bluuebunny/crossref_metadata_2025 huggingface dataset:
Two New Tropane Alkaloids from the Bark of Erythroxylum vacciniifolium Mart. (Erythroxylaceae)
Authors: Queiroz Emerson F. , Zanolari Boris , Marston Andrew , Guilet David , Burgener Leila , Paulo Marçal de Queiroz , Hostettmann Kurt
Published: March 2019

Two new tropane alkaloid N-oxides substituted by a methylpyrrole moiety were isolated from the bark of Erythroxylum vacciniifolium Mart. (Erythroxylaceae), a Brazilian indigenous plant, locally known as catuaba and used in traditional medicine as an aphrodisiac. The alkaloid structures were determined by a combination of high resolution mass spectrometry and multi-dimensional NMR spectroscopy.
Detection by UPLC/ESI-TOF-MS of Alkaloids in Three Lycopodiaceae Species from French Polynesia and Their Anticholinesterase Activity
Authors: Ho Raimana , Marsousi Niloufar , Eugster Philippe , Bianchini Jean-Pierre , Raharivelomanana Phila
Published: March 2019

Three Lycopodiaceae species from French Polynesia, Lycopodium venustulum C. Gaudichaud, Lycopodiella cernua (C. Linnaeus) R. E. Pichi Sermolli and Lycopodium henryanum E. D. Brown were investigated for their alkaloidal composition by UHPLC/ESI-TOF-MS. Ten alkaloids were identified, with lycopodine and lycodoline being the main constituents in the three species. The acetylcholinesterase-inhibitory activities of the three species are probably due to the occurrence of huperzine A, huperzine B, huperzine E, huperzinine and lycopodine.
HPLC Analysis and NMR Identification of Homoisoflavonoids and Stilbenoids from the Inter-bulb Surfaces of Scilla nervosa
Authors: Bezabih Merhatibeb , Famuyiwa Samson O. , Abegaz Berhanu M.
Published: March 2019

The yellow inter-bulb deposits from Scilla nervosa were analyzed by HPLC and found to contain 19 major components. Twelve of the 19 were identified by comparison of Rt values with those of authentic homoisoflavonoids and stilbenoids, co-elution and by preparative isolation followed by NMR and MS analyses. Of these, two homoisoflavonoids, 3-(4-hydroxyoxybenzyl)-5,7-dimethoxy-6-hydroxychroman-4-one and 3-(4-methoxybenzyl)-6,7-dimethoxy-5-hydroxychroman-4-one are new.
Volatile Constituents of Ocimum minimum Herb Cultivated in Portugal
Authors: Skalicka-Woźniak Krystyna , Ludwiczuk Agnieszka , Widelski Jarosłtaw , Filipe Joao J. , Asakawa Yoshinori , Głtowniak Kazimierz
Published: March 2019

The chemical composition of the diethyl ether extracts of Ocimum minimum L., a traditional herb cultivated in Portugal, was evaluated. Thirty-two compounds were identified, the major ones being linalool (24.7%), eugenol (20.5%), 1,8-cineole (9.6%), β-elemene (6.6%) and trans-α-cubebene (6.3%).
Ring B Aromatic Steroids from an Endophytic Fungus, Colletotrichum sp.
Authors: Zhang Wen , Draeger Siegfried , Schulz Barbara , Krohn Karsten
Published: March 2019

The new (22E,24R)-3-acetoxy-19(10→6)-abeo-ergosta-5,7,9,22-tetraen-3β-ol (1) and the known (22E,24R)-19(10→6)-abeo-ergosta-5,7,9,22-tetraen-3β-ol (2), two interesting ergosteroids with rare aromatized ring B, together with seven known derivatives, namely (22E,24R)-ergosta-5,7,22-trien-3β-ol (3), (22E,24R)-ergosta-4,7,22-trien-3-one (4), (22E,24R)-ergosta-4,6,8(14),22-tetraen-3-one (5), (22E,24R)-5α,8α-epidioxyergosta-6,22-dien-3β-ol (6), (22E,24R)-ergosta-7,22-dien-3β,5α,6β-triol (7), (22E,24R)-6-acetoxy-ergosta-7,22-dien-3β,5α,6β-triol (8), and (22E,24R)-3,6-diacetoxy-ergosta-7,22-dien-3β,5α,6β-triol (9), were isolated from Colletotrichum sp., an endophytic fungus isolated from Ilex canariensis from Gomera. The structures of these compounds were elucidated by detailed spectroscopic analysis, comparison with reported data, and chemical interconversion. The isolation of these metabolites not only displays a beautiful array of chemical diversity, but also gives insight into the biosynthetic interconnections. Preliminary studies showed antimicrobial activity of these compounds against the fungus Microbotryum violaceum, the alga Chlorella fusca, and the bacteria Escherichia coli and Bacillus megaterium.
New Polyketides from the Marine-derived Fungus Phaeosphaeria spartinae
Authors: Elsebai Mahmoud Fahmi , Kehraus Stefan , Gütschow Michael , König Gabriele M.
Published: March 2019

The fungus Phaeosphaeria spartinae is an endophyte of the marine alga Ceramium sp. Investigation of this marine-derived fungus led to the isolation of the new natural products spartinol A (1), B (2), C (3) and D (4). The structures of these closely related compounds were established from extensive spectroscopic investigations. Compound 3 showed weak inhibition of human leukocyte elastase (HLE).
Spirobisnaphthalenes from the Endophytic Fungus Dzf12 of Dioscorea zingiberensis and Their Antimicrobial Activities
Authors: Cai Xiaoyue , Shan Tijiang , Li Peiqin , Huang Yongfu , Xu Lijian , Zhou Ligang , Wang Mingan , Jiang Weibo
Published: March 2019

Five spirobisnaphthalenes, namely palmarumycin CP17 (1), diepoxin κ (2), diepoxin η (3), diepoxin ζ (4), and diepoxin γ (5), were isolated from the endophytic fungus Dzf12 associated with the medicinal plant Dioscorea zingiberensis C. H. Wright. Their structures were identified by physicochemical and spectrometric analysis. Among these spirobisnaphthalenes, 2 was found to have antibacterial activity, and the mixture of 3 and 4 was detected to have both antibacterial and antifungal activities.
Cytotoxic Metabolites Produced by Alternaria No.28, an Endophytic Fungus Isolated from Ginkgo biloba
Authors: Qin Jian-Chun , Zhang Ya-Mei , Hu Ling , Ma Ya-Tuan , Gao Jin-Ming
Published: March 2019

