Ether-soluble Components Research Articles

New triterpenoids and sterol with potent cytotoxic activity from Justicia simplex – Isolation, characterisation and biological evaluation

Justicia is the largest genus of Acanthaceae family with nearly 600 species. Approximately eighteen species were chemically and biologically studied. Attempts were made to isolate, characterize and study the cytotoxic properties of three-petrol ether soluble components namely Methyl-(3β)-3, 23 dihydroxy olean-12-en-28-oate, 3β (Valeryloxy) olean-5,12-dien-1β, 11α, 28β -triol and Stigmasta-5, 20-dien-3β -yl undecanoates were isolated for the first time from this plant. The in vitro antiproliferative potential was assessed against MCF-7 and HeLa cells using MTT assay. 3β (Valeryloxy) olean-5,12-dien-1β, 11α, 28β -triol exhibited cytotoxicity in vitro with an IC50 value of 20.55 and 22.14 µg/mL for HeLa and MCF-7 cell lines respectively, which may be attributed to its apoptotic potential. Apoptotic property of the compounds was confirmed by the Ethidium bromide and Acridine orange double staining methods. 3β (Valeryloxy) olean-5,12-dien-1 β,11 α, 28β -triol revealed better apoptotic activity. Antitumor activity was evaluated by Daltons Lymphoma Ascites induced solid tumour model. Petrol ether extract of Justicia simplex at a dose of 200 mg/kg was capable of producing 71.74% of tumour inhibition. The newly isolated ester derivative of hederagenin and stigmasterol exhibited better cytotoxicity than the earlier reported compounds

English

This study aimed to investigate the ameliorative effect of the petroleum ether extract ofSemen cuscutae (SCPEE) on β-estradiol 3-benzoate (EB) induced kidney-yang deficiency (KD) by using an animal model. This model was established by daily intraperitoneal injection of EB (4 mg/kg) to ICR male mice for 15 days. To evaluate the SCPEE effect, after the first EB injection, the mice were orally administrated daily by SCPEE (10 ml/kg), and their physiological, kinematic, histological, and biochemical parameters were assessed at the beginning (Day 0) and the end (Day 15) of the experiment. The results showed that the EB injection could induce typical KD symptoms including physiological, kinematic and biochemical disorders of the mice. After SCPEE administration, a positive response against these symptoms was observed, and most of the disorders were recovered completely. This is the first report to demonstrate the significant anti-KD effect of SCPEE, indicating the ether-soluble components of S. cuscutae may have a potential clinical value for KD treatment.   Key words: Semen cuscutae, kidney-yang deficiency, traditional Chinese medicine, β-estradiol 3-benzoate, petroleum ether.

ワカメ中のエーテル可溶物の分析

The analysis of components in algae is an important research subject in the fields of food, perfume, and medicinal chemistry because they have characteristic odors and unique structures different from those found in land plants. A systematic analysis of the ether soluble components in Undaria pinnatifida was therefore conducted. The sample was soaked in methanol for one week and the methanol extract was treated with ether in order to remove mannitol. The resulting ether soluble components were then separated and purified by a silica gel column and/or preparative thin layer chromatography. Compounds of hydrocarbons (paraffins, polyolefins), methyl and phytyl esters of fatty acids, long chain aldehydes, and sterols were isolated. Most of these compounds have been found in algae preciously, but some were recognized for the first time in U. pinnatifida.

Polyethylene and elastomeric polypropylene using alumina‐supported bis(arene) titanium, zirconium, and hafnium catalysts

AbstractBis(arene) complexes of zerovalent titanium, zirconium, and hafnium supported on partially dehydroxylated, fumed alumina are effective catalysts for the polymerization of olefins. The zerovalent complexes react with surface hydroxyls with loss of one equivalent of arene to yield the active species. The polyethylenes derived from these catalysts are very high molecular weight. Polymerization of propylene yields elastomeric stereoblock polymers which are composed of isotactic and stereoirregular sequences. The polymers are stiffer than polypropylenes obtained with similar catalysts derived from tetra(neophyl)zirconium. The chain microstructures of the various components of the whole polymers have been characterized by 13C‐NMR and solvent extraction studies. The ether soluble component of these polymers is of a relatively high molecular weight and the microstructure of the backbone is largely stereoirregular. It is the cocrystallization of this fraction of the polymer with the crystalline, isotactic fractions which is critical to the observed elastomeric properties.

