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Curcumin Synthesis in Curcuma longa: Two Cooperating Enzymes
16/03/11 12:23 PM
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Curcumin Biosynthesis in Curcuma longa
Key references Katsuyama, Y., Kita, T., Funa, N., Horinouchi, S., 2009a. Curcuminoid biosynthesis by two type III polyketide synthases in the herb Curcuma longa. Journal of Biological Chemistry 284, 11160-11170. And quite new: Katsuyma,Y., Kita, T., Horinouchi, S., 2009b. Identification and characterization of multiple curcumin synthases from the herb Curcuma longa. FEBS Letters, 583, 2799-2783. In the context of this work you should also look at the 'Curcuminoid synthase' from rice, and on the application of the two-component system to phenylphenalenone biosynthesis: more...
Curcuminoids are apparently exclusively found in the rhizomes of Curcuma longa (more...), and the predominant compound is curcumin (Fig. 1). Powdered turmeric rhizome is widely used a food additive and in Asian medicine; it is believed to have many beneficial effects on all sorts of ailments, see for recent discussions: Corson and Crews, 2007; Aggarwal et al., 2007, Anand et al., 2008; Srivastava and Mehta, 2009. Fig. 1. Major curcuminoids in Curcuma longa. Typical distributions in powdered turmeric are: Curcumin 2%, Demethoxycurcumin 0,7%, Bisdemethoxycurcumin 0,6% (Hiserodt et al., 1996).
Precursor-feeding studies suggested very early that the backbone consists of two phenylpropanoids (ferulate in the case of curcumin) which are connected by an acetate derived carbon unit. The same basic setup is found in many other substances, e.g. the phenylphenalenones (like anigorufone), and in the gingerols (one phenylpropanoid + a short chain fatty acid), and proposals for the biosynthetic reactions were discussed intensively (see for example the review in: Cooke and Edwards, 1980). The early precursor feeding studies for curcumin were apparently not conclusive; they could not clearly distinguish between two possibilities: a) starter phenylpropanoid-CoA, five extensions with malonyl-CoA, then ring-closure and further modifications, and b) biosynthesis from two phenylpropanoid-CoA and one malonyl-CoA (Roughly and Whiting, 1971; 1973). Much later (Schröder, 1997) I proposed that the biosynthesis of all of these natural products might start with a type III PKS reaction corresponding to the single condensation carried out by benzalacetone synthase, and that the resulting diketide is the basis for the synthesis of the final structures. At that time I was not aware of the finding that the biosynthesis was not that clear in the case of curcumin. Actually it was only recently that curcumin biosynthesis could be demonstrated in vitro in crude extracts of Curcuma longa. The activity was not purified, and thus it remained open whether one or several enzymes were involved (Ramirez-Ahumada et al., 2006).
Interesting new findings
It was quite important to see in a recent publication that curcumin biosynthesis could now be elucidated with enzymes from Curcuma longa (Katsuyama et al., 2009a), i.e. the plant that actually does synthesize curcuminoids. The findings are described here in a brief summary. The biosynthesis requires two cooperating enzymes; both are type III PKS, they share 62% identity. One of them corresponds to a previous entry in an EST-library, the other was obtained with degenerate primers/PCR. Both were expressed as recombinant proteins in E. coli. Figure 2 summarizes the reactions. Fig. 2. Model for the biosynthesis of curcumin. For comparison, have a look at the Curcuminoid synthase from rice.
