Records of Natural Products Articles

Dichloromethane extract of Nepeta obtusicrena Boiss. Et Kotschy Ex Hedge afforded two novel terpenoids, a diterpenoid and a triterpenoid in addition to two known triterpenoids, oleanolic acid and ursolic acid. Purification of the diterpenoid was carried out by HPLC, and its structure was elucidated as 14α-acetoxy-6-oxo-abieta-7-ene, and structure of the triterpenoid was elucidated as 2α,3β,19α,24-tetrahydroxy-11-oxo-olean-12-ene. Both of the novel terpenes were obtained from nature for the first time and named as obtusicrenone and nemrutolone, respectively. Anticholinesterase (anti-Alzheimer) and antioxidant activities [DPPH free radical scavenging activity, ABTS cation radical scavenging activity, lipid peroxidation inhibitory activity, CUPRAC (Cupric Reducing Antioxidant Capacity)] of the dichloromethane and methanol extracts and the isolated four terpenoids were investigated. Both of the extracts and the isolated four terpenoids exhibited high anticholinesterase activity, particularly against acetylcholinesterase (AChE) enzyme. None of the samples tested showed high antioxidant activity.

Turmeric ( Curcuma longa L.) is a medicinal plant, and its biological activities mainly arise from the main constituent, known as diferuloylmethane or curcumin. In the present paper, microwave-assisted extraction (MAE) was investigated for the recovery of curcumin from turmeric in comparison to conventional heat-assisted extraction (CHAE) technique. Various experimental conditions, such as solvent concentration (0-100%, v/v), MAE temperature (30-130 oC) and MAE time (0-20 min) were investigated to optimize the extraction of curcumin from turmeric. The identification and quantification of curcumin in extracts were performed by HPLC-DAD system. Antioxidant potential and radical scavenging abilities of microwave-assisted extract and conventional heat-assisted extract of turmeric (MAET and CHAET) were evaluated using different systems including total phenolic content (TPC), total antioxidant capacity (TAC), and radical scavenging activities. MAET and CHAET showed high antioxidant activity in all test systems, but the antioxidant properties of MAET were stronger than those of CHAET.

In this research, rose oil and rose water were hydro-distilled from the fresh oil-bearing rose flowers (Rosa damascena Mill.) using Clevenger-type apparatus. Rose concretes were extracted from the fresh rose flowers by using non-polar solvents, e.g. diethyl ether, petroleum ether, cyclo-hexane, chloroform and n-hexane, and subsequently by evaporation of the solvents under vacuum. Absolutes were produced from the concretes with ethyl alcohol extraction at -20°C, leaving behind the wax and other paraffinic substances. Scent compounds of all these products detected by gas chromatography (GC-FID/GC-MS) were compared with the natural scent compounds of fresh rose flower detected by using headspace solid phase microextraction (HS-SPME) with carboxen/polydimethylsiloxane (CAR/PDMS) fiber. A total of 46 compounds analysis were identified by HS-SPME-GC-MS in the fresh flower, and a total of 15 compounds were identified by GC-MS in the hydrodistilled rose oil. While main compounds in rose oil were geraniol (35.4%), citronellol (31.6%), and nerol (15.3%), major compound in fresh rose flower, rose water and residue water was phenylethyl alcohol (43.2, 35.6 and 98.2%, respectively). While the highest concrete yield (0.7%) was obtained from diethyl ether extraction, the highest absolute yield (70.9%) was obtained from the n-hexane concrete. The diethyl ether concrete gave the highest productivity of absolute, as 249.7 kg of fresh rose flowers was needed to produce 1 kg of absolute.

For more bioactive compounds, p hytochemical investigations of the acetone extract of the twigs G arcinia multiflora resulted in the isolation of two new bipheny ls, multiflorabiphenyls A and B (1 and 2 ), along with four known biphenyl derivatives (3-6) . Structural elucidations of 1 and 2 were performed by spectral methods such as 1D and 2D NMR spectroscopy, in addition to high resolution mass spectrometry. Compounds 1 and 2 were also evaluated for their anti-tobacco mosaic virus (Anti-TMV) activity. The results showed that compound s 1 and 2 showed high anti-TMV activit ies with inhibition rate s of 25.4 % and 28.3%, respectively, which is close d to that of Ningnanmycin ( 3 3.5 %).