Foraging for Patchily-Distributed Leaf-Miners by the Parasitoid, Dapsilarthra rufiventris (Hymenoptera : Braconidae) : V. Plant Odour as a Cue to Long Range Patch-Location

By the Y-tube olfactometer test female adults of Dapsilarthra rufiventris, a larval parasitoid of a leaf-mining fly, Phytomyza ranunculi, were found to be attracted like female flies by odour of the fly's host plant, Ranunculus glaber. We studied the constituents of odour by a bioassay and an instrumental analysis of chemical extracts obtained by steam distillation and methanol-dipping of plants. Females of both fly and parasitoid were attracted to ether-soluble components excluding hydrocarbon, i.e., protoanemonin, anemonin and/or fatty acids, of steam volatile oil and extracts of methanol dipping in the plant.

Interactions of tamoxifen in the chicken

The triphenylethylene antiestrogens are very potent antagonists of estrogen action in the chicken and manifest little agonist activity compared to their action in other species. The estrogen antagonism is most probably mediated by the estrogen receptor, to which tamoxifen binds with a K i of 2.6 nM. Tamoxifen is readily metabolized by liver to 4-hydroxytamoxifen, which binds the liver nuclear estrogen receptor with a K i , of 0.1 nM. The K d of the receptor is 0.7 nM. Estrogen receptor concentrations in liver from immature chickens are relatively low both in nuclear and cytosol fractions. Treatment with estradiol results in 10-fold up-regulation of the nuclear levels to give a total receptor concentration of about 2 pmol/g tissue. Tamoxifen can promote this up-regulation to a limited extent, but interpretation of experimental results is compromised by difficulties with exchange assays in the face of the very high binding affinity of 4-hydroxytamoxifen. Tamoxifen also binds with high affinity ( K d 2–4 nM) and distinctive specificity to antiestrogen binding sites (AEBS) present in a wide variety of chicken tissues and in the highest concentration in the liver (800 pmol/g tissue). Liver and serum contain ether-soluble components which can compete for binding of [ 3H]tamoxifen to the AEBS. The serum AEBS inhibitory activity is chromatographically heterogeneous and is associated with a sterol-like fraction as well as with a fatty-acid-containing fraction. Tamoxifen treatment of cockerels results in dose- and time-dependent decreases in serum free and esterified cholesterol, and in phospholipids and triglycerides. These changes may reflect estrogenreceptor-independent interactions of tamoxifen.

Studies on components of the chloroform-methanol extract from Madurella grisea.

Some of the lipids described in many fungi were found in Madurella grisea, in addition to other diethyl ether-soluble components with peculiar characteristics. One fraction structurally related to ethane diol (ethylene glycol) accounted for about 41% and a compound identified as methyl terephthalate represented about 38% of the extract. No steroids were detected. The absence of these lipids may perhaps explain the resistance of this organism to polyene antibiotics.

Oviposition markers in Callosobruchus maculatus F. and Callosobruchus rhodesianus pic. (coleoptera, bruchidae): Assymmetry of interspecific responses

The bean weevils Callosobruchus maculatus (F.) and C. rhodesianus (Pic.) both laid fewer eggs on previously infested adzuki beans than on fresh beans, even after eggs were removed. A variety of experimental treatments demonstrated the existence of an oviposition marker with ether soluble components. Callosobruchus rhodesianus was inhibited from ovipositing by the C. maculatus marker, but not vice versa.