From the medicinal plant Ginkgo biloba the fungal endophyte Alternaria no.28 was isolated. Extract of the fungus grown in liquid culture media exhibited marked cytotoxic activity when tested in vitro against brine shrimp (Artemia salina). Eight compounds were isolated from the extract of cultures of this endophytic fungus and were elucidated as alterperylenol (1), altertoxin I (2), alternariol (3), alternariol monomethyl ether (4), tenuazonic acid (5) and its derivative (6), together with ergosterol and ergosta-4, 6, 8, 22-tetraen-3-one by means of spectroscopic analysis. Among them, both 5 and 6 showed significant cytotoxic effects in the brine shrimp bioassy, with mortality rates of 73.6% and 68.9%, respectively, at a concentration of 10 μg.mL−1, and they were first isolated from endophytic fungi.
Chemical and Functional Diversity of Natural Products from Plant Associated Endophytic Fungi
Authors: Verma Vijay C. , Kharwar Ravindra N. , Strobel Gary A.
Published: March 2019

This review describes examples of naturally occurring bioactive compounds obtained from fungal endophytes from various host plants. The main topics addressed are sources, identification, biological activity, biosynthesis, and ecological and chemosystematic significance of those bioactive compounds whose sources were well defined.
Suppression of Linalool Acetate Production in Lavandula x intermedia
Authors: Desautels Amy , Biswas Kamal , Lane Alexander , Boeckelmann Astrid , Mahmoud Soheil S.
Published: March 2019

Linalool acetate, one of the major constituent of several essential oils, is heat-labile and decomposes upon exposure to the high injector temperature during gas chromatography. Here we report the development of an improved method for detection of this compound by gas chromatography mass spectrometry (GCMS) using cold on-column injection of the sample. By using this sensitive method, it has been demonstrated that a lavandin (L.x intermedia) mutant accumulates trace quantities of linalool acetate and camphor and higher amounts of cineole and borneol compared to its parent. This plant, which very likely carries a point mutation in one or more of the genes involved in essential oil production, provides a unique tool for investigating regulation of essential oil biogenesis in plants.
Cytotoxic Activity of seco-Entkaurenes from Croton caracasana on Human Cancer Cell Lines
Authors: Suárez Alírica I. , Chavez Katiuska , Mateu Elsa , Compagnone Reinaldo S. , Muñoz Arturo , Sojo Felipe , Arvelo Francisco , Mijares Michael , De Sanctis Juan B.
Published: March 2019

In the course of searching for bioactive compounds from Croton species from Venezuela, two seco-entkaurenes isolated from flowers of Croton caracasana were evaluated in vitro for their effect on cell viability by the standard MTT assay in nine human cancer cell lines of different origins and one primary culture. Both compounds induced cytotoxicity in the range of 2 to 25 μM for caracasine and 0.8 to 12 μM for caracasine acid. However, for the normal fibroblasts and the cell lines, HeLa, MCF-7, PC-3, LoVo, X-17, Jurkat E6.1 and Jurkat JCaM1.6, the IC50 values of caracasine acid were lower than their counterparts. Interestingly, no differences in IC50 were recorded for the leukemic cell lines U937 and K562. It can be concluded that the acid moiety in the structure enhances the cytotoxic effect of caracasine by a pathway which seems not to be activated in the leukemic cell lines tested.
Antioxidant Principles of Tanacetum vulgare L. Aerial Parts
Authors: Juan-Badaturuge Malindra , Habtemariam Solomon , Jackson Caroline , Thomas Michael JK
Published: March 2019

The methanolic extract of aerial parts of Tanacetum vulgare L. (Asteraceae) and its fractions were investigated for antioxidant activity. The crude extract displayed DPPH radical scavenging effects with an EC50 value of 37 ± 1.2 μg/mL (n=3). Activity-guided fractionations of the crude extract resulted in the isolation of three antioxidant compounds; 3,5-O-dicaffeoylquinic acid (3,5-DCQA), axillarin and luteolin. 3,5-DCQA was the major constituent with antioxidant activity (IC50 = 9.7 μM) comparable with that of the standard quercetin (IC50 = 8.8 μM). Though the isolated compounds were previously known for their antioxidant effects, this is the first report on the identification of 3,5-DCQA from Tanacetum vulgare. The displayed potent antioxidant activity of the crude extract and isolated active principles is in support of the traditional medicinal uses of the plant for disease conditions such as wound healing, rheumatic arthritis and other inflammatory conditions.
Influence of Growth Phase and Geographic Origin on the Essential Oil Composition of Pituranthos chloranthus from Tunisia
Authors: Neffati Aïcha , Hennequin Didier , Basset Benoît , Chekir-Ghedira Leïla , Ghedira Kamel , Barillier Daniel , Ledauphin Jérôme
Published: March 2019

The chemical compositions of the essential oils of Pituranthos chloranthus harvested at the vegetative, flower budding, flowering and fruiting stages from three distinct geographical areas of Tunisia were investigated using GC-FID and GC–MS. One hundred and fifty compounds were identified in which α-pinene, β-pinene, α-phellandrene, β-myrcene, β-phellandrene, p-cymene, 8-methyldecanal, exo-2-hydroxycineole acetate and carvacrol could reach more than 10% of the total amount. However, this composition varied with respect to both the geographical area and the season. A clear discrimination of samples could be achieved by submitting the results to PLS discriminant analysis. p-Cymenene was only detected at the floral budding stage (February), whereas high amounts of exo-2-hydroxycineole and exo-2-hydroxycineole acetate were specific for the flowering period (April). Carvacrol was showed to be characteristic mainly of the fruiting period (August), whereas the vegetative state (November) could be distinguished from the others by the presence of α- and β-pinene. Limonene, camphene, geraniol and β-damascenone were likely to be specific for the essential oils of this species collected from the different regions of Tunisia.
Characterization of Mandarin (Citrus deliciosa Ten.) Essential Oil. Determination of Volatiles, Non-Volatiles, Physico-Chemical Indices and Enantiomeric Ratios
Authors: Bonaccorsi Ivana , Dugo Paola , Trozzi Alessandra , Cotroneo Antonella , Dugo Giovanni
Published: March 2019

