bluuebunny/crossref_metadata_2025 huggingface dataset:
Chemical Composition and Antimicrobial Activity of Cumin Oil (Cuminum Cyminum, Apiaceae)
Authors: Wanner Juergen , Bail Stefanie , Jirovetz Leopold , Buchbauer Gerhard , Schmidt Erich , Gochev Velizar , Girova Tanya , Atanasova Teodora , Stoyanova Albena
Published: March 2019

Cumin oil samples ( Cuminum cyminum L.) from four different geographical origins were analyzed using GC-MS and GC-FID for their qualitative and quantitative composition. The major compounds in all cumin oils were the monoterpenes β-pinene, p-cymene and γ-terpinene and the terpenoid aldehydes cuminic aldehyde and the isomeric menthadien carboxaldehydes. All essential oils, and cuminic aldehyde, were tested, using agar diffusion and serial dilution methods, against different Gram-positive and Gram-negative bacteria isolated from different sources of food (pork fillet, minced meat and sausages) and clinical isolates, as well as three different Candida albicans isolates. All cumin oils and cuminic aldehyde exhibited a considerable inhibitory effect against all the organisms tested, except Pseudomonas spp.
Chemical Composition and Antibacterial Activity of Selected Essential Oils and Some of Their Main compounds
Authors: Wanner Juergen , Schmidt Erich , Bail Stefanie , Jirovetz Leopold , Buchbauer Gerhard , Gochev Velizar , Girova Tanya , Atanasova Teodora , Stoyanova Albena
Published: March 2019

The chemical composition of essential oils of cabreuva ( Myrocarpus Fastigiatus Allemao, Fabaceae) from Brazil, cedarwood ( Juniperus ashei, Cupressaceae) from Texas, Juniper berries ( Juniperus communis L., Cupressaceae) and myrrh ( Commiphora myrrha (Nees) Engl., Burseraceae) were analyzed using GC/FID and GC/MS. The antimicrobial activity of these essential oils and some of their main compounds were tested against eleven different strains of Gram-positive and Gram-negative bacteria by using agar diffusion and agar serial dilution methods. Animal and plant pathogens, food poisoning and spoilage bacteria were selected. The volatile oils exhibited considerable inhibitory effects against all tested organisms, except Pseudomonas, using both test methods. Higher activity was observed against Gram-positive strains in comparison with Gram-negative bacteria. Cabreuva oil from Brazil showed similar results, but in comparison with the other oils tested, only when higher concentrations of oil were used.
Essential Oil Composition, Antimicrobial and Cytotoxic Activities of Two Endemic Stachys Cretica Subspecies (Lamiaceae) from Turkey
Authors: Şerbetçi Tuba , Demirci Betül , Güzel Çağrla Bozkurt , Kültür Şükran , Ergüven Mine , Başer Kemal Hüsnü Can
Published: March 2019

The chemical compositions of the water-distilled essential oil of Stachys cretica ssp. lesbiaca Rech. fil. and S. cretica ssp. trapezuntica Rech. fil. were determined by GC and GC–MS. Altogether 63 compounds were identified. The sesquiterpene hydrocarbon, germacrene D (20.3% and 12.9% respectively) was the main component identified in both oils. Furthermore, ethanol, light petroleum, dichloromethane, ethyl acetate and n-butanol extracts prepared from the aerial parts of the plants were tested for their antimicrobial activities against six bacterial strains and the yeast Candida albicans. The extracts exhibited no antibacterial activity, but the light petroleum and n-butanolic fractions showed low antifungal activities. Crude ethanolic extracts of the two subspecies were tested for their ability to inhibit the growth of HL-60 and Ishikawa human tumor cell lines. The IC50 values were 100 μg/mL for the HL-60 cell line and 200 μg/mL for the Ishikawa cell line.
Pharmacological Interactions of Essential Oil Constituents on the Viability of Microorganisms
Authors: Van Zyl Robyn Lynne , Seatlholo Sammy Tsietsi , Van Vuuren Sandy Freda , Viljoen Alvaro
Published: March 2019

Complex interactions between numerous components of essential oils often contribute to the pharmacological effect and therapeutic outcome. To further elucidate these interactions, several essential oil constituents (EOCs) were combined in different ratios and their inhibitory effects on the growth of bacteria and yeast determined using the minimum inhibitory concentration (MIC) microplate assay. When combined and tested against Candida Albicans, (+)-β-pinene interacted antagonistically with (-)-menthone (ΣFICT = 9.80), but synergistically with 1,8-cineole (ΣFICT = 0.35). Against Escherichia coli, the combination of E- and Z-(±)-nerolidol and geranyl acetate displayed an additive interaction (ΣFICT = 1.04); while a variable interaction was observed between E- and Z-(±)-nerolidol and eugenol with antagonism and synergy being observed at different ratios of each EOC. The combination of either carvacrol or eugenol with an antimicrobial agent (ciprofloxacin or amphotericin B) resulted in synergistic interactions against all microorganisms tested. These favourable results further support the use of essential oil constituents as adjuvants in the development of a new generation of phytopharmaceuticals that can be used in combination with synthetic drugs against drug-resistant microorganisms.
Encapsulation of Essential Oils within a Polymeric Liposomal Formulation for Enhancement of Antimicrobial Efficacy
Authors: van Vuuren Sandy F. , du Toit Lisa C. , Parry Ashleigh , Pillay Viness , Choonara Yahya E.
Published: March 2019

