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The impact of different extraction methods, namely maceration, homogenizer-assisted extraction, rapid solid-liquid dynamic extraction, microwave-assisted extraction and ultrasound-assisted extraction, on polyphenols of Moringa oleifera leaves was studied. The phenolic composition of alcoholic (methanol 100%) and hydroalcoholic (methanol/water 50:50, v/v) extracts was compared by using an untargeted metabolomics-based profiling approach followed by multivariate statistics. With this aim, ultra-high-pressure liquid chromatography coupled to a quadrupole-time-of-flight mass spectrometry was used to profile phenolic compounds under the different extraction conditions. Besides, the in vitro antioxidant activities of Moringa leaves were also investigated as ferric reducing antioxidant power (FRAP) and oxygen radical absorbance capacity (ORAC). The metabolomic approach allowed to putatively annotate 262 phenolic compounds. In particular, glycosidic forms of quercetin (i.e., quercetin 3-O-galactoside, quercetin 3-O-glucoside, and quercetin 4’-O-glucoside) were the most represented compounds among flavonoids. Furthermore, protocatechuic acid was found to be the most abundant hydroxybenzaldheyde derivative, while the isomeric forms of hydroxybenzoic acid characterized the phenolic acids class. Overall, the extractions in methanol 100% were found to be the most effective for phenolic compounds recovering, when compared with those in methanol/water (50:50, v/v). Homogenizer-assisted extraction of M. oleifera leaves using 100% methanol allowed extracting the highest amounts of polyphenols (35.19 mg/g) and produced the highest oxygen radical absorbance capacity (536.27 μmol Trolox Equivalents/g). The supervised orthogonal projection to latent structures discriminant analysis identified phenolic acids as the phenolic class mostly affected by the different extraction technologies. These findings demonstrate that each extraction method promoted the recovery of specific phenolic subclasses with different efficiencies.

Ibervillea sonorae (Cucurbitaceae) is a Mexican plant commonly used by local population for its hypoglycaemic activity. Root extracts showed also other different biological activities, including antimicrobial, antifungal, antioxidant and anti-inflammatory activity. Main components of this plant are cucurbitacins, steroid-like triterpenes that possess, among others, antiproliferative activity. In previous studies, kinoin A and cucurbitacin IIb extracted from I. sonorae showed antiproliferative and apoptotic effects against different cancer cell lines. Based on all the above, a RP-HPLC method was developed and validated for the quantitative analysis of these two compounds in I. sonorae root extracts obtained with different extraction conditions. In the present study, the quantitative analysis of kinoin B diglycoside in all the extracts was performed as well. As a result, no direct correlation was found between the antiproliferative activity (IC50) against human cervical cancer cell line (HeLa) and the composition of the above three compounds. Only a slight statically significant negative correlation was observed between IC50s and the content of kinoin A (r = 0.29, p = 0.12), meaning that, at least in part, this is the main compound among the three, contributing to the antiproliferative activity on the real samples. Accordingly, a synergistic effect by the phytocomplex components can account for the observed antiproliferative activity of the methanolic extracts towards HeLa cells.

Background: Cucurbitacin IIb (CIIb) from Ibervillea sonorae has a high capacity to suppress cancer cell proliferation and induce apoptosis. This study investigated the molecular mechanisms related to the antiproliferative and apoptosis induction capacity of CIIb in HeLa cells. Materials and Methods: The cell viability and anti-proliferative effect of CIIb were evaluated by using the trypan blue exclusion assay. The effect of CIIb on the mitochondrial membrane potential was determined by flow cytometry using JC-1. The activity of caspase-3 and caspase-9 was evaluated by flow cytometry using commercial kits. The effect of CIIb on the cell cycle was investigated using Fluorescence-Activated Cell Sorting (FACS) analysis. Western blot analysis was used to evaluate both the inhibitory effect of CIIb on the STAT3 signaling pathway and cyclin –B1, and DNA damage by the comet assay. Results: CIIb triggers disruption of the mitochondrial membrane potential (Δψm) and consequently activated the caspases -3 and -9, as a result of the activation of the intrinsic pathway of the apoptosis. Likewise, the CIIbinduced cell cycle was arrested in S and G2/M after 24h of treatment. CIIb also reduced the expression of STAT3 and cyclin –B1. Finally, CIIb produced an antiproliferative effect at 48 and 72 h, inducing DNA damage. Conclusion: These results demonstrate CIIb-induced apoptosis and cell cycle arrest in HeLa through the inhibition of STAT3.

