bluuebunny/crossref_metadata_2025 huggingface dataset:
Antioxidant Activity and Total Phenolic Content of 24 Lamiaceae Species Growing in Iran
Authors: Firuzi Omidreza , Javidnia Katayoun , Gholami Maryam , Soltani Mohammad , Miri Ramin
Published: March 2019

The antioxidant activities of the methanolic extracts of 9 Salvia species and 15 other Lamiaceae plants growing in Iran were evaluated using ferric reducing antioxidant power (FRAP) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging assays. FRAP values ranged form 8.5 to 79.0 μM quercetin equivalents/g dry weight, and IC50 values in the DPPH assay from 115.7 to 1350.2 μg dry weight/mL. Salvia species showed the highest antioxidant activities. S. santolinifolia, S. eremophila and S. palestina, which have not been studied before, were the most active plants. These were more active than the previously studied species from this family, such as S. multicaulis and Marrubium vulgare. S. hydrangea and Gontscharovia popovii also showed high antioxidant activities. FRAP and DPPH assay results showed good correlations with the total phenolic contents of the plants, measured by the Folin-Ciocalteau assay (r2 = 0.925 and 0.799, respectively, p < 0.0001). In conclusion, our study shows that some Lamiaceae plants growing in Iran represent good potential sources of natural antioxidants useful for either prevention or treatment of oxidative stress-related diseases.
Preparation and Characterization of 5′-Phosphodiesterase from Barley Malt Rootlets
Authors: Hua Jie , Huang Ke-long
Published: March 2019

Two 5′- phosphodiesterases (5′-PDE-a and 5′-PDE-b) were isolated from barley malt rootlets, and further purified by gel filtration on Sephadex G-25 and Sephadex G-75. 5′-PDE-a had a pH optimum of 5.0, temperature optimum of 70oC, and specific activity of 0.0143 mM ·mg−1-min−1. 5′-PDE –b had a pH optimum of 6.0, temperature optimum of 65°C and specific activity of 0.0125 mM ·mg−1·min−1. Both enzymes can be used to hydrolyze RNA to form 5′-nucleotides. The enzymes were quite stable at 70oC for 420 minutes. The Km was 0.24 mM for 5′-PDE-a and 0.16 mM for 5′-PDE-b with t-RNA (yeast) as substrate.
Volatile Components of Aerial Parts of Centaurea nigrescens and C. stenolepis Growing Wild in the Balkans
Authors: Formisano Carmen , Senatore Felice , Bancheva Svetlana , Bruno Maurizio , Maggio Antonella , Rosselli Sergio
Published: March 2019

The volatile constituents of the aerial parts of Centaurea nigrescens Willd, collected in Romania and of two samples of C. stenolepis A. Kerner from Bulgaria and Romania were obtained by hydrodistillation and analyzed. The main components of C. stenolepis were caryophyllene oxide (6.9-15.6%), hexahydrofarnesyl acetone (6.5-4.4%), heptacosane (6.0-4.9%) and p-vinyl guiacol (4.3-5.0%). The main components of C. nigrescens were caryophyllene oxide (9.9%), β-eudesmol (9.5%), spathulenol (7.6%), heptacosane (6.1%) and p-vinyl guiacol (5.5%). The chemotaxonomic significance with respect to their co-location in Sections Lepteranthus and Nigrescentes, respectively, is discussed.
Composition at Different Development Stages of the Essential Oil of Four Achillea Species Grown in Iran
Authors: Azizi Majid , Chizzola Remigius , Ghani Askar , Oroojalian Fatemeh
Published: March 2019

Four Achillea species, A. millefolium, A. nobilis, A. eriophora and A. biebersteinii, were grown in small field plots in Iran and harvested at four developmental stages: vegetative, at the appearance of the first flower heads, at full flowering, and at late flowering. The composition of the main volatile compounds in dichloromethane extracts and the essential oil obtained by microdistillation was established by GC/MS and GC. 1,8-Cineole (27-41%) was the main compound in the oils from A. millefolium and A. biebersteinii. These two species reached the highest amount of volatile compounds at the full blooming stage. α-Thujone was the main compound in A. nobilis oil (25-64%). Fully blooming plants of this species also had a high proportion of artemisia ketone (up to 40%) in the oil. The main oil compounds of A. eriophora were camphor (about 35%) and 1,8-cineol (about 30%). This species produces only a small number of flower heads and the composition of the essential oil did not change during development.
Characterization of Szovitsia callicarpa Volatile Constituents Obtained by Micro- and Hydrodistillation
Authors: Demirci Betül , Küçükboyacı Nurgün , Adıgüzel Nezaket , Başer K. Hüsnü Can , Demirci Fatih
Published: March 2019

The volatile constituents of Szovitsia callicarpa Fisch. & C. A. Mey. were obtained from the fruits by microdistillation, due to the limited plant material availability. Initial GC-MS analyses of the obtained material showed an unidentified major constituent with a molecular ion peak at M+ 280. After hydrodistillation of the plant material, the resulting essential oil was also analyzed by GC and GC-MS, simultaneously. In total, twenty-two compounds, representing 98.6% of the microdistilled sample, were identified, whereas seventeen components were detected in the hydrodistilled oil, representing 98.5% of the total. The GC-MS analyses showed that the samples contained an unidentified major constituent, which was further purified from the hydrodistilled essential oil by micro-column chromatography. The structure was elucidated as α-kessyl acetate using 1H- and 13C-NMR spectroscopic and mass spectroscopic techniques. Other major constituents in the analytes were determined as longipinene, longicyclene and kessane. In addition, both samples, as well as the major compound α-kessyl acetate, were tested at 1 mg/mL concentration against the pathogen Candida tropicalis and for its free radical scavenging activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH•) by TLC-bioauthographic techniques. Both preliminary assays at the tested concentration showed no activity.
Chemical Composition and Antibacterial Activity of the Essential Oil from Fruits of Bursera tomentosa
Authors: Moreno José , Aparicio Rosa , Velasco Judith , Rojas Luis B , Usubillaga Alfredo , Lue-Merú Marcó
Published: March 2019