Essential oils obtained by hydrodistillation from the aerial parts and fruits of five taxa of genus Grammosciadium DC., belonging to subgenus Grammosciadium (G. confertum Hub.-Mor. & Lamond, G. cornutum (Nábělek) C.C.Towns., G. macrodon Boiss. subsp. macrodon, G. macrodon Boiss. subsp. nezaketae B.Bani and G.daucoides DC. ), collected from different locations in Turkey, were simultaneously analyzed by GC and GC/MS systems. 124 components representing 71.1-99.8% of the total contents were identified in the oils. Oil samples from fruits and aerial parts of the plants showed different chemical profiles with regard to species. We have herein demonstrated that the chemical composition of essential oil samples from G. cornutum , G. macrodon subsp. macrodon , G. macrodon subsp. nezaketae (an endemic subspecies) , and G. confertum (an endemic species) growing in Turkey was determined for the first time. Hexadecanoic acid (13.3-21.2% and 48.1-59.8%) was the main component of the samples of G. cornutum and G. confertum, respectively, while caryophyllene oxide (13.1-29.2%) was the major constituent in the samples of G. macrodon subsp. nezaketae and G. macrodon subsp. macrodon as well as γ-terpinene (61.9%) and carvacrol (68.9%) in G. daucoides samples. In addition, pentacosane can be considered a chemotaxonomic marker for the essential oil of G. macrodon subsp. macrodon.

A new 2,3-dihydropyridin-4(1H)-one alkaloid (2), and two other known derivatives (1 and 3) were isolated from Curcuma longa. The isolated alkaloids are shown to be artifacts formed during extraction procedure. Three new (2, 5 and 7) and two known (4 and 6) methoxylated compounds were derived from 1 and 3. Structures were assigned using IR, HRESIMS analyses and 1 and 2D NMR spectroscopy. The anti-migration and anti-proliferation activities against the hepatocellular carcinoma cells, HepG2 were investigated. Compounds 3 showed remarkable anti-migration activity at 40 m M (absolute migration capability, MC A = -7.4 x 10 -4 mm/h). The methylated derivatives 4 showed pronounced anti-migration activity (MC A = -4.9 x 10 -4 mm/h) compared to its parent compound 1 (MC A = 1.49 x 10 -3 mm/h) at 20 m M. The dihydropyridinone derivatives were shown to develop actin stress fibres in treated HepG2 cells which may indicate its role in cell migration inhibition. Compared to curcumins I, II and III, the obtained dihydropyridinone analogues showed lower anti-proliferative activity.

The content of essential oils of endemic Salvia cilicica was analyzed by GC-FID and GC-MS techniques. Spathulenol (23.8 %), caryophyllene oxide (14.9 %) and hexadecanoic acid (10.3 %) were identified as the major components in the oil of Salvia cilicica. Additionally, in this study ethanol extracts of the aerial parts and essential oils of four Salvia species ( S. cilicica, S. officinalis, S. fruticosa, S. tomentosa ) , as well as the roots of S. cilicica were investigated their antimycobacterial and antifungal activities including infectious diseases. The antimycobacterial activity was analyzed against three Mycobacterium tuberculosis (sensitive-, resistant-standard strains and multidrug resistance clinical isolate) strains and the antifungal activity was compared with two dermotophytes (Microsporum gypseum and Trichophyton mentagrophytes var. erinacei) and three Candida species by the broth microdilution method. The essentials oils of the four tested Salvia species showed high antimycobacterial and antifungal activity (MIC between 0.2-12.5 mcg/mL) in comparison to the aerial parts and root extracts . The antifungal and antimycobacterial potential of the ethanol extracts and essential oils were introduced to determine whether, Salvia species can be used in phytotherapy against the yeasts, dermatophytes and M. tuberculosis. To the best of our knowledge this is the first study of S. cilicica about their antimycobacterial and antifungal activities and chemical composition of its essential oils.

