Hydroxycinnamoyl acid amides and aromatic amines in the inflorescences of some araceae species

Hydroxycinnamoyl acid amides (HCA's) were found to be important components in the inflorescences of different Araceae species. HCA's occurred in large amount in spathes and in the male and female flowers, and were totally absent from the sterile flowers, commonly found on Araceae spadices. Differences in the distribution of HCA's were noted between male and female flowers. Thus the amount of neutral HCA's was always greater in the male than in the female flowers and the female flowers generally contained more basic HCA'S. In the inflorescences of some Araceae species in the Monsteroideae and Philodendroideae (genera Monstera, Raphidophora and Philodendron), the aromatic amines tyramine and dopamine were very abundant, with concentrations ranging from 1 to 4 mg of each amine per g fr. wt.     

Hydroxycinnamic acid amides in fertile and cytoplasmic male sterile lines of maize

Hydroxycinnamic acid (HCA) amides in fertile and cytoplasmic male sterile lines of maize were determined in reproductive organs, developing grains and cobs. HCA amides occurred in large amounts in the anthers of fertile plants (line F7N) and were absent from the anthers of cytoplasmic male sterile lines (lines F7T and F7C). Restoration of fertility was associated with the production of these compounds (line FC31). Considerable variations were observed in the concentrations of HCA amides at different stages of growth and grain maturation. Changes of HCA amides in the grains which were to produce sterile plants followed a pattern similar to that obtained with the grains which were to produce fertile plants. Accumulation of HCA amides was substantially higher in fertile lines whatever their genotype (F7N, FC31 and F7T x FC31) than in sterile lines. Marked changes occurred in the HCA amide content of embryo and endosperm during grain development. Many changes in HCA amides were observed in cobs during development and maturation, but no substantial differences could be observed between fertile and sterile lines.     

Hydroxycinnamic acid amides and ripening to flower of Nicotiana tabacum var. xanthi n.c.

Two kinds of hydroxycinnamic derivatives can be found in tobacco: esters and amides. They do not accumulate in the same way during development. Esters, especially chlorogenic acids, are always present in all organs, whereas amides are observed only during certain periods in specific organs (from 47 days after sowing, in apical leaves, anthers and ovaries). A relationship has been found between accumulation of amides and flowering of plants grown at 20°C. By comparing amide accumulation as well as leaf emergence rate, both at a temperature that allows flowering (20°C) and at a temperature that inhibits flowering (30°C), it appears that amides begin to accumulate whenever a plant is ripening to flower.     

Theoretical analysis of the deactivation reactions of triplet state riboflavin by hydroxycinnamic acid derivatives

A thermodynamic analysis of the deactivation reactions of triplet state riboflavin (RF) by hydroxycinnamic acid derivatives has been performed on the basis of quantum chemical calculations. It was revealed that the H-atom transfer pathway is more thermodynamically feasible in comparison with the direct energy/electron transfer to be involved in the triplet state RF quenching by hydroxycinnamic acid derivatives. The results provide some deeper insights into the protective behaviours of hydroxycinnamic acid derivatives against the RF induced photooxidative damage.     

Characterization of cross-linked hydroxycinnamic acid amides isolated from potato common scab lesions

Four feruloyl amides, N-trans-feruloyloctopamine (1), N-cis-feruloyloctopamine (2), N-trans-feruloyltyramine (3), N-cis-feruloyltyramine (4), a cross-linked N-trans-feruloyltyramine dimer (5), and a cross-linked N-cis-feruloyltyramine dimer (6) were isolated from potato common scab lesions. The compounds were purified by TLC and characterized by a combination of (1)H and (13)C NMR spectroscopic techniques. The presence of an accompanying minor complex of cross-linked dimers containing both feruloyltyramines and feruloyloctopamines was also demonstrated. This is the first characterization of cross-linked hydroxycinnamic acid amides associated with wound healing in potato (Solanum tuberosum) tubers.     

Hydroxybenzoic and hydroxycinnamic acid derivatives in soft fruits

Quinic acid and glucose esters of hydroxycinnamic acids and glucosides of hydroxycinnamic and hydroxybenzoic acids have been determined by capillary GC and HPLC in soft fruits. The results confirm the wide distribution of these compounds in fruit tissues.     