The hydrodistilled oil from the fruits of Bursera tomentosa, obtained in 0.2% yield, was analyzed by GC-MS. Nine components were identified, which made up 99.3% of the oil. The most abundant constituents were cis-ocimene (47.6%), n-nonane (28.2%) and germacrene-D (11.1%). The oil showed antibacterial activity against Staphylococcus aureus (ATCC 25923), Enterococcus faecalis (ATCC 29212) and Salmonella typhi (CDC 57), with MIC values of 80 μg/mL, 120 μg/mL and 100 μg/mL, respectively.
Composition and Antioxidant Activity of Inula crithmoides Essential Oil Grown in Central Italy (Marche Region)
Authors: Giamperi Laura , Bucchini Anahi , Fraternale Daniele , Genovese Salvatore , Curini Massimo , Ricci Donata
Published: March 2019

The chemical composition of the essential oil obtained from the aerial parts of Inula crithmoides L. was analyzed by GC and GC/MS and 22 components were identified, the major ones being p-cymene (30.1%), 1-methylethyl-trimethylbenzene (18.7%), scopoletin (15.3%) and α-pinene (13.1%). The antioxidant activity of the oil was evaluated by the DPPH test and 5-lipoxygenase assay. The essential oil exerted a good antioxidant activity in the protection of lipid peroxidation when compared with known antioxidants.
Antifungal Activities of Ocimum sanctum Essential Oil and its Lead Molecules
Authors: Khan Amber , Ahmad Aijaz , Manzoor Nikhat , Khan Luqman A.
Published: March 2019

Aqueous extracts and oils of five Indian medicinal plants, traditionally used for their antimicrobial activities, were evaluated against two of the most prevalent Candida species causing candidiasis, C. albicans and C. tropicalis. Of these plant materials, three showed varying degrees of antifungal activity against both species. Tulsi (Ocimum sanctum Linn.) essential oil (TEO) was found to be the most effective, followed by Peppermint essential oil, and Aloe vera aqueous leaf extract. The product with the lowest MIC was further studied along with its lead molecules to explore the possible mechanism of action of the most active constituents. Eugenol, methyl eugenol, linalool, and 1, 8-cineole, along with TEO were then evaluated at the same. The pattern and extent of inhibition was studied using growth and WST1 cytotoxicity assays. Proton pumps are important for growth and metabolism of Candida species and so H+ extrusion studies were performed to explore the possible mechanism of the test compounds. Linalool was the most active constituent of TEO, whereas inhibition of H+ extrusion appeared to be a synergistic function of the lead molecules.
Three New Insecticidal Sesquiterpene Polyol Esters from Celastrus angulatus
Authors: Wei Shaopeng , Wang Minchang , Ji Zhiqin , Shi Baojun , Li Shengkun , Zhang Jiwen
Published: March 2019

Three new insecticidal sesquiterpene polyol esters with dihydro-β-agarofuran skeletons, Kupiteng esters A (1), B (2) and C (3), were isolated from the methanol extracts of the root bark of Celastrus angulatus and their structures elucidated by analyses of MS and NMR spectral data. The insecticidal activities of these compounds against the 4th instar larvae of Mythimna separata were evaluated. The KD50 values of compounds 1-3, were 260.2, 445.5 and 1260.0 μg-g−1, respectively.
Triterpenoids from Aerial Parts of Glochidion eriocarpum
Authors: Thu Vu Kim , Van Kiem Phan , Yen Pham Hai , Nhiem Nguyen Xuan , Tung Nguyen Huu , Cuong Nguyen Xuan , Van Minh Chau , Huong Hoang Thanh , Van Lau Trinh , Thuan Ngo Thi , Kim Young Ho
Published: March 2019

From the aerial parts of Glochidion eriocarpum, a new triterpene, glochieriol (1), three new triterpenoid saponins, glochieriosides C - E (2 - 4), together with four known triterpenes (glochidonol, glochidiol, lupeol, and 3- epi-lupeol) were isolated by using combined chromatographic separations. The structures of the new compounds were elucidated on the basis of spectroscopic data, including FTICR-MS, 1D and 2D NMR.
Identification of Sakurasosaponin as a Cytotoxic Principle from Jacquinia flammea
Authors: Sánchez-Medina Alberto , Peña-Rodríguez Luis M. , May-Pat Filogonio , Karagianis Gloria , Waterman Peter G. , Mallet Anthony I. , Habtemariam Solomon
Published: March 2019

The crude ethanolic extract of leaves, stem-bark and roots of J. flammea were tested for their cytotoxic effect against two mammalian cell lines (HeLa and RAW 264.7) and four bacterial species (Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Pseudomonas aeruginosa). When tested at the concentration of 100 μg/mL, the root extract showed the highest cytotoxic activity against mammalian cells followed by the stem-bark extract while the leaves extract did not show significant activity. No antibacterial activity was detected for all extracts when tested up to 500 μg/disc in the disc diffusion assay. The cytotoxic root extract was subjected to fractionation using solvents of ascending polarity: petroleum ether, chloroform, ethylacetate, butanol and water. The water fraction which showed cytotoxic activity was further subjected to routine bioassay-guided fraction to lead to the isolation of sakurasosaponin as the active principle. The recorded IC50 value for sakurasosaponin was 11.3 ± 1.52 and 3.8 ± 0.25 μM (n=3) against HeLa and RAW 264.7 respectively. The identification of sakurasosaponin was based on analysis of spectroscopic data.
Vasoconstrictor and Inotropic Effects Induced by the Root Bark Extracts of Anthocleista schweinfurthii
Authors: Ngombe Nadège Kabamba , Kalenda Dibungi T. , Quetin-Leclercq Joëlle , Morel Nicole
Published: March 2019