Two new phenolic compounds, Schitenoside A (1) and Schitenoside B (2), have been isolated together with six known compounds: 3,4-dihydroxyphenethyl alcohol-4-O-β-D-glucopyranoside (3), 2-(3-hydroxy-4-methoxyphenyl) ethanol 1-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (4), benzyl 7-O-β-D-xylopyranosyl-(1→6)-β-D-glucopyranoside (5), 2-hydroxybenzoic acid (6), m-hydroxybenzoic acid (7) and trans-caffeic acid (8), from the Schizonepeta tenuifolia. Their structures were elucidated by spectroscopic analysis. Compounds (3-7) were isolated from Schizonepeta genus for the first time. Compounds 1 and 2 showed a week antibacterial activity against four test strains, involving both Gram-positive and Gram-negative bacteria .

From the whole plant of Dendrobium tortile, a new compound, namely 4-(2-hydroxypropyl)-2(5H)-furanone, was isolated, together with six known compounds, which included trans-tetracosylferulate (2), cis-docosylferulate (3), p-hydroxybenzaldehyde (4), 3,4-dihydroxy-3,4 ¢ -dimethoxybibenzyl (5), (2S)-eriodictyol (6) and dendrofalconerol A (7). The structures of these compounds were determined through analysis of 1-D and 2-D NMR and HR-ESI-MS data. All of the isolates were evaluated for their a -glucosidase inhibitory activity. Compound 7 showed strong a -glucosidase inhibitory activity when compared with the positive control acarbose, whereas compounds 5 and 6 exhibited appreciable effects. An enzyme kinetic study revealed that compound 7 is a non-competitive inhibitor of a -glucosidase. This is the first report of the chemical constituents with biological activity from D. tortile.

Antibiofilm properties and the phenolic composition of propolis, collected from Bartın province of Turkey in the years of 2013 and 2012, were determined. Hexane, ethyl acetate and ethanol extracts of propolis were prepared and assessed for their antibiofilm activity (inhibition of biofilm formation and reduction of established biofilm) against the clinical methicillin sensitive Staphylococcus aureus (MSSA) strains and Staphylococcus aureus ATCC 33862. Ethyl acetate and ethanol extracts of propolis presented a greater effectiveness on biofilm inhibition of the tested bacteria compared to hexane extracts. The activity patterns showed slight variations in the two years. While 0.5 mg/mL ethyl acetate, ethanol and hexane extract solutions of the product in 2013 inhibited 92.89, 82.98 and 47.42% of biofilm formation of MSSA M20 strain, the inhibition percentage of the products of 2012 were determined to be 87.14%, 75.94% and 44.89% against the same bacterium (MSSA M20), respectively. The results of the validated liquid chromatography-electrospray tandem mass spectrometry (UPLC-ESI-MS/MS) analyses showed a strong relation between the activity and the phenolic composition of the extracts. Phenolic contents of the ethyl acetate and ethanol extracts were relatively higher than hexane extracts. Caffeic acid composition of ethyl acetate, ethanol and hexane extracts of the product in 2013 was detected as 23521.0, 16881.0 and 3522.8 µg/g, respectively. On the other hand, the caffeic acid contents of the product of 2012 was found to be lower than those of 2013 (19100.0, 10416.0 and 2322.5 µg/g for ethyl acetate, ethanol and hexane extracts, respectively). Consequently, the findings have shown that propolis extracts possessed good antibiofilm activity against clinical staphylococci, and its phenolic composition has been affected by the year of collection.

Two new dammarane triterpenes , cereotagalol C ( 1 ) and cereotagalol D (2 ), were isolated from the leaves of Ceriops tagal. Their structures were elucidated by spectroscopic and mass-spectrometric analyses, including 1D-, 2D-NMR and HR -ESI -MS. Their cytotoxic activities against A549, HepG2, HCT-116 and CNE-2 cell lines were also evaluated, which revealed that compounds 1 and 2 had selected moderate cytotoxicity against HCT-116 and CNE-2 with IC 50 values of 29.7 and 37.2 μ M, respectively.

