Records of Natural Products Articles

Normal and reversed phasechromatographic purification of the chloroform soluble fraction of the methanolic extract of Tribulus longipetalus led to the isolation of a new tyramine amide, longipetalamide (1), two new benzocoumarins, longipetalasin A (8-n-propyl-threo-1 ¢ S ,2 ¢ S -dihydroxy-5-methoxy-5a,9a-benzocoumarin; 2) and B (8-n-propyl-threo-1 ¢ S ,2 ¢ S -dihydroxy-5,10-dimethoxy-5a,9a-benzocoumarin; 3) together with 1,2,3-propantriyl trioleate (4), crotamide A (5), stigmasterol (6), (25S)-5α-furustan-22-methoxy-3β,26-diol (7), neotigogenin (8), tigogenin (9), methyl 4-hydroxyphenyl acetate (10) and 2-O-methylinositol (11). All the isolates (1-11) were characterized by using UV, IR, 1D- ( 1H and 13C), 2D-NMR (HSQC, HMBC, COSY) spectroscopy, mass spectrometry (EI-MS, HR-EI-MS, FAB-MS, HR-FAB-MS) and in comparison with the data reported in literature. The compounds 1-11 were evaluated for their enzyme inhibition studies against α-glucosidase, lipoxygenase (LOX), acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes and found that 2 and 3 were the significant inhibitors of enzyme α-glucosidase with IC 50 values 94.17 ± 0.09 and 85.65 ± 0.08 µM, respectively.

Essential oils of four ornamental species and hybrids of Nepeta: N. racemosa Lam. hybrid ‘Select’, N. sibirica L., N. subsessilis Maxim, and N.×faassenii Bergmans ex Stearn ‘Dropmore were studied for their chemical composition, larvicidal and biting deterrent activity. Water-distilled essential oils from aerial parts of Nepeta species were analyzed by gas chromatography (GC-FID) and gas chromatography mass spectrometry (GC-MS). Nepeta racemosa hybrid ‘Select’ and N. ×faassenii ‘Dropmore’ essential oils were rich in 1,8-cineole whereas N. sibirica and N. subsessilis essential oils mainly consisted of sesquiterpenes: (Z)- b -farnesene, b -bisabolene, d -cadinene or b -caryophyllene, and caryophyllene oxide. Many Nepeta species essential oils are reported to be rich in nepetalactone isomers, but essential oils from these species contained either very low or no nepetalactone content. In biting deterrent bioassays, essential oils of these Nepeta species and hybrids at 100 µg/cm 2 showed activity similar to DEET at 25 nmol/cm 2 against Aedes aegypti, whereas this activity at the concentration of 10 µg/cm 2 was lower than DEET. All the essential oils showed weak larvicidal activity and mortalities were observed only at highest dose of 125 ppm against Ae. aegypti.

Pancreatic lipase plays an important role in the digestion and absorption of fats; it has become a target of interest in the treatment of obesity. Investigations of pancreatic lipase inhibitory compounds from Cnidium officinale rhizomes have resulted in the isolation of a new phthalide derivative (1) together with ten known phthalides (2-11). Phthalide derivatives from C. officinale showed mild inhibition against pancreatic lipase with 13 - 56% inhibition at 100 μM. Structure activity relationship suggested that the double bond in the side chain of phthalide increased its inhibitory activity, whereas the addition of hydroxyl moiety to side chain reduced activity. Lineweaver-Burk plot analysis also demonstrated that compound 2 was a noncompetitive inhibitor with an IC 50 of 86.4 μM. Taken together, C. officinale and its phthalide constituents might be beneficial for the regulation of obesity through pancreatic lipase inhibition.

