Potential Fatty Acid as Antibacterial Agent Against Oral Bacteria of Streptococcus mutans and Streptococcus sanguinis from Basil (Ocimum americanum): In vitro and In silico Studies.

BACKGROUND: Streptococcus mutans and Streptococcus sanguinis are Gram-positive bacteria that cause dental caries. MurA enzyme acts as a catalyst in the formation of peptidoglycan in bacterial cell walls, making it ideal as an antibacterial target. Basil (Ocimum americanum) is an edible plant that is diverse and has been used as a herbal medicine for a long time. It has been reported that basil has a pharmacological effect as well as antibacterial activity. The purpose of this study was to identify antibacterial compounds in O. americanum and analyze their inhibition activity on MurA enzyme. METHODS: Fresh leaves from O. americanum were extracted with n-hexane and purified by a combination of column chromatography on normal and reverse phases together with in vitro bioactivity assay against S. mutans ATCC 25175 and S. sanguinis ATCC 10556, respectively, while in silico molecular docking simulation of lauric acid (1) was conducted using PyRx 0.8. RESULTS: The structure determination of antibacterial compound by spectroscopic methods resulted in an active compound lauric acid (1). The in vitro evaluation of antibacterial activity in compound 1 showed Minimum Inhibitory Concentration (MIC) and Minimum Bactericidal Concentration (MBC) values of 78.13 and 156.3 ppm and 1250 and 2500 ppm against S. sanguinis and S. mutans, respectively. Further analysis and in silico evaluation determined lauric acid (1) as MurA Enzyme inhibitor. Lauric acid (1) showed a binding affinity of -5.2 Kcal/mol, which was higher than fosfomycin. CONCLUSION: Lauric acid showed the potential as a new natural antibacterial agent through MurA inhibition in bacterial cell wall biosynthesis.

Peak AAA fatty acid homolog contaminants present in the dietary supplement l-Tryptophan associated with the onset of eosinophilia-myalgia syndrome.

The eosinophilia-myalgia syndrome (EMS) outbreak that occurred in the USA and elsewhere in 1989 was caused by the ingestion of Showa Denko K.K. (SD) L-tryptophan (L-Trp). "Six compounds" detected in the L-Trp were reported as case-associated contaminants. Recently the final and most statistically significant contaminant, "Peak AAA" was structurally characterized. The "compound" was actually shown to be two structural isomers resulting from condensation reactions of L-Trp with fatty acids derived from the bacterial cell membrane. They were identified as the indole C-2 anteiso (AAA1-343) and linear (AAA2-343) aliphatic chain isomers. Based on those findings, we utilized a combination of on-line HPLC-electrospray ionization mass spectrometry (LC-MS), as well as both precursor and product ion tandem mass spectrometry (MS/MS) to facilitate identification of a homologous family of condensation products related to AAA1-343 and AAA2-343. We structurally characterized eight new AAA1-XXX/AAA2-XXX contaminants, where XXX represents the integer molecular ions of all the related homologs, differing by aliphatic chain length and isomer configuration. The contaminants were derived from the following fatty acids of the bacterial cell membrane, 5-methylheptanoic acid (anteiso-C8:0) for AAA1-315; n-octanoic acid (n-C8:0) for AAA2-315; 6-methyloctanoic acid (anteiso-C9:0) for AAA1-329; n-nonanoic acid (n-C9:0) for AAA2-329; 10-methyldodecanoic acid (anteiso-C13:0) for AAA1-385; n-tridecanoic acid (n-C13:0) for AAA2-385; 11-methyltridecanoic acid (anteiso-C14:0) for AAA1-399; and n-tetradecanoic acid (n-C14:0) for AAA2-399. The concentration levels for these contaminants were estimated to be 0.1-7.9 µg / 500 mg of an individual SD L-Trp tablet or capsule The structural similarity of these homologs to case-related contaminants of Spanish Toxic Oil Syndrome (TOS) is discussed.

Lauric acid and myristic acid from Allium sativum inhibit the growth of Mycobacterium tuberculosis H37Ra: in silico analysis reveals possible binding to protein kinase B.

CONTEXT: The bulb of Allium sativum Linn (Alliaceae) has numerous medicinal values. Though the petroleum ether extract of the bulb has shown to exhibit antimycobacterial activity, the phytochemical(s) responsible for this inhibitory activity is not known. OBJECTIVE: To characterize the bioactive compounds in the petroleum ether extract of Allium sativum (garlic) that inhibit the growth of Mycobacterium tuberculosis H37Ra. MATERIALS AND METHODS: Bioactivity-guided fractionation was employed to isolate the bioactive compounds. Antimycobacterial activity was evaluated by well-diffusion method and microplate alamar blue assay (MABA). Infrared spectroscopy, mass spectrometry and nuclear magnetic resonance spectroscopy were used to characterize the bioactive compounds. Autodock was used to obtain information on molecular recognition, and molecular dynamics simulation was performed using GROMACS. RESULTS: The bioactive compounds that inhibited the growth of M. tuberculosis H37Ra were found to be lauric acid (LA) and myristic acid (MA). The minimal inhibitory concentration of LA and MA was found to be 22.2 and 66.7 µg/mL, respectively. In silico analysis revealed that these fatty acids could bind at the cleft between the N-terminal and C-terminal lobes of the cytosolic domain of serine/threonine protein kinase B (PknB). DISCUSSION AND CONCLUSION: The inhibition activity was dependent on the alkyl chain length of the fatty acid, and the amino acid residues involved in binding to fatty acid was found to be conserved across the Pkn family of proteins. The study indicates the possibility of using fatty acid derivatives, involving Pkn family of proteins, to inhibit the signal transduction processes in M. tuberculosis.

