bluuebunny/crossref_metadata_2025 huggingface dataset:
Jasminum sambac Flower Absolutes from India and China – Geographic Variations
Authors: Braun Norbert A. , Sim Sherina
Published: March 2019

Seven Jasminum sambac flower absolutes from different locations in the southern Indian state of Tamil Nadu were analyzed using GC and GC-MS. Focus was placed on 41 key ingredients to investigate geographic variations in this species. These seven absolutes were compared with an Indian bud absolute and commercially available J. sambac flower absolutes from India and China. All absolutes showed broad variations for the 10 main ingredients between 8% and 96%. In addition, the odor of Indian and Chinese J. sambac flower absolutes were assessed.
Investigation of the Volatile Constituents of Different Gynura Species from Two Chinese Origins by SPME/GC-MS
Authors: Chen Jian , Adams An , Mangelinckx Sven , Ren Bing-ru , Li Wei-lin , Wang Zheng-tao , De Kimpe Norbert
Published: March 2019

GC-MS analyses of the volatile constituents obtained by solid phase microextraction (SPME) of two Gynura species, i.e. G. divaricata and G. bicolor, collected from Nanjing and Nanping areas in the east of China, enabled the identification of more than 50 different components. Generally, a higher contents of sesquiterpene compounds such as β-caryophyllene, α-caryophyllene and α-copaene were found in G. bicolor than in G. divaricata, regardless of their origin. Qualitatively, the detected major volatiles of G. bicolor and G. divaricata originating from Nanjing were the same, i.e. β-caryophyllene, α-caryophyllene, α-copaene, α-pinene and β-pinene. The volatile profile of a third species, G. medica, also originating from Nanjing was different with sesquiterpenes γ-cadinene, β-caryophyllene, elixene and monoterpene limonene as the major components. The volatile profiles of G. bicolor and G. divaricata originating from Nanping were more diverse. For both species β-caryophyllene, α-copaene and limonene were the major volatiles, but G. bicolor also produced α-caryophyllene and carvone as major constituents, whereas for G. divariata o-cymene was detected. Overall, these results indicate that the biosynthesis of volatiles by Gynura species is not only species related, but is also possibly influenced by the local environmental conditions of growth.
Chemical Composition and Antibacterial Activity of the Essential Oil of Espeletia nana
Authors: Peña Alexis , Rojas Luis , Aparicio Rosa , Alarcón Libia , Baptista José Gregorio , Velasco Judith , Carmona Juan , Usubillaga Alfredo
Published: March 2019

The essential oil of the leaves of Espeletia nana Cuatrec, obtained by hydrodistillation, was analyzed by GC-MS, which allowed the identification of 24 components, which made up 99.9% of the oil. The most abundant compounds were α-pinene (38.1%), β-pinene (17.2%), myrcene (15.0%), spathulenol (4.2%), bicyclogermacrene (4.0%), α-zingiberene (4.0%), and γhimachalene (3.7%). Antibacterial activity was tested against Gram-positive and Gram-negative bacteria using the agar disk diffusion method. Activity was observed only against Gram-positive bacteria. MIC values were determined for Staphylococcus aureus ATCC 25923(200 μg/mL) and Enterococcus faecalis ATCC 29212 (600 μg/mL).
A Novel Isopimarane Diterpenoid with Acetylcholinesterase Inhibitory Activity from Nepeta sorgerae, an Endemic Species to the Nemrut Mountain
Authors: Yılmaz Anıl , Çağlar Pınar , Dirmenci Tuncay , Gören Nezhun , Topçu Gülaçtı
Published: March 2019

From the dichloromethane extract of Nepeta sorgerae, the isolation and structure elucidation are now reported of a new isopimarane diterpenoid, named sorgerolone, and two known triterpenoids, oleanolic acid and ursolic acid. Antioxidant activity of the extracts and the isolated terpenoids was determined by the DPPH free radical scavenging and lipid peroxidation inhibition (β-carotene bleaching) methods. Anticholinesterase activity of the extracts and isolates was investigated by Ellman's method against AChE and BChE enzymes. Although the antioxidant activity results were low, the AChE enzyme inhibition of the extracts and terpenoids was very promising.
New Indole Alkaloid from Peschiera affinis (Apocynaceae)
Authors: Santos Allana Kellen L. , Machado Luciana L. , Bizerra Ayla Marcia C. , Monte Francisco José Q. , Santiago Gilvandete M. P. , Braz-Filho Raimundo , Lemos Telma L. G.
Published: March 2019

