Chemical constituents from Urtica fissa stem and their inhibitory effects on α-glucosidase activity.

A new unsaturated fatty acid (E)-7,9-diene-11-carbonyl stearic acid (1) and a new lignan 8'-acetyl olivil (2), together with 14 known compounds (3-16), were isolated from the stem of Urtica fissa E. Pritz. Their structures were elucidated by spectroscopic and mass-spectrometric analyses. 8'-Acetyl olivil (2), (6 R,9R)-roseoside (15) and urticol-7-O-ß-d-glucopyrannoside (16) exhibited significant inhibition on α-glucosidase activities, with IC50 values less than 9 µM.

Changes in Soybean (Glycine max L.) Flour Fatty-Acid Content Based on Storage Temperature and Duration.

Soybeans are low in saturated fat and a rich source of protein, dietary fiber, and isoflavone; however, their nutritional shelf life is yet to be established. This study evaluated the change in the stability and quality of fatty acids in raw and roasted soybean flour under different storage temperatures and durations. In both types of soybean flour, the fatty-acid content was the highest in the order of linoleic acid (18-carbon chain with two double bonds; C18:2), oleic acid (C18:1), palmitic acid (C16:0), linolenic acid (18:3), and stearic acid (C18:0), which represented 47%, 26%, 12%, 9%, and 4% of the total fatty-acid content, respectively. The major unsaturated fatty acids of raw soybean flour-oleic acid, linoleic acid, and linolenic acid-decreased by 30.0%, 94.4%, and 97.7%, and 38.0%, 94.8%, and 98.0% when stored in polyethylene and polypropylene film, respectively, after 48 weeks of storage under high-temperature conditions. These values were later increased due to hydrolysis. This study presents the changes in composition and content of two soybean flour types and the changes in quality and stability of fatty acids in response to storage temperature and duration. This study shows the influence of storage conditions and temperature on the nutritional quality which is least affected by packing material.

Recovery and Utilization of Palm Oil Mill Effluent Source as Value-Added Food Products.

The environmental impacts of palm oil mill effluent (POME) have been a concern due to the water pollution and greenhouse gases emissions. Thus, this study was conducted to recover the value-added products from POME source before being discharged. The samples, before (X) and after (Y) the pre-recovery system in the clarification tank were sampled and analysed and proximate analysis indicated that both samples are energy rich source of food due to high contents of fats and carbohydrates. GCMS analysis showed that the oil extracts contain predominantly palmitic, oleic, linoleic and stearic acids. Regiospecific analysis of oil extracts by quantitative 13C-NMR spectroscopy demonstrated that both oil extracts contain similar degree of saturation of fatty acids at sn-2 and sn-1,3 positions. The samples are rich in various phytonutrients, pro-vitamin A, vitamin E, squalene and phytosterols, thus contributing to exceptionally high total flavonoid contents and moderate antioxidant activities. Overall, samples X and Y are good alternative food sources, besides reducing the environmental impact of POME.

Potential of Laurencia obtusa as a substrate for the development of a probiotic Saccharomyces cerevisiae.

Laurencia obtusa (Ceramiales, Rhodophyta) has tremendous nutritional value, being high in proteins, oligosaccharides, vitamins, essential minerals, and fatty acids, and it is a rich source of amino acids and trace elements. In this study, L. obtusa was extracted and subjected to phenolic, sugar and flavonoid analyses.The fatty acid, vitamin and phytosterol contents in Saccharomyces cerevisiae were evaluated when it was incubated with L. obtusa dry biomass. The fatty acids in the lipid extract were analysed after converting them into methyl esters using gas chromatography, and vitamin concentrations were measured using high-performance liquid chromatography (HPLC). According to the achieved results, the total fatty acid levels and vitamin contents of the S. cerevisiae prepared with algal extract increased at different rates. Our results showed that α-tocopherol decreased in the group in which the S. cerevisiae was added the algal extract. When compared to the control group, ergesterol increased in the group in which L. obtusa extract was added. Additionally, when compared to the control group in which L. obtusa extract was added, stearic acid (18:0), oleic acid (18:1) and linoleic acid (18:2) increased in the other groups. Palmitoleic acid (16:1) increased in the L. obtusa culture medium, but palmitic acid decreased in the L. obtusa culture medium. In conclusion, it was determined that the L. obtusa extract added to the development medium of S. cerevisiae caused differences in the synthesis of some vitamins and fatty acids.

