Records of Natural Products Articles

This review focuses on inhibitory effect of Satureja species on certain organism types. For this purpose; Web of Science, PubMed, Scopus, and Google Scholar databases were searched up to 24 th December 2013. The search term was only “Satureja” without narrowing or limiting search elements. Once all reports obtained from databases (total number is about 610), author keywords and keywords plus sections, in addition to their full texts, were carefully checked out to find the active plant species related to the topic of this review. By this way, errors based on overlooks were eliminated. Forty-three reports, published between 1991-2013, were reviewed for the ir insecticidal, larvicidal, acaricidal, antiviral, anti-leishmanial, anti-protozoal, trypanocidal, nematicidal, ovicidal, molluscicidal, anti-helmintic, amoebicidal activities.

Terpenes confer advantage in plant protection against abiotic stresses such as heat and drought and biotic stresses such as herbivore and pathogen attack. We conducted a screening of leaf mono- and sesquiterpene concentrations in 75 common woody plant species in the rainforest of Danum Valley (Borneo). Terpene compounds were found in 73 out of the 75 analysed species. Similar or lower proportions have been reported in other parts of the world. To our knowledge, this study reports for the first time the foliar concentration of mono- and/or sesquiterpene for 71 species and 39 genera not previously analyzed. Altogether 80 terpene compounds were determined across the species, and out of these only linalool oxide and (E)- g -bisabolene had phylogenetic signal. A significant negative relationship between leaf monoterpene concentration and leaf length was observed, but leaf mono- and sesquitepene concentration were not related to any other leaf morphological trait nor to leaf elemental composition. Functions such as temperature protection, radiation protection or signaling and communication could underlie the high frequency of terpene-containing species of this tropical ecosystem which has multiple and very diverse interactions among multiple species.

The seasonal variation in the chemical composition and chemosystematics of the leaves of Betula pendula Roth. ,B. pubescens Ehrh., B. humilis Schrank and B. nana L. (Betulaceae), growing naturally in Estonia, and in B. pendula buds was studied. Polyphenols were analyzed by HPLC and HPLC-MS/MS. Hyperoside (423-3724 µg/g), myricetin glucuronide (106-1696 µg/g), quercetin glucuronide (206-1435 µg/g), myricetin glucoside (89-1197 µg/g), quercitrin (53-578 µg/g), and kaempferol glucuronide (77-342 µg/g) were found to be the main flavonoids in the birch leaves studied. The content of flavonoids in buds was lower than in leaves. The moderate correlations between the contents of the main polyphenols in the compared birch species were determined: B. pendula showed correlations with B. pubescens and with B. humilis. The seasonal variation of polyphenols was specific for each birch species, and no general tendency was observed. The presence of coumaric acid O-hexoside is not typical to B. nana and the content of some polyphenols can indicate the collecting time of plant material.

Astragalus species are medicinal plants which produce valuable secondary metabolites, especially cycloartane-type glycosides. In this study, stem and leaf explants of Astragalus trojanus were subjected to different plant growth regulators, environmental conditions and media compositionsto identify their callus responses. Stem and leaf explants were cultured in Murashige and Skoog (MS) and woody plant (WPM) media supplemented with different concentrations of kinetin, naphthalene acetic acid, 2,4-dichlorophenoxyacetic acid, thidiazurone and indole acetic acid under two light intensities (1000 and 4000 lux) and also in dark conditions. Both MS and WPM media triggered callus regeneration. Although, callus regeneration was observed on both stem and leaf explants, callus biomass accumulation on stem explants were higher. Addition of 100 μg/L selenium and doubled concentration of WPM vitamins enhanced callus biomass on stem explants under dark conditions. Stem explants also regenerated shoots at high frequencies (up to 93%), especially in kinetin added media. Astragaloside IV and cycloastragenol accumulation efficiencies were determined in calli tissues. The highest astragaloside IV production (3.5 µg/mg) was found in callus tissue regenerated from stem explants in D1 medium, whereas the highest cycloastragenol accumulation (4.8 µg/mg) was detected in callus tissue regenerated from stem explants in N2 medium.

