Evaluation of the Physico-Chemical Properties of Liposomes Assembled from Bioconjugates of Anisic Acid with Phosphatidylcholine

The aim of this work was the evaluation of the physico-chemical properties of a new type of liposomes that are composed of DPPC and bioconjugates of anisic acid with phosphatidylcholine. In particular, the impact of modified anisic acid phospholipids on the thermotropic parameters of liposomes was determined, which is crucial for using them as potential carriers of active substances in cancer therapies. Their properties were determined using three biophysical methods, namely differential scanning calorimetry (DSC), steady-state fluorimetry and attenuated total reflectance Fourier transform infrared spectroscopy (ATR-FTIR). Moreover, temperature studies of liposomes composed of DPPC and bioconjugates of anisic acid with phosphatidylcholine provided information about the phase transition, fluidity regarding chain order, hydration and dynamics. The DSC results show that the main phase transition peak for conjugates of anisic acid with phosphatidylcholine molecules was broadened and shifted to a lower temperature in a concentration- and structure-dependent manner. The ATR-FTIR results and the results of measurements conducted using fluorescent probes located at different regions in the lipid bilayer are in line with DSC. The results show that the new bioconjugates with phosphatidylcholine have a significant impact on the physico-chemical properties of a membrane and cause a decrease in the temperature of the main phase transition. The consequence of this is greater fluidity of the lipid bilayer.

Effect of Seasonal Decrease in Temperature on the Content and Composition of Guayulins in Stems of Guayule (Parthenium argentatum, Gray)

The guayulins are a family of sesquiterpene compounds that consist of an isoprenoid nucleus substituted either by trans-cinnamic or p-anisic acid, and are present only in the resinous fraction of the rubber plant guayule (Parthenium argentatum, Gray). While the natural role of the guayulins remains enigmatic, they may serve as a defense function against other plants or herbivores by virtue of the accumulation of cinnamic acid. Prior research has suggested seasonal variation in guayulin content, which has been shown to decrease as winter arrives in two different varieties. In the present study, the effect of guayulins has been evaluated in 13 different accessions cultivated under the same conditions during autumn. A general reduction in guayulin content was found in the stems from all varieties between the September and November harvest, which was accompanied by an increase in the resin content. With respect to individual guayulins, while guayulin A was the most prominent member during most of the year, guayulin C had more prominence when temperature started to decrease. In this seasonal period, the production of each member of the guayulin family in the leaves was very balanced.

Phytochemical Analysis and Biological Activities of the Ethanolic Extract of Daphne sericea Vahl Flowering Aerial Parts Collected in Central Italy

In this paper, the first phytochemical analysis of the ethanolic extract of Daphne sericea Vahl flowering aerial parts collected in Italy and its biological activities were reported. Eleven compounds were identified i.e., α-linolenic acid (1), tri-linoleoyl-sn-glycerol (2), pheophorbide a ethyl ester (3), pilloin (4), sinensetin (5), yuanhuanin (6), rutamontine (7), syringin (8), p-coumaric acid (9), p-anisic acid (10) and caffeic acid (11). To the best of our knowledge, compounds (1-4, 7-8 and 10) were isolated from D. sericea for the first time during this work, whereas sinensetin (5) represents a newly identified component of the entire Thymelaeaceae family. The extract was found to possess radical scavenging against both DPPH• and 2,2′-azino-bis(3-thylbenzothiazoline-6-sulfonic acid (ABTS•+) radicals, with at least a 40-fold higher potency against the latter. Moreover, chelating abilities against both ferrous and ferric ions have been highlighted, thus suggesting a possible indirect antioxidant power of the extract. Although the precise bioactive compounds remain to be discovered, the polyphenolic constituents, including phenolic acids, tannins and flavonoids, seem to contribute to the antioxidant power of the phytocomplex. In addition, the extract produced cytotoxic effects in MDA-MB-231 and U87-MG cancer cell lines, especially at the concentration of 625 μg/mL and after 48–72 h. Further studies are required to clarify the contribution of the identified compounds in the bioactivities of the extract and to support possible future applications.

Bioactive (Co)oligoesters as Potential Delivery Systems of p-Anisic Acid for Cosmetic Purposes

This article reports the studies on bioactive (co)oligoesters towards their use as controlled delivery systems of p-anisic acid. The objects of the study were oligo[3-hydroxy-3-(4-methoxybenzoyloxymethyl)propionate], (p-AA-CH2-HP)n oligoester, and oligo[(3-hydroxy-3-(4-methoxybenzoyloxymethyl)propionate)-co-(3-hydroxybutyrate)] [(p-AA-CH2-HP)x-co-(HB)y (co)oligoesters containing p-anisic acid moiety (p-AA, as the bioactive end and side groups) connected to the polymer backbone through the susceptible to hydrolysis ester bonds. A thorough insight into the hydrolysis process of the bioactive (co)oligoesters studied has allowed us to determine the release profile of p-AA as well as to identify polymer carrier degradation products. The p-AA release profiles determined on the basis of high-performance liquid chromatography (HPLC) measurements showed that the release of the bioactive compound from the developed (co)oligoester systems was regular and no burst effect occurred. Biological studies demonstrated that studied (homo)- and (co)oligoesters were well tolerated by HaCaT cells because none of them showed notable cytotoxicity. They promoted keratinocyte growth at moderate concentrations. Bioactive (co)oligoesters containing p-anisic acid moiety had somewhat decreased cell proliferation at the highest concentration (100 µg/mL). The important practical inference of the current study is that the (co)oligoesters developed have a relatively large load of the biologically active substance (p-AA) per polymer macromolecule, which unlocks their potential application in the cosmetic industry.

Lysophosphatidylcholine Containing Anisic Acid Is Able to Stimulate Insulin Secretion Targeting G Protein Coupled Receptors

Diabetes mellitus is a worldwide health problem with high rates of mortality and morbidity. Management of diabetes mellitus by dietary components is achievable especially at the initial stage of the disease. Several studies confirmed the antidiabetic activities of simple phenolic acids and lysophosphatidylcholine (LPC). The main goal of this study was to identify new potential insulin secretion modulators obtained by combining the structures of two natural compounds, namely O-methyl derivatives of phenolic acids and phospholipids. LPC and phosphatidylcholine bearing methoxylated aromatic carboxylic acids were tested as potential agents able to improve glucose-stimulated insulin secretion (GSIS) and intracellular calcium mobilization in MIN6 β pancreatic cell line. Our results show that LPC with covalently bonded molecule of p-anisic acid at the sn-1 position was able to induce GSIS and intracellular calcium flux. Notably, 1-anisoyl-2-hydroxy-sn-glycero-3-phosphocholine did not affect the viability of MIN6 cells, suggesting its potential safe use. Furthermore, we have shown that three G protein coupled receptors, namely GPR40, GPR55, and GPR119, are targeted by this LPC derivative.

Conformational equilibria in o-anisic acid and its monohydrated complex: the prevalence of the trans-COOH form

The prevalence of the trans-COOH form in a hydrated acid complex is shown for the first time in o-anisic acid.