A new indole alkaloid of the pyridocarbazole type, named 6 N-hydroxy-olivacine, and two known compounds, 2 N-oxide-olivacine and olivacine, were isolated from roots of Peschiera affinis. The structures of the compounds were determined by spectroscopic {IR and extensive NMR (COSY, HMQC, HMBC and NOESY)} and EIMS analysis.
A New Sesquiterpene from an Endophytic Aspergillus versicolor Strain
Authors: Liu Xiang-Hong , Miao Feng-Ping , Li Xiao-Dong , Yin Xiu-Li , Ji Nai-Yun
Published: March 2019

A new sesquiterpene, albican-11,14-diol (1), and seven known compounds, including sterigmatocystin (2), 3-hydroxy-5-(hydroxymethyl)-4-(4′-hydroxyphenoxy) pyrrolidin-2-one (3), (1 H-indol-3-yl) oxoacetamide (4), indole-3-carboxylic acid (5), indole-3-acetic acid (6), indole-3-carboxaldehyde (7), and volemolide (8), were isolated from the cultures of Aspergillus versicolor, an endophytic fungus isolated from the marine green alga Codium fragile. The structure of 1 was elucidated by 1D, 2D NMR and mass spectroscopic techniques. The bioassay results showed that 1 possessed potent activity against brine shrimp, Escherichia coli, and Staphyloccocus aureus.
Skin Permeation of Cacalol, Cacalone and 6-epi-Cacalone Sesquiterpenes from a Nanoemulsion
Authors: Garduño-Ramírez María Luisa , Clares Beatriz , Domínguez-Villegas Valeri , Peraire Concepción , Ruiz María Adolfina , García María Luisa , Calpena Ana C.
Published: March 2019

The objective of the present study was to investigate the transdermal permeation of cacalol (1) and a mixture of cacalone (2) and 6- epi-cacalone (3) in comparison with diclofenac acid (4) delivered from the same characterized nanoemulsion using Franz diffusion cells (formulae I, II and III). Results show that de Kp, J, Q24, P1 and P2 were higher for the acid diclofenac nanoemulsion than for the natural products nanoemulsions. As for the differences between the formulations I and II, with the natural products, Q24, the quantity extracted from skin and P2 were higher in the mixture of 2 and 3 nanoemulsion compared with the corresponding nanoemulsion of 1. In conclusion, the low permeability of the natural products nanoemulsions in comparison with that of diclofenac acid has the potential for development for drugs with local and systemic applications, respectively.
Ixoroid: A New Triterpenoid from the Flowers of Ixora coccinea
Authors: Versiani Muhammad Ali , Ikram Ambreen , Khalid Salman , Faizi Shaheen , Tahiri Iftikhar Ahmed
Published: March 2019

A new natural terpenoid, ixoroid (1), was isolated from the flower of Ixora coccinea, along with the known constituents stigmast-5-en-3- O-β-D-glucoside (2), 5- O-caffeoylquinic acid (3) and D-mannitol (4). The structure of ixoroid was elucidated on the basis of extensive 1D- and 2D-NMR studies and mass spectrometry as 21,23-epoxy-tirucall-7-en-3β-ol (1).
Corylucinine, a new Alkaloid from Corydalis cava (Fumariaceae), and its Cholinesterase Activity
Authors: Novák Zdeněk , Chlebek Jakub , Opletal Lubomír , Jiroš Pavel , Macáková Kateřina , Kuneš Jiří , Cahlíková Lucie
Published: March 2019