The essential oils and hexane extracts of four Achillea species were analyzed by GC/MS. Achillea biserrata Bieb., Achillea wilhelmsii C. Koch and Achillea biebersteinii Afan oils contained mainly 1,8-cineole (38.1-14.4%), camphor (46.6-23.6%) and borneol (11.7-2.9%, ). Achillea coarctata Poir. oil had more different composition, with its main components being viridiflorol (37.7%), α-cadinol (8.9%) and cubenol (6.1%). The hexane extracts of A. wilhelmsii, A. coarctata and A. biebersteinii had high percentages of camphor (44.7%, 16.2% and 18.0%, respectively) and 1,8-cineole (19.5%, 30.8% and 165.1%, respectively), whereas the most abundant components in A. biserrata extract were ethyl oleate (13.1%), n-nonadecane (11.3%), and n-eicosane (11.3%). Herbicidal activities of the oils and hexane, acetone and methanol extracts of four Achillea species were assessed against six weed species and germinations, root and shoot growths of weed species were significantly inhibited by both the oils and extracts. In the pest toxicity assay on Leptinotarsa decemlineata, the oils showed toxic effect against the pest. According to the present results, Achillea species could be used as alternative bio-insecticides and bio-herbicides.

Eryngium species (Apiaceae) are well known plants in ethnobotanical culture throughout world and also in Turkey. They are used as antitussive, diuretic as well as for analgesic and antiinflammatory purposes in traditional medicine. This study aimed to evaluate the antinociceptive activity of endemic Eryngium kotschyi Boiss. root extracts by bioguided fractionation. The antinociceptive activity of the extracts/fractions/compound was studied in mice using acetic acid induced writhing test and and hot plate test. The methanolic extract was sequentially partitioned with hexane, dichloromethane and water saturated n-butanol. Among the fractions, the n-BuOH fraction showed the most significant results in both hot plate test (n-butanol 18,83 ± 1 .81 s p<0,05 versus control: 8.33 ± 0.67 s) and acetic acid induced writhing test (n-butanol 19,17 ± 2,41 p<0,005 versus control 32,67 ± 2,23 ) and was chosen for further bioguided purifications by column chromatography and MPLC yielding a pure known triterpene saponin which was characterized as a derivative of A1-barrigenol, showing a moderate antinociceptive activity by hot-plate test ( 14,33 ± 0,33 s, P < 0.05 versus control). These findings contribute to the justification of the ethnobotanical use and relevance of Eryngium species. The results suggest there may be a synergy of compounds in the selected activity and support the usage of bioguided fractionation in the search for responsible compounds in plants for antinociceptive activity. Further studies are needed to elucidate the mechanism for action and the structure of compounds which might be responsible of the effect.

The volatiles from thirty six propolis samples collected from six different geographical locations in Portugal (mainland, Azores archipelago and Madeira Island) were evaluated. Populus x canadensis Moenchen leaf-buds and Cistus ladanifer L. branches essential oils were comparatively analysed. The essential oils were isolated by hydrodistillation and analysed by Gas Chromatography (GC) and Gas Chromatography-Mass Spectrometry (GC-MS). Cluster analysis based on propolis samples volatiles chemical composition defined three main clusters, not related to sample site collection. Cluster I grouped 28 samples with high relative amounts of oxygen-containing sesquiterpenes (20-77%), while cluster II grouped 7 samples rich in oxygen-containing monoterpenes (9-65%) and the only sample from cluster III was monoterpene hydrocarbons rich (26%). Although Populus x canadensis and Cistus ladanifer were associated as resin sources of Portuguese propolis, other Populus species as well as plants like Juniperus genus may contribute to the resin in specific geographical locations.

A new cytochalasan named as phomocytochalasin (1), together with five previously identified compounds, cytochalasin H, cytochalasin N, RKS-1778, dankasterone B, cyclo(L-Ile-L-Leu), were isolated from the solid fermentate of Phomopsis theicola BCRC 09F0213, an endophytic fungus isolated from the leaves of an endemic Formosan plant Litsea hypophaea Hayata . The structure of the new compound was established by spectroscopic methods, including UV, IR, HR-ESIMS, and extensive 1D- and 2D-NMR techniques. Among the isolates, cytochalasin N showed NO inhibitory activity with IC 50 values of 77.8 μM . Cytochalasin H showed the progesterone receptor (PR) antagonism with the IC 50 value of 1.42 μM.