An investigation of 27 samples of mandarin essential oils (Citrus deliciosa Tenore), industrially produced in Sicily during the 2007-2008 season, was performed to determine the composition of the volatile fraction by GC/FID and GC/MS-LRI, the enantiomeric distribution of some monoterpene hydrocarbons and linalol by Es-GC, the non-volatile oxygen heterocyclic components by RP-HPLC/PDA and the physicochemical indices (relative density, refractive index, optical rotation, residue on evaporation, and UV spectroscopic CD value). This study up-dates the information available in the literature on Sicilian mandarin (C. deliciosa Ten.) essential oils, and provides information on the composition and quality parameters for the evaluation of this product.
Chemical Composition and Antimicrobial Activity of Essential Oil of Bupleurum montanum and B. plantagineum
Authors: Laouer Hocine , Hirèche-Adjal Yasmina , Prado Soizic , Boulaacheb Nacira , Akkal Salah , Singh Gurdip , Singh Pratibha , Isidorov Valery A. , Szczepaniak Lech
Published: March 2019

The hydrodistilled oils from the aerial parts of Bupleurum montanum and B. plantagineum, which are endemic to North Africa, including Algeria, were analyzed by gas chromatography-mass spectrometry (GC-MS). Ninety-eight compounds were detected in the oil of B. montanum, representing 98.6% of the total oil, and 68 in the oil of B. plantagineum, representing 99.8% of the total. Megastigma-4,6-(E),8(2)-triene was the major constituent of B. montana oil (25.3%). Other important compounds were myrcene, α-pinene and benzyl tiglate. Conversely, the major constituents of the oil of B. plantagineum were α-pinene (31.9%), cis-chrysanthenyl acetate (28.2%), and myrcene (24.8%), followed by the monoterpene hydrocarbon limonene (5.1%). The mutagenic, antiplasmodial and antimicrobial activities of the essential oils were individually evaluated against eleven microorganisms, using the agar diffusion method, by determination of MIC values. The investigated oils exhibited moderate antimicrobial activity. Maximum activity of the oils was observed against Nocardia asteroides, Staphylococcus aureus and Enterococcus faecalis. Fungicidal activity against Candida albicans was also found for both oils.
Molecular Pharmacognosy: A new Borderline Discipline
Authors: Huang Lu-Qi , Yuan Yuan , Cui Guang-Hong , Dai Zhu-Bo , Xiao Pei-Gen
Published: March 2019

Pharmacognosy has developed rapidly in recent years and now represents a highly interdisciplinary science. At the boundary between pharmacognosy and molecular biology, molecular pharmacognosy has developed as a new borderline discipline. Using the method and technology of molecular biology, molecular pharmacognosy focuses on resolving a wide range of challenging problems, such as distinguishing herbal and animal drug populations by molecular marker assay, conserving and utilizing wild resources on the basis of knowledge of genetic diversity, investigating the mechanism of active compound accumulation and obtaining new resources with higher quality through genetic engineering. Recent research results show that molecular pharmacognosy has extended the scope of pharmacognostical science and plays an important role in the safe and efficient usage of crude drugs.
Terpenoid Content of the Antarctic Soft Coral Alcyonium antarcticum
Authors: Manzo Emiliano , Ciavatta Maria Letizia , Nuzzo Genoveffa , Gavagnin Margherita
Published: March 2019

Chemical investigation of the soft coral Alcyonium antarcticum, collected off Terra Nova Bay, resulted in the isolation of two closely related sesquiterpenes, alcyonicene (1) and deacetoxy-alcyonicene (2), along with known terpenoid compounds. The structure elucidation of the new molecules, possessing a rare bulgarane skeleton, has been made mainly by NMR techniques.
A New β-D-Glucopyranosyl 2-Oxo-urs-12-en-28-oate from the Cameroonian Plant Combretum bracteatum
Authors: Ntchatcho Germain , Verotta Luisella , Finzi Paola Vita , Zanoni Giuseppe , Vidari Giovanni
Published: March 2019

From the Cameroonian plant Combretum bracteatum (Laws.) Engl. and Diels a new compound, β-D-glucopyranosyl 3β,19α-dihydroxy-2-oxo-urs-12-en-28-oate, was isolated along with three known ursane and oleane triterpenes and two galactopyranosyl lipids. This represents the first example of a naturally occurring 2-oxo-urs-12-enoic acid derivative.
Cyclohexanones from Mimulus glabratus and M. luteus
Authors: Piovano Marisa , Garbarino Juan , Tomassini Lamberto , Nicoletti Marcello
Published: March 2019

The phytochemical study of Mimulus glabratus A. Gray allowed the isolation of two cyclohexenones: the new compound 6-chlorohalleridone 1 and halleridone 2. Halleridone was also identified in Mimulus luteus L., together with dihydroalleridone 3, the naphtoquinone α-dunnione 4, ursolic acid and β-sitosterol.
New Flavonoid Glycosides from Vernonia ferruginea
Authors: Malafronte Nicola , Pesca Maria Sabina , Bisio Angela , Escobar Luis Morales , De Tommasi Nunziatina
Published: March 2019

Four new flavonoid glycosides, quercetin 3-O-β-D-xylopyranosyl-(1-4)-β-D-glucopyranoside, quercetin 3-O-β-D-apiofuranosyl-(1-4)-β-D-glucopyranoside, kaempferol 3-O-β-D-apiofuranosyl-(1-4)-β-D-glucopyranoside, and kaempferol 4′-methyl ether 3-O-β-D-xylopyranoside, along with other known flavonoids and phenolic derivatives, were isolated from the leaves of Vernonia ferruginea Less. Their structures were established on the basis of detailed spectral analysis.
Phytochemical Profile of Iris tenax Extract
Authors: Piccin Antonella , Serafini Mauro , Nicoletti Marcello
Published: March 2019