Haemolymph lipid transport from fat body to uterine gland in pregnant females of Glossina morsitans

Haemolymph volume of the female tsetse fly, Glossina morsitans morsitans remains constant for at least 24 hr following ingestion of a blood meal but increases progressively from 4.5 to 7.5 μl during pregnancy, falling rapidly to its original volume on the day of parturition. During this time the haemolymph total lipid (i.e. ethanol: ether soluble components) concentration remains between 5.8 and 7.6 μg/μl. The proportion of haemolymph lipid identified as 1,2-diglyceride is also relatively constant at 18–24% of the total, but following haemocoelic injection of [U- 14C]-leucine in early pregnancy becomes increasingly radioactive as pregnancy proceeds. Pulse-labelling of the haemolymph with [U- 14C]-palmitate indicates a faster turnover rate of diglyceride in late pregnancy than in early pregnancy with peak incorporation times of 8 and 25 min respectively. A haemolymph lipoprotein carrying radio-labelled diglyceride has been isolated. Results suggest that haemolymph diglycerides constitute an important lipid transport form for the rapid transfer of stored triglyceride from the fat body to the uterine gland where ‘larval milk’ is synthesized and fed in utero to the growing larva. Owing to the competition among a variety of metabolic pathways for injected free fatty acid, it is considered that accurate estimates of haemolymph diglyceride turnover rate will require pulse labelling with radioactive diglyceride.

Comparison of Aerosol at Four Baseline Atmospheric Monitoring Stations

Abstract Particles were captured by electrostatic precipitators or impactors at atmospheric monitoring bases in Alaska, Hawaii, Tasmania and Antarctica, and examined by electron microscopy. Particle number and mass distributions for radii ≲0.06 μm were similar at all sites. The particles appeared to be composed mainly of sulfuric acid (Alaska and Hawaii) or ammonium sulfate (Tasmania and Antarctica). Those of larger size showed marked differences in concentration size distribution and composition at the four sites. Those in Alaska differed from the remainder in that more than half contained insoluble inclusions and almost all particles were coated with, or wholly composed of, sulfuric acid. The Tasmanian aerosol was dominated by sea salt for particles with r > 0.1 μm, and many but not all of the micron-sized particles had benzene-soluble or ether-soluble components. At all except the Tasmanian site a maximum occurred in the mass distribution curve at a radius of ∼0.3 μm, and it is suggested that this is d...

Effects of flag leaf axial lesions caused by Septoria nodorum on 14C translocation and yield of wheat

Wheat flag leaves having axial lesions caused by infection with Septoria nodorum were studied to determine how grain yield was affected and whether there was interference with translocation of carbohydrate. Kernel yield was reduced less than 5% when the axil and sheath of the flag leaf were the only tissues infected. When all leaves except the flag leaf were removed, kernel yield was reduced 14%, and when all leaves were removed, the reduction was 19%. After administration of glucose-U- 14C, translocation of 14C from the flag-leaf lamina to the developing kernels was not impeded; rather, in some instances, it was enhanced by infection with Septoria. In addition, glucose- 14C was metabolized more readily to ether-soluble components in infected tissue than in control tissue. Because axial lesions did not interfere with translocation of assimilates, the yield damage must have been caused by interference with other metabolic functions.

Study on the components of musk. I. Ether soluble components.

Ether soluble components of musk have been investigated by chromatographic and spectroscopic methods. As indicated in the list of identified constituents (Table II), they were proved to be predominantly steroidal : eleven androstane derivatives, cholesterol and its esters, and cholest-4-en-3-one, in addition to wax and muscone. Characteristic feature of cholesterol esters and wax was that they are the esters derived from very long chain fatty acids of C14 through C40 in which branched ones were predominant except C16 and C18. Wax alcohols were found to have almost exclusively branched chain (C20 to C34).