A new benzyldihydroisoquinoline alkaloid (1) was isolated from the tubers of Corydalis cava and named corylucinine. Additionally, 8-trichloromethyl-7,8-dihydropalmatine (2), an isolation artifact of tetrahydropalmatine, was obtained. The structures were established by spectroscopic (including 2D NMR and optical rotation) and HR-ESI-MS methods. Both compounds were tested for human blood acetylcholinesterase (HuAChE) and human plasma butyrylcholinesterase (HuBuChE) inhibitory activity. In comparison with the used standards, both compounds showed only moderate inhibitory activity against HuAChE (IC50, HuAChE = 127.6 ± 5.2 μM for 1, and IC50, HuAChE = 82.9 ± 3.9 μM for 2) and none against HuBuChE.
Inhibitory Effect of Hexahydrocurcumin on Human Platelet Aggregation
Authors: Dong Huei-Ping , Yang Rei-Cheng , Chunag I-Chun , Huang Li-Ju , Li Hsing-Tan , Chen Hsin-Liang , Chen Chung-Yi
Published: March 2019

The effects of hexahydrocurcumin on adenosine diphosphate (ADP)-induced human platelet aggregation were studied. Treatment of human platelet-rich plasma with hexahydrocurcumin resulted in an inhibitory effect on platelet aggregation, suggesting the potential of this compound as an anti-atherosclerogenic agent in humans.
Antihyperglycemic agents from Ammannia multiflora
Authors: Upadhyay Harish C. , Jaiswal Natasha , Tamrakar Akhilesh K. , Srivastava Arvind K. , Gupta Namita , Srivastava Santosh K.
Published: March 2019

The serial chromatographic separation of chloroform and n-butanol fractions of Ammannia multiflora resulted in the isolation and characterization of 4-hydroxy-α-tetralone (1) and 3,3′-(2 R,5 R)-tetrahydrofuran-2,5-diyldiphenol (ammaniol, 2). Compound 1 was chemically modified into six semi-synthetic acyl and aryl derivatives (1A - 1F). The isolated compounds 1 and 2 along with semi-synthetic derivatives 1A - 1F were evaluated for in vitro antihyperglycemic activity employing 2-deoxyglucose uptake by L-6 rat muscle cell lines. The results indicated that both the isolates, as well as derivatives (1A - 1F), have the property to stimulate glucose uptake. Ammaniol (2) increased glucose uptake significantly (64.8%), while one of the aryl derivatives of 1, 4- O-(3,4,5-trimethoxybenzoyl)-α-tetralone (1D), showed potent antihyperglycemic activity and increased glucose uptake by 94.6%, even more than rosiglitazone (88.8%). Further, since 1D possesses better antihyperglycemic activity than rosiglitazone (standard), this might be a new safer antidiabetic drug of herbal origin.
Free Radical Scavenging Activities of Naturally Occurring and Synthetic Analogues of Sea Urchin Naphthazarin Pigments
Authors: Utkina Natalia K. , Pokhilo Natalia D.
Published: March 2019

Antioxidant activities of minor pigments of sea urchins (1–5) and synthetic naphthazarins (7–13) were evaluated and compared with echinochrome A (6) using 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) (ABTS) scavenging assays. Structure-activity relationships showed that the antioxidant activities of the tested compounds depended on the number and positions of hydroxyl groups. Compounds bearing 3 or 2 hydroxyl groups on a naphthazarin core (5,8-dihydroxy-1,4-naphthoquinone) were the most active in both assays. Echinochrome A (6) (IC50 7.0 μM) and its monomethyl ethers 7 (IC50 15.0 μM) and 8 (IC50 15.0 μM) displayed stronger activities than Trolox (IC50 16.0 μM) in the DPPH and ABTS assays (TE = 3.41, 2.35, and 2.35 mM, respectively). Compounds with either one or without hydroxyl groups on a naphthazarin core displayed activities significantly lower than Trolox in both assays. These results suggest that hydroxylated naphthazarin pigments of sea urchins have a potential use as natural antioxidants.
Revisit to (Z)-Civetone Synthesis
Authors: Hagiwara Hisahiro , Adachi Teppei , Nakamura Tomomi , Hoshi Takashi , Suzuki Toshio
Published: March 2019

