Hexane-soluble Extract Research Articles

In vitro anti-HIV and cytotoxic effects of pure compounds isolated from Croton macrostachyus Hochst. Ex Delile

Croton macrostachyus is an important plant in traditional African medicine, widely utilized to treat a variety of diseases. In Kenya, HIV-infected patients use leaf and root decoctions of the plant as a cure for cough, back pain, bleeding, skin diseases, warts, pneumonia, and wounds. This study aimed to evaluate the anti-HIV activities and cytotoxic effects of extracts and chemical constituents isolated from C. macrostachyus. In our previous study we demonstrated that the hexane, CH2Cl2, ethyl acetate and methanol soluble fractions of a 1:1 v/v/ CH2Cl2/MeOH crude extracts of the leaves and stem bark of C. macrostachyus exhibited potent anti-HIV activities against HIV-1 with IC50 values ranging from 0.02–8.1 μg/mL and cytotoxicity effects against MT-4 cells ranging from IC50 = 0.58–174 μg/mL. Hence, hexane soluble extract of 1:1 v/v/ CH2Cl2/MeOH crude extract of the leaves of C. macrostachyus, that was more potent against HIV-1 at IC50 = 0.02 μg/mL was subjected to column chromatography leading to the isolation of 2-methoxy benzyl benzoate (1), lupenone (2), lupeol acetate (3), betulin (4), lupeol (5), sitosterol (6) and stigmasterol (7). Lupenone (2), lupeol acetate (3) and betulin (4) exhibited anti-HIV-1 inhibition at IC50 = 4.7 nM, 4.3 and 4.5 μg/mL respectively. The results obtained from this study support the potential of C. macrostachyus, as a source of anti-HIV constituents.

Antimutagenic bis (2-ethylhexyl) phthalate isolated from octopus (Paraoctopus vulgaris)

Abstract In the present study, the antimutagenic activity of methanolic (MP) and hexanic (HP) phase from hexane-soluble extract of Paraoctopus vulgaris was evaluated. The HP showed significant concentration-dependent antimutagenic activity (p < 0.05) in the Ames assay against aflatoxin B1 (AFB1) using Salmonella typhimurium TA98 and TA100 tester strains. Seven fractions (F1-F7) were obtained from HP by silica gel-column chromatography and the antimutagenic activity of F6 and F7 caused significant reduction (p < 0.05) in the number of AFB1-induced revertants in both strains. However, high antimutagenic activity was exhibited in TA98 strain (85-97% reversion inhibition) and remained at a fraction-concentration of 3 μg/mL. F6 and F7 composition was analyzed by high-performance liquid chromatography/photodiode array, both fractions shared one peak at 9.42 min suggesting presence of the same compound. 1H-NMR and 13C-NMR analysis results indicate that the bioactive compound is bis (2-ethylhexyl) phthalate. Based on of these results bis (2-ethylhexyl) phthalate exhibit antimutagenic activity, which allows to consider it for further investigation as a potential chemopreventive compound.

Lactic acid fermentation enriches the profile of biogenic fatty acid derivatives of avocado fruit (Persea americana Mill.)

This study investigated the capability of selected autochthonous lactic acid bacteria to enrich the portfolio of bioactive compounds of avocado fruit (Persea americana Mill.), with the perspective of producing dietary supplements or pharmaceutical preparations. Fermented avocado puree resulted in high levels of total free amino acids. Fermentation also led to a marked increase of antioxidant activity, with the highest levels found in water and hexane soluble extracts. Bio-converted phenolic compounds and fatty acids derivatives resulting from bacterial metabolism were likely responsible for the increased antioxidant activity. Fermentation caused the fortification of avocado puree with some hydroxy fatty acids, which deserved marked attention due to their health-promoting activities. Oleic and linoleic acids were highly metabolized by Lactobacillus plantarum AVEF17, leading to high levels of mono, di-, and tri-hydroxy-octadecenoic acids.