Essential oils and their constituents are known to possess antimicrobial activity; however, their inherent volatility is a limiting factor. In order to exploit the antimicrobial efficacy of essential oils, encapsulation within polymeric liposomal systems was undertaken. The liposomes were subsequently polymer-coated in order to further enhance the stability of the formulations. Essential oils distilled from Artemisia Afra, Eucalyptus Globulus and Melaleuca alternifolia were encapsulated into diastearoyl phosphatidylcholine and diastearoyl phosphatidylethanolamine liposomes employing a reverse phase evaporation methodology. A polyelectrolyte coating was then applied via the layer-by-layer self-deposition technique. A batch of the liposomes was polymer-coated with a 0.15%w/v chitosan solution. Using the minimum inhibitory concentration assay, the liposome-encapsulated, unencapsulated and polymer-coated liposome-encapsulated essential oils were compared in order to observe whether the antimicrobial efficacy was improved with encapsulation and polymer coating. Fractional inhibitory concentrations (FICs) were calculated in order to determine the antimicrobial interactions amongst the lipoid components, polymer coating and essential oils (synergistic, additive, indifferent and antagonistic interactions). With the exception of A. afra, microbial growth was inhibited at lower concentrations for the encapsulated formulations in comparison with the non-encapsulated oils. Synergistic to additive interactions were noted for encapsulated E. globulus (ΣFIC values 0.25-0.45) and M. alternifolia (ΣFIC values 0.26-0.52) formulations. The addition of the polymer coating did not enhance antimicrobial activity, but owing to their positive effects on membrane stability, its presence is important as a means of extending the shelf life of these formulations. Additionally, the presence of the polymeric coating availed the essential oil at a slower rate. This investigation is a stepping stone towards the promotion of the antimicrobial use of essential oils. The added benefits are that essential oils not only provide effective antimicrobial efficacy, but also promote a “greener” consumerism. Within liposomes, they will enhance dermato-cosmetic properties and increase the marketing image of the final product.
Eupatorium Capillifolium Essential Oil: Chemical Composition, Antifungal Activity, and Insecticidal Activity
Authors: Tabanca Nurhayat , Bernier Ulrich R. , Tsikolia Maia , Becnel James J. , Sampson Blair , Werle Chris , Demirci Betül , Başer Kemal Hüsnü Can , Blythe Eugene K. , Pounders Cecil , Wedge David E.
Published: March 2019

Natural plant extracts often contain compounds that are useful in pest management applications. The essential oil of Eupatorium capillifolium (dog-fennel) was investigated for antifungal and insecticidal activities. Essential oil obtained by hydrodistillation of aerial parts was analyzed by gas chromatography (GC) and gas chromatography–mass spectrometry (GC/MS). The major components were determined to be thymol methyl ether (=methyl thymol) (36.3%), 2,5-dimethoxy- p-cymene (20.8%) and myrcene (15.7%). Antifungal activity of the essential oil was weak against the plant pathogens Colletotrichum acutatum, C. fragariae, and C. gloeosporioides in direct bioautography assay. The E. capillifolium oil showed promising repellent activity against the yellow fever mosquito Aedes aegypti, whereas the oil exhibited moderate activity against the mosquito's first instar larvae in a high throughput bioassay. Topical applications of the oil showed no activity against the blood-feeding female adults of A. aegypti. Eupatorium capillifolium essential oil showed a linear dose response between adult lace bug ( Stephanitis pyrioides) mortality and increasing oil concentration in an adulticidal activity bioassay. The dog-fennel oil was more potent than the conventional insecticide malathion. In conclusion, these combined results showed Eupatorium capillifolium oil is a promising novel source of a biological insecticide with multiple modes of action.
Raman Optical Activity: A Powerful Technique to Investigate Essential Oil Components
Authors: Baranska Malgorzata , Chruszcz-Lipska Katarzyna
Published: March 2019

The theory and some applications of Raman Optical Activity (ROA) towards terpene analysis are presented. With this technique, vibrational optical activity from chiral molecules can be measured providing their absolute configuration. This short review provides data obtained for pinene, verbenone, menthol, camphor, carenes and related molecules. The ROA technique seems to be a powerful tool which permits correlation between the properties of biocompounds and their structure.
Comparison of Hydrodistillation and Headspace Solid-Phase Microextraction Techniques for Antibacterial Volatile Compounds from the Fruits of Seseli Libanotis
Authors: Skalicka–Wozniak Krystyna , Los Renata , Glowniak Kazimierz , Malm Anna
Published: March 2019

The volatile compounds from the fruits of Seseli libanotis, wild-growing in Poland, were obtained by hydrodistillation (HD) and headspace solid-phase microextraction techniques (HS-SPME) and analyzed using GC-MS. A total of 58 components were identified. The most abundant compounds were sabinen and β-phellandrene. MIC (minimal inhibitory concentration) and MBC (minimal bactericidal concentration) values for the essential oil against reference bacterial strains and clinical S. aureus isolates were determined. The essential oil showed better antibacterial activity against the Gram-positive bacteria (MICs between 0.15 to 1.25 mg/mL) when compared with Gram-negative bacteria (MICs between 1.25 to 2.5 mg/mL). The low values of the MBC/MIC ratio suggest that the examined oil behaved as a bactericidal agent.
Volatile Fraction of Lavender and Bitter Fennel Infusion Extracts
Authors: Tschiggerl Christine , Bucar Franz
Published: March 2019

The relative proportions of chemical classes (hydrocarbons, oxides, alcohols/ethers, aldehydes/ketones, acids/esters/lactones) in the essential oil of lavender ( Lavendula Angustifolia Mill., family Lamiaceae) and bitter fennel ( Foeniculum vulgare Mill. subsp. vulgare var. vulgare (Mill.) Thellung, family Apiaceae) and in the volatile fraction of infusion extracts were examined and showed remarkable differences.

The volatile compounds of infusions were isolated by hydrodistillation and solid phase extraction (SPE). Their qualitative and semiquantitative compositions were compared with the essential oil isolated by hydrodistillation directly from the plant material and analyzed by GC-MS. Furthermore, quantification of the major constituents of lavender oil and of the volatile fraction obtained by hydrodistillation of the infusion was performed.

Comparison of the total essential oil yield quantified by hydrodistillation of the lavender infusion (0.7% v/w, corresponding to plant material) with the essential oil yield of the blossoms (5.1% v/w) revealed that only 13.9% of the initial oil could be extracted by infusion. The main constituents of the volatile fraction of the lavender infusion were (hydrodistillation/SPE): linalool (39.3%/28.2%), 1,8 cineole (24.8%/18.9%), cis-linalool oxide (furanoid) (5.8%/8.0%), trans-linalool oxide (furanoid) (4.1%/7.1%), camphor (5.3%/4.0%) and α-terpineol (4.0%/3.0%). The major constituents of lavender essential oil were linalool (28.8%), 1,8-cineole (18.05%), linalyl acetate (13.9%) and α-terpineol (4.0%). Most intriguing, in the volatile fraction of lavender infusion a significant proportional decrease of linalyl acetate and an increase of linalool oxides was recognized.