A phytochemical profile of a botanical product (TM) from Iris tenax has been produced focused on flavonoids and iridals, leading to a useful fingerprint of the tested extract based on HPLC and NMR data.
Characterization of Flavonoid and Naphthopyranone Derivatives from Eriocaulon ligulatum using Liquid Chromatography Tandem Mass Spectrometry
Authors: Santos Lourdes Campaner dos , da Silva Marcelo Aparecido , Rodrigues Clenilson Martins , Carbone Virginia , Napolitano Assunta , Bassarello Carla , Mari Angela , Piacente Sonia , Pizza Cosimo , Vilegas Wagner
Published: March 2019

Liquid chromatography-electrospray ionization multistage ion trap mass spectrometry (LC-ESI-IT-MSn) was used to analyze the secondary metabolites in the methanol extract of the capitulae of Eriocaulon ligulatum. The major components were mono-and diglycosides of flavonoids and naphthopyranones. Eleven compounds, including four new flavonol glycosides, were identified based on their fragmentation patterns in MS experiments and on NMR analysis of the isolated compounds. The described data may contribute to a better understanding of the taxonomic classification of the Eriocaulaceae family.
Prunus spinosa Fresh Fruit Juice: Antioxidant Activity in Cell-free and Cellular Systems
Authors: Fraternale Daniele , Giamperi Laura , Bucchini Anahi , Sestili Piero , Paolillo Marco , Ricci Donata
Published: March 2019

The antioxidant activity was assessed of fresh juice from Prunus spinosa L. fruit (Rosaceae) growing wild in Urbino (central Italy) by using different cell-free in vitro analytical methods: 5-lipoxygenase test, 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging, and oxygen radical absorbance capacity (ORAC). Trolox was used as the reference antioxidant compound. In the 5-lipoxygenase and DPPH tests the fresh fruit juice of P. spinosa showed good antioxidant activity when compared with Trolox, while the ORAC value was 36.0 μmol eq. Trolox /g of fruit. These values are in accord with data reported in the literature for small fruits such as Vaccinium, Rubus and Ribes. The antioxidant capacity in cell-free systems of P. spinosa juice has been compared with its cytoprotective – bona fide antioxidant activity in cultured human promonocytes (U937 cells) exposed to hydrogen peroxide. The antioxidant activity of red berries has been correlated with their anthocyanin content. The results of this study indicate that the three most representative anthocyanins in P.spinosa fruit juice (cyanidin-3-rutinoside, peonidin-3-rutinoside and cyanidin-3-glucoside) are likely to play an important role in its antioxidant properties.
ESI-MS, ESI-MS/MS Fingerprint and LC-ESI-MS Analysis of Proathocyanidins from Bursera simaruba Sarg Bark
Authors: Maldini Mariateresa , Montoro Paola , Piacente Sonia , Pizza Cosimo
Published: March 2019

Direct flow injection/electrospray ionization/ion trap tandem mass spectrometry was used to investigate the presence of proanthocyanidins (PAs) in the methanolic extract of B. simaruba bark. Additionally, an LC-ESI-MS qualitative study was performed by using a monolithic stationary phase. The fragmentation pattern obtained evidenced the presence in B. simaruba bark of PAs belonging to the series of polymers of epicatechin, along with their glycosilated derivatives.
Chemical Composition of the Essential Oil from Jasminum pubescens Leaves and Flowers
Authors: Temraz Abeer , Cioni Pier Luigi , Flamini Guido , Braca Alessandra
Published: March 2019

The essential oil obtained from the leaves and flowers of Jasminum pubescens (Retz.) Willd. (Oleaceae) has been analyzed by GC/MS. Sixty-three and sixty-four components of the essential oils, representing 95.0% of the total oil for the leaves and 91.9% for the flowers, were identified, respectively. Both the oils were mainly constituted by non-terpene derivatives (58.2% and 50.8%, respectively), among which aldehydes (44.7%) characterized the essential oil from the leaves. Besides aldehydes (14.3%) and other carbonylic compounds (acids, esters, and ketones, 38.1%) were the main non-terpene compounds of the oil from the flowers.
Chemistry, Antioxidant, Antibacterial and Antifungal Activities of Volatile Oils and their Components
Authors: De Martino Laura , De Feo Vincenzo , Fratianni Florinda , Nazzaro Filomena
Published: March 2019

The present paper reports the chemical composition, antioxidant and antibacterial activities of several essential oils and their components. Analysis showed that three oils (Carum carvi L., Verbena officinalis L. and Majorana hortensis L.) contained predominantly oxygenated monoterpenes, while others studied (Pimpinella anisum L., Foeniculum vulgare Mill.) mainly contained anethole. C. carvi, V. officinalis and M. hortensis oils exhibited the most potent antioxidant activity, due their contents of carvacrol, anethole and estragol. Antibacterial action was assessed against a range of pathogenic and useful bacteria and fungi of agro-food interest. V. officinalis and C. carvi oils proved the most effective, in particular against Bacillus cereus and Pseudomonas aeruginosa. Carvacrol proved most active against Escherichia coli, and completely inhibited the growth of Penicillium citrinum. The oils proved inactive towards some Lactobacilli strains, whereas single components showed an appreciable activity. These results may be important for use of the essential oils as natural preservatives for food products.
Chemical Composition of the Essential Oil of Commiphora erythraea
Authors: Marcotullio Maria Carla , Santi Claudio , Mwankie Gildas Norbert Oball-Mond , Curini Massimo
Published: March 2019

The essential oil composition of Commiphora erythraea (Ehrenb) Engl. is reported for the first time. The oil is rich in sesquiterpenes, particularly furanosesquiterpenes (50.3%). GC-MS analysis of the oil permitted differentiation between C. erythraea and C. kataf, two often confused species.
Insights on Novel Biologically Active Natural Products: 7-Isopentenyloxycoumarin
Authors: Epifano Francesco , Pelucchini Caroline , Curini Massimo , Genovese Salvatore
Published: March 2019

7-Isopentenyloxycoumarin is a prenyloxyphenylpropanoid derivative found in low concentration in a restricted number of plant families (Apiaceae, Asteraceae, and Rutaceae). Synthetic schemes were recently developed enabling sufficient quantities of the title coumarin to be obtained in order to evidence its valuable biological effects, mainly as an anticancer agent. The aim of this review is to examine the phytochemical and pharmacological properties of this compound.
Garlic: Empiricism or Science?
Authors: Aviello Gabriella , Abenavoli Ludovico , Borrelli Francesca , Capasso Raffaele , Izzo Angelo Antonio , Lembo Francesca , Romano Barbara , Capasso Francesco
Published: March 2019