Fermented Ginseng Contains an Agonist of Peroxisome Proliferator Activated Receptors α and γ.

Peroxisome proliferator activated receptor (PPAR) is a nuclear receptor that is one of the transcription factors regulating lipid and glucose metabolism. Fermented ginseng (FG) is a ginseng fermented by Lactobacillus paracasei A221 containing minor ginsenosides and metabolites of fermentation. DNA microarray analysis of rat liver treated with FG indicated that FG affects on lipid metabolism are mediated by PPAR-α. To identify a PPAR-α agonist in FG, PPAR-α transcription reporter assay-guided fractionation was performed. The fraction obtained from the MeOH extract of FG, which showed potent transcription activity of PPAR-α, was fractionated by silica gel column chromatography into 16 subfractions, and further separation and crystallization gave compound 1 together with four known constituents of ginseng, including 20(R)- and 20(S)-protopanaxadiol, and 20(R)- and 20(S)-ginsenoside Rh1. The structure of compound 1 was identified as 10-hydroxy-octadecanoic acid by (1)H- and (13)C-NMR spectra and by EI-MS analysis of the methyl ester of 1. Compound 1 demonstrated much higher transcription activity of PPAR-α than the other isolated compounds. In addition, compound 1 also showed 5.5-fold higher transcription activity of PPAR-γ than vehicle at the dose of 20 µg/mL. In the present study, we identified 10-hydroxy-octadecanoic acid as a dual PPAR-α/γ agonist in FG. Our study suggested that metabolites of fermentation, in addition to ginsenosides, contribute to the health benefits of FG.

Gas Chromatography-Mass Spectrometry Analysis of Constituent Oil from Lingzhi or Reishi Medicinal Mushroom, Ganoderma lucidum (Agaricomycetes), from Nigeria.

Gas chromatography-mass spectrometry analysis of constituent oil from dried Ganoderma lucidum was carried out. Fresh G. lucidum obtained from its natural environment was thoroughly washed with distilled water and air-dried for 2 weeks and the component oils were extracted and analyzed. Four predominant components identified were pentadecanoic acid, 14-methyl-ester (retention time [RT] = 19.752 minutes; percentage total = 25.489), 9,12-octadecadienoic acid (Z,Z)- (RT = 21.629 minutes and 21.663 minutes; percentage total = 25.054), n-hexadecanoic acid (RT = 20.153 minutes; percentage total = 24.275), and 9-octadecenoic acid (Z)-, methyl ester (RT = 21.297 minutes; percentage total = 13.027). The two minor oils identified were 9,12-octadecadienoic acid, methyl ester, (E,E)- and octadecanoic acid, methyl ester (RT = 21.246 minutes and 21.503 minutes; percentage total = 7.057 and 5.097, respectively).

Utilization of Stearic acid Extracted from Olive Pomace for Production of Triazoles, Thiadiazoles and Thiadiazines Derivatives of Potential Biological Activities.

