Biomimetic oxidative copolymerization of hydroxystilbenes and monolignols

Kim, Hoon; Rencoret, Jorge; Elder, Thomas J.; del Río, José C.; Ralph, John

doi:10.1126/sciadv.ade5519

Biomimetic oxidative copolymerization of hydroxystilbenes and monolignols

Journal Article · Wed Mar 08 00:00:00 EST 2023 · Science Advances

DOI:https://doi.org/10.1126/sciadv.ade5519· OSTI ID:1970347

^[1]; ^[2]; Elder, Thomas J. ^[3]; ^[2]; ^[4]

Univ. of Wisconsin, Madison, WI (United States); University of Wisconsin-Madison Wisconsin Energy Institute
Inst. de Recursos Naturales y Agrobiología de Sevilla (IRNAS), Seville (Spain)
USDA-Forest Service, Auburn, AL (United States)
Univ. of Wisconsin, Madison, WI (United States)

Hydroxystilbenes are a class of polyphenolic compounds that behave as lignin monomers participating in radical coupling reactions during the lignification. Here, we report the synthesis and characterization of various artificial copolymers of monolignols and hydroxystilbenes, as well as low-molecular-mass compounds, to obtain the mechanistic insights into their incorporation into the lignin polymer. Integrating the hydroxystilbenes, resveratrol and piceatannol, into monolignol polymerization in vitro, using horseradish peroxidase to generate phenolic radicals, produced synthetic lignins [dehydrogenation polymers (DHPs)]. Copolymerization of hydroxystilbenes with monolignols, especially sinapyl alcohol, by in vitro peroxidases notably improved the reactivity of monolignols and resulted in substantial yields of synthetic lignin polymers. The resulting DHPs were analyzed using two-dimensional NMR and 19 synthesized model compounds to confirm the presence of hydroxystilbene structures in the lignin polymer. The cross-coupled DHPs confirmed both resveratrol and piceatannol as authentic monomers participating in the oxidative radical coupling reactions during polymerization.

View Accepted Manuscript (DOE)

Research Organization:: Great Lakes Bioenergy Research Center (GLBRC), Madison, WI (United States)

Sponsoring Organization:: National Science Foundation; USDOE Office of Science (SC), Biological and Environmental Research (BER)

Grant/Contract Number:: SC0018409

OSTI ID:: 1970347

Journal Information:: Science Advances, Journal Name: Science Advances Journal Issue: 10 Vol. 9; ISSN 2375-2548

Publisher:: AAASCopyright Statement

Country of Publication:: United States

Language:: English

References (80)

