A new 4alpha-methyl sterol, 4alpha-methyl-ergosta-6,8(14),22E-triene-3beta-ol (1), was isolated along with cholesterol from a Nephthea sp. Bornean soft coral The structure of compound 1 was elucidated on the basis of spectroscopic analysis and comparison of the data with those of the related compounds.
Kajian ini adalah mengenai peranan sterol sebagai penunjuk bio-lipid untuk mengenal pasti variasi dan sumber bahan organik yang hadir bersama sedimen permukaan dari Kuala Selangor, Selangor. Kajian melibatkan kaedah pengekstrakan sterol daripada sampel sedimen dan seterusnya dianalisis menggunakan GC-MS untuk menentukan kehadiran sebatian tersebut. Sepuluh sebatian sterol dikenal pasti hadir dengan fitosterol merupakan sebatian dominan di kawasan kajian iaitu 79% daripada jumlah keseluruhan sterol. Ini diikuti oleh kolesterol serta sterol kumbahan masing-masing menyumbangkan 6% daripada jumlah keseluruhan sterol manakala selebihnya berada dalam julat 1-5%. Indeks Sumber Sterol (SSI) juga menunjukkan kandungan fitosterol yang tinggi walaupun hadir pada kadar yang berbeza di setiap stesen pensampelan. Penilaian pencemaran kumbahan menggunakan nisbah koprostanol/kolesterol, koprostanol/(koprostanol+kholestanol) serta epikoprostanol/koprostanol menunjukkan kawasan kajian tidak mengalami pencemaran kumbahan walaupun sterol daripada sumber kumbahan hadir di persekitarannya. Kesimpulannya sedimen permukaan di Kuala Selangor, Selangor mengandungi campuran sterol daripada pelbagai sumber yang hadir di persekitarannya dengan didominasi oleh fitosterol yang berasal daripada tumbuhan terestrial.
Olive oil (OO) is widely recognized as a main component in the Mediterranean diet owing to its unique chemical composition and associated health-promoting properties. This review aimed at providing readers with recent results on OO physicochemical profiling, extraction technology, and quality parameters specified by regulations to ensure authentic products for consumers. Recent research progress on OO adulteration were outlined through a bibliometric analysis mapping using Vosviewer software. As revealed by bibliometric analysis, richness in terms of fatty acids, pigments, polar phenolic compounds, tocopherols, squalene, sterols, and triterpenic compounds justify OO health-promoting properties and increasing demand on its global consumption. OO storage is a critical post-processing operation that must be optimized to avoid oxidation. Owing to its great commercial value on markets, OO is a target to adulteration with other vegetable oils. In this context, different chemometric tools were developed to deal with this problem. To conclude, increasing demand and consumption of OO on the global market is justified by its unique composition. Challenges such as oxidation and adulteration stand out as the main issues affecting the OO market.
This study aims to determine the concentration of sterols used as biomarkers in the surface microlayer (SML) in estuarine areas of the Selangor River, Malaysia. Samples were collected during different seasons through the use of a rotation drum. The analysis of sterols was performed using gas chromatography equipped with a flame ionisation detector (GC-FID). The results showed that the concentrations of total sterols in the SML ranged from 107.06 to 505.55 ng L(-1). The total sterol concentration was found to be higher in the wet season. Cholesterol was found to be the most abundant sterols component in the SML. The diagnostic ratios of sterols show the influence of natural sources and waste on the contribution of sterols in the SML. Further analysis, using principal component analysis (PCA), showed distinct inputs of sterols derived from human activity (40.58%), terrigenous and plant inputs (22.59%) as well as phytoplankton and marine inputs (17.35%).
The Langat River in Malaysia has been experiencing anthropogenic input from urban, rural and industrial activities for many years. Sewage contamination, possibly originating from the greater than three million inhabitants of the Langat River Basin, were examined. Sediment samples from 22 stations (SL01-SL22) along the Langat River were collected, extracted and analysed by GC-MS. Six different sterols were identified and quantified. The highest sterol concentration was found at station SL02 (618.29 ng/g dry weight), which situated in the Balak River whereas the other sediment samples ranged between 11.60 and 446.52 ng/g dry weight. Sterol ratios were used to identify sources, occurrence and partitioning of faecal matter in sediments and majority of the ratios clearly demonstrated that sewage contamination was occurring at most stations in the Langat River. A multivariate statistical analysis was used in conjunction with a combination of biomarkers to better understand the data that clearly separated the compounds. Most sediments of the Langat River were found to contain low to mid-range sewage contamination with some containing 'significant' levels of contamination. This is the first report on sewage pollution in the Langat River based on a combination of biomarker and multivariate statistical approaches that will establish a new standard for sewage detection using faecal sterols.