Anti-viral activity of culinary and medicinal mushroom extracts against dengue virus serotype 2: an in-vitro study

BackgroundDengue is a mosquito-borne viral infection that has become a major public health concern worldwide. Presently, there is no specific vaccine or treatment available for dengue viral infection.MethodsLignosus rhinocerotis, Pleurotus giganteus, Hericium erinaceus, Schizophyllum commune and Ganoderma lucidium were selected for evaluation of their in-vitro anti-dengue virus serotype 2 (DENV-2) activities. Hot aqueous extracts (HAEs), ethanol extracts (EEs), hexane soluble extracts (HSEs), ethyl acetate soluble extracts (ESEs) and aqueous soluble extracts (ASEs) were prepared from the selected mushrooms. The cytotoxic effects of the extracts were evaluated by the MTT assay. The anti-DENV-2 activities of the extracts were evaluated in three different assays: simultaneous, attachment and penetration assays were perfomed using plaque reduction assays and RT-qPCR assays. The effect of the addition time on viral replication was assessed by the time of addition assay, and a virucidal assay was carried out to evaluate the direct effect of each mushroom extract on DENV-2. The chemical composition of glucans, and the protein and phenolic acid contents in the extracts were estimated.ResultsWe found that the HAEs and ASEs of L. rhinocerotis, P. giganteus, H. erinaceus and S. commune were the least toxic to Vero cells and showed very prominent anti-DENV2 activity. The 50% inhibitory concentration (IC50) values of the ASEs ranged between 399.2–637.9 μg/ml, while for the HAEs the range was 312.9–680.6 μg/ml during simultaneous treatment. Significant anti-dengue activity was also detected in the penetration assay of ASEs (IC50: 226.3–315.4 μg/ml) and HAEs (IC50: 943.1–2080.2 μg/ml). Similarly, we observed a marked reduction in the expression levels of the ENV and NS5 genes in the simultaneous and penetration assays of the ASEs and HAEs. Time-of-addition experiments showed that the highest percent of anti-DENV2 activity was observed when the mushroom extracts were added immediately after virus adsorption. None of the extracts exhibited virucidal effect. Chemical composition analysis showed that the major components in the mushroom HAEs and ASEs were glucan (beta D-glucan) and proteins, however, there was no significant correlation between the anti-dengue activity and the concentration of glucans and proteins.ConclusionThese findings demonstrated the potential of mushroom extracts as anti-dengue therapeutic agents with less toxic effects.

Simultaneous determination of nine lignans from Schisandra chinensis extract using ultra-performance liquid chromatography with tandem mass spectrometry in rat plasma, urine, and gastrointestinal tract samples: application to the pharmacokinetic study of Schisandra chinensis.

The fruit of Schisandra chinensis is a well-known herbal medicine and dietary supplement due to a variety of biological activities including antihepatotoxic and antihyperlipidemic activities. However, the simultaneous validation methodology and pharmacokinetic investigation of nine lignans of S. chinensis extract in biological samples have not been proved yet. Thus, the present study was undertaken to develop the proper sample preparation method and simultaneous analytical method of schisandrol A, gomisin J, schisandrol B, tigloylgomisin H, angeloylgomisin H, schisandrin A, schisandrin B, gomisin N, and schisandrin C in the hexane-soluble extract of S. chinensis to apply for the pharmacokinetic study in rats. All intra- and interprecisions of nine lignans were below 13.7% and accuracies were 85.1-115% and it is enough to evaluate the pharmacokinetic parameters after both intravenous and oral administration of hexane-soluble extract of S. chinensis to rats.

Profiling of Alkaloids and Eremophilanes in Miracle Tea (Packera candidissima and P. bellidifolia) Products

Commercial preparations of the Mexican herbal drug known as "miracle tea" (Packera candidissima and P. bellidifolia) have been profiled qualitatively by HPLC and GC-MS. Eremophilanes (3-7) were the major components found in the hexane-soluble fraction, while pyrrolizidine alkaloids (PAs) were identified in the alkaloid extracts. The content of free PAs and their N-oxides was determined for a total of 22 samples, and the results showed that the amount of these hepatotoxic compounds (0.0005-0.94% free PAs; 0.0004-0.55% N-oxides), through the presence of retrorsine (1) and senesionine (2) as the main constituents, may reach toxic levels. Hexane-soluble extracts from commercial presentations (dried whole plants) of both species afforded neoadenostylone (3), 6-(2-methylbutanoyloxy)-9-oxo-1-(10)-furanoeremophilene (4), and epineoadenostylone (5), in addition to methyl-4-hydroxyphenylacetate (8) and methyl-2-(1-hydroxy-4-oxocyclohexyl)acetate (9). Also, epicacalone (6) and the new compound 2β-hydroxyneoadenostylone (7) were isolated from P. bellidifolia.

