Molecular Structures of the Stem Tuber Anthocyanins of Colored Potatoes and Their Coloring Effects on the Tubers

2015 ◽  
Vol 10 (3) ◽  
pp. 1934578X1501000 ◽  
Author(s):  
Chang Ling Zhao ◽  
Guo Song Wen ◽  
Zi Chao Mao ◽  
Shao Zhong Xu ◽  
Zheng Jie Liu ◽  
...  
Keyword(s):  
Phenolic Acids ◽  
Molecular Structures ◽  
Glycosidic Bond ◽  
Coumaric Acid ◽  
Potato Tubers ◽  
Naturally Occurring ◽  
Substituent Group ◽  
Colored Potatoes ◽  
Coloration Patterns ◽  
Derivatives Of

This paper summarized the important achievements about the general characteristics of the molecular structures of the stem tuber anthocyanins of Colored potatoes and the basic coloring effects of the anthocyanins on the tubers. The various coloration patterns of the skins and/or flesh of Colored potato tubers result from the accumulation of the anthocyanins in the periderms, phelloderms and/or peripheral cortices of the tubers, and the tuber colors are fundamentally determined by the matching profiles of the six naturally occurring anthocyanidins, i.e., cyanidin, delphinidin, malvidin, pelargonidin, peonidin and petunidin. Generally, the tuber anthocyanidins hold an O-glycosidic bond-linked rutinosyl at the C3 site, and either a glucosyl linked by an O-glycosidic bond or no substituent group may exist at the C5 site simultaneously. Furthermore, an E-monoacyl frequently exists at the C3- rutinosyls or at the C5-glucosyls of most tuber anthocyanins, and the phenolic acids acylating the tuber anthocyanins are often p-coumaric, ferulic and caffeic acids. The popular names of the p-coumaric acid derivatives of the malvidin, pelargonidin, peonidin and petunidin of the tubers are Malvanin, Pelanin, Peonanin and Petanin, respectively. This review provides a reference for the exploration of the mechanism of the tuber coloration and the identification of the molecular structures of the stem tuber anthocyanins of Colored potatoes.

Hydroxycinnamoyl: Coenzyme A Transferase Involved in the Biosynthesis of Kaempferol-3-(p-coumaroyl Triglucoside) in Pisum sativum

1977 ◽  
Vol 32 (9-10) ◽  
pp. 765-768 ◽  
Author(s):  
Marie H. Saylor ◽  
Richard L. Mansell
Keyword(s):  
Coenzyme A ◽  
Chemical Properties ◽  
Acyl Donor ◽  
Coumaric Acid ◽  
Enzyme Preparations ◽  
Naturally Occurring ◽  
Enzymatic Formation ◽  
Derivatives Of ◽  
Acid Esters ◽  
And Chemical Properties

Abstract The major flavonoids of Pisum are derivatives of kaempferol and quercetin, including both tri-glucosides and acylated triglucosides in which the acyl group is p-coumaric acid. Although hydroxy-cinnamic acid esters of flavonoids are common pigments in many plants, neither the enzymes nor the precursors involved in their biosynthesis have been demonstrated. We report here that crude enzyme preparations extracted from peas catalyze the transfer of the p-coumaroyl moiety of p-coumaroyl: Coenzyme A to kaempferol-3-triglucoside forming kaempferol-3-(p-coumaroyl triglucoside) as the acylated product. The reaction product has been vigorously shown to be identical to the naturally occurring kaempferol-3-(p-coumaroyl triglucoside) in both chromatographic and chemical properties. The enzymatic formation of the acylated derivative occurred only minimally when incubated with the cofactors required for carboxyl group activation (ligase) and maximally when incubated with p-coumaroyl : Coenzyme A as the acyl donor.

Photolysis of Aqueous Chlorimuron and Imazaquin in the Presence of Phenolic Acids and Riboflavin

Weed Science ◽  
1993 ◽  
Vol 41 (3) ◽  
pp. 454-459 ◽  
Author(s):  
Ramarao Venkatesh ◽  
S. Kent Harrison ◽  
Mark M. Loux
Keyword(s):  
Organic Compounds ◽  
Phenolic Acids ◽  
Surface Waters ◽  
Half Life ◽  
Laboratory Experiments ◽  
Uv Light ◽  
Aqueous Media ◽  
Quantum Yields ◽  
Coumaric Acid ◽  
Naturally Occurring

