Records of Natural Products Articles

Stachys genus is one of the largest genera of the Labiatae (Lamiaceae) family and is widely distributed across Europe and East Asia, as well as in America. In this study the essential oil composition and consumption pattern of Stachys species as food are discussed. A survey of the literature found that the genus was consumed primarily as teas and that this was due to their essential oil and phenolics contents. Some species of the genus are also consumed in Europe and China as a carbohydrate source.

Two new lycoctonine type C19-diterpenoid alkaloids, swatinine-A (1), and swatinine-B (2), along with four known C19-diterpenoid alkaloids, foresticine (3), neoline (4), delvestine (5), and chasmanine (6), were isolated from the aerial parts of the Aconitum laeve Royle. The structures of compounds 1 and 2 were deduced on the basis of spectroscopic techniques (EI-MS, HREI-MS, 1H NMR, 13C NMR, HMQC, and HMBC). Biological activities like inhibition of the multifunctional copper-containing enzyme tyrosinase, anti-oxidant and anti-inflammatory have also been carried out for all the compounds and reported herein. The structure-activity relationships for the inhibition of the enzyme tyrosinase by the compounds have been discussed.

 Ethnobotanical surveys revealed that Daphne oleoidesSchreber has been used against rheumatic pain and for wound healing in Turkish folk medicine. The aim of the present study is to verify the folkloric assertion of D. oleoides ssp. oleoides (DOO) by bioassay-guided fractionation procedures leading to determination of the active component(s) and to elucidate the activity mechanisms of the isolated compounds. The wound healing activity of the methanol extract, its subextracts, fractions and isolates was evaluated by using two different in vivo wound healing experimental techniques . Anti-inflammatory and antioxidant activities of the test materials were also evaluated. For the determination of the activity mechanisms, the isolated compounds were screened for hyaluronidase, collagenase and elastase enzyme inhibitory activities. The methanolic extract of DOO was found to possess potent wound healing activity. This extract was then subjected to successive solvent extractions with n-hexane, dichloromethane, ethyl acetate (EtOAc) and n-butanol. EtOAc subextract yielded three compounds, quercetin 3-O-glucoside, triumbellin and rutarensin by using chromatographic separation techniques. The experimental study revealed that D. oleoides subsp. oleoides methanolic extract possesses significant wound healing effect and quercetin 3-O-glucoside was determined as the active component responsible from the activity.

GC-MS analysis of the essential oils from aerial parts of Thymus migricus Klokov & Des.-Shost, Thymus fallax Fisch. & Mey. and Thymus pubescens Boiss. & Kotschy ex Celak var. pubescens resulted in the identification of 26, 35 and 53 constituents, respectively. The major components in the essential oil of T. migricus were found to be α-terpineol (30.6%), thymol (20.7%) and α-terpinyl acetate (14.9%) while in the essentiol oil of T. fallaxcis-carveol (29.6%) and α-terpineol (10.8%). Carvacrol was a dominant compound with a percentage 66.1% of the essential oil of T. pubescens var. pubescens. The data obtained indicate that the essential oils of Thymus species generally exhibit some bacteriostatic activity. The antioxidant activity of the tested essential oils were found to be slightly lower than butylatedhydroxyanisole (BHA).

T wo new tri terpenoids namely, 3α - hydroxyferna-7, 9(11),22-trien-12-one (1) and 3α - acetoxyferna-7, 9(11)-dien-22-ol (2) along with two known compounds 3α,16α-dihydroxyferna-7,9(11)-dien-12-one (3) and 3α,16α-dihydroxyfern a -8-en-11-one (4) were isolated from Lonicera quinquelocularis . Their structures were elucidated by chemical and modern spectroscopic techniques. All the compounds showed good antioxidant activities in the DPPH radical scavenging assay.

the potential of the skin of anuran amphibians as a new source of bioactive peptides was investigated . For this purpose, the study collected data in the mid-eastern region of Argentina. Two anuran amphibian species were studied which belong to the Hylidae and Leptodactylidae families, Leptodatylus latrans (Ll) and Hypsiboas pulchellus (Hp). Two methods for the extraction of bioactive components were compared in their effectiveness: solvent extraction (SE) and transcutaneous amphibian stimulation (TAS). Two different approaches were used to study the extracts: i) the direct analysis of the complete samples by MALDI-TOF-MS, and ii) the characterization of bioactive fractions obtained by HPLC and analyzed by MS. The results show that not only the composition of the samples obtained by SE and TAS is different but also their antimicrobial activity. In this sense, only the extracts obtained from Ll and Hp by SE inhibited the growth of Mycobacterium tuberculosis H37Rv. The inhibitory activity of the extracts against the butyrylcholinesterase enzyme (BChE) was also investigated. Samples of Ll showed low percentages of inhibition whereas in Hp samples, the inhibition was moderate (40 -44%). The results suggest that the inhibitory activity of Hp is related to the presence of low molecular weight compounds.