Laccase-Catalyzed Dimerization of Hydroxystilbenes Ponzoni, Chiara; Beneventi, Elisa; Cramarossa, Maria Rita Advanced Synthesis & Catalysis, Vol. 349, Issue 8-9 https://doi.org/10.1002/adsc.200700043	journal	June 2007
Beiträge zur Erforschung des Lignins Freudenberg, K. Angewandte Chemie, Vol. 68, Issue 16 https://doi.org/10.1002/ange.19560681603	journal	August 1956
Characterization and analysis of the molecular weight of lignin for biorefining studies Tolbert, Allison; Akinosho, Hannah; Khunsupat, Ratayakorn Biofuels, Bioproducts and Biorefining, Vol. 8, Issue 6 https://doi.org/10.1002/bbb.1500	journal	June 2014
Biosynthesis, metabolism, molecular engineering, and biological functions of stilbene phytoalexins in plants Jeandet, Philippe; Delaunois, Bertrand; Conreux, Alexandra BioFactors, Vol. 36, Issue 5 https://doi.org/10.1002/biof.108	journal	August 2010
Regio- and Stereoselective Biomimetic Synthesis of Oligostilbenoid Dimers from Resveratrol Analogues: Influence of the Solvent, Oxidant, and Substitution Velu, Saraswati S.; Buniyamin, Irmaizatussyehdany; Ching, Lee Kiew Chemistry - A European Journal, Vol. 14, Issue 36 https://doi.org/10.1002/chem.200801575	journal	November 2008
Lignin from Tree Barks: Chemical Structure and Valorization Neiva, Duarte M.; Rencoret, Jorge; Marques, Gisela ChemSusChem, Vol. 13, Issue 17 https://doi.org/10.1002/cssc.202000431	journal	June 2020
Stilbenoids Shen, Tao; Xie, Chun-Feng; Wang, Xiao-Ning Natural Products https://doi.org/10.1007/978-3-642-22144-6_63	book	January 2013
About native components of extracts fromMaackia amurensis wood Kulesh, N. I.; Maksimov, O. B.; Fedoreev, S. A. Chemistry of Natural Compounds, Vol. 35, Issue 5 https://doi.org/10.1007/BF02323300	journal	September 1999
A potential role for sinapyl p-coumarate as a radical transfer mechanism in grass lignin formation Hatfield, Ronald; Ralph, John; Grabber, John H. Planta, Vol. 228, Issue 6, p. 919-928 https://doi.org/10.1007/s00425-008-0791-4	journal	July 2008
Regulation of stilbene biosynthesis in plants Dubrovina, A. S.; Kiselev, K. V. Planta, Vol. 246, Issue 4 https://doi.org/10.1007/s00425-017-2730-8	journal	July 2017
Quantitative evaluation of milling effects on lignin structure during the isolation process of milled wood lignin Fujimoto, Aya; Matsumoto, Yuji; Chang, Hou-Min Journal of Wood Science, Vol. 51, Issue 1 https://doi.org/10.1007/s10086-004-0682-7	journal	February 2005
Reactivity of syringyl quinone methide intermediates in dehydrogenative polymerization I: high-yield production of synthetic lignins (DHPs) in horseradish peroxidase-catalyzed polymerization of sinapyl alcohol in the presence of nucleophilic reagents Tobimatsu, Yuki; Takano, Toshiyuki; Kamitakahara, Hiroshi Journal of Wood Science, Vol. 56, Issue 3 https://doi.org/10.1007/s10086-009-1086-5	journal	December 2009
Solution-state 2D NMR of Ball-milled Plant Cell Wall Gels in DMSO-d ₆ Kim, Hoon; Ralph, John; Akiyama, Takuya BioEnergy Research, Vol. 1, Issue 1, p. 56-66 https://doi.org/10.1007/s12155-008-9004-z	journal	March 2008
Stilbenolignan from Maackia amurensis Kulesh, N. I.; Denisenko, V. A.; Maksimov, O. B. Phytochemistry, Vol. 40, Issue 3 https://doi.org/10.1016/0031-9422(95)00270-H	journal	October 1995