Laboratory experiments were conducted to determine the effect of three phenolic acids, acetone, and riboflavin on aqueous photolysis of chlorimuron and imazaquin. The phenolic acids investigated were caffeic acid (CA), ferulic acid (FA), andp-coumaric acid (PCA). Treatment solutions were contained in quartz vessels and irradiated with 300 to 400 nm UV light in a photoreactor. The extrapolated photolysis half-life of chlorimuron in pure solution was 107 h, compared to a half-life of 0.42 h for pure aqueous imazaquin. Chlorimuron in solutions containing 10 ppmw riboflavin, acetone, CA, FA, or PCA exhibited half-lives of 9, 57, 58, 67, and 146 h, respectively. Imazaquin in solutions containing 10 ppmw riboflavin, acetone, CA, FA, or PCA had half-lives of 0.70, 0.55, 0.55, 0.48, and 0.55 h, respectively. The presence of PCA in aqueous media delayed chlorimuron photolysis, whereas all other compounds, especially riboflavin, sensitized chlorimuron photolysis. In contrast, imazaquin photolysis was delayed in the presence of the test compounds, with riboflavin having the greatest effect and causing in a 68% increase in imazaquin half-life over that of imazaquin alone. Quantum yields for sensitized photolysis of chlorimuron by riboflavin and for riboflavin by imazaquin were 0.1134 and 0.0477, respectively. These results suggest that some soluble and naturally occurring organic compounds may enhance chlorimuron photolysis yet delay imazaquin photolysis in surface waters.

scholarly journals Resolving Entangled JH-H-Coupling Patterns for Steroidal Structure Determinations by NMR Spectroscopy

Molecules ◽  
2021 ◽  
Vol 26 (9) ◽  
pp. 2643
Author(s):  
Danni Wu ◽  
Kathleen Joyce Carillo ◽  
Jiun-Jie Shie ◽  
Steve S.-F. Yu ◽  
Der-Lii M. Tzou
Keyword(s):  
Nmr Spectroscopy ◽  
1H Nmr Spectroscopy ◽  
Chemical Shifts ◽  
Atomic Level ◽  
Molecular Structures ◽  
Naturally Occurring ◽  
Structure Determinations ◽  
Ligand Interactions ◽  
Synthetic Steroids ◽  
The Individual

For decades, high-resolution 1H NMR spectroscopy has been routinely utilized to analyze both naturally occurring steroid hormones and synthetic steroids, which play important roles in regulating physiological functions in humans. Because the 1H signals are inevitably superimposed and entangled with various JH–H splitting patterns, such that the individual 1H chemical shift and associated JH–H coupling identities are hardly resolved. Given this, applications of thess information for elucidating steroidal molecular structures and steroid/ligand interactions at the atomic level were largely restricted. To overcome, we devoted to unraveling the entangled JH–H splitting patterns of two similar steroidal compounds having fully unsaturated protons, i.e., androstanolone and epiandrosterone (denoted as 1 and 2, respectively), in which only hydroxyl and ketone substituents attached to C3 and C17 were interchanged. Here we demonstrated that the JH–H values deduced from 1 and 2 are universal and applicable to other steroids, such as testosterone, 3β, 21-dihydroxygregna-5-en-20-one, prednisolone, and estradiol. On the other hand, the 1H chemical shifts may deviate substantially from sample to sample. In this communication, we propose a simple but novel scheme for resolving the complicate JH–H splitting patterns and 1H chemical shifts, aiming for steroidal structure determinations.

METABOLISM OF PHENYLPROPANOID COMPOUNDS IN SALVIA: II. BIOSYNTHESIS OF PHENOLIC CINNAMIC ACIDS

1959 ◽  
Vol 37 (1) ◽  
pp. 537-547 ◽  
Author(s):  
D. R. McCalla ◽  
A. C. Neish
Keyword(s):  
Caffeic Acid ◽  
Phenolic Acids ◽  
Cinnamic Acid ◽  
Shikimic Acid ◽  
Sinapic Acid ◽  
Coumaric Acid ◽  
Cinnamic Acids ◽  
Phenyllactic Acid ◽  
Salvia Splendens ◽  
Specific Activities

p-Coumaric, caffeic, ferulic, and sinapic acids were found to occur in Salvia splendens Sello in alkali-labile compounds of unknown constitution. A number of C14-labelled compounds were administered to leafy cuttings of salvia and these phenolic acids were isolated after a metabolic period of several hours and their specific activities measured. Cinnamic acid, dihydrocinnamic acid, L-phenylalanine, and (−)-phenyllactic acid were found to be good precursors of the phenolic acids. D-Phenylalanine, L-tyrosine, and (+)-phenyllactic acid were poor precursors. A kinetic study of the formation of the phenolic acids from L-phenylalanine-C14 gave data consistent with the view that p-coumaric acid → caffeic acid → ferulic acid → sinapic acid, and that these compounds can act as intermediates in lignification. Feeding of C14-labelled members of this series showed that salvia could convert any one to a more complex member of the series but not so readily to a simpler member. Caffeic acid-β-C14 was obtained from salvia after the feeding of L-phenylalanine-β-C14 or cinnamic acid-β-C14, and caffeic acid labelled only in the ring was obtained after feeding generally labelled shikimic acid.

