Occurrence of Astringent Oligomeric Proanthocyanidins in Legume Seeds

Ariga, Toshiaki; Asao, Yasuo; Sugimoto, Hiroshi; Yokotsuka, Tamotsu

doi:10.1080/00021369.1981.10864962

Cited by 11 publications

(12 citation statements)

References 7 publications

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“…This high affinity is due to proline itself, an imino acid containing a carbonyl oxygen adjacent to a secondary amine nitrogen, which is a very good hydrogen bond acceptor, and to the open conformation of proline-rich proteins (Hagerman and Butler 1981 ;Haslam and Lilley 1988). Procyanidin-poly-L-proline interactions increased singificantly with the degree of procyanidin polymerisation, in agreement with other authors (Haslam 1974;Lea and Arnold 1978;Arnold et af 1980;Ariga et al 1981;Porter and Woodruffe 1984;Okuda et al 1985;Kumar and Horigome 1986;Artz ef al 1987;Yokotsuka and Singleton 1987) and with the degree of galloylation (Okuda et a1 1985) (Table In general, poly-L-proline binds procyanidins with increasing strength as the molecular weight increases (Butler et al1984), but the relative affinity of polyproline for procyanidin increases in a nonlinear fashion with the molecular weight of the protein, indicating that the protein-procyanidin interaction involves multiple binding sites (Hagerman and Butler 198 1 ). This probably explains why procyanidin losses are quite similar in the presence of poly-L-prolines A (40 000 amu) and B (1 9 000 amu) and different from poly-Lproline C , which presents the lowest molecular weight (6400 amu) (Table 3).…”

Section: Resultssupporting

confidence: 86%

Interaction of grape seed procyanidins with various proteins in relation to wine fining

Ricardo-da-Silva¹,

Cheynier²,

Souquet³

et al. 1991

J Sci Food Agric

171

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Interactions of grape (Vitis vinifera L) seed procyanidin dimers and trimers, galloylated or not, with various proteins (poly-L-prolines, gelatins, casein, dried blood and grape arabinogalactan-protein) were studied in wine-like model solutions. Except for casein, protein-procyanidin complexes were produced within the first 8 h of contact. All poly-L-prolines presented very high afinity towar& grape seed procyanidins. In general, the extent of procyanidin-protein interaction increased with the degree of procyanidin polymerisation and the rate of galloylation, andalso with protein concentration.When various protein3ning treatments were applied to a young red wine, dimeric and trimeric procyanidin levels were not aflected, although total phenolic levels were reduced.

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Section: Resultssupporting

confidence: 86%

Interaction of grape seed procyanidins with various proteins in relation to wine fining

Ricardo-da-Silva¹,

Cheynier²,

Souquet³

et al. 1991

J Sci Food Agric

171

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“…Plants produce abundant flavonoids, such as anthocyanins and proanthocyanidins (PAs; also called condensed tannins), in seed coats, leaves, fruits, flowers and barks (Ariga et al ., ; Dixon et al ., ; Gabetta et al ., ; Gu et al ., ). These flavonoids play protective roles in battles against microbial pathogen and pest attacks, UV protection and attracting insect pollinators (Dixon et al ., ; Santos‐Buelga and Scalbert, ; Zhao et al ., ).…”

Section: Introductionmentioning

confidence: 98%

Metabolic engineering of proanthocyanidin production by repressing the isoflavone pathways and redirecting anthocyanidin precursor flux in legume

Dong

Shu-jun

et al. 2016

Plant Biotechnology Journal

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Summary MtPAR is a proanthocyanidin (PA) biosynthesis regulator; the mechanism underlying its promotion of PA biosynthesis is not fully understood. Here, we showed that MtPAR promotes PA production by a direct repression of biosynthesis of isoflavones, the major flavonoids in legume, and by redirecting immediate precursors, such as anthocyanidins, flux into PA pathway. Ectopic expression of MtPAR repressed isoflavonoid production by directly binding and suppressing isoflavone biosynthetic genes such as isoflavone synthase (IFS). Meanwhile, MtPAR up‐regulated PA‐specific genes and decreased the anthocyanin levels without altering the expression of anthocyanin biosynthetic genes. MtPAR may shift the anthocyanidin precursor flux from anthocyanin pathway to PA biosynthesis. MtPAR complemented PA‐deficient phenotype of Arabidopsis tt2 mutant seeds, demonstrating their similar action on PA production. We showed the direct interactions between MtPAR, MtTT8 and MtWD40‐1 proteins from Medicago truncatula and Glycine max, to form a ternary complex to trans‐activate PA‐specific ANR gene. Finally, MtPAR expression in alfalfa (Medicago sativa) hairy roots and whole plants only promoted the production of small amount of PAs, which was significantly enhanced by co‐expression of MtPAR and MtLAP1. Transcriptomic and metabolite profiling showed an additive effect between MtPAR and MtLAP1 on the production of PAs, supporting that efficient PA production requires more anthocyanidin precursors. This study provides new insights into the role and mechanism of MtPAR in partitioning precursors from isoflavone and anthocyanin pathways into PA pathways for a specific promotion of PA production. Based on this, a strategy by combining MtPAR and MtLAP1 co‐expression to effectively improve metabolic engineering performance of PA production in legume forage was developed.

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“…We noted proanthocyanidin compounds, polyphenolic compounds with many isomers and analogues, which are widely found in the plant kingdom, including foods. Most people ingest trace amounts of proanthocyanidins through foods such as red wine, cranberry juice and azuki beans [1,2]. However, their functions and physiological properties were not fully understood because they have so many isomers and congeners that were difficult to isolate and characterize.…”

Section: Introductionmentioning

confidence: 99%

The antioxidative function, preventive action on disease and utilization of proanthocyanidins

Ariga

2004

BioFactors

Self Cite

143

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Proanthocyanidins, which belong to a class of polyphenols, are widely distributed throughout the plant kingdom. Most people ingest trace amounts of proanthocyanidins through foods such as red wine and cranberry juice. However, the functional properties of proanthocyanidins have been little understood. Since 1983, we have studied the antioxidative functions, preventive actions on diseases and utilization of proanthocyanidins. The antioxidative activities of proanthocyanidins were found to be much stronger than vitamin C or vitamin E in aqueous systems. The mechanisms for their antioxidative actions were shown to involve radical scavenging, quenching, and enzyme-inhibiting actions. The preventive actions of proanthcyanidins on diseases relating to reactive oxygen species was examined using animal tests. Proanthocyanidin-rich grape seed extract was showed to have preventive actions on diseases such as atherosclerosis, gastric ulcer, large bowel cancer, cataracts and diabetes. In human intervention trials, grape seed extract was shown to have preventive effects on the increase in lipid peroxides in human plasma after exercise and on muscle fatigue after training. The uses and manufacturing techniques of proanthocyanidin products were subsequently developed. The products were launched as antioxidants in food additives, ingredients in nutritional supplements, and cosmetics.

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Occurrence of Astringent Oligomeric Proanthocyanidins in Legume Seeds

Cited by 11 publications

References 7 publications

Interaction of grape seed procyanidins with various proteins in relation to wine fining

Interaction of grape seed procyanidins with various proteins in relation to wine fining

Metabolic engineering of proanthocyanidin production by repressing the isoflavone pathways and redirecting anthocyanidin precursor flux in legume

The antioxidative function, preventive action on disease and utilization of proanthocyanidins

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