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These latter two are about 95% identical. i.. the results indicate that curcumin in Curcumal longa is synthesized by the cooperation of two different type III PKS. longa uses two enzymes.5. Return to top A generalization of the 'two enzyme principle' ? There are other natural products that possibly share the same basic biosynthetic reactions. but two more sequences: AY739910 (= Wdf2) and AY973271 (= Wdf3).1. the phenylphenalenones in Wachendorfia thyrsiflora. but 4-coumaroyl-CoA and feruloyl-CoA gave trace amounts of curcuminoids. most importantly. CURS2 and CURS3 (the first CURS was renamed to CURS1). the most interesting experiment was the co-incubation of DCS and CURS.. However. as suggested for the unusual enzyme from rice (more. Both DCS and CURS use feruloyl-CoA as starter substrate. the best substrate. Incubations of CURS with starter substrates and the cinnamoyl-diketide-NAC in fact led to curcuminoid formation. extraction with organic solvent and subsequent analysis. That is quite interesting in several points: It shows that C.. see the relationship tree. but also the starter substrate for the next condensation in all type III PKS reactions carrying out more than one condensation. indeed. they might compete for the same substrate..e. If the findings with C. The decisive point to detect the enzyme activity: do the analysis directly from the incubation. Nevertheless. The CURS reaction raises an interesting question: which is in this case the starter. and. which is the extender? That is not quite trivial because it is not necessarily 4-coumaroyl-CoA. Both were closely related to each other and CURS1. Brand et al. in assays simply containing feruloyl-CoA and malonyl-CoA.Curcumin Synthesis in Curcuma longa: Two Cooperating Enzymes 16/03/11 12:23 PM The enzymes 1. indicating that the enzyme in fact carried out only one condensation with malonyl-CoA. longa can be generalized: In W. and most important in this context. WtPKS1.html Page 2 of 5 .. 2.de/data/bio2/schroeder/Curcumin_Biosynthesis. CURS. but the values are much lower with WtPKS1 (about 55-60% identity)... and therefore the authors synthesized a NAC (N-acetylcysteamine) derivative for cinnamoyl-diketide (certainly not the optimal choice. Of course. but the databases actually do not only contain the characterized DCS candidate (AY727928.biologie. Return to top Update on new CURS-type enzymes A recent publication (Katsuyama et al. but the synthesis was the simplest feasible option).1. i... like gingerol (Ginger).01. it could also be the diketide CoA: this is of course not only the product of the first condensation.) that has no known physiological function. 4-coumaroyl-CoA.. they revealed interesting differences in the substrate preferences.e. The results with DCS suggested that diketidyl-CoAs could be the 'real' substrates. the statement that CURS synthesized a curcuminoid with a combination of feruloyl-CoA and the cinnamate diketide acid strongly suggests that the diketide is the chain extender: I am not aware of any type III PKS that can use a diketide acid as starter substrate (instead of an CoA. rather than a single enzyme using two different chain extenders. suggesting that the modifications leading from 4-coumarate to ferulate residues was done on the phenylpropanoid level. that it released the diketide CoA-ester rather than a diketide acid (which is likely to be decarboxylated non-enzymatically to the ketone). Taken together.uni-freiburg. The reaction was very efficient with feruloyl-CoA. Interestingly. However. called Wdf1).e. the kinetics of the enzyme with feruloyl-CoA suggested that the substrate was an allosteric regulator of the activity. suggesting that the enzyme carried out only one condensation. 2009b) described the molecular and functional characterization of two more CURS-type enzymes. 4-Coumaroyl-CoA led at least to a detectable low production of benzalacetone... It therefore makes sense that feruloyl-CoA is an allosteric regulator of DCS: there would be no point in its using up all the feruloyl-CoA that is needed for the subsequent CURS reaction in a metabolic flow situation. a point that could be important for the cooperation with the subsequent enzyme. DCS ( Diketide-CoA Synthase): That enzyme showed very little or no activity with cinnamoyl-CoA.. not at the level of the curcuminoids. The experiment revealed an efficient production of curcumin. i. or feruloyl-CoA.or NAC-activated molecule). No activity at all was found with cinnamoyl-CoA. do not use acidification or extraction with ethylacetate. and a candidate enzyme for the first reaction ('DCS' function) has been described (more. When the analysis was done directly with the incubation mixture: it turned out that the CoA-esters had been converted to the diketidyl-CoAs. if the products were analyzed with the standard procedures. 2006)... CURS (Curcumin Synthase): Incubations of that enzyme with cinnamoyl-CoA led to no products. Could this be candidates for a CURS function? This is proposed in the discussion http://www. thyrsiflora a protein with the 'CURS' function had not been identified..0. each carrying out only one condensation. a very satisfying result. and this may indeed taken as suggestion that the composition of the curcuminoids in different cultivars may be influenced by the rate of expression of the different enzymes.
