Lipophilic extractives of the inner and outer barks from six different Pinus species grown in Indonesia

The chemical compositions of the dichloromethane extracts of inner and outer barks from six Pinus species（P.elliotii,P.oocarpa,P.caribeae,P.merkusii,P.montezumae,and P.insularis） grown in Indonesia were investigated by GC and GC–MS.Generally,the amounts of extractive contents were higher in the inner bark than in the outer bark except for P.merksuii.Fatty acids,monoterpenes,sesquiterpenes,resin acids,triterpenoids,and steroids were detected and quantified.Inner and outer barks differed not only in content of these compounds but also in their composition.Fatty acids and alcohols were the major classes of lipophilic compounds in the outer bark of P.caribeae, P.insularis,and P.montezumae.Steroids and triterpenoids were the dominant compounds identified in the inner bark of P.elliotii,P.insularis,and P.merkusii.Resin acids were the most abundant group in the inner bark of P.oocarpa whereas monoterpenes and sesquiterpenes were recorded in minor quantities in both bark layers of all species.

Theoretical and experimental study on lipophilicity and wound healing activity of ginger compounds

Objective:To correlate the chromatographic and computational method to calculate lipophilicity of selected ginger compounds and to observe the effects of log P on wound healing.Methods:Mixtures of acetonitrile and water with acetonitrile content between 95%and 50%v/v in 5%increments were kept separately in 10 different chromatographic chambers,saturated with solvent for 2 h.Spots were observed under UV light atλ=254 nm p-anisaldehyde used as a spraying reagent Theoretical calculation was done using the Alogps 2.1 online program at www.vcclab.org/lab/alogps.For percentage wound contraction,five groups of animal(mice)(25-30 g)of either sex were selected.Wound were created on dorsal surface of animals using toothed forceps,scalpel and pointed scissors.The wound areas were calculated using vernier caliper.After making wound mice were orally administered 35 mg/kg 6-shogoal,6-gingerol,8-gingerol and 10-gingerol respectively.Croup E as the control group received tap water.Results:The Iipophilicity values determined in thin layer chromatography were correlated with the theoretically calculated various log P by linear regression analysis.Significant correlations were found between log P values calculated by software program and the experimental reversedphase thin-layer chromatography data.Order of wound healing property of ginger compounds is directly dependent on lipophilieity i.e.more lipophilic compound has highest activity.Conclusions:Experimentally determined lipophilieity(R_(MO))values were correlated with log P determined by software's and found satisfactory.Lipophilieity(R_(MO)is a useful parameter for the determination and prediction of biological activity of ginger compounds.

Determination of hydrophilic–lipophilic balance value and emulsion properties of sacha inchi oil

Objective: To determine hydrophilic–lipophilic balance(HLB) value, stability of formulate emulsion and properties of sacha inchi oil.Methods: The physiochemical characteristics of sacha inchi oil were first investigated.Free radical scavenging property was studied by DPPH assay. HLB value of sacha inchi oil was experimentally determined by preparing the emulsion using emulsifiers at different HLB value. Sacha inchi oil emulsion was prepared using the obtained HLB and its stability was conducted by centrifugation, temperature cycling, and accelerated stability test. The efficiency of the prepared emulsion was clinically investigated by 15 volunteers. The primary skin irritation was performed using closed patch test. Subjective sensory assessment was evaluated by using 5-point hedonic scale method.Results: Peroxide value of sacha inchi oil was 18.40 meq O2/kg oil and acid value was1.86 KOH/g oil. The major fatty acids are omega-3(44%), omega-6(35%) and omega-9(9%). The vitamin E content was 226 mg/100 g oil. Moreover, sacha inchi oil(167 ppm)and its emulsion showed 85% and 89% DPPH inhibition, respectively. The experimental HLB value of sacha inchi oil was 8.5. The sacha inchi oil emulsion exhibited good stability after stability test. The emulsion was classified as non-irritant after tested by primary skin irritation method. The skin hydration value significantly increased from38.59 to 45.21(P < 0.05) after applying sacha inchi oil emulsion for 1 month and the overall product satisfaction of volunteers after use was with score of 4.2.Conclusions: This work provides information on HLB value and emulsion properties of sacha inchi oil which is useful for cosmetic and pharmaceutical application.

