bluuebunny/crossref_metadata_2025 huggingface dataset:
Composition of Seed Essential Oils of Rhododendron tomentosum
Authors: Judzentiene Asta , Butkiene Rita , Budiene Jurga , Tomi Félix , Casanova Joseph
Published: March 2019

For the first time, the chemical composition of the seed essential oil of Rhododendron tomentosum was determined. Forty-seven compounds were identified, comprising 91.7% of the total oil. Palustrol (38.3%) and ledol (27.0%) were the predominant constituents. Some constituents, such as β-pinene oxide, iso-menthyl acetate, nerolidyl acetate, cadalene and guaiazulene were characteristic only for the seeds and were identified for the first time in Rh. tomentosum oils. For comparison purposes, the essential oil isolated from the shoots of the same plant were analyzed [GC(FID) in combination with RIs, GC-MS and 13C NMR]. More than a half of the oil was comprised of ledol (36.5%) and palustrol (21.0%). Quantitative analysis of ascaridol, a heat-sensitive compound, was carried out by 13C NMR spectroscopy. Indeed, ascaridol undergoes partial thermal isomerization to iso-ascaridol during GC analyses.
Essential Oil Composition of Cachrys cristata – a rare and Endangered Species in the Flora of Serbia
Authors: Matejić Jelena S. , Džamić Ana M. , Ristić Mihailo S. , Ranđelović Vladimir N. , Marin Petar D.
Published: March 2019

Cachrys cristata DC. (Apiaceace) is a rare and critically endangered species in the flora of Serbia. Essential oil isolated by hydrodistillation from the aerial parts and fruits of this species was analyzed using combined GC and GC/MS. The oil from the aerial parts was rich in sesquiterpenes (45.7%) and oxygenated sesquiterpenes (32.9%), while the fruit oil consisted of a higher percentage of sesquiterpenes (48.3%) and oxygenated sesquiterpenes (36.7%). The dominant constituents in the oil from aerial parts were phytol (13.1%) and germacrene D (12.9%), while in the fruit oil suberosin (19.7%) and germacrene D (12.3%) were the most abundant.
In vitro Inhibitory Activity of Essential Oil Vapors against Ascosphaera apis
Authors: Kloucek Pavel , Smid Jakub , Flesar Jaroslav , Havlik Jaroslav , Titera Dalibor , Rada Vojtech , Drabek Ondrej , Kokoska Ladislav
Published: March 2019

This work evaluates the in vitro inhibitory activity of 70 essential oils (EOs) in the vapor phase for the control of Chalkbrood disease caused by Ascosphaera apis Maassen ex Claussen (Olive et Spiltoir). Two wild strains isolated from infected honey bee colonies together with one standard collection strain were tested by the microatmosphere method. From 70 EOs, 39 exhibited an antifungal effect against A. apis standard and wild strains. The greatest antifungal action was observed for EO vapors from Armoracia rusticana, followed by Thymus vulgaris, Cymbopogon flexosus, Origanum vulgare and Allium sativum. An investigation of chemical composition by GC-MS revealed, that the most active EOs contained allyl isothiocyanate, citral, carvacrol and diallyl sulfides as the main constituents. The chemical composition plays a key role, as activities of different EOs from the same botanical species were different according to their composition.
Chemical Composition and Insecticidal Activity of the Essential Oil of Artemisia eriopoda against Maize Weevil, Sitophilus zeamais
Authors: Jiang Guo Hua , Liu Quan Ru , Chu Sha Sha , Liu Zhi Long
Published: March 2019

In our screening program for new agrochemicals from local wild plants, Artemisia eriopoda was found to possess insecticidal activities against the maize weevil, Sitophilus zeamais. The essential oil of the aerial parts of A. eriopoda was obtained by hydrodistillation and investigated by GC and GC-MS. The main components of the essential oil are germacrene D (21.6%) and eucalyptol (14.2%). The essential oil possesses fumigant toxicity against S. zeamais adults with a LC50 value of 11.5 mg/L air and also shows contact toxicity against S. zeamais adults with a LD50 value of 24.8 μg/adult, respectively.
Efficient Preparation of Incensole and Incensole Acetate, and Quantification of These Bioactive Diterpenes in Boswellia papyrifera by a RP-DAD-HPLC Method
Authors: Paul Michael , Jauch Johann
Published: March 2019

Incensole and incensole acetate, found in incense, are encouraging potent bioactive diterpenic cembrenoids, inhibiting Nuclear Factor-κB activation. Furthermore, incensole acetate elicits psycho-activity in mice by activating the TRPV3 channels in the brain. Starting from crude extracts of the incense species Boswellia papyrifera Hochst., a convenient procedure for the efficient large-scale synthesis of incensole and its acetate is presented. Additionally, a reversed-phase, diode-array-detection, high-performance liquid chromatography (RP-DAD-HPLC) method for the quantification of incensole and incensole acetate is reported, indicating that these two compounds are typical biomarkers for B. papyrifera.
Two New Antimicrobial Metabolites from the Endophytic Fungus, Seimatosporium sp
Authors: Hussain Hidayat , Krohn Karsten , Schulz Barbara , Draeger Siegfried , Nazir Mamona , Saleem Muhammad
Published: March 2019

Two new acaranoic acids, named seimatoporic acid A and B (1, and 2), together with six known compounds, R-(-)-mellein (3), cis-4-hydroxymellein (4), trans-4-hydroxymellein (5), 4R-hydroxy-5-methylmellein (6), (-)-5-hydroxymethylmellein (7), and ergosterol (8) were isolated from an endophytic fungus, Seimatosporium sp, by a bioassay-guided procedure. The structures of the new compounds have been assigned from analysis of the 1H and 13C NMR spectra, DEPT, and by 2D COSY, HMQC, HMBC and NOESY experiments. A mixture of compounds 1 and 2 showed strong antifungal activity against Botrytis cinerea, Septoria tritici, and Pyricularia oryzae.
A Quinoline Based bis-Urea Receptor for Anions: A Selective Receptor for Hydrogen Sulfate
Authors: Russ Tiffany H. , Pramanik Avijit , Khansari Maryam E. , Wong Bryan M. , Hossain Alamgir
Published: March 2019

