A review of the antioxidant potential of medicinal plant species

Some researchers suggest that two-thirds of the world's plant species have medicinal value; in particular, many medicinal plants have great antioxidant potential. Antioxidants reduce the oxidative stress in cells and are therefore useful in the treatment of many human diseases, including cancer, cardiovascular diseases and inflammatory diseases. This paper reviews the antioxidant potential of extracts from the stems, roots, bark, leaves, fruits and seeds of several important medicinal species. Synthetic antioxidants such as butylated hydroxytoluene (BHT) and butylated hydroxylanisole (BHA) are currently used as food additives, and many plant species have similar antioxidant potentials as these synthetics. These species include Diospyros abyssinica, Pistacia lentiscus, Geranium sanguineum L., Sargentodoxa cuneata Rehd. Et Wils, Polyalthia cerasoides (Roxb.) Bedd, Crataeva nurvala Buch-Ham., Acacia auriculiformis A. Cunn, Teucrium polium L., Dracocephalum moldavica L., Urtica dioica L., Ficus microcarpa L. fil., Bidens pilosa Linn. Radiata, Leea indica, the Lamiaceae species, Uncaria tomentosa (Willd.) DC, Salvia officinalis L., Momordica Charantia L., Rheum ribes L., and Pelargonium endlicherianum. The literature reveals that these natural antioxidants represent a potentially side effect-free alternative to synthetic antioxidants in the food processing industry and for use in preventive medicine.     

Enthalpies of vaporization of oligomers of poly(hexamethylene sebacate) and esters of alkylcarboxylic acids

Enthalpies of vaporization for esters covering a molecular weight range of about 74–939 g/mol · [monocarboxylics; linear esters of sebacic series; branched esters of triglyceride series; and, oligomer esters of poly(hexamethylene sebacate)] and a temperature range of about 273.15–523.15 K have been empirically fitted to within about 5% to an equation of the following form: ΔHv(T,M) = S(T)f(M) + I₀(T), where S(T) = C Ln(T) + K₀, I₀(T) = aT + b₀, and f(M) = M/(1 + a₀M), M is the molecular weight (molar mass); T is in degrees Kelvin; and, C, K₀, a, b₀, and a₀ are constants. These results were used to determine the heat capacity difference, ΔC_p = C_p(l) − C_p(g), and compared to calculated values from functional relationships of C_p(l) and C_p(g), l is liquid g is gas. The heat capacity difference results in conjunction with C_p(l) were used to empirically calculate the heat capacity of the gas, C_p(g), over the molecular weight and temperature ranges investigated and compared to a group contribution method. The functional forms for ΔHv(T,M), ΔC_p(T,M), C_p(l), and C_p(g) were also found to be applicable for n-alkanes. © 1998 John Wiley & Sons, Inc. J. Appl. Polym. Sci. 70: 731–746, 1998     

Identification of the sex pheromone of threeMatsucoccus pine bast scales

Matsucoccus resinosae in the United States,M. matsumurae in China, andM. thunbergianae in Korea use (2E, 4E)-4,6,10,12-tetramethyl-2,4-tridecadien-7-one (1) (matsuone) as the primary component of their sex attractant pheromones. The structure was postulated from mass and NMR spectra and confirmed by synthesis of analogs3, (2E,4E)-4,6,11,12-tetramethyl-2,4-tridecadien-7-one, and4, (2E,4Z)-4,6,11,12-tetramethyl-2,4-tridecadien-7-one. Both analogs were attractive to the males ofM. resinosae in laboratory bioassays and toM. matsumurae in laboratory and field tests, but the 4Z analog (4) was much less so than the 4E analog (3) and had inhibitory effects at high concentrations. Dodecanol, isolated from aeration and solvent extracts of femaleM. resinosae, evoked characteristic wing-raising by pedestrian males, but the role of this response was not determined.     

Kinetics of Adhesion Interaction of Polyolefins with Metals Under Conditions of Contact Thermooxidation

The development of peel strength of adhesive joints between a PE containing organic peroxide (dicumy1 peroxide) and steel has been studied. It has been found that the kinetics of this process are controlled by the contact oxidation processes in a thin boundary layer. The peel strength, A, as a function of the contact time, t, is determined by the content of dicumy1 peroxide, c _per, in the adhesive, contact temperature, T, and the content of oxygen in the contacting environment. The value of A reaches its maximum, A _max, at a certain contact time, t _Amax..

