Mangifera indica as propolis source: what exactly do bees collect?

Objective The mango tree Mangifera indica is known as one of the botanical sources of propolis in Tropical regions. There are two different materials which bees can collect from a mango tree to produce propolis: the resin of the tree bark, and the latex found on the fruits. We performed the study of the chemical profile of mango resin in comparison with propolis in order to clarify its importance as propolis source. Results We compared the chemical profiles (by GC–MS analysis of ethanol extracts after silylation) of the resin and samples of propolis: of stingless bees (3 Vietnames, 2 Indonesian), and one of Apis mellifera from Thailand. In the resin and all propolis samples, 25 compounds were identified: fatty acids, cardanols (alk(en)yl phenols), cardols, anacardic acids, triterpene alcohols and ketones, cycloartane type triterpenic acids. All samples have the same qualitative composition but there are important quantitative differences. Considering literature data on mango latex, we conclude that bees of different species, make use of the two propolis sources offered by mango: bark resin and fruit latex, in different proportions. We also confirmed for the first time the presence of alk(en)yl phenols and anacardic acids in the tree bark resin of mango.

Mangifera indica as propolis source: what exactly do bees collect?

Objective The mango tree Mangifera indica is known as one of the botanical sources of propolis in Tropical regions. There are two different materials which bees can collect from a mango tree to produce propolis: the resin of the tree bark, and the latex found on the fruits. We performed the study of the chemical profile of mango resin in comparison with propolis in order to clarify its importance as propolis source. Results We compared the chemical profiles (by GC-MS analysis of ethanol extracts after silylation) of the resin and samples of propolis: of stingless bees (3 Vietnames, 2 Indonesian), and one of Apis mellifera from Thailand. In the resin and all propolis samples, 25 compounds were identified: fatty acids, cardanols (alk(en)yl phenols), cardols, anacardic acids, triterpene alcohols and ketones, cycloartane type triterpenic acids. All samples have the same qualitative composition but there are important quantitative differences. Considering literature data on mango latex, we conclude that bees of different species, make use of the two propolis sources offered by mango: bark resin and fruit latex, in different proportions. We also confirmed for the first time the presence of alk(en)yl phenols and anacardic acids in the tree bark resin of mango.

Gamma-oryzanol reduces renal inflammation and oxidative stress by modulating AGEs/RAGE axis in animals submitted to high sugar-fat diet

Introduction: The receptor for AGEs (RAGE) is a multiligand member of the immunoglobulin superfamily of cell surface receptors expressed in many organs, among them, the kidneys. When activated, RAGE leads to a sequence of signaling that results in inflammation and oxidative stress, both involved in kidney disease pathogenesis. Gamma-oryzanol (γOz) comprises a mixture of ferulic acid (FA) esters and phytosterols (sterols and triterpene alcohols) mainly found in rice, with antioxidant and anti-inflammatory activities. Aim: To evaluate the effect of γOz to reduce renal inflammation and oxidative stress by modulating AGEs/RAGE axis in animals submitted to a high sugar-fat diet. Methods: Male Wistar rats (±187g) were randomly divided into two experimental groups: control (n = 7 animals) and high sugar-fat diet (HSF, n = 14 animals) for 20 weeks. After this period, when the presence of renal disease risk factors was detected in the HSF group (insulin resistance, dyslipidemia, increased systolic blood pressure and obesity), the HSF animals were divided to begin the treatment with γOz or continue receiving only HSF for 10 more weeks. Results: No effect of γOz on obesity and metabolic parameters was observed. However, kidney inflammation and oxidative stress decreased as soon as RAGE levels were reduced in HSF + γOz. Conclusion: It is possible to conclude that the gamma- oryzanol was effective in reducing inflammation and oxidative stress in the kidney by modulating the AGEs/RAGE axis.