A dipodal bis-urea receptor has been synthesized from the reaction of 8-amino quinoline and 1,4-phenylene diisocyanate in dichloromethane, and the anion binding ability of the receptor has been studied using fluoride, chloride, bromide, iodide, perchlorate, nitrate, dihydrogen phosphate and hydrogen sulfate by UV-Vis titrations in DMSO. The results show that the receptor binds each of the anions with a 1:1 stoichiometry, showing high affinity and moderate selectivity for hydrogen sulfate among the anions studied. Ab initio calculations based on density functional theory (DFT) suggest that an anion (X-) is bonded within the cleft formed by the two arms of the receptor through two NH…X- and two aromatic CH…X- interactions. The results from solution and theoretical studies suggest that binding is predominantly influenced by hydrogen bonding interactions and the basicity of anions.
Transformations of Griseofulvin in Strong Acidic Conditions – Crystal Structures of 2′-Demethylgriseofulvin and Dimerized Griseofulvin
Authors: Lesniewska Barbara , Jebors Said , Coleman Anthony W. , Suwińska Kinga
Published: March 2019

The structure of griseofulvic acid, C16H15ClO6, at 100 K has orthorhombic (P21212) symmetry. It is of interest with respect to biological activity. The structure displays intermolecular O–H···O, C–H···O hydrogen bonding as well as week C–H···π and π ···π interactions. In strong acidic conditions the griseofulvin undergoes dimerization. The structure of dimerized griseofulvin, C34H32Cl2O12·C2H6O·H2O, at 100 K has monoclinic (P21) symmetry. The molecule crystallized as a solvate with one ethanol and one water molecule. The dimeric molecules form intermolecular O–H···O hydrogen bonds to solvents molecules only but they interact via week C–H···O, C–H···π, C–Cl···π and π···π interactions with other dimerized molecules.
Toward Engineering Intra-Receptor Interactions into Bis(crown ethers)
Authors: Krause Martin R. , Kubik Stefan
Published: March 2019

A synthetic receptor was designed in which cooperative binding of two crown ether moieties to an alkali metal ion simultaneously causes two hydrophobic substituents not involved in direct host-guest interactions to converge. Hydrophobic interactions between these substituents can be expected to contribute to the overall complex stability. Independent binding studies involving two diastereoisomers of this bis(crown ether), one in which intra-receptor interactions between the substituents are potentially possible and one in which they are not, using isothermal titration calorimetry showed that both isomers bind potassium ions in different solvent mixtures with the same overall affinity. Profound differences were observed for each isomer, however, in the enthalpies and entropies of binding, which are consistent with intra-receptor interactions in one compound. These interactions are counteracted by enthalpy-entropy compensation so that no overall improvement in cation affinity could be observed.
Sulfur and Sulfur Compounds in Plant Defence
Authors: Nwachukwu Ifeanyi D. , Slusarenko Alan J. , Gruhlke Martin C. H.
Published: March 2019

The multiplicity of chemical structures of sulfur containing compounds, influenced in part by the element's several oxidation states, directly results in diverse modes of action for sulfur-containing natural products synthesized as secondary metabolites in plants. Sulfur-containing natural products constitute a formidable wall of defence against a wide range of pathogens and pests. Steady progress in the development of new technologies have advanced research in this area, helping to uncover the role of such important plant defence molecules like endogenously-released elemental sulphur, but also deepening current understanding of other better-studied compounds like the glucosinolates. As studies continue in this area, it is becoming increasingly evident that sulfur and sulfur compounds play far more important roles in plant defence than perhaps previously suspected.
Stereoselective Synthesis of Bicyclo[3.1.1]Heptane Derivatives via Intramolecular Photocycloaddition Reaction
Authors: Honda Kiyoshi , Konishi Mari , Kawai Manabu , Yamada Akihisa , Takahashi Yasuhiko , Hoshino Yujiro , Inoue Seiichi
Published: March 2019

Optically active 1,3-bridged cyclobutanes 10 of the bicyclo[3.1.1]heptane ring system and 1,2-bridged cyclobutanes 11 of the bicyclo[3.2.0]heptane ring system were produced by UV irradiation of α,β,γ,δ-unsaturated esters 9a and 9c-f. The preference of endo-stereochemistry at C-6 bridged head was observed in cross-adducts 10. On the other hand, irradiation of conjugated dienol9b led via only parallel cycloaddition to 1,2-bridged cyclobutane 11.
Acaricidal and Repellent Activity of Terpenoids from Seaweeds Collected in Pernambuco, Brazil
Authors: Born Flávia Souza , Bianco Éverson Miguel , da Camara Claudio Augusto Gomes
Published: March 2019

n-Hexane and dichloromethane extracts obtained from Laurencia dentroidea (Rhodophyta) and Canistrocarpus cervicornis (Phaeophyta) were investigated for their acaricidal and repellent properties against Tetranychus urticae under laboratory conditions. The two extracts displayed moderate toxicity and good repellent proprieties, and were significantly more toxic (36-fold) than the positive control (eugenol), whereas eugenol was tenfold more repellent than either seaweed extract. The sesquiterpenoid elatol (1) was isolated from L. dentroidea and the diterpenoid seco-dolastane (4 R,9 S,14 S)-4α-acetoxy-9β,14α-dihydroxydolast-1(15),7-diene (2) from C. cervicornis, the chemical structures of which were characterized by NMR spectroscopic data (1H and 13C) and by comparison with literature data. These compounds exhibited moderate toxicity, but a high degree of repellent activity against T. urticae. The findings suggest that marine natural products, specifically terpenes, can be employed for the development of new pesticides and become prototype agrochemical agents.
Chemical Constituents of the Aerial Parts of Scutellaria lateriflora and their α-Glucosidase Inhibitory Activities
Authors: Kuroda Minpei , Iwabuchi Katsura , Mimaki Yoshihiro
Published: March 2019

