Biosynthesis of curcuminoids and gingerols in turmeric (Curcuma longa) and ginger (Zingiber officinale): Identification of curcuminoid synthase and hydroxycinnamoyl-CoA thioesterases

Phytochemistry - Tập 67 - Trang 2017-2029 - 2006
Maria del Carmen Ramirez-Ahumada1, Barbara N. Timmermann1, David R. Gang1,2
1Arizona Center for Phytomedicine Research and Department of Pharmacology and Toxicology, University of Arizona, Tucson, AZ 85721-0036, USA
2Department of Plant Sciences and Bio5 Institute, University of Arizona, 303 Forbes Building, Tucson, AZ 85721-0036, USA

Tài liệu tham khảo

Austin, 2003, The chalcone synthase superfamily of type III polyketide synthases, Nat. Prod. Rep., 20, 79, 10.1039/b100917f Austin, 2004, Crystal structure of a bacterial type III polyketide synthase and enzymatic control of reactive polyketide intermediates, J. Biol. Chem., 279, 45162, 10.1074/jbc.M406567200 Baranowski, 1986, Changes in solids, oleoresin, and (6)-gingerol content of ginger during growth in Hawaii, Hortscience, 21, 145, 10.21273/HORTSCI.21.1.145 Beuerle, 2002, Enzymatic synthesis and purification of aromatic coenzyme A esters, Anal. Biochem., 302, 305, 10.1006/abio.2001.5574 Bradford, 1976, Rapid and sensitive method for quantitation of microgram quantities of protein utilizing principle of protein–dye binding, Anal. Biochem., 72, 248, 10.1016/0003-2697(76)90527-3 Brand, 2006, A type III polyketide synthase from Wachendorfia thyrsiflora and its role in diarylheptanoid and phenylphenalenone biosynthesis, Planta, 224, 413, 10.1007/s00425-006-0228-x Claeson, 1994, Naturally occurring 1,7-diarylheptanoids, J. Indian Chem. Soc., 71, 509 Costa, 2003, An in silico assessment of gene function and organization of the phenylpropanoid pathway metabolic networks in Arabidopsis thaliana and limitations thereof, Phytochemistry, 64, 1097, 10.1016/S0031-9422(03)00517-X Denniff, 1976, Biosynthesis of [6]-gingerol, pungent principle of Zingiber officinale, J. Chem. Soc. Chem. Commun., 711, 10.1039/c39760000711 Denniff, 1980, Studies in the biosynthesis of [6]-gingerol, pungent principle of ginger (Zingiber officinale), J. Chem. Soc., Perkin Trans. 1, 2637, 10.1039/p19800002637 Gang, 2005, Evolution of flavors and scents, Annu. Rev. Plant Biol., 56, 301, 10.1146/annurev.arplant.56.032604.144128 Gang, 2001, An investigation of the storage and biosynthesis of phenylpropenes in sweet basil, Plant Physiol., 125, 539, 10.1104/pp.125.2.539 Gang, 2002, Differential production of meta hydroxylated phenylpropanoids in sweet basil (Ocimum basilicum L.) peltate glandular trichomes and leaves is controlled by the activities of specific acyltransferases and hydroxylases, Plant Physiol., 130, 1536, 10.1104/pp.007146 Gomez-Vasquez, 2004, Phenylpropanoids, phenylalanine ammonia lyase and peroxidases in elicitor-challenged cassava (Manihot esculenta) suspension cells and leaves, Ann. Bot., 94, 87, 10.1093/aob/mch107 Gowri, 1991, Stress responses in alfalfa (Medicago sativa L.). 12. Sequence-analysis of phenylalanine ammonia-lyase (PAL) cDNA clones and appearance of PAL transcripts in elicitor-treated cell-cultures and developing plants, Plant Mol. Biol., 17, 415, 10.1007/BF00040636 Hoffmann, 2003, Purification, cloning, and properties of an acyltransferase controlling shikimate and quinate ester intermediates in phenylpropanoid metabolism, J. Biol. Chem., 278, 95, 10.1074/jbc.M209362200 Hoffmann, 2004, Silencing of hydroxycinnamoyl-coenzyme A shikimate/quinate hydroxycinnamoyl transferase affects phenylpropanoid biosynthesis, Plant Cell, 16, 1446, 10.1105/tpc.020297 Jez, 2000, Structural control of polyketide formation in plant-specific polyketide synthases, Chem. Biol., 7, 919, 10.1016/S1074-5521(00)00041-7 Jez, 2001, Structure and mechanism of chalcone synthase-like polyketide