Commiphora erythraea (Burseraceae) resin derives from the bark injury of the plant, a small tree native to the Arabian Peninsula. The resin is commonly known as myrrh and it is traditionally used to protect livestock from ticks and to treat diseases related to inflammation. The resin is constituted by a volatile and a non-volatile fraction. The volatile fraction is a source of furanosesquiterpenoids among which furanodienone showed to be the most promising pharmacological active compound. The composition and pharmacological activities of the extracts and the isolated compounds have been reviewed.

Bursera microphylla (BM), one of the common elephant trees, is widely distributed in the Sonoran desert in Mexico. The Seri ethnic group in the Sonoran desert uses BM as an anti-inflammatory and painkiller drug for the treatment of sore throat, herpes labialis, abscessed tooth, and wound healing. Dried stems and leaves of BM are used in a tea to relieve painful urination and to stimulate bronchial secretion. Furthermore, BM is used for fighting venereal diseases. To investigate the effects of the hexane fraction of resin methanol extract (BM-H) on cell growth, the acute myeloid cell line (OCI-AML3) was treated with 250, 25, or 2.5 µg/mL of BM-H. The first 2 concentrations were able to significantly decrease OCI-AML3 cell number. This reduced cell number was associated with decreased S-phase, blockade of G2/M phase of the cell cycle, and increased cell death. Similar results were obtained on all tested tumor cell lines of different origins. We found that blockade of the cell cycle was a result of upregulation of p21 protein in a p53-independent way. Increase of p21 was possibly a result of upstream upregulation of p-ERK (which stabilizes p21 protein) and downregulation of p-38 (which promotes its degradation). Regarding cell death, activation of caspase-3, but not of caspase-8 or -9, was detectable after BM-H treatment. In conclusion, these data suggest that BM-H inhibited proliferation of cell lines mainly by a p21-dependent, p53-independent mechanism and promoted apoptosis through activation of caspase-3 but not caspase-8 or -9.

Two new lignans, namely 7-O-podophyllotoxinyl butyrate (1) and dihydroclusin 9-acetate (2), were isolated from the dichloromethane fraction of a methanol extract of Bursera microphylla (Burseraceae), along with eight known lignans (3–10). Their structures were determined by means of comprehensive spectroscopic analysis. Lignans 2–6 were tested for their anti-proliferative activity on the cancer cell lines LS180, A549 and HeLa, and on a non-cancer cell line, ARPE-19. Only compounds 4 and 5 showed an interesting activity on HeLa cells.

Industrial fermentations for the production of pharmaceuticals generate large volumes of organic wastes which disposal is, nowadays, an environmental and economic issue. In the present paper, the feasibility of energy and plant nutrients recovery from the pharmaceutical organic waste originated from a fermentative biomass used for the daptomycin production was investigated. To achieve this aim, an integrated anaerobic digestion-digestate composting treatment was evaluated, with the purpose of energy (biogas) and organic fertiliser (compost) production. Moreover, the effectiveness of the integrated biological treatment for xenobiotic degradation (e.g. daptomycin) was evaluated. The biomass was initially anaerobically treated to assess its suitability for the production of biogas. The yield in bio-methane obtained when the organic waste was treated in co-digestion with agricultural by-products was 396 Nm 3 t VS −1 . Once optimized the anaerobic digestion process, the produced digestate was composted in a pilot scale apparatus. The composting of the digestate produced an organic amendment rich in macro-nutrients (27.1, 6.2 and 17.8 g kg −1 of total N, P and K, respectively) and compatible with the Italian legislation concerning the production of fertilisers. No traces of daptomycin were detected in the compost, confirming the suitability of the integrated anaerobic-aerobic treatment for the removal of pharmaceuticals. Thus, through the anaerobic-aerobic treatment, it was demonstrated that energy and nutrients may be recovered from an organic waste which disposal, nowadays, is difficult.