Olive Pomace was firstly dried, then pomace olive oil was extracted, and the obtained oil was hydrolyzed to produce glycerol and mixture of fatty acids. Fatty acids mixture was separated, this mixture was then cooled, where the all saturated fatty acids were solidified, and then they were filtered off. These saturated fatty acids were identified by GC mass after esterification, and were identified as stearic, palmitic and myristic acids. Stearic acid was extracted using supercritical CO2 extractor. The stearic acid was confirmed by means of GC mass after its esterification, and it was used as starting material for preparation of a variety of heterocyclic compounds, which were then tested for their antimicrobial activities. Thus the long-chain fatty acid hydrazide (2) was prepared from the corresponding long-chain fatty ester with hydrazine hydrate. Reacting 2 with phenyl isothiocyanate afforded the corresponding thiosemicarbazide 4. The later 4 underwent intramolecular cyclization in basic medium, and gave the s-triazole derivative 5, which was methylated and afforded 3-heptadecanyl-5-(methylthio)-4-phenyl-4H-1,3,4-triazole (7), which was then treated with hydrazine hydrate and afforded the corresponding 1-(5-heptadecanyl-4-phenyl-4H-1,2,4-triazol-3-yl) hydrazine (8).On the other hand, thiosemicarbazide 4 underwent intramolecular cyclization in acid medium and afforded the corresponding thiadiazole derivative 6.Treatment of thiosemicarbazide 4 with ethyl chloro(arylhydrazono) acetate derivatives 9a-b, furnished a single product 13 (Scheme 6). Similarly, when the thiosemicarbazide 4 was treated with the phenylcarbamoylarylhydrazonyl chloride 10a-c, it afforded (3-Aryl-N-5-(phenylcarbamoyl)-1,3,4-thiadiazol-2(3H)-ylidene)octadecanehydrazide 15a-c (Scheme 7). Also the reaction of thiosemicarbazide 4 with 2-oxo-N-arylpropanehydrazonoyl chlorides 11a-c and N-phenylbenzohydrazonoyl chloride 11d gave the corresponding thiadiazole derivatives 16a-d as shown in Scheme 8. A solution of thiosemicarbazide 4 was treated with the haloketones 17a-c, afforded the thiadiazine derivatives 20a-c, as shown in Scheme 9. Analogously, the thiosemicarbazide 4 was reacted with α-haloketones 21a-b and afforded the corresponding products 22a-b (Scheme 9). The structure elucidation of all synthesized compounds is based on the elemental analysis and spectral data (IR, 1H NMR, 13C NMR and MS).

Studies on the acaricidal mechanism of the active components from neem (Azadirachta indica) oil against Sarcoptes scabiei var. cuniculi.

Octadecanoic acid-3,4-tetrahydrofuran diester, isolated from neem (Azadirachta indica) oil, exhibited potent acaricidal activity against Sarcoptes scabiei var. cuniculi. In this paper, the acaricidal mechanism of octadecanoic acid-3,4-tetrahydrofuran diester against Sarcoptes scabiei var. cuniculi was evaluated based on pathologic histology and enzyme activities. The results showed that after compound treatment for 24h at a concentration of 20mg/mL, the lesions of mites were prominent under transmission electron microscopy. The lesions consisted of the lysis of dermis cell membranes and cell nuclear membranes, mitochondrial morphological abnormalities, the drop of spinal disorders, and mitochondrial vacuolization. The activity of superoxide dismutase (SOD), peroxidase (POD), glutathione-s-transferases (GSTs), and Ca(2+)-ATPase of mites significantly changed after treatment with octadecanoic acid-3,4-tetrahydrofuran diester compared with the control group. The activities of SOD, POD, and Ca(2+)-ATPase were significantly suppressed, whereas that of GSTs was activated. These results indicated that the mechanism of the acaricidal activity of octadecanoic acid-3,4-tetrahydrofuran diester was mainly achieved through interference with the energy metabolism of mites, thus resulting in insect death.

A novel sodium N-fatty acyl amino acid surfactant using silkworm pupae as stock material.

A novel sodium N-fatty acyl amino acid (SFAAA) surfactant was synthesized using pupa oil and pupa protein hydrolysates (PPH) from a waste product of the silk industry. The aliphatic acids from pupa oil were modified into N-fatty acyl chlorides by thionyl chloride (SOCl2). SFAAA was synthesized using acyl chlorides and PPH. GC-MS analysis showed fatty acids from pupa oil consist mainly of unsaturated linolenic and linoleic acids and saturated palmitic and stearic acids. SFAAA had a low critical micelle concentration, great efficiency in lowering surface tension and strong adsorption at an air/water interface. SFAAA had a high emulsifying power, as well as a high foaming power. The emulsifying power of PPH and SFAAA in an oil/water emulsion was better with ethyl acetate as the oil phase compared to n-hexane. The environment-friendly surfactant made entirely from silkworm pupae could promote sustainable development of the silk industry.