synthases, J. Ind. Microbiol. Biotechnol., 27, 393, 10.1038/sj.jim.7000188 Jiang, 2005, Characterization of gingerol-related compounds in ginger rhizome (Zingiber officinale Rosc.) by high-performance liquid chromatography/electrospray ionization mass spectrometry, Rapid Commun. Mass Spectrom., 19, 2957, 10.1002/rcm.2140 Jiang, 2005, Metabolic profiling, phylogenetic analysis and anti-inflammatory investigation of Zingiber species: tools for authentication of ginger (Zingiber officinale Rosc.), Phytochemistry, 67, 232 Jiang, 2006, Analysis of curcuminoids by positive and negative electrospray ionization and tandem mass spectrometry, Rapid Commun. Mass Spectrom., 20, 1001, 10.1002/rcm.2401 Jiang, 2006, Use of liquid chromatography–electrospray ionization tandem mass spectrometry to identify diarylheptanoids in turmeric (Curcuma longa L.) rhizome, J. Chromatogr. A, 1111, 21, 10.1016/j.chroma.2006.01.103 Joe, 2004, Biological properties of curcumin-cellular and molecular mechanisms of action, Crit. Rev. Food Sci. Nutri., 44, 97, 10.1080/10408690490424702 Koeduka, 2006, Eugenol and isoeugenol, characteristic aromatic constituents of spices, are biosynthesized via reduction of coniferyl alcohol esters, Proc. Natl. Acad. Sci. USA, 103, 10128, 10.1073/pnas.0603732103 Lofty, 1992, Partial purification and characterization of hydroxycinnamoyl CoA:transferases from apple and date fruits, Phytochemistry, 31, 767, 10.1016/0031-9422(92)80156-9 Macleod, 1979, Stages in the biosynthesis of [6]-gingerol in Zingiber officinale, J. Chem. Soc., Chem. Commun., 1152, 10.1039/c39790001152 Mascolo, 1989, Ethnopharmacological investigation of ginger (Zingiber officinale), J. Ethnopharmacol., 27, 129, 10.1016/0378-8741(89)90085-8 Miquel, 2002, The curcuma antioxidants: pharmacological effects and prospects for future clinical use. A review, Arch. Gerontol. Geriat., 34, 37, 10.1016/S0167-4943(01)00194-7 Mustafa, 1993, Drug development report. 9. Pharmacology of ginger, Zingiber officinale, J. Drug Dev., 6, 25 Negrel, 1984, The phosphohydrolysis of hydroxycinnamoyl-coenzyme A thioesters in plant extracts, Phytochemistry, 23, 31, 10.1016/0031-9422(84)83072-1 Noel, 2005, Structure–function relationships in plant phenylpropanoid biosynthesis, Curr. Opin. Plant Biol., 8, 249, 10.1016/j.pbi.2005.03.013 Nugroho, 2002, Activities of enzymes involved in the phenylpropanoid pathway in constitutively salicylic acid-producing tobacco plants, Plant Physiol. Biochem., 40, 755, 10.1016/S0981-9428(02)01437-7 Petersen, 1993, Purification of rosmarinic acid synthase from cell-cultures of Coleus blumei Benth, Planta, 191, 18, 10.1007/BF00240891 Rababah, 2004, Total phenolics and antioxidant activities of fenugreek, green tea, black tea, grape seed, ginger, rosemary, gotu kola, and ginkgo extracts, vitamin E, and tert-butylhydroquinone, J. Agric. Food Chem., 52, 5183, 10.1021/jf049645z Schröder, 1997, A family of plant-specific polyketide synthases: facts and predictions, Trends Plant Sci., 2, 373, 10.1016/S1360-1385(97)87121-X Sharan, 1998, Effects of methyl jasmonate and elicitor on the activation of phenylalanine ammonia-lyase and the accumulation of scopoletin and scopolin in tobacco cell cultures, Plant Sci., 132, 13, 10.1016/S0168-9452(97)00260-4 Ulbrich, 1979, Partial purification and properties of p-hydroxycinnamoyl-CoA:quinate hydroxycinnamoyl transferase from higher plants, Phytochemistry, 18, 929, 10.1016/S0031-9422(00)91451-1 Ulbrich, 1980, Partial purification and properties of p-hydroxycinnamoyl-CoA:shikimate-p-hydroxycinnamoyl transferase from higher plants, Phytochemistry, 19, 1625, 10.1016/S0031-9422(00)83782-6 Vassão, 2006, Chavicol formation in sweet basil (Ocimum basilicum): cleavage of an esterified C9 hydroxyl group with NAD(P)H-dependent reduction, Org. Biomol. Chem., 4, 2733, 10.1039/B605407B