scholarly journals Hyperbranched Molecular Structures with Potential Antiviral Activity: Derivatives of 5,6-Dihydroxyindole-2-Carboxylic Acid

Molecules ◽  
2006 ◽  
Vol 11 (12) ◽  
pp. 968-977 ◽  
Author(s):  
Mario Sechi ◽  
Fabio Casu ◽  
Ilaria Campesi ◽  
Stefano Fiori ◽  
Alberto Mariani
Keyword(s):  
Carboxylic Acid ◽  
Antiviral Activity ◽  
Molecular Structures ◽  
Derivatives Of

scholarly journals Thermodynamically stable [4 + 2] cycloadducts of lanthanum-encapsulated endohedral metallofullerenes

2014 ◽  
Vol 10 ◽  
pp. 714-721 ◽  
Author(s):  
Yuta Takano ◽  
Yuki Nagashima ◽  
M Ángeles Herranz ◽  
Nazario Martín ◽  
Takeshi Akasaka
Keyword(s):  
Thermal Stability ◽  
Material Science ◽  
Molecular Structures ◽  
Spectroscopic Methods ◽  
Dynamic Nmr ◽  
The Novel ◽  
Endohedral Metallofullerenes ◽  
Derivatives Of ◽  
Paramagnetic Properties

The [4 + 2] cycloaddition of o-quinodimethanes, generated in situ from the sultine 4,5-benzo-3,6-dihydro-1,2-oxathiin 2-oxide and its derivative, to La metal-encapsulated fullerenes, La2@C80 or La@C82, afforded the novel derivatives of endohedral metallofullerenes (3a,b, 4a,b and 5b). Molecular structures of the resulting compounds were elucidated using spectroscopic methods such as MALDI–TOF mass, optical absorption, and NMR spectroscopy. The [4 + 2] adducts of La2@C80 (3a,b, and 4a,b) and La@C82 (5b), respectively, retain diamagnetic and paramagnetic properties, as confirmed by EPR spectroscopy. Dynamic NMR measurements of 4a at various temperatures demonstrated the boat-to-boat inversions of the addend. In addition, 5b revealed remarkable thermal stability in comparison with the reported [4 + 2] cycloadduct of pentamethylcyclopentadiene and La@C82 (6). These findings demonstrate the utility of sultines to afford thermodynamically stable endohedral metallofullerene derivatives for the use in material science.

scholarly journals Identification of the Tyrosine- and Phenylalanine-Derived Soluble Metabolomes of Sorghum

2021 ◽  
Vol 12 ◽  
Author(s):  
Jeffrey P. Simpson ◽  
Jacob Olson ◽  
Brian Dilkes ◽  
Clint Chapple
Keyword(s):  
Amino Acids ◽  
Cinnamic Acid ◽  
Aromatic Amino Acids ◽  
Flavonoid Glycosides ◽  
Coumaric Acid ◽  
Biotic And Abiotic Stress ◽  
Proportional Contribution ◽  
Negative Ionization ◽  
Derivatives Of

The synthesis of small organic molecules, known as specialized or secondary metabolites, is one mechanism by which plants resist and tolerate biotic and abiotic stress. Many specialized metabolites are derived from the aromatic amino acids phenylalanine (Phe) and tyrosine (Tyr). In addition, the improved characterization of compounds derived from these amino acids could inform strategies for developing crops with greater resilience and improved traits for the biorefinery. Sorghum and other grasses possess phenylalanine ammonia-lyase (PAL) enzymes that generate cinnamic acid from Phe and bifunctional phenylalanine/tyrosine ammonia-lyase (PTAL) enzymes that generate cinnamic acid and p-coumaric acid from Phe and Tyr, respectively. Cinnamic acid can, in turn, be converted into p-coumaric acid by cinnamate 4-hydroxylase. Thus, Phe and Tyr are both precursors of common downstream products. Not all derivatives of Phe and Tyr are shared, however, and each can act as a precursor for unique metabolites. In this study, 13C isotopic-labeled precursors and the recently developed Precursor of Origin Determination in Untargeted Metabolomics (PODIUM) mass spectrometry (MS) analytical pipeline were used to identify over 600 MS features derived from Phe and Tyr in sorghum. These features comprised 20% of the MS signal collected by reverse-phase chromatography and detected through negative-ionization. Ninety percent of the labeled mass features were derived from both Phe and Tyr, although the proportional contribution of each precursor varied. In addition, the relative incorporation of Phe and Tyr varied between metabolites and tissues, suggesting the existence of multiple pools of p-coumaric acid that are fed by the two amino acids. Furthermore, Phe incorporation was greater for many known hydroxycinnamate esters and flavonoid glycosides. In contrast, mass features derived exclusively from Tyr were the most abundant in every tissue. The Phe- and Tyr-derived metabolite library was also utilized to retrospectively annotate soluble MS features in two brown midrib mutants (bmr6 and bmr12) identifying several MS features that change significantly in each mutant.

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