Modification of primary and secondary metabolism of potato plants by nitrogen application differentially affects resistance to Phytophthora infestans and Alternaria solani

Potato plants ( SOLANUM TUBEROSUM L. cv. Indira) were grown at two levels of N supply in the greenhouse. Plants supplied with 0.8 g N per plant (high N variant) showed significantly increased biomass as compared to plants without additional N fertilisation (low N variant). C/N ratio was lower and protein content was higher in leaves of the high N variant. The concentration of chlorogenic acids and flavonols was significantly lower in leaves from the high N variant. Whereas resistance to ALTERNARIA SOLANI increased when plants were supplied with additional nitrogen, these plants were more susceptible to PHYTOPHTHORA INFESTANS. After infection with both pathogens, we found a strong induction of p-coumaroylnoradrenaline and p-coumaroyloctopamine, which are identified for the first time in potato leaves and are discussed as resistance factors of other solanaceous plants.     

Relationship between hydroxycinnamic acid content,lignin composition and digestibility of maize silages in sheep

Cell wall-bound hydroxycinnamic acids and the composition of lignin were studied in relation to the digestibility of a collection of 91 maize silages in wethers. Total lignin and guaiacyl content showed the highest correlation coefficients with digestibility. Using the above-mentioned chemical parameters, eight equations were also developed to predict digestibility. The prediction of organic matter digestibility produced a high adjusted R ² value (0.487) using total lignin, guaiacyl, esterified ferulic acid and esterified p-coumaric acid content as predictors. The prediction of in vivo dry matter digestibility produced a higher adjusted R ² value (0.516) using the same variables as predictors. Cell wall digestibility depends on a multiplicity of factors and it is not possible to attribute a causal effect on in vivo digestibility to any single factor. However, total lignin, guaiacyl and p-coumaric acid content emerge as good predictors of digestibility.     

Phenolamides during the ripening of dormant and non-dormant seeds in different Petunia lines

Phenolamides were extracted from reproductive organs and different capsule parts (fruit wall, placenta and seeds) of dormant and non-dormant lines derived from the species Petunia hybrida hort,. Petunia axillaries Lam. B.S.P. and Petunia parodii Steere. The different compounds were separated by high-pressure liquid chromatography and analyzed before pollination, during ripening, at ripeness and after 2 weeks of after-ripening of the seeds. The extracts were examined particularly for the presence of an alkaline compound (X), which is a phenolic derivative of tryptophanamide and appears to be a biochemical marker for the dormancy of ripe dry seeds of Petunia. During capsule growth and seed ripening, compound X was not a marker for dormancy, although it occurred in the reproductive organs of seed-parent plants. After pollination and fertilization, accumulation of compound X started mainly in the fruit wall, but in ripe dry capsules it was present entirely in the seeds. In contrast to compound X, neutral phenolamides were not detected in extracts from the fruit wall: and from the early stages of the capsule growth substantial accumulation took place only in the seeds.
Absence of compound X from ripe dry seeds appears as a necessary but not a sufficient condition for non-dormancy.     

One-pot synthesis of polyunsaturated fatty acid amides with anti-proliferative properties

A one-pot environmentally friendly transamidation of ω-3 fatty acid ethyl esters to amides and mono- or diacylglycerols was investigated via the use of a polymer-supported lipase. The method was used to synthesize a library of fatty acid monoglyceryl esters and amides. These new derivatives were found to have potent growth inhibition effects against A549 lung cancer cells.     

Lipase-catalysed ammoniolysis of lipids. A facile synthesis of fatty acid amides

Ammoniolysis of triglycerides to the corresponding fatty acid amides is efficiently catalysed byCandida antarctica lipase (Novozym 435). Thus, olive oil gave 90% of nearly pure oleamide after 72 h at 60°C. Jojoba wax was similarly converted into a mixture ofcis-11-eicosenamide and erucamide together withcis-11-eicosenol andcis-l3-docosenol.     

The distribution and properties of NADP malic enzyme in flowering plants

Malic enzyme is shown to be widely distributed in higher plants and contrary to earlier reports is present in the roots of flood tolerant species. Excluding members of the Gramineae, the malic enzyme from 27 out of 28 species examined was shown to exhibit allosteric properties. On the other hand the malic enzyme present in members of the Gramineae shows little or no allosteric properties.     

Vacuolar localization of the enzymatic synthesis of hydroxycinnamic acid esters of malic acid in protoplasts from Raphanus sativus leaves

Protoplasts from leaves of radish ( Raphanus sativus L. var. sativus ) were examined for the subcellular localization of p -coumaric, caffeic, ferulic and sinapic acid esters of malic acid and the enzyme(s) involved in their syntheses. Vacuoles isolated from leaf protoplasts contained all the hydroxycinnamic acid esters as well as all the dependent enzyme activities. Protein from leaf vacuoles was shown to form the hydroxycinnamoylmalic acids, using the corresponding hydroxycinnamic acid glucose esters (1-O-acyl glucosides) as acyl donors. It is proposed that the vacuole is the cell compartment for synthesis and deposition of the hydroxycinnamoylmalic acids.     

