The germicidal activity of rosin soap and fatty acid-rosin soap as indicated by hand-washing experiments

Summary and Conclusions Price’s procedure as slightly modified (4) was used for studying the germicidal action of cleaning agents on the hands and showed that rosin soap and a commercial soap containing rosin were more active germicidally on the bacteria normally found on human skin than the usual commercial fatty acid soaps free from rosin soap. The experiments indicate that the lather of a 10-percent coconut oil soap solution and of a 10-percent coconut oil-rosin soap solution are germicidally active against the organisms removed. However, three 2-minute washes with these soap solutions had little effect on the bacteria not removed from the hands. The use of a 10-percent rosin soap solution in the same manner had a marked germicidal effect against both the organisms removed and those remaining. The lather of a commercial soap containing rosin soap was shown to be germicidally active, but three 2-minute washes had only a slight effect on the resident flora. However, the regular use of this soap daily for one week led to substantial reduction of both the transient and resident flora of the hands. The evidence of germicidal activity of rosin soaps and soaps containing rosin, both with regard to these hand-washing experiments and the “in vitro” (7) experiments, indicates that wider consideration might well be given this type of soap where germicidal activity is of importance. L. S. Stuart was employed in the Industrial-Farm Products Research Division when this work was done.     

Synthesis of a phosphatidyl derivative of vitamin E and its antioxidant activity in phospholipid bilayers

A novel phospholipid containing a chromanol structure at its polar head group was synthesized from egg yolk phosphatidylcholine and 2,5,7,8-tetramethyl-6-hydroxy-2-(hydroxyethyl)chroman by transphosphatidylation catalyzed by phospholipase D fromStreptomyces lydicus. The structure of the product synthesized was shown by spectral analysis to be 1,2-diacyl-sn-glycero-3-phospho-2′-hydroxyethyl-2′ 5′,7′,8′-tetramethyl-6′-hydroxychroman. The phosphatidylchromanol (PCh) showed antioxidant activity against radical chain oxidation of methyl linoleate in solution in a manner similar to that ofd-α-tocopherol (α-Toc) and 2,2,5,7,8-pentamethyl-6-chromanol. However, PCh was less effective as a chain-breaking antioxidant than was α-Toc when unilamellar egg yolk phosphatidylcholine liposomes were exposed to either a water-soluble or a lipid-soluble radical initiator. It is likely that the phospholipid nature of PCh affects the location and the mobility of the chromanol moiety in the membrane bilayer resulting in a decrease in antioxidant activity. On the other hand, the antioxidant activity of PCh was little different from that of α-Toc in unilamellar liposomes when exposed to a lipid-soluble radical initiator in the presence of ascorbic acid. It appears that PCh in phospholipid bilayers can be regenerated by ascorbic acid in aqueous phase as can be α-Toc. The new phospholipid, phosphatidylchromanol, should prove useful as a chain-breaking antioxidant in phospholipid membranes.     

Antibacterial and xanthine oxidase inhibitory cerebrosides from <Emphasis Type="Italic">Fusarium</Emphasis> sp. IFB-121, and endophytic fungus in <Emphasis Type="Italic">Quercus variabilis</Emphasis>