. named diketide-CoA synthase (DCS). With all other substrates.Curcumin Synthesis in Curcuma longa: Two Cooperating Enzymes 16/03/11 12:23 PM of the Katsuyama et al. curcumin and polycyclic phenylphenalenones).. Proposals . Planta 224.does not really belong here: it is actually one enzyme with two condensations: more.uni-freiburg..Quinoline alkaloids: more. although CURS itself possessed low activity for the synthesis of curcumin from feruloyl-CoA and malonyl-CoA.... Funa. Journal of Biological Chemistry 284. Root cultures from Wachendorfia thyrsiflora (Haemodoraceae) are a suitable source to search for such enzymes because they synthesize large amounts of phenylphenalenones.. activity was also not detected in incubations with diketide-NAC derivatives. or in assays containing the expected substrates and both Wdf1 and Wdf2. Return to top Links to other enzymes with one condensation reaction Benzalacetone Synthases .. Svatos.. In vitro analysis revealed that CURS2 preferred feruloyl-CoA as a starter substrate and CURS3 preferred both feruloyl-CoA and p-coumaroyl-CoA..Curcuminoid synthase in rice: .. Identification and characterization of multiple curcumin synthases from the herb Curcuma longa. that are capable of curcuminoid synthesis were identified and characterized. J. were observed only with unsaturated phenylpropanoid-CoAs. thyrsiflora polyketide synthase 1). We propose that WtPKS1 catalyses the first step in diarylheptanoid biosynthesis and that the observed pyrones are derailment products in the absence of downstream processing proteins. T. . Here we propose a pathway for curcuminoid biosynthesis in the herb C. S.0. Curcuminoids are pharmaceutically important compounds isolated from the herb Curcuma longa. the experiments with Wdf2 and Wdf3 from Wachendorfia thyrsiflora so far do not provide any results suggesting that one or both of these proteins might correspond to the CURS functions identified in the C. no enzyme systems have been elucidated. Return to top or to text Katsuyama. Horinouchi. One of the type III PKSs. S. It was soluble and could easily be purified. 2005): Wdf2: a recombinant protein was expressed in E.de/data/bio2/schroeder/Curcumin_Biosynthesis. It was named WtPKS1 (W. Schröder.. but no other products that are known to require CHSs or related enzymes (e. and CURS then converts the diketide-CoA esters into a curcuminoid scaffold. Pflanzliche Polyketidsynthasen des Typ III in Wachendorfia thyrsiflora (Haemodoraceae). A. catalyzed the in vitro formation of curcuminoids from cinnamoyl-diketide-N-acetylcysteamine (a mimic of the CoA ester) and feruloylCoA. Wdf3: the recombinant protein was difficult to purify because it was poorly soluble.g. and the best results were obtained with 4-coumaroyl-CoA (80% of the products). but the published PhD thesis of Silke Brand (Brand... have a look at a recent relationship tree (click here for a PDF-file of the tree): The tree suggests that WtPKS1 forms a subgroup with the diketide-CoA synthase (DKS) from Curcuma longa. . Schierhorn. T. 2005...5... References Katsuyama. Curcuminoids found in the rhizome of turmeric. Y. N. Friedrich-Schiller-Universität http://www. 2009b. Return to top . Nevertheless. 