Stigmastanol

The Molecular Profile of Soil Microbial Communities Inhabiting a Cambrian Host Rock.[Pubmed:38543564]

Microorganisms. 2024 Mar 2;12(3):513.

The process of soil genesis unfolds as pioneering microbial communities colonize mineral substrates, enriching them with biomolecules released from bedrock. The resultant intricate surface units emerge from a complex interplay among microbiota and plant communities. Under these conditions, host rocks undergo initial weathering through microbial activity, rendering them far from pristine and challenging the quest for biomarkers in ancient sedimentary rocks. In addressing this challenge, a comprehensive analysis utilizing Gas Chromatography Mass Spectrometry (GC-MS) and Time-of-Flight Secondary Ion Mass Spectrometry (ToF-SIMS) was conducted on a 520-Ma-old Cambrian rock. This investigation revealed a diverse molecular assemblage with comprising alkanols, sterols, fatty acids, glycerolipids, wax esters, and nitrogen-bearing compounds. Notably, elevated levels of bacterial C(16), C(18) and C(14) fatty acids, iso and anteiso methyl-branched fatty acids, as well as fungal sterols, long-chained fatty acids, and alcohols, consistently align with a consortium of bacteria and fungi accessing complex organic matter within a soil-type ecosystem. The prominence of bacterial and fungal lipids alongside maturity indicators denotes derivation from heterotrophic activity rather than ancient preservation or marine sources. Moreover, the identification of long-chain (>C22) n-alkanols, even-carbon-numbered long chain (>C20) fatty acids, and campesterol, as well as Stigmastanol, provides confirmation of plant residue inputs. Furthermore, findings highlight the ability of contemporary soil microbiota to inhabit rocky substrates actively, requiring strict contamination controls when evaluating ancient molecular biosignatures or extraterrestrial materials collected.

Supercritical CO(2) Extraction of Triterpenoids from Chaga Sterile Conk of Inonotus obliquus.[Pubmed:35335249]

Molecules. 2022 Mar 14;27(6):1880.

Triterpenoids are among the bioactive components of Chaga, the sterile conk of the medicinal fungus Inonotus obliquus. Supercritical fluid extraction of Chaga triterpenoids was carried out with supercritical CO(2), while a modified Folch method was used as a comparison. Three temperature-pressure combinations were tested varying between 314-324 K (40-50 degrees C) and 281-350 bars, using time- and volume-limited extractions. Six triterpenoids were identified with GC-MS and quantified with GC-FID: ergosterol, lanosterol, beta-sitosterol, Stigmastanol, betulin, and inotodiol. The Folch extraction resulted in recovery of trametenolic acid, which was not extracted by supercritical CO(2). Inotodiol was the major triterpenoid of all the extracts, with a yield of 87-101 mg/100 g and 139 mg/100 g, for SFEs and the Folch method, respectively. The contents of other major triterpenoids, lanosterol and ergosterol, varied in the ranges 59-63 mg/100 g and 17-18 mg/100 g by SFE, respectively. With the Folch method, the yields were 81 mg/100 g and 40 mg/100 g, respectively. The highest recovery of triterpenoids with SFE in relation to Folch was 56% and it was obtained at 324 K (50 degrees C) and 350 bar, regardless of extraction time or volume of CO(2). The recoveries of lanosterol and Stigmastanol were unaffected by SFE conditions. Despite the lower yield, SFE showed several advantages including shorter extraction time and less impact on the environment. This work could be a starting point for further studies on green extraction methods of bioactive triterpenoids from Chaga.

Microwave and Ultrasound Pretreatment of Moringa oleifera Lam. Seeds: Effects on Oil Expression, Oil Quality, and Bioactive Component.[Pubmed:34121028]

J Oleo Sci. 2021 Jul 1;70(7):875-884.