This study evaluated the chemical composition, antioxidant and antimicrobial activities of the essential oils of twelve Ocimum basilicum L. cultivars grown in Serbia. The essential oils were obtained by hydrodistillation and analyzed by gas chromatography-flame ionization detection and GC-mass spectrometry. The oil yields ranged from 0.65 to 1.90 %. A total of 75 compounds were identified as constituents of analyzed essential oils. GC/MS analyses revealed that a majority of the examined basil cultivars belonged to the “linalool chemotype”. The results of the DPPH assay showed a very high antioxidant capacity of the basil oils, which was especially high for Blue Spice cultivar (IC 50 = 0.03 m g/mL). Significant antimicrobial activity was shown for all the tested oils. Essential oil of Compact cultivar was the most active against the bacterium Micrococcus flavus,with an MIC value of 0.009 m g/mL while Osmin cultivar exhibited the strongest antifungal activity with MIC values ranging from 0.08-1.07 m g/mL . All the examined essential oils showed a 10- to 100-fold greater ability to inhibit fungal growth compared to commercial antifungal agents.

A new aconitine-type norditerpenoid alkaloid, kohatenine (1) [10β-hydroxy-1α,8β,16β-trimethoxy-6α,14α-diacetyl-N-ethyl aconitane], along with four known alkaloids, condelphine (2), talatisamine (3), peregrine (4), and 14-O-acetyltalatisamine (5), was isolated from the aerial parts of Delphinium kohatense Munz. The structure of the new compound was deduced on the basis of combined MS (EI and FAB) and NMR (1D and 2D) spectroscopic techniques. The known compounds were confirmed by comparison of the physical and spectroscopic data with those reported in literature.

The n-hexane (HE), dichloromethane (DC), methanol (ME), ethanol 70% (ET), and methanol with Soxlhet apparatus (MS) extracts of Stachys lavandulifolia aerial parts were screened for their potential tyrosinase, acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activity. ET and MS inhibited tyrosinase with IC 50 values of 33.4 and 42.8 m g/mL, respectively. The phytochemical investigation of these extracts resulted in the isolation of the known compounds monomelittoside (1), melittoside (2), 5-allosyloxy-aucubin (3), acteoside (4) and arbutin (5). The HE extract, characterized by germacrene D, b -pinene, b -myrcene, and trans-caryophyllene as main constituents, showed the highest AChE inhibitory activity with an IC 50 value of 13.7 m g/mL while DC extract was the most active against BChE (IC 50 value of 143.9 m g/mL). The diterpene stachysolone (6) was isolated from this extract. The antioxidant properties were also investigated by four in vitro methods (DPPH, ABTS, FRAP and b -carotene bleaching tests).

In the course of screening program of Saudi plants for their potential biological activity, the methanolic extract of Solanum glabratum Dunal var. sepicula as well as its different fractions were tested for its possible cytoxicity in prostate cancer (PC3) and colon cancer (HT29) cell lines using the MTT assay. In the present study, three spirostan saponins and one flavonoid glycoside were isolated from the active n-butanol fraction through a bio-guided fractionation approach. Two new saponin glycosides were identified as 23-β-D-glucopyranosyl (23S, 25R)-spirost-5-en-3, 23 diol 3-O-α-L-rhamnopyranosyl-(1→2)-O-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranoside (2) and (25R)-spirost-5-en-3-ol 3-O-α-L-rhamnopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→3)]-β-D-galactopyranoside (3). In addition, two known compounds were also isolated and identified as isorhamnetin-3-O-α-L-rhamnopyranosyl (1→6) β-D-glucopyranoside (1) and (23S, 25R)-spirost-5-en-3, 23 diol 3-O-α-L-rhamnopyranosyl-(1→2)-O-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranoside (4). The structures of the isolated compounds were elucidated based on their MS, one dimensional and extensive two dimensional NMR spectral data. Among the isolated metabolites, compound 3 showed the highest cytotoxic activity in both PC3 and HT29 cell lines with an IC 50 values of 14.8 and 19.5 m g/mL, respectively.