Studies were made to increase the yield of piperine extraction using Naviglio Extractor® solid–liquid dynamic extractor (SLDE) from fruits of Piper longum. The effects of ratio w/v were investigated and optimised for the best method. The maximum yield of piperine (317.7 mg/g) from P. longum fruits was obtained in SLDE 1:50 ethanol extract. Extraction yields of piperine obtained from Soxhlet extraction, decotion (International Organization for Standardization) and conventional maceration extraction methods were found to be 233.7, 231.8 and 143.6 mg/g, respectively. The results of the present study indicated that Naviglio Extractor® is an effective technique for the extraction of piperine from long pepper.

Various essential oils (EO) have been individually evaluated to mitigate methane and ammonia production by rumen microbiota. Interactions between EO can affect their potency but such interactions largely remain unexplored. In the present study, EO from oregano, rosemary, Ceylon cinnamon, cinnamon leaves, cinnamon bark, dill seeds, and eucalyptus were chemically characterized and then evaluated in vitro , both individually (at 1.125 ml/L culture) and in three-way EO combinations (at total EO 0.8 ml/L, equal ratio), for their effects on fermentation, methanogenesis, ammoniagenesis, and bacteria and archaea. All the EO and their combinations decreased production of total gas (P Prevotella spp. (P . The EO combinations significantly decreased the abundances of archaea (P , and select groups or species of different rumen bacteria to different extents. Changes in bacterial and archaeal communities in response to several EO combinations were also shown by DGGE analyses. Combination of EO from Ceylon cinnamon, dill seeds, eucalyptus, and probably others, at low concentrations may be a practical approach to mitigate methane emission and nitrogen excretion from ruminant without adverse effect on feed digestion or fermentation.

The effect of the addition of ionic liquids (ILs) during the hydrodistillation of Myristica fragrans Houtt. (nutmeg) essential oil was studied. The essential oil of M. fragrans is characterized by the presence of terpenes, terpenoids, and of phenylpropanoids, such as methyl eugenol and safrole, that are regarded as genotoxic and carcinogenic. The aim of the work was to determine the best ionic liquid to improve the yield of the extraction of M. fragrans essential oil and decrease the extraction of toxic phenylpropanoids. Six ILs, namely 1,3-dimethylimidazolium chloride (1), 1,3-dimethylimidazolium dimethylphosphate (2), 1-(2-hydroxyethyl)-3-methylimidazolium chloride (3), 1-(2-hydroxyethyl)-3-methylimidazolium dimethylphosphate (4), 1-butyl-3-methylimidazolium chloride (5), and 1-butyl-3-methylimidazolium dimethylphosphate (6), were prepared by previously reported, innovative methods and then tested. An experimental design was used to optimize the extraction yield and to decrease the phenylpropanoids percentage using the synthesized ILs. The influence of the molarity of ILs was also studied. MODDE 12 software established 0.5 M 1-butyl-3-methylimidazolium chloride as the best co-solvent for the hydrodistillation of M. fragrans essential oil.

Collinin is a geranyloxycoumarins isolated in small amounts from plants of the Rutaceae family. Synthetic schemes were recently developed allowing to handle collinin in sufficient quantities to put in evidence valuable biological effects. The aim of this review is to examine the phytochemical and pharmacological properties of this compound.

A chemical study of the nonpolar fraction of a methanol-soluble extract of Bursera microphylla resin yielded a variety of di- and triterpenoids. In total, 15 compounds were isolated, of which three are new, namely, malabaricatrienone (1), malabaricatrienol (2), and microphyllanin (3). The antiproliferative activity of the major compounds was evaluated in different murine cancer cell lines (M12.C3.F6 and RAW264.7) and human cancer cells (A549, HeLa, and PC-3). The new compounds (1–3) did not show significant antiproliferative activity. The known compounds ariensin (4), burseran (5), and dihydroclusin diacetate (6) were effective against the RAW264.7 cell line, with IC50 values in the micromolar range.

Stilbenes, including resveratrol, are polyphenols provided with protective actions on the cardiovascular system. Some natural derivatives of resveratrol, like pterostilbene, have a better bioavailability than the parent compound. The aim of the present study was to prepare different substituted stilbenes (dimethylallyloxy-stilbene, dimethylallyloxy-pterostilbene) and compare them with resveratrol, p-hydroxy-stilbene and pterostilbene for their biologic activities on platelet aggregation, platelet radical oxygen species (ROS) production, and platelet nitric oxide (NO) synthesis. The results show that the increase of stilbene derivative lipophilicity enhances their biologic activities.