he present study was designated to (1) characterize the essential oil from S. galatica (SGEOs) and (2) evaluate its antioxidant and enzyme inhibitory activities. Antioxidant capacity was tested different methods including free radical scavenging (DPPH, ABTS and NO), reducing power (FRAP and CUPRAC), metal chelating and phosphomolybdenum. Inhibitory activities were analyzed on acetylcholiesterase, butrylcholinesterase, α-amylase and α-glucosidase. SGEOs were chemically analyzed and identified by gas chromatography and gas chromatography/mass spectrophotometry. 23 components, representing 98.1% of SGEOs were identified. Monoterpene hydrocarbons (74.1%), especially α- (23.0%) and β-pinene (32.2%), were the main constituents in SGEOs. The main sesquiterpene hydrocarbons were β-caryophyllene (16.9%), germacrene-D (1.2%) and caryophyllene oxide (1.2%), respectively. Generally, SGEOs has shown moderate free radical, reducing power, metal chelating and enzyme inhibitory activities. These activities related to chemical profile in SGEOs. Our findings supported that the possible utility of SGEOs is a source of natural agents for food or pharmaceutical industries.

A new sesquiterpenoid named germacradiene-6 -O-(6'-O-acetyl)-β-D-glucoside (1) and a new flavonol glycoside named rhamnetin-3-O-(2′′-O- β-D-glucopyranosyl)- β-D-galactopyranoside (2), along with three known sesquiterpenoids dictamnol (3), radicol (4), germacradiene glucoside (5); three phenylpropanoids 4-methoxy-2-(3-methyloxiranyl)-phenyl 2-methylbutanoate (6), 4-methoxy-2-(3-methyloxiranyl)-phenyl angelate (7), thellungianin E (8); and a flavonol glycoside platanoside (9) were isolated from the aerial parts of Pimpinella tragium Vill . subsp. lithophila (Schischkin) Tutin. Their structures were elucidated by detailed analyses of 1D and 2D NMR, UV, IR and HR-ESI-MS data.

The n-hexane extracted volatile fraction of high potency Cannabis sativa L (Cannabaceae) . was assessed in vitro for antifungal, antibacterial and antileishmanial activities. The oil exhibited selective albeit modest, antifungal activity against Cryptococcus neoformans with an IC 50 value of 33.1 µg/mL. Biologically-guided fractionation of the volatile fraction resulted in the isolation of three major compounds (1-3) using various chromatographic techniques. The chemical structures of the isolated compounds were identified as α-humulene (1), b -caryophyllene (2) and caryophyllene oxide (3) using GC/FID, GC/MS, 1D- and 2D-NMR analyses, respectively. Compound 1 showed potent and selective antifungal activity against Cryptococcus neoformans with IC 50 and MIC values of 1.18 m g/mL and 5.0 m g/mL respectively. Whereas compound 2 showed weak activity (IC 50 19.4 µg/mL), while compound 3 was inactive against C. neoformans.

The new pyrrolizidine alkaloid (PA) 3΄-O-acetylechinatine N-oxide (7), along with two more known PAs (5, 6), two known flavonoids (3, 4), one known alkannin (1), two known triterpenoids, one known sterol, and allantoin (2) were isolated from the aerial parts of Onosma kaheirei. In addition, the retention indeces of the reduced PAs 6 and 7 were determined in a DB-5 WCOT column, to aid their detection by GC/MS in the future.

Chemical composition of the essential oil (EO) (analysed by GC and GC/MS), the types and distribution of trichomes, and pollen morphology were investigated in Stachys iva Griseb. and S. horvaticii Micevski (Lamiaceae) growing in Republic of Macedonia. The essential oil of Stachys iva was characterized by a high concentration of oxygenated sesquiterpene (43.8%) of which caryophyllene oxide (34.2%) and spathulenol (8.3%) being the principal compounds, while hexadecanoic acid being a major component in the both S. horvaticii oil with percentages of 25.7% in the oil from locality Babuna River Gorge and 28.4 % in the oil from locality Rajec River Gorge. Non-glandular trichomes, and two type of capitate trichomes (type 1 composed of one basal epidermal cell, one stem cell and a unicellular head cell with subcuticular space; type 2 composed of one elevated basal epidermal cell, one stem cells, and a head composed of four, sometimes two small cells) were observed on leaves, calyx and the stem.