The kinetic characteristics A _max and t _Amax as well as the initial growth rate of A,A ^{= t}=0 = lim da/dt _t=0, are determined by c _per and T. There is a growth of A _max and A ⁼ _t=0 with c _per and a decrease of t _Amax with T.

The shape of A(t) curves for a peroxide-containing PE, similar to a pure PE, is defined by the competitive influence of two principal tendencies in contact oxidation: oxidative cross-linking inducing the growth of A and oxidative destruction causing the reduction of A. There is a growth of the output of contact oxidation reactions with the increase of c _per. The empirical constants of an equation describing the A(t)-functions are calculated and the efficiency of the use of peroxides for promoting the PE-adhesion is estimated.

It has been proved that the peel strength at a fixed contact time is determined by the ratio of the gel-fraction in the polymer layer, c _gel, which is a measure of the outcome of the oxidative cross-linking, and the content of extractable low-molecular products, C _Im, characterizing the effect of oxidative destruction.     

Detoxification of cereal plant allelochemicals by aphids: Activity and molecular weights of glutathioneS-transferase in three species of cereal aphids

The activity and molecular weights of glutathioneS-transferase were studied in three species of cereal aphid:Metopolophium dirhodum, Sitobion avenae, andRhopalosiphum padi. The highest level of glutathioneS-transferase activity was recorded in extracts fromM. dirhodum and the lowest fromS. avenae, and extracts of larvae were more active than those from adults. The activity of this enzyme was higher in extracts ofS. avenae andR. padi previously fed on a moderately resistant wheat variety than on a susceptible variety. Gel filtration followed by SDS-PAGE revealed three protein bands in the active fractions. The first had a molecular weight of 28,500 and the second of 27,500 and were present in all three species of aphid. The third protein differed in the three species, having a molecular weight of 26,000 inS. avenae, 25,500 inM. dirhodum, and 24,000 inR. padi.     

Allelochemical regulation of reproduction and seed germination of two BrazilianBaccharis species by phytotoxic trichothecenes

The potent phytotoxic trichothecene roridins and baccharinoids occur naturally in the Brazilian plants,Baccharis coridifolia andB. megapotamica. Biosynthesis of roridins inB. coridifolia appears to be linked to pollination, and the phytotoxins then accumulate in the seed. The roles of the phytotoxins in pollination, seed maturation, and germination of theBaccharis species were investigated. The high production of roridins occurred only in seeds resulting from intraspecific pollination, and the concentration of the toxins in the seeds generally increased with seed maturity. Removal of seed coats from trichothecene-producing BrazilianBaccharis species (B. coridifolia andB. megapotamica) and non-trichothecene-producing AmericanBaccharis species (B. halimifolia andB. glutinosa) resulted in improved seed germination ofB. halimifolia andB. glutinosa but complete inhibition of seed germination ofB. coridifolia andB. megapotamica. Addition of seed coat extracts of the BrazilianBaccharis species of dilute solutions (10^–6g/ml) of roridins or baccharinoids to the decoated seeds ofB. coridifolia andB. megapotamica resulted in germination, while seeds ofB. halimifolia andB. glutinosa were killed by the phytotoxins. Roridins interacted with gibberellic acid, a germination promoter, but not with abscisic acid, a germination inhibitor. The results from this study suggest that macrocyclic trichothecenes have a regulatory role(s) on reproduction and germination of BrazilianBaccharis species in their natural habitat.     