Batatinosides II−VI, Acylated Lipooligosaccharides from the Resin Glycosides of Sweet Potato

Sweet potato ( Ipomoea batatas) belongs to the Convolvulaceae (morning glory family) and is native to Mexico and Central America. Its edible tuberous roots have been much appreciated since pre-Hispanic times in Mesoamerica and now play an important role as a basic diet staple and a medicinal plant worldwide. The hexane-soluble extract from roots, through preparative-scale recycling HPLC, yielded five new lipophilic oligosaccharides of jalapinolic acid, batatinosides II-VI ( 1- 5), as well as the known pescapreins I ( 6) and VII ( 7) and murucoidin I ( 8), which are part of the purgative resin glycoside mixture. NMR spectroscopy and FAB mass spectrometry were used to characterize their structures. Compounds 1 and 2 are tetraglycosidic lactones of operculinic acid C. The pentasaccharide structures for compounds 3 and 4 were confirmed to be macrolactones of simonic acid B, and that characterized for 5 was derived from operculinic acid A. The lactonization site of the aglycone was placed at C-3 of the second saccharide unit in all compounds except 4, where it was placed at C-2. All compounds contain an esterifying residue that is composed of a long-chain fatty acid, n-decanoic acid (capric) or n-dodecanoic acid (lauric). In compound 3, an additional short-chain fatty acid, (2 S)-methylbutyric acid, was also identified.

Resin Glycosides from Ipomoea pes-caprae

Ipomoea pes-caprae (beach morning-glory; "riñonina" for the herbal drug in Mexico) is prescribed by traditional healers to moderate "heat" in an infected kidney. The hexane-soluble extract from the aerial parts of this medicinal plant, through preparative-scale recycling HPLC, yielded six new lipophilic oligosaccharides of jalapinolic acid: pescaproside B (1) and pescapreins V-IX (2-6). The previously known pescaproside A (7), pescapreins I-IV (8-11), and stoloniferin III (12) were also identified in the analyzed material by means of HPLC comparison with authentic samples. The glycosidic acid structure for all pentasaccharides was confirmed as simonic acid B. Pescaproside B (1), an acylated glycosidic acid methyl ester, is structurally related to pescaprein III (10). Pescapreins V (2) and VI (3) are diasteroisomeric tetraglycosidic lactones of operculinic acid C. Both of these compounds contain (2S)-methylbutyric and n-dodecanoic acids as their esterifying residues. Pescapreins VII (4) and IX (6) are pentasaccharides that contain an n-decanoyl group as their esterifying fatty acid residue instead of the n-dodecanoyl found in pescapreins I (8) and IV (11). Pescaprein VIII (5) represents an isomer of pescaprein II (9) containing an n-dodecanoyl unit as the esterifying residue at position C-4 of the third rhamnose moiety and a 2-methylpropanoyl at C-2 of the second rhamnose. High-field NMR spectroscopy and FAB mass spectrometry were used to characterize all new isolated compounds.

Batatins I and II, Ester-Type Dimers of Acylated Pentasaccharides from the Resin Glycosides of Sweet Potato

Batatins I (1) and II (2), two ester-type dimers of acylated pentasaccharides, have been isolated by recycling HPLC from the hexane-soluble extract of sweet potato (Ipomoea batatas var. batatas). The structures were elucidated by a combination of high-resolution NMR spectroscopy and mass spectrometry. Complete analysis and unambiguous assignments of the 1H and 13C NMR spectra of 1 and 2 were achieved by 2D shift correlation measurements. The glycosidic acid forming each branched pentasaccharide monomeric unit was confirmed as simonic acid B. Three different fatty acids esterify this core at the same positions in both batatins: C-2 on the second rhamnose unit and C-4 and C-2 (or C-3) on the third rhamnose moiety. The acylating residues were identified as (+)-(2S)-methylbutanoic, dodecanoic (lauric), and cinnamic acids. The site of lactonization by the aglycon in unit A was placed at C-3 of the second saccharide. The position for the ester linkage for monomeric unit B on the macrocylic unit A was identified as C-3 of the terminal rhamnose' ''. Through spectroscopic simulation of these complex oligosaccharides, the chemical shifts and coupling constants were deduced for the overlapped proton resonances with a non-first-order resolution. The experimental NMR spectroscopic values registered for batatinoside I (3), a new polyacylated macroyclic pentasaccharide also isolated from this plant, were used as the starting point for spectral simulation of 1 and 2. Both polymers 1 and 2 represent dimers of compound 3.