11160-11170. which includes two novel type III polyketide synthases (PKSs). including phenylpropionyl. named curcumin synthase (CURS). Co-incubation of DCS and CURS in the presence of feruloyl-CoA and malonyl-CoA yielded curcumin at high efficiency. (2009) publication. In particular these latter negative results would not be expected for a CURS function. The availability of the substrates and the expression levels of the three different enzymes capable of curcuminoid synthesis with different substrate specificities might influence the composition of curcuminoids in the turmeric and in different cultivars. in German) does contain additional information that of course was not easily accessible to the Japanese group. longa system.. Curcuma longa. bisdemethoxycurcumin and demethoxycurcumin. These findings thus revealed the curcumin biosynthetic route in turmeric.Rhubarb (Rheum palmatum): more. These results suggested that CURS2 synthesizes curcumin or demethoxycurcumin and CURS3 synthesizes curcumin. Enzyme assays with all sorts of candidates failed. 2006. FEBS Letters 583. 413-428.1. Most importantly.1. D. the activities could be tested..Phenylphenalenones: more.. B. catalyzed the formation of feruloyl-diketide-CoA by condensing feruloyl-CoA and malonyl-CoA. The other.Raspberry (Rubus idaeus): more. A.. However. Taken together. Hölscher. No activity was found with aromatic starter CoA-esters. coli. These results do not provide any clues for a role in phenylphenalenone biosynthesis. named CURS2 and CURS3.. (2006) paper does not provide information on the two other proteins.. The purified recombinant protein accepted a large variety of aromatic and aliphatic starter CoA esters. Return to text Brand.and side-chain unsaturated phenylpropanoid-CoAs. Kita. The simplest model for the initial reaction in diarylheptanoid biosynthesis predicts a phenylpropanoid-CoA as starter and a single condensation reaction to a diketide.01. WtPKS1 performed two condensation reactions and released pyrones. Return to text or go to a more detailed discussion Request a reprint Brand.Curcuminoids: . Diketide Derivatives . 2005...g..html Page 3 of 5 . A type III polyketide synthase from Wachendorfia thyrsiflora and its role in diarylheptanoid and phenylphenalenone biosynthesis. Curcuminoid biosynthesis by two type III polyketide synthases in the herb Curcuma longa. Kita. C-Methylated Flavonoids: more.. and that WtPKS2 and WtPKS3 group with the curcumin synthase (CURS) from Curcuma longa: it is tempting to speculate that the 'two enzyme principle' discussed here might actually apply to the first reactions in phenylphenalenone biosynthesis. Schneider. . The results in brief (Brand. S. (Note: this is different from benzalacetone !!) .biologie.. no activity could be detected with any of the substrates. 2009a. Chalcone synthase (CHS) related type III plant polyketide synthases (PKSs) are likely to be involved in the biosynthesis of diarylheptanoids (e. and the products were the results expected from one or/and two condensations. Horinouchi. A homology-based RT-PCR strategy led to the identification of cDNAs for a type III PKS sharing only approximately 60% identity with typical CHSs.. The Brand et al. in which DCS synthesizes feruloyl-diketide-CoA. flavonoids or stilbenes). S.. longa... possess various biological activities.Benzylacetone: more.. 2799-2783. but no such activity has been reported. Despite much attention regarding the biosynthesis of curcuminoids because of their pharmaceutically important properties and biosynthetically intriguing structures. Y. Benzalacetones...Curcuminoid biosynthesis by two cooperating enzymes in Curcuma longa: more... the expected release products. in particular since one would postulate an activity with aromatic CoA-esters. There was activity with linear aliphatic CoA-esters (C3 to C8 CoA-esters). PhD Thesis.. Two additional type III polyketide synthases.