Quinyl esters and glucose derivatives of hydroxycinnamic acids during growth and ripening of tomato fruit

Quinyl esters of hydroxycinnamic acids usually occur in greater abundance than their corresponding glucose esters in tomato fruits. During fruit growth and ripening, the predominant derivatives of hydroxycinnamic acids were found to be chlorogenic acid (76%) and the glucosides (84%) respectively. The variations in the ratio of Benedict-reactive (chlorogenic acid) and non-reactive compounds (mainly caffeic acid glucoside) are discussed in relation to their possible role in the regulation of fruit growth and maturation.     

Interactions of lipoic acid radical cations with vitamins C and E analogue and hydroxycinnamic acid derivatives

As a powerful natural antioxidant, lipoic acid exerts significant antioxidant activities in vivo and in vitro by deactivation of reactive oxygen and nitrogen species. In this study we present a novel synergistic interaction of lipoic acid with other endogenous or exogenous antioxidants. Antioxidants vitamins C and E analogue (Trolox C) and hydroxycinnamic acid derivatives were found to recycle lipoic acid by donating electrons to lipoic acid radical cations, thereby increasing the antioxidant capacity of lipoic acid in vivo and in vitro. The rate constant of the electron transfer is in the order 10(9)dm(3)mol(-1)s(-1), close to the diffusion-controlled limit, and transfer quantum yield is above 95%.     

Elevated tyrosine decarboxylase and tyramine hydroxycinnamoyltransferase levels increase wound-induced tyramine-derived hydroxycinnamic acid amide accumulation in transgenic tobacco leaves

Feruloyltyramine (FT) and 4-coumaroyltyramine (4CT) participate in the defense of plants against pathogens through their extracellular peroxidative polymerization, which is thought to reduce cell wall digestibility. Hydroxycinnamoyl-CoA:tyramine N-(hydroxycinnamoyl)transferase (THT; EC 2.3.1.110) and tyrosine decarboxylase (TYDC; EC 4.1.1.25) are purported to play key roles in the stress-induced regulation of tyramine-derived hydroxycinnamic acid amide (HCAAT) metabolism. Transgenic tobacco (Nicotiana tabacum cv. Xanthi) was engineered to constitutively express tobacco THT. A T₁ plant over-expressing THT was crossbred with T₁ tobacco expressing opium poppy TYDC2, to produce a T₂ line with elevated THT and TYDC activities compared with wild type plants. The effects of an independent increase in TYDC or THT activity, or a dual increase in both TYDC and THT on the cellular pools of HCAAT pathway intermediates and the accumulation of soluble and cell wall-bound FT and 4CT were examined. Increased TYDC activity resulted in a larger cellular pool of tyramine and lower levels of L-phenylalanine in transgenic leaves. In contrast, elevated THT activity reduced tyramine levels. HCAAT levels were low in healthy leaves, but were induced in response to wounding and accumulated around wound sites. Similarly, endogenous THT and TYDC activities were wound-induced. The rate of wound-induced HCAAT accumulation was highest in transgenic plants with elevated THT and TYDC activities showing that both enzymes exert control over the flux of intermediates involved in HCAAT biosynthesis under some conditions.     

Hydroxycinnamoylputrescines are not causally involved in the tuberization process in potato plants

The possible role of hydroxycinnamoylputrescines in the tuberization process of potato plants was studied using in vitro tuberization systems. Minitubers in shoot cultures of Solanum tuberosum ssp. andigena and S. tuberosum ssp. tuberosum were obtained in vitro within 3 weeks of dark incubation after increasing the sucrose concentration in the Murashige-Skoog (T. Murashige and F. Skoog. 1962. Physiol. Plant. 15: 473–497.) medium (without hormones) from 60 to 240 m M . both in the presence and absence of benzylaminopurine (BAP). Feruloylputrescine (FP) and caffeoylputrescine (CP) increased with tuberization, with a sharp maximum at day 9 in the shoot, but only when the medium contained BAP. When inhibitors of phenylalanine ammonia-lyase (PAL) and of polyamine biosynthesis were added to the medium containing BAP, the levels of FP and CP were reduced to values lower than those observed in the absence of BAP, but there was no significant effect on the number and dry weight of tubers formed. Addition of BAP without increasing the sucrose content also resulted in CP and FP accumulation. but failed to induce tuberization of the cultures. Experiments with in vitro stolon cultures and leaf cuttings also supported the conclusion that CP and FP accumulated as a response to the application of BAP, without having any effect on optimal tuberization. These results indicate that the increase of hydroxycinnamoylputrescines during tuber formation is unlikely to be causally involved in the tuberization process in potato plants.