Two antibacterial and xanthine oxidase inhibitory cerebrosides, one of which is chemically new, were characterized from the chloroform-methanol (1∶1) extract of Fusarium sp. IFB-121, an endophytic fungus in Quercus variabilis. By means of chemical and spectral methods [IR, electrospray ionization MS (ESI-MS), tandem ESI-MS, ¹H and ¹³C NMR, distortionless enhancement by polarization transfer, COSY, heteronuclear multiple-quantum coherence, heteronuclear multiple-bond correlation, and 2-D nuclear Overhauser effect correlation spectroscopy], the structure of the new metabolite named fusaruside was established as (2S,2′R,3R,3′E,4E,8E,10E)-1-O-β-d-glucopyranosyl-2-N-(2′-hydroxy-3′-octadecenoyl)-3-hydroxy-9-methyl-4,8,10-sphingatrienine, and the structure of the other was identified as (2S,2′R,3R,3′E,4E,8E)-1-O-β-d-glucopyranosyl-2-N-(2′-hydroxy-3′-octadecenoyl)-3-hydroxy-9-methyl-4,8-sphingadienine. Both new and known cerebrosides, although inactive to Trichophyton rubrum and Candida albicans, showed strong antibacterial activities against Bacillus subtilis, Escherichia coli, and Pseudomonas fluorescens, with their minimum inhibitory concentrations being 3.9, 3.9, and 1.9 μg/mL, and 7.8, 3.9, and 7.8 μg/mL, respectively. Furthermore, both metabolites were inhibitory to xanthine oxidase, with the IC₅₀ value of fusaruside being 43.8±3.6 μM and the known cerebroside being 55.5±1.8 μM.     

Synthesis and antimicrobial activity of fatty 2-morpholinones prepared from epoxy fatty acid methyl esters

Reactions of methyl 10,11-epoxyundecanoate (I), methyl 9,10-epoxyoctadecanoate (II) methyl 12,13-epoxy-cis-9-octadecenoate (III) and methyltrans-2,3-epoxyhexadecenoate (IV) with glycine in dimethylformamide (DMF) in the presence of anhydrous AlCl₃ as catalyst have yielded 5(6)-[8′-carbomethoxyoctyl]-2-morpholinone (V); 5(6)-[7′'-carbomethoxyheptyl]-6(5)-octyl-2-morpholinone (VI);5(6)-[10′-carbomethoxydec-cis-2-enyl)-6(5)-pentyl-2-morpholinone (VII), and 5-tridecyl-6-carbomethoxy 2-morpholinone (VIII), respectively in excellent yield. The products have been characterized with the help of spectral data and microanalysis. Antifungal and antibacterial screening of (V–VIII) showed pronounced activity against four bacteria and seven fungal species. Presented in part at the 43rd Annual Convention of the Oil Technologists' Association of India (OTAI) held in Bombay, India In February 1988.     

熊果酸香皂的制备及其生物活性研究

以棕榈油皂粒为皂基制备熊果酸香皂,按照国家标准方法对香皂中游离苛性碱、水分和挥发物含量进行检测,采用平板计数法和动物实验对该香皂的体外抑菌作用和安全性进行研究。结果表明,熊果酸香皂对白色假丝酵母、肺炎克雷伯氏菌、伤寒沙门氏菌、铜绿假单胞菌、MRSA1和MRSA2均具有明显抑菌作用,在熊果酸质量分数为7.5%时抑菌效果最为显著,动物实验表明香皂对小鼠皮肤和眼睛黏膜无不良反应和毒副作用,长期使用不会对皮肤产生刺激性。     

Antioxidant properties of phenolic compounds in macadamia nuts

Phenolic compounds in macadamia nuts and shells were identified, and their antioxidant activities were evaluated in refined macadamia nut oil. Thin-layer chromatography of oil extracted from macadamia nut kernels and shells indicated the possible presence of catechol, phrogallol, and 3,4,5-trihydroxy phenolic compounds. Four phenolic compounds were tentatively identified as 2,6-dihydroxybenzoic acid, 2′-hydroxy-4′-methoxyacetophenone, 3′,5′-dimethoxy-4′-hydroxyacetophenone, and 3,5-dimethoxy-4-hydroxycinnamic acid. Adding 0.01% of 2′-hydroxy-4′-methoxyacetophenone, 3′,5′-dimethoxy-4′-hydroxyacetophenone, or 3,5-dimethoxy-4-hydroxycinnamic acid to the oil significantly increased the Rancimat induction time against the control (P<0.0001). At this concentration, 3′,5′-dimethoxy-4′-hydroxyacetophenone was the most effective compound added. Although induction times of oils with 0.01%, 2,6-dihydroxybenzoic acid were not significantly different from the control, at 0.1% there was a significant difference from the control (P<0.0001). The activity was the same as that of 2′-hydroxy-4′-methoxyacetophenone at 0.1%.     