Tangential Flow Ultrafiltration Allows Purification and Concentration of Lauric Acid-/Albumin-Coated Particles for Improved Magnetic Treatment.

Superparamagnetic iron oxide nanoparticles (SPIONs) are frequently used for drug targeting, hyperthermia and other biomedical purposes. Recently, we have reported the synthesis of lauric acid-/albumin-coated iron oxide nanoparticles SEON(LA-BSA), which were synthesized using excess albumin. For optimization of magnetic treatment applications, SPION suspensions need to be purified of excess surfactant and concentrated. Conventional methods for the purification and concentration of such ferrofluids often involve high shear stress and low purification rates for macromolecules, like albumin. In this work, removal of albumin by low shear stress tangential ultrafiltration and its influence on SEON(LA-BSA) particles was studied. Hydrodynamic size, surface properties and, consequently, colloidal stability of the nanoparticles remained unchanged by filtration or concentration up to four-fold (v/v). Thereby, the saturation magnetization of the suspension can be increased from 446.5 A/m up to 1667.9 A/m. In vitro analysis revealed that cellular uptake of SEON(LA-BSA) changed only marginally. The specific absorption rate (SAR) was not greatly affected by concentration. In contrast, the maximum temperature Tmax in magnetic hyperthermia is greatly enhanced from 44.4 °C up to 64.9 °C by the concentration of the particles up to 16.9 mg/mL total iron. Taken together, tangential ultrafiltration is feasible for purifying and concentrating complex hybrid coated SPION suspensions without negatively influencing specific particle characteristics. This enhances their potential for magnetic treatment.

Chemical characterization and antioxidant activity of Amazonian (Ecuador) Caryodendron orinocense Karst. and Bactris gasipaes Kunth seed oils.

Nowadays, data concerning the composition of Caryodendron orinocense Karst. (Euphorbiaceae) and Bactris gasipaes Kunth (Arecaceae) seed oils are lacking. In light of this fact, in this paper fatty acids and unsaponifiable fraction composition have been determined using GC-MS, HPLC-DAD (Diode Array Detector), NMR approaches and possible future applications have been preliminary investigated through estimation of antioxidant activity, performed with DPPH test. For C. orinocense linoleic acid (85.59%) was the main component, lauric (33.29%) and myristic (27.76%) acids were instead the most abundant in B. gasipaes. C. orinocense unsaponifiable fraction (8.06%) evidenced a remarkable content of ß-sitosterol, campesterol, stigmasterol, squalene and vitamin E (816 ppm). B. gasipaes revealed instead ß-sitosterol and squalene as main constituents of unsaponifiable matter (3.01%). Antioxidant capacity evidenced the best performance of C. orinocense seed oil. These preliminary results could be interesting to suggest the improvement of the population's incomes from Amazonian basin. In particular the knowledge of chemical composition of C. orinocense and B. gasipaes oils could be helpful to divulge and valorize these autochthones plants.

Effect of oleic, lauric and myristic acids on phenylephrine-induced contractions of isolated rat vas deferens.

D-004, a lipid extract of Roystonea regia fruits that contains oleic, lauric and myristic acids as major components inhibits alpha1-adrenoreceptors-mediated contractile responses in isolated rat vas deferens and prostate trips; no study has demonstrated a similar effect for oleic, lauric or myristic acids individually. Therefore, the effects of D-004 (250 microg/mL), oleic (100 microg/mL), lauric (50 microg/mL) or myristic (25 microg/mL) acids and their combined effects on phenylephrine (PHE: 10(-7)-10(-4) mol/L) induced contractions has been studied. No treatment changed the basal tone of the preparations, but all inhibited PHE-induced contractions. D-004 produced the highest inhibition, followed by lauric acid, which was more effective than myristic and oleic acids against PHE-induced contractions of control group. D-004 and the mixture of the three acids produced similar inhibitions.

A novel cyclopropyl-containing fatty acid glucoside from the seeds of Litchi chinensis.

3,12-Dihydroxy-cis-3,4-methylenedodecanoic acid 3-O-ß-d-glucopyranoside, trivially named litchioside C (1), the first cyclopropyl-containing fatty acid glycoside, was isolated along with three previously uncharacterized galactosylacylglycerols from the seeds of Litchi chinensis. Its structure was established on the basis of spectroscopic analysis including HRESIMS and 2D NMR spectra. Its antioxidant and antibacterial activities were evaluated and its biogenetic pathway was discussed.

[Two new phenolic acids from Drynariae rhizoma].

