa analyzed, and in particular on the basis of total proanthocyanidins and phenolics content. On the other hand, S. giganteum and C. × leylandii only differ on the basis of the flavonoid content calculated in terms of quercetin equivalent. In all three taxa proanthocyanidins had the highest variability. The ratios and relatively high content of analyzed phenolic compounds for all three studied taxa indicate that they may be considerd as a potential both chemotaxonomic characters and valuable sources of antioxidants, which should be confirmed by further researchs.
References
ALONSO, M., ROZADOS, M. J., VEGA, J. A., PÉREZ-GOROSTIAGA, P., CUIÑAS P., FONTÚRBEL, M. T., FERNÁNDEZ, C. (2002): Biochemical responses of Pinus pinaster trees to fire-induced trunk girdling and crown scorch: Secondary metabolites and pigments as needle chemical indicators. Journal of Chemical Ecology 28(4): 687-700.
APPLETON, R. A., MCCRINDLE, R., OVERTON, K. H. (1970): The diterpenes from the leaves of Cryptomeria japonica. Phytochemistry 9: 581-583.
BAGAL, U. R., LEEBENS-MACK, J. H., LORENZ, W. W., DEAN, J. F. D. (2012): The phenylalanine ammonia lyase (PAL) gene family shows a gymnosperm-specific lineage. Genomics 13 (Suppl 3): S1: http://www.biomedcentral.com/1471-2164/13/S3/S1.
BÄRLOCHER, F., GRAÇA, M. A. S. (2005): Total phenolics. In: Graça M. A. S., Bärlocher F., Gessner M. O. (eds.). Methods to Study Litter Decomposition: A Practical Guide, Springer, The Netherlands. pp. 97-100.
BONNER, F. T., KARRFALT, R. P. (EDS). (2008): The Woody Plant Seed Manual, USDA Forest Service’s Agriculture Handbook United States 727.
CARNACHAN, S. M., HARRIS, P. J. (2000): Ferulic acid is bound to the primary cell walls of all gymnosperm families. Biochemical Systematics and Ecology 28: 865-879.
CASTILLO, F., HERNÁNDEZ, D., GALLEGOS, G., RODRÍGUEZ, R., AGUILAR, C. N. (2012): Antifungal properties of bioactive compounds from plants. In: Dhanasekaran, D., Thajuddin, N., Panneerselvam, A. (eds). Fungicides for plant and animal diseases. Croatia, Europe: InTech.
CASTRO, M. A., GORDALIZA, M., DEL CORRAL, J. M. M., SAN FELICIANO, A. (1996): The distribution of lignanoids in the order Coniferae. Phytochemistry 41(4): 995-1011.
CHANG, C., YANG, M., WEN, H., CHEM. J. (2002): Estimation of total flavonoid content in propolis by two complementary colorimetric methods. Journal of Food and Drug Analysis 10: 178-182.
CHENG, S. S., CHANG, S. T. (2014): Bioactivity and characterization of exudates from Cryptomeria japonica bark. Wood Science and Technology 48: 831–840.
CROZIER, A., JAGANATH, I. B., CLIFFORD, M. N. (2006): Phenols, polyphenols and tannins: An overview. In: Crozier A., Clifford M.N., Ashihara H. (eds), Plant Secondary Metabolites: Occurrence, Structure and Role in the Human Diet, Blackwell Publishing Ltd, Oxford, UK.
EARLE, J. C. (2013): The Gymnosperm Database: http://www.conifers.org/cu/, 10.09.2014.
GIERTYCH, M. J., KAROLEWSKI, P., DE TEMMERMAN, L. O. (1999): Foliage age and pollution alter content of phenolic compounds and chemical elements in Pinus nigra needles. Water, Air, and Soil Pollution 110: 363-377.
GURAV, K. D., PATIL, D. T., THITE, S. V., PATIL, P. R., KORE, B. A. APARADH V. T. (2013): Preliminary investigation of various secondary metabolites from some gymnosperm species. International Journal of Pharmaceutical and Chemical Sciences 2(2): 841-843.