Garlic (Allium sativum L. fam. Alliaceae) is one of the best-researched, best-selling herbal remedies and is also commonly used as a food and a spice. Garlic constituents include enzymes (for example, alliinase) and sulfur-containing compounds, including alliin, and compounds produced enzymatically from alliin (for example, allicin). Traditionally, it has been employed to treat infections, wounds, diarrhea, rheumatism, heart disease, diabetes, and many other disorders. Experimentally, it has been shown to exert antilipidemic, antihypertensive, antineoplastic, antibacterial, immunostimulant and hypoglycemic actions. Clinically, garlic has been evaluated for a number of conditions, including hypertension, hypercholesterolemia, intermittent claudication, diabetes, rheumatoid arthritis, common cold, as an insect repellent, and for the prevention of arteriosclerosis and cancer. Systematic reviews are available for the possible antilipidemic, antihypertensive, antithrombotic and chemopreventive effects. However, the clinical evidence is far from compelling. Garlic appears to be generally safe although allergic reactions may occur.
Multi-stage Mass Spectrometric Analysis of Saponins in Glycyrrhiza radix
Authors: Tanaka Ken , Hayashi Kosuke , Fahad Abrar , Arita Masanori
Published: March 2019

The fragmentation pathways of six triterpenoid saponins from Glycyrrhiza radix were investigated using LC-MS/MS. Depending on the structure and the substitution pattern, different molecular adduct ions, [M+NH4]+ or [M+H]+, were observed in the positive ESI spectra. In the positive MSn spectra from the molecular adduct ions, characteristic product ions corresponding to the loss of dehydrated glucuronic acid or glucuronic acid were detected and they indicated the type of substitution and structural modification. Fragment ions originating from the sapogenin moiety in the positive mass spectra were predominantly provided by saponins having an 11-oxo-12-ene structure. On the other hand, the saponins gave fragment ions corresponding to the sugar moiety in the negative mass spectra. These results indicate the specific property of saponins that have the 11-oxo-12-ene structure to localize positive or negative charge in the mass spectrometric ionization and fragmentation process. Information obtained from the present study can be utilized for structural elucidation of triterpenoid saponins in the Glycyrrhiza radix by LC-MS.
Phenolic Compounds of Mountain Tea from the Balkans: LC/DAD/ESI/MSn Profile and Content
Authors: Petreska Jasmina , Stefkov Gjose , Kulevanova Svetlana , Alipieva Kalina , Bankova Vassya , Stefova Marina
Published: March 2019

Twenty-one samples of Sideritis species ( S. scardica, S. raeseri, S. taurica, S. syriaca and S. perfoliata) from various locations on the Balkan Peninsula were evaluated for their chemical constituents. Chemical analyses were focused on secondary metabolites, particularly phenolic compounds, which have several roles in the plant physiological processes and have demonstrated significant health beneficial effects. The occurrence of hydroxycinnamic acids, phenylethanoid glycosides and flavonoids has been investigated in taxonomically related taxa of the genus Sideritis. A systematic method for phenolic compounds identification was developed using tandem mass spectrometry coupled to high performance liquid chromatography with diode array detection. Scanning for precursor ions of commonly found phenolics in Sideritis species using LC/MSn with an ion trap instrument permitted the specific determination of hydroxycinnamic acid derivatives, and phenylethanoid and flavonoid glycosides. Further characterization of each phenolic compound was performed using MS/MS production analysis and common–neutral-loss analysis. This online technique allowed identification of three hydroxycinnamic acid derivatives, eight phenylethanoid glycosides, and twenty-four flavonoid glycosides.

All the taxa analysed produced very similar phenolic patterns characterized by the presence of 5-caffeoylquinic acid, lavandulifolioside, verbascoside, hypolaetin 7- O-[6′”- O-acetyl]-allosyl(1→2)glucoside, apigenin 7-(4″- p-coumaroylglucoside), 4′- O-methylisoscutellarein 7- O-[6′”- O-acetyl]-allosyl(1→2)glucoside, and minor amounts of isoverbascoside, apigenin 7- O-allosyl(1→2)glucoside, isoscutellarein 7- O-allosyl-(1→2)-[6′- O-acetyl]-glucoside, hypolaetin 7- O-allosyl-(1→2)-[6″- O-acetyl]-glucoside and 4′- O-methylhypolaetin 7- O-[6′”- O-acetyl]-allosyl-(1→2)-[6′- O-acetyl]-glucoside. These results show that the investigated species are systematically very closely related.

Phenylethanoid glycosides and flavonoid acetylglycosides are dominant and constitute 90% of the total phenolic compounds compared with hydroxycinnamic acid and flavonoid 7- O-glycosides.

Principal component analysis (PCA) was performed for the nature and content of the different compounds to be correlated to the particular Sideritis species and also to the locations.
Anthocyanins from Fuchsia Flowers
Authors: Jordheim Monica , Skaar Irene , Lunder Helene , Andersen Øyvind M.
Published: March 2019

Flowers of Fuchsia arborescens, F. boliviana, F. fulgens var. ‘Variegata', F. magellanica (Onagraceae) and twenty-nine F. magellanica cultivars contained some of the thirteen anthocyanidin 3,5-diglucosides (six), 3-monoglycosides (five) and 3-(2″-galloylglucosides) (two), which altogether were identified. Peonidin 3- O-(2″- O-galloyl-β-glucopyranoside), which has not been reported before, was found in F. magellanica and F. fulgens var. ‘Variegata’. The various corollas with purple nuances were correlated with a relatively high content of malvidin 3,5-diglucoside. Flower colors were to a large extent correlated with the number of oxygen substituents on the anthocyanidin B-ring of the major anthocyanins.
Aromatic Compounds from the Liverwort Conocephalum japonicum
Authors: Liu Na , Guo Dong-Xiao , Wang Yan-Yan , Wang Li-Ning , Ji Mei , Lou Hong-Xiang
Published: March 2019