Quantum Chemistry Prediction of Molecular Lipophilicity Using Semi-Empirical AM1 and <i>Ab Initio</i>HF/6-311++G Levels

Reliable prediction of lipophilicity in organic compounds involves molecular descriptors determination. In this work, the lipophilicity of a set of twenty-three molecules has been determined using up to eleven quantum various descriptors calculated by means of quantum chemistry methods. According to Quantitative Structure Property Relationship (QSPR) methods, a first set of fourteen molecules was used as training set whereas a second set of nine molecules was used as test set. Calculations made at AM1 and HF/6-311++G theories levels have led to establish a QSPR relation able to predict molecular lipophilicity with over 95% confidence.

Evaluation of CC2 as a Decontaminant in Various Hydrophilicand Lipophilic Formulations Against Sulphur Mustard

Objective To evaluate CC2 (N, N’-dichloro-bis [2, 4, 6-trichlorophenyl] urea) invarious hydrophilic and lipophilic formulations as a personnel decontaminant for sulphurmustard (SM). Methods Twenty percent of CC2 was prepared as a suspension or ointmentwith various chemical agents and its stability was evaluated by active chlorine assay. Theefficacy was evaluated in mice by recording the mortality after applying 29 LD50 of SM (LD50 =8.1 mg/kg dermally) and decontaminating it after 2 min with 200 mg of the formulation.Studies were also carried out with 10% and 20% CC2 in acacia and hydroxypropyl cellulose,and the suspensions were stored in polyethylene containers. The stability of the suspensionswas evaluated by active chlorine assay. The efficacy was evaluated by recording themortality after applying 29 LD50 of SM in mice and 12 LD50 of SM in rats (LD50 = 2.4 mg/kgdermally), and decontaminating it with the formulations. LD50 by different routes andprimary skin irritation test of CC2 were also carried out. Results CC2 reacted with peanutoil and neem oil, and was unstable in povidone iodine and Fuller’s earth. Good stability wasachieved with petroleum jelly, honey, polyvinyl pyrrolidone, calamine lotion, acacia andhydroxypropyl cellulose. Though CC2 was stable in lipophilic formulations, it did notprotect the animals. The hydrophilic formulations particularly acacia and hydroxypropylcellulose gave very good protection and was stable in the polyethylene containers for aperiod of 1 year. The efficacy of 20% CC2 was better than 10% CC2. The oral and dermalLD50 of CC2 was found to be above 5.0 g/kg. CC2 was also found to be nonirritant.Conclusion Twenty percent of CC2 in hydroxypropyl cellulose is better with respect tostability, efficacy and ease of decontamination. CC2 is also a safe chemical.

Spatial variation of lipophilic marine algal toxins and its relationship with physicochemical parameters in spring in Laizhou Bay,China

Lipophilic marine algal toxins(LMATs)are produced by some toxigenic microalgae,which pose a serious threat to marine ecosystem and even human health.The occurrence and environmental control factors of LMATs in the surface seawater and phytoplankton in spring in Laizhou Bay in which Huanghe(Yellow)River estuary is included,in Shandong,East China were investigated.Okadaic acid(OA),pectenotoxin-2(PTX2),dinophysistoxin-1(DTX1),pectenotoxin-2 seco acid(PTX2 SA),DTX2,7-epi-PTX2 SA,PTX11,and 13-desmethyl spirolide C(SPX1)were detected from the surface seawater samples,and PTX2,7-epi-PTX2 SA,OA,DTX2,DTX1,PTX2 SA,and PTX11 were discovered in the phytoplankton samples showed a decreasing trend.The concentrations of∑LMATs in the seawater and phytoplankton ranged 2.03-74.38 ng/L on average of 13.72 ng/L and 0.98-479.27 pg/L on average of 50.20 pg/L,respectively.The joint influence of terrigenous input and internal circulation could promote the growth,toxin production,and toxin release of toxin-producing algae,leading to a higher content of LMATs in the bay nearby the Huanghe River estuary in both seawater and phytoplankton.The concentration of LMATs in spring was higher than that in summer,showing obvious seasonal variation.In addition,no significant correlation between most of the physiochemical parameters and LMAT contents in seawater was revealed by correlation analysis except for the positive correlation between DTX2 and chlorophyll a,OA and NH4-N.However,the increase of dissolved inorganic nitrogen content in seawater could enhance the production of OA,DTX1,and DTX2 in phytoplankton due probably to that the inorganic N input could benefit the growth and stimulate toxin production of toxin-producing algae.The result also proved that some PTX2 may be originated from Procentrum spp.and OA,DTXs and part of PTX2 may be originated from Dinophysis spp.