A comparison of lignin polymer models (DHPs) and lignins by 31P NMR spectroscopy Saake, Bodo; Argyropoulos, Dimitris S.; Beinhoff, Ottokar Phytochemistry, Vol. 43, Issue 2 https://doi.org/10.1016/0031-9422(96)00283-X	journal	September 1996
Pallidol, a resveratrol dimer from Cissus pallida Khan, Mushtaq A.; Nabi, Shah G.; Prakash, Satya Phytochemistry, Vol. 25, Issue 8 https://doi.org/10.1016/S0031-9422(00)81180-2	journal	July 1986
Stilbenoids from Cassia garrettiana Baba, Kimiye; Kido, Tadashi; Taniguchi, Masahiko Phytochemistry, Vol. 36, Issue 6 https://doi.org/10.1016/S0031-9422(00)89752-6	journal	August 1994
Synthetic studies on β-lactam antibiotics. VII. Mild removal of the benzyl ester protecting group with aluminum trichloride Tsuji, Teruji; Kataoka, Takahiro; Yoshioka, Mitsuru Tetrahedron Letters, Vol. 20, Issue 30 https://doi.org/10.1016/S0040-4039(01)86418-2	journal	January 1979
Unexpected variation in lignin Sederoff, Ronald R.; MacKay, John J.; Ralph, John Current Opinion in Plant Biology, Vol. 2, Issue 2 https://doi.org/10.1016/S1369-5266(99)80029-6	journal	April 1999
Lignin degradation and detoxification of eucalyptus wastes by on-site manufacturing fungal enzymes to enhance second-generation ethanol yield Schneider, Willian Daniel Hahn; Fontana, Roselei Claudete; Baudel, Henrique Macedo Applied Energy, Vol. 262 https://doi.org/10.1016/j.apenergy.2020.114493	journal	March 2020
Lignin biosynthesis and its integration into metabolism Vanholme, Ruben; De Meester, Barbara; Ralph, John Current Opinion in Biotechnology, Vol. 56 https://doi.org/10.1016/j.copbio.2019.02.018	journal	April 2019
Kinetic simulation of the thermal degradation of phenethyl phenyl ether, a model compound for the β-O-4 linkage in lignin Beste, Ariana; Buchanan, A. C. Chemical Physics Letters, Vol. 550 https://doi.org/10.1016/j.cplett.2012.08.040	journal	October 2012
Isorhapontigenin: A novel bioactive stilbene from wine grapes Fernández-Marín, María Isabel; Guerrero, Raúl F.; García-Parrilla, María Carmen Food Chemistry, Vol. 135, Issue 3 https://doi.org/10.1016/j.foodchem.2012.05.086	journal	December 2012
Resveratrol dimers, nutritional components in grape wine, are selective ROS scavengers and weak Nrf2 activators Li, Chang; Xu, Xiaofei; Tao, Zhihao Food Chemistry, Vol. 173 https://doi.org/10.1016/j.foodchem.2014.09.165	journal	April 2015
Compensated adiabatic inversion pulses: Broadband INEPT and HSQC Kupče, Eriks; Freeman, Ray Journal of Magnetic Resonance, Vol. 187, Issue 2 https://doi.org/10.1016/j.jmr.2007.05.009	journal	August 2007
Biological activity of piceatannol: Leaving the shadow of resveratrol Piotrowska, Hanna; Kucinska, Malgorzata; Murias, Marek Mutation Research/Reviews in Mutation Research, Vol. 750, Issue 1 https://doi.org/10.1016/j.mrrev.2011.11.001	journal	January 2012
α-Glucosidase inhibitors from the seeds of Syagrus romanzoffiana Lam, Sio-Hong; Chen, Jhong-Min; Kang, Chao-Jou Phytochemistry, Vol. 69, Issue 5 https://doi.org/10.1016/j.phytochem.2007.12.004	journal	March 2008
Unusual stilbenoids and a stilbenolignan from seeds of Syagrus romanzoffiana Lam, Sio-Hong; Lee, Shoei-Sheng Phytochemistry, Vol. 71, Issue 7 https://doi.org/10.1016/j.phytochem.2010.01.013	journal	May 2010
Radical coupling reactions of piceatannol and monolignols: A density functional theory study Elder, Thomas; Carlos del Río, José; Ralph, John Phytochemistry, Vol. 164 https://doi.org/10.1016/j.phytochem.2019.04.003	journal	August 2019