Synthesis and antibacterial activities of some 2-amino-4-(1,1′-biphenyl-4-yl)-6-aryl-6H-1,3-thiazines

A series of new 2-amino-4-(1,1′-biphenyl-4-yl)-6-aryl-6H-1,3-thiazines has been synthesized, characterized by IR, ¹H NMR, ¹³C NMR, mass and elemental analyses and evaluated for in vitro antibacterial activity against some Gram-positive and Gram-negative bacteria. The antibacterial data revealed that the compounds had better activity against tested organisms than the reference norfloxacin.     

A New Cationic Gemini Surfmer: Synthesis and Surface Activities

A new cationic gemini surfmer (polymerizable surfactant or surface-active monomer) with an acrylic reactive group in its spacer group was synthesized and characterized, and its surface activity properties were examined in comparison with its intermediate surfactant 12-3OH-12·2Cl⁻, a previously-reported gemini surfmer 12′-2-12′·2Br⁻, as well as monomeric surfactant dodecyl trimethylammonium bromide. It was found that neither the incorporation of a double bond onto the gemini surfactant nor the change of location of the double bond will affect surface activities of the gemini surfactant.     

Studies in the development of antibacterial surfactants. II. performance of germicidal and deodorant soaps

Summary It has been shown that mixtures of hexachlorophene and trichlorocarbanilide or bithionol and trichlorocarbanilide in soap show a marked synergism with respect to antibacterial properties. In both cases the approximate ratio of 50/50 of the two components represents an optimum. Nonionic detergents enhance the antibacterial activity of trichlorocarbanilidein vitro when present at relatively low levels. At higher levels of nonionic the antibacterial agent is neutralized and loses its effectiveness. The antibacterial activity of the pair hexachlorophene-trichlorocarbanilide extends over a wide spectrum of micro-organisms, and synergism is shown with each test organism. High antibacterial activity of the synergistic pairs in soap is shown both inin vivo handwashing studies and in subjective deodorant tests. On the other hand, it is shown by way of several examples thatin vivo observations do not necessarily correlate within vitro bacteriological screening tests.     

The new toilet soaps

Toilet soap bars have undergone few major technical changes in the last century. Noteworthy improvements were floating soap, the development of effective deodorant and antibacterial soaps, the so-called “hard water” bars, and advances in packaging technology. The trends in these areas toward product and process improvement will accelerate in the 1970’s. New raw materials are becoming available which will give greater formulation flexibility, with emphasis towards greater mildness and effectiveness. Among these products are the synthetic fatty acids which could partially replace coconut acids, more effective broad spectrum antibacterial agents for better control of skin microorganisms, and mild detergent additives with good physical properties and less defatting tendency. In processing, the move is toward continuous soap-making equipment in place of the old kettle processes which are still widely used. More powerful and specialized plodders are available; these will facilitate the development of new product types. Presented at the AOCS-AACC 1968 Joint Meeting, Washington, D.C., April 1968.     

Protective effect of a vitamin E analog, phosphatidylchromanol, against oxidative hemolysis of human erythrocytes

