Examination of Natural Products Chemistry (Lecturer: Enih Rosmah, Ph.

D) Management of Forest Resources and Renewable Energy Master of Forestry Mulawarman University Please explain about phenolic compounds (the meaning, occurrence, how to obtain, role, and utilization)! 1. The meaning of Phenolic compounds Chi Tang Ho (1992) said that Phenolic compounds are a substance that possesses an aromatic ring bearing one or more hydroxy substituents, including functional derivatives (esters, methyl ethers, glycosides etc.) Randhir, Lin, & Shetty (2004) in Balasundram, Sundram & Samman (2005) said that Phenolic compounds are secondary metabolites that are derivatives of the pentose phosphate, shikimate, and phenylpropanoid pathways in plants Occurrence of Phenolic compounds 2. The occurrence of Phenolic Compounds The biosynthetic pathway of some phenolic compounds (Mustafa and Verpoorte, 2007)

a small-dashed line means multi-steps reactions

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(Randhir, et. al., 2004) 3. To obtain Phenolic compounds (Eldahshan, 2011) Extraction protocols: Powders of air dried leaves of carob (1 kg) w ere extracted by 70 % ethanol on cold till exhaustion. The solvent was distilled of in rotary evaporator at 55C till dryness. The extract was concentrated till constant weight 80 g and kept in vacuum desiccator over anhydrous calcium chloride. Ultraviolet spectrophotometric analysis: Chromatographically, pure materials dissolved in analytically pure methanol (definite concentration), were subjected to UV spectrophotometric investigation in 4 mL capacity quartz cells(1 cm thick) using a Carl Zeiss spectrophotometer

PMQ II. AlCl3, AlCl3/HCl, fused NaOAc/H3BO3 and NaOMe reagents were separately added to the methanolic solution of investigated material and UV measurements were then carried out. Nuclear magnetic resonance spectroscopic analysis: The NMR spectra were recorded on a Varian M ercury VX-300 NMR spectrometer. 1H spectra run at 300 and 500 MHz and 13C spectra were run at 75.46 MHz in deutrated dimethylsulphoxide (DMSO-d6). Chemical shifts are quoted in and were related to that of the solvents. The mass spectra were recorded on a Shimadzu GCMS-QP-1000EX mass spectrometer at 70 e.V. Isolation and identification: The isolation and purification of the phenolic components were achieved through the application of the concentrated extract (60 g) to a Sephadex LH-20 column (150x4.5 cm) and eluted with water followed by H2O-MeOH mixtures of decreasing polarities to yield five fractions (I-V). Compound (1) 22.0 mg and (2) 35.0 mg were isolated from fraction I (eluted with water) by polyamide column fractionation using H2O/MeOH (decreasing polarity) for elution then preparative paper chromatography (PPC) using HOAc15%. Compound (3) 8.3 mg and (4) 10.0 mg from fraction II (eluted with 50% MeOH). Compound (5) was separated from fraction III (eluted by 80% ) by Sephadex LH-20 column using saturated water butanol 11.7 mg. Purification of the compound achieved through PPC. Compound (6) 15.2 mg, (7) 8.0 mg and (8) 7.7 mg from fraction IV paper were chromatographically analyzed using preparative paper chromatography on Whatmann paper No. 3 and 6% acetic acid as a developing system. 4. Role Phenolic compounds Phenolic compounds role in oxidation processes, as either antioxidants or substrates in browning reactions in fruits (Robards, 1999). Phenolic compounds can act as protective agents, inhibitors, natural animal toxicants and pesticides against invading organisms, i.e. herbivores, nematodes, phytophagous insects, and fungal and bacterial pathogens. The scent and pigmentation conferred by other phenolics can attract symbiotic microbes, pollinators and animals that disperse fruits (http://en.wikipedia.org). Utilization Phenolic compounds Utilization Journal Antioxidant Food Chemistry 136 (2013) Food and Chemical Toxicology 57 (2013) Molecules 2010, 15 Food and Chemical Toxicology 46 (2008) Food Chemistry 99 (2006) anti-cholinesterase Food and Chemical Toxicology 57 (2013) Antibacterial Food Chemistry 130 (2012) 671678 Anticancer Molecules 2010, 15 Antimicrobial Food and Chemical Toxicology 46 (2008) Antimutagenic Mutation Research/Genetic Toxicology and Environmental Mutagenesis 1999