Hydrocarbons and Ethers of Extractive Substances of Siberian Larch Needles

Siberian larch (Larix sibirica L.) is the main commercial species in Russia. Currently, larch woody greens are underutilized. They are considered a waste product from logging. This is due to the lack of knowledge on the composition of compounds and the variability of the raw material source itself as a result of the fall of the needles. The research purpose is to study the composition of hydrocarbons and esters from Siberian larch needles in summer and autumn collection from the Tomsk region. The shredded needles were extracted with propan-2-ol; then, after distillation of the solvent, substances soluble in petroleum ether (PE, 40–70 °С) were isolated. The latter were divided into free acids (31.5 % for green needles and 28.0 % for yellow needles) and neutral substances (59.8 and 48.1 %, respectively). Then, eutral substances were chromatographed on silica gel: hydrocarbons (2.43 and 3.02 %, hereinafter from neutral substances of green and yellow needles, respectively), esters (31.30 and 33.80 %) and triglycerides (11.70 % and 6.44 %). The ester and triglyceride fractions were exposed to alkaline hydrolysis and the acidic components of esters (9.12 and 24.80 %) and triacylglycerols (17.43 and 26.15 %) were produced. Fractions of unsaponifiable compounds, in addition to alcohols, contained unsaponifiables with unchanged Rf values on thin-layer chromatography (TLC). Fractions of unsaponifiables were chromatographed on silica gel, and then the isolated fractions were additionally chromatographed on silica gel with silver nitrate. The isolated compounds were identified by nuclear magnetic resonance (NMR) spectroscopy. In the acidic component of esters, the main components are linoleic and linolenic acids. Hydrocarbons are represented by sesquiterpenes in both collections of needles. A new aromatic hydrocarbon for coniferous plants, geranyl-p-cymene, has been identified. For the first time, polyprenols were isolated from Siberian larch greens, the structure of which differs from spruce and pine polyprenols by chain length according to NMR spectroscopy and mass spectrometry data. They contain from 14 to 20 isoprene links in the chain of molecules with predominance of prenol-17. The yield of polyprenols was 12.8–14.9 % of neutral substances of yellow and green needles, respectively. Tetracyclic triterpene alcohols and sterols were isolated from green needles. Triterpene alcohols were not found in yellow needles. For citation: Mikson D.S., Roshchin V.I. Hydrocarbons and Ethers of Extractive Substances of Siberian Larch Needles. Lesnoy Zhurnal [Russian Forestry Journal], 2021, no. 3, pp. 170–185. DOI: 10.37482/0536-1036-2021-3-170-185

Results of a comparative study of Nigella Sativa L. Seeds oils composition

This article presents results of the chemical composition study of the seeds oils lipid complex of Nigella Sativa L. grown under various geographic conditions. The task of the comprehensive study of the chemical composition of the plant and its individual parts remains relevant due to the wide spectrum of its pharmacological activity.The aim of this work is a comparative study of the fatty acid composition, a non-saponifiable fraction and the composition of essential oils of Nigella Sativa L. seeds grown in different regions of the world.Materials and methods. The combination of chromatography-mass spectrometry and 1H-NMR spectroscopy methods made it possible to study the qualitative and quantitative composition of Nigella Sativa L. lipid complex seeds. All the experiments were carried out in accordance with the requirements of the State Pharmacopoeia, 14th Ed, given in the corresponding general pharmacopeial monographs.Results. Profiles have been established and the content of fatty acids, sterines, triterpene alcohols, essential oils and thymoquinone found out in the lipid complex, has been estimated. The saponifiable portion of the complex is represented by triglycerides (81.7–95.3%), di(3.9–15.2%) and monoglycerides (0.7–4.1%). They mainly contain linoleic (55.8–60.6%), oleic (21.8–24.6%), palmitic (10.0–12.8%), stearic (2.4–3.2 %) and cis-11.14-eicosadiene (2.3–2.6%) acids. In the lipid complex, the contents of sterines and triterpene alcohols were 0.4–0.7%; up to 70% of the fraction was represented by β-sitosterol (22.5–29.2%), cycloartenol (20.1–36.6%) and 24 methylenecycloartanol (9.5–19.9%). In the trace amounts (up to 1.0%), cholesterol has been detected in all the samples. In the lipid complexes, the content of thymoquinone ranged from 0.7 to 2.6%.Conclusion. A comparative study of the seeds lipid complex of Nigella Sativa L. grown under various geographic conditions, has been carried out. The marker compounds as well as their content standards for determining the authenticity of raw materials (thymoquinone, para-cimen, cis-11.14-eicosadienic acid), have been identified.