R. Chemistry & Biology 14.g. wounds. and targeted therapies.. was first isolated almost two centuries ago. 2007. caffeic acid O- http://www. a derivative of turmeric used for centuries to treat a wide variety of inflammatory conditions. 2007. T. Traditional medicines provide fertile ground for modern drug development.html Page 4 of 5 . Edwards. Three enzymes were analyzed and investigated with regard to their involvement in the biosynthesis. We have developed a system for producing "unnatural" flavonoids and stilbenes in Escherichia coli. EGFR. C. M. is a gold-colored spice commonly used in the Indian subcontinent. p38 mitogen activated protein kinase and signal transducer and activator of transcription-3. in turmeric these are the curcuminoids. No Abstract available. B. proliferation (HER-2. N. Curcumin. triptolide. AVASTIN). Return to text Corson.. Assays for enzymes in the phenylpropanoid pathway identified the corresponding enzyme activities in protein crude extracts from leaf.. A host of studies in in vitro and in vivo models of cardiac injury show that curcumin treatment reduces reactive oxygen species generation.. head and neck squamous cell carcinoma. Recent studies in models of pressure overload show that curcumin can reduce cardiac remodeling by altering reninangiotensin-system-transforming growth factor 1 and collagen axis.. pains. Journal of Cardiovascular Pharmacology and Therapeutics 14. R. Type III polyketide synthases should be involved in the first steps of the biosynthesis.. COX-2. p-coumaroyl shikimate transferase. invasion (MMP-9 and adhesion molecules). antiviral. ERLOTINIB. as well as three other major components and numerous minor components.. Molecular understanding and modern application of traditional medicines: triumphs and trials. Aggarwal. While plant-based formulations have been used to treat cancer for centuries. current treatments usually involve poisonous mustard gas.. Wachendorfia thyrsiflora (Haemodoraceae) contains a group of secondary metabolites called phenylphenalenones. curcumin can be considered an ideal "Spice for Life".. Alzheimer's disease. 2006. P. These included a substrate synthesis step for CoA esters synthesis from carboxylic acids by 4-coumarate:CoA ligase. IL-6. T. Fortschritte der Chemie organischer Naturstoffe 40. and gastrointestinal systems. Studies need to be done in humans to define the potential of curcumin in limitation of cardiac injury and preservation of cardiac function following ischemia. breast cancer. Considering the recent scientific bandwagon that multitargeted therapy is better than monotargeted therapy for most diseases. Y.. Ichikawa. including those of the skin. apoptosis (activation of caspases and down-regulation of antiapoptotic gene products). turmeric (popularly called "curry powder") that has been shown to interfere with multiple cell signaling pathways.. Fürstengraben 26. Flavonoids and stilbenes have attracted much attention as potential targets for nutraceuticals. 2017-2029. S. The activity of curcumin reported against leukemia and lymphoma. pulmonary. H. 2007b. the formation of linear diarylheptanoids. aches. what are the active principles in them and how do they mediate their effects against cancer is perhaps best illustrated by curcumin.biologie. HUMIRA... These effects are mediated through the regulation of various transcription factors. shoot and rhizome tissues from ginger and turmeric... not only for health care but also for the preservation of food and as a yellow dye for textiles.. Mehta. and subsequent downstream signals.01. Cancer is primarily a disease of old age. Curcumin has been shown to exhibit antioxidant. Horinouchi. arthritis. Currying the heart: curcumin and cardioprotection. Hartman. and anticancer activities and thus has a potential against various malignant diseases. M. and a HER2 blocker (e.1. Cancer Letters 267. Germany. Biosynthesis of curcuminoids and gingerols in turmeric (Curcuma longa) and ginger (Zingiber officinale): identification of curcuminoid synthase and hydroxycinnamoyl-CoA thioesterases. Members of the Zingiberaceae such as turmeric (Curcuma longa L. antifungal.. and other chronic illnesses. neurological cancers.0. metastasis (CXCR-4) and inflammation (NF-?B.g. monocyte adhesion to activated endothelial cells. Jhurani. R. B. Since the time of Ayurveda (1900 Bc) numerous therapeutic activities have been assigned to turmeric for a wide variety of diseases and conditions. Curcumin is a diferuloylmethane derived from the Indian spice.Curcumin Synthesis in Curcuma longa: Two Cooperating Enzymes 16/03/11 12:23 PM Jena. M.) and ginger (Zingiber officinale Rosc. S. Incubation of the recombinant E. Thermospray mass spectra were obtained for all of the components. Crews. Return to text Aggarwal. B. flavanone 3beta-hydroxylase and flavonol synthase. This system is promising for construction of a larger library by employing other polyketide synthases and modification enzymes. we highlight the challenges along this route. Return Srivastava. 