Crude palm oil contains 600 to 1000 ppm of tocols in the form of tocopherols and tocotrienols. These palm tocols have been isolated and analyzed in the past by various chromatographic techniques such as open column chromatography, high-performance liquid chromatography, as well as thin-layer chromatography. Supercritical fluid chromatography (SFC) has emerged as a more advanced chromatographic technique in recent years. The tocols present in palm oil are successfully isolated using SFC. Identification of these tocols is supported by various spectroscopic techniques such as 1H NMR, 13C NMR, and mass spectrometry.
Faecal sterols detection is a promising method for identifying sources of faecal pollution. In this study, faecal contamination in water samples from point source (sewage treatment plants, chicken farms, quail farms and horse stables) was extracted using the solid phase extraction (SPE) technique. Faecal sterols (coprostanol, cholesterol, stigmasterol, beta-sitosterol and stigmastanol) were selected as parameters to differentiate the source of faecal pollution. The results indicated that coprostanol, cholesterol and beta-sitosterol were the most significant parameters that can be used as source tracers for faecal contamination. Chemometric techniques, such as cluster analysis, principal component analysis and discriminant analysis were applied to the data set on faecal contamination in water from various pollution sources in order to validate the faecal sterols' profiles. Cluster analysis generated three clusters: coprostanol was in cluster 1, cholesterol and beta-sitosterol formed cluster 2, while cluster 3 contained stigmasterol and stigmastanol. Discriminant analysis suggested that coprostanol, cholesterol and beta-sitosterol were the most significant parameters to discriminate between the faecal pollution source. The use of chemometric techniques provides useful and promising indicators in tracing the source of faecal contamination.
This study explores the role of sterols as lipid biomarkers to indicate their input which originates from various sources in the marine environment. Sterols and their ratios were investigated in sediments taken from sixteen sampling stations at Pulau Tinggi, Johor in order to assess the sources of organic matter. The compounds extracted from the sediments were quantified using a gas chromatography-mass spectrometry (GC-MS). The distributions of sterols indicated that organic matter at all sampling stations originated from a mixture of marine source and terrestrial origins at different proportions. A total of eleven sterols were quantified, with the major compounds being phytosterols (44% of total sterols), cholesterol (11%), brassicasterol (11%) and fecal sterols (12%).
A new antimalarial sterol, kaimanol (1), along with a known sterol, saringosterol (2) was isolated from the Indonesian Marine sponge, Xestospongia sp. The chemical structure of the new compound was determined on the basis of spectroscopic evidences and by comparison to those related compounds previously reported. Isolated compounds, 1 and 2 were evaluated for their antiplasmodial effect against Plasmodium falciparum 3D7 strains. Compounds 1 and 2 exhibited antiplasmodial activity with IC50 values of 359 and 0.250 nM, respectively.
Southeast Asia has undergone rapid developments in terms of urbanization, economic and population growth. The progress in sewerage treatment infrastructure has not kept pace with such developments. The inadequacy and inefficiency of sewerage systems has prompted the release of untreated sewage into the aquatic environment of Southeast Asia causing many waterborne illnesses since surface water is utilized for recreational, agricultural and aquaculture purposes and, above all, as a source of water intake in Southeast Asia. This paper will review the current data on molecular markers of sewage pollution including sterols and linear alkylbenzenes (LABs) in Southeast Asian aquatic environment to clarify the state of sewage pollution and the competence of sewage treatment plants (STPs) in this area. Despite the importance of sewage pollution research in the region, the number of studies using molecular markers to trace the sources of sewage pollution is limited. So far, indicators of sewage pollution have been investigated in aquatic environments of Indonesia, Vietnam, Malaysia, the Philippines, Thailand, Cambodia and Brunei among Southeast Asian countries. The concentrations and diagnostic ratios of faecal sterols and LABs show the release of untreated and primary treated urban waste into water bodies of these countries. Further studies are required to fill the data gaps in Southeast Asia and come to a better understanding of the trends of sewage pollution in this part of the world. Graphical abstract.