Screening for lipophilic marine toxins and their potential producers in coastal waters of Weihai in autumn,2020

Lipophilic marine toxins(LMTs)produced by some microalgae in the sea could accumulate in shellfish and pose potential threats to the health of seafood consumers.Phytoplankton and shellfish samples were collected from coastal waters of Weihai in Shandong Peninsula,China in autumn,2020,and screened for lipophilic marine toxins and their potential producers using liquid chromatography-tandem mass spectrometry(LC-MS/MS)analysis and high throughput sequencing of partial DNA(V4 region of the 18S rRNA gene)extracted from phytoplankton.Pectenotoxin-2(PTX2),trace amounts of azaspiracid(AZA1 or AZA40),and 13-desmethyl spirolide C(13-DesMe-C)were detected in phytoplankton samples,while PTX2 and gymnodimine(GYM)were detected in shellfish samples.The toxin content in shellfish samples was much lower than the regulatory limit or values reported previously.Results suggest that lipophilic marine toxins should have low risk in coastal waters of Weihai in autumn.Based on the data of high throughput sequencing,the OTUs were assigned to 5 identified species of Alexandrium,including A.ostenfeldii capable of producing 13-DesMe-C and GYM.Two OTUs were found closely related to the toxic species in genus Dinophysis,but it is impossible to assign them to any identified species due to the low resolving power of the V4 region for Dinophysis.The OTUs could not be assigned to any identified species in the genus Azadinium,suggesting the existence of unidentified species in this region.

A new lipophilic monosaccharide from Erigeron annuus

A new lipophilic monosaccharide, erigearide A （1）, was isolated from the aerial parts of Erigeron annuus （Lima.） Pers. Its structure was elucidated by analysis of spectroscopic evidence.

Acid-base and lipophilic properties of peptide nucleic acid derivatives

The first combined experimental and theoretical study on the ionization and lipophilic properties of peptide nucleic acid(PNA)derivatives,including eleven PNA monomers and two PNA decamers,is described.The acidity constants(pKa)of individual acidic and basic centers of PNA monomers were measured by automated potentiometric pH titrations in water/methanol solution,and these values were found to be in agreement with those obtained by MoKa software.These results indicate that single nucleobases do not change their pKa values when included in PNA monomers and oligomers.In addition,immobilized artificial membrane chromatography was employed to evaluate the lipophilic properties of PNA monomers and oligomers,which showed the PNA derivatives had poor affinity towards membrane phospholipids,and confirmed their scarce cell penetrating ability.Overall,our study not only is of potential relevance to evaluate the pharmacokinetic properties of PNA,but also constitutes a reliable basis to properly modify PNA to obtain mimics with enhanced cell penetration properties.

Oily Wastewater Treatment by Porous Ceramics Mediums with Surface Lipophilic Modification

Aiming at the treatment of difficult-to-handle oily wastewater, the ceramics filter mediums made from the iron and steel plant sludge were adopted to surface lipophilic modification so as to remove oil efficiently. The hydrolysis technique by FTIR and conductivity test indicated that under acid conditions hydrogen silicon oil did not hydrolyze but release hydrogen by chemical reaction under alkaline conditions. The results of the experiments including contact angle measurement, FTIR analysis, and SEM analysis illustrate that a layer of lipophile coating indeed exists evenly on the surface of filter mediums after modification. Furthermore, the hydrogen-containing silicone oil was combined through dehydration of Si-H bond with the-OH on the surface of ceramic filter medium.