[The fatty acid composition of ordinary flax seed oil (Linum usitatissimum L.) cultivated in Georgia and its byological activity].

The aim of the study was individual quantitatively and qualitatively determination of fatty acids in ordinary flax seed oil (Linum usitatissimum L.), cultivated in Georgia. The neutral lipids extracts were fractionated and analyzed by high performance liquid chromatography (PTC-1, Waters) with refractory detector R-401. Analitical column (150,0x3,0 mm) was filled with reversphase Bondopak C18). Software OASIS-740 is used. The correction retention times of each fatty acids is compared with comformity standard. The investigation showed that in flax seed oil linoleic (31,3±2,1 mg%) and linolenic (40,2±2,9 mg%) acids were predominant and together constitute principal basic of research composition. The flax seed oil contained also palmitic and stearic acids in less quantitaty.

Resolution behavior of cis- and trans-octadecenoic acid isomers by AOCS official method using SP-2560 column.

The gas chromatography-flame ionization detector equipped with a higher polarity column (i.e., SP-2560) has often been used for the quantification of trans-fatty acids in food. In particular, AOCS Ce 1h-05, the official method of the American Oil Chemists' Society (AOCS), is a highly effective method to separate the isomers of trans-fatty acids. In this study, the resolution behavior and the response factors of cis- and trans-octadecenoic acid methyl ester (C18:1-ME) isomers separated by the AOCS Ce 1h-05 method were investigated, and the contents of each cis- and trans-C18:1-ME isomer in partially hydrogenated vegetable oil (PHVO) and milk fat were quantified by using the calibration curves obtained for the respective isomers. The relative response factors for the trans- and cis-C18:1-ME isomers against the internal standard heneicosanoic acid methyl ester (C21:0-ME) were 1.031 ± 0.040 (mean ± SD) and 0.990 ± 0.032, respectively. The relative response factors of trans-isomers tend to be higher than those of cis-C18:1-ME isomers. The peaks of cis-4-C18:1-ME, cis-5-C18:1-ME, cis-6-C18:1-ME, cis-7-C18:1-ME, cis-8-C18:1-ME, and cis-9-C18:1-ME isomers overlapped with those of trans-C18:1-ME isomers. Both PHVO and milk fat contained many types of cis- and trans-C18:1 isomers, and the total contents of the trans-C18:1 isomer in PHVO and milk fat were 28.01 g and 3.62 g per 100 g oil, respectively. When the trans-C18:1-ME isomer was separated from the cis-C18:1-ME by using a silver-ion cartridge column before the analyses, the total contents of the trans-C18:1 isomer in PHVO and milk fat were 23.03 g and 2.78 g per 100 g oil, respectively. The difference in the trans-C18:1 isomer content between the two methods was ascribed to the partial overlapping of cis-isomer peaks with the peaks of trans-C18:1-ME isomers, in the chromatogram.

[Study on chemical constituents from Anoectochilus chapaensis].

OBJECTIVE: To investigate the chemical constituents from the whole herbs of Anoectochilus chapaensis. METHODS: The chemical constituents were isolated and purified by repeated column chromatographies with silica gel, Sephadex LH-20 and preparative TLC. Their structures were identified by their physiochemical property and spectral data. RESULTS: 6 compounds were isolated and elucidated as follows: (1) Friedelin, (2) Sorghumol, (3) 5alpha, 8alpha-epidioxyergost-22-en-3beta-ol, (4) Stearic acid, (5) Octadecane and (6) Epifriedelanol. CONCLUSION: Compound (1), (2) and (4) are isolated from this plant for the first time, and compound (3), (5) and (6) are isolated from genera Anoectochilus for the first time.