The present study was undertaken to investigate the cardiovascular effect of three extracts from the root bark of Anthocleista schweinfurthii Gilg.: an aqueous extract (AE), a dichloromethane extract (DCMR) and a fraction enriched in cardiac glycoside type compounds (CARDAN). In isolated perfused frog heart, bolus injection of the extracts produced a positive inotropic effect. The responses to AE and DCMR, but not to CARDAN, were depressed by propranolol. In isolated rat aorta, DCMR produced a transient increase in contractile tension while AE and CARDAN induced a sustained constriction. AE vasoconstrictor effect was abolished by phentolamine, while contraction evoked by CARDAN was antagonized by verapamil. In aortic rings contracted in low K+ media, the addition of K+ evoked a relaxation, which was abolished by ouabain, depressed by DCMR but not affected by either AE or CARDAN. These observations indicate that Anthocleista schweinfurthii contains substances that promote vasoconstriction and increase cardiac contraction. The effect of DCMR was only partially mediated by inhibition of the Na+ pump while the mechanism of action of AE and CARDAN was distinct from the inhibition of the Na+,K+-ATPase pump, but could involve adrenergic receptors, or either direct or indirect activation of L-type calcium channels.
Hydroxylation of Diosgenin by Absidia coerulea
Authors: Zhao Ying , Sun Ling-Mei , Wang Xiao-Ning , Shen Tao , Ji Mei , Lou Hong-Xiang
Published: March 2019

Microbial transformation of diosgenin (1) using Absidia coerulea yielded five new polar metabolites, which were identified as (25 R)-spirost-5-en-3β,7β,12β,25α-tetrol (2), (25 S)-spirost-5-en-3β,7α,12β,25β-tetrol (3), (25 S)-spirost-5-en-3β,7β,12β,25β-tetrol (4), (25 R)-spirost-5-en-3β,7α,12β,25α-tetrol (5), and (25 R)-spirost-5-en-3β,7β,12β,24β-tetrol (6). Their structures were established on the basis of mass spectrometry and multi-dimensional NMR spectroscopy. The characteristic transformations observed were C-7α, C-7β, C-12β, C-24β, C-25α, and C-25β hydroxylation. The cytotoxicity of compounds 1–6 was evaluated against the human myelogenous leukemia K562 cell line and squamous cell carcinoma KB parental cell lines. Compounds 2–6 exhibited weak cytotoxicity against K562 and KB cells and were less potent than the parent compound 1.
Dibromotyrosine and Histamine Derivatives from the Tropical Marine Sponge Aplysina sp
Authors: Santalova Elena A. , Denisenko Vladimir A. , Stonik Valentin A.
Published: March 2019

Two new compounds, 3-amino-7,8-dihydroimidazo-[1,5-c]-pyrimidin-5(6H)-one (1) and ethyl 3-(2-amino-1H-imidazol-4-yl)propylcarbamate (2), along with the previously known 7,8-dihydroimidazo-[1,5-c]-pyrimidin-5(6H)-one (3), aeroplysinin-1 (4), dibromoverongiaquinol (5), bisoxazolidinone derivative (6), aerophobins-1 (7) and −2 (8), purealidins J (9) and L, have been isolated from Aplysina sp. from the South China Sea. The structures were elucidated on the basis of 1H, 13C NMR, MS and IR analyses. The histamine-derived alkaloids 1-3 may be unknown bioconversion products of purealidin J (9), aerophobin-2 (8) and aerophobin-1 (7), respectively, when 7-9 are cleaved at C-8–C-9 in reactions of activated chemical defense in Aplysina sponge.
Insecticidal, Mutagenic and Genotoxic Evaluation of Annonaceous Acetogenins
Authors: Colom Olga Álvarez , Salvatore Analia , Willink Eduardo , Ordóñez Roxana , Isla María I. , Neske Adriana , Bardón Alicia
Published: March 2019

Annonaceous acetogenins represent a class of bioactive compounds whose primary mode of action is the inhibition of NADH-ubiquinone oxidoreductase (Mitochondrial Complex I). Given the potential pesticidal use of these compounds, we evaluated the effects of seven acetogenins: squamocin (1), molvizarin (2), itrabin (3), almuñequin (4), cherimolin-1 (5), cherimolin-2 (6), and tucumanin (7) isolated from Annona cherimolia Mill. against Ceratitis capitata Wiedemann (Tephritidae). These acetogenins did not display insecticidal action at 250 μg of treatment per g of adult diet. However, the oviposition capacity of C. capitata females was significantly altered by some of the acetogenins at this concentration. The most potent compounds were itrabin, molvizarin and squamocin. Moreover, significant differences were detected in the preference of oviposition sites when itrabin and squamocin were spread on the surface of artificial fruits at doses of 30 μg/cm2. Additionally, we investigated the mutagenic effects displayed by itrabin, as well as the phytotoxic and genotoxic action of squamocin and itrabin. Both compounds displayed slight phytotoxic and genotoxic effects on roots of Allium cepa at 2.5 μg/mL though no mutagenic effects were detected at 0.25, 0.5 and 2.5 μg/mL on Salmonella typhimurium strains TA98 and TA100.
Phenolic Compounds in Different Barley Varieties: Identification by Tandem Mass Spectrometry (QStar) and NMR; Quantification by Liquid Chromatography Triple Quadrupole-Linear Ion Trap Mass Spectrometry (Q-Trap)
Authors: Klausen Kamilla , Mortensen Anne G. , Laursen Bente , Haselmann Kim F. , Jespersen Birthe Møller , Fomsgaard Inge S.
Published: March 2019

Barley (Hordeum vulgare) is an important cereal that has many applications; as a human food, in malt products and as livestock feed. The content of soluble health-promoting fibers, β-glucans, varies substantially among barley varieties. In the present study, the content of secondary metabolites with potential positive health effects in different high- and low-β-glucan barley varieties was studied. Five different flavanols were isolated and identified: (2 R,3 S)-catechin-7- O-β-D-glucopyranoside (1), prodelphinidin B3 (2), procyanidin B3 (3), (+)-catechin (4) and procyanidin B1 (5). Procyanidin B1 has never been reported in barley grains before. The compounds were identified using 1H NMR and quadrupolar time-of-flight mass spectrometry. A quantitative analytical method was developed for prodelphinidin B3, procyanidin B3 and (+)-catechin in liquid chromatography triple quadrupole-linear ion trap mass spectrometry and these compounds were quantified in all varieties, together with four phenolic acids: ferulic acid, vanillic acid, p-coumaric acid and p-hydroxybenzoic acid. Catechin was the compound that was present at the highest concentration in all varieties. The variation, between cultivars, in catechin concentration varied four fold. A Principal Component Analysis indicated no correlation between concentrations of β-glucan and secondary metabolites. Concentrations of catechin and prodelphinidin B3 were strongly correlated, whereas the concentration of procyanidin B3 was not correlated with that of catechin or prodelphinidin B3. Either two different enzymes could be responsible for the dimerization of prodelphinidin B3 and procyanidin B3, or the affinity of the enzyme could be different whether the dimerization is between two catechin units or between units of gallocatechin and catechin.
Two New Carthamosides from Carthamus oxycantha
Authors: Hassan Zahid , Ahmad Viqar Uddin , Hussain Javid , Zahoor Aqib , Siddiqui Imran Nafees , Rasool Nasir , Zubair Muhammad
Published: March 2019