The essential oil yield of fennel fruits was 12.5% v/w, whereas 1.8% v/w volatile fraction (corresponding to plant material) was obtained by hydrodistillation of the fennel infusion, which is equivalent to 14.5% of the initial fennel essential oil. The main constituents of the volatile fraction of the fennel infusion were (hydrodistillation/SPE): trans-anethole (56.4%/54.8%), fenchone (36.2%/39.5%) and estragole (2.5%/2.2%), which were also the major compounds of the genuine bitter fennel essential oil. In infusions, the proportion of ethers vs. ketones was shifted significantly towards a higher proportion of the latter compared with the essential oil obtained from the fruits.
Can Glandular Hair Density be a Breeding Marker for Origanum Vulgare subsp. Hirtum with High Essential Oil Content?
Authors: Szabó Krisztina , Sárosi Szilvia , Cserháti Beatrix , Ferenczy Antal
Published: March 2019

Origanum vulgare subsp. hirtum (Link) Ietswaart is an essential oil rich plant traditionally used as oregano. Based on the interest of the essential oil producing sector, in 2000 we have started a breeding program of O. vulgare subsp. hirtum. Plant material for our breeding work consists of 6 progeny. Individual evaluation of the plant material was carried out in 2008-2009 with the primary aim of finding mother plants with appropriate morphological features, high essential oil content (>7%) and with carvacrol as the main essential oil component. Among the survey of morphological characteristics special attention was given to glandular hair density in order to test the usability of it as a morphological marker for screening progeny for high essential oil content. The characteristics of the progeny can be described with high variability ensuring the possibility of a good selection base. Evaluating the morphology, essential oil content and constitution of the individuals, 20 plants were selected on the grounds of their high (7-8.6%) essential oil content, high ratio (70-93%) of carvacrol in the essential oil and typical morphological features of O. vulgare subsp. hirtum. From the results of glandular hair density it can be stated that the correlation between glandular hair density of the upper, middle and lower leaves either on vegetative or generative shoots and essential oil content was never strong enough (correlation coefficient ≤ 0.5) to use it exclusively as a morphological marker for individual selection.
Xenobiotic Biotransformation of 4-Methoxy-N-methyl-2-quinolone, Isolated from Zanthoxylum Monophyllum
Authors: Rodríguez-Guzmán Raquel , Radwan Mohamed M. , Burandt Charles L. , Williamson John S. , Ross Samir A.
Published: March 2019

Phytochemical evaluation of Zanthoxylum monophyllum has led to the isolation of the alkaloid 4-methoxy- N-methyl-2-quinolone (1) with a significant activity against methicillin-resistant Staphylococcus aureus (MRSA), with an IC50 value of 1.5 (μg /mL. Xenobiotic biotransformation of 1 has been conducted with the general goal of increasing the bioactivity of the compound and contributing new leads for further pharmacological research. Twenty-nine microorganisms were used for screening and two ( Aspergillus flavus and Cunninghamella echinulata var.echinulata) were able to transform compound 1 to 4-methoxy-2-quinolone (2). Structural identification of the compounds was based on NMR, IR, and MS data.
Antibacterial and Antifungal Screening of Centaurium Pulchellum Crude Extracts and Main Secoiridoid Compounds
Authors: Šiler Branislav , Mišić Danijela , Nestorović Jasmina , Banjanac Tijana , Glamočlija Jasmina , Soković Marina , Ćirić Ana
Published: March 2019

The main principles of C. pulchellum (Sw.) Druce, secoiridoid glycosides, have been studied as potent bioactive compounds. Here we scored their content in extracts of ten populations of this species. Antibacterial and antifungal assays of the extracts and pure secoiridoid glycosides were performed against eight bacterial strains and five fungal species. Methanol extracts from both aerial parts and roots exhibited excellent antibacterial (0.05-0.2 mg mL−1) and very good antifungal (0.1-2 mg mL−1) activity. Pure secoiridoid glycosides isolated from these extracts demonstrated very strong antibacterial (0.01-0.04 mg mL−1) and especially antifungal (0.001-0.1 mg mL−1) activity.
Bioactive Clerodane Diterpenes from Roots of Carex Distachya
Authors: Fiorentino Antonio , D'Abrosca Brigida , Pacifico Severina , Izzo Angelina , D'Angelo Grazia , Monaco Pietro
Published: March 2019

Two new clerodane diterpenes were isolated from roots of Carex distachya Desf., a perennial plant widely distributed in the coastal area of the Mediterranean basin. Chemical characterization of the metabolites was carried out mainly by 1D and 2D NMR spectroscopy. The isolated compounds influenced either positively or negatively the plant growth (root and shoot elongation) of three coexisting herbaceous species.
Analysis of MS/MS Fragmentation of Taxoids
Authors: Morikawa Kouhei , Tanaka Ken , Li Feng , Awale Suresh , Tezuka Yasuhiro , Nobukawa Takahiro , Kadota Shigetoshi
Published: March 2019

The fragmentation pathways of seven types of taxoids were investigated by using a LC-MS/MS method, namely: (1) neutral taxoids with a C-4(20) double bond; (2) taxoids with a C-4(20) double bond and oxygenation at C-14; (3) 5-cinnamoyl taxoids with a C-4(20) double bond; (4) a basic taxoid with a C-4(20) double bond; (5) a taxoid with a C-4(20) epoxide; (6) taxoids with an oxetane ring; and (7) taxoids with an oxetane ring and a phenylisoserine C-13 side chain. Depending on the class of core structure and the substitution pattern, each taxoid gave either the molecular adduct ion [M+NH4]+ or [M+H]+. In the MS/MS, the molecular adduct ion gave characteristic product ions corresponding to the loss of water, acetic acid, benzoic acid, and cinnamic acid or the phenylisoserine group. These could reflect the difference of the substitutions and structural modifications and should be utilized for the structure elucidation of taxoids by LC-MS.
New Hopane Triterpenes and Antioxidant Constituents from Potentilla Fulgens
Authors: Jaitak Vikas , Kaul Vijay K. , Himlata  , Kumar Neeraj , Singh Bikram , Dhar Jyoti , Sharma Om P.
Published: March 2019