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Author Lee, J,H,. et. al. Costa, et. al. Dai, J,. and Mumper, R,J, Estevinho, et. al Balasundram, N,. et. al. Costa, et. al. Escuredoa, et. al. Dai, J,. and Mumper, R,J, Estevinho, et. al a, et. al

References: Balasundram, N,. Sundram, K,. and Samman, S,. 2006. Phenolic compounds in plants and agriindustrial by-products: Antioxidant activity, occurrence, and potential uses. Food Chemistry 99 (2006) 191203 Costa, P., Gonalves, S,. Valento, P,. Andrade, P,B,. Romano, A,. 2013. Accumulation of phenolic compounds in in vitro cultures and wild plants of Lavandula viridis LHr and th ir antioxidant and anti-cholinesterase potential. Food and Chemical Toxicology 57 (2013) 69 74 Dai, J,. and Mumper, R,J,. 2010. Plant Phenolics: Extraction, Analysis and Their Antioxidant and Anticancer Properties. Molecules 2010, 15, 7313-7352 Eldahshan O,A,. 2011. Isolation and Structure Elucidation of Phenolic Compounds of Carob Leaves Grown in Egypt. Current Research Journal of Biological Sciences 3(1): 52-55 Escuredoa, O,. Silva, L,R,. Valento, P,. Seijoa, M,C,. and Andrade, P,B,. 2012. Assessing Rubus honey value: Pollen and phenolic compounds content and antibacterial capacity. Food Chemistry 130 (2012) 671678 Estevinho, L,. Pereira, A,P,. Moreira, L,. Dias, L,G,. Pereira, E,. 2008. Antioxidant and antimicrobial effects of phenolic compounds extracts of Northeast Portugal honey. Food and Chemical Toxicology 46 (2008) 37743779 Ho, C.T., 1992. Phenolic Compounds in Food and Their Effects on Health I : Analysis, Occurrence, and Chemistry. ACS SYMPOSIUM SERIES: 2 7 Lee, J,H,. Park, K,H,. Lee, M,H,. Kim, M,T,. Seo, W,D,. Kim, J,Y,. Baek, I,Y,. Jang, D,S,. and Hac, T,J,. 2013. Id ntication, charact risation, and quantication of ph nolic compounds in the antioxidant activity-containing fraction from the seeds of Korean perilla (Perilla frutescens) cultivars. Food Chemistry 136 (2013) 843852 a, E,G,. Tostado, E,C,. Pia, G,L,. 1999. Antimutagenic effects of natural phenolic compounds in beans. Mutation Research/Genetic Toxicology and Environmental Mutagenesis Volume 441, Issue 1, 26 April 1999, Pages 19 Mustafa, N,R,. and Verpoorte, R,. 2007 Phenolic compounds in Catharanthus roseus. Phytochem Rev (2007) 6:243258 Randhir, R,. Lin, Y,T,. and Shetty, K,. 2004. Stimulation of phenolics, antioxidant and antimicrobial activities in dark germinated mung bean sprouts in response to peptide and phytochemical elicitors. Process Biochemistry. Volume 39, Issue 5, 30 January 2004, Pages 637646 Robards, K,. Prenzler, P,D,. Tucker, G,. Swatsitang, P,. and Glover, W,. 1999. Phenolic compounds and their role in oxidative processes in fruits. Food Chemistry. Volume 66, Issue 4, September 1999, Pages 401436 http://mtngrv.missouristate.edu/vgdp/phenolmain.htm

http://en.wikipedia.org