Two new glycosides, 2- O-methylglucopyranosyl-carthamoside (1) and β-D-fructofuranosyl carthamoside (2), along with the known compound 3’,4’,5,7-tetrahydroxyflavanone (3) have been isolated from Carthamus oxyacantha, using recycling preparative HPLC. The structures of these compounds were established by mass spectrometric and extensive spectroscopic analysis.
Tectone, a New Antihyperglycemic Anthraquinone from Tectona grandis Leaves
Authors: Shukla Nivedita , Kumar Manmeet , Akanksha  , Ahmad Ghufran , Rahuja Neha , Singh Amar B. , Srivastava Arvind K. , Rajendran Siron M. , Maurya Rakesh
Published: March 2019

A new anthraquinone (3,8-dihydroxy-2-methyl anthraquinone), named tectone (1), along with fourteen known compounds (2-15) comprised of five terpenoids (2-5, 15), four flavonoids (6-9), three flavone glycosides (10-12), and two phenolic glycosides (13-14) were isolated from the chloroform and n-butanol fractions of the ethanol extract of Tectona grandis leaves. Attempts were made to synthesize compound 1. This resulted in the synthesis of three additional anthraquinones (16-18), out of which compound 16 is new. The structures of all compounds were established by spectral analysis. The isolated and synthesized compounds were evaluated for their antihyperglycemic activity. Compounds 1, 2, 4 and 14 showed significant antihyperglycemic activity in streptozotocin-induced diabetic rats at a dose of 100 mg/kg body weight, which is comparable to the standard drug metformin.
A Semiquantitative FIA-ESI-MS Method for the Rapid Screening of Hypericum perforatum Crude Extracts
Authors: Piovan Anna , Filippini Raffaella , Caniato Rosy
Published: March 2019

A method based on FIA-ESI-MS has been developed to profile the major constituents of Hypericum perforatum extracts. The objective was to obtain simultaneous semi-quantitative data on hypericin, chlorogenic acid, rutin, quercitrin, quercetin and hyperforin contents for a high-throughput screening of the raw plant material. The principal drawback of FIA-ESI analysis of complex mixtures involves ion suppression effects: the ionization of some components of the mixture can be severely suppressed by ionization of others. The results show that this problem can be alleviated using a new approach to generate calibration curves.
Variability of the Essential Oil Content and Composition of Chamomile (Matricaria recutita L.) affected by Weather Conditions
Authors: Gosztola Beáta , Sárosi Szilvia , Németh Έva
Published: March 2019

In our study we examined the variability of the essential oil content and composition of chamomile (Matricaria recutita L.) during three years (2005-2007). Twenty-eight populations of wild origin and 4 registered cultivars (‘Soroksári 40’, ‘Lutea’, ‘Goral’ and ‘Bona’) were evaluated in open field experiments. It could be established that the experimental populations represented different genetic potential for essential oil accumulation and composition. The best populations of wild growing origin from the Somogy-region and four cultivars produced the highest essential oil contents (above 0.6 g/100g) in each year. Additionally, the quality of the characteristic main compound of the oil determining the “chemotype “, according to Schilcher, was found to be stable during the three years period. However, the actual chemosyndroms are significantly influenced by the weather conditions. In the three years’ experiment, the moderately warm and relatively wet year of 2006 produced the highest contents of essential oil and also that of its α-bisabolol component. Although bisabolol oxide A also showed a high variability through the years, its direct connection with weather conditions could not be proved. A moderate variability was established for the proportions of chamazulene, and the lowest one for bisabolol-oxide B. Considerable genotype-weather interaction was supposed, especially for the essential oil content and for the ratio of bisabolol-oxide A.
Chemical Composition, Toxicity and Larvicidal Activity of the Essential Oil from the Whole Plant of Acalypha segetalis from South-West Nigeria
Authors: Aboaba Sherifat A. , Aiyelaagbe Olapeju O. , Ekundayo Olusegun
Published: March 2019

The chemical composition of the essential oil from the whole plant of Acalypha segetalis Muell. Arg. was analyzed by GC and GC/MS. Nineteen volatile constituents were identified. The main compounds were α-pinene (8.5%), neophytadiene, isomer II (14.7%) and neophytadiene, isomer III (33.6%). Toxicity and larvicidal assays revealed that the plant had LC50 values of 14.0 μg/mL and 45.4 μg/mL respectively.
Biotransformation of α-Cedrol and Caryophyllene Oxide by the Fungus Neurospora crassa
Authors: Kiran Ismail , Durceylan Zeynep , Kirimer Neşe , Başer K. Hüsnü Can , Noma Yoshiaki , Demirci Fatih
Published: March 2019

Incubation of α-cedrol and caryophyllene oxide with Neurospora crassa afforded 12β-hydroxy cedrol, 10α-hydroxy cedrol, and 3β-hydroxy cedrol, and 12β-hydroxy caryophyllene oxide as major metabolites, respectively. The antibacterial and radical scavenging activities of the metabolites were evaluated in vitro using broth microdilution and bioauthographic techniques. However, no significant antibacterial and antioxidant activities were observed when compared with those of standard substances.
Two New Diterpene Phenols from Calocedrus decurrans
Authors: Veluthoor Sheeba , Li Shujun , Kelsey Rick G. , Dolan Marc C. , Panella Nicholas A. , Karchesy Joe
Published: March 2019