GUT, B. (2008): Trees in Patagonia. Birkhäuser Verlag AG, Basel, pp. 99.
HANSON, J. R. (2007): Chemistry in the garden. The Royal Society of Chemistry, Cambridge, UK, pp. 76.
HATCHER, P. E. (1990): Seasonal and age-related variation in the needle quality of five conifer species. Oecologia 85: 200-212.
HENLEY-SMITH, P., WHITING, D. A. (1976): New norlignans of Sequoiadendron gigantea; Phytochemical comparison with Sequoia sempervirens. Phytochemistry 15: 1285-1287.
HUTZLER, P., FISCHBACH, R., HELLER, W., JUNGBLUT, T. P., REUBER, S., SCHMITZ, R., VEIT, M., WEISSENBÖCK, G., SCHNITZLER, J. P. (1998): Tissue localization of phenolic compounds in plants by confocal laser scanning microscopy. Journal of Experimental Botany 49(323): 953-965.
IBATA, K., KAGEYU, A., TAKIGAWA, T., OKADA, M., NISHIDA, T., MIZUNO, M., TANAKA, Y. (1984): Polyprenols from conifers: multiplicity in chain length distribution. Phytochemistry 23(11): 2517-2521.
IVANESCU, L., GOSTIN, I. N. (2008): Accumulation of phenolic compunds in the needles of Picea abies Karst. and Pinus sylvestris L.: Biological markers of air pollution damage. Natura Montenegrina 7(2): 583-591.
JANJIĆ, N. (1966): Prilog poznavanju nesamonikle dendroflore Sarajeva i okoline, ANU BiH. Radovi-XXIX, Odjelj. privr.-tehn. nauka, knj.9, Sarajevo.
JANJIĆ, N. (2002): Šesti prilog poznavanju nesamonikle dendroflore Sarajeva i okoline. Radovi Šum.fak.Sarajevo, 1.
JOSHI, S., SATI, S. C. (2012): Antifungal potential of gymnosperms: A review. In: Sati S. C., Belwal M. (eds.), Microbes: Diversity and Biotechnology, pp. 333-345.
KAZUMASA, Y., NISHIGUCHI, M., FUTAMURA, N., NANJO, T. (2007): Expressed sequence tags from Cryptomeria japonica sapwood during the drying process. Tree Physiology 27: 1-9.
KOFUJITA, H., OTA, M., TAKAHASHI, K., KAWAI, Y., HAYASHI, Y. (2002): A diterpene quinone from the bark of Cryptomeria japonica. Phytochemistry 61: 895–898.
LATTANZIO, V., LATTANZIO, V. M. T., CARDINALLI, A. (2006): Role of phenolics in the resistance mechanisms of plants against fungal pathogens and insects. Phytochemistry, Advances in Research: 23-67, ISBN: 81-308-0034-9.
LEBRETON, P. (1990): Chemotaxonomy of the Gymnospermae. Bulletin de la Société Botanique de France, Lettres Botaniques 137 (1): 35-46.
LEVINSON, A. S., LEMOINE, G., SMART, E. C. (1971): Volatile oil from foliage of Sequoiadendron giganteum: change in composition during growth. Phytochemistry: 971(10): 1087-1094.
MĂRGHITAŞ, L. AL., DEZMIREAN, D., LASLO, L., MOISE, A., POPESCU, O., MAGHEAR, O. (2007): Validated method for estimation of total flavonoids in Romanian propolis. Bulletin of University of Agricultural Sciences and Veterinary Medicine Cluj-Napoca. Animal Science and Biotechnologies 63-64: http://journals.usamvcluj.ro/index.php/zootehnie/article/view/2220.
MIGUEL, M. G. (2010): Antioxidant and anti-inflammatory activities of essential oils: A short review. Molecules 15: 9252-9287.
NAGAHAMA, S., TAZAKI, M., KOBAYASHI, H., SUMIMOTO, M. (1993): Sesquiterpene alcohols from Cryptomeria japonica and C. fortunei leaf oil. Phytochemistry 33(4): 879-882.