Phytochemical investigation of the aerial parts of Potentilla fulgens L. led to the isolation of two new triterpenes, potentene A (1) and potentene B (2). In addition, three known compounds afzelchin–4α→8″–catechin (3), epiafzelchin (4) and rutin (5) were isolated. The structures of all these compounds were elucidated by extensive spectroscopic and chemical evidence. Compounds 3, 4, and 5 exhibited significant 1,1, diphenyl-2-picrylhydrazyl radical scavenging activity, with IC50 values of 1.21, 2.88 and 5.20 mg/mL, respectively; the known standard antioxidant, vitamin C, had a value of 0.44 mg/mL.
Cytotoxic Evaluation of Semisynthetic Ester and Amide Derivatives of Oleanolic Acid
Authors: Gupta Shikha , Kalani Komal , Saxena Mohit , Srivastava Santosh K. , Agrawal Satyam K. , Suri Nitasha , Saxena Ajit K.
Published: March 2019

Although a number of chemicals have been isolated from Lantana Camara, only a few have been evaluated for their biological significance. As part of our drug discovery program for cytotoxic agents from Indian medicinal plants, roots of L. camara L. were chemically investigated, which resulted in the isolation and identification of a cytotoxic agent, oleanolic acid (1b) as a major constituent. Oleanolic acid was converted into six semisynthetic ester (2-7) and seven amide (8-14) derivatives. The ester derivatives (2-7) showed 3-6 times more selective activity than 1b against the human ovarian cancer cell line (IGR-OV-1), while amide derivatives 8-14 showed 16-53 times more selective activity against the human lung cancer cell line (HOP-62). Structure activity relationship within the ester (2-7) and amide (8-14) derivatives are discussed.
Two Ring-A-Aromatized Bile Acids from the Marine Sponge Sollasella Moretonensis
Authors: Lu Zhenyu , Van Wagoner Ryan M. , Harper Mary Kay , Hooper John N. A. , Ireland Chris M.
Published: March 2019

Two ring-A-aromatized bile acids, 1 and 2, were isolated from the sponge Sollasella moretonensis, collected from the seabed of northern Queensland. Structures were assigned on the basis of extensive 1D and 2D NMR studies, as well as analysis by HRESIMS. Compound 2 has previously been produced synthetically, though this marks its first isolation from a natural source.
Cytotoxic Thiocarbamate Derivatives of Boldine
Authors: Thomet Franz A. , Pinyol Pablo , Villena Joan , Espinoza Luis J. , Reveco Patricio G.
Published: March 2019

Two new boldine derivatives: the 3-thiocarbamateboldine (3) and the 2,9 -O,O-diacetyl-3-thiocarbamateboldine (4) have been synthesized and their cytotoxicity evaluated.
Synthesis of Fluorescent Analogues of the Anticancer Natural Products 4-Hydroxyphenylmethylene Hydantoin and δ-Tocotrienol
Authors: Mudit Mudit , Behery Fathy A. , Wali Vikram B. , Sylvester Paul W. , El Sayed Khalid A.
Published: March 2019

4-Hydroxyphenylmethylene hydantoin (PMH, 1), isolated from the Red Sea sponge Hemimycale Arabica, and δ-tocotrienol (3), isolated from the tocotrienol-rich fraction of palm oil, are important antimetastatic and antiproliferative natural products that proved effective against metastatic prostate and breast cancers, respectively. New fluorescent derivatives of PMH (2) and δ-tocotrienol (4) were synthesized by Steglich esterification. Both 2 and 4 retained good anti-migratory and antiproliferative activities, respectively. Fluorescent analogues 2 and 4 can be used for the identification of molecular targets of 1 and 3 in tumor cell cultures.
Two Pairs of Enantiomeric Neolignans from Lobelia Chinensis
Authors: Chen Jian-Xin , Huang Shen-Hui , Wang Lei , Han Wei-Li , Wang Ying , Zhang Dong-Mei , Ye Wen-Cai
Published: March 2019

A pair of new enantiomeric neolignans, ethyl 3-[(2 R,3 S)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl] propanoate (+) (1) and ethyl 3-[(2 S,3 R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl] propanoate (-) (1), together with a pair of known enantiomeric neolignans (+) (2) and (-) (2), as well as five known lignans (3-7) were isolated from the ethanol extract of Lobelia chinensis. Their structures were elucidated on the basis of extensive spectroscopic analyses, including 1D and 2D NMR, HR-ESIMS and CD spectra.
Evaluation and Discrimination of Cortex Magnoliae Officinalis Produced in Zhejiang Province (Wen-Hou-Po) by UPLC-DAD-TOF-MS Fingerprint
Authors: Wang Lin , Yuan Ke , Yu Wei-Wu , Wang Jing
Published: March 2019

An ultra performance liquid chromatography tandem TOF mass spectrometric (UPLC-DAD-TOF-MS) fingerprinting method was developed for the quality control and source discrimination of Cortex magnoliae officinalis produced in Zhejiang Province (Wen-Hou-Po). Twelve samples of Wen-Hou-Po collected from two species in five areas in Zhejiang Province of China were used to establish the fingerprint. Data were evaluated statistically using similarity analysis, hierarchical cluster analysis (HCA) and discriminant analysis (DA) in order to establish a similarity standard of fingerprint for quality control of Wen-Hou-Po, then to classify the Wen-Hou-Po samples and to identify key categorizing parameters. The similarity indexes were all above 0.95 between the reference chromatogram and that of each sample. By comparing the UV and MS data with those of the authentic standards and literature, nine main peaks in the fingerprints were identified. The result of hierarchical cluster analysis showed that the samples from two species in five areas could be divided into two distinct groups (the same as the groups of the samples divided by their species) based on their compositional fingerprints. A rapid and convenient discriminant function was then established to discriminate the species of unknown Wen-Hou-Po, and the cross validation result was 100%. In this study, the methods established are reliable, and could be used to evaluate the quality and to identify the species of Wen-Hou-Po in the future.
Volatile Components of Centaurea Bracteata and C. Pannonica subsp. Pannonica growing wild in Croatia
Authors: Formisano Carmen , Senatore Felice , Bancheva Svetlana , Bruno Maurizio , Maggio Antonella , Rosselli Sergio
Published: March 2019

