Catalytic transformation of copaiba (Copaifera officinalis) oil over zeolite ZSM-5

The oil extracted from the trunk of the copaiba tree (Copaifera officinalis) is composed of sesquiterpenes, C₁₅H₂₄, and a small amount (>7 %) of sesquiterpenols, C₁₅H₂₆O; these were identified from their Kováts indices and mass spectra. The use of zeolites in the catalytic transformation of this renewable source of hydrocarbons is of interest in the search for new chemicals and ecologically clean fuels. Oil samples from copaiba trees growing in Colombia's Oriental Plains were circulated over zeolite ZSM-5 in a continuous flow fixed-bed micro reactor at 225, 265, and 325°C, for 1 h and subsequently analyzed by HRGC and GC-MS. Whereas only thirty four sesquiterpenes were identified in the original oil, over two hundred compounds were found in the product of the treatment of copaiba oil with zeolite ZSM-5. This complex mixture of sesquiterpenes, light aromatic compounds, and indene and naphthalene derivatives resulted from reactions such as isomerization, hydrogenation, cracking, and dehydrogenation with and without cracking. The amount of cracking products and aromatic compounds increased with reactor temperature but decreased with catalyst aging.     

Chemical composition and biological activities of essential oil from Filifolium sibiricum (L.) Kitam

The essential oil from Filifolium sibiricum (L.) Kitam were extracted using hydrodistillation and GC-MS was used to analyse the essential oil. The main components were espatulenol (8.55%), geranyl acetate (8.03%), caryophyllene oxide (5.47%), calamenene (4.79%), geraniol (4.28%), calamenene (4.53%), geraniol (4.06%), cedrene epoxide (3.23%), myrtenol (3.18%), transgeranylgeranio (3.13%), etc. The essential oil showed intensive inhibitory effects against MCF-7 with IC₅₀ level of 0.78 mg/mL, HepG-2 with IC₅₀ level of 0.44 mg/mL, SKOV-3 with IC₅₀ level of 0.27 mg/mL, BGC-823 with IC₅₀ level of 0.34 mg/mL. In the antibacterial test, the essential oil showed the significant antibacterial activities. The MIC and MBC values were 5.20 and 5.20 mg/mL against Staphylococcus aureus.     

Chemistry and biological activities of CO-releasing molecules (CORMs) and transition metal complexes

The advent of CO as a small molecule that, in addition to NO, elicits essential biological functions has initiated the search for compounds and complexes capable of releasing CO in a well defined manner under physiological conditions. Since some pharmacological and therapeutic effects of CO have been established in preclinical studies, tailor-made CO-releasing molecules (CORMs) which could be utilized as pharmaceuticals could be of great benefit for many patients. Release of CO(2) is one of the most common features in chemistry and NO producing molecules are very well established but compounds with CO-releasing properties are rare. Some of the more promising candidates and molecules under study are discussed in this article. Furthermore, molecules that possess intrinsic features to serve as potential CO-RMs and merit in depth investigations are proposed. The focus is thereby on main group compounds and on transition element complexes. It should be emphasized that CORMs not only have encouraging prospects as therapeutic agents but may also be significant for synthetic pathways to novel complexes containing the CO ligand. To underline the prospects of CORMs, the chemical part is embedded in a biological and medicinal context.     

Oxyfunctionalization products of terpenoids with dimethyldioxirane and their biological activity

Oxyfunctionalization of the bioactive terpenoids, ursolic acid acetate (1), oleanolic acid acetate (5), lupeol acetate (12), and kaurenic acid (17), with dimethyldioxirane (DMDO) was investigated. Treatment of the terpenoids with DMDO under mild conditions afforded a variety of oxidation and oxydegradation products to yield naturally occurring and/or novel compounds in one step. After chromatographic separation, the structures of the individual isolated products were determined using spectroscopic methods including several homonuclear (1H-1H) and heteronuclear (1H-13C) shift-correlated 2D-NMR techniques. The inhibitory activity of the terpenoid derivatives against alpha-glucosidase was investigated and compounds 1, 3, 7, and 9 were found to exhibit potent activity.     