Metabolism and roles of stilbenes in plants Chong, Julie; Poutaraud, Anne; Hugueney, Philippe Plant Science, Vol. 177, Issue 3 https://doi.org/10.1016/j.plantsci.2009.05.012	journal	September 2009
Biomimic transformation of resveratrol Takaya, Yoshiaki; Terashima, Kenji; Ito, Junko Tetrahedron, Vol. 61, Issue 43 https://doi.org/10.1016/j.tet.2005.08.023	journal	October 2005
Characterization and Elimination of Undesirable Protein Residues in Plant Cell Wall Materials for Enhancing Lignin Analysis by Solution-State Nuclear Magnetic Resonance Spectroscopy Kim, Hoon; Padmakshan, Dharshana; Li, Yanding Biomacromolecules, Vol. 18, Issue 12 https://doi.org/10.1021/acs.biomac.7b01223	journal	November 2017
A Comprehensive Review on the Chemotherapeutic Potential of Piceatannol for Cancer Treatment, with Mechanistic Insights Seyed, Mohamed Ali; Jantan, Ibrahim; Bukhari, Syed Nasir Abbas Journal of Agricultural and Food Chemistry, Vol. 64, Issue 4 https://doi.org/10.1021/acs.jafc.5b05993	journal	January 2016
Variability in Lignin Composition and Structure in Cell Walls of Different Parts of Macaúba ( Acrocomia aculeata ) Palm Fruit Rencoret, Jorge; Kim, Hoon; Evaristo, Anderson B. Journal of Agricultural and Food Chemistry, Vol. 66, Issue 1 https://doi.org/10.1021/acs.jafc.7b04638	journal	December 2017
Lignin Monomers from beyond the Canonical Monolignol Biosynthetic Pathway: Another Brick in the Wall del Río, José C.; Rencoret, Jorge; Gutiérrez, Ana ACS Sustainable Chemistry & Engineering, Vol. 8, Issue 13 https://doi.org/10.1021/acssuschemeng.0c01109	journal	March 2020
Density Functional Theory Study of Spirodienone Stereoisomers in Lignin Elder, Thomas; Berstis, Laura; Beckham, Gregg T. ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 8 https://doi.org/10.1021/acssuschemeng.7b01373	journal	July 2017
Monolignol Benzoates Incorporate into the Lignin of Transgenic Populus trichocarpa Depleted in C3H and C4H Kim, Hoon; Li, Quanzi; Karlen, Steven D. ACS Sustainable Chemistry & Engineering, Vol. 8, Issue 9 https://doi.org/10.1021/acssuschemeng.9b06389	journal	February 2020
Chemistry and Biology of Resveratrol-Derived Natural Products Keylor, Mitchell H.; Matsuura, Bryan S.; Stephenson, Corey R. J. Chemical Reviews, Vol. 115, Issue 17 https://doi.org/10.1021/cr500689b	journal	April 2015
Determination of Stilbenes (δ-viniferin, trans-astringin, trans-piceid, cis- and trans-resveratrol, ε-viniferin) in Brazilian Wines Vitrac, Xavier; Bornet, Aurélie; Vanderlinde, Regina Journal of Agricultural and Food Chemistry, Vol. 53, Issue 14 https://doi.org/10.1021/jf050122g	journal	June 2005
Structural Characterization of Wheat Straw Lignin as Revealed by Analytical Pyrolysis, 2D-NMR, and Reductive Cleavage Methods del Río, José C.; Rencoret, Jorge; Prinsen, Pepijn Journal of Agricultural and Food Chemistry, Vol. 60, Issue 23 https://doi.org/10.1021/jf301002n	journal	December 2011
Derivatization Followed by Reductive Cleavage (DFRC Method), a New Method for Lignin Analysis: Protocol for Analysis of DFRC Monomers Lu, Fachuang; Ralph, John Journal of Agricultural and Food Chemistry, Vol. 45, Issue 7 https://doi.org/10.1021/jf970258h	journal	July 1997