Studies on Soda Oxygen Pulping of Wood

In order to obtain more detailed information concerning the degradation of lignin in the oxygen-alkali cooking, the milled wood lignin from Japanese red pine (Pinns densiflora) was cooked with the alkaline liquor of various pH values containing NaOH and NaHCO3 in the presence of oxygen under the conditions shown in Table 1. The reaction mixtures thus obtained were studied for the fractionation curve of the gel filtration, UV-absorption spectrum, weak-acidic dissociation group, COD, and BOD (cf. Fig. 14 and Table 2). Furthermore, the ether-soluble fraction of the reaction products was studied by means of gas-liquid and thin-layer chromatographies (cf. Table 3 and Fig. 6). Main results are as follows : 1. When cooked the lignin with alkaline liquor adjusted to pH 13.5 in the presence of oxygen, a small amount of lignin fraction having lower molecular weight was formed even in the cooking at 70°C, and the higher the cooking temperature was, the lower molecular weight the lignin degraded into and the larger number of weak-acidic dissociation group the degraded lignin had. 2. In the case of the alkaline liquor of pH 8.5, even in the cooking at a higher temperature viz. 120 to 140°C, some of lignin having high molecular weight remained without degradation. 3. The BOD/COD ratio of the cooking mixture with alkaline liquor of pH 13.5 at a temperature of 120 to 140°C was 0.61 to 0.71, and much higher than that of the cooking mixture with the liquor of lower pH value, suggesting that lignin fraction in the waste liquor of the oxygen-alkali cooking at a high pH probably can be decomposed more easily by micro-biological treatment than can the lignin fraction in waste liquor of the ordinary alkali cooking. 4. The yields of the ether-soluble components were as listed in Table 3. Among the degradation products in the oxygen-alkali cooking with alkaline liquor of pH 13.5, methanol was in the highest yield, and acetic acid and formic acid were in comparatively high yield. It was remarkable that, in the oxydation products of the milled wood lignin, a small amount of acetone was found in addition to the aromatic and aliphatic compounds which have already been reported as the oxydation products of lignin. The above mentioned results indicate that the degradation reaction of lignin during the oxygen-alkali cooking is markedly affected by pH value of the cooking liquor.

The Relative Amounts and Identification of Some 2,4-Dichlorophenoxyacetic Acid Metabolites Isolated from Soybean Cotyledon Callus Cultures

Soybean (Glycine max L.) cotyledon callus grown on radioactive 2,4-dichlorophenoxyacetic acid (2,4-D-1-(14)C) as an auxin produced 2,4-D metabolites, which qualitatively and quantitatively changed with time. Water soluble fractions from the tissue exhibited a steady increase in radioactivity during the course of 24 days. Following beta-glucosidase treatment, at least eight aglycones were obtained from the water soluble fraction of the tissue after 8 days. The metabolite, 4-hydroxy-2,5-dichlorophenoxyacetic acid was the most abundant aglycone during the entire 32 day growth period while 4-hydroxy-2,3-dichlorophenoxyacetic acid was detected as a minor metabolite. Radioactivity in the ether soluble acidic fractions reached a maximum of 82% of the total in the tissue after 2 days. The level then decreased to 44% by the end of 24 days. A total of seven ether soluble components were detected. In addition to 2,4-D glutamic acid, which was detected in high amounts after 24 hours, 2,4-D aspartic acid was found to be the most abundant ether soluble metabolite after longer time periods. Mass spectral data and a fragmentation pattern are presented for 2,4-D aspartic acid.

Carbohydrate and Lipid Metabolism During Germination of Uredospores of Puccinia graminis tritici

Uredospores of Puccinia graminis (Pers.) tritici (Eriks. and Henn.) were uniformly labeled with (14)C by permitting the host (Triticum aestivum L.) to carry out photosynthesis in (14)CO(2) during the process of spore production by the obligate parasite. The use of (14)C labeled spores provided advantages in a study of the utilization of endogenous substrates at frequent intervals with small amounts of spores under conditions conducive to germination.Because of previous uncertainties about the nature of the substrates of importance to germination, a detailed study of carbohydrate and lipid components, both in the spores and in the germination medium, was made during the first 7 hours after placing the spores on aqueous media. Diethyl ether and 80% ethanol soluble metabolites each constituted approximately 20% of the total spore carbon. During the first hour nearly 60% of the 80% alcohol solubles disappeared from the spores while the total ether soluble material did not change appreciably. A significant part of the 80% ethanol soluble materials appeared in the germination medium.During germination and germ tube extension, there was rapid utilization of trehalose, arabitol and mannitol even though appreciable amounts of these materials were present as exogenous pools in the germination medium. Although the total amounts of ether soluble components did not change as drastically as the carbohydrate fraction, there was extensive utilization of palmitic, oleic, linolenic and 9,10-epoxyoctadecanoic acids.The results indicate that the germination process in spores of obligate parasites is not based solely on the utilization of lipids and some possible roles of the changes in internal and external pools of soluble carbohydrates are discussed.

