Catechins and Proanthocyanidins: Naturally Occurring O-Heterocycles with Antimicrobial Activity

Buzzini, Pietro; Turchetti, Benedetta; Ieri, Francesca; Goretti, Marta; Branda, Eva; Mulinacci, Nádia; Romani, Annalisa

doi:10.1007/7081_2007_065

Cited by 17 publications

(8 citation statements)

References 106 publications

(115 reference statements)

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“…PAs are oligomers or polymers composed of flavan-3-ol units. The structure of PAs varies depending on the features of flavan-3-ols (as a starter or extension unit), the degree of polymerization [ 3 , 21 ], the position of the interflavan linkage between the monomeric units [ 4 , 21 , 23 ], and esterification of the 3-hydoxyl group [ 3 , 20 , 24 , 25 ]. Among these factors, the nature of flavan-3-ols (stereochemistry at the chiral center and hydroxyl patterns) is a key concept for understanding the structural variability of PAs.…”

Section: Biosynthetic Pathways Of Pas and Anthocyaninsmentioning

confidence: 99%

“…PAs are a group of oligomers and polymers composed of flavan-3-ols—the most common subclass of flavonoids. Depending on the composition of the monomer precursor, the type of PA varies, including catechin, epicatechin, gallocatechin, epigallocatechin, afzelechin, and epiafzelechin, which are commonly found in the plant kingdom [ 2 , 20 , 21 , 22 ].…”

Section: Introductionmentioning

confidence: 99%

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Biosynthetic Pathway of Proanthocyanidins in Major Cash Crops

Lim

2021

Plants

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Proanthocyanidins (PAs) are a group of oligomers or polymers composed of monomeric flavanols. They offer many benefits for human fitness, such as antioxidant, anticancer, and anti-inflammatory activities. To date, three types of PA have been observed in nature: procyanidins, propelargonidins, and prodelphinidins. These are synthesized as some of the end-products of the flavonoid pathway by different consecutive enzymatic activities, from the same precursor—naringenin. Although the general biosynthetic pathways of PAs have been reported in a few model plant species, little is known about the species-specific pathways in major crops containing different types of PA. In the present study, we identified the species-specific pathways in 10 major crops, based on the presence/absence of flavanol-based intermediates in the metabolic pathway, and found 202 orthologous genes in the reference genomic database of each species, which may encode for key enzymes involved in the biosynthetic pathways of PAs. Parallel enzymatic reactions in the pathway are responsible for the ratio between PAs and anthocyanins, as well as among the three types of PAs. Our study suggests a promising strategy for molecular breeding, to regulate the content of PAs and anthocyanins and improve the nutritional quality of food sources globally.

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Section: Biosynthetic Pathways Of Pas and Anthocyaninsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Biosynthetic Pathway of Proanthocyanidins in Major Cash Crops

Lim

2021

Plants

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“…Further more, although flavanols and their oligomers or polymers are widespread in plants, their isolation usually requires time-consuming procedures and both quality and reproducibility are usually unsatisfactory. Meanwhile, potential substrates of PA condensation are not all commercially available due to their potential multiform stereochemistry and the instability conferred by their strong reducibility, which cause trouble to the studies on the mechanism of PA polymerization and the improvement of their biological activities [ 12 ]. To overcome these difficulties, great efforts have been devoted into the chemical synthesis of flavanols and PAs.…”

Section: Introductionmentioning

confidence: 99%

Chemical Synthesis of Proanthocyanidins in Vitro and Their Reactions in Aging Wines

Pan

Shi

et al. 2008

Molecules

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Proanthocyanidins are present in many fruits and plant products like grapes and wine, and contribute to their taste and health benefits. In the past decades of years, substantial progresses has been achieved in the identification of composition and structure of proanthocyanidins, but the debate concerning the existence of an enzymatic or nonenzymatic mechanism for proanthocyanidin condensation still goes on. Substantial attention has been paid to elucidating the potential mechanism of formation by means of biomimetic and chemical synthesis in vitro. The present paper aims at summarizing the research status on chemical synthesis of proanthocyanidins, including non-enzymatic synthesis of proanthocyanidin precursors, chemical synthesis of proanthocyanidins with direct condensation of flavanols and stereoselective synthesis of proanthocyanidins. Proanthocyanidin-involved reactions in aging wines are also reviewed such as direct and indirect reactions among proanthocyanidins, flavanols and anthocyanins. Topics for future research in this field are also put forward in this paper.

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“…The presence or absence of modifications of the monomeric flavan-3-ol units further enhances the structure complexity of PAs. Various methyl, acyl or glycosyl substituents of the monomeric units of PAs all occur in natural products [ 28 ]. For example, the 3-hydroxyl group of the flavan-3-ol units of B-type PAs in grape seeds is usually esterified with gallic acid [ 1 ].…”

Section: Structures Of Proanthocyanidinsmentioning

confidence: 99%

“…highlighted this comment and further speculated on the potential commonalities between them with respect to their mode of assembly and the importance of their stereochemistry [ 1 ]. Besides these, other previous reviews summarized the foregoing achievement in almost every aspect of the study of PAs mainly in the past 20 years [ 2 , 7 , 9 , 22 , 23 , 25 , 26 , 27 , 28 , 29 , 30 , 31 ]. This paper will review the important concepts and updates in the research of PAs with regard to the elucidation of structure and stereochemistry, the general biosynthetic pathway, the potential polymerization mechanisms, their transport, regulation and genetic manipulation.…”

Section: Introductionmentioning

confidence: 99%

Biosynthesis and Genetic Regulation of Proanthocyanidins in Plants

et al. 2008

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Proanthocyanidins (PAs), also known as condensed tannins, are a group of polyphenolic secondary metabolites synthesized in plants as oligomers or polymers of flavan-3-ol units via the flavonoid pathway. Due to their structural complexity and varied composition, only in the recent years has the study on the biosynthesis and regulation of PAs in plants taken off, although some details of the synthetic mechanism remain unclear. This paper aims to summarize the status of research on the structures of PAs in plants, the genes encoding key enzymes of biosynthetic pathway, the transport factors, the transcriptional regulation of PA biosynthesis and the genetic manipulation of PAs. The problems of this field were also discussed, including the nature of the final “enzyme” which catalyzes the polymerization reaction of PAs and the possible mechanism of how the elementary units of flavanols are assembled in vivo.

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Catechins and Proanthocyanidins: Naturally Occurring O-Heterocycles with Antimicrobial Activity

Cited by 17 publications

References 106 publications

Biosynthetic Pathway of Proanthocyanidins in Major Cash Crops

Biosynthetic Pathway of Proanthocyanidins in Major Cash Crops

Chemical Synthesis of Proanthocyanidins in Vitro and Their Reactions in Aging Wines

Biosynthesis and Genetic Regulation of Proanthocyanidins in Plants

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