MeOH extracts of 37 herbs were tested in screening experiments for rat intestinal α-glucosidase. The MeOH extract of the aerial parts of Scutellaria lateriflora L. (Lamiaceae) significantly inhibited sucrase and maltase activities, using sucrose and maltase as the substrates. Enzyme inhibition guided-fractionation of the MeOH extract of S lateriflora resulted in the isolation of a new diterpene glucoside, deacetylajugarin-IV 18- O-β-D-glucopyranoside (1), along with 20 known phenolics (2-21). The structures of 1-21 were elucidated on the basis of MS and NMR data analyses. Baicalein (4) and baicalin (10), a glycoside of 4, showed moderate sucrase inhibitory activities at IC50 values of 14.9 and 36.3 μM, respectively, whereas luteolin (3), acteoside (16), leucosceptoside A (18), and isoacteoside (20) showed weak inhibitory activities at IC50 values of 811, 522, 727, and 443 μM, respectively. This is the first report on mammalian α-glucosidase inhibitory activities of S lateriflora extract and identification of the constituents responsible for the activities. Apigenin (2), luteolin (3), 6-methoxyluteolin 4'-methyl ether (6), isoscutellarin 8- O-β-D-glucuronide (7), luteolin 7- O-β-D-glucuronide (9), wogonin 7- O-β-D-glucuronide methyl ester (12), eriodictyol (13), naringenin (14), naringenin 7- O-β-D-glucuronide (15), jionoside D (17), leucosceptoside A (18), and (+)-syringaresinol 4'- O-β-D-glucopyranoside (21) were isolated from this plant for the first time. The inhibitory properties of S lateriflora extract against α-glucosidase provide a prospect for its antidiabetic usage.
Phorbol Esters with Wnt Signal-Augmenting Effects Isolated from Excoecaria Indica
Authors: Yamaguchi Tatsuhiro , Toume Kazufumi , Arai Midori A. , Ahmed Firoj , Sadhu Samir K. , Ishibashi Masami
Published: March 2019

A screening of natural products using a luciferase assay targeting the Wnt signaling pathway was carried out, and the bioassay-guided fractionation of Excoecaria indica (Euphorbiaceae) collected from Bangladesh afforded three phorbol esters (1 – 3). These compounds exhibited Wnt signal-augmenting effects with 1 causing a 25-fold increase in TCF/β-catenin (TOP) transcriptional activity at 95 nM.
Triangulene C, A New Cubitane-Based Diterpenoid from the Soft Coral Sinularia Triangula
Authors: Su Huey-Jen , Lee Nai-Lun , Lu Mei-Chin , Su Jui-Hsin
Published: March 2019

A new cubitane-based diterpenoid, triangulene C (1), was isolated from the soft coral Sinularia triangula and its structure was elucidated on the basis of spectroscopic data. Compound 1 was not cytotoxic (IC50 >20 μg/mL) toward the four human cancer cell lines tested (HL60, MDA-MB-231, HCT-116 and DLD-1).
Cladieunicellin H, a New Hemiketal Eunicellin-Based Diterpenoid from the Octocoral Cladiella sp
Authors: Chen Yung-Husan , Tai Chia-Ying , Hwang Tsong-Long , Sung Ping-Jyun
Published: March 2019

A new hemiketal eunicellin-based diterpenoid, cladieunicellin H (1), was isolated from an Indonesian octocoral identified as Cladiella sp. The structure of 1 was determined by spectroscopic methods. This compound was found to display moderate inhibitory effects on the generation of superoxide anion and the release of elastase by human neutrophils.
A New Geranylated Aromatic Compound from the Mushroom Hericium Erinaceum
Authors: Yaoita Yasunori , Yonezawa Shiori , Kikuchi Masao , Machida Koichi
Published: March 2019

A new geranylated aromatic compound, 5-[(2′ E)-3′,7′-dimethyl-2′,6′-octadienyl]-4-hydroxy-6-methoxy-1-isoindolinone (1), was isolated from the fruiting bodies of the mushroom Hericium erinaceum (Bull.: Fr.) Pers. (Hericiaceae) together with three known sterols, 5α,6α-epoxy-(22 E)-ergosta-8(14),22-diene-3β,7α-diol (2), (22 E)-ergosta-7,9(11),22-triene-3β,5α,6β-triol (3) and (22 E)-ergosta-7,22-diene-3β,5α,6α,9α-tetrol (4). The structure of the new compound was elucidated on the basis of spectral data.
Diversity of Furanoeremophilanes in Major Ligularia Species in the Hengduan Mountains
Authors: Kuroda Chiaki , Hanai Ryo , Nagano Hajime , Tori Motoo , Gong Xun
Published: March 2019

The chemical and genetic diversity of Ligularia species in the Hengduan Mountains area of China is reviewed. A hypothesis that the production of furanoeremophilanes is ecologically advantageous is proposed.
Iridoid and Phenolic Glycosides from the Roots of Prismatomeris connata
Authors: Feng Shixiu , Bai Jijiang , Qiu(Samuel) Shengxiang , Li Yong , Chen Tao
Published: March 2019

A new phenolic glycoside, 1- O-[β-D-glucopyranoyl-(1→6)-β-D-glucopyranosyl]-3,4,5-trimethoxyphenol, named prismaconnatoside (1), together with one known phenolic glycoside (2) and four aspruloside type iridoid glycosides (3-6) were isolated from the roots of Prismatomeris connata. Their structures were determined by spectroscopic and spectrometric methods. Based on the results, along with those from other studies, iridoids were suggested to be chemical markers to distinguish between P. connata and P. tetrandra, two species that are confused in traditional Chinese medicine.
Phytochemical and Biological Activity Studies of the Bhutanese Medicinal Plant Corydalis crispa
Authors: Wangchuk Phurpa , Keller Paul A. , Pyne Stephen G. , Sastraruji Thanapat , Taweechotipatr Malai , Rattanajak Roonglawan , Tonsomboon Aunchalee , Kamchonwongpaisan Sumalee
Published: March 2019