Dynamics of Algal Secondary Metabolites in Two Species of Sea Hare

The function of acquired algal secondary metabolites in sea hares is the subject of debate, in part because the dynamics/processing of metabolites by sea hares is poorly understood. This study investigates the dynamics of red algal secondary metabolites in two sea hares, Aplysia parvula and Aplysia dactylomela. Secondary metabolite levels were quantified for the dietary red algae Laurencia obtusa and Delisea pulchra and for sea hares collected from these seaweeds in the field. The patterns and dynamics of algal secondary metabolites were further investigated in the laboratory by quantitative analysis of secondary metabolites in sea hares grown on diets of L. obtusa, D. pulchra, or the green alga Ulva sp. Sea hares accumulated the most abundant metabolites from each red alga, the terpene palisadin A from L. obtusa, and the halogenated furanone 3 from D. pulchra, and stored a greater proportion of these metabolites than other algal metabolites. A. parvula accumulated D. pulchra metabolites at much higher levels than L. obtusa metabolites. A. dactylomela accumulated similar concentrations of L. obtusa metabolites to A. parvula. The loss of L. obtusa metabolites by A. dactylomela matched that expected for dilution of metabolites via growth of the sea hares. However, the loss of L. obtusa metabolites by A. parvula was faster than predicted for growth alone, suggesting that metabolites were actively metabolized or excreted. Data for the loss of D. pulchra metabolites by A. parvula was equivocal. The secretions of A. parvula fed D. pulchra or L. obtusa were analyzed for the presence of algal secondary metabolites to investigate one possible path of excretion. L. obtusa secondary metabolites were detected in the mucous and opaline secretions of A. parvula, but D. pulchra metabolites were not detected in any secretions. The deployment of L. obtusa secondary metabolites in secretions by A. parvula may explain the more rapid rate of loss of these compounds and is consistent with a possible defensive role for acquired metabolites.     

Identification of the Sex Pheromone of Sesamia cretica Lederer

By using solid phase micro-extraction and gas chromatography–mass spectrometry analyses, a sex pheromone blend for the stem borer, Sesamia cretica Lederer (Lepidoptera, Noctuidae), was identified as consisting of (Z)-9-tetradecen-1-ol (80%), (Z)-9-tetradecen-1-yl acetate (10%), and (Z)-11-hexadecen-1-ol (10%). The first two components had previously been discovered as attractants for S. cretica in field tests, but had not been identified in the female’s sex pheromone gland. A field-trapping trial showed that the three-component blend gave the highest catches of male S. cretica. This blend, in a sticky trap, was used to monitor a population of S. cretica in Iran, allowing the seasonal flight activity of this insect to be compared with that of a sympatric population of S. nonagrioides. The role of pheromones in the reproductive isolation of these species is discussed.     

Free volume theory of diffusion: Method of predicting activation energies of diffusion for gases in elastomers

It is well established that diffusion and relaxation processes in polymers above T_g are closely related in that they are both governed by the polymer segmental motions, which are believed to be determined by the free volume present in the system. The diffusion coefficients of gases in elastomers can be accounted for by the WLF equation using the “universal values” of constants A and B. The parameter K = B_D/B_η of Frisch and Rogers is used as a correction factor. An analysis has been made of the diffusion of five gases in nine elastomers, from data found in the literature. K and log D_g are shown to vary with the penetrant but not with the polymer. Therefore, once the values of K and log D_g of gases are determined, their diffusion coefficients in any elastomers of known T_g at a variety of temperatures can be estimated. From the Arrhenius and the WLF relationships, an equation is derived to predict the activation energy of diffusion directly from the temperature of diffusion, the glass transition temperature of the amorphous polymer, the predetermined value of K, and the universal constants A and B. In the systems studied, the predictions agree on the average to within 11–17% of the values calculated from the experimental data.     

The Temperature Dependence of Fluorescence of Dibenzoanthrones

The fluorescence spectra of three isomeric dibenzoanthrones, 13H-dibenzo[a, de]anthracen-13-one (1), 13H-benzo[hi]chrysen-13-one (2), and 7H-dibenzo[a, kl]anthracen-7-one (3), in an ethanol-ethertoluene mixed solution were measured as a function of the sample temperature (T). The three molecules provided individual T-dependences of fluorescence spectra. The spectra of 1 changed usually; as T was decreased, they were intensified, showing a vibrational structure more clearly. 2 fluoresced very weakly and the spectra were almost insensitive to T; it also phosphoresced at low temperatures. The spectra of 3 exhibited only a broad band and, strangely enough, it was reduced with decreasing T. The peculiar T-dependence of the fluorescence spectra of 2 and 3 was explained in terms of the results obtained by molecular orbital calculations.     

