Silvia Maietti

trans-Resveratrol in Nutraceuticals: Issues in Retail Quality and Effectiveness

Fourteen brands of resveratrol-containing nutraceuticals were evaluated in order to verify their actual resveratrol content and to control if their health-promoting properties are related to manufacturing quality. Products included pure resveratrol capsules or multi-ingredient formulations with standardized amounts of resveratrol and other phytochemicals. Samples were analyzed for total trans-resveratrol, flavonoids, procyanidin, polyphenol content and the results were compared with the content declared on-label. Only five out of 14 brands had near label values, compliant with Good Manufacturing Practices (GMP) requirements (95–105% content of active constituent), four products were slightly out of this range (83–111%) and three were in the 8–64% range. Two samples were below the limit of detection. The greater the difference between actual and labeled resveratrol content, the lower was the antioxidant and antiproliferative activity strength. Dietary supplements containing pure trans-resveratrol exhibited a greater induction of differentiation towards human leukemic K562 cells when compared to multicomponent products. Great differences currently exist among resveratrol food supplements commercially available and GMP-grade quality should not be taken for granted. On the other side, dosages suggested by most “pure”, “high-dosage” supplements may allow a supplementation level adequate to obtain some of the purported health benefits.

Asymmetric epoxidation of cinnamic acid derivatives using dioxiranes generated in situ from dehydrocholic acid

Abstract The asymmetric epoxidation of different cinnamic acid derivatives in water–NaHCO 3 has been achieved using dehydrocholic acid as the optically active ketone and Oxone® as the oxygen source (with product e.e. values of up to 75%).

Epoxidation of electrophilic alkenes in ionic liquids

A fast and efficient procedure is proposed for the epoxidation of electrophilic alkenes, the structures of which resemble the vitamin K class, in ionic liquids as solvents and using aqueous basic solutions of hydrogen peroxide as oxidant. Yields of epoxides ranging from very good to almost quantitative are observed for all the substrates analysed.

Phytochemical analysis and cytotoxicity towards multidrug-resistant leukemia cells of essential oils derived from Lebanese medicinal plants.

Juniperus excelsa fruit essential oil as well as J. oxycedrus, Cedrus libani, and Pinus pinea wood essential oils have been obtained with yields between 2.2 ± 0.3 % to 3.4 ± 0.5 % and analyzed by gas chromatography. Sesquiterpenes mainly characterized C. libani and J. oxycedrus essential oils, while in P. pinea and J. excelsa, monoterpenes were the most abundant compounds. In J. oxycedrus, cis-calamenene (7.8 %), cuparene (3.8 %), and cis-thujopsenal (2.0 %) have been detected for the first time. The cytotoxic activity of these essential oils against drug-sensitive CCRF-CEM and multidrug-resistant P-glycoprotein-expressing CEM/ADR5000 leukemia cells has been investigated (IC₅₀ values: 29.46 to 61.54 µg/mL). Remarkably, multidrug-resistant CEM/ADR5000 cells did not reveal cross-resistance, indicating that these essential oils might be useful to treat otherwise drug-resistant and refractory tumors.

Antifungal activity of essential oil from fruits of Indian Cuminum cyminum

The essential oil of fruits of Cuminum cyminum L. (Apiaceae), from India, was analyzed by GC and GC-MS, and its antifungal activity was tested on dermatophytes and phytopathogens, fungi, yeasts and some new Aspergilli. The most abundant components were cumin aldehyde, pinenes, and p-cymene, and a fraction of oxygenate compounds such as alcohol and epoxides. Because of the large amount of the highly volatile components in the cumin extract, we used a modified recent technique to evaluate the antifungal activity only of the volatile parts at doses from 5 to 20 µL of pure essential oil. Antifungal testing showed that Cuminum cyminum is active in general on all fungi but in particular on the dermatophytes, where Trichophyton rubrum was the most inhibited fungus also at the lowest dose of 5 µL. Less sensitive to treatment were the phytopathogens.

Selective removal of monoterpenes from bergamot oil by inclusion in deoxycholic acid.

A new approach for removing monoterpenes (MTs) from bergamot oil by selective inclusion in deoxycholic acid (DCA) is proposed. The inclusion process is very efficient, the included fraction being composed mainly of limonene (71.7%) and gamma-terpinene (19.8%). On the other hand, the deterpenated bergamot oil fraction showed for the linalool and linalyl acetate derivatives significant increases from 16.6 and 21.4% to 18.3 and 42.2%, respectively. The major advantages of this methodology are its simplicity, the mild conditions employed, and the quantitative recovery of both host (DCA) and guest (monoterpenes) compounds. Differential scanning calorimetry (DSC), thermal gravimetry (TG), powder X-ray diffractometry (XRPD), infrared spectroscopy (IR), and proton magnetic resonance ((1)H NMR) analysis were used to investigate and characterize the inclusion compounds.

