Records of Natural Products Articles

Macula lutea, is the center of the retina of the eye, contains high concentrations of lutein and zeaxanthin which can act as a filter against short-wavelength (blue) light. Lutein and zeaxanthin are the only carotenoids detected in human lens which exhibit highly strong free radical scavenging activity. Many epidemiological studies, clinical trials, animal experiments have suggested that lutein and zeaxanthin have anti-inflammatory potential with their high antioxidant properties. Several eye diseases including, age-related macular degeneration, uveitis and retinitis pigmentosa are caused by ocular inflammation. Some studies have shown that lutein and zeaxanthin could be protective, curative and preventive against ocular inflammation induced diseases and other ocular disorders such as cataract, glaucoma and choroideremia. The mechanisms responsible for these effects are absorption of near-ultraviolet and blue light, reduction of oxidative stress, inflammation and angiogenesis. Lutein and zeaxanthin can be taken from dietary supplements or a diet high in fruits, vegetables such as kale, spinach and turnip greens. The aim of this review is to evaluate the relationship between the consumption of lutein and zeaxanthin and eye diseases.

A new pregnane-type steroid, 2α-hydroxy-3α-methoxy-5α-pregnane (1), together with three known dammarane-type triterpenoid, 3β-acetyl-20S,24S-epoxy-25-hydroxydammarane (2), 20S,24S-epoxy-3α,25-dihydroxydammarane (3), and eichlerianic acid (4) have been isolated from the stem bark of Aglaia elliptica. The structure s were determined by spectroscopic methods including the 2D-NMR techniques. Compound 1-4 showed moderate cytotoxic activity against P-388 murine leukemia cells.

The in vitro anti-inflammatory activity profile of the Nerium oleander flower EtOH extract/its subextracts (n-hexane, CH 2Cl 2, EtOAc, remaining H 2O) were evaluated on LPS induced Raw 264.7 macrophages. The effects of the crude EtOH extract and its subextracts on nitric oxide (NO) production and cell viability were determined. The most active subextract was determined to be the EtOAc subextract without exerting any toxicity towards Raw 264.7 macrophages. This subextract significantly inhibited NO production of Raw 264.7 macrophages after LPS induction (62.56±1.91% at 200 µg/mL concentration). The levels of iNOS were reduced up to 67.50%. Moreover, this subextract slightly reduced the phosphorylation levels of MAP kinases (p-ERK, p-JNK, p-38). The highest inhibition was observed for ERK phosphorylation, which was inhibited by 20.53% at 200 µg/mL concentration. Through activity-guided fractionation procedures, kaempferol, kaempferol 3-O-β-glucopyranoside and chlorogenic acid were isolated as the main active components. The structures of the active compounds were determined by 2D-NMR techniques and HRMS analysis. All compounds significantly inhibited NO productions. Results of the present study supported the traditional use of N. oleander flowers to treat inflammatory complaints.

In the present work, Microsteam distillation - Solid phase microextraction (MSD-SPME) and hydrodistillation (HD) techniques were applied to obtain volatiles from Achillea sivasica, an endemic species from Turkey. GC-FID and GC/MS analysis revealed that 1,8-cineole (22.1%) and a -pinene (9.3%) were the main constituents of the hydrodistilled flower volatiles. (Z)- b -Farnesene (23.9%), decanoic acid (10.1%), b- eudesmol (8.0%), tricosane (7.3%) and hexadecanoic acid (7.2%) were the main volatiles obtained from flowers by MSD-SPME. The leaf volatiles obtained by HD contained camphor (9.0%), b -pinene (6.9%), 1,8-cineole (6.7%), a -pinene (6.7%) and a -bisabolol (6.6%) as the main constituents while the leaf volatiles obtained by MSD-SPME technique were rich in (E)-geranyl acetone (10.5%), (E)- b -ionone (10.3%), camphor (10.2%), 1,8-cineole (9.6%), longiverbenone (7.9%), b -eudesmol (7.5%), isopropyl myristate (6.7%) and epi- a -bisabolol (6.4%). The root volatiles were rich in longiverbenone (14.1%), (E)-geranyl acetone (9.3%), nonanol (12.1%) and decanol (12.5%). The enantiomeric distribution of the major volatile constituents was analyzed by using different b -cyclodextrin chiral columns. (1R)-(+)- a -Pinene, (1S)-(-)- b -pinene, (4R)-(+)-limonene, (1R,3S,5R)-(-)-trans-pinocarveol, (1S,2R,4S)-(-)-borneol, (2S)-(-)- a -bisabolol were detected as dominant enantiomers. The lipids extracted from the flower and leaf with Folch method and methylated with BF 3 reagent contained common acids: linolenic, linoleic, hexadecanoic acids. Oleic and stearic acids were detected particularly in high amount in the flower lipids

The essential oils (EOs) obtained by hydro-distillation of flowers and stems of Ageratum conyzoides L. ( Asteraceae) growing in Ivory Coast were investigated. The oils were analyzed and characterized by GC and GC–MS. Analyses of the EOs led to the identification and quantification of 48 constituents in the flower oil and 44 from the stem oil, respectively. Characterization of the EOs revealed the predominance of 6-demethoxyageratochromene or precocene I (flower: 58.8%, stem: 76.5%) and the sesquiterpene β -caryophyllene (flower: 15.2%, stem: 8.1%) . Six of the identified compounds β -copaene, hexanal, trans-cadina-1(6),4-diene, α -calacorene, caryophylla-4(12),8(13)-diene-5-β-ol and 1,10-di-epi-cubenol are reported for the first time as constituents of A. conyzoides . Comparative analysis with data from Nigeria, Pakistan, Fiji and Brazil is reported. The antibacterial activity of EOs from of A. conyzoides was tested against seven bacteria. The inhibition zones and minimum inhibitory concentration (MIC) for bacteria strains which were sensitive to A. conyzoides EOs were in the range of 6.7 to 12.7 mm and 64 to 256 μg/mL, respectively. The EOs showed moderate activity against Staphylococcus aureus and Enterococcus faecalis .