The use of aerial parts of Euphrasia pectinata Ten. usually known as Eyebright, is one of the commonest folk remedy in many European and Asian countries to treat eye problems. By a bioassay-guided fractionation of the dichloromethane fraction of E. pectinata methanolic extract, following the antiproliferative activity on different cancer cell lines (MCF-7, HeLa, LNCaP, ACHN and C32), the new iridoid euphrasin ( 1 ), and the known campsinol ( 2 ), artselaenin A ( 3 ), and artselaenin B ( 4 ) were isolated. The structure of euphrasin ( 1 ) was determined by spectroscopic methods. All compounds screened by SRB assay exhibited antiproliferative activity in a concentration dependent-manner. In particular, euphrasin ( 1 ) showed a promising activity against LNCaP and HeLa cells with IC50 values of 0.1 and 0.2 μM, respectively. Signficative results were also obtained with campsinol ( 2 ) with IC50 value of 1.9 μM on endometrial cancer cells.

The effects of increasing concentrations of oregano (Origanum vulgare L.) and rosemary (Rosmarinus officinalis L.) essentials oil (EO) on ruminal gas emissions were tested in vitro using 50 mL serum bottles. Each bottle contained a 200 mg substrate (alfalfa hay and corn meal 1:1) and a 20 mL solution composed of a buffered medium and rumen fluid (1:2). The percentage of ruminal fermentation products was quantified by an infrared analyzer. The reduction of total gas production was 6% and 9% respectively when using the 1.5 and 2.0 g/L oregano EO measurements. The reduction of methane production was 55%, 72% and 71% respectively with regard to the 1.0, 1.5 and 2.0 g/L oregano EO doses, while rosemary EO (2.0 g/L) reduced the methane production by 9%. The production of ammonia was significantly reduced (59%–78%) by all treatments with the exception of rosemary EO at the lowest dose. Dry matter and neutral detergent fiber degradability was reduced by most of the treatments (respectively 4%–9% and 8%–24%). The total volatile fatty acids (VFA) concentration was markedly decreased by oregano EO and was not affected by rosemary EO. Both EOs mitigated rumen fermentations, but oregano EO gave rise to the highest reduction in methane and ammonia production. However, further research is needed to evaluate the use of these essential oils as dietary supplements by taking into account the negative effects on feed degradability.

The total phenolic content, antioxidant and antifungal activities of three Inula crithmoides extracts (n-hexane, methylene chloride and MeOH) were investigated. The methanolic extract showed the highest total phenolic content. In the DPPH assay, the methanolic and hexane extracts exhibited the highest DPPH-radical scavenging activity; in the 5-lipoxygenase assay, the hexane extract showed greater inhibitory effect with an IC50 similar to that of Trolox and ascorbic acid. The antifungal activity of the methanolic extract revealed a higher activity against Phytophtora cryptogea and Alternaria solani.

Two new cyathane diterpenes, cyrneines A (1) and B (2), were isolated from the mushroom Sarcodon cyrneus. The structures of the novel diterpenoids were determined by analysis of their spectroscopic data. Neither cyrneine A nor cyrneine B at 100 microM showed cytotoxicity as determined by LDH analysis. The stimulating activity on neurite outgrowth of cyrneines was evaluated. Rat pheochromocytoma cells (PC12), used as a model system of neuronal differentiation, were cultured with cyrneine A (100 microM), cyrneine B (100 microM) or NGF (100 ng/ml) for 24 h. Interestingly, cyrneines A and B significantly promoted neurite outgrowth in addition to NGF as a positive control.

Shoot multiplication of Thymus mastichina L. was achieved on media containing 0.1 mg l−1 6-benzyladenine and/or 0.1 mg l−1 indole-3-butyric acid, or in hormone-free medium (control). The growth of plantlets, the production and composition of the essential oil, the density and secretory stage of glandular hairs have been evaluated in the presence and absence of growth regulators and triacontanol. We observed a positive effect of triacontanol on the growth of micropropagated plantlets using different conditions. Media with different levels of BA, IBA and TRIA resulted in no differences in the composition of the essential oil produced by plantlets. The major components of the oil were 1,8-cineole and linalool. An increase in the oil yield was observed especially when triacontanol was added to hormone-free medium. There was no correlation between changes in the oil yield and glandular hairs density, but the yield was dependent on the secretory stage of the glands.