DFRC Method for Lignin Analysis. 1. New Method for β-Aryl Ether Cleavage: Lignin Model Studies Lu, Fachuang; Ralph, John Journal of Agricultural and Food Chemistry, Vol. 45, Issue 12 https://doi.org/10.1021/jf970539p	journal	December 1997
Regioselective Oxidative Coupling of 4-Hydroxystilbenes: Synthesis of Resveratrol and ε-Viniferin (E)-Dehydrodimers Sako, Magoichi; Hosokawa, Hiroyuki; Ito, Tetsuro The Journal of Organic Chemistry, Vol. 69, Issue 7 https://doi.org/10.1021/jo035791c	journal	March 2004
Radical Coupling Reactions in Lignin Synthesis: A Density Functional Theory Study Sangha, Amandeep K.; Parks, Jerry M.; Standaert, Robert F. The Journal of Physical Chemistry B, Vol. 116, Issue 16 https://doi.org/10.1021/jp2122449	journal	April 2012
Computational Study of Bond Dissociation Enthalpies for a Large Range of Native and Modified Lignins Kim, Seonah; Chmely, Stephen C.; Nimlos, Mark R. The Journal of Physical Chemistry Letters, Vol. 2, Issue 22 https://doi.org/10.1021/jz201182w	journal	October 2011
Theoretical Study of the Remarkably Diverse Linkages in Lignin Parthasarathi, R.; Romero, Raymond A.; Redondo, Antonio The Journal of Physical Chemistry Letters, Vol. 2, Issue 20 https://doi.org/10.1021/jz201201q	journal	October 2011
A Novel Cyclooxygenase-Inhibitory Stilbenolignan from the Seeds of Aiphanes aculeata Lee, Dongho; Cuendet, Muriel; Vigo, Jose Schunke Organic Letters, Vol. 3, Issue 14 https://doi.org/10.1021/ol015985j	journal	June 2001
Lignins: Natural polymers from oxidative coupling of 4-hydroxyphenyl- propanoids Ralph, John; Lundquist, Knut; Brunow, Gösta Phytochemistry Reviews, Vol. 3, Issue 1-2, p. 29-60 https://doi.org/10.1023/B:PHYT.0000047809.65444.a4	journal	January 2004
Solution-state 2D NMR of ball-milled plant cell wall gels in DMSO-d6/pyridine-d5 Kim, Hoon; Ralph, John Org. Biomol. Chem., Vol. 8, Issue 3 https://doi.org/10.1039/B916070A	journal	January 2010
Incorporation of catechyl monomers into lignins: lignification from the non-phenolic end via Diels–Alder cycloaddition? Ando, Daisuke; Lu, Fachuang; Kim, Hoon Green Chemistry, Vol. 23, Issue 22 https://doi.org/10.1039/D1GC03022A	journal	January 2021
Natural stilbenoids: distribution in the plant kingdom and chemotaxonomic interest in Vitaceae Rivière, Céline; Pawlus, Alison D.; Mérillon, Jean-Michel Natural Product Reports, Vol. 29, Issue 11 https://doi.org/10.1039/c2np20049j	journal	January 2012
Biomimetic Preparation of the Racemic Modifications of the Stilbenolignan Aiphanol and Three Congeners Chand, Satish; Banwell, Martin G. Australian Journal of Chemistry, Vol. 60, Issue 4 https://doi.org/10.1071/CH07044	journal	January 2007
The Chinese Herb Isolate Isorhapontigenin Induces Apoptosis in Human Cancer Cells by Down-regulating Overexpression of Antiapoptotic Protein XIAP Fang, Yong; Yu, Yonghui; Hou, Qi Journal of Biological Chemistry, Vol. 287, Issue 42 https://doi.org/10.1074/jbc.M112.389494	journal	October 2012
Efficient Total Synthesis of Piceatannol via (E)-Selective Wittig–Horner Reaction Young Han, Su; Suck Lee, Hyun; Hye Choi, Da Synthetic Communications, Vol. 39, Issue 8 https://doi.org/10.1080/00397910802528944	journal	March 2009
Resveratrol Is Rapidly Metabolized in Athymic (Nu/Nu) Mice and Does Not Inhibit Human Melanoma Xenograft Tumor Growth Niles, Richard M.; Cook, Carla P.; Meadows, Gary G. The Journal of Nutrition, Vol. 136, Issue 10 https://doi.org/10.1093/jn/136.10.2542	journal	October 2006