The synthesis of ( Z)-civetone (1) is described starting from oleic acid (5) via a series of reactions, intermolecular olefin self-metathesis, bromination/dehydrobromination into acetylene, semi-hydrogenation and intramolecular Dieckmann macrocyclization.
Chemical Composition and Antimicrobial Activity of Essential Oil of Heracleum rigens
Authors: Jagannath Nataraj , Ramakrishnaiah Hanumanthaiah , Krishna Venkatarangaiah , Gowda Prameela Javarayi
Published: March 2019

The essential oil was extracted from the seeds of Heracleum rigens by hydrodistillation and a total of twenty compounds accounting for 98.5% of the total oil composition were identified. Physicochemical properties and chemical composition of the oil was determined by a combination GC/FID and GC/MS analysis. The major compounds identified were bornyl acetate (51.2%), α-pinene (22.6%), limonene (9.62%), octyl acetate (3.94%), p-cymene (2.85%) and γ-terpinene (1.93%). The antimicrobial activity of the oil was screened by the disc diffusion method against nine pathogenic bacterial strains. Maximum antimicrobial activity was noted against Klebsiella pneumonia and Bacillus subtillis. This investigation corroborates the traditional claim of H. rigens as an effective antimicrobial agent.
The Cytotoxic Activity of Diterpenoids from Isodon species
Authors: Ohsaki Ayumi , Ozawa Masaaki , Komiyama Kanki , Kishida Akio , Isobe Takahiko
Published: March 2019

Fifteen Isodon diterpenoids (1–15) were evaluated for their cytotoxic activity against HeLa and HL-60 human cancer cell lines, and against murine vincristine (VCR)-resistant P388 cells. Kamebanin (14) showed efficient cytotoxic activity against HeLa and HL-60 cells. In addition, although dihydroenmein (2) and trichorabdal B (7) were inactive against several tested cell types, they were found to have cytotoxic-enhancing activity of VCR against VCR-resistant P388 cells.
Constituents of Twig Bark of Pear Cultivars (Pyrus species)
Authors: Tomosaka Hideyuki , Tamimoto Hideaki , Tsukagoshi Yuki , Suzuki Yasutsugu , Ooka Hisako , Ota Michiya
Published: March 2019

Organic solvent extracts from fresh twig bark of Japanese pear cultivars ( Pyrus serotina) Shinko and Nijisseiki, and European pear cultivar ( P. communis) Le Lectier were obtained by maceration with n-hexane and EtOAc, and analyzed in GC-EIMS experiments. In these two Japanese cultivars, the lupeol, betulin, epifriedelinol, friedelin and arbutin contents of Nijisseiki were higher than those of Shinko. In the case of the lupane-type triterpenes, lupeol and betulin, the lupeol content of Japanese pears Shinko and Nijisseiki was higher than that of European pear Le Lectier. The betulin content of Le Lectier was higher than those of Shinko and Nijisseiki. Friedelane-type triterpenes, epifriedelinol and friedelin, were not detected in twig bark of Le Lectier. Quantitative and qualitative differences in the constituents of these three pear cultivars were observed.
In Vitro Antiviral Activity of Heterophyllaea pustulata Extracts
Authors: Konigheim Brenda S. , Beranek Mauricio , Comini Laura R. , Aguilar Javier J. , Marioni Juliana , Cabrera José L. , Contigiani Marta S. , Montoya Susana C. Núñez
Published: March 2019

The antiviral activity was tested of different polarity extracts, with differing chemical composition, obtained from aerial parts of Heterophyllaea pustulata Hook f. (Rubiaceae) against Herpes Simplex Virus Type I (HSV-1) and Saint Louis Encephalitis Virus (SLEV). The Vero cell line was employed as a host cell for the antiviral assessment of benzene (Ben), ethyl acetate (EtOAc) and ethanol (EtOH) extracts by means of the Neutral Red uptake assay and plaque reduction test. None of the extracts showed antiviral activity against SLEV. Only the extracts (Ben and EtOAc) with a high content of anthraquinones (AQs) inhibited HSV-1 replication, exhibiting Selectivity Index (SI) values of 2.7 and 2.4, respectively. Therefore, these extracts could be good candidates as natural sources for antiviral drug development against HSV-1.
Re-investigation of the Anthraquinone Pool of Rhamnus spp.: Madagascin from the Fruits of Rhamnus cathartica and R. intermedia
Authors: Epifano Francesco , Genovese Salvatore , Kremer Dario , Randic Marco , Carlucci Giuseppe , Locatelli Marcello
Published: March 2019

