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Variations in the Heterogeneity of the Decay of the Fluorescence In Reprinted from the Journal of the American Chemical Society, 1990,IIZ. Copyright @ 1990by the American Chemical Society and reprinted by permission of the copyright owner. Variationsin the Heterogeneityof the Decayof the Fluorescencein Six ProcyanidinDimers DongbwanCbo,t Ru~iangTian,t Lawrence J. Porter,' Richard W. Hemingway,.l and Wayne L. Mattice.' Contribution from the Institute of Polymer Science. The University of Akron. Akron, Ohio 44325- 3909, Department of Chemistry, Bowling Green State University. Bowling Green. Ohio 43403. Chemistry Division. Department of Scientific and Industrial Research.Petone, New Zealand, and Southern Forest Experiment Station. Pineville. Louisiana 71360. ReceivedOctober 10, 1989 Abstract: The decay of the fluorescence has been measured in 1.4-dioxane for six dimen of (lR.3R)-(-)-epicatechin and (2R.3S)-(+)-catechin. hereafter denoted simply epicatechin and catechin. The dimen are epicatechin-(4,8-+8)-catechin. epicatechin-(4.8-8)-epicatechin. catechin-( 4a--8)-catechin. catechin-( 4a--8 )-epicatechin. epicatechin-( 4,8-6)-epicatechin. and epicatechin-(4,8-+8;2,8-O-7)-epicatechin. The monomers and the bridged dimer have a fluorescence that decays as a single e~ponential. The remaining five dimen have a heterogeneousdecay that can be described by the sum of two exponentials. The heterogeneity is most apparent in the two dimen with 4a--8 interflavan bonds. In view of the molecular origin of the heterogeneousdecay in the presenceof two rotational isomen at the interflavan bond, polymeric JX"CXYanidinswith predominantly a stereochemistryfor the interflavan bond at C(4) should be more disordered and more compact than those with predominantly .8 stereochemistry. The ~t commonnaturally occurring polymeric procyanidins higher polymers. Upon excitation near 280 nm in dilute solution are polymersof two 2.3-flavan-3-o1s.(2R.3R)-(-)-epicatechin and in 1,4-dioxane, both monomers show a single emission band at (2R.3S)-(+ )-catechin.hereafter referred to simply as epicatechin 320-324 nm.II.12 The decay of the intensity of the nuorescence, and catechin. Thesepolymers are found in the leaves.fruits. and /(t). can be described by a single exponential. barks of many woodyand herbaceousplants.1 Interest in these /(t) = a exp(-tIT) (J) polymers is increasingbecause of their potential as a renewable source of useful chemicals.1their probable use by plants as a The nuorescence lifetimes, T, for the two monomers are indis- defensemechanism.2 and their formation of complexeswith a tinguishable.11 Higher oligomers exhibit an emission maximum variety of naturally occurring and synthetic polymers.3-1 in the same spectral region, but with a lower nuorescencequantum An interflavan bond from C( 4) of one monomer unit to C(8) yield, Q, than that obtained with the monomers.II.12 Although of its neighOOris the ~t commonlinkage between monomer units a ronstrained dimer, procyanidin A J, exhibits a nuorescence decay in the naturally occurring polymers.' Interflavan bonds from that can be described by ~ I, two unconstrained dimers, pro- C(4) to C(6) alsooccur. Figure I depictsthe covalentstructures cyanidins 8 J and 87, exhibit a heterogeneous decay that requires of six dimers of catechin and/or epicatechin. The trivial no- the sum of two exponentials for an adequate description.11 menclature of the six unbridged dimers is procyanidin BI. B2. /(t) = al exp( -t ITI) + a2 exp(-t I T2) (2) B3. 84. B5. and B7. The full nomenclaturedescribed by Hem- ingway et al.9 is epicatechin-(4p--8)-catechin. epicatechin- (4.8-8 )-epicatechin.catechin-( 4a-+8)-a techin. catechin-( 4a-+- (I) Hemingway. R. W., Karcbely. J. J.. Eds. Chemistry and SlglliftCGN:e o/ConJellSu TannillS; Plenum PIal: New York, 1989. 8)-epicatechin. epicatechin-(4p-6)-epicatechin. and epi- (2) Haslam. E. BlocMm. J. 1974. 139. 285. catechin-(4p-6)-atechin. respectively. Thesenames are based (3) Oh, H. I.; Hoff. J. E.; ArmstfODJ, G. S.; Hoff. L. A. J. Agrlc. F()Od on the constituent monomer units and the location and stereo- Chern. 1980, 18. 394. (4) Hagerman, A. E.; Butler. L G. J. BIoi. Chern. 1981. 156,4494. chemistryof the interflavanbond betweenmonomer units. Figure (5) Bergmann. W. R.; Mattice, W. L ACS Symp. SQ. 1987, No. 358, 162- 2 depictsthe covalentstructure of two bridgeddimers. procyanidin (6) Tilstra. L. F.; Maeda. H.; Mattice, W. L. J. CAem.Soc.. Perk/" TrGlU. A I and A2. Their longer names are epicatechin-(4p-8;2P- 11988, 1613. o-7)-catechin and epicatechin-(4p-8;2p-O-7)-epicatechin. (7) olstra, L F.; ClIo. D.; Bergmann, W. R.; Mattice, W. L.ln Chemistry respectively. The bridges from C(2) to C(7) in procyanidin Al olld Slglliftco/lt'e 0/ CoIIIlellSed TollllillS; Hemingway, R. W., Karcbesy, J. J., Eds.; Plenum Press: New York, 1989; P 335. and A2 prevent internal rotation about the interflavan bond. (8) Thompson. R. S.; Jaajues, D.; Hulam. E.; Tanner, R. J. N. J. CArm. Sinceit was first reporteda few yearsago.lo,ll the fluorescence Soc., Perk/" TrollS. 