Two undescribed dimeric ArC2 derivatives, cis- and trans-1,2-bis(3,4-dimethoxyphenyl)cyclobutane (1 and 2), one new monoterpenes esters, 2α,5β-dihydroxybornane-2- cis-cinnamate (3), along with eight known compounds, 2α,5β-dihydroxybornane-2- trans-cinnamate (4), perrottetin E (5), isoriccardin C (6), marchantin A (7), marchantin E (8), marchantin C (9), and isomarchantin C (10) were isolated from the liverwort Conocephalum japonicum. All the structures were established by extensive spectroscopic analysis. The isolated compounds 3–10 were evaluated for their cytotoxicity against the human KB cell line with IC50 values ranging from 16.5 to 50.2 μM.
New Stress Metabolite from Bulbophyllum kwangtungense
Authors: Chen Jianbo , Zhang Huifang , Chen Li , Wu Bin
Published: March 2019

A new dibenz[ b, f]oxepin (1) was found to be produced as a stress metabolite from the leaves and stems of Bulbophyllum kwangtungense Schlecht, in response to abiotic stress elicitation by CuCl2. The structure of 1 was established by spectroscopic and spectrometric means.
Targets of Red Grapes: Oxidative Damage of DNA and Leukaemia Cells
Authors: Anter Jaouad , de Abreu-Abreu Noriluz , Fernández-Bedmar Zahira , Villatoro-Pulido Myriam , Alonso-Moraga Ángeles , Muñoz-Serrano Andrés
Published: March 2019

Vitis vinifera is a widespread crop all over the world. The biophenols present in grapes have a remarkable influence on wine quality and also confer potential health-protecting properties to this fruit. The aim of the present work was to assess the beneficial properties of skin, seeds and pulp of red table grapes (RTG) ( Vitis vinifera, Palieri Cadiz variety). Two potential beneficial activities of red table grapes (RTG) were analyzed: (i) The maintenance of genomic stability studying their genotoxic/antigenotoxic effects, and (ii) the in vitro cytotoxic effect against tumor cells of RTG components.

The genotoxic and/or antigenotoxic effect was measured applying the somatic mutation and recombination test on wing imaginal discs of Drosophila melanogaster. The cytotoxic effect was monitored using the HL60 human leukemia model to evaluate the antiproliferative potential of the different parts of RTG. The three major parts (skin, seeds and pulp) are not genotoxic. When antigenotoxicity assays were performed using hydrogen peroxide as the oxidative genotoxin, skin, seed and pulp exerted a desmutagenic effect, with seeds and skin showing the most potent effect. The cytotoxicity tests using HL60 cells indicated that only skin and pulp fractions are able to inhibit the tumor growth, with skin having the lowest IC50 (1.8 mg/mL versus 8 mg/mL of pulp). These results suggest that RTG are potent anti-mutagens that protect DNA from oxidative damage as well as being cytotoxic toward the HL60 tumor cell line.
Extraction and Identification of Isothiocyanates from Broccolini Seeds
Authors: Zhang Bochao , Wang Xiaoqin , Yang Yanjing , Zhang Xuewu
Published: March 2019

Broccolini ( Brassica oleracea Italica x Alboglabra) is a cross between broccoli and kai-lan (Chinese broccoli), which contains abundant glucosinolates. The intact glucosinolates are believed to be inactive, while their hydrolysis products, such as isothiocyanates (ITCs), are found to have bacteriocidal and anticarcinogenic activities. So far, no report is available about generation of ITCs during the process of glucosinolate hydrolysis in broccolini. In this study, the hydrolysis of broccolini seed glucosinolates was investigated under controlled conditions of pH, time and temperature, and the ITCs produced were determined. The results showed that an optimum hydrolysis of glucosinolates could be achieved at a temperature of 25°C, at pH 7.0, and a reaction time of eight hours. Furthermore, GC-MS analysis indicated that the extracted ITCs primarily were: 3-BITC (3-benzyl-ITC) (10.8%), 4-methylpentyl-ITC (0.5%), 1-isothiocyanato-butane (26.8%), PEITC (phenethyl-ITC) (22.6%) and SFN (sulforaphane) (19.2%).
Essential Oil Composition of Vismia macrophylla Leaves (Guttiferae)
Authors: Rojas Janne , Buitrago Alexis , Rojas Luis , Morales Antonio
Published: March 2019

The essential oil from Vismia macrophylla Kunth (Guttiferae) leaves, extracted by hydrodistillation, was analyzed by GC/MS. The oil obtained (yield 0.11%) contained twenty-eight compounds, which were identified from their retention indices and by comparison of their mass spectra with those in the Wiley GC-MS Library data base. The major components were β-caryophyllene (20.1%), germacrene D (11.6%) and β-elemene (7.0%).
Chemical Variability of Essential Oils in Natural Populations of Cupressus dupreziana
Authors: Ramdani Messaoud , Lograda Takia , Chalard Pierre , Chalchat Jean Claude , Figueredo Gilles
Published: March 2019

Essential oils extracted from dried leaves of Cupressus dupreziana A. Camus, an endemic species in the Tassili n'Ajjer (Central Sahara of Algeria), were analyzed by gas chomatography coupled to mass spectrometry (GC-MS). Analyses were carried out on 164 trees of 26 natural populations in order to determine the intra-specific variability. Thirty-two terpenoïds were identified, the major ones being α-pinene (11.5 – 44.2), Δ3-carene (5.7 – 31.7) and germacrene-D (15.7 – 54.1). The terpenoid markers used made it possible to determine the individual patterns of chemotypic variability. This variability confirmed that genetic factors were not responsible for the decrease in the number of this species, the main reason probably being the Tassili n'Ajjer desertification.
2-Undecanone Rich Leaf Essential Oil from Zanthoxylum armatum
Authors: Bisht Deepa , Chanotiya Chandan S.
Published: March 2019