Two new p-cymene based diphenols (1-2) were isolated from the heartwood of Calocedrus decurrans. Structures were elucidated by 1D and 2D NMR techniques and HRMS. Libocedroquinone (3) was also isolated as a natural product for the first time. A new system of nomenclature is proposed for description of such oligomeric p-cymene derivatives.
Vitamin E Ameliorates High Dose trans-Dehydrocrotonin-Associated Hepatic Damage in Mice
Authors: Rabelo Alana Fontales Lima , Guedes Marjorie Moreira , da Rocha Tomé Adriana , Lima Patricia Rodrigues , Maciel Maria Aparecida , de Sousa Lira Silveria Regina , da Silva Carvalho Ana Carla , Santos Flávia Almeida , Rao Vietla Satyanarayana
Published: March 2019

trans-Dehydrocrotonin ( t-DCTN), the diterpenoid from Croton cajucara Bentham, exhibits hypoglycemic and hypolipidemic activities, but in high doses is associated with a discrete hepatotoxicity. In the search for measures to mitigate this, pretreatment with the antioxidants N-acetylcysteine and vitamin E has been examined. Mice that received a high dose t-DCTN (100 mg/kg) manifested hepatic damage, as evidenced by significant elevations in serum ALT and AST, and hepatic GSH, and histological alterations, which could be obliterated by pretreatment with vitamin E, but not with N-acetylcysteine, possibly by creating an effective antioxidant balance.
A Pentacyclic Triterpene from Litchi chinensis
Authors: Malik Imran , Ahmad Viqar Uddin , Anjum Shazia , Basha Fatima Z.
Published: March 2019

The aerial parts of Litchi chinensis Gaertn. (Sapindaceae) yielded one new pentacyclic triterpene [lup-12, 20(29) diene-3, 27-diol], along with the known compounds betulinic acid, lupeol, betulin, β-sitosterol, and stigmasterol. The structures of the compounds were established by spectroscopic methods.
Ellagitannins from Geranium potentillaefolium and G. bellum
Authors: Gayosso-De-Lucio Juan A. , Torres-Valencia J. Martín , Cerda-García-Rojas Carlos M. , Joseph-Nathan Pedro
Published: March 2019

The aerial parts of Geranium potentillaefoium afforded geraniin (1), corilagin (2), gallic acid (4), methyl gallate (6), methyl brevifolincarboxylate (7), quercetin, quercetin 3- O-β-D-glucopyranoside, quercetin 3- O-β-D-[6″- O-galloyl)glucopyranoside, kaempferol, β-sitosterol 3- O-β-D-glucopyranoside and β-sitosterol, while the aerial parts of G. bellum gave the same compounds in addition to kaempferol 3- O-β-D-glucopyranoside, isolated instead of kaempferol. The substances were identified by 1D and 2D NMR spectroscopy in comparison with published data. The water decoction preparations from air-dried plant materials (2.5 g) contain ca. 4.6 % of the ellagitannin 1, envisaging that when such decoction is ingested (250 mL), a therapeutic dose of ca. 36 mg of the antitumor ellagic acid (3) may be incorporated into the organism.
Chemical Analysis of the Principal Flavonoids of Radix Hedysari by HPLC
Authors: Liu Yi , Zhao Yuying , Chen Hubiao , Wang Bin , Zhang Qingying
Published: March 2019

Five major flavonoids in 48 batches of Radix Hedysari from different origins have been simultaneously evaluated by HPLC. Among the five major flavonoids, four, ononin, formononetin-7- O-β-D-glucopyranoside-6″- O-malonate, formononetin and medicarpin, were detected in almost all the samples and thus can be used as marker compounds to evaluate the chemical quality of Radix Hedysari, while naringin was not suitable because it was not be detected in most samples. Further analysis of the contents of the four flavonoids in different samples showed that processing procedure, harvesting time and habitats were important factors affecting the flavonoid contents of Radix Hedysari.
A Chromone from Seseli praecox (Apiaceae)
Authors: Leonti Marco , Casu Laura , Solinas Maria Novella , Cottiglia Filippo , Caboni Pierluigi , Floris Costantino , Gertsch Juerg , Saba Anna Rita
Published: March 2019

Chemical investigation of the stems of Seseli praecox (Gamisans) Gamisans, an endemic Apiaceae from Sardinia, afforded an isopropenylated chromone (5-hydroxy-6-(2- Z-butenyl-3-hydroxymethyl)-7-methoxy-2-methylchromone), along with four known linear furocoumarins and their natural precursor. For biological characterization the new compound was screened against four cancer cell lines in vitro and showed differential μM antiproliferative effects between suspension and adherent cells.
Determination of Chromones in Dysophylla stellata by HPLC: Method Development, Validation and Comparison of Different Extraction Methods
Authors: Gautam Raju , Srivastava Amit , Jachak Sanjay M.
Published: March 2019

An HPLC method with reflux as an efficient extraction method has been developed for quantification of chromones in Dysophylla stellata Benth. Separation was achieved on a C18 column with a mobile phase of 0.5% (v/v) acetic acid in water (A), and ACN (B) under gradient elution at 1 mL/min. Chromones (1 and 2) isolated from D. stellata were used as standards for method development and validation was achieved according to ICH guidelines. Extracts prepared by three different methods [reflux, ultrasonication and accelerated solvent extraction (ASE)] were used for analysis by the validated method. The proposed HPLC method is simple, accurate and selective for the separation and quantification of chromones in D. stellata.
Differentiation of Symphytum Species Using RAPD and Seed Fatty Acid Patterns
Authors: Özcan Tamer
Published: March 2019