1 1972, 1387. of the oligomeric procyanidins has played an important role in (9) Hemingway, R. W.; Foo, t. Y.; Porter, L J. J. Chem. Soc.. Perki" the developmentof an understandingof the conformationsof the TrollS. I 1982, 1209. (10) Bergmann, W. R.;Barkley. M. D.; Mattice. W. L. PoI,m. Prep'. (Am. Chem. Soc., DID. PoI,m. Chrm.) 1986, 17 (2), 320. (II) Bergmann. W. R.; Barkley, M. D.; Hemingway, R. W.; Mattice. W. 'The University or Akron. I Bowling Green State University. L. J. Am. CAem. Soc. 1987, 109,6614. Depanment or Scientific and Industrial Research. (12) Cho, D.; Porter, L J.; Hemingway. R. W.; Mattice, W. L. PoI...lMr J. Southern Forest Experiment Station. 1989,30. 19S5. 4274 J. Am. C"~m.Soc.. Vol. 111.No. 11.1990 Cho~, 0/. two rotational isomers deduced from the analysis of the 81 ("pH 82 fluorescence decay curves for procyanidins BI and B7,Ieads to O HO .0:: the conclusion that the polymers are disordered and more compact HOr("r'° ~ than polystyrene chains of the same molecular weight. ~. ) ~...VOH.04 ,("tON (It ,o~"r'..~ HO 'OH0 0:OH A more extensi\'C examination of thed~y of the nuoresceJU I ," in tbis class of compounds is reported here. Reported for the first time are tbe decays of the nuorescences of procyanidins B2, B3, ~ " c.t OH ""OH 84, 85, and A2. While confirming the earlier conclusions aOOut the origin of the heterogeneous nuorescence d«ay from rotational isomerism, the data for the more extensi\'C set of' dimers show that there is a mucb broader range for the relative contributions of tbe two terms in cq 2 than was apparent from the study of pr<>- cyanidins Bl and 87. When combined with rotational isomeric HO~: state theory, this result bas profound implications for the con- 831GQ::x0:'. formational versatility of the polymeric procyanidins. It implia tbat plants can manipulate the stiffness and the extension of their OH OH polymeric procyanidins over a broad range by manipulation of the location and stereochemistry of the interfiavan bond. Experimental Methods and Details Catechin and epicatKhin were purchased from Sigma Chemical Co. The details of the preparation and purirlCation of the dimen and char- aCterization via 'JC nuclear maanetic resonance, spccirH: rotation. and FAB mass spectrometry.12 have been described elsewhere. ILlS-I? 1.4- Dioxane (spectrophotometric grade) purchased from Aldrich Chemical Co. was uted without funber purification. FrabJy prepared loIutions were IISecJtbnxaah tbis study due to the seasiiMty of loIutions of the sampia to ezpllUn to lilbt f« lona periods 01 ti~ OoH 6c.. -. Ultraviolet absorption measurements were performed at ambient temperature with a Perkin-Elmer Lambda Array 3840 UV /vis spectro- photometer cquiwcd with a photodilxle array and a deuterium lamp and OH OH interfaced with Perkin-Elmer Computerized Spectroscopic Software. FII- I. ~leat structuresof six un~ dimers.PrOC)'anMSim: 8 Absorbences at 29S nm for the monomen and 290 nm for the dimen. I. which were the wavelengths used for excitation in the nuoresccnce life- epicatechin-(4.8-8)-cat~hin: 82. epicatechin-(4.8-8)-epicat~hin; 83. time measurements. were in the range of 0.01-0.11. catechin-(4a-8)-cat~hjn: 84. catechin-(4a-8)-epicatechin; 8S. epi- Time-ra()!ved nu«accncc measurements achieved by time-correlated catechin-(4.8-6)-epic.t~hin: 87. epicatechin-(48-6)-catechin. single-photon counting"'" were used to determine the decay curves for the nu~ of the monomeric and dimeric procyanidins in solution. The excitation source was a Model 102 ultrafast dye laser (Coherence Co.). synchrtWlOUslypwnpeci by a frequency doubled. mIxic.locked Model Alltara 16-5 Nd:Y AG laser (Cobercncc Co.). A 1220 cavity dumper (Coherence Co.) was IISecJin the dye laser systems to provide selectable ootIKJt IKJlserepetition rates. A Model S-14A autCK:orTClator(Inred Co.) was used to measure the temlMJral width of the IKJlscemitted from a hip repetition rate mcxIc-1ockcd laser. The fwhm (full width. half maximum) or the dye laser pulse wu about 4 S-. The fwhm of the instrumental FcsIX'fISCfunction was about S80 s-. A repetition rate of S.4 MHz wu used with the time-to-amplitude amverler. An R928 photomultiplier. 01 manufactured by Hamamatsu Corp., was used. The filter used was a 30S-nm cutoff filter (WG-30S. Rolyn Arcadia. CA). A counting rate OH of aboot 18K counts/s was used for detecting the decay of the fluora- ccIIcc. The collection of data was amtinued until the decay curves had above 2OK counts in the peak. The d«8y curves were stored in the ranac of G-441 channels. Time calibration was 0.03623 ns/channel. The data ()~ aatuisition time required was usuaRy in the range of 2()-40 s. Electronics manufactured by EG &;.
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