1996. Sundaram. Particle beam EI-mass spectra were obtained for the curcuminoids. allergies.g. and mechanistic studies before eventual deployment in the clinic. A.. Thus an "old-age" disease such as cancer requires an "age-old" treatment. Ho.. Naturally occurring phenalenones and related compounds. isolation. Funa.. Curcumin exhibits activities similar to recently discovered tumor necrosis factor blockers (e. chemotherapy. diabetes. celastrol. Here. ovarian cancer. The artificial biosynthetic pathway included three steps. which gives the yellow color to turmeric. and ENBREL). are due to curcumin. 1980. human epidermal growth factor receptor blockers (e. REMICADE. anti-inflammatory..) accumulate at high levels in their rhizomes important pharmacologically active metabolites that appear to be derived from the phenylpropanoid pathway. EI mass spectra for the volatile components were obtained by direct thermal desorption-gas chromatography-mass spectrometry (DTD-GC-MS). C. demethoxycurcumin and bisdemethoxycurcumin. but first they must pass along a pathway of discovery. and sarcoma reflects its ability to affect multiple targets. Malani.. ERBITUX. R. that are probably involved in the defense against pathogens. once associated with turmeric. capsaicin. little is known about the biosynthesis of these compounds. Characterization of powdered turmeric by liquid chromatography-mass spectrometry and gas chromatography-mass spectrometry. Cell 130. Phytochemistry 67. G.. and 5-LOX). Return to text Hiserodt. 133-164. This work deals with the isolation of polyketide synthases from root cultures of Wachendorfia thyrsiflora and their characterization. growth factors. Despite their importance.uni-freiburg. These alterations lead to preservation of myocardial function following ischemic or biochemical insult to the heart. Curcumin: the Indian solid gold. Extensive research within the last half century has proven that most of these activities. 22-27.. and phosphorylation of c-Jun N-terminal kinase. While traditional plant-derived medicines are safe. Rosen. 07743 Jena. and AP-1). survival (PI3K/AKT pathway). W. and its cardiovascular effects. protein kinases. Gang. and liver disorders. C. G. and its structure as diferuloylmethane was determined in 1910. p-coumaroyl quinate transferase... Synthesis of unnatural flavonoids and stilbenes by exploiting the plant biosynthetic pathway in Escherichia coli. N. Turmeric. but could not be obtained for the other components due to the limitations of the particle beam interface when analyzing volatile and semi-volatile compounds.de/data/bio2/schroeder/Curcumin_Biosynthesis. antibacterial. Miyahisa. and a modification step for modification of the flavanones by flavone synthase. gastrointestinal cancers. Return Cooke. focusing on the compounds artemisinin.. Journal of Chromatography A 740. 769-774. derived from the plant Curcuma longa. B... and GEFTINIB). IL-1. C. These enzymes included phenylalanine ammonia lyase. 51-63. This work contains in addition to the characterization of the proteins by enzyme assays also hints to the nature of a second involved enzyme. a polyketide synthesis step for conversion of the CoA esters into flavanones by chalcone synthase and chalcone isomerase.. Biologisch-Pharmazeutische Fakultät. J. G. melanoma. angiogenesis (VEGF). Sundaram. inflammatory cytokines. In ginger. T. I. and pharmaceuticals. This investigation describes the identification of enzymes in the biosynthetic pathway leading to the production of these bioactive natural products. T.. B.. including cell cycle (cyclin D1 and cyclin E). Curcumin (diferuoylmethane) is the active ingredient of turmeric (Curcuma longa). a vascular endothelial cell growth factor blocker (e.. but itself not able to form diarylheptanoids. One of the enzymes is probably involved in the biosynthesis. these compounds are the gingerols. 2009. radiation.1. B. J. coli with exogenously supplied carboxylic acids led to production of 87 polyketides. The separation was accomplished on an octadecyl stationary phase using a mobile phase consisting of 50 mM ammonium acetate with 5% acetic acid and acetonitrile as the organic modifier.. and into stilbenes by stilbene synthase. cosmetics. genitourinary cancers.. Return to text Ramirez-Ahumada. The developed HPLC method allows the separation of curcumin. Curcumin and cancer: An "old-age" disease with an "age-old" solution.. Five commercial powdered turmeric samples were analyzed to identify major and minor components.. D.g. N. and that life style plays a major role in the development of most cancers is now well recognized. Kunnumakkara. 1-75. 153-190. 2008. Return Anand. including 36 unnatural flavonoids and stilbenes. polyketide synthases. Advances in Experimental Medicine and Biology 595. TNF.. sprains. and other enzymes. There has been a surge of research in its anti-inflammatory and antioxidative properties. Return to text Katsuyama. 613-621.. Timmermann. L. and curcumin.5. lung cancer. HERCEPTIN). C.