The leaf essential oils of Zanthoxylum armatum DC (Rutaceae) from Kumaon, India, extracted by hydrodistillation, were analyzed by capillary gas chromatography (GC-FID) and gas chromatography–mass spectrometry (GC-MS). The major classes of compounds found in the leaf oils were acyclic and menthane monoterpenoids as well as simple alcohols, aldehydes and ketones. The high proportion of non-terpenic acyclic ketones, notably 2-undecanone and 2-tridecanone, and the low abundance of undec-10-en-1-al and p-phellandren-8-ol make the composition entirely new. Other constituents present in significant amounts were oxygenated monoterpenes, which include 1,8-cineole, linalool, terpinen-4-ol, and α-terpineol, and sesquiterpene hydrocarbons represented mainly by trans-caryophyllene, α-humulene and germacrene D. On the contrary, the oil distilled from the leaves on the second day of distillation was characterized by a high content of 2-tridecanone (27.1%) and trans-caryophyllene (7.4%), as compared with 3.5% and 4.6%, respectively, for the fresh leaves; a slight decrease in pH of the distillate was also significant. Moreover, the presence of a high 2-undecanone content followed by 2-tridecanone is being reported for the first time for Z. armatum from this region. In terms of molecular diversity, the simple acyclic ketones dominate the essential oils as compared with linalool that was reported in several previous studies on Z. armatum. Therefore, the two acyclic ketones may be utilized to establish the origin and authenticity of the material.
Chemical Composition of the Essential Oil from Carramboa littlei (Asteraceae)
Authors: de Rojas Yndra Cordero , Rojas Luis B. , Usubillaga Alfredo
Published: March 2019

The essential oil from the leaves of Carramboa littlei Aristeg. was isolated by hydrodistillation yielding 0.09%, w/v. The chemical composition was determined by GC-FID and GC-MS. Sixteen components were identified by comparison of their mass spectra with Wiley and NIST library data. The major constituents of the oil were germacrene-D (50.0%), bicyclogermacrene (4.8%) and ent-kaur-16-en-19-al (21.8%).
Composition, Antioxidant and Antimicrobial Activities of the Seed Essential Oil of Calocedrus formosana from Taiwan
Authors: Ho Chen-Lung , Tseng Yen-Hsueh , Wang Eugene I-Chen , Liao Pei-Chun , Chou Ju-Ching , Lin Chien-Nan , Su Yu-Chang
Published: March 2019

The hydrodistillated seed essential oil of Calocedrus formosana was analyzed to determine its composition and yield. Twenty-seven compounds were identified, the main ones being α-pinene (63.8%), totarol (9.9%) and ferruginol (8.9%). Monoterpene hydrocarbons (73.5%) and oxygenated diterpenes (18.8%) were the predominant groups of compounds. The seed essential oil exhibited excellent antioxidant, antimicrobial and anti-wood-decay fungal activities.
Leaf Essential Oil of Manekia naranjoana (Piperaceae) from Costa Rica and its Cytotoxic Activity
Authors: Chaverri Carlos , Díaz Cecilia , Cicció José F.
Published: March 2019

The chemical composition of the leaf oil of Manekia naranjoana (C. DC.) Callejas (Piperaceae) from Costa Rica was analyzed by capillary GC/FID and GC/MS. Fifty-five compounds were identified. Major compounds from the leaf oil were β-pinene (30.6%), α-pinene (18.8%), limonene (13.7%), and β-caryophyllene (6.1%). The oil presented very low toxicity to tumor and non-tumor cell lines, even though it contains components, such as α- and β-pinene, limonene and others, which have been shown to be cytotoxic. This is the first report of the chemical composition of the essential oil obtained from this species.
Anthocyanins as Antimicrobial Agents of Natural Plant Origin
Authors: Cisowska Agnieszka , Wojnicz Dorota , Hendrich Andrzej B.
Published: March 2019

Anthocyanins are particularly abundant in different fruits, especially in berries. The beneficial effects of these compounds for human health have been known from at least the 16th century. Despite the great number of papers devoted to the different biological effects exerted by anthocyanins only a limited number of studies is focused on the antimicrobial activity of these compounds. Anthocyanin content of berry fruits varies from 7.5 mg/100 mg fresh fruit in redcurrant ( Ribes rubum) up to 460 mg/100 g fresh fruit in chokeberry ( Aronia melanocarpa). After consumption, anthocyanins are intensively metabolized, mainly in the intestines and liver. Glucorination, methylation and sulfation are the most typical metabolic reactions. Antimicrobial activity of crude extracts of plant phenolic compounds against human pathogens has been intensively studied to characterize and develop new healthy food ingredients as well as medical and pharmaceutical products. However, there is very little information available about the antimicrobial activity of the pure anthocyanins. In the last part of this review we present the collection of papers describing the anthocyanin profiles of different fruits (mainly berries) and the antimicrobial properties of the identified compounds. Generally, anthocyanins are active against different microbes, however Gram-positive bacteria usually are more susceptible to the anthocyanin action than Gram-negative ones. Mechanisms underlying anthocyanin activity include both membrane and intracellular interactions of these compounds. Antimicrobial activity of berries and other anthocyanin-containing fruits is likely to be caused by multiple mechanisms and synergies because they contain various compounds including anthocyanins, weak organic acids, phenolic acids, and their mixtures of different chemical forms. Therefore, the antimicrobial effect of chemically complex compounds has to be critically analyzed.
Two Minor Diterpene Glycosides from the Leaves of Stevia rebaudiana
Authors: Chaturvedula Venkata Sai Prakash , Rhea Joshua , Milanowski Dennis , Mocek Ulla , Prakash Indra
Published: March 2019

Two new new diterpene glycosides, 13-[(2- O-(6- O-β-D-glucopyranosyl)-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy] kaur-16-en-18-oic acid β-D-glucopyranosyl ester (1) and 13-[(2- O-β-D-glucopyranosyl-3- O-β-D-fructofuranosyl-β-D-glucopyranosyl)oxy] kaur-16-en-18-oic acid β-D-glucopyranosyl ester (2) were isolated from the leaves of Stevia rebaudiana, along with the known steviol glycosides stevioside, rebaudiosides A-F and dulcoside A. The structures of the two new compounds were established on the basis of extensive 2D NMR (COSY, HSQC, and HMBC), MS and chemical studies.
Chemical Constituents of Lycoris albiflora and their Cytotoxic Activities
Authors: Jitsuno Maki , Yokosuka Akihito , Hashimoto Ken , Amano Osamu , Sakagami Hiroshi , Mimaki Yoshihiro
Published: March 2019