Growth Substances in the Roots ofVicia faba

An investigation has been made into the growth regulators present in ethanol extracts of the seedling roots of Vicia faba after separation on paper partition chromatograms, using segments of Avena coleoptiles and mesocotyls and of Pisum sativum roots as biological assay material. Acetonitrile purification shows the presence of at least three auxins running in isobutanol : methanol : water, at Rfs of 0-0-25, 0-4-0-6, and 0-65-0-95; the latter may represent two different auxins. A similar, but clearer, picture is shown by the ether-soluble acid fraction. Here an auxin at Rf 0-0 25 als° stimulates root growth and could be 'accelerator a.'. A second at Rf 0-35-0-65 is an indole compound which inhibits root growth and does not seem to be IAA. A third at Rf o-8-i -o is also a root-growth inhibitor and gives no indole reaction. The 'inhibitor i3' com plex was demonstrated (Rf 0-65-0-85) together with a number of other inhibitors at lower Rf value. The ether-soluble neutral component also contains auxins or auxin precursors. The water-soluble, ether-insoluble fraction contains four readily intercon vertible substances with auxin properties. They all appear to inhibit root growth and give no indole reaction.

The effect of illumination on the electrical conductance of rhodopsin solutions.

An apparatus was constructed in order to record continuously and simultaneously changes in extinction and electrical conductance of rhodopsin solutions. With this apparatus, changes in electrical conductance on exposing rhodopsin to light were investigated. On illumination solutions of rhodopsin revealed a conductance change so long as they preserved their photosensitivity. The conductance change begins almost immediately upon illumination and is almost proportional to the amount of rhodopsin decomposed, continuing until rhodopsin is converted to indicator yellow. Near pH 7 the conductance is apt to increase slightly, while it decreases considerably outside the range of pH 6-9, being accompanied by a pH change towards neutrality. The conductance change is regarded as an essential property of rhodopsin, because it occurs in aqueous suspension as well as in digitonin solution; it may be caused by hydrogen or hydroxyl ions and some other conductive substances. It is also noteworthy that the petroleum ether-soluble component of the rod outer segments-presumably the lipide-tends to increase the conductance change. In suspensions of rod outer segments and retinal homogenates, the conductance increases on illumination irrespective of pH: this may be due to secondary reactions following the photic reaction of rhodopsin. We shall discuss the significance of the conductance change in relation to the initiation of visual excitation.

Water and water vapor absorption of the stratum corneum of the living human skin.

On living human skin the water content and liquid water absorption of untreated stratum corneum and stratum corneum from which the water-, alcohol- and ether-soluble components were removed was det...

An antirachitic sulfonic acid derivative of cholesterol

A procedure is described for the preparation of an antirachitic sulfonic acid fraction from cholesterol. The ether-soluble component treated in benzene with brucine separated a crystalline brucine salt of an antirachitic steroid monosulfonic acid. Successive preparations had the same potency, and numerous recrystallizations did not change it. Separation of the disodium salt of a dicarboxylic acid, C 27H 38O 10Na 2, as the main product of the permanganate oxidation of the antirachitic sulfonic acid, is evidence of no cleavage of the sterol molecule, further substantiated by the perbenzoic acid reaction which indicated four double bonds.

ACTIVATION OF CAMBIAL GROWTH BY PURE HORMONES

IN a recent letter to NATURE1 it was reported that strong cambial growth can be activated in young decapitated sun-flower seedlings by inserting their upper ends into tubes containing a weak solution in gelatine of the ether-soluble component of urine. With a similar method it has now been found that strong cambial growth can be activated by solutions of pure auxin- and of pure-indolyl-acetic acid (called by Kogl2 hetero-auxin) at concentrations of 1 or 2 in 106. The auxin- was kindly sent by Prof. Kogl from Utrecht, and the hetero-auxin was kindly synthesised by Dr. Weisberger at the Dyson Perrins Laboratory, Oxford. The cambium formed was in the normal position, and it extended for at least three centimetres below the part to which the hormone was applied. Controls had formed no cambium, or scarcely any.