30802-02-9Relevant articles and documents
Coenzyme A-Conjugated Cinnamic Acids – Enzymatic Synthesis of a CoA-Ester Library and Application in Biocatalytic Cascades to Vanillin Derivatives
Dippe, Martin,Bauer, Anne-Katrin,Porzel, Andrea,Funke, Evelyn,Müller, Anna O.,Schmidt, Jürgen,Beier, Maria,Wessjohann, Ludger A.
supporting information, p. 5346 - 5350 (2019/11/29)
We present a bioorthogonal method for the ligation of coenzyme A (CoA) with cinnamic acids. The reaction, which is the initial step in the biosynthesis of a multitude of bioactive secondary metabolites, is catalyzed by a promiscuous plant ligase and yields CoA conjugates with different functionalization in high purity and without formation of by-products. Its applicability in biosynthetic cascades is shown for the direct transformation of cinnamic acids into natural benzaldehydes (like vanillin) or artificial derivatives (e. g. ethylvanillin). (Figure presented.).
Biosynthesis of curcuminoids and gingerols in turmeric (Curcuma longa) and ginger (Zingiber officinale): Identification of curcuminoid synthase and hydroxycinnamoyl-CoA thioesterases
Ramirez-Ahumada, Maria del Carmen,Timmermann, Barbara N.,Gang, David R.
, p. 2017 - 2029 (2008/02/12)
Members of the Zingiberaceae such as turmeric (Curcuma longa L.) and ginger (Zingiber officinale Rosc.) accumulate at high levels in their rhizomes important pharmacologically active metabolites that appear to be derived from the phenylpropanoid pathway. In ginger, these compounds are the gingerols; in turmeric these are the curcuminoids. Despite their importance, little is known about the biosynthesis of these compounds. This investigation describes the identification of enzymes in the biosynthetic pathway leading to the production of these bioactive natural products. Assays for enzymes in the phenylpropanoid pathway identified the corresponding enzyme activities in protein crude extracts from leaf, shoot and rhizome tissues from ginger and turmeric. These enzymes included phenylalanine ammonia lyase, polyketide synthases, p-coumaroyl shikimate transferase, p-coumaroyl quinate transferase, caffeic acid O-methyltransferase, and caffeoyl-CoA O-methyltransferase, which were evaluated because of their potential roles in controlling production of certain classes of gingerols and curcuminoids. All crude extracts possessed activity for all of these enzymes, with the exception of polyketide synthases. 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. However, no gingerol synthase activity could be identified. This result was explained by the identification of thioesterase activities that cleaved phenylpropanoid pathway CoA esters, and which were found to be present at high levels in all tissues, especially in ginger tissues. These activities may shunt phenylpropanoid pathway intermediates away from the production of curcuminoids and gingerols, thereby potentially playing a regulatory role in the biosynthesis of these compounds.
QUINOLIZIDINE ALKALOIDS AND THE ENZYMATIC SYNTHESIS OF THEIR CINNAMIC AND HYDROXYCINNAMIC ACID ESTERS IN LUPINUS ANGUSTIFOLIUS AND L. LUTEUS
Strack, Dieter,Becher, Andrea,Brall, Sabine,Witte, Ludger
, p. 1493 - 1498 (2007/10/02)
The accumulation pattern of quinolizidine alkaloids during development of seedings and young plants of Lupinus angustifolius and L. luteus are described.The enzymes catalysing the syntheses of the cinnamic acid O-ester of 13-hydroxylupanine and hydroxycinnamic acid O-esters of lupinine (4-coumaroyl- and feruloyllupinine) are characterized and classified as cinnamoyl-CoA:13-hydroxylupanine O-cinnamoyltransferase (EC 2.3.1.-) and hydroxy cinnamoyl-CoA:lupinine O-hydroxycinnamoyltransferase (EC 2.3.1.-). Key Word Index - Lupinus angustifolius; L. luteus; Fabaceae; quinolizidine alkaloids; hydroxycinnamic acid esters; acyltransferase; hydroxycinnamoyl-coenzyme A; biosynthesis.