Variation of Proanthocyanidins in Lotus Species

The proanthocyanidin (PA) chemistry of 12 Lotus species of previously unknown PA content was examined in comparison with agricultural cultivars of L. pedunculatus, L. corniculatus, and L. tenuis and a “creeping” selection of L. corniculatus. Herbage harvested in winter 2000 and again in spring had extractable PA concentrations, estimations of which varied between 0.2 and 10.9% of dry matter. The four novel Lotus spp. with the highest concentrations were selected for further evaluation together with the agricultural accessions. PA concentrations in herbage were estimated for individual plants harvested in spring 2001 and bulk samples harvested in summer 2002–2003. PA oligomer and polymer fractions were separated by Sephadex LH-20 chromatography from aqueous acetone PA extracts of herbage. The chemical characteristics of the fractions were examined by acid catalyzed degradation with benzyl mercaptan, ¹³C nuclear magnetic resonance spectroscopy, electrospray ionization (ESI), and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF-MS). A wide variation was found in the chemical composition, mean degree of polymerization (mDP), and polydispersity of PAs from Lotus spp. Fractions from L. americanus, L. corniculatus “creeping selection,” and L. pedunculatus consisted predominantly of prodelphinidin (PD) units, whereas PA from L. angustissimus and L. corniculatus consisted predominantly of procyanidin (PC) units. An approximately equal composition in terms of PC and PD units was found in L. parviflorus and L. suaveolens. In L. angustissimus, epicatechin is dominant in both extender and terminal units. In all Lotus PA fractions, the 2,3-cis isomers (epicatechin or epigallocatechin) predominated. Only trace amounts of PA were extracted from L. tenuis. The mDP of the PA fractions ranged from 8 to 97, with high mDP found only for L. pedunculatus and L. americanus. In the ESI-MS and MALDI-TOF-MS of the L. angustissimus PA fraction, ions for homo-PC oligomers were dominant, whereas ions for hetero-oligomers predominated in the other Lotus spp. Ions indicative of A-type linkages were observed in the MS of L. americanus. The results are discussed in terms of possible relationships between the concentration and composition of the PAs of Lotus spp. and ecological factors.     

Assessment of acid hydrolysates of peat as substrate for Scytalidium acidophilum ATCC 26774 fungus

The acid-resistant fungus Scytalidium acidophilum ATCC 26774 was cultivated in submerged fermentation in hydrolysates of Sphagnum peat moss produced with H₂SO₄, HCl, HNO₃ and H₃PO₄ acids. Hydrolysis with H₂SO₄ produced the highest concentration of total carbohydrates and reducing sugars in the hydrolysates. However, when Scytalidium acidophilum ATCC 26774 was grown in undiluted hydrolysates, the H3PO₄ medium produced the best mycelial growth. The H₂SO₄ medium produced the highest dry biomass concentration (3.5 g dm^?3) obtained with water-diluted, non-supplemented peat hydrolysates. Supplementation of diluted H₂SO₄ hydrolysates with 3 g dm^?3 yeast extract and 0.4 g dm^?3 MgSO₄ considerably enhanced the growth, up to 5.9 g dm^?3 dry fungal biomass. The biomass composition of Scytalidium acidophilum ATCC 26774 grown in the medium which produced the best growth was determined, revealing a relatively high protein content of 37.5% of the dry mycelial weight.     

Stereospecific synthesis of ditactic polymers

Summary Polymerizations of t-butyl crotonate (E-TBC) and t-butyl isocrotonate (Z-TBC) were carried out in toluene at-78°C using t-BuMgBr as initiator. E-TBC gave polymers, whereas Z-TBC did not. The dimer of E-TBC isolated from the polymerization mixture by means of GPC contained predominatly one of the four possible diastereomers. X-ray crystallographic determination showed that the predominant dimer was the erythro-diisotactic isomer. t-BuLi/Et₃Al polymerized effectively both E-TBC and Z-TBC in toluene. The poly(E-TBC)s prepared with t-BuMgBr and t-BuLi/Et₃Al were insoluble in toluene, THF, and chloroform, but soluble in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP). Stereostructure of the poly(TBC)s was analyzed by the one- and two-dimensional NMR spectra measured in HFIP. The poly(E-TBC) prepared with t-BuMgBr was a 1:1 mixture of the erythro- and threo-diisotactic polymers with high stereoregularity. The poly(E-TBC) and poly(Z-TBC) obtained from the polymerizations with t-BuLi/Et₃Al were rich in disyndiotactic structure. Polymerization of TBCs with t-BuLi in toluene and THF was also studied.