The chemical constituents and biological activities of Corydalis crispa (Fumariaceae) were investigated for the first time. The phytochemical study resulted in the isolation of nine known isoquinoline alkaloids: protopine (1), 13-oxoprotopine (2), 13-oxocryptopine (3), stylopine (4), coreximine (5), rheagenine (6), ochrobirine (7), sibiricine (8) and bicuculline (9), with complete NMR data for 2 and 3 provided here for the first time. Crude extracts exhibited significant anti-inflammatory (p<0.01) activity against TNF- α production in LPS activated THP-1 cells. The acetylcholinesterase inhibitory activity of compounds 2, 4 and 7 and the antiplasmodial activity of compound 5 against P. falciparum strains TM4/8.2 and K1CB1 (multidrug resistant strain) are reported here for the first time. Stylopine (4) did not show antimalarial activity against the K1CB1 strain in contrast to a previous report. This study generated a scientific basis for the use of this plant in Bhutanese traditional medicine, either individually or in combination with other medicinal ingredients to treat a broad range of disorders. This study also identified compound 5 as potential new antimalarial lead compound.
On the Biosynthetic Pathway of Papaverine via (S)-Reticuline – Theoretical vs. Experimental Study
Authors: Ivanova Bojidarka , Spiteller Michael
Published: March 2019

The electronic structures, optical properties and molecular structures of a series of isoquinoline alkaloids resulting in the formation of papaverine, through a proposed biosynthetic pathway via S(+)-reticuline were elucidated. The mechanism of papaverine synthesis was studied by electronic absorption, diffuse reflectance, fluorescence and CD spectroscopy, as well as ESI and MALDI Orbitrap imaging mass spectrometry. Quantum chemical DFT calculations in the gas phase and solution were performed with a view to study the electronic transitions of the interacting species, corresponding proposed intermediates, and the expected mass spectrometric fragments. The complete study and understanding of the mechanism of the biosynthetic pathway in the poppy plants appears important for the functional oriented drug-design and synthesis of corresponding structurally related alkaloids.
Secondary Metabolites from Polar Fractions of Piper umbellatum
Authors: Tabopda Turibio Kuiate , Mitaine-Offer Anne-Claire , Miyamoto Tomofumi , Tanaka Chiaki , Ngadjui Bonaventure Tchaleu , Lacaille-Dubois Marie-Aleth
Published: March 2019

Seven known secondary metabolites were isolated from the methanol extract of the branches of Piper umbellatum. The identification of these compounds was mainly achieved by 2D NMR spectroscopic techniques and FAB-MS. Among them, the known cepharadiones A and B can be considered as chemotaxonomic markers of the genus Piper.
A New Antimycobacterial Furanolignan from Leucophyllum frutescens
Authors: Alanís-Garza Blanca , Salazar-Aranda Ricardo , Ramírez-Durón Rosalba , Garza-González Elvira , de Torres Noemí Waksman
Published: March 2019

Bioassay-guided fractionation of the minor active fractions obtained from the root bark of Leucophyllum frutescens (Berl.) I. M. Johnst. led to isolation from the n-hexane extract of a new compound with moderate activity against the H37Rv Mycobacterium tuberculosis strain (MIC 63 μg/mL), and low cytotoxicity, as shown by the IC50 against Vero cells. The compound was identified by 1D/2D NMR spectroscopy as 2′,5″-dimethoxysesamin.
Lichen Depsides and Depsidones Reduce Symptoms of Diseases Caused by Tobacco Mosaic Virus (TMV) in Tobacco Leaves
Authors: Ramírez Ingrid , Araya Soledad , Piovano Marisa , Carvajal Marcela , Cuadros-Inostroza Alvaro , Espinoza Luis , Garbarino Juan Antonio , Peña-Cortés Hugo
Published: March 2019

Two depsides and five depsidones, isolated from lichens, were tested to determine their in vivo protective effects on tobacco leaves challenged with Tobacco Mosaic Virus (TMV). The results indicate that most of these compounds are able to reduce either the number and/or the size of necrotic lesions following virus infection. Pannarin, 1′-chloro-pannarin and stictic acid provided the more effective protective results, reducing by at least 45% the number and size of lesions. Real Time PCR assays were used to explore the target of action against TMV by examining the response behavior of genes involved in the plant defense mechanism. The application of the lichen substances did not lead to changes in the transcriptional levels of pathogen-related ( PR1a), allene oxide synthase 2 ( AOS2) or oxophytodienoate reductase ( OPR3) genes. Thus, the protection observed in the tobacco leaves treated with the lichen compounds may be mediated by a mechanism which does not involved the SA- or JA-mediated defensive plant response. A possible structure-activity relationship is presented.
The Origin of Virgin Argan Oil's High Oxidative Stability Unraveled
Authors: Gharby Saïd , Harhar Hicham , Guillaume Dominique , Haddad Aziza , Charrouf Zoubida
Published: March 2019

To prepare either virgin edible or beauty argan oil, roasted or unroasted argan kernels are cold-pressed, respectively. Comparing the physicochemical parameters of edible and beauty argan oil immediately after preparation and after a two-year delay has led to the suggestion that phospholipids are a new and essential type of oil component participating in the excellent oxidative stability of edible argan oil, in addition to the already suggested Maillard-reaction products, phenols, and tocopherols.
Chemical Composition of Essential Oils from a Multiple Shoot Culture of Telekia speciosa and Different Plant Organs
Authors: Wajs-Bonikowska Anna , Stojakowska Anna , Kalemba Danuta
Published: March 2019

The composition of essential oil from Telekia speciosa leaves, flowers, roots, stems and in vitro regenerated shoots was studied by GC-MS-FID leading to the determination of 112 compounds. The qualitative composition of the essential oil from the examined plant material was similar, whereas quantities of individual components of the oils varied widely depending on the kind of plant material. The most striking differences were observed between the oils produced by aerial and underground parts of the intact plant, as well as between oils produced by in vitro grown shoots and leaves of the intact plant. The main volatiles of leaf essential oil were: ( E, E)-farnesol (21.2%) and ( E)-nerolidol (17.9%), while isoalantolactone was the predominant component of the root (62.3%) and flower oils (23.0%). Numerous thymol derivatives were also found, among them 10-isobutyryloxy-8,9-epoxythymol isobutyrate, which was one of the main components found in the flower oil (20.5%) and that from the in vitro cultures (20.2%).
Volatiles from Michelia champaca Flower: Comparative analysis by Simultaneous Distillation-Extraction and Solid Phase Microextraction
Authors: Báez Disnelys , Morales Diego , Pino Jorge A.
Published: March 2019

