GENDER SPECIFIC VARIATION OF TWO PHENOLIC GLYCOSIDES (POPULIN AND SALICIN) IN POPULUS CILIATA AND IDENTIFICATION OF A NEW COMPOUND (CINNAMOYL-SALICIN)
DOI:
https://doi.org/10.22159/ijpps.2016v8i12.14843Keywords:
Phenolic glycosides, Populus ciliata, salicin, Populin, Cinnamoyl-salicin, TLC, NMR, HPLCAbstract
Objective: To observe gender specific seasonal variation of two phenolic glycosides (PG's) (populin and salicin) in Populus ciliata male and female trees.
Methods: Plant material (bark) was collected from male and female trees throughout the year. The content of salicin and populin was measured using HPLC. Because of the lack of populin in the market, the standard compound was synthesized in the laboratory from salicin following standard procedure. Confirmation and characterization of synthesized populin were done using 1H NMR and 13C NMR. TLC and LC-MS of methanolic extract were performed to observe the presence of populin and salicin in the plant bark.
Results: TLC showed the presence of populin and salicin in crude plant extract at Rf value 0.84 and 0.52, respectively. The results of monthly variation showed a consistent pattern of two PG's for both the sexes. However, salicin content was observed highest compared to populin content. Whereas female trees were observed with low content of PG's compared to male trees. The maximum content of salicin and populin was observed in the flowering season. LC-MS of bark methanolic extract confirmed the presence of a significantly larger peak, which was identified as a cinnamoyl-salicin peak at 463.
Conclusion: The study confirms the highest content of PG's in the flowering season. Additionally, LC-MS study concluded a new compound cinnamoyl-salicin (M+at 463) which is reported first time to the best of author's knowledge. It seems that it could be the denaturation product of 2'-O-cinnamoyl salicortin and can be further explored for biological applications.
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Abreu IN, Ahnlund M, Moritz T, Albrectsen BR. UHPLC-ESI/TOFMS Determination of salicylate-like phenolic glycosides in Populus tremula leaves. J Chem Ecol 2011;37:857-70.
Donaldson JR, Lindroth RL. Genetics, environment and their interaction determine the efficacy of chemical defence in trembling aspen. Ecology 2007;88:729-39.
Rehill B, Clauss A, Wieczorek L, Whitham T, Lindroth R. Foliar phenolic glycosides from Populus fremontii, Populus angustifolia, and their hybrids. Biochem Sys Ecol 2005;33:125-31.
Mahdi JG, Mahdi AJ, Mahdi AJ, Bowen ID. The historical analysis of aspirin its relation to the willow tree and antiproliferative and anticancer potential. Cell Proliferation 2006;39:147-55.
Julkunen-Tiitto R. Phenolic constituents of Salix: a chemotaxonomic survey of further finnish species. Phytochemicals 1989;28:2115-25.
Erwin EA, Turner MG, Lindroth RL, Romme WH. Secondary plant compounds in seedling and mature aspen (Populus tremuloides) in Yellowstone National Park, Wyoming. Am Midl Nat 2001;145:299-308.
Harding SA, Jiang H, Jeong ML, Casado FL, Lin HW, Tsai CJ. Functional genomics analysis of foliar condensed tannin and phenolic glycoside regulation in natural cottonwood hybrids. Tree Physol 2005;25:1475-86.
Osier TL, Lindroth RL. Genotype and environment determine allocation to and costs of resistance in quaking aspen. Oecologica 2006;148:293-303.
Price PW, Waring GL, Julkunen-Tiitto R, Tahvanainen J, Mooney HA, Craig TP. The carbon nutrient balance hypothesis in a within-species phytochemical variation of Salix lasiolepis. J Chem Ecol 1989;15:1117-31.
Boecklen WJ, Price PW, Mopper S. Sex and drugs and herbivores: sex-based herbivory in arroyo willow (Salix lasiolepis). Ecology 1990;71:581-8.
Nichols-Oriens CM, Fritz RS, Clausen TP. The genetic basis for variation in the concentration of phenolic glycosides in Salix sericea: clonal variation and sex-based differences. Biochem Syst Ecol 1993;21:535-42.