Monoamine oxidase inhibitory naphthoquinones from the roots ofLithospermum erythrorhizon

Activity-guided fractionation of a hexane-soluble extract of the roots of Lithospermum erythrorhizon, using a mouse brain monoamine oxidase (MAO) inhibition assay, led to the isolation of two known naphthoquinones, acetylshikonin and shikonin, and a furylhydroquinone, shikonofuran E. These compounds were shown to inhibit MAO with IC50 values of 10.0, 13.3, and 59.1 microM, respectively. Although no specificity for MAO-A and MAO-B was shown by acetylshikonin and shikonin, a Lineweaver-Burk plot analysis indicated that the inhibition was competitive for both MAO-A and MAO-B activity.

Characterization of Lipophilic Pentasaccharides from Beach Morning Glory (Ipomoea pes-caprae)

The hexane-soluble extract from the aerial parts of the herbal drug Ipomoea pes-caprae (beach morning-glory), through preparative-scale recycling HPLC, yielded six lipophilic glycosides, namely, five new pentasaccharides of jalapinolic acid, pescaproside A (1) and pescapreins I-IV (2-5), as well as the known stoloniferin III (6). Saponification of the crude resin glycoside mixture yielded simonic acid B (7) as the glycosidic acid component, whereas the esterifying residues of the natural oligosaccharides comprised five fatty acids: 2-methylpropanoic, (2S)-methylbutyric, n-hexanoic, n-decanoic, and n-dodecanoic acids. Pescaproside A (1), an acylated glycosidic acid methyl ester, is related structurally to the product obtained from the macrolactone hydrolysis of pescapreins I-IV (2-5). All the isolated compounds (1-6), characterized through high-field NMR spectroscopy, were found to be weakly cytotoxic to a small panel of cancer cell lines.

Antifungal chromans inhibiting the mitochondrial respiratory chain of pea seeds and new xanthones from Calophyllum caledonicum.

Two new xanthones, caledonixanthone M 1 and caloxanthone L 2, and one new acid, caledonic acid 6 were isolated from the hexane-soluble extract of the stem bark of Calophyllum caledonicum. In the course of this phytochemical study, seven other known compounds - calothwaitesixanthone, calozeyloxanthone, allanxanthone, isoapetalic acid 3, calolongic acid 4, apetalic acid 5 and isocalolongic acid 7 - were isolated. Their antifungal activity against the growth of the human pathogenic fungus Aspergillus fumigatus was then investigated. The results indicated that the crude extract, calolongic acid 4 and isocalolongic acid 7 exhibited strong inhibitory effects with MIC (80) values of 8, 4, 2 microg/mL, respectively. Besides, calolongic acid 4, its lactone derivative 4a and isocalolongic acid 7 markedly reduced the respiration of pea seed mitochondria.

Detection of estrogenic activity in sediment-associated compounds using in vitro reporter gene assays

Sediments may be the ultimate sink for persistent (xeno-)estrogenic compounds released into the aquatic environment. Sediment-associated estrogenic potency was measured with an estrogen receptor-mediated luciferase reporter gene (ER-CALUX) assay and compared with a recombinant yeast screen. The ER-CALUX assay was more sensitive to 17β-estradiol (E2) than the recombinant yeast screen, with an EC50 of 6 pM E2 compared to 100 pM in the yeast screen. Yeast cells were unable to distinguish the anti-estrogens ICI 182 780 and (4-hydroxy)tamoxifen, which were agonistic in the yeast. Acetone-soluble fractions of hexane/acetone extracts of sediments showed higher estrogenic potency than hexane-soluble extracts in the ER-CALUX assay. Sediments obtained from industrialized areas such as the Port of Rotterdam showed the highest estrogenic potency of the 12 marine sediments tested (up to 40 pmol estradiol equivalents per gram sediment). The estrogenic activity of individual chemicals that can be found in sediments including: alkylphenol ethoxylates and carboxylates; phthalates; and pesticides, was tested. Increasing sidechain length of various nonylphenol ethoxylates resulted in decreased estrogenic activity. Of the phthalates tested, butylbenzylphthalate was the most estrogenic, though with a potency approximately 100 000 times less than E2. The organochlorine herbicides atrazine and simazine failed to induce reporter gene activity. As metabolic activation may be required to induce estrogenic activity, a metabolic transformation step was added to the ER-CALUX assay using incubation of compounds with liver microsomes obtained from PCB-treated rats. Results indicate that metabolites of E2, NP and bisphenol A were less active than the parent compounds, while metabolites of methoxychlor were more estrogenic following microsomal incubations.