The chemical composition of the volatile compounds isolated by simultaneous distillation-extraction (SDE) and headspace-solid phase microextraction (SPME) from flowers of Michelia champaca growing in Cuba was investigated by GC/FID and GC/MS. Sixty-seven and thirty-four components were identified by SDE and SPME, respectively, with 1,8-cineole (22.8%) as the main constituent in the volatile oil isolated by SDE, and methyl benzoate (30.3%), indole (16.6%) and β-elemene (10.4%) the major components detected by SPME.
Constituents and Antimicrobial Activity of the Essential Oils from Flower, Leaf and Stem of Helichrysum armenium
Authors: Oji Khodam-Ali , Shafaghat Ali
Published: March 2019

The chemical constituents from the flower, leaf and stem of Helichrysum armenium DC. (Asteraceae) growing in Iran were obtained by hydrodistillation and analyzed by GC and GC/MS. The oil of flower was characterized by higher amount of limonene (21.2%), α-cadinol (18.2%), borneol (11.9%), δ-cadinene (9.0%), bornyl acetate (8.0%) and α-humulene (7.3%). Twenty one constituents representing 96.2% of the chromatographical leaf oil were identified of which limonene (29.2%), α- pinene (14.4%), caryophyllene oxide (6.5%), α-gurjunene (6.3%), bornyl acetate (5.5%) and torreyol (5.2%) were the major components. The main components of the stem oil were limonene (23.6%), α-pinene (13.4%), spathulenol (6.4%), α-gurjunene (6.3%), caryophyllene oxide (5.3%), bornyl acetate (5.2%), β-cubebene (4.8%) and δ-cadinene (4.3%). The composition of the oils is different, although the most abundant components are identical in leaf oil (96.2%). The antimicrobial effect of flower, leaf and stem essential oils from Helichrysum armenium was studied according to the agar diffusion cup method. The essential oils had a moderate effect on the Gram-positive and Gram-negative bacteria and had a substantial fungicidal effect on the fungi under study.
Plant Essential Oils and Mastitis Disease: Their Potential Inhibitory Effects on Pro-inflammatory Cytokine Production in Response to Bacteria Related Inflammation
Authors: Taga Ibrahim , Lan Christopher Q. , Altosaar Illimar
Published: March 2019

This paper highlights the role of plant volatile organic compounds, found in essential oils, for the treatment of bacteria related inflammation. This report is focused on tea tree oil, particularly its main compound terpinen-4-ol. Analysis of the published literature shows that many essential oils have significant antibacterial, antifungal and anti-inflammatory effects. Some of their major components, such as terpinen-4-ol, act by inhibiting pro-inflammatory cytokine expression while stimulating production of anti-inflammatory cytokines. Such observations may be exploited to encourage biotherapy against mastitis. The use of synthetic antibiotics is being increasingly discouraged because their presence in dairy milk may have potential downstream effects on population health and the agri-food chain. In the context of inflammation and related mammalian responses, understanding the interplay between volatile organic compounds, especially terpinen-4-ol, and cytokines during bacteria related inflammation should clarify their mode of action to control mastitis.
Distribution of Drimane Sesquiterpenoids and Tocopherols in Liverworts, Ferns and Higher Plants: Polygonaceae, Canellaceae and Winteraceae Species
Authors: Asakawa Yoshinori , Ludwiczuk Agnieszka , Harinantenaina Liva , Toyota Masao , Nishiki Mayumi , Bardon Alicia , Nii Kaeko
Published: March 2019

The liverwort, Porella vernicosa complex produces a very hot tasting polygodial, a drimane-type sesquiterpene dialdehyde. The same compound has been isolated from two ferns, Thelypteris hispidula and Blechnum fluviatile, as well as from the higher plants Polygonum hydropiper, P. hydropiper f purpurascens (Polygonaceae), Cinnamosma, Caspicodendron, Canella and Warburgia species (Canellaceae), and Pseudowintera colorata, Tasmannia lanceolata, Drimys and Zygogynum species (Winteraceae). In addition, the liverworts and higher plants which elaborate polygodial and its related pungent drimane dials contain a small amount of α-tocopherol, γ-tocopherol or δ-tocotrienol. The present paper gives the results of a comparative study on the drimane-type sesquiterpenoids in some liverworts, ferns and higher plants, and the role of tocopherols in these plant groups.
Unusual Reactions of a 7,17-seco-type C19-Diterpenoid Alkaloid Derived from Deltaline
Authors: Wang Ling , Chen Qiao-Hong , Wang Feng-Peng
Published: March 2019

Treatment of a 7,17- seco-type C19-diterpenoid alkaloid (3), prepared from deltaline (8), with triethylamine in either DMF or TEG (triethylene glycol) at 120°C provided two interesting compounds 6 and 7. The structures of compounds 3, 6, and 7 were established based on extensive interpretations of their 1D and 2D NMR data. Compound 6, a lycoctonine-type C19-diterpenoid alkaloid, can be transformed from alkaloid 3 via Grob fragmentation, Prins reaction, and intramolecular disproportionation. The mechanism of the formation of compound 6 was confirmed by deuteration experiments. Product 7 was formed through a pinacol-like rearrangement of alkaloid 3.
Determination of the Absolute Configuration of 19-OH-(-)-Eburnamonine Using a Combination of Residual Dipolar Couplings, DFT Chemical Shift Predictions, and Chiroptics
Authors: Trigo-Mouriño Pablo , Sifuentes Roxana , Navarro-Vázquez Armando , Gayathri Chakicherla , Maruenda Helena , Gil Roberto R.
Published: March 2019