RAPD and fatty acid profiles, and α-tocoferol contents of the seeds of some Symphytum species were analyzed for their differentiation. Discriminative patterns were found in the examined species. Genotypic characteristics of three Symphytum species were experienced using 20 decamer RAPD primers. The majority of band positions varied between species. The total amplified products of 20 RAPD primers was 247 (average of 12.35 bands per primer), of which 189 bands were polymorphic, corresponding to nearly 76.1% genetic diversity. The number of bands for each RAPD primer varied from 8 (UBC320) to 18 (OPA7). The percent of polymorphic bands ranged from 45.4% (OPJ20) to 93.3% (OPA16). Major unsaturated fatty acids in the seeds were linoleic, γ-linolenic and oleic acids; α-linolenic and eicosenoic acids exhibited lower levels. Variations in quantities and total ratios of fatty acid groups, and α-tocopherol contents were also observed between the species, and the developmental stages of the seeds. Significant differences were found for the whole series of fatty acids between species, in addition to the calculated ratios ( p < 0.05). Differences were also significant for fatty acid traits between two developmental stages of the seeds of endemic S. pseudobulbosum ( p < 0.05). In some morphological descriptors of the seeds, difference was found at a significant level ( p < 0.05). Obtained data based on genetic and biochemical variations seem to be useful for molecular delimitation of Symphytum, in addition to selection of the genotypes expressing a high amount of GLA.
New Angucyclines and Antimicrobial Diketopiperazines from the Marine Mollusk-Derived Actinomycete Saccharothrix espanaensis An 113
Authors: Kalinovskaya Nataliya I. , Kalinovsky Anatoly I. , Romanenko Lyudmila A. , Dmitrenok Pavel S. , Kuznetsova Tatyana A.
Published: March 2019

Two new angucyclines, saccharothrixmicines A (2) and B (3), together with three known diketopiperazines 4-6 were isolated from the actinomycete Saccharothrix espanaensis An 113 associated with the marine mollusk Anadara broughtoni. Their structures were determined by HRESIMS and 1D and 2D NMR. Compounds 2 and 3 differ in aglycone and glycosidic bond type. 2 is an α-L-6-deoxyaltrose-phenylglycoside of a benz[a]anthraquinone aglycone, while 3 is an O-glycoside of the same sugar linked to C-7 of the known angucyclinone (1). A saccharothrixmicine-containing fraction exhibited activity towards Candida albicans and Xanthomonas sp. pv. badrii whereas the diketopiperazines showed antibiotic activities against Vibrio alginolyticus and Vibrio parahaemolyticus.
Essential Oil from Leaves of Lippia dulcis Grown in Colombia
Authors: Moreno-Murillo Bárbara , Quijano-Célis Clara , Arturo Romero R. , Pino Jorge A.
Published: March 2019

The chemical composition of the volatile compounds from the leaves of Lippia dulcis Trev. (Verbenaceae) from Colombia was studied by GC and GC/MS. Forty volatile compounds were identified, of which the major ones were α-copaene (18.0%), β-caryophyllene (17.8%), and δ-cadinene (14.7%). The sweet bisabolane sesquiterpenoid, hernandulcin, formed only 1.1% of the leaf oil.
Comparison of the Volatile Constituents of Elsholtzia fruiticosa Extracted by Hydrodistillation, Supercritical Fluid Extraction and Head Space Analysis
Authors: Saini Rikki , Guleria Shailja , Kaul Vijay K. , Lal Brij , Babu Garikapati D. Kiran , Singh Bikram
Published: March 2019

Volatile constituents of Elsholtzia fruiticosa (D. Don) Rehder were studied by two different extraction techniques, supercritical fluid extraction (SFE) and hydrodistillation (HD), and the results were compared with head space analysis (HS). Thirty-five constituents were identified in both the SFE and HD oils and fourteen in the HS, accounting for 94.2%, 97.7% and 96.9% of the total identifications, respectively. A distinctive feature of the results was the very high content of non-terpenes (59.8%) in the HS, the high content of oxygenated monoterpenes (41.1%) in the HD oil and the high content of sesquiterpene hydrocarbons (21.8%) in the SFE oil. Monoterpene hydrocarbons were represented in HS (13.6%), HD (19.4%) and SFE (4.3%). In SFE sesquiterpene hydrocarbons formed 21.8% of the total, as compared to 6.6% in the HD and 1.1% in the HS Oxygenated sesquiterpenes represented 3.0% in SFE, 0.8% in HD and were absent in HS. Diterpenes were only present in the SFE oil (3.4%). Non-terpenes were represented by 24.5% in the SFE oil and 29.8% in the HD oil.
The Effect of Essential Oil Formulations for Potato Sprout Suppression
Authors: Owolabi Moses S. , Lajide Labunmi , Oladimeji Matthew O. , Setzer William N.
Published: March 2019

The concerns over safety and environmental impact of synthetic pesticides such as chlorpropham (CIPC) has stimulated interest in finding environmentally benign, natural sprout suppressants, including essential oils. The effects of Chenopodium ambrosioides and Lippia multiflora essential oils on sprout growth and decay of stored potatoes has been investigated. Formulations of essential oils with alumina, bentonite, or kaolin, both with and without Triton X-100 additive, were tested. These formulations have been compared to the pulverized plant materials themselves as well as wick-volatilized essential oils. The results showed that the tested oils possess compositions that make them suitable for application as sprout suppressants. Additionally, the formulation seems to be able to reduce the volatility of the essential oil and artificially extend dormancy of stored potatoes.
A new Bisabolane Derivative of Leontopodium andersonii
Authors: Schwaiger Stefan , Hehenberger Stefanie , Ellmerer Ernst P. , Stuppner Hermann
Published: March 2019

Phytochemical investigations of the roots of Leontopodium andersonii C. B. Clarke (Asteraceae) resulted in the isolation of a new bisabolane sesquiterpene derivative. The structure of the highly substituted derivative (1 R*,5 S*,6 S*)-5-(acetyloxy)-6-[3-(acetyloxy)-1,5-dimethylhex-4-enyl]-3-methylcyclohex-2-en-4-on-1-yl (2 Z)-2-methyl-but-2-enoate was established by 1- and 2-D-NMR spectroscopy and is the first report of a bisabolone derivative of the genus Leontopodium.
Acid Rearrangment of Epoxy-germacranolides and Absolute Configuration of 1β,10α-Epoxy-salonitenolide
Authors: Rosselli Sergio , Maggio Antonella Maria , Raccuglia Rosa Angela , Morris-Natschke Susan L. , Bastow Kenneth F. , Lee Kuo-Hsiung , Bruno Maurizio
Published: March 2019