This study investigates the application of green technologies (microwave and ultrasound pretreatment) in the extraction of Moringa oleifera Lam. seed oil and its effects on oil expression, oil quality, and bioactive component. Moringa seeds were pretreated with microwave (90 W, 60 s) or ultrasound (50 W, 1 h) before mechanical expression. A separate group received no pretreatment before oil extraction. Oils from these groups were then compared. Results show that oil yield increased with ultrasound pretreatment (1.24%) and significantly increased with microwave pretreatment (3.11%). For oil flow rate, the microwave and ultrasound pretreatment resulted in faster extraction (7.67 and 6.93 kg/h respectively) as compared with the control (6.51 kg/h). For physicochemical parameters, the microwave and ultrasound group had significantly less free fatty acids and significantly greater unsaponifiable matter as compared with the control. For fatty acid composition, results show that moringa seeds procured from Davao Oriental had greater oleic acid content (~77%) as compared with those reported by other literature. For phytosterol content, the predominant phytosterols found were beta-sitosterol, stigmasterol, and campesterol. Microwave and ultrasound pretreatment significantly increased total phytosterol (680.58 and 369.32 mg/kg respectively) as compared with the control (72.69 mg/kg) due to the mass transfer of the phytosterols. Microwave and ultrasound pretreatment also led to Stigmastanol formation. For antioxidant activity, a comparison of both DPPH and FRAP assays depicts that the microwave group exhibited the best overall antioxidant activity. Lastly, for oil stability, a lower peroxide value was found in the microwave and ultrasound groups across time intervals, which may be attributed to their antioxidant activity. In summary, ultrasound and microwave pretreatment can improve oil expression, oil quality, and bioactive content of the mechanically expressed moringa oils.

Acaricidal efficacy and chemical study of hexane extracts of the leaves of Neoglaziovia variegata (Bromeliaceae) against the tick Rhipicephalus microplus.[Pubmed:33860415]

Exp Appl Acarol. 2021 May;84(1):263-270.

The frequent use of acaricides against the tick Rhipicephalus microplus increases the risk of development of resistance. Recent studies have revealed that Neoglaziovia variegata, an indigenous plant species known in Brazil as 'caroa', has a deleterious effect against R. microplus. In the current study, extracts of N. variegata were studied for their possible acaricidal properties. A hexane extract of N. variegata leaves was fractionated in a chromatography column and the fractions were tested in adult tick immersion tests in triplicate using three concentrations (5, 10 and 25 mg/ml). All the fractions had harmful effects on the ticks. However, three fractions were more efficaceous. Phytochemical analysis indicated that stigmast-5-en-3-ol and Stigmastanol were most abundant; they might be responsible for the acaricidal effects, making them potentially useful as alternative agents to control the tick R. microplus.

An extensive study on the chemical diversity of lipophilic extractives from Eucalyptus globulus wood.[Pubmed:32971340]

Phytochemistry. 2020 Dec;180:112520.

Three mature Eucalyptus globulus trees with 40 years of age were studied at three height levels (0%, 35%, and 60% of total tree height) and at three radial regions (sapwood, inner and outer heartwood). The composition of lipophilic extracts was evaluated and an extensive list of 202 compounds was reported for the first time. The fatty acids were the major chemical family, representing 40.8% of the total compounds, followed by phytosterols (19.0%), aromatics (10.5%) and triterpenes (10.4%). Saturated fatty acids accounted for 74.2% of total compounds (C(16:0), C(24:0) and C(26:0) were predominant), beta-Sitosterol and Stigmastanol were the main sterols (80 and 7% respectively), while aromatics were mainly represented by syringic acid, 4-hydroxy-3,5-dimethoxybenzaldehyde, vanillic acid, and vanillin. The main triterpenes were asiatic and arjunolic acids.

Effect of Moringa oleifera L. Leaf Powder Addition on the Phenolic Bioaccessibility and on In Vitro Starch Digestibility of Durum Wheat Fresh Pasta.[Pubmed:32422925]

Foods. 2020 May 14;9(5):628.

Fresh pasta was formulated by replacing wheat semolina with 0, 5, 10, and 15 g/100 g (w/w) of Moringa oleifera L. leaf powder (MOLP). The samples (i.e., M0, M5, M10, and M15 as a function of the substitution level) were cooked by boiling. The changes in the phenolic bioaccessibility and the in vitro starch digestibility were considered. On the cooked-to-optimum samples, by means of ultra-high-performance liquid chromatography-quadrupole time-of-flight (UHPLC-QTOF) mass spectrometry, 152 polyphenols were putatively annotated with the greatest content recorded for M15 pasta, being 2.19 mg/g dry matter (p < 0.05). Multivariate statistics showed that Stigmastanol ferulate (VIP score = 1.22) followed by isomeric forms of kaempferol (VIP scores = 1.19) and other phenolic acids (i.e., schottenol/sitosterol ferulate and 24-methylcholestanol ferulate) were the most affected compounds through the in vitro static digestion process. The inclusion of different levels of MOLP in the recipe increased the slowly digestible starch fractions and decreased the rapidly digestible starch fractions and the starch hydrolysis index of the cooked-to-optimum samples. The present results showed that MOLP could be considered a promising ingredient in fresh pasta formulation.