This paper reports on the volatile components of oils from the aerial parts (CBA) and roots (CBR) of Centaurea bracteata Scop. and aerial parts of C. pannonica (Heuffel) Simonkai subsp. pannonica (CPA), two Asteraceae growing wild in Croatia. The volatile components, obtained by hydrodistillation, were determined by GC-MS analysis. The yields (w/w) of the dried oils were 0.10% (CBA), 0.22% (CBR) and 0.09% (CPA), respectively. A total of 91 compounds were identified accounting for 91.1%, 93.3% and 87.9% of the total oil for CBA, CBR and CPA, respectively. All the samples were characterized mainly by hydrocarbons (7.1-34.1%), fatty acids (9.7-45.9%), and oxygenated sesquiterpenes (15.2-16.6%). The major components of the samples were hexadecanoic acid (8.1-31.1%), nonacosane (0.6-13.4%) and caryophyllene oxide (4.5-11.9%). Monoterpenes, both hydrocarbons and oxygenated, were either absent or present in low amounts in all the oils. The similarity in the oil contents is consistent with the two species being placed in the same section, Jacea.
GC/MS Analysis and Antimicrobial Activity of the Essential Oil of Fresh Leaves of Eucalytus Globulus, and Leaves and Stems of Smyrnium Olusatrum from Constantine (Algeria)
Authors: Daroui-Mokaddem Habiba , Kabouche Ahmed , Bouacha Mabrouka , Soumati Boudjemaa , El-Azzouny Aida , Bruneau Christian , Kabouche Zahia
Published: March 2019

The essential oils of fresh leaves of Eucalyptus globulus L. (Myrtaceae), and leaves and stems of Smyrnium olusatrum L. (Apiaceae), obtained by hydrodistillation in a Clevenger-type apparatus, were analyzed by GC/MS. Twenty compounds were characterized, representing 98.3% of the essential oil of E. globulus, with 1,8-cineole (48.6%), globulol (10.9%), trans-pinocarveol (10.7%), and α-terpineol (6.6%) as main components, while thirty-three compounds were characterized, representing 94.3% of the essential oil of S. olusatrum, with sabinene (27.1%), curzerene (13.7%), methyl-1-benzyl-2-oxocyclooctane carboxylate (12.3%), α-pinene (7.2%), cryptone (7.1%) and β-pinene (5.7%) as the major components. The essential oils of E. globulus and S. olusatrum were tested against a wide range of fungal and bacterial strains. Both oils showed significant antimicrobial activity.
Alkaline Phosphatase (ALP) Enhancing Iridoid Glucosides from the Indonesian Medicinal Plant Barleria Lupulina
Authors: Widyowati Retno , Tezuka Yasuhiro , Miyahara Tatsurou , Awale Suresh , Kadota Shigetoshi
Published: March 2019

In order to find antiosteoporotic agents from natural resources, 32 Indonesian medicinal plants were screened for their effects on osteoblast differentiation by using alkaline phosphatase (ALP) activity in MC3T3-E1 osteoblast cells as a marker. From the extract of Barleria lupulina, which showed the most potent activity, 13 iridoid glucosides, including three new ones [8- O-acetylipolamiidic acid (1), 8- O-acetyl-6- O-( p-methoxy- cis-cinnamoyl)shanzhiside (2), and 8- O-acetyl-6- O-( p-methoxy- trans-cinnamoyl)shanzhiside (3)] were identified. Among the 13 iridoid glucosides, ipolamiide (4) showed the most potent activity in a dose-dependent manner.
Two New Sesquiterpenes from Sarcandra Glabra
Authors: Oanh Do Thi , Ky Pham Thanh , Hang Nguyen Thi Bich , Yen Pham Hai , Hanh Tran Hong , Cuong Nguyen Xuan , Vu Luong Dang , Van Minh Chau , Van Kiem Phan
Published: March 2019

Phytochemical study of the ethanol extract of Sarcandra glabra resulted in the isolation of two new sesquiterpenes, glabranols A (1) and B (2). Their structures were elucidated as 8α,9α,15-trihydroxylinden-4,7(11)-dien-12,8β-olide (1) and 1β,4α,7β,11-tetrahydroxyeudesmane (2), by spectroscopic methods including 1D- and 2D-NMR and FTICR-MS.
New Acyclic Diterpenic Acids from Yacon (Smallanthus Sonchifolius) Leaves
Authors: Mercado María I. , Aráoz María V. Coll , Grau Alfredo , Catalán César A. N.
Published: March 2019

Two new acyclic diterpenoids, smaditerpenic acid E (1a) and F (2a), along with nineteen melampolide-type sesquiterpene lactones, six of them not previously reported in yacon, were isolated from the methylene chloride leaf rinse extract. Their structures were elucidated from 1D and 2D NMR experiments and gas chromatography coupled to mass spectrometry.
Chemical Composition of Natural Colophony from Pinus Brutia and Comparison with Synthetic Colophony
Authors: Gören Ahmet C. , Bilsel Gökhan , Öztürk Alp Hakan , Topçu Gulaçtı
Published: March 2019