ORDOÑEZ, A., GOMEZ, J., VATTUONE, M., ISLA, M. (2006): Antioxidant activities of Sechium edule (Jacq.) Swart extracts. Food Chemistry 97: 452-458.
PERRY, N. B., WEAVERS, R. T. (1985): Infraspecific variation of foliage diterpenes of Dacrydium cupressinum. Phytochemistry 24(10): 2233-2237.
RIFFER, R., ANDERSON, A. B. (1967): Chemistry of the genus Sequoia-IV. The structures of the C17 phenols from Sequoia sempervirens. Phytochemistry 6: 1557-1562.
ROMANI, A., GALARDI, C., PINELLI, P. MULINACCI, N., HEIMLER, D. (2002): HPLC quantification of flavonoides and biflavonoides in Cupressaceae leaves. Chromatographia 56 (7/8): 469-474.
SCHEFFER, J. J. C., RUYS-CATLENDER, C. M., KOEDAM, A., SVENDSEN, A. B. (1980): A comparative study of X Cupressocyparis leylandii clones (Cupressaceae) by gas chromatographic analysis of their leaf oils. Botanical Journal of the Linnean Society 81(3): 215-224.
SHYUR, L. F., HUANG, C. C., LO, C. P., CHIU, C. Y., CHEN, Y. P., WANG S. Y., CHANG S. T. (2008): Hepatoprotective phytocompounds from Cryptomeria japonica are potent modulators of inflammatory mediators. Phytochemistry 69(6): 1348-1358.
SINGH, H. P., KOHLI, R. K., BATISH D. R., KAUSHAL, P. S. (1999): Allelopathy of gymnospermous trees. Journal of Forestry Research 4: 245-254.
SU, W. C., FANG, J. M., CHENG Y. S. (1993): Hexacarbocyclic triterpenes from leaves of Cryptomeria japonica. Phytochemistry 34(3): 119-782.
SU, W. C., FANG, J. M., CHENG, Y. S. (1995a): Sesquiterpenes from leaves of Cryptomeria japonica. Phytochemistry 39(3): 603-607.
SU, W. C., FANG, J. M., CHENG, Y. S. (1995b): Flavonoids and lignans from leaves of Cryptomeria japonica. Phytochemistry 40(2): 563-566.
SUN, B., DA-SILVA, J. M. R., SPRANGER, I. (1998): Critical factors of vanillin assay for catechins andproanthocyanidins. Journal of Agriculture and Food Chemistry 46: 4267-4274.
VERMERRIS, W., NICHOLSON, R. (2008): Phenolic compound biochemistry. Springer Science+Business Media B.V.
VIDAKOVIĆ, M., FRANJIĆ, J. (2004). Golosjemenjače. Zagreb. Šumarski fakultet Sveučilišta u Zagrebu.
WETTESTEIN, D. VON, JENDE-STRID, B., AHRENST-LARSEN, B., SØRENSEN, J. A. (1977): Biochemical mutant in barley renders chemical stabilization of beer superfluous. Carlsberg Research Communications 42(5): 341-351.
WINK, M. (1999): Biochemistry of plant secondary metabolism. Annual Plant Reviews 2: 358.
WINK, M. (2012): Medicinal plants: a source of anti-parasitic secondary metabolites. Molecules 17: 12771-12791.
WOLFE, K., WU, X., LIU, R. (2003): Antioxidant activity of apple peels. Journal of Agricultural and Food Chemistry 51: 609-614.
YANG, Z.-Y., RAN, J.-H., WANG, X.-Q. (2012): Three genome-based phylogeny of Cupressaceae s.l.: Further evidence for the evolution of gymnosperms and Southern Hemisphere biogeography. Molecular Phylogenetics and Evolution 64: 452-470.
YOSHIDA, K., HIRAIDE, M., NISHIGUCHI, M., HISHIYAMA, S., KATO, A. (2004): A heartwood norlignan, agatharesinol, was generated in sapwood during withering of a sugi (Cryptomeria japonica D. Don) Log. Bulletin of Forestry and Forest Products Research Institute 3(1): 25-28.