The characterization of soybean germ oil and the antioxidative activity of its phytosterols.[Pubmed:35541380]

RSC Adv. 2019 Dec 4;9(68):40109-40117.

The aim of this study was to characterize the composition of soybean germ and its oil from Northeast (NE-SG) and Shandong Province (SD-SG) of China with a focus on the composition of fatty acids and phytosterols as well as physicochemical properties. The results show that the average contents of water, protein, crude fat, crude fiber and ash of NE-SG and SD-SG were 8.23 +/- 0.11%, 40.47 +/- 0.10%, 11.65 +/- 0.14%, 6.20 +/- 0.09% and 4.79 +/- 0.14%, respectively. The major fatty acids of the two soybean germ oils were linoleic acid (NE-SGO, 55.45%; SD-SGO, 52.15%), alpha-linolenic acid (NE-SGO, 16.21%; SD-SGO, 18.50%), palmitic acid (NE-SGO, 12.59%; SD-SGO, 11.40%) and oleic acid (NE-SGO, 9.87%; SD-SGO, 10.96%). The soybean germs were rich in phytosterols (NE-SGO, 3168 mg/100 g oil; SD-SGO, 3010 mg/100 g oil) consisting of beta-sitosterol, Delta7-stigmastenol, campesterol, Stigmastanol, and citrostadienol. The antioxidant ability of soybean germ phytosterols was evaluated using DPPH and OH radical scavenging assays, beta-carotene protection assay and a heating oil system. The results demonstrated that soybean germ phytosterols had better antioxidant ability in oil systems than in non-oil systems. The antioxidant ability of these phytosterols was temperature- and time-dependent since it was more effective at lower temperatures (60 degrees C) with longer times as compared to higher temperatures (120 degrees C and 180 degrees C) with shorter times. These results prove that soybean germ phytosterols could be used as antioxidants in preventing lipid oxidation in foods stored at a low temperature for a long time.

Metabolomics and transcriptomics reveal defense mechanism of rice (Oryza sativa) grains under stress of 2,2',4,4'-tetrabromodiphenyl ether.[Pubmed:31521816]

Environ Int. 2019 Dec;133(Pt A):105154.

2,2',4,4'-Tetrabromodiphenyl ether (BDE-47), a predominant polybrominated diphenyl ether (PBDE), has received extensive attention for its potential environmental impact. An integrated study of metabolomics and transcriptomics was conducted on two rice (Oryza sativa) cultivars, Lianjing-7 (LJ-7) and Yongyou-9 (YY-9), which have been identified as tolerant and sensitive cultivars to BDE-47, respectively. The objective was to investigate the molecular mechanisms of their different ability to tolerate BDE-47. Both rice plants were cultivated to maturity in soils containing three concentrations of BDE-47 (10, 20, and 50 mg/kg). Metabolomic analyses of rice grains identified 65 metabolites in LJ-7 and 45 metabolites in YY-9, including amino acids, saccharides, organic acids, fatty acids, and secondary metabolites. In the tolerant cultivar LJ-7 exposed to 50 mg/kg BDE-47, concentrations of most of the metabolites increased significantly, with alpha-ketoglutaric acid increased by 20-fold and Stigmastanol increased by 12-fold. In the sensitive cultivar YY-9, the concentrations of most metabolites increased after the plant was exposed to 1 and 10 mg/kg BDE-47 but decreased after the plant was exposed to 50 mg/kg BDE-47. Transcriptomic data demonstrated that regulation of gene expressions was affected most in LJ-7 exposed to 50 mg/kg BDE-47 (966 genes up-regulated and 620 genes down-regulated) and in YY-9 exposed to 10 mg/kg BDE-47 (85 genes up-regulated and 291 genes down-regulated), in good accordance with the observed metabolic alternation in the two cultivars. Analyses of metabolic pathways and KEGG enrichment revealed that many biological processes, including energy consumption and biosynthesis, were perturbed in the two rice cultivars by BDE-47. A majority of metabolites and genes involved in dominating pathways of energy consumption (e.g., tricarboxylic acid cycle) and the biosynthesis (e.g., metabolism of saccharides and amino acids) were enhanced in LJ-7 by BDE-47. In contrast, energy consumption was increased while biosynthetic processes were inhibited in YY-9 by BDE-47, which could lead to the sensitivity of YY-9 to BDE-47. The combined results suggest that the different defensive abilities of these two rice cultivars in response to BDE-47 could be attributed to their differences in energy-consumption strategy and biosynthesis of nutritional components in grains. This study provides a useful reference for rice cultivation in PBDE-polluted areas.