Sulfonated carbon materials with hydrophilic and lipophilic properties

Two acidic carbon materials （H-PRC and HS-C） were used as catalysts for the condensation reaction of methanol with formaldehyde to produce dimethoxymethane （DMM） in aqueous solution （hydrophilic system） and for the etherification of isopentene with methanol to produce tert amyl methyl ether （TAME） in toluene solution （lipophilic system）. Microcalorimetric adsorptions of water and benzene showed that the HS-C was highly hydrophilic without the lipophilicity, while the H-PRC exhibited both the hydrophilicity and lipophilicity. Thus, the HS-C was well dispersed in aqueous solution and difficult to separate from it. On the other hand, the H-PRC was highly active, more active than the acidic resin （D008） and sulfuric acid, for the synthesis of DMM in aqueous solution. The H-PRC was also highly active, more active than the HS-C, for the etherification of isopentene with methanol to produce TAME in toluene solution, probably owing to its amphiphilic surface property as well as its strong surface acidity as measured by the microcalorirnetric adsorption of NH3.

Lipophilic Optical Supramolecular Nano Devices in the Aqueous Phase

Nano micelles of sodium dodecyl sulphate in water were prepared as local lipophilic media for the organisation of interacting chromophores. Such arrangements were controlled by peripheric substituents to operate either as isolated chromophores or as skew oriented pairs where H-type transitions cause hysochromic absorption and J-type transitions bathochromic fluorescence. As a consequence, large Stokes' shift could be obtained.

The Presence of Phases and the Inability of the Classical Compartment Models to Provide Pharmacokinetic Parameters of Physiological Significance for Lipophilic Drugs

The first biphasic open one-compartment pharmacokinetic model is described. Its analytical solutions to drug concentration were developed from parameters of an open two-compartment pharmacokinetic model. The model is used to explain the unusually large compartment volumes and apparent volumes of distribution of lipophilic drugs, as well as to identify which of the pharmacokinetic parameters of the classical compartment models are biologically relevant.

Activity Trends in Desoxy Anthrapyrazoles: The Influence of Molar Volume, Polarizability and Lipophilicity of N₂C₅Side Chains on Their Anticancer Response

QSAR methodology was used to assess the effects of lipophilicity (logP), molar volume (MV) and polarizability (pl) of the side chains at N2 and C5 of 20 known desoxy anthrapyrazoles on their in vitro anticancer activity expressed as the negative logarithm of the inhibitory concentration of 50% of L1210 murine leukemia cell line (1/logIC50). The main data set shows poor correlations between biological response and the descriptors with exception of MV of the C5 side chain, where a moderate correlation was discerned ( =0.60, n = 18, two outliers). To extract more information regarding mechanism, the main data set was visually classified to three clusters depending on N2 side chain. Cluster 1 containing six 5-substituted 2-[(2-hydroxyethyl) amino] ethyl anthrapyrazoles;cluster 2 contains ten 5-subsitutes 2-(diethyl amino) ethyl anthrapyrazoles and cluster 3 contains four anthrapyrazoles with miscellaneous substituents at both N2 and C5. For cluster 1, MV and pl of C5 show high correlation with biological response (R2’s = 0.75 and 0.72 respectively) while logP gives a weak correlation (R2 = 0.44). For cluster 2, the correlations of logP and pl of C2side chain are higher (=0.66 and 0.62 respectively) compared with MV (=0.16). Cluster 3 shows very poor correlation with all descriptors (~0.3). This indicates mechanistic distinction between the three clusters. Derived descriptors which represent the difference between the descriptors of N2 and C5 side chains where used to explore the presence of interplay between these descriptors in affecting variability of the biological response.

Catalytic Hydrolysis of Lipophilic Amino Acid Esters by Metallomicelles as Carboxypeptidase A Models

Lipophilic complexes of macrocyclic 12-membered dioxotetraamine ligand bearing bis-hydroxy groups as functional pendants are effective catalysts for the hydrolysis of amino acid esters in micellar media, and the rate enhancement of more than 10-fold were observed.