 Volatile oil composition and antiproliferative activity of Laurus nobilis L. (Lauraceae) fruits and leaves grown in Jordan were investigated. GC-MS analysis of the essential oil of the fruits resulted in the identification of 45 components representing 99.7 % of the total oil content, while the leaf essential oil yielded 37 compounds representing 93.7% of the total oil content. Oxygenated monoterpene 1,8-cineole was the main component in the fruit and leaf oils. Using sulphorhodamine B assay; the crude ethanol fraction, among other solvent extracts, showed strong antiproliferative activity for both leaves and fruits, nevertheless, the fruits were more potent against both breast cancer cell models (MCF7 and T47D). At IC 50 values ; the mechanism of apoptosis was nevertheless different: where L. nobilis fruit proapoptotic efficacy was not regulated by either p53 or p21, L. nobilis leaf extract components enhanced the p53 levels substantially. In both extracts, apoptosis was not caspase-8 or Fas Ligand and sFas (Fas/APO-1) dependent. Our studies highlight L. nobilis as a potential natural agent for breast cancer therapy. Compared with non induced basal cells, both L. nobilis fruits and leaves induced a significant enrichment in the cytoplasmic mono- and oligonucleosomes after assumed induction of programmed MCF7 cell death.

The volatile constituents of different plant parts and populations of Malabaila aurea Boiss. from Montenegro were obtained by simultaneous distillation-extraction and analyzed by GC-FID and GC-MS. A total of 12 samples were examined and 45 compounds were identified. The volatile content of different M. aurea populations was very similar, while the volatile fractions obtained from different plant parts showed significant qualitative and quantitative differences. The most abundant compounds found in stems & leaves were apiole (51.0-56.3%), myristicin (16.3-25.4%), and falcarinol (4.1-10.7%). The roots showed the same major components, but with different relative abundances: 30.9-49.1% of apiole, 12.9-34.7% of falcarinol, and 9.9-31.1% of myristicin. The volatile constituents of fruits & flowers were remarkably different, containing up to 71.2-80.5% octyl butyrate, 11.4-18.0% octanol, and 2.7-6.8% octyl hexanoate. The results were discussed as possible indication of relatedness of Malabaila aurea and Pastinacasativa (parsnip) .

Five eremophilane sesquiterpenoids were isolated from the rhizomes of Ligularia fischeri grown in Henan province of China and identified as 3α-Tigloyloxyeremophila-9,11-dien-8-one (3), Isopetasan (4), Neopetasan (5), Isopetasol(6) and Petasol (7), by spectroscopic methods. Petasin (1) previously isolated was analyzed to determine its absolute configuration by X-ray single crystal diffraction. Five petasin derivatives including three new compounds (2a, 6a and 6b) were synthesized. 12 eremophilane sesquiterpenoids including the derivatives except for 4 (minor amount) were assessed against human neuroblastoma (SKN-SH) by the SRB method. 1 was also tested on inhibiting prostate carcinoma (Bc3) cell lines. The results showed 1 has the strong inhibitory activity against SKN-SH and Bc3 cell lines and other compounds with α-isopropylidene group also have the strong activity against the human neuroblastoma (SKN-SH). The above results indicated the α - isopropylidene group might be the active center against pulmonary carcinoma (SKN-SH) in the same eremophilane-type skeleton. Petasins may be interesting for their good bioactivities.

The fatty acid (FA) compositions of 14 wild wood-decaying basidiomycete species (Bjerkandera adusta, Daedaleopsis septentrionalis, Dichomitus squalens, Inonotus hispidus, I.radiatus, Irpex lacteus, Fomitopsis cajanderi, F.pinicola, F. rosea, Gloeophyllum protractum, Lenzites betulina, Phellinus pini, Trametes gibbosa, T. ochracea) growing in permafrost conditions in Katanga region (Russian Federation) were investigated using GC-MS. Generally, C18:2ω 6 (linoleic acid), C18:1 ω 9 (oleic acid), C16:0 (palmitic acid) and C20:0 (arachinic acid) were found to be the major FA in fungal species. Data about chemical components of Daedaleopsis septentrionalis , Fomitopsis cajanderi and Gloeophyllum protractum were obtained at the first time. Increased level of degree of FA unsaturation was probably a result of extreme environmental conditions.

