Abstract
We used solvent extractions, SiO2 column chromatographies, and HPLC to isolate from the bark of Thanakha (Hesperethusa crenulata L) an active crystalline compound for absorbing UV-A radiation (320 to 380 nm). Analyses of low-and high-resolution FAB-MS revealed a compound, named marmesin, with a formula of C14H14O4 and a molecular mass of 246. To determine its chemical structure, we conducted 300 MMz NMR analyses using various probes,1H,13C, and DEPT13C. Our NMR data showed a structure of 2,3-dihydro-2(1 -hydroxy-1 -methylethyl)-furanocoumarin. This active compound contains UV-absorbing chromophores, an aromatic ring, a double bond at C3-C4, and a carbonyl at C2. Its λmax is 335 nm, indicating that marmesin could be commercially useful as a natural UV-A-filtering product
Literature cited
Charles JR Jacqlynn B (1993) The Aldrich Library of13C and1H NMR Spectra, Ed 1, Vol 2. Aldrich Chemical Company, USA, p 1311
Cockell CS (1998) Biological effects of high ultraviolet radiation on early earth a theoretical evaluation. J Theor Biol 193: 717–729
Duthie MS, Kimber I, Norval M (1999) The effects of ultraviolet radiation on the human immune system. Br J Dermatol 140: 995–1009
Elgamal MHA, Elewa NH, Elkhrisy EAM, Duddeck H (1979) 13C NMR chemical shifts and carbon-proton coupling constants of some furocoumarins and furochromones. Phytochem 18: 139–143
Hawk JL (1999) Sunlight and health. BMJ 319: 1066–1067
Hockwin O, Kojima M, Sakamoto Y, Wegener A, Shui YB, Sasaki KJ (1999) UV damage to the eye lens: Further results from animal model studies. Epidemiol 9: 39–47
Murray RD, Sutcliffed M, Maccabe PH (1971) Claisen rearrangements-IV: Oxidative cyclisation of two coumarin o-isoprenylphenols. Tetrahed 27: 4901–4906
Silverstein RM, Bassler GC, Morrill TC (1991) Spectrometric identification of organic compounds, Ed 5. John Wiley & Sons, New York, p 19
van der Leun JS (1996) UV radiation from sunlight: Summary, conclusions and recommendations. J Photochem Photobiol B 35: 237–244
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Joo, SH., Lee, SC. & Kim, SK. UV absorbent, marmesin, from the bark of Thanakha,Hesperethusa crenulata L.. J. Plant Biol. 47, 163–165 (2004). https://doi.org/10.1007/BF03030648
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DOI: https://doi.org/10.1007/BF03030648