19-OH-(-)-eburnamonine 1 is a new indole alkaloid isolated from Bonafusia macrocalyx. A natural derivative from (-)-eburnamonine for which absolute configuration and conformation has been determined by making use of residual dipolar couplings enhanced NMR, circular dichroism spectra and high-level computations.
Cinnamoylphenethyl Amides from Polygonum hyrcanicum Possess Anti-Trypanosomal Activity
Authors: Moradi-Afrapoli Fahimeh , Yassa Nargues , Zimmermann Stefanie , Saeidnia Soodabeh , Hadjiakhoondi Abbas , Ebrahimi Samad N. , Hamburger Matthias
Published: March 2019

A methanolic extract from aerial parts of Polygonum hyrcanicum (Polygonaceae) showed high activity against Trypanosoma brucei rhodesiense (IC50=3.7 μg/mL). Bioassay-guided fractionation of the extract resulted in isolation of cinnamoylphenethyl amides, including N-trans-caffeoyltyramine (1), N-trans-p-coumaroyltyramine (7), and N-trans-feruloyltyramine (8) as the main active constituents (IC50s ranging from 2.2 to 13.3 μM). Some structurally related, but less active compounds, such as cannabisin B (2), tyrosol (3), p-coumaric acid (4), ferulic acid (5), and N-cis-feruloyltyramine (6) were also identified, along with N-trans-3,4-dimethoxycinnamoyldopamine (9). Cytotoxicity of the active compounds in L6 cells was determined, and selectivity indices (SI) of 7.9 to 33.4 were calculated.
Comparative Study of the in vitro Bioactivities of Bupleurum rigidum and B. fruticescens
Authors: Prieto Jose M. , Ogunsina Makanjuola O. , Novak Andrea , Joshi Amit , Kokai Judit , Rocha Ines Da Costa , de Santayana Manuel Pardo
Published: March 2019

Decoctions of the aerial parts of either Bupleurum rigidum or B. fruticescens are equally used in certain parts of Spain for the treatment of topical and musculoskeletal inflammations. In the present paper, their phytochemical profile and pharmacological value has been compared. After chromatographic and spectral analyses we could establish the presence of rutin and absence of chlorogenic acid in B. fruticescens, whilst the contrary applies to B. rigidum, providing a means to chemically differentiate extracts and dry materials from the two species. Their free radical scavenging and antiperoxidative activities were similar, with B. fruticescens being more active overall. The infusions of both Bupleurum species also showed similar anti-inflammatory activity when tested by NF-κB assay (40% and 42% at 60 μg·mL−1), as well as in a hexosaminidase exocytosis assay (30% at 50 μg·mL−1). Antimigratory effects on rat melanoma B16F10 showed significant activity for both infusions, with B. rigidum twice as potent as B. fruticescens, the activity of the latter not being fully explained by its content of rutin. Taking all these results together, we can conclude that, in the selected experimental models, there exist an in vitro bioequivalence of the infusions from both species, which is in agreement with the majority of ethnopharmacological reports.
Saracoside: A New Lignan Glycoside from Saraca indica, a Potential Inhibitor of DNA Topoisomerase IB
Authors: Mukherjee Tulika , Chowdhury Sayan , Kumar Ashish , Majumder Hemanta K , Jaisankar Parasuraman , Mukhopadhyay Sibabrata
Published: March 2019

Chemical investigation of the stem bark of Saraca indica has resulted in the isolation of a new lignan glycoside, saracoside, along with four known lignan glycosides lyoniside, icariside E3, (+)5′methoxyisolarciresinol-9′- O-β-D-glucopyranoside and nudiposide, and a phenolic glucopyranoside, 3,4,5– trimethoxyphenyl-β-D-glucopyranoside, which has been isolated for the first time from this species. The isolated lignan glycosides exhibit potent DNA topoisomerase IB inhibitory activity.
Phenylethanoid Glycosides Isolated from Paraboea Paniculata
Authors: Yue Tan Hor , Hock Anthony Ho Siong , Kiang Lim Chan , Mooi Lim Yang
Published: March 2019

Phytochemical studies of the leaves and rhizomes of Paraboea pa niculata (Gesneriaceae) are reported for the first time. Three phenylethanoid glycosides were isolated and characterized as 3,4-dihydroxyphenethyl-(3″- O-β-D-apiofuranosyl)- β-D-glucopyranoside, calceoralarioside E, and acteoside. These isolates exhibited weak cytotoxic activity against the K-562 cell line with a 50% of cell killing rate of 40.18 μM, 27.05 μM, and 27.24 μM, respectively. In the DPPH free radical scavenging assay, their IC50 values were determined as 75.89 μM, 25.00 μM, and 26.04 μM, respectively.
Villarinol, a new Alkenoyloxyalkenol Derivative from the Endemic Philippine Rubiaceae species Villaria odorata
Authors: Macabeo Allan Patrick G. , Avila Jalil A. , Alejandro Grecebio Jonathan D. , Franzblau Scott G. , Kouam Simeon F. , Hussain Hidayat , Krohn Karsten
Published: March 2019

Villarinol (1), a new alkenoyloxy alkenol metabolite, has been isolated from the dichloromethane extract of Villaria odorata, an endemic Rubiaceae Philippine plant, along with the known compounds stigmasterol and 4-hydroxybenzaldehyde. The structure of 1 was elucidated on the basis of spectroscopic and spectrometric studies. The extracts of V. odorata exhibited moderate inhibition against Mycobacterium tuberculosis H37Rv, based on the colorimetric microplate alamar blue assay.
Suppression of Nitric Oxide Synthase by Thienodolin in Lipopolysaccharide-stimulated RAW 264.7 Murine Macrophage Cells
Authors: Park Eun-Jung , Pezzuto John M. , Jang Kyoung Hwa , Nam Sang-Jip , Bucarey Sergio A. , Fenical William
Published: March 2019

The measurement of nitric oxide in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells is used as a model for evaluating the anti-inflammatory or chemopreventive potential of substances. Thienodolin, isolated from a Streptomyces sp. derived from Chilean marine sediment, inhibited nitric oxide production in LPS-stimulated RAW 264.7 cells (IC50 = 17.2 ± 1.2 μM). At both the mRNA and protein levels, inducible nitric oxide synthase (iNOS) was suppressed in a dose-dependent manner. Mitogen-activated protein kinases (MAPKs), one major upstream signaling pathway involved in the transcription of iNOS, were not affected by treatment of thienodolin. However, the compound blocked the degradation of IκBα resulting in inhibition of NF-κB p65 nuclear translocation, and inhibited the phosphorylation of signal transducers and activators of transcription 1 (STAT1) at Tyr701. This study supports further exploration of thienodolin as a potential therapeutic agent with a unique mechanistic activity.
Herbal Medicine in Healthcare-An Overview
Authors: Mosihuzzaman Mohammed
Published: March 2019