The oil of Adenanthera pavonina L. seeds was analysed by chromatographic and instrumental means. The oil was found to be rich in neutral lipids (86.2%), and low in polar lipids (13.8%). The neutral lipids consisted mainly of triacylglycerols (64.2%). Unsaturated fatty acids were found as high as 71%, while the percentage of saturated fatty acids was only 29%. GC and GC/MS analyses revealed linoleic, oleic and lignocerotic acid to be predominant among all fatty acids in the A. pavonina oil, whereas stigmasterol was the major steroid identified within this study. Subsequently, the oil was used for preparation of submicron oil-in-water (o/w) lipid emulsions. Lipid emulsions were formulated by using soybean lecithin (SL) to investigate their particle size, Zeta potential and stability at the different oil and SL ratios. The results obtained indicate possible applications of the tested oil in pharmaceutical and medical fields as drug and cosmetic active ingredient carriers.
Three strains of the chain-forming diatom Skeletonema marinoi, differing in their production of polyunsaturated aldehydes (PUA) and nutritional food components, were used in experiments on feeding, egg production, hatching success, pellet production, and behavior of three common planktonic copepods: Acartia tonsa, Pseudocalanus elongatus, and Temora longicornis. The three different diatom strains (9B, 1G, and 7J) induced widely different effects on Acartia tonsa physiology, and the 9B strain induced different effects for the three copepods. In contrast, different strains induced no or small alterations in the distribution, swimming behavior, and turning frequency of the copepods. 22:6(n-3) fatty acid (DHA) and sterol content of the diet typically showed a positive effect on either egg production (A. tonsa) or hatching success (P. elongatus), while other measured compounds (PUA, other long-chain polyunsaturated fatty acids) of the algae had no obvious effects. Our results demonstrate that differences between strains of a given diatom species can generate effects on copepod physiology, which are as large as those induced by different algae species or groups. This emphasizes the need to identify the specific characteristics of local diatoms together with the interacting effects of different mineral, biochemical, and toxic compounds and their potential implications on different copepod species.
Bioassay-guided isolation of the active hexane fractions of Curcuma zedoaria led to the identification of five pure compounds, namely, curzerenone (1), neocurdione (2), curdione (3), alismol (4), and zederone (5) and a mixture of sterols, namely, campesterol (6), stigmasterol (7), and β -sitosterol (8). Alismol has never been reported to be present in Curcuma zedoaria. All isolated compounds except (3) were evaluated for their cytotoxic activity against MCF-7, Ca Ski, and HCT-116 cancer cell lines and noncancer human fibroblast cell line (MRC-5) using neutral red cytotoxicity assay. Curzerenone and alismol significantly inhibited cell proliferation in human cancer cell lines MCF-7, Ca Ski, and HCT-116 in a dose-dependent manner. Cytological observations by an inverted phase contrast microscope and Hoechst 33342/PI dual-staining assay showed typical apoptotic morphology of cancer cells upon treatment with curzerenone and alismol. Both compounds induce apoptosis through the activation of caspase-3. It can thus be suggested that curzerenone and alismol are modulated by apoptosis via caspase-3 signalling pathway. The findings of the present study support the use of Curcuma zedoaria rhizomes in traditional medicine for the treatment of cancer-related diseases. Thus, two naturally occurring sesquiterpenoids, curzerenone and alismol, hold great promise for use in chemopreventive and chemotherapeutic strategies.
The molecular composition and distribution of sterols were investigated in the East China Sea to identify the origins of suspended particulate matter (SPM) in offshore waters influenced by Changjiang River Diluted Water (CRDW). Total sterol concentrations ranged from 3200 to 31,900pgL(-1) and 663 to 5690pgL(-1) in the particulate and dissolved phases, respectively. Marine sterols dominated representing 71% and 66% in the particulate and dissolved phases, respectively. Typical sewage markers, such as coprostanol, were usually absent at ~250km offshore. However, sterols from allochthonous terrestrial plants were still detected at these sites. A negative relationship was observed between salinity and concentrations of terrestrial sterols in SPM, suggesting that significant amounts of terrestrial particulate matter traveled long distance offshore in the East China Sea, and the Changjiang River Diluted Water (CRDW) was an effective carrier of land-derived particulate organic matter to the offshore East China Sea.