The compositions of colophony resins obtained from Pinus brutia Ten trees by three different methods (acid paste, carved hole and scraping) from Ayvacık, Gökova and Kemalpaşa in Turkey were analyzed by capillary GC-MS. The main components were the monoterpenes α-pinene, β-pinene, and Δ3-carene, and the diterpenic resin acids palustric, abietic, kaur-9(11)-16-en-18-oic and neoabietic acid. The synthetic colophony resins exhibited similar contents to those of the natural resins obtained from the Gökova and Kemalpaşa regions of Turkey. However, colophony resins from Ayvacık exhibited only half the diterpenic acid content as those of the Gökova and Kemalpaşa resins. Out of the three techniques, the carved hole method caused rather different percentages in the constituents of the essential oils.
Alkaloidal Constituents of Tinospora Crispa
Authors: Choudhary M. Iqbal , Ismail Muhammad , Ali Zulfiqar , Shaari Khozirah , Lajis Nordin H. , Atta-ur-Rahman
Published: March 2019

Phytochemical investigations of the stems of Tinospora crispa led to the isolation of one new aporphine alkaloid, N-formylasimilobine 2- O-β-D-glucopyranoside (1), along with six known alkaloids, N-formylasimilobine 2- O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside (2) (tinoscorside A), N-formylanonaine (3), N-formyldehydroanonaine (4), N-formylnornuciferine (5), N-demethyl -N-formyldehydronornuciferine (6), magnoflorine (7), paprazine (8), N-trans-feruloyltyramine (9), and cytidine (10). The structure of new compound 1 was deduced on the basis of spectroscopic data.
Acetylcholinesterase and Butyrylcholinesterase Inhibitory Compounds from Chelidonium Majus (Papaveraceae)
Authors: Cahlíková Lucie , Opletal Lubomír , Kurfürst Milan , Macáková Kateřina , Kulhánková Andrea , Hošt'álková Anna
Published: March 2019

The roots and aerial parts of Chelidonium majus L. were extracted with EtOH and fractionated using CHCl3 and EtOH. Repeated column chromatography, preparative TLC and crystallization led to the isolation of five isoquinoline alkaloids, stylopine (3), chelidonine (4), homochelidonine (5), protopine (6), and allocryptopine (7), along with two isolation artifacts 6-ethoxydihydrosanguinarine (1) and 6-ethoxydihydrochelerythrine (2). All isolated compounds were tested for human blood acetylcholinesterase (HuAChE) and human plasma butyrylcholinesterase (HuBuChE) inhibitory activity. The isolation artifacts exhibited the highest activity against HuAChE and HuBuChE with IC50 values of 0.83 ± 0.04 μM and 4.20 ± 0.19 μM for 6-ethoxydihydrochelerythrine and 3.25 ± 0.24 μM and 4.51 ± 0.31 μM for 6-ethoxydihydrosanguinarine. The most active of the naturally-occurring alkaloids was chelidonine, which inhibited both HuAChE and HuBuChE in a dose-dependent manner with IC50 values of 26.8 ± 1.2 μM and 31.9 ± 1.4 μM, respectively.
DPPH-Scavenging Activities and Structure-Activity Relationships of Phenolic Compounds
Authors: Zheng Cheng-Dong , Li Gang , Li Hu-Qiang , Xu Xiao-Jing , Gao Jin-Ming , Zhang An-Ling
Published: March 2019

Thirty-eight phenolic compounds (including 31 flavonoids) were examined for their DPPH radical-scavenging activities, and structure-activity relationships were evaluated. Specifically, the presence of an Ortho-dihydroxyl structure in phenolics is largely responsible for their excellent antiradical activity. 3-Hydroxyl was also essential to generate a high radical-scavenging activity. An increasing number of hydroxyls on flavones with a 3′,4′-dihydroxyl basic structure, the presence of a third hydroxyl group at C-5′, a phloroglucinol structure, glycosylation and methylation of the hydroxyls, and some other hydroxyls, for example 5-, and 7-hydroxyl in ring A, decreased the radical-scavenging activities of flavonoids and other phenolics.
RP-HPLC Analysis of Jirakadyarishta and Chemical Changes during Fermentation
Authors: Lal Uma Ranjan , Tripathi Shailendra Mani , Jachak Sanjay M. , Bhutani Kamlesh Kumar , Singh Inder Pal
Published: March 2019

Jirakadyarishta, an Ayurvedic formulation prepared by the fermentation of a decoction of Cuminum cyminum (seeds) is traditionally used for intestinal disorders. RP-HPLC analysis of the decoction and the final processed formulation revealed that apigenin-7- O-[galacturonide (1→4)- O-glucoside] and luteolin-4′- O-glucoside-7- O-galacturonide) were the two major constituents of the decoction of C. cyminum. Selective hydrolysis of 7 -O-glucosides of luteolin and apigenin during fermentation resulted in an increase in the amount of luteolin and apigenin. The 4′- O-glucoside-7- O-galacturonide of luteolin and galacturonide derivative of apigenin were not hydrolyzed during fermentation. Monomeric phenolics, together with 5-hydroxymethyl furfural (5-HMF), were also introduced into the formulation through the jaggery and other plant materials during fermentation. This communication highlights the importance of the ancient processing methods used in Ayurveda.
A New Biisoflavonoid from the Roots of Erythrina Variegata
Authors: Tanaka Hitoshi , Sudo Masaru , Hirata Miyuki , Etoh Hideo , Sato Masaru , Yamaguchi Ryozo , Sakai Eiji , Chen Ih-Sheng , Fukai Toshio
Published: March 2019

A new biisoflavonoid, biseryvarin A (1a), together with two known compounds were isolated from the roots of Erythrina variegata. The structure of biseryvarin A was established on the basis of spectroscopic evidence. Biseryvarin A is the first dimeric isoflavonoid possessing isoprenoid groups from the genus Erythrina. Biseryvarin A showed low activity against methicillin-resistant Staphylococcus aureus (MRSA).
Chemical Constituents of Nepeta Distans
Authors: Hussain Javid , Bukhari Nausheen , Hussain Hidayat , Rehman Najeeb U , Hussain Syed Murtaza
Published: March 2019

Phytochemical investigation of Nepeta distans Raul resulted in the isolation of a new phenolic compound, nepatanol (1), and eight known compounds, markhamioside F, netidiol, nepedinol, thymoquinone, eugenol, oleanolic acid, ursolic acid, and β-sitosterol, which have been isolated for the first time from this source. Structures of all the isolates were established on the basis of MS, and 1D and 2D NMR spectral data and by comparison with reported data.
(-)-Sclerotiorin from an Unidentified Marine Fungus as an Anti-meiotic and Antifungal Agent
Authors: Bao Li , Xu Zhenyu , Niu Shu-bin , Namikoshi Michio , Kobayashi Hisayoshi , Liu Hong-wei
Published: March 2019