[Chemical constituents of Berchemia lineate].

OBJECTIVE: To investigate the chemical constituents of the roots of Berchemia lineate as a medicinal plant of Yao nationality in China. METHODS: Compounds were isolated by various column chromatography and elucidated by physicochemical and spectral analysis. RESULTS: Nine compounds were isolated from the 95% ethanol extract of the roots of Berchemia lineate and their structures were identified as palmitic acid (1), octadecanoic acid (2), beta-sitosterol (3), stigmasterol (4), fernenol (5), chrysophanol (6), physcion (7), floribundiquinone D (8), 2-acetylphyscion(9) respectively. CONCLUSION: Compounds 1-4,7-9 are isolated from this plant for the first time,and compounds land 2 are firstly isolated from this genus.

Stereoselective oxidation of regioisomeric octadecenoic acids by fatty acid dioxygenases.

Seven Z-octadecenoic acids having the double bond located in positions 6Z to 13Z were photooxidized. The resulting hydroperoxy-E-octadecenoic acids [HpOME(E)] were resolved by chiral phase-HPLC-MS, and the absolute configurations of the enantiomers were determined by gas chromatographic analysis of diastereoisomeric derivatives. The MS/MS/MS spectra showed characteristic fragments, which were influenced by the distance between the hydroperoxide and carboxyl groups. These fatty acids were then investigated as substrates of cyclooxygenase-1 (COX-1), manganese lipoxygenase (MnLOX), and the (8R)-dioxygenase (8R-DOX) activities of two linoleate diol synthases (LDS) and 10R-DOX. COX-1 and MnLOX abstracted hydrogen at C-11 of (12Z)-18:1 and C-12 of (13Z)-18:1. (11Z)-18:1 was subject to hydrogen abstraction at C-10 by MnLOX and at both allylic positions by COX-1. Both allylic hydrogens of (8Z)-18:1 were also abstracted by 8R-DOX activities of LDS and 10R-DOX, but only the allylic hydrogens close to the carboxyl groups of (11Z)-18:1 and (12Z)-18:1. 8R-DOX also oxidized monoenoic C(14)-C(20) fatty acids with double bonds at the (9Z) position, suggesting that the length of the omega end has little influence on positioning for oxygenation. We conclude that COX-1 and MnLOX can readily abstract allylic hydrogens of octadecenoic fatty acids from C-10 to C-12 and 8R-DOX from C-7 and C-12.

Phytochemical investigation and antifeedant activity of Premna latifolia leaves.

The essential oil of Premna latifolia Roxb. was obtained by hydrodistillation of fresh leaves of the plant having an oil yield of 0.05%, both non-polar and essential oil were analysed by GC and GC-MS. Hexane fraction of the leaves of P. latifolia was transesterified and analysed by GC and GC-MS, 40 non-polar components were identified comprising 89.3%. The most abundant fatty acid constituents were hexadecanoic acid (25.04%), 8,11,14-docosatrienoic acid (13.62%), octadecanoic acid (6.82%), 9,12-octadecadienoic acid (4.19%) and 29 components were investigated in the essential oil which comprises 78.1%. The most abundant oil constituents were 1-octen-3-ol (35.69%), terpendiol II (7.19%), δ-guaiene (7.49%) 2-undecanone (4.80%) and α-pinene (3.27%). Different extracts were also tested against polyphagous crop pest Spodoptera litura for antifeedant activity. Essential oil showed maximum growth reduction of 56.83% followed by chloroform extract of 43.93%.

Development, characterization and commercial application of palm based dihydroxystearic acid and its derivatives: an overview.