Near-shore surface sediment was collected from five stations off Redang Island located on the eastern coast of Peninsular Malaysia. Freeze-dried sediments were Soxhlet extracted and then fractionated using column chromatography into aliphatic and polar fractions. Determination of these fractions was carried out using gas chromatography mass spectrometry. The concentration of total resolved aliphatic hydrocarbons in sediments ranged from 157 to 308 ng/g. The distribution of aliphatic fraction showed the presence of n-alkanes ranging from nC15 to nC33 with a minor odd-to-even predominance exhibiting carbon maximum, depending on station, at nC17, nC26, nC29 or nC31. Calculation of Carbon Preference Index (CPI) for CPI(15-33) gave values ranging from 1.09 to 1.46. n-Alkanol in all sediment exhibits even-to-odd carbon predominance ranging from nC16 to nC28 and maximising at nC22. n-Fatty acids distribution ranged from nC14 to nC24 with a dominant maximum at nC16 and exhibiting high values of short chain fatty acids (≤nC20) to long chain fatty acids (>nC20) ratios. Unsaturated fatty acids, particularly nC16:1 and nC18:1 is also ubiquitous in all samples. Cholesterol is the most abundant compound amongst the sterol group ranging from 42.8 to 62.6% of the total sterols. β-Sitosterol, brassicasterol and stigmasterol, are also present but of relatively lower amount. These observations suggest that the aliphatic lipids and sterols in the study area originate, mainly, from biogenic sources of marine microbial with minor contribution from epiticular waxes of terrestrial plants.
The present study reports the composition and variation of fatty acids, sterols, tocopherols and γ-oryzanol among selected varieties namely Basmati Super, Basmati 515, Basmati 198, Basmati 385, Basmati 2000, Basmati 370, Basmati Pak, KSK-139, KS-282 and Irri-6 of Pakistani rice (Oryza sativa L). Oil content extracted with n-hexane from different varieties of brown rice seed (unpolished rice) ranged from 1.92% to 2.72%. Total fatty acid contents among rice varieties tested varied between 18240 and 25840 mg/kg brown rice seed. The rice tested mainly contained oleic (6841-10952 mg/kg) linoleic (5453-7874 mg/kg) and palmitic acid (3613-5489 mg/kg). The amounts of total phytosterols (GC and GC-MS analysis), with main contribution from β-sitosterol (445-656 mg/kg), campesterol (116-242 mg/kg), Δ(5)-avenasterol (89-178 mg/kg) and stigmasterol (75-180 mg/kg) were established to be 739.4 to 1330.4 mg/kg rice seed. The content of α-, γ- and δ-tocopherols as analyzed by HPLC varied from 39.0-76.1, 21.6-28.1 and 6.5-16.5 mg/kg rice seed, respectively. The amounts of different γ-oryzanol components (HPLC data), identified as cycloartenyl ferulate, 24-methylene cycloartanyl ferulate, campesteryl ferulate and β-sitosteryl ferulate, were in the range of 65.5-103.6, 140.2-183.1, 29.8-45.5 and 8.6-10.4 mg/kg rice seed, respectively. Overall, the concentration of these bioactives was higher in the Basmati rice cultivars showing their functional food superiority. In conclusion, the tested varieties of Pakistani rice, especially the Basmati cultivars, can provide best ingredients for functional foods.
Tinospora crispa (L.) Hook. f. & Thomson (Menispermaceae), found in the rainforests or mixed deciduous forests in Asia and Africa, is used in traditional medicines to treat numerous health conditions. This review summarizes the up-to-date reports about the ethnobotany, phytochemistry, pharmacological activities, toxicology, and clinical trials of the plant. It also provides critical assessment about the present knowledge of the plant which could contribute toward improving its prospect as a source of lead molecules for drug discovery. The plant has been used traditionally in the treatment of jaundice, rheumatism, urinary disorders, fever, malaria, diabetes, internal inflammation, fracture, scabies, hypertension, reducing thirst, increasing appetite, cooling down the body temperature, and maintaining good health. Phytochemical analyses of T. crispa revealed the presence of alkaloids, flavonoids, and flavone glycosides, triterpenes, diterpenes and diterpene glycosides, cis clerodane-type furanoditerpenoids, lactones, sterols, lignans, and nucleosides. Studies showed that the crude extracts and isolated compounds of T. crispa possessed a broad range of pharmacological activities such as anti-inflammatory, antioxidant, immunomodulatory, cytotoxic, antimalarial, cardioprotective, and anti-diabetic activities. Most pharmacological studies were based on crude extracts of the plant and the bioactive compounds responsible for the bioactivities have not been well identified. Further investigations are required to transform the experience-based claims on the use of T. crispa in traditional medicine practices into evidence-based information. The plant extract used in pharmacological and biological studies should be qualitatively and quantitatively analyzed based on its biomarkers. There should be detail in vitro and in vivo studies on the mechanisms of action of the pure bioactive compounds and more elaborate toxicity study to ensure safety of the plant for human use. More clinical trials are encouraged to be carried out if there are sufficient preclinical and safety data.