The protective effect of a vitamin E analog, phosphatidylchromanol [1,2-diacyl-sn-glycero-3-phospho-2′-(hydroxyethyl)-2′, 5′,7′,8′-tetramethyl-6′-hydroxychroman; PCh], against oxidative hemolysis of human erythrocytes was examined and was compared with those of vitamin E (α-tocopherol) and 2,2,5,7,8-pentamethyl-6-chromanol (PMC). These three compounds at 50 μM protected the erythrocytes from hemolysis, when erythrocyte suspension (10%, vol/vol) was incubated with a water-soluble radical generator, 2,2′-azobis(2-amidino-propane)-dihydrochloride (75 mM). When erythrocyte suspension was oxidized after pretreatment with these compounds (50 μM) for 30 min followed by washing, PCh protected about 54% of erythrocytes from the hemolysis, while α-tocopherol protected only about 16% of the cells and PMC did not show any protective effect. During preincubation, α-tocopherol, PMC, and PCh were incorporated into the cells at the concentration of 12.6, 3.7, and 16.3 nmol/mg protein, respectively. Moreover, PCh was found in the ghost membrane fraction at a 20% higher level than α-tocopherol, and no PMC was detected in this fraction. These results indicate that phosphatidyl group in PCh accts as an excellent carrier of chromanol moiety into cells as well as an anchor within membranes more efficiently than phytyl group in α-tocopherol. PMC seems to be slightly anchored within membranes because of the lack of hydrophobic side chain. The excellent antihemolytic activity of PCh is likely to be caused by its accumulation within erythrocyte membranes.     

Inhibitors and accelerators in autoxidation of soaps

Summary 1) Nineteen organic and inorganic chemicals were tested for their action in peroxide accumulation in soaps. 2) The effect of small quantities of various metals in soap was tested, and a new “activity series” was proposed. 3) The relative effect of metals in accelerating peroxide formation is more marked in the dark than in light. 4) In the presence of metallic accelerators, organoleptic rancidity appears at a much lower peroxide value than in the case of soap uncontaminated by metals.     

Cytochrome c release is required for phosphatidylserine peroxidation during fas-triggered apoptosis in lung epithelial A549 cells

Oxidation of phosphatidylserine (PtdSer) has been shown to play a pivotal role in signaling during cell apoptosis and subsequent recognition of apoptotic cells by phagocytes. However, the redox catalytic mechanisms involved in selective PtdSer oxidation during apoptosis remain poorly understood. here we employed anti-Fas antibody CH-11-treated A549 cells as a physiologically relevant model to investigate the involvement of PtdSer oxidation and its potential mechanism during apoptosis. We demonstrated that ligation of CH-11 with its cognate receptor initiated execution of apoptotic program in interferon gamma-pretreated A549 cells as evidenced by activation of caspase and DNA fragmentation. A significant increase of cytochrome c (cyt c) content in the cytosol as early as 2 h after CH-11 exposure was detected indicating that Fas-induced apoptosis in A549 cells proceeds via extrinsic type II pathway and includes mitochondrial signaling. PtdSer was selectively oxidized 3 h after anti-Fas triggering while two more abundant phospholipids—phosphatidylcholine (PtdCho) and phosphatidylethanolamine (PtdEtn)—and the major intracellular antioxidant, glutathione, remained nonoxidized. A pan-caspase inhibitor, z-VAD, fully blocked cyt c release and oxidation of PtdSer in Fas-treated A549 cells. On the other hand, z-DQMD, a caspase-3 inhibitor, completely inhibited caspase-3 activity but did not fully block caspase-8 activation and release of cyt c. Importantly, z-DQMD failed to protect PtdSer from oxidation. In addition, in a model system, we demonstrated that peroxidase activity of cyt c was greatly enhanced in the presence of dioleoylphosphatidylserine containing liposomes by monitoring oxidation of 2′,7′-dichlorodihydrofluorescein to 2′,7′-dichlorofluorescein. We further showed that peroxidase activity of cyt c catalyzed oxidation of 1-palmitoyl-2-arachidonoyl-3-glycero-phosphoserine using a newly developed HPLC assay. MS analysis of 1-palmitoyl-2-arachidonoyl-3-glycero-phosphoserine revealed that in addition to its mono- and dihydroperoxides, several different PtdSer oxidation products can be formed. Overall, we concluded that cyt c acts as a catalyst of PtdSer oxidation during Fas-triggered A549 cell apoptosis.     