The aim of this study was the term of the climate influence on essential oil and aroma components of six Eleutherococcus species [E. senticosus (Rupr. & Maxim.) Maxim., E. setchuensis (Harms) Nakai, E. sessiliflorus (Rupr. & Maxim.) S. Y. Hu, E. gracilistylus (W. W. Smith) S. Y. Hu, E. henryi Oliv., E. divaricatus (Siebold & Zucc.) S. Y. Hu ] cultivated in Poland. The hydrodistilled volatiles of the samples were ranged from 0.2% to 0.4%. The components of the determined volatiles were analyzed by GC/MS/MS. Thirty of the same compounds were present in all samples. Major components of the samples were (E,E)-farnesol (43.6-6.9%), (E,Z)-farnesol (7.2-0.7%), (Z,E)-farnesol (1.4-0.1%), tetradecanoic acid (9.91-2.08%), and pentadecanoic acid (12.8-3.5%). Highest (E,E)-farnesol content (43.6%) was determined in the roots of E. divaricatus. This compound may be considered as chemical marker of the species. This is the first time, when the analysis of volatiles in the roots of Eleutherococcus spp. cultivated in Poland was performed. This study provides a platform for further investigation for the isolation and pharmacological activity of active principles.

The present study reports the chemical composition on the essential oil of fresh flowering aerial parts and headspace (HS) volatiles obtained from fresh stem and flower of Chaerophyllum aureum L. For hydrodistilled oil, 45 components were identified representing 99.1 % of the total, while 23 components, representing 99.9 % of total HS stem volatiles and 25 components, representing 99.9 % of total HS flower volatiles were found using GC and GC/MS method. The main constituents of C. aureum hydrodistilled oil, stem and flower HS volatiles were: sabinene (40.8 %, 53.5 %, 58.5 %) and terpinolene (19.1 %, 23.8 %, 11.2 %) respectively. The results of antibacterial assay showed that the essential oil was not active at concentration of 3 and 5 mg per disk. Also, the examined oil was almost inactive in applied antioxidant assays.

The flowers and vegetative parts essential oils of Anvillea garcinii were analyzed by GC-FID and GC-MS using polar and nonpolar columns which led to the identification of total 140 compounds from both oils, among which 130 compounds were identified for the first time in the genus Anvillea. In the flowers oil 126 compounds were identified, whereas 119 compounds were identified in the vegetative parts oil of A. garcinii representing 95.7% and 94.9% of the total oil composition, respectively. The major components in the flowers oil were bornyl acetate (33.7%), cis-nerolidol (7.3%) and camphene (6.1%). In contrast, the major compounds in the vegetative parts oil were cis-nerolidol (16.0%), terpine n-4-ol (10.4%) and cabreuva oxide B (6.4%).

The essential oils from the leaves and flowers of Cantinoa stricta (Benth.) Harley & J.F.B. Pastore (Lamiaceae) were obtained by hydrodistillation and analyzed by GC/FID and GC/ MS. The major components of both oils were caryophyllene oxide (leaf – 31.6%; flower – 21.7%) and cis-pinane (leaf – 15.4%; flower – 9.7%). The flower oil also contained significant amounts of a -pinene (9.4%) and b -pinene (9.1%). The oils were tested in vitro against U251 (glioma), UACC-62 (melanoma), MCF-7 (breast), NCI-H460 (lung), PC-3 (prostate), K-562 (leukemia) human cancer cell lines and against HaCat (no cancer cell), using the sulforhodamine B method. Both oils showed antiproliferative activity against all tested cells lines (TGI < 50 m g/mL), with exception of K562 cells. The highest activity was observed against MCF-7 cell lines (TGI = 4.54-10.36 m g/mL).

Chemical composition of yarrow (Achillea millefolium L. ssp. millefolium ) essential oils was presented in the study. Plant material was collected at four populations where two forms, white ( f. millefolium ) and pink ( f. rosea) of A. millefolium L. are growing together (in Lithuania). The essential oils of different plant organs (inflorescences and leaves) were obtained by hydro-distillation and analyzed by GC and GC/MS. The application of PCA and AHC grouped the sixteen oils into seven segments, that allowed to distinguish four new chemical profiles of yarrow essential oils. For the first time, atypical chemotypes with predominant cis-chrysanthenol (27.3%), selin-11-en-4 a -ol (24.0%), viridiflorol (13.7%) and 10-epi-γ-eudesmol (10.0-15.6%, three samples) have been described for yarrow leaf oils.