(-)-Sclerotiorin, isolated and purified from the fermented broth of an unidentified marine fungus (98F134), inhibited the maturation of starfish oocytes induced by 1-methyl adenine with an IC50 value of 0.50 μM. (-)-Sclerotiorin also showed antifungal activity against Saccharomyces Cerevisiae, Aspergilus Fumigatus, Alternaria Longipes, Piricularia Oryzae, Verticillium Albo-Atrum, Fusarium Culmorum, and F. nivale with IC50 values less than 20 μg/mL.
Mitregenin, a New Annonaceous Acetogenin from Mitrephora Maingayi
Authors: Zhang Qiang , Di Ying-Tong , He Hong-Ping , Li Shun-Lin , Hao Xiao-Jiang
Published: March 2019

From Mitrephora maingayi, a new C21-type Annonaceous acetogenin (1) has been isolated, along with a biogenetically related known compound, oropheic acid (2). Their structures were elucidated on the basis of extensive spectroscopic analysis. The insecticidal activity of 1 was also assessed.
Long Argan Fruit Drying Time is Detrimental for Argan Oil Quality
Authors: Harhar Hicham , Gharby Saïd , Kartah Badr Eddine , El Monfalouti Hanae , Charrouf Zoubida , Guillaume Dom
Published: March 2019

Argan oil is extracted from the kernels of argan fruits that have been sun-dried for either a few days or up to several weeks. The influence of the fruit drying time on the quantity, quality, and preservation of solvent-extracted argan oil was compared with press-extracted argan oil. Quantitatively, the time necessary for efficient fruit peeling and the amount of extracted oil were determined with regard to the fruit drying time (0 to 28 days). Argan oil quality was studied using, as markers, moisture content, specific extinction, acid index, peroxide index, fatty acid composition, and Rancimat oxidative stability. Oil from fresh fruit presents a high moisture content, high acidity and peroxide values, and short shelf life. Ten to fourteen days of sun-drying is optimum to obtain high quality argan oil.
Volatile Constituents of Different Parts of Smyrnium Olusatrum from Greece
Authors: Papaioannou Fotini , Koutsaviti Aikaterini , Tzakou Olga
Published: March 2019

The essential oils from stems, leaves, inflorescences, and both unripe and ripe infructescences of Smyrnium olusatrum L. (Umbelliferae) collected in Greece were obtained by hydrodistillation and analyzed by GC-FID and GC-MS. Fifty-eight components were identified. Among the samples analyzed, the differences observed were mainly quantitative. All oils were characterized by the abundance of sesquiterpenes. The major components of the stem and leaf oils were furanoeremophil-1-one (54.3% and 28.7%, respectively) and curzerene (18.8%, 29.0%). The main constituents of the inflorescence oil were curzerene (38.1%), germacrone (20.2%) and furanoeremophil-1-one (20.0%), while those of the unripe and ripe infructescence oils were 1β-acetoxy-furanoeudesm-4(15)-ene (22.1%, 30.8%) and curzerene (29.7%, 17.4%).
Insecticidal Activity against Bemisia Tabaci Biotype B of Peel Essential Oil of Citrus sinensis var. pear and Citrus aurantium Cultivated in Northeast Brazil
Authors: de Carvalho Ribeiro Nicolle , da Camara Claudio Augusto Gomes , de Souza Born Flávia , de Siqueira Herbert Álvaro Abreu
Published: March 2019

The fumigant action of peel essential oils of Citrus sinensis var. pear (pear orange = PO) and C. aurantium (bitter orange = BO) from the northeast of Brazil were evaluated against Bemisia tabaci biotype B and compared with eugenol as a positive control. The oil concentration in the PO at 8.5 μL/L of air caused 97% mortality, while the oil concentration of BO at 9.5 μL/L of air caused 99% mortality. However, the LC50 estimates for both oils (LC50 = 3.80 μL/L of air for PO and LC50 = 5.80 μL/L of air for BO) did not differ from each other, but they did when compared with eugenol (LC50 = 0.20 μL/L of air). Regarding their effects on oviposition, the Citrus oils showed concentration-response dependence, reducing the number of eggs as the concentration increased, which was not observed for eugenol. The minimum concentrations of the oils that caused a significant reduction in the egg lay were 3.5 and 7.0 μL/L of air for BO and PO, respectively. These results suggest that oils from PO and BO peels may be promising as models to develop new insecticides that might be applied into the integrated management of whiteflies.
Antioxidant Activity and Chemical Composition of Essential Oil from Atriplex Undulata
Authors: Rodriguez Silvana A. , Murray Ana P.
Published: March 2019

The essential oil from aerial parts (stems and leaves) of Atriplex undulata (Moq) D. Dietr. (Chenopodiaceae) has been studied for its in vitro antioxidant activity. The chemical composition of the oil obtained by hydrodistillation was determined by GC and GC-MS. The major constituents were p-acetanisole (28.1%), β-damascenone (9.3%), β-ionone (5.1%), viridiflorene (4.7%) and 3-oxo-α-ionol (2.2%). The antioxidant activity of the oil was determined by two methods: Crocin bleaching inhibition (Krel= 0.72 ± 0.15) and scavenging of the DPPH radical (IC50 = 36.2 ± 1.6 μg/mL). The presence of active compounds like p-acetanisole, carvone, vanillin, 4-vinylguaiacol, guaiacol, terpinen-4-ol and α- terpineol could explain the antioxidant activity observed for this oil.
Immunomodulatory Action of Monosulfated Triterpene Glycosides from the Sea Cucumber Cucumaria okhotensis: Stimulation of Activity of Mouse Peritoneal Macrophages
Authors: Aminin Dmitry L. , Silchenko Alexandra S. , Avilov Sergey A. , Stepanov Vadim G. , Kalinin Vladimir I.
Published: March 2019