Novel vitamin E derivative with 4-substituted resorcinol moiety has both antioxidant and tyrosinase inhibitory properties

A novel vitamin E derivative, (6″-hydroxy-2″,5″,7″,8″-tetramethylchroman-2″-yl) methyl 3-(2′,4′-dihydroxyphenyl)propionate (TM4R), which has a chromanoxyl ring and 4-substituted resorcinol moieties, was synthesized; and its inhibitory effects on tyrosinase, antioxidant ability, and lightening effect of ultraviolet B (UVB)-induced hyperpigmentation were estimated. TM4R showed potent inhibitory activity on tyrosinase, which is the rate-limiting enzyme in melanogenesis. The scavenging activities of TM4R on 1,1-diphenyl-2-picrylhydrazyl and hydroxyl radicals were found to be nearly the same as those of α-tocopherol. Furthermore, an efficient lightening effect was observed following topical application of TM4R to UVB-stimulated hyperpigmented dorsal skin of brownish guinea pigs. These results suggest that TM4R may be a candidate for an efficient whitening agent, possibly by inhibiting tyrosinase activity and biological reactions caused by reactive oxygen species.     

Soap-based detergent formulations: XIX. Amphoteric alkylsuccinamide derivatives as lime soap dispersants

A series of amphoteric surfactants was synthesized by reaction of 1,3-propanesultone with N-alkyl-N′-(ω,ω-dimethylaminoalkyl)succinamides. The intermediate succinamides were prepared by reacting methyl N-alkylsuccinamates, obtained from alkylamines containing 8 to 18 carbon atoms, with N,N-dimethyl-1,3-propylenediamine or N,N-dimethylethylenediamine neat. The amphoterics were isolated as hygroscopic crystalline solids having superior lime soap dispersing ability, water solubility, and calcium ion stability. Detergency studies at 0.2% concentration (300 ppm water hardness) indicated good washing ability when used alone and excellent performance in combination with soap or in soap-silicate formulations. Presented at the AOCS Meeting, Cincinnati, 1975.     

Synthesis and characterization of poly(2-hydroxyethyl methacrylate/itaconic acid) copolymeric hydrogels

In the present study poly(2-hydroxyethyl methacrylate-co-itaconic acid) (P(HEMA/IA)) hydrogels were synthesized by free-radical copolymerization of 2-hydroxyethyl methacrylate and itaconic acid in order to evaluate as controlled release drug delivery system. All polymerizations were performed in a mixture of water/ethanol with ethylene glycol dimethacrylate, as crosslinking agent, potassium persulfate, as initiator, and N, N, N′, N′-tetramethylethylene diamine, as activator. The samples were characterized by FTIR and SEM. Swelling kinetics and antibiotic release studies were performed using gravimetry and UV spectrophotometry, respectively. The antibacterial activity studies were performed bearing in mind that infections are the most common cause of biomaterial implant failure and represent a constant menace to the application of medical implants. The hemocompatibility testing was performed as imperative for medical devices intended for direct or indirect blood exposure. In accordance with the results of antibacterial assessment on gels loaded with antibiotics and hemolytic activity testing these gels exerted good bacterial growth inhibition and favorable hemolytic activity. The release profiles of antibiotics, evaluated in vitro conditions, were correspondent for antibacterial therapeutics. Therefore, it was concluded that (P(HEMA/IA)) gels could be propound for the potential application as drug delivery systems for the controlled release of antibiotics.     

New Sphingolipids with a Previously Unreported 9-Methyl-C<Subscript>20</Subscript>-sphingosine Moiety from a Marine Algous Endophytic Fungus <Emphasis Type="Italic">Aspergillus niger</Emphasis> EN-13

Asperamides A (1) and B (2), a sphingolipid and their corresponding glycosphingolipid possessing a hitherto unreported 9-methyl-C₂₀-sphingosine moiety, were characterized from the culture extract of Aspergillus niger EN-13, an endophytic fungus isolated from marine brown alga Colpomenia sinuosa. The structures were elucidated by spectroscopic and chemical methods as (2S,2′R,3R,3′E,4E,8E)-N-(2′-hydroxy-3′-hexadecenoyl)-9-methyl-4,8-icosadien-1,3-diol (1) and 1-O-β-d-glucopyranosyl-(2S,2′R,3R,3′E,4E,8E)-N-(2′-hydroxy-3′-hexadecenoyl)-9-methyl-4,8-icosadien-1,3-diol (2). In the antifungal assay, asperamide A (1) displayed moderate activity against Candida albicans.     