Identification of Antidiabetic Metabolites from Paederia foetida L. Twigs by Gas Chromatography-Mass Spectrometry-Based Metabolomics and Molecular Docking Study.[Pubmed:31275982]

Biomed Res Int. 2019 May 29;2019:7603125.

Paederia foetida L. (Rubiaceae) is a climber which is widely distributed in Asian countries including Malaysia. The plant is traditionally used to treat various diseases including diabetes. This study is to evaluate the enzymatic inhibition activity of Paederia foetida twigs extracts and to identify the metabolites responsible for the bioactivity by gas chromatography-mass spectrometry (GC-MS) metabolomics profiling. Three different twig extracts, namely, hexane (PFH), chloroform (PFC), and methanol (PFM), were submerged for their alpha-amylase and alpha-glucosidase inhibition potential in 5 replicates for each. Results obtained from the loading column scatter plot of orthogonal partial least square (OPLS) model revealed the presence of 12 bioactive compounds, namely, dl-alpha-tocopherol, n-hexadecanoic acid, 2-hexyl-1-decanol, Stigmastanol, 2-nonadecanone, cholest-8(14)-en-3-ol, 4,4-dimethyl-, (3beta,5alpha)-, stigmast-4-en-3-one, stigmasterol, 1-ethyl-1-tetradecyloxy-1-silacyclohexane, ɣ-sitosterol, stigmast-7-en-3-ol, (3beta,5alpha,24S)-, and alpha-monostearin. In silico molecular docking was carried out using the crystal structure alpha-amylase (PDB ID: 4W93) and alpha-glucosidase (PDB ID: 3WY1). alpha-Amylase-n-hexadecanoic acid exhibited the lowest binding energy of -2.28 kcal/mol with two hydrogen bonds residue, namely, LYS178 and TYR174, along with hydrophobic interactions involving PRO140, TRP134, SER132, ASP135, and LYS172. The binding interactions of alpha-glucosidase-n-hexadecanoic acid complex ligand also showed the lowest binding energy among 5 major compounds with the energy value of -4.04 kcal/mol. The complex consists of one hydrogen bond interacting residue, ARG437, and hydrophobic interactions with ALA444, ASP141, GLN438, GLU432, GLY374, LEU373, LEU433, LYS352, PRO347, THR445, HIS348, and PRO351. The study provides informative data on the potential antidiabetic inhibitors identified in Paederia foetida twigs, indicating the plant has the therapeutic effect properties to manage diabetes.

Sewage contamination of Amazon streams crossing Manaus (Brazil) by sterol biomarkers.[Pubmed:30390455]

Environ Pollut. 2019 Jan;244:818-826.

Sewage pollution is a principal factor of decreasing water quality, although it has not been considered a real impact in Amazonia that is still considered a pristine environment around the world. Thus, this study aimed to assess the levels of sewage contamination in sediments from three streams crossing Manaus - a Brazilian city of 2,403,796 inhabitants in the heart of the Amazon rain forest. Cholesterol, cholestanol, brassicasterol, ergosterol, stigmasterol, beta-sitosterol, campesterol, Stigmastanol, coprostanol, and epicoprostanol levels were determined by liquid chromatography tandem mass spectrometry (LC-MS/MS). The fecal indicator, coprostanol, was found in high concentrations (509-12 830 ng g(-1)) and high relative proportions (21-54%) in all samples collected in the Mindu stream that crosses many heavily populated districts of the city, and in the Quarenta stream that crosses the Industrial District of Manaus. The sediments of the Taruma-Acu stream also presented coprostanol; however, concentrations (