---

     

Identification of New N‐Acylhomoserine Lactone Signalling Compounds of Dinoroseobacter shibae DFL‐12T by Overexpression of luxI Genes

Bacteria of the Roseobacter clade are widespread in the ocean and occur in many different habitats. In the genome of Dinoroseobacter shibae DFL‐12, luxI homologous genes that encode synthases responsible for the formation of N‐acylhomoserine lactones (AHLs) have been described. These compounds are known autoinducers that regulate several biological traits—namely, flagella formation and cell differentiation—in D. shibae through quorum sensing. The AHLs produced by D. shibae mainly consisted of N‐octadecadienoylhomoserine lactone (C18:2‐AHL) and N‐octadecenoylhomoserine lactone (C18:1‐HSL). In the wild type these AHLs are synthesized only in low abundance. The luxI genes were therefore expressed in Escherichia coli; this resulted in the formation of AHLs mostly different from those found in the D. shibae wild type. A luxI₁‐deficient mutant of D. shibae was then reprovided with an overexpressed luxI₁ gene. This strain produced large amounts of C18:2‐AHL and C18:1‐AHL, allowing full characterization of these compounds by mass spectrometric techniques and derivatization. Synthesis of the proposed structures confirmed that the major compound is (2E,11Z)‐N‐octadeca‐2,11‐dienoylhomoserine lactone ( 6 , C18:2‐HSL), accompanied by (Z)‐N‐octadec‐11‐enoylhomoserine lactone ( 5 , C18:1‐HSL). AHL 6 has not been reported before from other organisms and contains an unusual 2E double bond.     

Rapid Determination of the Amino Acid Configuration of Xenotetrapeptide

An E. coli strain with deletions in five transaminases (ΔaspC ΔilvE ΔtyrB ΔavtA ΔybfQ) was constructed to be unable to degrade several amino acids. This strain was used as an expression host for the analysis of the amino acid configuration of nonribosomally synthesized peptides, including the novel peptide “xenotetrapeptide” from Xenorhabdus nematophila, by using a combination of labeling experiments and mass spectrometry. Additionally, the number of D ‐amino acids in the produced peptide was assigned following simple cultivation of the expression strain in D₂O.     

Sex Pheromone of Nuttall's Sheep Moth, Hemileuca nuttalli, from the Eastern Sierra Nevada Mountains of California

The sex attractant pheromone blend of Hemileuca nuttalli (Lepidoptera: Saturniidae) from the eastern slope of the Sierra Nevada Mountains in California was determined to be a combination of E10,Z12-hexadeca-10,12-dien-1-yl acetate (E10,Z12–16:Ac) and E10,E12-hexadeca-10,12-dien-1-yl acetate (E10,E12–16:Ac). Ratios of the compounds in extracts of female pheromone glands varied around a mean of 100:48, although the ratio was not critical in field trials. Blends of synthetic E10,Z12–16:Ac and E10,E12–16:Ac in 100:50, 50:100, and 100:100 ratios attracted equal numbers of male moths. Field trials also indicated that E10,Z12–hexadeca-10,12-dien-1-ol (E10,Z12–16:OH) and E10,Z12-hexadeca-10,12-dienal (E10,Z12–16:Ald) were antagonistic at rates of 3.3% and 10%, respectively, of the E10,Z12–16:Ac, despite being found in female moth extracts. E10,E12–16:Ac, E10,Z12–16:OH, and E10,Z12–16:Ald all appear to have roles in maintenance of reproductive isolation between H. nuttalli and H. eglanterina.     