Green Coffea arabica L. seed oil (GCO) has been used as an active cosmetic ingredient in many skin care products, due to its composition and balance of fatty acids. On the other hand, while roasted coffee oil (RCO) is mainly used for imparting aroma in the food industry, there is no data available to suggest its safety in cell-based model systems. In this context, the present study aims to evaluate the chemical composition of GCO, RCO, and their correspondent polar fractions (PFs); and assess their cytotoxicity and antioxidant potential in vitro. RCO and RCO PF exhibited significantly higher amounts of phenolic compounds, when compared to both GCO and GCO PF. In the DPPH assay, after 5 min of incubation, RCO inhibited about 80% of radicals, while GCO only achieved half of this activity. Similar results were also obtained for their PFs. Upon exposure to GCO, no cytotoxic effects were observed, in fact, there were slight increments in cell proliferation. Nevertheless, cell exposure to RCO led to significant decreases in cell viability. Increases in the concentration of coffee oil PFs were associated with correspondent relevant increased cytotoxicity. Upon hydrogen peroxide-induced oxidative stress, neither GCO nor RCO treatment were effective in protecting cells.

Fractionation of methanolic extract of Satureja khuzistanica Jamzad by Sephadex LH-20 and reverse phase chromatography led to the isolation and purification of a new monoterpene flavonoid ( 1 ), as well as six previously detected flavonoid derivatives ( 2 – 6 ). The structure assignment has been performed by using 1D, 2D NMR, and high-resolution MS spectrometry. In addition, electronic circular dichroism (ECD) spectroscopy was used to reveal the absolute configuration of 1.

A new dibenzofuran derivative, 1,2,4-trimethoxydibenzofuran-3,9-diol (7), was isolated from the ethyl acetate fraction of Sorbus commixta barks, along with six known compounds, lupeol (1), betulin (2), betulinic acid (3), ursolic acid (4), b -sitosterol (5) and b -pyrufuran (6). Their structures were determined by NMR spectroscopic analysis, including of 1H and 13C NMR, 1H- 1H COSY, HSQC and HMBC spectra data. Cytotoxic activities of seven compounds were evaluated in five cancer cell lines, HEp-2, A549, MCF-7, PC-3 and SKOV-3 at the concentrations ranging from 10 to 100 m M.

Mosquitoes are vectors for many pathogens and parasites that cause human diseases including dengue, yellow fever, West Nile, chikungunya, filariasis and malaria which cause high rates of human morbidity and mortality under extreme conditions. Plants are an excellent source for mosquito control agents because they constitute rich sources of bioactive chemicals. They are also biodegradable and environment-friendly. The present study reports on the larvicidal activity of the essential oil of Seseli gummiferum. subsp. ilgazense (Apiaceae) against Aedes aegypti larvae. Essential oil showed 100 and 70% mortality at 125 and 62.6 ppm, respectively, with no mortality at 31.25 ppm. Aerial parts of S. gummiferum subsp. ilgazense were subjected to hydrodistillation to yield 0.6% oil. The essential oil was analyzed by GC-FID and GC-MS techniques. The main constituents in the oil were sabinene (28.8%), germacrene D (9.5%) and α -pinene (7.2%).

This work describes a new ent-kaurene diterpene glucoside, 7β-O-β-D-glucopyranoside-ent-kaur-16-ene, from the leaves of Xylopia excellens R.E.Fr. (Annonaceae). The compound showed high in vitro antileishmanial activity (IC 50 of 15.23 ± 0.64 µg/mL) towards promastigote forms of Leishmania amazonensis, and low cytotoxicity against J774A1 cells (SI of 1.96).

Essential oils obtained by hydrodistillation were analyzed both by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS).The main constituents found in Achillea oil were as follows: A. filipendulina Lam.: 43.8% santolina alcohol, 14.5% 1,8-cineole and 12.5% cis-chrysanthenyl acetate; A. magnifica Hiemerl ex Hub.-Mor.: 27.5% linalool, 5.8% spathulenol, 5.5% terpinen-4-ol, 4.7% α-terpineol and 4.7% β-eudesmol; A. tenuifolia Lam.: 12.4% artemisia ketone, 9.9% p-cymene, 7.1% camphor, 5.9% terpinen-4-ol, 4.7% caryophyllene oxide and 4.5% α-pinene. Furthermore, the Achillea essential oils were evaluated for antimalarial and antimicrobial activities. A. magnifica and A. filipendulina oils showed strong antimalarial activity against both chloroquine sensitive D6 (IC 50= 1.2 and 0.68 m g/mL) and chloroquine resistant W2 (IC 50= 1.1 and 0.9 m g/mL) strains of Plasmodium falciparum without any cytotoxicity to mammalian cells up to IC 50=47.6 m g/mL against Vero cells. whereas A. tenuifolia oil showed no antimalarial activity up to a concentration of 20 mg/mL. All three Achillea oils showed no antibacterial activity against human pathogenic bacteria up to a concentration of 200 m g/mL. A. tenuifolia and A. magnifica oils demonstrated mild antifungal activity against Cryptococcus neoformans (IC 50= 45, 20 and 15 m g/mL, respectively).