Six monosulfated triterpene glycosides, frondoside A1 (1), okhotoside B1 (2), okhotoside A1-1 (3), frondoside A (4), okhotoside A2-1 (5) and cucumarioside A2-5 (6), isolated from Cucumaria okhotensis Levin et Stepanov, stimulate spreading and lysosomal activity of mouse macrophages and ROS-formation in the macrophages. The highest macrophage spreading and stimulation of their lysosomal activity was induced by glycosides 1, 4 and 6. All glycosides similarly stimulate ROS formation in macrophages, but glycoside 2 caused minimal stimulation.
Isolation and Characterization of Crotosparsamide, a New Cyclic Nonapeptide from Croton sparsiflorus
Authors: Mehmood Rashad , Malik Abdul
Published: March 2019

Crotosparsamide (1), a new cyclic nonapeptide, has been isolated from the n-butanol soluble sub-fraction of Croton sparsiflorus along with p-hydroxy methylcinnamate and kaempferol, which are reported for the first time from this species. Their structures were determined by chemical and spectral studies including ESIMS, and 1D and 2D NMR spectroscopic data.
Two New Lavandulyl Flavonoids from Sophora flavescens
Authors: Liu Dan , Xin Xiulan , Su Dong-hai , Liu Junying , Wei Qing , Li Bo , Cui Jian
Published: March 2019

Two novel lavandulyl flavonoids, (2 S)-7-methoxyl-4″, 5″ -dihydroxynorkurarinone (1) and (2 S)-6″ -hydroxynorkurarinone-7- O-β-D-galactoside (2), were isolated from the rhizome of Sophora flavescens. Their structures were elucidated by spectral methods, including 2D NMR spectroscopy. Both compounds showed cytotoxic activity against Hela cells, with 2 being more active than 1.
Biotransformation of Naringenin to Eriodictyol by Saccharomyces cerevisiea Functionally Expressing Flavonoid 3′ Hydroxylase
Authors: Amor Ilef Limem-Ben , Hehn Alain , Guedon Emmanuel , Ghedira Kamel , Engasser Jean-Marc , Chekir-Ghedrira Leila , Ghoul Mohamed
Published: March 2019

To increase the biological activities of flavonoids and to enhance their stability and solubility by functionalization reactions (polymerization, esterification, alkylation, glycosylation and acylation), an increase in the number of hydroxyl groups in these molecules is needed. Hydroxylation reactions may be achieved using either chemical or enzymatic methods, the latter being more highly specific than the former. In our study, the flavonoid 3′ hydroxylase (F3′H) from Gerbera hybrid, functionally expressed in Saccharomyces cerevisiae, was used to hydroxylate naringenin (the first flavonoid core synthesized in plants). Furthermore, we studied factors that may affect naringenin hydroxylation by recombinant cell-like yeast growth on selective or rich media and plasmid stability.

The whole recombinant cells hydroxylated naringenin at position 3′ to give eriodictyol. In a selective media, the yeast failed to grow to high cell densities (maximum 5 g/L), but the plasmid stability was nearly 90 %, and naringenin hydroxylation reached 100 %. In a rich complex media, the biomass reached 10 g/L, but the yield of naringenin hydroxylation reached only 71 %, and the plasmid stability decreased. When yeast functionally expressing F3′H from Gerbera hybrid was used, in a selective media, 200 mg/L of eriodictyol from naringenin was produced.
Two New 3-C-Carboxylated Flavones from the Rhizomes of Caragana conferta
Authors: Khan Rehan , Malik Abdul , Yasmeen Shazia , Afza Nighat
Published: March 2019

Confertins A (1) and B (2), new 3- C-carboxylated flavones, have been isolated from the ethyl acetate soluble fraction of the rhizomes of Caragana conferta. Their structures have been assigned on the basis of spectroscopic studies.
Kaempferol Glycosides in the Flowers of Carnation and their Contribution to the Creamy White Flower Color
Authors: Iwashina Tsukasa , Yamaguchi Masa-atsu , Nakayama Masayoshi , Onozaki Takashi , Yoshida Hiroyuki , Kawanobu Shuji , Ono Hiroshi , Okamura Masachika
Published: March 2019

Three flavonol glycosides were isolated from the flowers of carnation cultivars ‘White Wink’ and ‘Honey Moon’. They were identified from their UV, MS, 1H and 13C NMR spectra as kaempferol 3 -O-neohesperidoside, kaempferol 3 -O-sophoroside and kaempferol 3- O-glucosyl-(1→2)-[rhamnosyl-(1→6)-glucoside]. Referring to previous reports, flavonols occurring in carnation flowers are characterized as kaempferol 3- O-glucosides with additional sugars binding at the 2 and/or 6-positions of the glucose. The kaempferol glycoside contents of a nearly pure white flower and some creamy white flower lines were compared. Although the major glycoside was different in each line, the total kaempferol contents of the creamy white lines were from 5.9 to 20.9 times higher than the pure white line. Thus, in carnations, kaempferol glycosides surely contribute to the creamy tone of white flowers.
Factors Influencing Glabridin Stability
Authors: Ao Mingzhang , Shi Yue , Cui Yongming , Guo Wentao , Wang Jing , Yu Longjiang
Published: March 2019

Glabridin, a polyphenolic isoflavan of Glycyrrhiza glabra, has shown a variety of pharmaceutical properties. We have previously studied the isolation of glabridin using macroporous resin and found that it is partially degraded, giving a dark color. To illustrate the degradation of glabridin, the present work studied the stability of glabridin under various conditions. Licorice extract containing about 20% glabridin, obtained from G. glabra by silica gel column chromatography, was used in the stability study. Seven different factors (temperature, illumination, humidity, pH, solvent, oxygen, and oxidant) were studied and content changes were determined through HPLC analysis. Except for oxygen, all the above factors had an effect on the stability of glabridin, with illumination being the main one. Moreover, the interactions between temperature and pH, temperature and humidity, and illumination and pH can promote the degradation of glabridin. In conclusion, we suggest that a dark, dry and airtight environment provides the optimized condition for the long-term storage of glabridin.