The aim of the present study was to determine the chemical structures of the isolated compounds, the essential oil and fatty acid compositions of Mentha longifolia subsp. noeana with their biological activities. Ursolic acid (1), u vaol (2), stigmast-5-ene-3 b -yl formate (3), stigmast-5-en-3-one (4), b -sitosterol (5), bis(2-ethylhexyl) benzene-1,2-dicarboxylate (6),hexacosyl (E)-ferulate (7) and 5-hydroxy-6,7,3',4'-tetramethoxy flavone (8) were obtained from the aerial parts. The compounds (2-4, 6, 7) were isolated for the first time from a Mentha species. Palmitic acid (40.8%) was the major component of the non-polar fraction obtained from the petroleum ether extract. Pulegone (32.3%) was the main constituent of the essential oil which exhibited strong butyrylcholinesterase inhibitory activity (77.36 ± 0.29%), moderate antimicrobial activity against Escherichia coli,Staphylococcus aureus, and Candida albicans. The methanol extract showed 80% inhibition of lipid peroxidation, and the acetone extract possessed moderate DPPH free radical scavenging activity (60% inhibition) at 100 m g/mL.

This paper focused on the assessment of fatty acid composition and antioxidant properties of ten Cephalaria (C. aytachii, C. taurica, C. tuteliana, C. procera, C. speciosa, C. tchihatchewii, C. hirsuta, C. elazigensisvar. elazigensis,C. anatolica and C. aristata) species.

The principal fatty acids in all species were oleic acid (10.28-31.65%), linoleic acid (17.81–37.67%) and palmitic acid (10.54–23.81%). L inolenic acid was also the most abundant fatty acid component in C. tuteliana (24.42%) and in C. speciosa (36.65%) . Invitro antioxidant capacity of the hexane extracts of ten Cephalaria species was investigated by CUPRAC and DPPH methods. Total phenolic content of hexane extracts was also examined. The results showed that all species of Cephalaria have antioxidant properties with the highest trolox equivalent antioxidant capacity (1.005 ± 0.13 mmol trolox equivalent per gram extact) in C. aristata and the highest radical scavenging activity (IC 50 value 3.768 ± 0.67 mg/mL) in C. tchihatchewii . It was found that reducing power of C. aristata and radical scavenging potential of C. tchihatchewii were mainly due to highest phenolic contents of these species (2.907 ± 0.146 and 3.037 ± 0.156 mg gallic acid equivalent per gram extract, respectively). These findings suggest that the Cephalaria species might be used as a potential source of unsaturated fatty acids as well as phenolic constituents possessing antioxidant activity in food, cosmetics and pharmaceutical industries

In this present study, crude oil, fatty acid and mineral compositions of wheat (Triticum sp. L.), barley (Hordeum vulgare L.), triticale (Triticosecale Wittm. ex A. Camus.), rye (Secale cereale L.), and oat (Avena sativaL.) cultivars, respectively, from Turkey were investigated. Both the distribution of saturated fatty acids (SFA) and unsaturated fatty acids (UFA), and the mineral contents of evaluated cereals were reported. Fatty acid compositions and mineral contents were determined by gas chromatography/mass spectroscopy (GC/MS) and inductively coupled plasma optical emission spectroscopy (ICP-OES) techniques, respectively. The highest crude oil content was found in oat [cv. Seydisehir; 5.35%], whereas the lowest crude oil was in triticale [cv. Aslım-95; 1.19 %]. The results showed that the contents of total UFA in the different cultivars varied between 77.1 - 81.5 %. The major components of the cereal oils were determined as oleic and linoleic acid, respectively. The total macro-, micro- element, and heavy metal contents varied between 8638 - 16108 ppm, 113-180 ppm and 1.8 - 6.9 ppm, respectively. As a conclusion, there were significant (p < 0.01) differences between the cereal cultivars in view of their crude oil contents, fatty acid and mineral compositions of the investigated samples from Turkey.

Dorystoechas hastata Boiss. and Heldr. Ex Benthamis a monotypic plant endemic to Antalya province of Turkey. The chemical compositions of the water distilled essential oil of D. hastata different parts were investigated by GC/MS, which cultivated in Konya, Turkey. Three major compounds were identified from the aerial parts of D. hastata. Guaiol was the main component with 26.5 % of the branch essential oil. The leaf essential oil contained20.6 % 1,8-cineole, and the aerial parts contained15.0% borneol, respectively. Additionally, D. hastatacultivated samples were investigated for their macro (P, K, Ca, Mg, Na), micro (Fe, B, Mn, Zn, Cu) and heavy metal (Pb, Cd, Ni, Cr, Co) contents. The phosphorus (P) contents of D. hastata leaf, branch and the aerial parts were found as 3164, 2441 and 1852 ppm, respectively. Also, the amino acid compositions of different parts of D. hastata were investigated by HPLC. Major component of proteins in three different part of the plant was identified as proline. The highest proline content of D. hastata was found, however in the branch as 47.1 mg/100 g. As a conclusion, wihin this present study detailed chemical content of the cultivated D. hastata was investigated for the first time respective to its various parts.