As a continuation of our ongoing studies aimed at revealing the presence of oxyprenylated anthraquinones in plants belonging to the genus Rhamnus, in this paper we describe the extraction and HPLC separation of madagascin (3-isopentenyloxyemodin) from the fruits of R. cathartica L. and R. intermedia Steud. & Hochst. The title compound is described herein for the first time as a component of fruit extracts of Rhamnus species.
Phytochemical Profiles of Volatile Constituents from Centaurea ragusina Leaves and Flowers and their Antimicrobial Effects
Authors: Politeo Olivera , Skocibusic Mirjana , Carev Ivana , Burcul Franko , Jerkovic Igor , Sarolic Mladenka , Milos Mladen
Published: March 2019

The volatile oils obtained from the leaves and flowers of the Croatian endemic plant Centaurea ragusina L. were evaluated for antimicrobial activity. The chemical compositions, determined by GC and GC-MS, were complex, with sesquiterpenes the most abundant class of compound. Nonterpene hydrocarbons were also identified in high quantities, while acids and ketones were found in high quantities only in the leaf volatile oil. Aldehydes, alcohols, esters and other compounds were identified in lower quantities.

Antimicrobial effects of the volatile samples were investigated by using the disc diffusion and microdilution assays. They were found to inhibit a wide range of bacteria and fungi, causing in vitro growth inhibition at a concentration of 250 μg/mL. The volatile oils displayed great antibacterial potential with MIC values ranging from 16 to 128 μg/mL against the Gram-positive bacteria Bacillus cereus, Clostridium perfringens, Enterococcus faecalis and Staphylococcus aureus, and lesser activity against the Gram-negative bacteria Cronobacter sakazakii, Escherichia coli, Klebsiella pneumoniae and Pseudomonas aeruginosa, as well as fungal strains (MIC= 32–128 μg/mL).
Royleanumin, a New Phytotoxic neo-Clarodane Diterpenoid from Teucrium royleanum
Authors: Ahmad Shabir , Arfan Muhammad , Riaz Naheed , Ullah Riaz , Shah Ziarat , Shah Azhar Ul-Haq Ali
Published: March 2019

Here we report the isolation and structure elucidation of a new phytotoxic neo-clerodane diterpenoid, royleanumin (1), along with known constituents, ursolic acid and β-amyrin. Its structure was deduced by spectral studies including NMR spectroscopy, mass spectrometric techniques and by the comparison with reported data. The compound was assayed for its phytotoxicity against lettuce seedlings. Royleanumin (1) exhibit strong activity and can be proposed as lead chemical for the development of a new environmentally friendly herbicide.
Triterpene Glycosides from the Sea Cucumber Eupentacta fraudatrix. Structure and Biological Activity of Cucumariosides B1 and B2, Two New Minor Non-Sulfated Unprecedented Triosides
Authors: Silchenko Alexandra S. , Kalinovsky Anatoly I. , Avilov Sergey A. , Andryjaschenko Pelageya V. , Dmitrenok Pavel S. , Martyyas Ekaterina A. , Kalinin Vladimir I.
Published: March 2019

Two new minor triterpene glycosides, cucumariosides B1 (1) and B2 (2) have been isolated from the Far Eastern sea cucumber Eupentacta fraudatrix. Structures of the glycosides were elucidated by 2D NMR spectroscopy and MS. Glycosides 1 and 2 belong to the cucumariosides B group and have unprecedented trisaccharide carbohydrate moieties without sulfate groups. Glycosides 1 and 2 differ from each other in side chain structures in the aglycone moieties. These minor substances are probably intermediate metabolites in the biosynthesis of triterpene pentaosides. Cytotoxic activities of glycosides 1 and 2 against mouse spleen lymphocytes and the cells of the ascite form of mouse Ehrlich carcinoma were studied, along with hemolytic activity against mouse erythrocytes and antifungal activity. Cucumarioside B1 (1) was not active in any of the tests, while cucumarioside B2 (2) demonstrated moderate hemolytic activity and low cytotoxic action against Ehrlich carcinoma cells.
Angustinine – A New Benzopyridoquinolizine Alkaloid from Alangium lamarckii
Authors: Chakraborty Mumu , Mukhopadhyay Sibabrata
Published: March 2019