Variation in Lignin Content and Composition (Mechanisms of Control and Implications for the Genetic Improvement of Plants) Campbell, M. M.; Sederoff, R. R. Plant Physiology, Vol. 110, Issue 1 https://doi.org/10.1104/pp.110.1.3	journal	January 1996
Sequencing around 5-Hydroxyconiferyl Alcohol-Derived Units in Caffeic Acid O -Methyltransferase-Deficient Poplar Lignins Lu, Fachuang; Marita, Jane M.; Lapierre, Catherine Plant Physiology, Vol. 153, Issue 2 https://doi.org/10.1104/pp.110.154278	journal	April 2010
Lignin Biosynthesis and Structure Vanholme, R.; Demedts, B.; Morreel, K. Plant Physiology, Vol. 153, Issue 3, p. 895-905 https://doi.org/10.1104/pp.110.155119	journal	May 2010
Hydroxystilbenes Are Monomers in Palm Fruit Endocarp Lignins Carlos del Río, José; Rencoret, Jorge; Gutiérrez, Ana Plant Physiology, Vol. 174, Issue 4 https://doi.org/10.1104/pp.17.00362	journal	June 2017
Hydroxystilbene Glucosides Are Incorporated into Norway Spruce Bark Lignin Rencoret, Jorge; Neiva, Duarte; Marques, Gisela Plant Physiology, Vol. 180, Issue 3 https://doi.org/10.1104/pp.19.00344	journal	April 2019
Identification of the structure and origin of a thioacidolysis marker compound for ferulic acid incorporation into angiosperm lignins (and an indicator for cinnamoyl CoA reductase deficiency): Marker for ferulic acid incorporation into lignins Ralph, John; Kim, Hoon; Lu, Fachuang The Plant Journal, Vol. 53, Issue 2 https://doi.org/10.1111/j.1365-313X.2007.03345.x	journal	October 2007
Nature’s assembly line: biosynthesis of simple phenylpropanoids and polyketides Yu, Oliver; Jez, Joseph M. The Plant Journal, Vol. 54, Issue 4 https://doi.org/10.1111/j.1365-313X.2008.03436.x	journal	May 2008
Metabolic engineering of novel lignin in biomass crops Vanholme, Ruben; Morreel, Kris; Darrah, Chiarina New Phytologist, Vol. 196, Issue 4 https://doi.org/10.1111/j.1469-8137.2012.04337.x	journal	October 2012
Synthesis and pharmacological evaluation of glycosides of resveratrol, pterostilbene, and piceatannol Shimoda, Kei; Kubota, Naoji; Uesugi, Daisuke Annals of the New York Academy of Sciences, Vol. 1348, Issue 1 https://doi.org/10.1111/nyas.12836	journal	August 2015
Abnormal Lignin in a Loblolly Pine Mutant Ralph, J. Science, Vol. 277, Issue 5323 https://doi.org/10.1126/science.277.5323.235	journal	July 1997
Lignin Biosynthesis Boerjan, Wout; Ralph, John; Baucher, Marie Annual Review of Plant Biology, Vol. 54, Issue 1, p. 519-546 https://doi.org/10.1146/annurev.arplant.54.031902.134938	journal	June 2003
AlCl₃–N,N-Dimethylaniline: A Novel Benzyl and Allyl Ether Cleavage Reagent Akiyama, Takahiko; Hirofuji, Hajimu; Ozaki, Shoichiro Bulletin of the Chemical Society of Japan, Vol. 65, Issue 7 https://doi.org/10.1246/bcsj.65.1932	journal	July 1992
The constituents of Scirpus fluviatilis(Torr). A. Gray. I. The structures of two new hydroxystilbene dimers, scirpusin A and B. Nakajima, Kaoru; Taguchi, Heihachiro; Endo, Tohru Chemical and Pharmaceutical Bulletin, Vol. 26, Issue 10 https://doi.org/10.1248/cpb.26.3050	journal	January 1978
Indonesian Medicinal Plants. XVIII. Kompasinol A, a New Stilbeno-Phenylpropanoid from the Bark of Koompassia malaccensis (Fabaceae). Kobayashi, Motomasa; Mahmud, Taifo; Yoshioka, Naoki CHEMICAL & PHARMACEUTICAL BULLETIN, Vol. 44, Issue 12 https://doi.org/10.1248/cpb.44.2249	journal	January 1996