Studies on the Synthesis,the 2D and 3D-QSAR About Lipophilic Antifolate 2,4-Diamino-5-methyl-6-(Substituted Benzylamino) Quinazoline Compounds

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Preparation and characterization of a novel adsorbent for removing lipophilic organic from water

A novel composite adsorbent containing a kind of lipid-triolein is studied. The ad-sorbent is prepared by embedding triolein into cellulose acetate (CA) sphere. The preparation method, the physical-chemical properties of the adsorbent and the removal efficiency of two or-ganochlorinated pesticides are studied. The adsorbent is stable in water and no triolein leaks into water for 465 h soaking. The adsorbent has high adsorption capacity for organochlorinated pes-ticides such as dieldrin and aldrin. The results suggest that triolein-containing adsorbent could serve as a good adsorbent for lipophilic organic pollutants. The adsorption rate for lipophilic pol-lutants is very fast and has relation with the logKow of the compounds.

Integrating of lipophilic platinum(IV) prodrug into liposomes for cancer therapy on patient-derived xenograft model

Platinum-based anticancer agents such as cisplatin and its analogues are widely used for treating multiple cancers. However, due to the inferior water-solubility, chemoresistance and consequent adverse side effects, their clinical applications are limited. Herein, choles Pt(IV), a lipophilic platinum(IV) prodrug was synthesized for manufacture of Choles Pt(IV)-Liposomes aiming to resolve the predefined obstacles encountered by platinum drugs. Following systematic screening, Choles Pt(IV)-Liposomes showed a small particle size(105.6 nm), the rapid release of platinum(Pt) ions, and notable apoptosis of cancer cells.In addition, according to the fluidity and safety results of animal experiments in mice, Choles Pt(IV)-Liposomes also showed better therapeutic effect, which significantly inhibited the growth of patientderived xenograft tumors of hepatocellular carcinoma with an inhibition ratio of 80.7%, and effectively alleviated the drug toxicity brought by traditional platinum drugs. Overall, this study provides a promising route to enhance the therapeutic efficiency of platinum drugs in cancer treatment.

Isolation and Purification of a Novel Long-chain Acyl Catechin from Lipophilic Tea Polyphenols

Lipophilic tea polyphenols (LTP) was prepared by esterification of green tea polyphenols (GTP) with hexadecanoyl chloride. A novel long-chain acyl catechin was isolated and purified from LTP by high-speed countercurrent chromatography (HSCCC). Its molecular structure was elucidated as epigallocatechin-3-O-gallate-4'-O-hexadecanate by elemental analysis, IR, MS and H-1 NMR spectra.

Antioxidant interactions between hydrophilic and lipophilic phytochemicals are influenced by their ratios and total concentrations

Lipophilic(lycopene,β-carotene)and hydrophilic(caffeic acid,p-coumaric acid)phytochemicals were mixed in molar mass at different concentrations/ratios to explore the antioxidant interactions on H_(2)O_(2)-treated H9c2 cells.Reactive oxide species(ROS),expression of antioxidant enzymes,and oxidation products were analyzed and evaluated by synergistic rate(SR)and combination index(CI).At constant concentrations,antioxidant interactions were influenced by ratios.Group contained more hydrophilic compounds(eg.,p-coumaric acid:β-carotene=9:1)showed antioxidant synergism(SR=22.33±1.23,SR>0)at 3.0μM,while groups that contained more lipophilic compounds(eg.,p-coumaric acid:β-carotene=1:9)showed antioxidant antagonism(SR=-11.68±1.25,SR<0)at 3.0μM.Antioxidant interactions were also influenced by concentrations.From results,ROS generation of group(p-coumaric acid:β-carotene=1:9)changed from synergism(SR=12.27±2.34,SR>0)to antagonism(SR=-11.68±1.25,SR<0)as their total concentrations increased from 1.5μM to 3.0μM.Therefore,this study discussed the possible mechanism of ratio and concentration on the antioxidant interaction among hydrophilic and lipophilic phytochemicals.It also suggested that proper concentrations/ratios of hydrophilic and lipophilic phytochemicals should be considered in diet and formulation of functional foods.