QUALITY AND QUANTITATIVE COMPOSITION OF SUNFLOWER OIL DEODORIZATION DISTILLATE

The composition of the sunflower oil deodorization distillate has been investigated. 18 acidic components have been identified, more than 40% of the composition of the studied sample falls on linoleic acid with F-vitamin activity. More than 30 components of neutral nature have been found that are of interest as bioactive compounds. Of these, 10 are phytosterols, 14 are triterpene alcohols, 5 are tocopherols. The diterpene hydrocarbons, alcohols and acids of the kauran structure found in the composition of deodorization distillate indicate that the original sunflower oil was native, since it is known that kauran derivatives are a chemotaxonomic marker of many plants of the compositae family, including sunflower. In addition to the above compounds, hydrocarbons (more than a quarter of the unsaponifiable matter), both aliphatic and diterpenic, in the studied sample, was found. Aliphatic components are predominantly unsaturated, which may indicate their artifact origin, i.e. they are the products of the dehydration of aliphatic alcohols. Phytadiene isomers, products of phytol dehydration and isomerization, have been found. The data obtained indicate the prospects for the use of oil deodorization distillate as a source of bioactive substances, cosmetic ingredients and pharmaceutical components.

BIOACTIVE COMPONENTS OF ETHEREAL EXTRACT OF WOOD GREENING SEA BUCKTHORN HIPPOPHAE RHAMNOIDES L.

The composition of lipophilic components of sea buckthorn leafy shoots, a large tonnage waste in the production of sea buckthorn oil and during renewing the cultural plantings of sea buckthorn, was studied. Tert-butyl methyl ether (TBME) was used as an extraction solvent for raw materials having all the advantages of diethyl ether, but devoid of its disadvantages. It does not form peroxides and does not create increased gas content due to the higher boiling point. The chemical composition of the TBME extract of sea buckthorn leafy shoots was studied by gas chromatography–mass-spectrometry and high-performance liquid chromatography. Seventy-four neutral and thirty-eight acidic components, including polyprenols, dolichols, triterpene alcohols and acids, sterols, were identified. TBME as an extragent provides more high yields of bioactive triterpenoic acids and diols including uvaol, eritrodiol and betulin in comparison with n-hexane. These compounds can increase some useful properties of obtained extract.

Alkaline hydrolysis of wool fat (lanolin) in a medium of proton and aprotic solvents

The raw material being studied is the woolen fat of the sheep of the Edilbay fine-fleece and Kazakh arkharomeric fine-fleece, which is excreted when washing wool in primary wool processing plants (PWP) in the regions of Kazakhstan, such as Semipalatinsk, Aktyubinsk, Zhambyl and Tokmak. Earlier we obtained anhydrous lanolin from the fat of various factories of the PWP. In both cases, positive results were obtained and a certificate of compliance of anhydrous lanolin FS RK was obtained. In terms of its chemical composition, wool fat is a mixture of C10-C16 carboxylic acid esters with aliphatic, terpenic, triterpene and sterol alcohols. It also contains vitamins, proteins, sterols and other physiologically active compounds. In the hydrolysis of wool fat, a mixture of sterol alcohols, triterpene alcohols and fatty acid salts are assumed. Valuable among them are sterol alcohols, which constitute up to 29% of the sum of all alcohols. Cholesterol and its derivatives are the raw materials for the synthesis of steroid drugs. Salts of fatty acids are used as an emulsifier in pharmacy and cosmetology. The aim of this paper is to complete the saponification of wool fat and the separation of a mixture of sterol alcohols. We show the patterns of alkaline hydrolysis of wool fat in the liquid phase in the presence of mixtures of various solvents. As a solvent, the ethanol-water, isopropanol-water system in which wool fat is only partially dissolved has been studied. In the wool fat-alcohol-water-NaOH system, a stable emulsion is formed. Ways that prevent the formation of an emulsion are proposed.