The biosynthesis of coumarin in Melilotus alba

Stoker, J.R.

doi:10.1016/0006-291x(63)90203-1

Cited by 23 publications

(14 citation statements)

References 6 publications

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“…The maximum level of MEA (>1 g/L) even exceeded the concentration of free COU in the tonka beans at the beginning of the biotransformation experiment (2% w/v or 0.5 g of COU/ L), which had been calculated by HPLC-DAD analysis of a tonka bean hexane extract (Figure 4). This prompts the speculation that the O-glucoside of oCA, melilotoside, constitutes an additional pool of COU in tonka beans that can release the precursor of MEA during the bioprocess (26)(27)(28). The normal procedure for liberating COU from tonka beans involves soaking for 24 h and drying, whereby a fermentation process takes place.…”

Section: Discussionmentioning

confidence: 98%

Biocatalytic Production of Dihydrocoumarin from Coumarin by Saccharomyces cerevisiae

Häser

Wenk

Schwab

2006

J. Agric. Food Chem.

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Natural dihydrocoumarin, which is of great interest in the flavor industry, was biotechnologically produced from pure coumarin or tonka bean meal with Pseudomonas orientalis, Bacillus cereus, and various Saccharomyces cerevisiae strains. Coumarin was shown to be converted to melilotic acid, which yielded dihydrocoumarin upon distillation during purification. About 1.0 g/L product was obtained from 25 g/L tonka beans with S. cerevisiae within 147 h. This dihydrocoumarin thus fulfills all of the criteria of a natural raw material and can be used as a natural flavoring in accordance with U.S. and European Union regulations.

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Section: Discussionmentioning

confidence: 98%

Biocatalytic Production of Dihydrocoumarin from Coumarin by Saccharomyces cerevisiae

Häser

Wenk

Schwab

2006

J. Agric. Food Chem.

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“…The accumulation of the cis -isomer of p -coumaroylagmatine in S. moellendorffii and A. julibrissin further implies the existence of p -coumaroyl trans – cis isomerases in these species. This type of trans – cis isomerase is currently an undefined biosynthetic activity, which is also suggested to be critical in the biosynthesis of cis -coumarinic acid-β-D-glucoside in Melilotus alba (Stoker, 1964). …”

Section: Alkaloidsmentioning

confidence: 99%

Chemodiversity in Selaginella: a reference system for parallel and convergent metabolic evolution in terrestrial plants

Weng

Noel

2013

Front. Plant Sci.

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Early plants began colonizing the terrestrial earth approximately 450 million years ago. Their success on land has been partially attributed to the evolution of specialized metabolic systems from core metabolic pathways, the former yielding structurally and functionally diverse chemicals to cope with a myriad of biotic and abiotic ecological pressures. Over the past two decades, functional genomics, primarily focused on flowering plants, has begun cataloging the biosynthetic players underpinning assorted classes of plant specialized metabolites. However, the molecular mechanisms enriching specialized metabolic pathways during land plant evolution remain largely unexplored. Selaginella is an extant lycopodiophyte genus representative of an ancient lineage of tracheophytes. Notably, the lycopodiophytes diverged from euphyllophytes over 400 million years ago. The recent completion of the whole-genome sequence of an extant lycopodiophyte, S. moellendorffii, provides new genomic and biochemical resources for studying metabolic evolution in vascular plants. 400 million years of independent evolution of lycopodiophytes and euphyllophytes resulted in numerous metabolic traits confined to each lineage. Surprisingly, a cadre of specialized metabolites, generally accepted to be restricted to seed plants, have been identified in Selaginella. Initial work suggested that Selaginella lacks obvious catalytic homologs known to be involved in the biosynthesis of well-studied specialized metabolites in seed plants. Therefore, these initial functional analyses suggest that the same chemical phenotypes arose independently more commonly than anticipated from our conventional understanding of the evolution of metabolism. Notably, the emergence of analogous and homologous catalytic machineries through convergent and parallel evolution, respectively, seems to have occurred repeatedly in different plant lineages.

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“…The biosynthesis of coumarins in plants transits via cyclization of hydroxycinnamic acid [76]. In general, coumarin derivatives manifest great chemical diversity, mainly differing in the oxygenation degree of their benzopyrone moiety.…”

Section: Coumarinsmentioning

confidence: 99%

Natural Polyphenols that Display Anticancer Properties through Inhibition of Kinase Activity

Lamoral-Theys¹,

Pottier

Dufrasne³

et al. 2010

CMC

124

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Over eleven hundred publications reporting anticancer activities of polyphenols have appeared in the peerreviewed literature. In addition, a search of the PubMed database using "polyphenols -cancer -review" as keywords produced over 320 hits for review articles (July 2009). Polyphenol anticancer activities include, among others, anti-oxidative, pro-apoptotic, DNA damaging, anti-angiogenic, and immunostimulatory effects. Targeting specific protein kinases to combat cancer represents a major focus of oncology research within the so-called targeted therapy approach. An exhaustive search of the PubMed database (July 2009) using "polyphenols -cancer -kinases" as keywords resulted in more than 130 hits, half of them having been published within the past five years. Furthermore, the PubMed database contains 25 reviews on the subject of anti-kinase activity of some specific polyphenols, including mainly curcumin and the green tea polyphenol (-)-epigallocatechin 3-gallate (EGCG). However, no attempt has been made yet to review this area of research in a comprehensive, general manner. The current review therefore aims to highlight those anticancer polyphenols that target specific kinases in various types of cancer. The present review also provides an in-depth analysis of polyphenol structure-activity relationships in relation to their anticancer activities and specific kinase targeting. Lastly, a number of polyphenols are identified as potential antitumor agents that could be used to combat biologically aggressive cancers, including metastasizing cancers, through the targeting of specific kinases.

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The biosynthesis of coumarin in Melilotus alba

Cited by 23 publications

References 6 publications

Biocatalytic Production of Dihydrocoumarin from Coumarin by Saccharomyces cerevisiae

Biocatalytic Production of Dihydrocoumarin from Coumarin by Saccharomyces cerevisiae

Chemodiversity in Selaginella: a reference system for parallel and convergent metabolic evolution in terrestrial plants

Natural Polyphenols that Display Anticancer Properties through Inhibition of Kinase Activity

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