To study the chemical constituents of Drynariae Rhizoma, nine phenolic acids were isolated from a 70% ethanol extract by using a combination of various chromatographic techniques including column chromatography over silica gel, ODS, Sephadex LH-20, and semi-preparative HPLC. By spectroscopic techniques including 1H NMR, 13C NMR, 2D NMR, and HR-ESI-MS, these compounds were identified as 4, 4'-dihydroxy-3, 3'-imino-di-benzoic acid (1), protocatechuic acid (2), gallic acid (3), p-hydroxybenzoic acid (4), (E)-caffeic acid (5), ethyl trans-3, 4-dihydroxycinnamate (6), caffeic acid 4-O-beta-D-glucopyranoside (7), p-coumaric acid 4-O-beta-D-glucopyranoside (8), and 23(S)-12-O-caffeoyl-12-hydroxyllauric acid glycerol ester (9), separately. Among them, 1 and 9 are new compounds, and 3, 4, and 6 were isolated from Drynaria species for the first time.

[Analysis of fatty acids from the flowers of Trollius chinensis].

OBJECTIVE: To analyze and identify fatty acids from the flowers of Trollius chinensis Bunge. METHODS: To isolate and determine the constituents using GC/MS technique, quantitatively analyze their content by area normalization method. RESULTS: 31 fatty acids and 7 other constituents were isolated and determined. CONCLUSION: The major fatty acids were hexadecanoic (19.85%), (Z,Z)-9,12-octadecadienoic (14.37%), tetradecanoic (13.93%), (Z)-9-octadecenoic (13.00%), dodecanoic (6.79%), 10-hydroxy-hexadecanoic (4.37%) and octadecanoic (3.34%) acids.

Identification of light-independent inhibition of human immunodeficiency virus-1 infection through bioguided fractionation of Hypericum perforatum.

BACKGROUND: Light-dependent activities against enveloped viruses in St. John's Wort (Hypericum perforatum) extracts have been extensively studied. In contrast, light-independent antiviral activity from this species has not been investigated. RESULTS: Here, we identify the light-independent inhibition of human immunodeficiency virus-1 (HIV-1) by highly purified fractions of chloroform extracts of H. perforatum. Both cytotoxicity and antiviral activity were evident in initial chloroform extracts, but bioassay-guided fractionation produced fractions that inhibited HIV-1 with little to no cytotoxicity. Separation of these two biological activities has not been reported for constituents responsible for the light-dependent antiviral activities. Antiviral activity was associated with more polar subfractions. GC/MS analysis of the two most active subfractions identified 3-hydroxy lauric acid as predominant in one fraction and 3-hydroxy myristic acid as predominant in the other. Synthetic 3-hydroxy lauric acid inhibited HIV infectivity without cytotoxicity, suggesting that this modified fatty acid is likely responsible for observed antiviral activity present in that fraction. As production of 3-hydroxy fatty acids by plants remains controversial, H. perforatum seedlings were grown sterilely and evaluated for presence of 3-hydroxy fatty acids by GC/MS. Small quantities of some 3-hydroxy fatty acids were detected in sterile plants, whereas different 3-hydroxy fatty acids were detected in our chloroform extracts or field-grown material. CONCLUSION: Through bioguided fractionation, we have identified that 3-hydroxy lauric acid found in field grown Hypericum perforatum has anti-HIV activity. This novel anti-HIV activity can be potentially developed into inexpensive therapies, expanding the current arsenal of anti-retroviral agents.

Cytotoxic compounds of Schizolaena hystrix from the Madagascar rainforest.

Bioassay-guided fractionation of a crude ethanol extract from a Madagascar collection of Schizolaena hystrix afforded the two new long-chain compounds, 3 S-acetoxyeicosanoic acid ethyl ester ( 1) and 3 S-acetoxydoeicosanoic acid ( 2), and the known long-chain compound 3 S-acetoxyeicosanoic acid ( 3). In addition, the long-chain alcohol 1-hydroxydodecan-2-one ( 7), as well as the new flavonoid schizolaenone C ( 4) and the two known flavonoids diplacol ( 5) and 3'-prenylnaringenin ( 6) were isolated from a methanol extract of the same plant. Isolation and structure elucidation of the novel compounds and the cytotoxicities of all the isolates are reported.

Resin glycosides. XXV. Multifidins I and II, new jalapins, from the seed of Quamoclit x multifida.

Alkaline hydrolysis of the ether-soluble resin glycoside fraction of seeds of Quamoclit (Q.) x multifida, a hybrid between Q. pinnata and Q. coccinea, gave new glycosidic acids, multifidinic acids A and B, along with two known glycosidic acids, quamoclinic acid A and operculinic acid A, and three organic acids, (2S)-2-methylbutyric acid, n-decanoic acid and n-dodecanoic acid. Further, as major ether-soluble resin glycosides, new jalapins named multifidins I and II, were isolated accompanied by quamoclins I-IV, which were previously obtained from seeds of Q. pinnata. The structures of multifidins I and II, and multifidinic acids A and B have been determined on the basis of chemical and spectral data.