A phenolic cinnamate dimer from Psoralea plicata

Caryophyllene oxide, α-tocopherol, Z and E-werneria chromenes, two furanocoumarins, bakuchicin and psoralen, in addition to plicatin-B, lupeol and stigmasterol, have been isolated from the hexane-soluble extract of the aerial parts of Psoralea plicata. Plicatin-A, 3-(-3-methyl-2,3-epoxybutyl)- p-coumaric acid methyl ester and a new dimer, α- diplicatin B, were isolated from the ethyl acetate-soluble fraction. From the butanol-soluble matter, roseoside A, daidzin, isopsoralic acid- O-gluco-pyranosyl and isovitexin were isolated. Most of these compounds have been isolated from this species for the first time, although known from other plant sources. © 1997 Elsevier Science Ltd. All rights reserved

Liquefaction of Japanese bituminous Akabira coal catalyzed by molten salts under D 2 atmosphere

Akabira coal (Japanese bituminous coal) was liquefied in the presence of molten salts like SnCl 2/KCl under a hydrogen or deuterium atmosphere (at 400°C for 1 h). Resulting products were separated into gaseous products, hexane soluble (HS), hexane insoluble but benzene soluble (HI/BS), benzene insoluble but pyridine soluble (BI/PS) and residue. Two extracts, HS and HI/BS, were separated by column chromatography. Three fractions of the HS extract account for up to 90% of the HS and four fractions of the HI/BS extract up to 80% of HI/BS. The distribution of deuterium atoms in three fractions of HS were examined by measuring their FD/MS and 2H NMR properties, and comparing these results with corresponding data of three fractions of HS obtained in a H 2 atmosphere. These results strongly suggest the preferential incorporation of deuterium atom at α-carbon adjacent to aromatic compounds. Kinetic features of the liquefaction are discussed according to the detailed analysis of three fractions of HS.

Comparison by g.c.-m.s. of liquefaction extracts from coal maceral concentrates

Differences between the compositions of partly hydrocracked hexane-soluble extract fractions from the liquefaction of maceral concentrates were investigated by gas chromatography-mass spectrometry. The technique identifies components within only a relatively narrow range of molecular masses, but some systematic differences were nevertheless observed. Dibenzofuran derivatives were significantly more abundant in extracts derived from inertinite concentrate than in liptinite or vitrinite extracts. Within the retention time interval where dibenzofuran and its derivatives were identified in inertinite extracts, products prepared from liptinite and vitrinite concentrates were found primarily to contain biphenyls and acenaphthene derivatives. Extract fractions from inertinite were also characterized by almost negligible contents of phenol derivatives, a class of compounds much in evidence in the liptinite and vitrinite extract fractions. These findings have suggested some differences between oxygen functionalities in, and types of chemical bonds connecting, basic structural units in different coal macerals. Basic structural units in inertinites appear to be joined more frequently by alkyl or other bridges than by linear ether bonds, in comparison with other maceral groups. This provides one likely structural explanation for the relatively low yields obtained during the liquefaction of the inertinite concentrate.

Dependence of the liquefaction behaviour of some high-sulphur Turkish lignites on their properties

The liquefaction potential of seven high sulphur lignite samples from Middle, Western and Northwestern Anatolia were investigated by hydrogen-donor solvent extraction. The dependence of the conversion and individual fractions and gas yields on their properties are discussed. The lignites, especially those with high sulphur and volatile matter contents, were found to be suitable for liquefaction. By the application of simple linear regression, total sulphur content alone is observed to be a very good measure of the total benzene-soluble extract yield, the correlation coefficient of the regression, r, being equal to 0.99. Similarly, the hexane-soluble extract and the preasphaltene yields could best be predicted by regressions based on the pyritic sulphur content ( r=0.98) and the H/C atomic ratio ( r=0.96), respectively. The property of the lignites that explains the variations in the gas yield best is observed to be their carbon content ( r = −0.81). While no single property gives a strong correlation with asphaltene yield, volatile carbon content is still the best among the others. Geological homogeneity of our sample set is implied by these strong correlations.