It is generally accepted by all concerned that modern pharmaceuticals will remain out of reach of many people and ‘health for all’ may only be realized by the use of adequately assessed herbal products. Mankind has been using herbal medicine for healing right from the beginning of human civilization. With the advent of ‘modern medicine’ herbal products have been looked down upon, especially by western societies. Yet, in recent times, use of herbal medicine for heathcare has increased steadily all over the world. However, serious concerns are being realized regarding the safety, claimed efficacy and quality of herbal products used as herbal medicine, nutraceuticals, health food and cosmetics. Although herbal products are generally considered safe due to their age-old usage, significant side effects have been reported for many herbal products, including herbal medicine. Accidental contamination and intentional adulteration are considered as primary reasons for the side effects. The historical perspective and the philosophy of herbal medical practice along with its present status in the light of present day science have been reviewed and included in the present article. Assurance of safety by identification of contaminants and assessment of toxicity has been outlined. Assessment of claimed efficacy of herbal medicine is difficult due to its holistic approach. Practical ways of assessing efficacy of herbal medicine by adapting the methodologies used for modern pharmaceutical are described. The maintenance of standard of herbal medicine has been stressed and pragmatic approaches of assuring quality of herbal medicine by using modern tools of fingerprinting the chemical profile of herbal medicine are discussed. As much of the traditional herbal medical knowledge is scattered around the world at the family and community levels, and more so in the indigeneous people, the knowledge base is continuously being lost and so needs immediate documentation. Difficulties in documentation due to concerns of Intellectual Property Rights (IPR) have been highlighted.
Chemical Constituents of Blumea balsamifera of Indonesia and Their Protein Tyrosine Phosphatase 1B Inhibitory Activity
Authors: Saifudin Azis , Tanaka Ken , Kadota Shigetoshi , Tezuka Yasuhiro
Published: March 2019

A methanol extract of the leaves of Blumea balsamifera (L.) DC. (Asteraceae) afforded a new guaian-type sesquiterpene, epiblumeaene K (1), together with four known guaian-type sesquiterpenes (2–5), three known sesquiterpenes (6–8), and nine known flavonoids (9–17) by a combination of chromatography and preparative TLC techniques. Their structures were elucidated by extensive spectroscopic methods and comparison with the literature data. Among the isolated compounds, a known sesquiterpene, β-caryophyllene 8 R,9 R-oxide (6), exhibited a significant PTP1B inhibitory activity in a dose-dependent manner, with an IC50 value of 25.8μM (5.62μg/mL).
Compounds with Antiproliferative Activity on Five Human Cancer Cell Lines from South Korean Carpesium triste
Authors: Moon Hyung-In
Published: March 2019

In the search for antiproliferative compounds against human cancer cells (A549, SK-OV-3, SK-MEL-2, XF498, HCT15), it was found that the chloroform extracts obtained from the whole plant of Carpesium rosulatum Miq. (Compositae) exhibited significant cytotoxic activity. Two sesquiterpene lactones, CT-1 (2α,5-epoxy-5,10-dihydroxy-6-angeloyloxy-9β-isobutyloxy-germacran-8α,12-olide), and CT-2 (2β,5-epoxy-5,10-dihydroxy-6α,9β-diangeloyloxy-germacran-8α,12-olide) were isolated from the whole plant. CT-2 showed the most potent cytotoxicity with an IC50 value of 7.88 μM against SK-MEL-2.
Biogenetic-type Synthesis of 2-Hydroxy-4,4,7-trimethyl-1(4H)-naphthalenone, a Modified Apocarotenoid from Ipomoea pes-caprae
Authors: Fondekar Kamalesh P. Pai , Paknikar Shashikumar K. , Torres Savia , Kamat Shrivallabh P.
Published: March 2019

A biogenetic-type synthesis of 2-hydroxy-4,4,7-trimethyl-1(4 H)-naphthalenone (1), a modified apocarotenoid isolated from Ipomoea pes-caprae (Linn.) R. Br. showing anti-inflammatory activity by inhibiting prostaglandin synthesis in vitro, is described. A biogenetic proposal for the natural occurrence of 1 is also presented.
Chemical Investigation of Saponins from Twelve Annual Medicago Species and their Bioassay with the Brine Shrimp Artemia salina
Authors: Tava Aldo , Pecetti Luciano
Published: March 2019

The saponin and sapogenin composition of the aerial growth of 12 annual Medicago species sampled at full senescence were investigated. Saponins were extracted from the plant material and obtained in a highly pure grade by reverse-phase chromatography, with a yield ranging from 0.38 ± 0.04% to 1.35 ± 0.08% dry matter, depending on the species. Sapogenins were then obtained after acid hydrolysis of saponins, and evaluated by GC/FID and GC/MS methods. Different compositions of the aglycone moieties were observed in the 12 Medicago species. Medicagenic acid was the dominant aglycone in M. × blancheana, M. doliata, M. littoralis, M. rotata, M. rugosa, M. scutellata, M. tornata and M. truncatula, bayogenin and hederagenin in M. arabica and M. rigidula, echinocystic acid in M. polymorpha, and soyasapogenol B in M. aculeata. The purified saponin mixtures, characterized by different chemical compositions, were then used in a toxicity test using the brine shrimp Artemia salina. The most active compounds were the saponins from M. arabica and M. rigidula with LD50 values of 10.1 and 4.6 μg/mL, respectively. A structure-activity relationship for the tested saponin mixtures was observed.
Effect of Polyamines on Shoot Multiplication and Furanocoumarin Production in Ruta graveolens Cultures
Authors: Diwan Renuka , Malpathak Nutan
Published: March 2019