Expression of pro-inflammatory interleukin-8 is reduced by ayurvedic decoctions.

Eleven decoctions, obtained from indian plants widely used in ayurvedic medicine, have been investigated as a possible source of molecules exhibiting biological activity on the interaction between DNA and NF‐kB, a transcription factor involved in the expression of proinflammatory genes. Cystic fibrosis (CF) cell line stimulated by TNF‐α has been used as inflammatory cellular model to determinate interleukin‐8 (IL‐8), one of the most relevant pro‐inflammatory mediator in CF regulated by the NF‐kB. The chemical characterization of these 11 decoctions by spectrophotometric analysis and NMR fingerprinting highlighted that sugars and polyphenols seemed to be the main compounds. Our results demonstrated that Azadirachta indica, Terminalia bellerica, Terminalia chebula, Hemidesmus indicus, Emblica officinalis and Swertia chirata are the most active decoctions in inhibiting NF‐kB/DNA interactions by EMSA assay and in reducing pro‐inflammatory IL‐ 8 expression in CF cells at IC50 concentrations by Real‐Time and Bio‐plex analyses. Finally, we observed the increase of all inhibitory activities with the rise of total polyphenols, procyanidins and flavonoids, except for the levels of IL‐8 mRNA accumulation, that were as high as flavonoid content grown up by the statistical multivariate analyses. In conclusion, these six decoctions might be interesting to explore new anti‐inflammatory treatments for diseases, such as CF. Copyright

Phytotoxic Effects and Phytochemical Fingerprinting of Hydrodistilled Oil, Enriched Fractions, and Isolated Compounds Obtained from Cryptocarya massoy (Oken) Kosterm. Bark.

The hydrodistilled oil of Cryptocarya massoy bark was characterized by GC‐FID and GC/MS analyses, allowing the identification of unusual C10 massoia lactone (3, 56.2%), C12 massoia lactone (4, 16.5%), benzyl benzoate (1, 12.7%), C8 massoia lactone (3.4%), δ‐decalactone (5, 1.5%), and benzyl salicylate (2, 1.8%) as main constituents. The phytotoxic activities of the oil, three enriched fractions (lactone‐rich, ester‐rich, and sesquiterpene‐rich), and four constituents (compounds 1, 2, 5, and δ‐dodecalactone (6)) against Lycopersicon esculentum and Cucumis sativus seeds and seedlings were screened. At a concentration of 1000 μl/l, the essential oil and the massoia lactone‐rich fraction caused a complete inhibition of the germination of both seeds, and, when applied on tomato plantlets, they induced an 85 and 100% dieback, respectively. These performances exceeded those of the well‐known phytotoxic essential oils of Syzygium aromaticum and Cymbopogon citratus, already used in commercial products for the weed and pest management. The same substances were also evaluated against four phytopathogenic bacteria and ten phytopathogenic fungi, providing EC50 values against the most susceptible strains in the 100–500 μl/l range for the essential oil and in the 10–50 μl/l range for compound 6 and the lactone‐rich fraction. The phytotoxic behavior was related mainly to massoia lactones and benzyl esters, while a greater amount of 6 may infer a good activity against some phytopathogenic fungi. Further investigations of these secondary metabolites are warranted, to evaluate their use as natural herbicides.

Comparative antiproliferative activities of wood and seeds essential oils of Juniperus oxycedrus L. against K562 human chronic myelogenous leukemia cells

The species Juniperus oxycedrus L. is a member of Cupressaceae family. The chemical composition and antiproliferative activity of wood and seeds essential oils of J. oxycedrus, grown wild in Lebanon, were evaluated in order to investigate whether these products could be used as sources of functional compounds. The most abundant components of the seeds essential oils were α-pinene, β-myrcene, limonene and δ-cadinene, while wood oil components included δ-cadinene, cis-thujopsene, τ-muurolol, widdrol, epi-cubenol, β-caryophyllene and α-calacorene. Both wood and seeds essential oils inhibited the proliferation of K562 cell line with ic50 values of 39.8±2.7 and 147.7±3.6 μg/mL, respectively. The J. oxycedrus wood oil showed erythroid differentiation of 16.0±2.0% at a concentration of 5 μg/mL, while the seeds essential oil showed erythroid differentiation of 25.0±2.8% at a concentration of 50 μg/mL.