Potassium exchanged layered zirconium phosphate catalyzed Knoevenagel condensation of aldehydes and active methylene compounds gave the corresponding E configurated olefinic derivatives in solvent free conditions.

A convenient method for the ring opening of epoxides by aromatic amines, catalysed by zirconium sulfophenyl phosphonate in solvent-free conditions, is described.

Four coumarin derivatives [selidinin 1, (+)-praeruptorin A 2, visnadin 3 and (R)-(+)-7-(2′,3′-epoxy-3′-methylbutoxy)-coumarin 4] were isolated from the aerial parts of Ligusticum lucidum Mill. subsp. cuneifolium (Guss.) Tammaro (Apiaceae). This is the first report on the identification of these compounds in the Ligusticum genus. Their topical antiinflammatory activity was evaluated as the inhibition of croton oil-induced ear dermatitis in mice. Each compound (0.3 μmol/cm2) induced a significant oedema reduction and compound 4 exerted an effect similar to that of the equimolar dose of the reference drug indomethacin. Copyright © 2010 John Wiley & Sons, Ltd.

Layered zirconium hydrogen phosphonate exchanged with the potassium ion was found to be an efficient heterogeneous catalyst for the hydrolysis of sterically hindered phenolic silyl ethers.

The Kanematsu transformation was employed for the preparation of tetrahydroisobenzofuran-4-carboxylic acid (12), α-methylation, subsequent conversion into the diazoethanone 14, and, finally, treatment with dirhodium tetraacetate of which furnished the hydrindanone 1 of the steroid C-D ring structure.

This paper presents preliminary results on attempts to extract and characterize the volatile secondary metabolites contained in needles of differentPinus species and to ascertain the role played by these substances on the behavior ofThaumetopoea pityocampa (Denis et Schiffermuller) females, which show a marked preference, during the oviposition period, for some indigenous and exotic species of host plants existing in mixed formation. Limonene is the most abundant monoterpene extracted fromP. pinea needles, the least favored species of pine processionary caterpillar (PPC) females, although it is present in only very low amounts in otherPinus species. An increase was observed in limonene production byP. pinea at the start of the flight period of the PPC adult, and subsequently at the beginning of the females’ oviposition period. Assays carried out in two pine stands in central Italy showed that limonene, emulsified with water and sprayed on foliage of four different pine species plants,P. sylvestris, P. nigra, P. pinaster andP. radiata, during the PPC oviposition period, provided a satisfactory degree of protection. In fact, the number of egg clusters collected from treated plants was often lower than the number of egg clusters collected from control plants and was comparable to the number of egg clusters laid onP. pinea plants. In particular (R)-(+)-limonene, although not produced in nature by pines, was the most effective deterrent. However, the effect of (S)-(-)-limonene, the enantiomer biosynthesized by pines, was also adequate.

A mild and efficient process for one-step conversion of oximes into gem -halo-nitro compounds using Oxone® and sodium chloride or potassium bromide is described.

A mild and convenient oxidative Nef reaction using Oxone® (potassium hydrogen persulfate) is described. Following our procedure primary and secondary nitroalkanes generate carboxylic acids and ketones, respectively, both in good yields. †Deceased on January 1st 1998

Glaucopine A (1) and B (2), two new cyathane diterpenes, have been isolated from the mushroom Sarcodon glaucopus: their structures have been determined on the basis of spectral data. Their topical anti-inflammatory activity was evaluated using the Croton oil ear test in mice: compounds 1 and 2 (1 micromol/cm2) provoked edema reduction (62 % and 55 %, respectively) similar to that induced by the reference non-steroidal anti-inflammatory drug, indomethacin (0.3 micromol/cm2, 61 % edema reduction).

The chemical composition, the antiradical properties of Dendrobium speciosum (Orchidaceae) leaves and stem extracts have been studied. Furthermore, in view of the use of this orchid as "bush foods", the genotoxic/antigenotoxic effects of the extracts have been evaluated.

Layered α-zirconium sulfophenylphosphonate-methanphosphonate is a solid acid catalyst that catalyzes Ferrier rearrangement from d-glycals and alcoholic nucleophiles under mild reaction conditions in short time and good yields. Notably, the combination of α-zirconium sulfophenylphosphonate-methanphosphonate and lithium bromide change the regioselectivity of this process affording 2-deoxy sugars in good yields.