An alcoholic extract of Lycoris albiflora (Amaryllidaceae) showed potent cytotoxic activity against HL-60 cells with an IC50 value of 1.7 μg/mL. Phytochemical examination of the extract resulted in the isolation of 15 alkaloids, including two phenanthridine-type alkaloids (1, 2), one benzylphenethylamine-type alkaloid (3), two crinane-type alkaloids (4, 5), one pyrrolophenanthridine-type alkaloid (6), six lycorenan-type alkaloids (7–12), and three galanthamine-type alkaloids (13–15), together with three neolignans (16–18), two flavans (19, 20), and two acetophenone derivatives (21, 22). Compound 3 (hostasinine A) has not been isolated from Amaryllidaceae plants, and 1, 2, 4, 5, 7–9, 11, 12 and 14–22 are the first isolation and identification from L. albiflora. The phenanthridine-type alkaloids (1, 2), as well as the alkaloids (3–5), exhibited potent cytotoxic activities against not only HL-60 cells but also HSC-2 cells, thus leading to the conclusion that these alkaloids are mainly responsible for the cytotoxicity of the L. albiflora extract. Compound 1 (lycoricidinol), with the most potent cytotoxic activities, induced apoptosis in both HL-60 cells and HSC-2 cells. It is notable that 1 induced transient autophagy and morphological changes in mitochondria in the early stages of the apoptotic cell death process in HSC-2 cells.
Chemical Composition, Antioxidant Properties and Anti-cholinesterase Activity of Cordia gilletii (Boraginaceae) Leaves Essential Oil
Authors: Bonesi Marco , Okusa Philippe N. , Tundis Rosa , Loizzo Monica R. , Menichini Federica , Stévigny Caroline , Duez Pierre , Menichini Francesco
Published: March 2019

This study aimed to investigate for the first time the chemical composition, the antioxidant properties and the acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activity of the essential oil from the leaves of Cordia gilletii De Wild (Boraginaceae). The essential oil, characterized by 23 constituents (90.1% of the total oil), was constituted by terpene derivatives (25.6%) and non-terpene derivatives (64.5%), among which aldehydes, fatty acids and alkanes were present with the percentage of 16.5%, 18.8% and 23.1%, respectively. The antioxidant activity of C. gilletii essential oil was screened by two in vitro tests: DPPH and β-carotene bleaching test. The essential oil revealed antioxidant activity with an IC50 value of 75.0 and 129.9 μg/mL on DPPH radical and β-carotene decoloration tests, respectively. Moreover, C. gilletii inhibited AChE enzyme with an IC50 value of 105.6 μg/mL.
Composition and Antimicrobial Activity of Seseli montanum subsp. tommasinii Essential Oil
Authors: Šiljegović Jovana , Glamočlija Jasmina , Soković Marina , Vucković Ivan , Tešević Vele , Milosavljević Slobodan , Stešević Danijela
Published: March 2019

The essential oil isolated from Seseli montanum L. subsp. tommasinii Reich. f. was analyzed by GC/MS and the most abundant components were β-pinene (30.2%), germacrene D (10.1%), sabinene (8.0%), α-pinene (7.2%) and limonene (6.6%). The antimicrobial effect of the essential oil was evaluated against four bacterial and four fungal species among which were food contaminants, spoilage fungi, and plant, fungal and animal pathogens. The oil possessed moderate to strong antimicrobial activity.
Chemical Composition and Antimicrobial Activity of Anthriscus nemorosa Root Essential Oil
Authors: Pavlović Milica , Petrović Silvana , Milenković Marina , Couladis Maria , Tzakou Olga , Niketić Marjan
Published: March 2019

The essential oil obtained by hydrodistillation from the roots of Anthriscus nemorosa (Bieb.) Sprengel (Umbelliferae) was analyzed by GC and GC-MS. Among sixty-two compounds identified (representing 89.0% of the total oil), the main components were: n-nonane (12.1%), n-hexadecanol (6.9%), δ-cadinene (6.4%), β-pinene (6.0%) and germacrene D (5.4%). Furthermore, the antimicrobial activity of the oil was evaluated against the Gram-positive bacteria Staphylococcus epidermidis (ATCC 12228) and Bacillus subtilis (ATCC 6633), the Gramnegative bacterium Escherichia coli (ATCC 25922), and a yeast Candida albicans (ATCC 10259 and ATCC 24433) using the broth microdilution method.
Melidianolic Acid A and B, New Antimalarial Acyclic Diterpenes from Aphanamixis grandifolia
Authors: Astulla Adil , Hirasawa Yusuke , Rahman Abdul , Kusumawati Idha , Ekasari Wiwied , Widyawaruyanti Aty , Zaini Noor Cholies , Morita Hiroshi
Published: March 2019

Two new acyclic diterpenes, melidianolic acids A (1) and B (2), have been isolated from the bark of Aphanamixis grandifolia. Their structures were elucidated on the basis of spectroscopic and chemical methods. Melidianolic acids A (1) and B (2) showed antimalarial activity against Plasmodium falciparum 3D7 with IC50 of 6.1 and 7.3 μg/mL, respectively.
The Coloring Constituents of Scleroderma sinnamariense (Sclerodermaceae)
Authors: Putra Deddi Prima , Nurmilasari  , Komala Ismiarni , Asakawa Yoshinori , Arbain Dayar
Published: March 2019

Two known coloring constituents, methyl 4,4′-dimethoxyvulpinate (1) and 4,4′-dimethoxyvulpinic acid (2) have been isolated from the fruit body of fungus Scleroderma sinnamariense Mont. The methanolic extract, its fractions and compound (2) showed moderate activity to inhibit the growth of some pathogenic testing microbes used.
Thiophene, Furans, and Related Aromatic Compounds from Eupatorium heterophyllum
Authors: Saito Yoshinori , Takiguchi Koji , Gong Xun , Kuroda Chiaki , Tori Motoo
Published: March 2019

A thiophene, two furans, a dihydro furan, and two acetylenic benzene derivatives were isolated from the roots of Eupatorium heterophyllum collected in China. Structures were established on the basis of spectroscopic analyses as well as chemical transformations.