The effects of baking practices on the fatty acid and bioactivity of edible mushrooms; namely, Lactarius delicious and Ramaria flava, naturally growing in Anatolia were investigated. Each mushroom species was divided into two parts and one of the parts was baked. Both baked and unbaked materials were extracted with hexane and methanol, successively. The fatty acid contents of baked and unbaked extracts of both species were carried out by GC and GC-MS analytical techniques. In the unbaked extracts palmitic acid (9.7-14.43%), stearic acid (41.41-6.68%), oleic acid (25.94-47.12%) and linoleic acid (22.85-9.78%) were identified as major fatty acids, respectively. In the baked extracts, however, palmitic acid (7.92-19.12%), stearic acid (49.94-6.23%), oleic acid (18.07-45.13%) and linoleic acid (23.36-9.25%) were identified as major fatty acids, as well. The antioxidative effect of the extracts of baked and unbaked mushroom species was also determined by using four complimentary assays. In addition, the extracts and the major fatty acids were also evaluated for anticholinesterase activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) which are the chief enzymes of Alzheimer’s disease. The baked methanol extract of R. flava showed the highest activity in DPPH scavenging, ABTS scavenging and BChE assays, while the unbaked hexane extract of R. flava exhibited the best lipid peroxidation inhibition activity. In conclusion, baking proved to have influence in nutritional values and bioactivity properties of L. delicious and R. flava. The nutrient concentration and bioactivities of L. delicious were decreased when baked; however, baked R. flavaproved to have higher nutrient concentrations and higher bioactivities than unbaked samples.

Boehmenan (1) is a lignan which has two feruloyl moieties at C-9 and C-9"' respectively. The structural characterization of (+)-boehmenan was confirmed by 1H-NMR, 13C NMR and HRESIMS as well as by direct comparison with the literature. CD measurements established a 7S' , 8R' configuration. Cytotoxicity evaluation showed that boehmenan is moderately active against the T47D cell line with IC 50 13.7 m g/mL and shows weak activity against the HeLa cancer cell line with IC 50 93.5 m g/mL. Boehmenan is also non-cytotoxic to the Vero cell line. From this study, boehmenan X and erythro-carolignan E were also obtained.

The total alkaloidal fraction of Lobelia laxiflora L. roots was tested for cholinesterase inhibiting activity using spectrophotometric method. The IC 50 value of the alkaloidal fraction recorded was close to that of eserine ( 286.3 µg/mL and 270 µg/mL, respectively) . This biologically active alkaloidal fraction was subjected to a phytochemical study to isolate and identify its major constituents. Two piperidine alkaloids, N-methyl-2(2 ' -methoxybutyl),6(2 '' -hydroxybutyl)- Δ 3 -piperidine (1) and N-methyl- 2(2 ' -hydroxybutyl),6(2 '' -hydroxybutyl)- Δ 3 -piperidine (2), were isolated. The structures of the two compounds were established based on their spectral data, including MS, 1H- and 13C-NMR, COSY, HMQC and HMBC spectral experiments. Compound (1) is a new natural compound while compound (2) was previously isolated from the aerial parts of the same plant.

Mutellina purpurea L. belongs to Apiaceae family and is known as Alpin lovage considered as a forage for animals nutrition because of the presence of sufficient concentration of minerals like calcium and potassium. The chemical composition of the essential oil obtained by hydrodistillation in a Clevenger apparatus and aroma of inflorescences of Mutellina purpurea (Poir.) Thell. was analyzed by GC/MS and GC-FID. Sabinene (19.2%), a -pinene (12,6%), (E)-sesquisabinene hydrate (9.0%), myrcene (7.8%), (Z)-sesquisabinene hydrate (7.5%) and a -bisabolol (6.7%) dominated in the essential oil obtained by hydrodistillation. S tatic headspace technique gave sabinene (23.0%), p-cresol (17.4%), a - pinene (17.0%) and myrcene (10.9%) as a major constituents. Antioxidant activity of the oil was evaluated by ABTS assay.