Hydroxyl fatty acids and their derivatives are of high value due to their wide range of industrial application, including cosmetic, food, personal care and pharmaceutical products. Realizing the importance of hydroxyl fatty acids, and yet due to the absence of the conventional starting raw materials, Malaysia has developed 9,10-dihydroxystearic acid (9,10-DHSA) and its derivatives from locally abundant palm based oils. The aim of this article is to provide a general description of the works that have thus far being done on palm based 9,10-DHSA: starting from its conception and production from commercial grade palm based crude oleic acid via epoxidation and hydrolysis, purification through solvent crystallization and characterization through wet and analytical chemistry, moving on to developmental works done on producing its derivatives through blending, esterification, amidation and polymerization, and completing with applications of 9,10-DHSA and its derivatives, e.g. DHSA-stearates and DHSA-estolides, in commercial products such as soaps, deodorant sticks and shampoos. This article incorporates some of the patent filed technological knowhow on 9,10-DHSA and its derivatives, and will also point out some of the shortcomings in previously published documents and provide some recommendations for future research works in mitigating these shortcomings.

[Study on the chemical constituents from Fructus Toosendan (III)].

OBJECTIVE: To study the chemical constituents from Fructus Toosendan. METHODS: Isolation and identification were carried out by using various chromatography techniques and spectral methods. RESULTS: Ten compounds were isolated and identified as n-Hentriacontane (I), Octacosyl alcohol (II), Stearic acid (III), Linoleic acid (IV), Isovanillin (V), Vanillin (VI), Vanillic acid (VII), Ohchinal (VIII), Succinic acid (IX) and Homoeriodictyol (X). CONCLUSION: Compounds V, VII, IX, X are isolated from this genus and compounds I, II, III are obtained from this plant for the first time.

[Chemical constituents from root bark of Tripterygium hypoglaucum].

OBJECTIVE: To investigate chemical constituents of the root bark of Tripterygium hypoglaucum. METHOD: Compounds were isolated by column chromatography on silica gel and Sephadex LH-20, and their structures were identified on the basis of spectral data (MS, 1H-NMR and 13C-NMR). RESULT: Twelve compounds were isolated and identified as friedelin (1), 3-oxo-olean-9(11),12-diene (2), canophyllal (3), 3-acetoxy oleanolic acid (4), triptophenolide (5), triptonoterpene methyl ether (6), tricosanoic acid (7), beta-sitosterol (8), stearic acid (9), glut-5-en-3beta,28-diol (10), palmitic acid (11) and daucostorol (12). CONCLUSION: Compounds 1, 2, 3, 7 and 10 were isolated from T. hypoglaucum and 7 from the genus Tripterygium for the first time.

[Studies on the chemical constituents of Ficus microcarpa].

OBJECTIVE: To study the chemical constituents of the Ficus microcarpa. METHODS: Isolation and identification were carried out by using various chromatography techniques and spectral methods. RESULTS: Eight compounds were isolated. Their structures were identified as beta-amyrone (I), lupeol (II), lupeol acetate (III), maslinic acid (IV), epifriedelinol (V), stearic acid (VI), beta-sitosterol (VI), daucosterol (VI). CONCLUSION: Compounds I, II, VI are isolated from this plant for the first time.

Clytostoma callistegioides (Bignoniaceae) wax extract with activity on aphid settling.

A bioassay-guided fractionation of leaf extracts from Clytostoma callistegioides (Cham.) Bureau ex Griseb. (Bignoniaceae) led to isolation of a natural mixture of four fatty acids with anti-insect activity against aphids. The compounds were identified by GC-MS as palmitic, stearic, linoleic and linolenic acids and quantified as their methyl esters. The anti-aphid activity of the natural mixture was traced to linolenic and linoleic acids, as shown by the settling inhibition activity of synthetic samples. Interestingly, the saturated acids (palmitic and stearic) tested alone stimulated settling on one of the tested aphids (Myzus persicae), but not on the other tested species (Rhopalosiphum padi). Although ubiquitous, none of these free acids have been previously reported in this Bignoniaceae species. The leaf surface chemistry, which is likely involved in modulating aphid settling behavior, was further investigated for the occurrence of lipophilic substances by histochemical staining. Short, stalked glandular trichomes, previously undescribed for this species, stained with osmium tetroxide and Sudan III, suggesting that the secretion of the defensive acids is related to these surface trichomes.