Chemistry and biological activity of essential oils from Piper claussenianum (Piperaceae)

Analyses of essential oils obtained from fresh and dried leaves and inflorescences of Piper clausenianum were performed using GC-FID, GC-MS and NMR techniques. Forty compounds were detected for these four oils with the total of identified constituents ranging from 88.7% for the dried inflorescences to 97.7% for the dried leaves. Sesquiterpenes were the main constituents in the volatile fraction from leaves with a high percentage of (E)-nerolidol (up to 83%). However, monoterpenes were identified in greater amount in the inflorescences, with linalool percentages from 50% up. The essential oils from fresh leaves and inflorescences were submitted to anti-parasitic activity against a strain of Leishmania amazonensis. Both samples showed biological activity, but the essential oil from P. claussenianum fresh leaves, which was rich in (E)-nerolidol, showed effective growth inhibition of L. amazonensis due to the high percentage of this metabolite in the mixture.     

Use of spinning band distillation equipment for fractionation of volatile compounds of Copaifera oleoresins for developing a validated gas chromatographic method and evaluating antimicrobial activity

Copaifera is a tree that produces an oleoresin that has great historical and economic importance. These oleoresins display several pharmacological properties, such as anti‐inflammatory and antimicrobial, among others. The commercialization of Copaifera oleoresin occurs, in many cases, without any quality control, which facilitates its adulteration. Validated analytical methods can provide a safe quality control. In this work, the 800 Automatic Spinning Band Distillation equipment was used to perform the fractionation of the volatile oils obtained by hydrodistillation of Copaifera multijuga, C. paupera, C. Publifora and C. langsdorffii, aiming to isolate and purify the major compounds present in these oils. For purification, classical column chromatography was used, furnishing six isolated sesquiterpenes. The sesquiterpenes were used as standards in the development and validation of the method by GC–FID. The evaluated parameters were selectivity, linearity, precision, accuracy and robustness and they are all in accordance with ANVISA and International Conference on Harmonization guidelines. The developed method is reliable for the quantification of sesquiterpenes in Copaifera oleoresins. Both volatile oils and isolated sesquiterpenes had their minimum inhibitory concentration determined against strains of Gram‐negative and Gram‐positive bacteria and yeasts. Copaifera langsdorffi oleoresin was the only one active against all of the evaluated microorganisms, displaying good antimicrobial potential.     

Diterpenoids from Isodon species and their biological activities

Isodon species (Labiatae) are widely distributed plants, many of which are used in folk medicine. Over the past twenty years, they have received considerable phytochemical and biological attention. Thestructures of their many diterpenoids constituents, especially those with an ent-kaurane skeleton, have been elucidated. The significant phytochemical and pharmacological diterpenoids form the subject of this review. There are 290 references.     

Screening of several biological activities induced by different sesquiterpene lactones isolated from Centaurea behen L. and Rhaponticum repens (L.) Hidalgo

This study aims to evaluate the in vitro cytotoxic, in vitro and in ovo anti-angiogenic effects and antimicrobial activity of sesquiterpene lactones (SLs) from two plants Centaurea behen and Rhaponticum repens (L.). Five SLs, including cynaropicrin (1), 4β,15-dehydro-3-dehydrosolstitialin A (2), aguerin B (3), janerin (4), cebellin E (5), and a flavone hispidulin (6) were isolated from C. behen (compounds 1–3) and R. repens (compounds 4–6). Cynaropicrin (1) and aguerin B (3) were characterised by strong cytotoxic activities against A2780 cells with IC₅₀ values of 1.15 and 1.62 μg mL^?1, respectively, comparable to that of doxorubicin (IC₅₀ = 1.17 μg mL^?1). The anti-angiogenic study showed the remarkable inhibitory effect of cynaropicrin (1) and aguerin B (3) on the proliferation and migration of HUVECs. In addition, cynaropycrin and aguerin B exhibited significant angio-inhibitory effects in CAM assay. These findings may be useful for the development of novel chemotherapeutic agents for the treatment of cancer.     

Sesquiterpenoids from Curcuma wenyujin dreg and their biological activities

Four new sesquiterpenoids,4,8-dioxo-6β-hydroxyl-7β,1 1-epoxycarabrane(1),4,8-dioxo-6β-hydroxyl-7,1 1-epoxycarabrane(2),wenyujinins Q and R(3-4),and nine known sesquiterpenoids(5-13) were isolated from the Curcuma wenyujin(C wenyujin) dreg.Their structures and relative configurations were elucidated using 1D,2D NMR,and HR-ESI-MS data.All the compounds were isolated for the first time from the C.wenyujin dreg and evaluated for their antibacterial and antifungal activities.Compounds 3,5-8 exhibited strong broad-spectrum antifungal activities against tested nine pathogenic fungi.     