The acid-catalyzed cyclization of mono epoxides of cnicin acetonide (3) was investigated. Several 6,12-eudesmanolides were obtained, and their stereochemistry established by extensive spectroscopic analyses. Chemical correlations also led to the assignment of the absolute configuration of 1β,10α-epoxy-salonitenolide (13), a previously isolated natural product. The cytotoxic activities of some compounds were determined against A549 and MCF-7 tumor cell lines. The esterified germacranolides 2–6 were selectively cytotoxic against the MCF-7 breast cancer cell line.
Sesquiterpenes Lactones and Flavonoids from Eremanthus argenteus (Asteraceae)
Authors: Sakamoto Humberto Takeshi , Laudares Eugênio Paceli , Crotti Antônio Eduardo Miller , Lopes Norberto Peporine , Vichnewski Walter , Lopes João Luis Callegari , Heleno Vladimir Constantino Gomes
Published: March 2019

Two new sesquiterpene lactones 8α-(2’,3’-dihydroxy-2’-methylbutanoyl)-15-desoxygoyazensolide and 16α-(1’,2’-dihydroxy-1’-methylpropyl)-eremantholide have been identified as constituents of Eremanthus argenteus aerial parts. In addition, two known sesquiterpene lactones and three flavonoids were isolated. Their structures were established on the basis of spectroscopic and spectrometric data.
Biotransformation of Sesquiterpenoids from Liverworts by Fungi and Mammals
Authors: Asakawa Yoshinori , Hashimoto Toshihiro , Noma Yoshiaki
Published: March 2019

Biotransformation of sesquiterpenoids isolated from several liverworts using various fungi and mammals is summarized. Microorganisms introduce an oxygen atom at an allylic position to give secondary hydroxyl and keto groups. The cyclopentane ring is also oxidized to afford monoketo, and mono- and diols. Double bonds are also either reduced or oxidized to give either saturated compounds or epoxides, followed by hydrolysis to afford diols. The methyl group is oxidized to give a primary alcohol. Some fungi cleave the cyclopropane ring to form a 1,1-dimethyl group. These reactions precede stereo- and regio-specifically. Cytochrome P-450 is responsible for the introduction of an oxygen function into the substrates. The present methods are cheap, one step reactions, non-hazardous, and very useful for the production of some bioactive compounds from a large number of terpenoids found in liverworts and higher plants.
Identification and Functional Characterization of a new Sunflower Germacrene A Synthase (HaGAS3)
Authors: Göpfert Jens , Bülow Anna-Katharina , Spring Otmar
Published: March 2019

Sesquiterpenes and sesquiterpene lactones are major natural compounds found in linear and capitate glandular trichomes of sunflower, Helianthus annuus L. In addition to two recently identified germacrene A synthases HaGAS1 and HaGAS2, found in capitate trichome gland cells, reverse transcription-PCR experiments have now allowed identification of a third enzyme of this type, HaGAS3. Its cDNA sequence was established and its functional characterization as a germacrene A synthase was achieved through in vitro expression in engineered yeast, and by GC-MS experiments. PCR and RT-PCR experiments with cDNA from different plant organs revealed that the new enzyme is expressed independently from the other two. While these latter two were expressed in plant organs bearing capitate glandular trichomes and in roots, the new enzyme occurred in plant tissues not linked to the presence of specific trichomes (for example, cotyledons), and was absent in roots. The experiments show that independently regulated pathways for the first cyclic sesquiterpene, germacrene A, are present in sunflower.
Natural Products from Scorzonera aristata (Asteraceae)
Authors: Jehle Manuela , Bano Johanna , Ellmerer Ernst P. , Zidorn Christian
Published: March 2019

The aerial parts of Scorzonera aristata Ramond ex DC., collected in the South Tyrolean Dolomites, yielded the flavonoids quercetin 3- O-glucoside, rutin, and isoorientin, and the caffeic acid derivatives chlorogenic acid, 4,5-dicaffeoyl quinic acid, and 3,5-dicaffeoyl quinic acid. Sub-aerial parts contained caffeic acid methyl ester, 3,5-dicaffeoyl quinic acid, and the triterpenes 3α-hydroxyolean-5-ene, lupeol, and magnificol. Chemosystematic implications of the isolated compounds are discussed briefly.
Effects of Caffeoylquinic Acid Derivatives and C-Flavonoid from Lychnophora ericoides on in vitro Inflammatory Mediator Production
Authors: Santos Michel David dos , Chen Guanjie , Almeida Maria Camila , Soares Denis Melo , de Souza Glória Emília Petto , Lopes Norberto Peporine , Lantz R. Clark
Published: March 2019

In this study we aimed at evaluating the effect of the major polar constituents of the medicinal plant Lychnophora ericoides on the production of inflammatory mediators produced by LPS-stimulated U-937 cells. The 6,8-di- C-β-glucosylapigenin (vicenin-2) presented no effect on tumor necrosis factor (TNF)-α production, but inhibited, in a dose-dependent manner, the production of prostaglandin (PG) E2 without altering the expression of cyclooxygenase (COX) -2 protein. 3,5-Dicaffeoylquinic acid and 4,5-dicaffeoylquinic acid, at lower concentrations, had small but significant effects on reducing PGE2 levels; at higher doses these compounds stimulated PGE2 and also TNF-α production by the cells. All the caffeoylquinic acid derivatives, in a dose-dependent fashion, were able to inhibit monocyte chemoattractant protein-3 synthesis/release, with 4,5-DCQ being the most potent at the highest tested concentration. These results add important information on the effects of plant natural polyphenols, namely vicenin-2 and caffeoylquinic acid derivatives, on the production of inflammatory mediators by cultured cells.
A New Bianthracene C-arabinopyranoside from Senna septemtrionalis
Authors: Alemayehu Gizachew , Adane Legesse , Abegaz Berhanu M.
Published: March 2019