Antimicrobial activity of aroma chemicals and essential oils

Determination of the minimum inhibitory concen-trations (MIC) of 212 common soap fragrance raw materials demonstrated that the paper disc-petri plate technique does not reflect the relative anti-microbial activity of these materials. Commonly used soap bacteriostats were shown to be 100 to 1000 times more effective than the most active fragrance materials. Of 521 fragrance materials initially screened by the petri plate method, 44% were inhibitory against one of the three test organisms, and 15% were effective against all three(Staphylococcus aureus, Escherichia coli, Candida albicans). Of a selected number (212) of these positive materials, subsequently screened against a lipophilic diphtheroid organism(Corynebacterium sp.), 64 materials (30%) were positive against all four test organisms. However, only nine materials (4%) had a MIC as low as 50 ppm compared to the common soap bacteriostat TCC, which had a MIC of 0.08 ppm (vs.S. aureus). In hand-degerming tests, no reduction of bacterial counts was obtained with a soap containing the most active fragrance materials. These results demonstrate that creation of a practical antimicrobial soap fragrance does not appear to be possible. 1Preliminary report presented at the 1976 national meeting of the American Chemical Society, Miami Beach, FL, September 1978.     

Radical Scavenging Activity and Performance of Novel Phenolic Antioxidants in Oils During Storage and Frying

Novel phenolic antioxidants: 2a (6′-hydroxy-2′,5′,7′,8′-tetramethylchroman-2′-yl)methyl 3-methoxy-4-hydroxycinnamate, 2b (6′-hydroxy-2′,5′,7′,8′-tetramethylchroman-2′-yl)methyl 3,5-dimethoxy-4-hydroxycinnamate, 2c (6′-hydroxy-2′,5′,7′,8′-tetramethylchroman-2′-yl)methyl 3,4-dihydroxycinnamate, and 3 (6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)methyl (6′-hydroxy-2′,5′,7′,8′-tetramethylchroman-2′-carboxylate) have been prepared in good yields and fully characterized by ¹H and ¹³C NMR, and HRMS. Their radical scavenging activities have been evaluated by DPPH and ORAC assays. Each of the synthesized antioxidants exhibited significantly higher radical scavenging activities than trolox and α-tocopherol. These novel antioxidants efficiently protected canola oil triacylglycerides (CTG) during accelerated storage and frying. Compounds 2c and 3 were significantly more efficient than α-tocopherol protecting CTG under accelerated storage. All new antioxidants were more efficient than α-tocopherol under frying conditions and present significantly higher thermal stability.     

Syntheses and biological activities of 5′-O-methacryloyl-3′-azido-3′-deoxythymidine and its polymers

The new monomer, 5′-O-methacryloyl-3′-azido-3′-deoxythymidine (MAZT), was synthesized from methacryloyl chloride (MAC) and 3′-azido-3′-deoxythymidine (AZT). The homopolymer of MAZT and copolymers of MAZT with acrylic acid (AA) or exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic glycinylimide (ETGI) were synthesized by radical polymerizations. The structures of MAZT and polymers were confirmed identified by FT-IR and ¹H-NMR spectroscopies. The number average molecular weights (Mˉn) and polydispersity indices of the synthesized polymers were in the range of 4,400 ∼ 20,400 and 1.2 ∼ 2.0. The in vitro cytotoxicities of polymers against K562 human leukemia and normal cell lines were greater than that of control. Received: 19 August 1997/Accepted: 26 September 1997