Chemical composition and antimicrobial activity of the essential oil of wild growing Thymus praecox Opiz ssp. polytrichus were studied. trans-Nerolidol (19.79%), germacrene D (18.48%) and thymol (9.62%) were the main components in essential oil. This study is the first report of the antimicrobial activity of essential oil obtained from the T. praecox Opiz ssp. polytrichus. Antimicrobial activity of essential oil was investigated on Bacillus cereus, Micrococcus flavus, Staphylococcus aureus, Listeria monocytogenes, Escherichia coli, Pseudomonas aeruginosa, Enterobacter cloacae, Salmonella typhimurium, Aspergillus fumigatus, A. versicolor, A. ochraceus, A. niger, Trichoderma viride, Penicillium funiculosum, P. ochrochloron, and P. verrucosum var. cyclopium strains. In the antimicrobial assays, essential oil showed high antimicrobial potential (MIC 19–150 m g/mL, MBC 39–300 m g/mL for bacteria; and MIC 19.5–39 m g/mL, MFC 39–78 m g/mL for fungi).

The root of Aralia echinocaulis Hand. -Mazz. ( Araliaceae), are used as traditional Chinese medicine for the treatment of rheumatoid arthritis in China. A phytochemical investigation was carried out to this herb, and obtained twelve secondary metabolites, i.e., syringin (1), adenosine (2), saccharose (3), araliasaponin VII (4), araliasaponin VI (5), araliasaponin XI V (6), araliasaponin XVI (7), syringaresino l (8), 3,4-dihydroxybenzoic acid (9), coniferaldehyde (10), isovanillin (11) and β -sitosterol (12) . Their structures were determined mainly by comprehensive analyses of 1 H and 13 C NMR spectrum and comparison with available literature data or the authentic compounds . To the best of our knowledge, it is the first report that all of compounds have been isolated from the titled plant, and syringin should be one of the major active constituents of A. echinocaulis for the treatment of rheumatoid arthritis.

This study evaluated the chemical composition of Calophyllum ferrugineum, cytotoxicity against human breast cancer (MCF-7) and human lung carcinoma (A-549) cell lines as well as antibacterial activities against two Gram-positive bacteria, S. aureus and B. subtilis and two Gram-negative bacteria, P. aeruginosa and E. coli. Phytochemical investigations of the bark extract yielded isoapetalic acid (1), apetalic acid (2), 6-hydroxy-2-methoxyxanthone (3) and ent-epicatechin (4). Meanwhile, betulinic acid (5), protocatechuic acid (6) and amentoflavone (7) were isolated from the leave extract. Isoapetalic acid (1) and apetalic acid (2) exhibited cytotoxic activities towards both cancer cell lines and both Gram-positive bacteria. Compounds (3-7) were inactive or showed moderate activities towards cytotoxic and antibacterial tests. This study presents the first report on the phytochemicals investigation from C. ferrugineum and all compounds are reported for the first time from this source.

A new 7,8-secolignan, as well as seven known compounds; were isolated from Nectandra turbacensis (Kunth) Nees (Lauraceae) (leaves and root bark). These compounds were identified as, one secolignan, turbacenlignan A (1); four diaryldimethylbutane lignans: meso-monomethyl dihydroguaiaretic acid (2), threo-dihydroguaiaretic acid (3), schineolignin B (4), and austrobailignan-5 (5);and three 7,7' -epoxylignans: henricine (6) and the identifiable mixture of veraguensin (7) and galgravin (8). Compounds 1-8, were first isolated from Nectandra turbacensis (Kunth) Nees (Lauraceae) (leaves and root bark) and compounds 1, 6-8, were isolated for the first time from Nectandra genus.

A new abietane diterpenoid glycoside , leucasinoside , along with two known ones were obtained from the aerial parts of Leucas zeylanica . Its structure was characterized by comprehensive analyses of 1 H , 13 C NMR, COSY, H S QC, HMBC , NOESY spectroscopic, and HREIMS mass spectrometric data. All the isolates were evaluated for their anti-inflammatory activities on lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW264.7, and the new compound showed moderate inhibitory activity.