A new benzopyridoquinolizine alkaloid, designated as angustinine (1), was isolated from the root bark of Alangium lamarckii Thwaites, along with the known ipecac alkaloid, emetine. Investigation of the stem bark of the same plant resulted in the isolation of another known ipecac alkaloid, cephaeline. The structure of the new alkaloid (1) was elucidated on the basis of 2D NMR spectral analysis.
Phytochemical and Biological Studies on Some Egyptian Seaweeds
Authors: Elsayed Khaled N. M. , Radwan Mohamed M. , Hassan Sherif H. M. , Abdelhameed Mohamed S. , Ibraheem Ibraheem B. , Ross Samir A.
Published: March 2019

Extracts of four species of seaweeds, Ulva lactuca L. (green), Liagora farinosa Lamouroux (red), Padina pavonia L. and Turbinaria ornata Turn (brown), were screened for their antimicrobial, and antimalarial activities, and binding affinity for human opioid receptors. Phytochemical analysis led to the isolation and identification of 10 constituents: fucosterol, stearic acid, palmitic acid, palmitoleic acid, oleic acid, myristic acid, p-hydroxybenzoic acid, β-sitosterol, glycerol-1-olyl-3-palmotyl-2-galactoside, and glycerol-1,3-diolyl, The last two compounds displayed strong binding affinity to delta opioid receptors.
Electrochemical Characterization of the Marine Antioxidant Gadusol
Authors: Arbeloa Ernesto Maximiliano , Ramírez Cristina Luján , Procaccini Raúl Ariel , Churio María Sandra
Published: March 2019

The electrochemical properties of gadusol, a metabolite extracted from fish roes, were determined for the first time by cyclic- and square-wave voltammetries on a glassy carbon electrode in buffered aqueous solutions. The aims of the work were characterization of the redox behavior and assessment of the mechanism underlying the antioxidant capacity of the compound. Anodic waves with peak potentials of 710 ± 5 mV and 601 ± 9 mV vs. Ag/AgCl were obtained for gadusol and its anion gadusolate, respectively. The voltammograms point to the irreversible nature of the oxidation process and reveal better antioxidant properties for the compound under physiological pH, with a moderate reductive power, but improved stability under atmospheric oxidation in comparison with other natural antioxidants such as ascorbic acid. The presence of direct ionic micelles prepared with sodium dodecyl-sulfate or cetyl-trimethyl-ammonium chloride yielded no significant differences regarding homogeneous medium in the cyclic voltammetry of gadusolate. The results provide evidence of the electron transfer mechanism for the quenching reaction of standard-reactive species by gadusolate and support it as a promising candidate to be tested as an antioxidant additive to food, cosmetic and pharmaceutical formulas. The direct analysis of the metabolite in biological systems and natural extracts by electrochemical methods is also envisaged.
Chemical Composition and Biological Activity of the Essential Oil from Jamaican Cleome serrata
Authors: McNeil Megil J. , Porter Roy B. R. , Williams Lawrence A. D.
Published: March 2019

The chemical composition of the essential oil obtained from the aerial parts of Cleome serrata by hydrodistillation was analyzed by employing GC-FID, GC-MS and RI. Fourteen compounds comprising 90.4% of the total oil composition were characterized. The main components identified were ( Z)-phytol (53.0%) and di(2-ethylhexyl)-phthalate (DEHP) (14.7%). The oil was evaluated for its in vitro antimicrobial activities against nine pathogenic microorganisms using the filter paper disc diffusion method. Moderate antimicrobial activity was observed against five of the pathogens assayed. In addition, the essential oil was tested against the sweet potato weevil, Cylas formicarius elegantulus. Strong knockdown insecticidal activity was observed.
Chemical Compositions and Biological Activities of Amomum subulatum Essential Oils from Nepal
Authors: Satyal Prabodh , Dosoky Noura S. , Kincer Brittany L. , Setzer William N.
Published: March 2019

