Synthesis and plant growth inhibitory activity of N-trans-cinnamoyltyramine: its possible inhibition mechanisms and biosynthesis pathway

References

• Back K. 2001. Hydroxycinnamic acid amides and their possible utilization for enhancing agronomic traits. Plant Pathol J. 17:123–127.
   Google Scholar
• Beckie HJ, Heap IM, Smeda RJ, Hall LM. 2000. Screening for herbicide resistance in weeds. Weed Technol. 14:428–445. doi: 10.1614/0890-037X(2000)014[0428:SFHRIW]2.0.CO;2
   Web of Science ®Google Scholar
• Bhadoria PBS. 2010. Allelopathy: a natural way towards weed management. Am J Exp Agric. 1:7–20.
   Google Scholar
• Bibikova T, Gilroy S. 2003. Root hair development. J Plant Growth Regul. 21:383–415. doi: 10.1007/s00344-003-0007-x
   Web of Science ®Google Scholar
• Blum U, Shafer SR, Lehman ME. 1999. Evidence for inhibitory allelopathic interactions involving phenolic acids in field soils: concepts vs. an experimental model. Crit Rev Plant Sci. 18:673–693. doi: 10.1016/S0735-2689(99)00396-2
   Web of Science ®Google Scholar
• Cutillo F, D’Abrosca B, DellaGreca M, Di Marino C, Golino A, Previtera L, Zarrelli A. 2003. Cinnamic acid amides from Chenopodium album: effects on seeds germination and plant growth. Phytochemistry. 64:1381–1387. doi: 10.1016/S0031-9422(03)00511-9
   PubMed Web of Science ®Google Scholar
• Dam NM, Tytgat TOG, Kirkegaard JA. 2008. Root and shoot glucosinolates: a comparison of their diversity, function and interactions in natural and managed ecosystems. Phytochem Rev. 8:171–186.
   Web of Science ®Google Scholar
• Dayan FE, Duke SO. 2014. Natural compounds as next-generation herbicides. Plant Physiol. 166:1090–1105. doi: 10.1104/pp.114.239061
   PubMed Web of Science ®Google Scholar
• Einhellig FA. 1994. Mechanism of action of allelochemicals in allelopathy. Am Chem Soc. 582:96–116.
   Google Scholar
• Feng X-H, Zhao Y, Bottino PJ, Kung S. 1993. Cloning and characterization of a novel member of protein kinase family from soybean. Biochim Biophys Acta BBA – Gene Struct Expr. 1172:200–204. doi: 10.1016/0167-4781(93)90295-O
   PubMed Web of Science ®Google Scholar
• Fürstner A. 2004. Total syntheses and biological assessment of Macrocyclic glycolipids. Eur J Org Chem. 2004:943–958. doi: 10.1002/ejoc.200300728
   Web of Science ®Google Scholar
• Hasegawa K, Mizutani J, Kosemura S, Yamamura S. 1992. Isolation and identification of lepidimoide, a new allelopathic substance from mucilage of germinated cress seeds. Plant Physiol. 100:1059–1061. doi: 10.1104/pp.100.2.1059
   PubMed Web of Science ®Google Scholar
• Herrmann K. 1995. The Shikimate pathway: early steps in the biosynthesis of aromatic compounds. Plant Cell. 7:907–919. doi: 10.1105/tpc.7.7.907
   PubMed Web of Science ®Google Scholar
• Hosoi K, Yoshida S, Hasegawa M. 1970. L-Tyrosine carboxy-lyase of barley roots. Plant Cell Physiol. 11:899–906. doi: 10.1093/oxfordjournals.pcp.a074581
   Web of Science ®Google Scholar
• Iqbal Z, Hiradate S, Noda A, Isojima S-I, Fujii Y. 2002. Allelopathy of buckwheat: assessment of allelopathic potential of extract of aerial parts of buckwheat and identification of fagomine and other related alkaloids as allelochemicals. Weed Biol Manag. 2:110–115. doi: 10.1046/j.1445-6664.2002.00055.x
   Google Scholar
• Jahangir M, Abdel-Farid IB, Kim HK, Choi YH, Verpoorte R. 2009. Healthy and unhealthy plants: the effect of stress on the metabolism of Brassicaceae. Environ Exp Bot. 67:23–33. doi: 10.1016/j.envexpbot.2009.06.007
   Web of Science ®Google Scholar
• Kim B, Byun BY, Mah J-H. 2012. Biogenic amine formation and bacterial contribution in Natto products. Food Chem. 135:2005–2011. doi: 10.1016/j.foodchem.2012.06.091
   PubMed Web of Science ®Google Scholar
• Klempien A, Kaminaga Y, Qualley A, Nagegowda DA, Widhalm JR, Orlova I, Shasany AK, Taguchi G, Kish CM, Cooper BR, et al. 2012. Contribution of CoA Ligases to benzenoid biosynthesis in petunia flowers. Plant Cell. 24:2015–2030. doi: 10.1105/tpc.112.097519
   PubMed Web of Science ®Google Scholar
• Knezevic SZ, Streibig JC, Ritz C. 2007. Utilizing R software package for dose-response studies: the concept and data analysis. Weed Technol. 21:840–848. doi: 10.1614/WT-06-161.1