Isolation and Biomimetic Synthesis of Anti-inflammatory Stilbenolignans from Gnetum cleistostachyum Yao, Chun-Suo; Lin, Mao; Wang, Lin Chemical and Pharmaceutical Bulletin, Vol. 54, Issue 7 https://doi.org/10.1248/cpb.54.1053	journal	January 2006
Structures of Novel Norstilbene Dimer, Longusone A, and Three New Stilbene Dimers, Longusols A, B, and C, with Antiallergic and Radical Scavenging Activities from Egyptian Natural Medicine Cyperus longus Morikawa, Toshio; Xu, Fengming; Matsuda, Hisashi Chemical and Pharmaceutical Bulletin, Vol. 58, Issue 10 https://doi.org/10.1248/cpb.58.1379	journal	January 2010
Reactivity of syringyl quinone methide intermediates in dehydrogenative polymerization. Part 2: pH effect in horseradish peroxidase-catalyzed polymerization of sinapyl alcohol Tobimatsu, Yuki; Takano, Toshiyuki; Kamitakahara, Hiroshi Holzforschung, Vol. 64, Issue 2 https://doi.org/10.1515/hf.2010.027	journal	February 2010
Stilbene and Chalcone Synthases: Related Enzymes with Key Functions in Plant-Specific Pathways Schröder, Gudrun; Schröder, Gudrun Zeitschrift für Naturforschung C, Vol. 45, Issue 1-2 https://doi.org/10.1515/znc-1990-1-202	journal	February 1990
Stilbenoid chemistry from wine and the genus Vitis, a review Pawlus, Alison D.; Waffo-Téguo, Pierre; Shaver, Jonah OENO One, Vol. 46, Issue 2 https://doi.org/10.20870/oeno-one.2012.46.2.1512	journal	June 2012
“Non-Taxifolin” Derived Flavonolignans: Phytochemistry and Biology Chambers, Christopher; Valentova, Katerina; kren, Vladimir Current Pharmaceutical Design, Vol. 21, Issue 38 https://doi.org/10.2174/1381612821666151002112720	journal	November 2015
Pharmacometrics of Stilbenes: Seguing Towards the Clinic Roupe, Kathryn; Remsberg, Connie; Yanez, Jaime Current Clinical Pharmacology, Vol. 1, Issue 1 https://doi.org/10.2174/157488406775268246	journal	January 2006
Ruthenium Chloride—Induced Oxidative Cyclization of Trans-Resveratrol to (±)-ε-Viniferin and Antimicrobial and Antibiofilm Activity Against Streptococcus pneumoniae Yadav, Mukesh Kumar; Mailar, Karabasappa; Nagarajappa Masagalli, Jagadeesh Frontiers in Pharmacology, Vol. 10 https://doi.org/10.3389/fphar.2019.00890	journal	August 2019
Lignin Composition and Structure Differs between Xylem, Phloem and Phellem in Quercus suber L. Lourenço, Ana; Rencoret, Jorge; Chemetova, Catarina Frontiers in Plant Science, Vol. 7 https://doi.org/10.3389/fpls.2016.01612	journal	October 2016
Biological Activities of Stilbenoids Akinwumi, Bolanle; Bordun, Kimberly-Ann; Anderson, Hope International Journal of Molecular Sciences, Vol. 19, Issue 3 https://doi.org/10.3390/ijms19030792	journal	March 2018
Cytotoxicity of Labruscol, a New Resveratrol Dimer Produced by Grapevine Cell Suspensions, on Human Skin Melanoma Cancer Cell Line HT-144 Nivelle, Laetitia; Hubert, Jane; Courot, Eric Molecules, Vol. 22, Issue 11 https://doi.org/10.3390/molecules22111940	journal	November 2017

Similar Records

Hydroxystilbene Glucosides Are Incorporated into Norway Spruce Bark Lignin

Journal Article · Thu Jun 27 20:00:00 EDT 2019 · Plant Physiology (Bethesda) · OSTI ID:1508886

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Biomimetic oxidative copolymerization of hydroxystilbenes and monolignols

Citation Formats

References (80)

Similar Records

Related Subjects