The essential oils from the seed and rind of Amomum subulatum Roxb. (collected from Nepal) were obtained by hydrodistillation and analyzed by GC-MS. A total of 87 components were identified among the two essential oils accounting for 99.1%, and 99.0% of the oils, respectively. The two essential oils were dominated by the monoterpenoids 1,8-cineole (60.8% and 39.0%), α-pinene (6.4% and 4.8%), β-pinene (8.3% and 17.7%), and α-terpineol (9.8% and 12.3%). Allelopathic testing of the seed essential oil showed an inhibition of seed germination of Lactuca sativa and Lolium perenne, with IC50 values of 1583 and 1674 μg/mL, respectively. The seed essential oil demonstrated a stronger seedling growth inhibition of L. perenne than of L. sativa. A. subulatum seed and rind oils also showed moderate brine shrimp lethality (LC50 = 28.1 ± 3.0 and 15.0 ± 9.0 μg/mL, respectively). The seed and rind oils were only marginally cytotoxic (20% and 30%% kill on MCF-7 cells at 100 μg/mL, respectively), and antibacterial (MIC ≥ 313 μg/mL), but A subulatum rind oil was appreciably active against the fungus Aspergillus niger (MIC = 19.5 μg/mL). The essential oils of A. subulatum were also screened for nematocidal activity against Caenorhabditis elegans and insecticidal activity against the fruit fly (Drosophila melanogaster) and the red imported fire ant (Solenopsis invicta × richteri). The seed oil was only marginally toxic to the fire ant (LC50 = 1500 μg/mL), but moderately toxic to the nematode and the fruit fly (LC50 = 341 and 441 μg/mL, respectively).
Secondary Metabolites of Eichhornia crassipes (Waterhyacinth): A Review (1949 to 2011)
Authors: Lalitha Pottail , Sripathi Shubashini K. , Jayanthi Ponnusamy
Published: March 2019

Eichhornia crassipes (Mart.) Solms (Waterhyacinth), an aquatic perennial herb present throughout the world, has a myriad of metabolites. Phenalenone compounds and sterols have been isolated from this plant. Extracts, as well as pure compounds isolated from this plant, have been demonstrated to possess pharmacological activities. An account of the phytochemistry, pharmacological activities and several applications of waterhyacinth are included in this review.
HPLC Analysis and Cytotoxic Activity of Vernonia Cinerea
Authors: Khay Mom , Toeng Phirom , Mahiou-Leddet Valérie , Mabrouki Fathi , Sothea Kim , Ollivier Evelyne , Elias Riad , Bun Sok-Siya
Published: March 2019

The extracts of five Cambodian medicinal plants ( Aganosma marginata, Dracaena cambodiana, Harrisonia perforata, Hymenodictyon excelsum and Vernonia cinerea) were evaluated in vitro for their cytotoxic activity against HT29 colon adenocarcinoma cells and HepG2 hepatoma cells, using the MTT assay. Among these five plants, Vernonia cinerea displayed potent cytotoxicity. One main sesquiterpene lactone, 8α-tigloyloxy-hirsutinolide-13- O-acetate was isolated from the whole plant of V. cinerea. This compound was active against both cancer cell lines (IC50 = 3.50 μM for HT29 and IC50 = 4.27 μM for HepG2). To quantify this compound in the plant, an analytical high-performance liquid chromatography (HPLC) method was developed and validated.
Effect of Piperine on the Pharmacokinetics and Pharmacodynamics of Glimepiride in Normal and Streptozotocin - Induced Diabetic Rats
Authors: Veeresham Ciddi , Sujatha Samala , Rani Thatipamula Sandya
Published: March 2019