Phytochemical investigation on the stem of Euphorbia polyacantha Boiss. (Euphorbiaceae) afforded a new anthraquinone named as 1, 8-dihydroxy -3- (hydroxyl methyl) -5- methoxy anthracene- 9,10- dione (1) along with three known compounds, aloe emodin (2) , 3, 4, 3 ¢ –tri-O-methyl ellagic acid (3), and 3,3 ¢ ,4, 4 ¢ - tetra-O-methyl ellagic acid (4). Their structures were determined on the basis of IR, 1D- and 2D- NMR spectroscopy and mass spectrometry analysis. The effect of isolated compounds on oxidative burst of neutrophils and T-cell proliferation response was studied. Compounds 3 and 1 displayed strong oxidative burst inhibitory activity with IC 50 2 ± 0 and 3.5 ± 1.1 µg/mL respectively, whereas they moderately inhibited the T-cell proliferation with IC 50 28.5 ± 1.8 and 22.5 ± 2.0 µg/mL respectively. Compound 2 was relatively inactive with IC 50 43.2 μg/mL in oxidative burst and >50 μg/mL in case of T-cell proliferation. This is the first report on the phytochemical profile and biological activity of E. polyacantha.

Headspace volatile analysis has been used for volatiles profiling in leaves of 4 Magnolia species with a total of 75 compounds were identified. Monterpene hydrocarbons dominated the volatile blend of M. calophylla (86%), M. acuminata (78%), M. virginiana (70%) and M. grandiflora (47%) with b -pinene and b -ocimene occurring in the largest amounts, whereas sesquiterpenes were the most abundant compounds in M. grandiflora (39%). High levels of oxygenated compounds were only found in M. virginiana volatile blend (11.4%) with 2-phenylethyl alcohol as major component. Hierarchical cluster analysis performed on volatiles content revealed the close relationship between M. acuminata and M. calophylla.

The different extracts of the aerial parts of Teucrium barbeyanum Aschers. were investigated for the chemical constituents and antioxidant activities. The chemical investigation of the plant led to the isolation of eleven known compounds through column chromatography in which nine were flavonoids and the other two were simple phenolic compounds. The compounds were characterized using NMR techniques ( 1H, 13C, DEPT-135 and 90, COSY, HMQC, HMBC and NOESY), UV spectroscopy and EI/ESI spectrometry. The isolated compounds were identified as 5-hydroxy-3,6,7,4′-tetramethoxyflavone (1), salvigenin (2), 5-hydroxy-6,7,3′,4′-tetramethoxyflavone (3), chrysosplenetin (4), cirsilineol (5), cirsimaritin (6), cirsiliol (7), apigenin (8) and luteolin (9),  in addition to methyl caffeate (10) and  4-hydroxybenzoic acid (11).  The antioxidant activit of the extracts was evaluated using 2,2-Diphenyl,1-picrylhydrazyl (DPPH), 2,2′-Azino-bis(3-ethylbenzothiazoline 6 sulfonic acid) diammonium salt  (ABTS) and ferric reducing antioxidant power (FRAP) methods. Ethyl acetate and butanol extracts showed comparable antioxidant activity to known antioxidants; trolox and ascorbic acid and the highest total phenolic and flavonoid contents. The active components were extracted efficiently in 70% aqueous methanol after defatting procedure. This is the first time the aforementioned compounds are isolated from this plant, and there has been no previous report on the biological studies on this species.

One flavonoid, one ursane type triterpene, and two seco-iridoids were isolated from the leaves of Olea ferruginea Royle. The compounds were screened against TNALP and CIALP enzymes for their in vitro alkaline phosphatase inhibitory studies and HeLa cancer cell lines to measure their anticancer potential. Compound 1 showed the highest activity of 89.5 ± 1.5 nM against CIALP enzyme. All the compounds showed little activity against TNALP enzyme which shows the specificity of these compounds for CIALP enzyme only. Compounds 1, 3 , and 4 exhibited anticancer activity comparable to the reference drug vincristine (VNCT). All the compounds showed minimum toxicity against vero cells at 10 μM concentration.