Identification of Sex Pheromones of Anadevidia peponis and Macdunnoughia confusa and Field Tests of Their Role in Reproductive Isolation of Closely Related Plusiinae Moths

Anadevidia peponis and Macdunnoughia confusa are defoliators of plants in the family Cucurbitaceae and Compositae, respectively, in Japan. GC-MS analyses of crude pheromone gland extracts treated with or without dimethyl disulfide indicated that females of A. peponis produced six monoene acetates and two monoene alcohols and that M. confusa females produced five monoene acetates. These components include (Z)-7-dodecenyl acetate as a major common constituent and three other acetates as minor common constituents. The minor constituents are quite different in blend composition. In addition, with (Z)-7-dodecenyl acetate, an indispensable component for male attraction is (Z)-5-decenyl acetate for A. peponis and (Z)-9-tetradecenyl acetate is essential for M. confusa. Field tests with synthetic lures showed synergistic effects of some other minor components and male attraction of three additional Plusiinae species, Macdunnoughia purissima, Ctenoplusia albostriata, and Chrysodeixis eriosoma, suggesting their reproductive isolation is based in part on pheromonal communication.     

Influence of moderate amounts of trans fatty acids on the formation of polyunsaturated fatty acids

The effect of trans fatty acids from partially hydrogenated soybean oil and butterfat on the formation of polyunsaturated fatty acids was investigated. Five groups of rats were fed diets that contained 20 wt% fat. The content of linoleic acid was adjusted to 10 wt% of the dietary fats in all diets, whereas the amount of trans fatty acids from partially hydrogenated soybean oil (PHSBO) was varied from 4.5 to 15 wt% in three of the five diets. The fourth group received trans fatty acids from butterfat (BF), while the control group was fed palm oil without trans fatty acids. Trans fatty acids in the diet were portionally reflected in rat liver and heart phosphatidylethanolamine (PE), phosphatidylcholine (PC), phosphatidylinositol, and phosphatidylserine. Incorporation in the sn-1 position was compensated by a decrease in saturated fatty acids. Trans fatty acids were not detected in diphosphatidylglycerol. Compared to the presence in the dietary fats, 8t- and 10t-18:1 were discriminated against in the incorporation in PE and PC from liver and heart, whereas 9t- and 12t-18:1 were preferred. The formation of 20:4n-6 was not influenced by 4.5 wt% trans fatty acids (from PHSBO) but apparently was by 10 wt% in liver. In contrast, even a content of 2.5 wt% trans fatty acids from BF reduced the formation of 20:4n-6. The inhibitory effect of trans isomers on linoleic acid conversion was reflected less in heart than in liver and less for PE than for PC. Groups with trans fatty acids showed increased 22:6n-3 and 22:5n-3 deposition in liver and heart PE and PC.     

Modelling the Kinetics of Photoinitiated Polymerization of Di(meth)acrylates

The kinetics of photoinitiated polymerization of six analogous di(meth)acrylates and diacrylates was analysed according to the autocatalytic model R_p=kp^m(1-p)ⁿ (where R_p is polymerization rate, p is conversion degree, k is reaction rate constant and m and n are exponents), in order to find the influence of the reaction temperature and atmosphere, as well as monomer structure, on the parameters k, m and n. The best fit between the model prediction and experimental data was for the polymerization of diacrylates in an inert gas atmosphere. The autocatalytic exponent, m, for polymerization in argon of both di-methacrylates and diacrylates was found to be close to unity, whereas the reaction order exponent, n, was twice as high for the former compared with the latter (in the range of c. 3–5 and c. 1·3–2, respectively). An increase in the polymerization temperature caused a drop in both exponents. This drop is much more rapid in the case of the exponent n. Changes in the m and n exponents with temperature, as well as the difference in n exponents for the polymerization of acrylates and methacrylates, may be related to changes and differences in the mobility of reactive species during the reaction. The influence of atmospheric oxygen on the polymerization parameters is manifested by a very high increase in value of the exponent n. In the photochemically initiated process, an increase in the polymerization rate with temperature results mainly from a rapid decrease in the exponent n and, to a much lesser degree, from an increase in the reaction rate constant k. © of SCI.     

Determination of Essentially Disconnected Sites in the Boundary of Coronoid Subgraphs

A coronoid subgraph H = {P,e_i,i=0,1,…,g-1} is given: P is a six-sided polyhex (benzenoid hydrocarbon) with holes, and e_i is an external edge of P; in the outer and inner boundaries of P one side is parallel to the opposite side. H is then cut into slices (subgraphs of H). A set of rules (Lemmas) for such slices is presented; each rule gives an order to the numbers of single and/or double bonds in a slice of H. The Lemmas thus determine whether or not each site has an essential single bond in the outer boundary of P.