Chrysophanol, physcion, emodin, floribundone-1, 5,7′-physcion-fallacinol, and the novel 5,7′-physcion-physcion-10′- C-α-arabinopyranoside were isolated from the stem bark of Senna septemtrionalis. The structures of these secondary metabolites were determined on the basis of spectroscopic analysis, especially from NMR spectra in conjunction with COSY, HMQC, HMBC and TOCSY.
Computer-aided Structure Elucidation of Neolignans
Authors: Costantin Mara B. , Ferreira Marcelo J. P. , Rodrigues Gilberto V. , Emerenciano Vicente P.
Published: March 2019

This paper describes a new module of the expert system SISTEMAT used for the prediction of the skeletons of neolignans by 13C NMR, 1H NMR and botanical data obtained from the literature. SISTEMAT is composed of MACRONO, SISCONST, C13MACH, H1MACH and SISOCBOT programs, each analyzing data of the neolignan in question to predict the carbon skeleton of the compound. From these results, the global probability is computed and the most probable skeleton predicted. SISTEMAT predicted the skeletons of 75% of the 20 neolignans tested, in a rapid and simple procedure demonstrating its advantage for the structural elucidation of new compounds.
New Improvements in Automatic Structure Elucidation Using the LSD (Logic for Structure Determination) and the SISTEMAT Expert Systems
Authors: Plainchont Bertrand , Nuzillard Jean-Marc , Rodrigues Gilberto V. , Ferreira Marcelo J. P. , Scotti Marcus T. , Emerenciano Vicente P.
Published: March 2019

This article describes the integration of the LSD (Logic for Structure Determination) and SISTEMAT expert systems that were both designed for the computer-assisted structure elucidation of small organic molecules. A first step has been achieved towards the linking of the SISTEMAT database with the LSD structure generator. The skeletal descriptions found by the SISTEMAT programs are now easily transferred to LSD as substructural constraints. Examples of the synergy between these expert systems are given for recently reported natural products.
A New ent-Labdane Diterpene Glycoside from the Leaves of Casearia sylvestris
Authors: Wang Wei , Ali Zulfiqar , Li Xing-Cong , Khan Ikhlas A.
Published: March 2019

Sylvestin (1), a new ent-labdane glycoside, was isolated from the leaves of Casearia sylvestris. The structure was determined on the basis of 1D and 2 D NMR and HR-ESI-MS analyses.
Preliminary Investigation of Naringenin Hydroxylation with Recombinant E. coli Expressing Plant Flavonoid Hydroxylation Gene
Authors: Amor Ilef Limem-Ben , Salem Nidhal , Guedon Emmanuel , Engasser Jean-Marc , Chekir-Ghedrira Leila , Ghoul Mohamed
Published: March 2019

Flavonoid hydroxylation is one way to increase the biological activities of these molecules and the number of hydroxyl groups needed for polymerization, esterification, alkylation, glycosylation and acylation reactions. These reactions have been suggested as a promising route to enhance flavonoid solubility and stability. In our preliminary study we hydroxylated naringenin (the first flavonoid core synthesized in plants) with recombinant E. coli harboring flavanone 3 hydroxylase (F3H). We demonstrated that recombinant E. coli harboring the F3H from Petroselinum crispum, can convert naringenin to dihydrokaempferol. The whole cell hydroxylase activity was often influenced by the stability of the plasmid harboring the cloned gene and the biomass yield. When the composition of the growth media became richer the amount of formed product decreased about twofold; the naringenin bioconversion yield in LB media was 70% and decreased to 33% in TB. However, the enrichment of culture media increased the biomass yield nearly threefold in LB media, only 0.5 g/L of bacteria was formed, but in TB there was 1.6 g/L. Thus, LB constitutes the best medium for naringenin bioconversion using the recombinant E. coli harboring the F3H; this allows for maximum bioconversion yield and plasmid stability when compared with the fourth tested culture medium. Consequently, E. coli harboring F3H from Petroselinum crispum can be used to produce flavonoids hydroxylated in position 3 that can serve in additional reactions like polymerization, glycosylation, and acylation,
Rapid Analysis of the Main Components of the Total Glycosides of Ranunculus japonicus by UPLC/Q-TOF-MS
Authors: Rui Wen , Chen Hongyuan , Tan Yuzhi , Zhong Yanmei , Feng Yifan
Published: March 2019

A rapid method for the analysis of the main components of the total glycosides of Ranunculus japonicus (TGOR) was developed using ultra-performance liquid chromatography with quadrupole-time-of-flight mass spectrometry (UPLC/Q-TOF-MS). The separation analysis was performed on a Waters Acquity UPLC system and the accurate mass of molecules and their fragment ions were determined by Q-TOF MS. Twenty compounds, including lactone glycosides, flavonoid glycosides and flavonoid aglycones, were identified and tentatively deduced on the basis of their elemental compositions, MS/MS data and relevant literature. The results demonstrated that lactone glycosides and flavonoids were the main constituents of TGOR. Furthermore, an effective and rapid pattern was established allowing for the comprehensive and systematic characterization of the complex samples.
Pharmacokinetic Comparison in Rats of Six Bioactive Compounds between Da-Cheng-Qi Decoction and its Parent Herbal Medicines
Authors: Xu Fengguo , Liu Ying , Dong Haijuan , Song Rui , Zhang Zunjian
Published: March 2019

Da-Cheng-Qi decoction (DCQD) is a purgative compound prescription used in China and East Asia. In this paper, pharmacokinetic differences of six major active components (rhein, emodin, aloe-emodin, magnolol, naringenin and hesperetin) between DCQD and its three constitutional herbal medicines i.e. Radix et Rhizoma Rhei, Cortex Magnoliae officinalis and Fructus Aurantii Immaturus were investigated in rats after oral administration. Plasma samples were analyzed for the quantification of the six active components using validated LC-MS/MS methods. Unpaired Student's t-test was used for statistical comparison. Significant differences ( p<0.05) in the main pharmacokinetic parameters for rhein, emodin, aloe-emodin, magnolol, naringenin and hesperetin were found between DCQD and the decoction of its constitutional single herbal medicines, which demonstrated the presence of drug-drug interactions between these constitutional raw materials of DCQD occurring either in the procedure of decoction or during ADME process.