   Web of Science ®Google Scholar
• Lajide L, Escoubas P, Mizutani J. 1995. Termite antifeedant activity in Xylopia aethiopica. Phytochemistry. 40:1105–1112. doi: 10.1016/0031-9422(95)92653-P
   Web of Science ®Google Scholar
• Liu C, Xu Z, Chua NH. 1993. Auxin polar transport is essential for the establishment of bilateral symmetry during early plant embryogenesis. Plant Cell. 5:621–630. doi: 10.1105/tpc.5.6.621
   PubMed Web of Science ®Google Scholar
• López-Gresa MP, Torres C, Campos L, Lisón P, Rodrigo I, Bellés JM, Conejero V. 2011. Identification of defence metabolites in tomato plants infected by the bacterial pathogen Pseudomonas syringae. Environ Exp Bot. 74:216–228. doi: 10.1016/j.envexpbot.2011.06.003
   Web of Science ®Google Scholar
• MacDonald MJ, D’Cunha GB. 2007. A modern view of phenylalanine ammonia lyase. Biochem Cell Biol. 85:273–282. doi: 10.1139/O07-018
   PubMed Web of Science ®Google Scholar
• Macías FA, Marín D, Oliveros-Bastidas A, Chinchilla D, Simonet AM, Molinillo JMG. 2006. Isolation and synthesis of allelochemicals from gramineae: benzoxazinones and related compounds. J Agric Food Chem. 54:991–1000. doi: 10.1021/jf050896x
   PubMed Web of Science ®Google Scholar
• Macías FA, Molinillo JMG, Varela RM, Galindo JCG. 2007. Allelopathy – a natural alternative for weed control. Pest Manag Sci. 63:327–348. doi: 10.1002/ps.1342
   PubMed Web of Science ®Google Scholar
• Negrel J, Javelle F, Paynot M. 1993. Wound-induced tyramine hydroxycinnamoyl transferase in potato (Solanum tuberosum) tuber discs. J Plant Physiol. 142:518–524. doi: 10.1016/S0176-1617(11)80392-5
   Web of Science ®Google Scholar
• Newman M-A, von Roepenack-Lahaye E, Parr A, Daniels MJ, Dow JM. 2001. Induction of hydroxycinnamoyl-tyramine conjugates in pepper by Xanthomonas campestris, a plant defense response activated by hrp gene-dependent and hrp gene-independent mechanisms. Mol Plant Microbe Interact. 14:785–792. doi: 10.1094/MPMI.2001.14.6.785
   PubMed Web of Science ®Google Scholar
• Ni DA, Wang LJ, Xu ZH, Xia ZA. 1999. Foliar modifications induced by inhibition of polar transport of auxin. Cell Res. 9:27–35. doi: 10.1038/sj.cr.7290003
   PubMed Web of Science ®Google Scholar
• Nishida N, Tamotsu S, Nagata N, Saito C, Sakai A. 2005. Allelopathic effects of volatile Monoterpenoids produced by Salvia leucophylla: inhibition of cell proliferation and DNA synthesis in the root apical meristem of Brassica campestris seedlings. J Chem Ecol. 31:1187–1203. doi: 10.1007/s10886-005-4256-y
   PubMed Web of Science ®Google Scholar
• Park J-H, Fu Y-Y, Chung IS, Hahn T-R, Cho M-H. 2013. Cytotoxic property of ultraviolet-induced rice phytoalexins to human colon carcinoma HCT-116 cells. J Korean Soc Appl Biol Chem. 56:237–241. doi: 10.1007/s13765-012-3238-3
   Google Scholar
• Pitts RJ, Cernac A, Estelle M. 1998. Auxin and ethylene promote root hair elongation in Arabidopsis. Plant J. 16:553–560. doi: 10.1046/j.1365-313x.1998.00321.x
   PubMed Web of Science ®Google Scholar
• Rudrabhatla P, Reddy MM, Rajasekharan R. 2006. Genome-wide analysis and experimentation of plant serine/threonine/tyrosine-specific protein kinases. Plant Mol Biol. 60:293–319. doi: 10.1007/s11103-005-4109-7
   PubMed Web of Science ®Google Scholar
• Santos WDD, Ferrarese MDLL, Finger A, Teixeira ACN, Ferrarese-Filho O. 2004. Lignification and related enzymes in Glycine max root growth-inhibition by ferulic acid. J Chem Ecol. 30:1203–1212. doi: 10.1023/B:JOEC.0000030272.83794.f0
   PubMed Web of Science ®Google Scholar
• Sato T, Kiuchi F, Sankawa U. 1982. Inhibition of phenylalanine ammonia-lyase by cinnamic acid derivatives and related compounds. Phytochemistry. 21:845–850. doi: 10.1016/0031-9422(82)80077-0
   Web of Science ®Google Scholar
• Schraudner M, Langebartels C, Negrel JHS, Jr. 1993. Plant defense reactions induced in tobacco by the air pollutant ozone. In: Fritig B, Legrand M, editors. Mechanisms of plant defense responses. Volume 2 of the series developments in plant pathology. Springer; p. 286–290.