Chemical constituents and biological activities from branches of Colubrina asiatica

Sixteen compounds were isolated from a Thai medicinal plant, Colubrina asiatica. The isolated compounds were elucidated on the basis of spectroscopic methods (IR, 1D and 2D NMR) as six triterpene acids (1–6), five steroids (7–11), one benzoic acid derivative (12), two peptides (13 and 14), one sesquiterpenoid (15) and one jujubogenin (16). Compounds 3 and 10 showed antimalarial activity against Plasmodium falciparum. Compound 5 showed antimycobacterial activity. Moreover, compounds 3, 5, 6, 10 and 14 exhibited weak cytotoxicity against cancer cell lines. Compounds 1–15 have been isolated for the first time from this plant.     

Chemical composition and biological activities of the essential oil from Pulicaria undulata (L.) C. A. Mey. growing wild in Egypt

Abstract

Pulicaria undulata is used as a traditional herbal remedy in Egypt. We used gas chromatography-mass spectrometry for analysis of essential oil of this plant growing wild in Egypt and 64 compounds were identified. The oil was rich in oxygenated monoterpenes (64.0%) and aromatic derivatives (18.8%). The major components were carvacrol (46.5%), xanthoxylin (18.1%) and carvotanacetone (8.7%). The oil of the Egyptian plant showed significant differences from the oil results reported on this species derived from different accessions. Antioxidant activity was performed by FRAP, DPPH and ABTS assays, and the oil demonstrated a powerful antioxidant properties. Furthermore, cytotoxicity was assessed using MTT assay against three cell lines (A375, T98G, HCT116) and the oil showed moderate results with IC₅₀ of 18.53, 40.64 and 22.23?μg/ml; respectively. The oil showed a good anti-acetylcholinesterase activity (IC₅₀?=?139.2?μg/ml) using Ellman method. In conclusion, the studied oil exhibited a peculiar fingerprint and promising biological activities.     

Chemistry and biological significance of essential oils of Cymbopogon citratus from Pakistan

Steam distilled oil of Cymbopogon citratus was analyzed by Gas Chromatographic-Mass Spectrometry (GC-MS) and citral was found as major constituent. The oil exhibited significant inhibition of beta-glucuronidase activity and also showed activities against some tested human, plant and animal pathogens. The minimum inhibitory concentrations could not be determined due to the lack of some chemicals.     

Biosynthesis of Nickel oxide Nanoparticles from Euphorbia heterophylla (L.) and their biological application

Nickel oxide Nanoparticles (NiO NPs) were synthesized from E. heterophylla (L.) leaves extract act as reducing/capping agent by biosynthesis process. Further the synthesized NiO NPs was subjected for structural, optical and biological properties. The XRD pattern of NiO NPS exhibit face centred cubic (FCC) crystalline structure. The UV-DR spectrum of biosynthesized NiO NPs exhibited optical properties with well-defined at 321 nm and its exhibits optical band gap is 3.24 eV. The FT-IR spectrum of NiO NPs shows stretching vibration of Ni-O at 452 cm⁻¹. The morphological features of NiO NPs are rhombohedra and slightly agglomerated and then size of the biosynthesized NiO NPs as found in the range of 12–15 nm. The NiO NPs shows vital non-toxic properties on human erythrocytes and its interference in activity coagulation cascade both on PRP and PPP on human blood. The Bactericidal activity of NiO NPs was shows significant inhibitory activity against pathogenic bacterial strains. Further, NiO NPs show significant cytotoxicity against human lung cancer cell line (A549) and human hepatocarcinoma (HepG2) cell lines. Therefore, the study reveals states that, the E. heterophylla (L.) leaves extract is an effective reducing/capping agent for the formation of NiO NPs and its exhibits biological properties.     

New isolates from leaves of Nicotiana tabacum and their biological activities

Three new isolates (1?3) including one new sterol and two new flavonoids together with three known sterols (4?6) were isolated from the leaves of Nicotiana tabacum. Their structures were determined mainly by spectroscopic methods, including extensive 1D and 2D NMR techniques. All compounds were evaluated for their anti-tobacco mosaic virus and cytotoxic activities. The results showed that compounds 2 and 3 exhibited high anti-TMV activity with inhibition rate of 34.2 and 33.4%, respectively, which were roughly equivalent to that of positive control. The cytotoxicities of compounds 1 and 4–6 against five human tumour cell lines were also tested, and tested compounds showed weak inhibitory activities against some tested human tumour cell lines.     