The influence of the polyamines putrescine (Put), spermine (Spr) and spermidine (Spd) on growth and furanocoumarin production was investigated by exogenous addition, at different concentrations, to shoot cultures of Ruta graveolens at different phases of growth. Preliminary studies indicated that addition of Put (20 μM) and Spr (80 μM) had a promotive effect on shoot multiplication rate and number of multiple shoots formed. Spd was toxic, even at lower concentrations. The growth-phase of the culture at the time of exogenous addition of polyamines was found to be an important factor. Put was most effective when added at the lag phase, while Spr was most effective when added in the log phase. Time course studies of growth and furanocoumarin content were carried out for each polyamine and phase of addition. It was seen that maximum production of furanocoumarins (256.8 mg/10 g DW) occurred in the second week when Put was added in the lag phase and 260.5 mg/10 g DW in the fourth week when Spr was added in the log phase. Put addition resulted in a 3.10 fold increase in psoralen, 6.12 in xanthotoxin and 1.46 fold in bergapten production. Spr addition resulted in a 1.31 fold increase in psoralen, 4.11 fold in xanthotoxin and 1.49 fold in bergapten production. Results indicate that alteration of growth and furanocoumarin production kinetics is a combined outcome of choice of polyamine and the phase of culture at the time of exogenous addition. Polyamine addition enabled significant enhancement in production of pharmaceutically important bergapten and xanthotoxin in shoot cultures of Ruta graveolens, which could be explored for commercial production.
Drynariae Rhizoma Increases Immune Response in Mice
Authors: An Hyo-Jin , Lee Gil-Goo , Lee Kyung-Tae
Published: March 2019

Drynariae Rhizoma (DR), a traditional Korean herbal medicine, has long been used for vital energy and to strengthen health in Korea. However, it is still unclear how DR has the effects in experimental models. We examined the immune-enhancing effect of DR in mice using the forced swimming test (FST) and in vitro tests with peritoneal macrophages. After daily oral administration of DR, blood biochemical parameters related to fatigue were measured after the FST. The immobility time in the FST was significantly decreased in the DR-treated group (100 mg/kg) on the 3th days. DR (10 and 100 mg/kg) treatment significantly decreased creatine kinase and lactic dehydrogenase levels, which are accurate indicators of muscle damage. Further, we examined how DR regulates nitric oxide (NO) production and tumor necrosis factor alpha (TNF-α) production and in mouse peritoneal macrophages. When DR was used in combination with recombinant interferon-gamma (rIFN-γ), there were noticeable cooperative productions of NO and TNF-α. These results suggest that DR improves immune function through the changes in indicators related to fatigue and the regulatory effects on immunological parameters, such as NO and TNF-α productions.
Search for Bioactive Compounds from Cantharellus cibarius
Authors: Daniewski Włodzimierz Maria , Danikiewicz Witold , Gołębiewski W. Marek , Gucma Mirosław , Łysik Agnieszka , Grodner Jacek , Przybysz Elżbieta
Published: March 2019

Ground fruit bodies of Cantharellus cibarius (chanterelle) were extracted with dichloromethane and subjected to CC followed by preparative HPLC, which led to the isolation of glycerol 1,2- and 1,3-dilinoleates and glycerol tridehydrocrepenynate. Extraction of C. cibarius fruit bodies with ethanol or methanol afforded fatty acid ethyl or methyl esters as a result of esterification/transesterification reactions. Insecticidal activity of the isolated glycerides and esters was much lower than that of the crude extracts and chromatographic fractions suggesting a synergistic effect of some of the compounds present in the mixture.
Fatty Acid Composition of Juniperus Species (Juniperus Section) Native to Turkey
Authors: Güvenç Ayşegül , Küçükboyacι Nurgün , Gören Ahmet Ceyhan
Published: March 2019

Fatty acid compositions of seeds of five taxa of the Juniperus section of the genus Juniperus L. (Cupressaceae), i. e. J. drupacea Lab., J. communis L. var. communis, J. communis var. saxatilis Pall., J. oxycedrus L. subsp. oxycedrus, and J. oxycedrus subsp. macrocarpa (Sibth. & Sm.) Ball, were investigated. Methyl ester derivatized fatty acids of the lipophylic extracts of the five species were comparatively analyzed by capillary gas chromatography-mass spectrometry (GC-MS). Juniperus taxa showed uniform fatty acid patterns, among which linoleic (25.8–32.5%), pinolenic (11.9–24.1%) and oleic acids (12.4–17.2%) were determined to be the main fractions in the seed oils. Juniperonic acid was found to be remarkably high in J. communis var. saxatilis (11.4 %), J. oxycedrus subsp. oxycedrus (10.4 %), and J. communis var. communis (10.1 %). To the best of our knowledge, the present work discloses the first report on the fatty acid compositions of seeds of this Juniperus section grown in Turkey.
Quantitative and Physical Evaluation of Patchouli Essential Oils Obtained from Different Sources of Pogostemon cablin
Authors: Hussin Norma , Mondello Luigi , Costa Rosaria , Dugo Paola , Yusoff Nik Idris Nik , Yarmo Mohd Ambar , Wahab Ahmad Ab. , Said Mamot
Published: March 2019

Patchouli essential oil can be obtained from fresh, dried and fermented plant material. It is a highly valuable product in the fragrance industry and its quality changes depending upon raw material age and oil storage. In this work, patchouli essential oils derived from different treatments have been subjected to GC-FID quantitative analysis using an internal standard (ISTD) method with response factors (RF). Samples were obtained from i) fresh plants; ii) hydrodistillation of one year mature and fermented plants; iii) hydrodistillation of one year mature plants; iv) commercial products from Indonesia and Malaysia. Linear Retention Indices (LRI) for both polar and non-polar GC-MS analyses were also measured as a tool for qualitative analysis towards a homologous series of C7-C30 n-alkanes. The results obtained confirmed that, in all samples, patchouli alcohol was the main volatile constituent, with higher amount in lab-scale produced oils, compared with commercial samples. Other major compounds, in lab oils and commercial samples respectively, were: δ-guaiene, α-guaiene, pogostol, seychellene and α-patchoulene. Another 36 compounds were also found.