Lindroth RL. Biochemical ecology of aspen-Lepidoptera interactions. J Kans Entomol Soc 1992;66:372-80.
Tuskan GA, DiFazio S, Faivre-Rampant P, Gaudet M, Harfouche A, Jorge V, et al. The obscure events contributing to the evolution of an incipient sex chromosome in Populus: a retrospective working hypothesis. Tree Genet Genomes 2012;8:559-71.
Greenaway W, Whatley FR. Analysis of phenolics of bud exudate of Populus ciliata by GC-MS. Phytochem 1991;30:1887-9.
Mattson WJ, Scriber JM. Nutritional ecology of insect folivores of woody plants: nitrogen, water, fiber, and mineral considerations. In: Slansky F, Rodriguez JG. Ed. Nutritional ecology of insects, mites, spiders, and related invertebrates. John Wiley and Sons, Inc., New York; 1987. p. 105-46.
Alliende MC. Demographic studies of a dioecious tree. II. The distribution of leaf predation within and between trees. J Ecol 1989;77:1048-58.
Jing SW, Coley PD. Dioecy and herbivory: the effect of growth rate on plant defence in Acer negundo. Oikos 1990;58:369-77.
Richtmyer NK, Yeakel EH. The structure of populin. J Am Chem Soc 1935;56:2495-7.
Verma SC, Hazea K, Devgan M, Ramaiah M, Sarkar BK. Phytochemical and high-performance liquid chromatography analysis of Portulaca quadrifida Linn. Assian J Pharm Clin Res 2016;9:163-4.
Selvaraj S, Chittibabu CV, Janarthanam B. Studies on pjytochemical screening, antioxidant activity and extraction of active compound (swertiamarin) from leaf extract of Enicostemma littorale. Assian J Pharm Clin Res 2014;7:240-4.
Gholkar M, Laddha KS. Seasonal variation in the content of mangiferin in leaves of Mangifera indica L. Int J Pharm Pharm Sci 2015;7:578-80.
Sowparthani K. Phytochemical analysis, high-performance liquid chromatography, and antibacterial activity of endophytic fungi Pestalotiopsis sp. isolated from Acalypha idica (Linn). Asian J Pharm Clin Res 2016;9:101-3.
Forster N, Ulrichs C, Zander M, Katzel E, Mewis I. Influence of the season on the salicylate and phenolic glycoside content of Salix daphnoides, Salix pentandra and Salix purpurea. J Appl Bot Food Qual 2008;82:99-102.
Thieme H. Die Phenolgykoside der Salicaceen 5. Mitteilung: unter-suchungenuber die gykosidspektren und den glykosidgehalt der mittel-deutschen Salixarten. Pharmazie 1965;20:570-4.
Meier B, Sticher O, Bettscart A. Weidenrinden-qualitat. Gesamtsalicinbestimmung in weidenrinden und weiden-praparatenmit HPLC. Deutsche Apotheker Zeitung 1985;125:341-7.
Lovette-Doust L, Lovette-Doust L. Leaf demography and clonal growth in female and male Rumex acetosella. Ecology 1987;68:2056-8.
Elmqvist T, Gates RG, Harper JK, Gardifell H. Flowering in males and females of a Utah willow, Salix rigida, and effects on growth, tannins, phenolic glycosides and sugars. Oikos 1991;61:65-72.
Pearl IA, Darling SF, Justman O. Studies on the leaves of the family Salicaceae. L. Populin from the leaves of Populus grandidentata and Populus tremuloides. J Organic Chem 1962;27:2685-7.
Kleiner KW, Raffa KF, Dickson RE. Partitioning of 14C-labeled photosynthate to allelochemicals and primary metabolites in source and sink leaves of aspen: evidence for secondary metabolite turnover. Oecologica 1999;119:408-18.
Ruuhola TM, Julkunen-Tiitto MRK. Salicylates of intact Salix myrsinifolia plantlets do not undergo rapid metabolic turnover. Plant Physiol 2000;122:895-905.
Ruuhola TM, Julkunen-Tiitto MRK, Vainiotalo P. In vitro degradation of willow salicylates. J Chem Ecol 2003;29:1083-97.
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