Iridoids from the roots of Valeriana jatamansi and their biological activities

A new iridoid, jatamandoid A (1), and four known analogues (2-5) were isolated from the roots of Valeriana jatamansi. Their structures were elucidated on the basis of extensive spectroscopic analysis (IR, ESI-MS, HR-ESI-MS, 1-D and 2-D NMR). Five compounds were evaluated and compounds 1, 2 and 5 showed moderate neuroprotective effects against MPP(+)-induced neuronal SH-SY5Y cell death.     

Harvesting season dependent variation in chemical composition and biological activities of the essential oil obtained from Inula graveolens (L.) grown in Chebba (Tunisia) salt marsh

The chemical composition and the biological activities of aromatic plants may be influenced by seasonal changes. Therefore, the essential oil of Inula graveolens (IGEO), collected at Chebba salt marsh, was studied in terms of yields, compositions and biological activities, throughout four different seasons, namely spring, summer, autumn and winter (April, July, October and January, respectively). GC/MS analysis identified 30 compounds. Mostly quantitative rather than qualitative, variation was observed in the oil composition of each sample. It had been revealed a predominant presence of bornyl acetate and borneol, as well as significant differences of several compound amounts in function of the seasonal change. Biological activities were also related to the harvest season; hence, IGEO from spring gave the best antioxidant activity results and IGEO from autumn seemed to be the most potent against pathogenic microorganisms, while oils from summer and winter were the strongest inhibitors of acetylcholinesterase and tyrosinase.A matrix linking IGEO major compounds to biological was composed to identify relationships between concentrations of the volatile molecules and the biological activities of the samples. Furthermore, the seasonal variation of these main volatile constituents was also investigated through principal compound analysis (PCA). The obtained results revealed that each biological activity depends on the seasonal fluctuation of the amounts of certain chemical compounds.     

Synthesis and biological activities of flavolipids

Syntheses of the bacterial surfactants 6S,6S-, 9S,9S-, and 9U,9U-flavolipids confirmed the structures proposed for them from spectroscopic analysis of a flavolipid mixture and made pure flavolipids available for the first time. All three synthetic flavolipids and a straight chain analogue were found to be weakly cytotoxic and to inhibit metastatic cancer cell migration, with 9U,9U-flavolipid (the most abundant natural flavolipid) having the most activity. Biosynthetic routes to the branched side-chains of the flavolipids are suggested, and it is proposed that branched chains are employed to hinder biodegradation.     

Enzyme pretreatment improves the recovery of bioactive phytochemicals from sweet basil (Ocimum basilicum L.) leaves and their hydrodistilled residue by-products,and potentiates their biological activities

In the present study, the effect of enzyme pretreatment on essential oil recoveries from sweet basil (Ocimum basilicum L.) leaves was evaluated. Moreover, the consideration on the use of hydrodistilled residue by-products as a source of bioactive phytochemicals with antioxidant, antimicrobial, and repellent effects against the stored-grain pest Tribolium castaneum was examined. Results showed that the enzymatic pretreatment increased the extraction yield of essential oil by 400, 417, and 478% in hemicellulase-, cellulase-, and viscozyme-treated samples, respectively. Phenylpropanoids including methyl cinnamate, methyl eugenol, eugenol and estragol were found as the main components, and were particularly abundant in cellulase-treated samples. From the hydrodistilled residue of enzyme-treated samples, better recoveries of total phenols (TPC) (258.3–470.9 mg GAE/g extract) and flavonoids (TFC) (59.4–94.3 mg QE/g extract) were observed. Using the DPPH, ABTS, and FRAP assays, a strong antioxidant activity of the rosmarinic-rich extract was observed. Such an activity which was mediated through electron transfer mechanism was highly correlated with the TPC, TFC and rosmarinic acid content. The in vitro bioassay showed that methanol extract (6.29 and 12.58 µL/cm²) had repellent activity against the stored-grain pest Tribolium castaneum. These results suggest the potential of enzyme pretreatment to promote the use of hydrodistilled residue by-products as a valuable source of natural antioxidants and repellents ingredients.     

Two new terpenoids from fruits of Ziziphus jujuba

One new ceanothane-type triterpene and one new sesquiterpene,together with two known triterpenes were isolated from the fruits of Ziziphus jujuba Mill.(Rhamnaceae).Based on the spectral analyses,the structures of two new compounds were elucidated as 2α-aldehydo-A(1)-norlup-20(29)-en-27,28-dioic acid(zizyberanal acid)(1),and zizyberanone(2).While the two known triterpenes were identified as zizyberanalic acid(3)and ursofic acid(4).