A total of fourteen pyrazoline derivatives were synthesized through cyclo-condensation reactions by chalcone derivatives with different types of semicarbazide. These compounds were characterized by IR, 1D-NMR (1H, 13C and Distortionless Enhancement by Polarization Transfer - DEPT-135) and 2D-NMR (COSY, HSQC and HMBC) as well as mass spectroscopy analysis (HRMS). The synthesized compounds were tested for their antituberculosis activity against Mycobacterium tuberculosis H37Ra in vitro. Based on this activity, compound 4a showed the most potent inhibitory activity, with a minimum inhibitory concentration (MIC) value of 17 μM. In addition, six other synthesized compounds, 5a and 5c-5g, exhibited moderate activity, with MIC ranges between 60 μM to 140 μM. Compound 4a showed good bactericidal activity with a minimum bactericidal concentration (MBC) value of 34 μM against Mycobacterium tuberculosis H37Ra. Molecular docking studies for compound 4a on alpha-sterol demethylase was done to understand and explore ligand-receptor interactions, and to hypothesize potential refinements for the compound.
Phytosterols are plant sterols with a chemical structure similar to cholesterol. It has anti-cholesterol, anti-cancer and anti-oxidant properties which are probably mediated by suppression of lipid peroxidation. However, there are limited studies on the effects of phytosterols on lipid peroxidation. The aim of this study is to determine the effects of phytosterols on plasma and tissue malondialdehyde (MDA) of rats exposed to carbon tetrachloride. The rats were divided into four groups of normal control (NC), carbon tetrachloride (CCl4), phytosterol (P) and phytosterol+carbon tetrachloride (P+CCl4).
The P and P+CCl4 groups were pretreated with subcutaneous phytosterol at 140 mg/kg once weekly for 5 weeks while the NC and CCl4 groups only received olive oil (vehicle). A single oral dose of carbon tetrachloride was then given to rats in the CCl4and P+CCl4 groups to induce lipid peroxidation. After 24 hours, all the rats were sacrificed and the plasma and tissue MDA were measured. Our results showed carbon tetrachloride had caused significant elevations of the plasma and hepatic MDA of the CCl4 group compared to the NC group. Phytosterol pretreatment (P+CCl4 group) were able to prevent the MDA elevations. Phytosterols treatments in normal rats (P group) were found to reduce the hepatic MDA level. The conclusion of this study was that phytosterols are effective suppressor of plasma and hepatic lipid peroxidation. They have potential as supplements to further reduce lipid peroxidation in healthy individuals.
Our continuing research on the Aglaia genus (family Meliaceace) has led us to this first study on the chemical constituents of Aglaia lanuginose (bark). The dichloromethane extract from the bark of Aglaia lanuginose showed cytotoxicity against HL-60 leukaemia cell line (45% inhibition) at 20 µg/ml and was prioritised for further investigation. Repeated chromatography of the dichloromethane extract yielded the known dammarane triterpenes which were identified as cabralealactone (1), methyl eichlerianate (2), cabraleone (3), ocotillone (4), eichleriatone (5), eichlerianic acid (6) and shoreic acid (7) together with the known sterols, sitosterol (9) and stigmasterol (10). Another isolated compound was the aromatic 4-hydroxycinnamyl-acetate (8), which has not been reported to be present in a plant from the Meliaceae family. The structures of all the compounds were elucidated on the basis of spectroscopic methods (IR, MS and NMR). Cytotoxicity testing of 1-10 showed activity only for mixtures of (3, 4), and (5, 6).