   Google Scholar
• Smeda RJ, Vaughn KC. 1994. Resistance to dinitroaniline herbicides. In: Powles SB, Holtum JAM, editors. Herbicide resistance in plants: biology and biochemistry. Boca Raton, FL: CRC Press; p. 215–228.
   Google Scholar
• Suzuki T, Usui I, Tomita-Yokotani K, Kono S, Tsubura H, Miki Y, Hasegawa K. 2001. Effects of acid extracts of tomato (Lycopersicon esculentum Mill.) and carrot (Daucus carota L.) wastes from the food industry on the growth of some crops and weeds. Weed Biol Manag. 1:226–230. doi: 10.1046/j.1445-6664.2001.00036.x
   Google Scholar
• Takikawa H. 2006. Synthetic studies on Breviones and structurally related natural products. Biosci Biotechnol Biochem. 70:1082–1088. doi: 10.1271/bbb.70.1082
   PubMed Web of Science ®Google Scholar
• Tefera T. 2002. Allelopathic effects of Parthenium hysterophorus extracts on seed germination and seedling growth of Eragrostis tef. J Agron Crop Sci. 188:306–310. doi: 10.1046/j.1439-037X.2002.00564.x
   Web of Science ®Google Scholar
• Thi HL, Lin C-H, Smeda RJ, Fritschi FB. 2014a. Isolation and purification of growth-inhibitors from Vietnamese rice cultivars. Weed Biol Manag. 14:221–231. doi: 10.1111/wbm.12050
   Web of Science ®Google Scholar
• Thi HL, Lin C-H, Smeda RJ, Leigh ND, Wycoff WG, Fritschi FB. 2014b. Isolation and identification of an allelopathic phenylethylamine in rice. Phytochemistry. 108:109–121. doi: 10.1016/j.phytochem.2014.08.019
   PubMed Web of Science ®Google Scholar
• Tregear JW, Jouannic S, Schwebel-Dugué N, Kreis M. 1996. An unusual protein kinase displaying characteristics of both the serine/threonine and tyrosine families is encoded by the Arabidopsis thaliana gene ATN1. Plant Sci. 117:107–119. doi: 10.1016/0168-9452(96)04400-7
   Web of Science ®Google Scholar
• Vishnoi S, Agrawal V, Kasana VK. 2009. Synthesis and structure–activity relationships of substituted cinnamic acids and amide analogues: a new class of herbicides. J Agric Food Chem. 57:3261–3265. doi: 10.1021/jf8034385
   PubMed Web of Science ®Google Scholar
• Vyvyan JR. 2002. Allelochemicals as leads for new herbicides and agrochemicals. Tetrahedron. 58:1631–1646. doi: 10.1016/S0040-4020(02)00052-2
   Web of Science ®Google Scholar
• Wolf RB, Spencer GF, Kwolek WF. 1984. Inhibition of velvetleaf (Abutilon theophrasti) germination and growth by benzyl isothiocyanate, a natural toxicant. Weed Sci. 32:612–615.
   Web of Science ®Google Scholar
• Wu Z, Zheng L, Li Y, Su F, Yue X, Tang W, Ma X, Nie J, Li H. 2012. Synthesis and structure–activity relationships and effects of phenylpropanoid amides of octopamine and dopamine on tyrosinase inhibition and antioxidation. Food Chem. 134:1128–1131. doi: 10.1016/j.foodchem.2012.02.152
   PubMed Web of Science ®Google Scholar
• Yang GZ, Zhao S, Li YC. 2002. Studies on the chemical constituents of Lycianthes biflora. Yao Xue Xue Bao. 37:437–439.
   PubMedGoogle Scholar
• Yang Y, Song ZG, Liu ZQ. 2011. Synthesis and antioxidant capacities of hydroxyl derivatives of cinnamoylphenethylamine in protecting DNA and scavenging radicals. Free Radic Res. 45(4):445–453. doi: 10.3109/10715762.2010.540576
   PubMed Web of Science ®Google Scholar