Curcumin Synthesis in Curcuma longa: Two Cooperating Enzymes 16/03/11 12:23 PM methyltransferase. Perkin Transactions 1.05. in which two cinnamate units condense with one malonate unit. D.14 C]phenylalanine were incorporated into curcumin without scrambling of the label. Other interpretations are discussed.03.. 1973. and the fractional distribution of label along the heptane chain was determined. All crude extracts possessed activity for all of these enzymes. A. [1and 2.5dione]. A family of plant-specific polyketide synthases: facts and predictions. Experiments in the biosynthesis of curcumin. The first two cinnamic acids are incorporated into curcumin significantly better than the last.04.0. especially in ginger tissues. Return to text Return to top File History : 21. 23792388.. http://www. and acridones are closely related plant-specific polyketide synthases. suggesting that the protein family is much older than previously assumed. P. D. Diarylheptanoids. and supplied to C. the results do not provide satisfactory support for the expected biosynthetic scheme.2009: Publication update: Identification of two more CURS-type enzymes in Curcuma longa: Katsuyama et al.. Ionga. are reported..1.2009: Update on reference 05.14 C]-Acetate and -malonate were also incorporated. No Abstract available. A. Ionga with [14 C]phenylalanine. thereby potentially playing a regulatory role in the biosynthesis of these compounds.and 3. Whiting.4-dihydroxy-cinnamic acids were prepared.biologie. In administration of labelled precursors to C.2009: Link to application of two-component system to phenylphenalenone biosynthesis 30.. Recent results suggest that they belong to a family of condensing enzymes that catalyze the initial key reactions in the biosynthesis of several biologically and pharmaceutically interesting substances. with the exception of polyketide synthases. The biogenesis of natural diarylheptanoids is discussed. 1971.. Trends in Plant Science 2..04.. This result was explained by the identification of thioesterase activities that cleaved phenylpropanoid pathway CoA esters. which were evaluated because of their potential roles in controlling production of certain classes of gingerols and curcuminoids.html Page 5 of 5 ..5. Tetrahedron Letters 40.6-diene-3. Journal of the Chemical Society..7-bis-(4-hydroxy-3-methoxyphenyl)hepta-1. 3741-3745.2009: Design of page . and -3. Recent analysis has revealed that related sequences occur in bacteria. J.. The product range is even more extended by modification of reaction intermediates. Return to text Roughly. [1. Return to text Roughley. -4-hydroxy-.1.. J. and which were found to be present at high levels in all tissues. The results of polyketide synthase assays showed detectable curcuminoid synthase activity in the extracts from turmeric with the highest activity found in extracts from leaves.08. The enzymes synthesizing chalcones. Return to text Schröder. stilbenes. the pigment of Curcuma Ionga rhizome. no gingerol synthase activity could be identified. and caffeoyl-CoA O-methyltransferase. with particular reference to curcumin [1.de/data/bio2/schroeder/Curcumin_Biosynthesis. (2009b). These activities may shunt phenylpropanoid pathway intermediates away from the production of curcuminoids and gingerols. Whiting. However. Methods for the isolation. 373-378. 1997. suitable for biosynthetic work. J... characterisation. and degradation of curcumin. P.01. although none was utilised quite as efficiently as phenylalanine.2009: Link to new relationship tree: click here for a PDF-file 24. [ 3 H]-4-Hydroxy-3-methoxy-. the problems of the biosynthesis.uni-freiburg. 05.
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