The effect of piperine on the pharmacokinetics and pharmacodynamics of glimepiride in normal as well as diabetic rats was studied. In normal and streptozotocin induced diabetic rats the combination of glimepiride with piperine increased all the pharmacokinetic parameters, such as Cmax, AUC0-n, AUCtotal, t½, and MRT, and decreased the clearance, Vd, markedly as compared with the control group. In pharmacodynamic studies, the combination of glimepiride with piperine provided significant protection against the diabetes induced alterations in the biochemical parameters. In addition, the combination of glimepiride with piperine also improved the total antioxidant status significantly in diabetic rats compared with piperine and glimepiride treated groups. The results revealed that a combination of glimepiride with piperine led to the enhancement of the bioavailability of glimepiride by inhibiting the CYP2C9 enzyme, which suggested that piperine might be beneficial as an adjuvant to glimepiride in a proper dose, in diabetic patients.
Two New Flavonoids from the Seeds of Derris scandens
Authors: Munikishore Rachakunta , Rammohan Aluru , Padmaja Adivireddy , Gunasekar Duvvuru , Deville Alexandre , Bodo Bernard
Published: March 2019

Two new flavonoids, (2 S)-3′,4′,5′-trimethoxyflavanone (1) and 2′-hydroxy-2,4-dimethoxy-4′- O-[( E)-3,7-dimethyl-2,6-octadienyl]chalcone (2), together with a known pterocarpene, flemichapparin B (3), and a known rotenoid, dehydrodeguelin (4), were isolated from the seeds of Derris scandens. Their structures were determined by means of extensive 1D and 2D NMR spectral studies.
Flavonoids Bearing an O-Arabinofuranosyl-(1→3)-Rhamnoside Moiety from Cladocolea Micrantha: Inhibitory Effect on Human Melanoma Cells
Authors: Guimarães Anderson C. , Magalhães Alvicler , Nakamura Marcos J. , Siani Antonio C. , Barja-Fidalgo Christina , Sampaio André L. F.
Published: March 2019

Eleven known triterpenes (α-amyrin, β-amyrin, lupeol, and their respective acetates, 3- O-acetyl derivatives of betulinic, oleanolic, and ursolic acids, cycloartenol, and tirucall-7,24-dienol), two new flavonols presenting an uncommon interglycosidic O-(1→3) linkage (kaempferol 3- O-α-L-arabinofuranosyl-(1→3)-α-L-rhamnoside and quercetin 3- O-α-L-arabinofuranosyl-(1→3)-α-L-rhamnoside), β-sitosterol, stigmasterol, quercetin, and gallic acid were isolated from the Amazonian medicinal mistletoe, Cladocolea micrantha Kuijt (Loranthaceae). Their structures were established by spectral methods and eventual chromatographic comparisons. The quercetin derivative was not cytotoxic to MV3 human melanoma cells, but was able, when administered at 1 μg/mL, to promote a twofold inhibition of the migration of the cells through the transwell system when compared with paclitaxel at 5 μM.
Chemoenzymatic Synthesis of Two New Halogenated Coumarin Glycosides as Potential Antifungal Agents
Authors: Zhou Liangbin , Liu Ling , Tian Tian , Xue Bailin , Yu Rongmin
Published: March 2019

Two new potential antifungal coumarin glycosides, 6-chlorocoumarin 7- O- β-D-glucopyranoside (1) and 7-hydroxy-4-trifluoromethyl-coumarin 5- O- β-D-glucopyranoside (2), were synthesized via enzyme-mediated glycosylation of the respective aglycone, 6-chloro-7-hydroxycoumarin and 5,7-dihydroxy-4-trifluoromethylcoumarin, using transgenic hairy roots of Polygonum multiflorum. Instead of application of the isolated enzyme and exogenous sugar donors, hairy roots of P. multiflorum were successfully adapted as a whole-cell biocatalyst.
Essential Oil and other Constituents from Magnolia Ovata Fruit
Authors: Barros Letícia F. L. , Ehrenfried Carlos Augusto , Riva Dilamara , Barison Andersson , de Mello-Silva Renato , Stefanello Maria Elida A.
Published: March 2019

The volatile and non-volatile constituents of the unripe fruits of Magnolia ovata(A. St.-Hil.) Spreng. (Magnoliaceae) were studied. The essential oils were obtained by hydrodistillation of the fruit of two plant populations (A and B) and analyzed by GC/FID and GC/MS. The oil of sample A was rich in sesquiterpenes, mainly spathulenol (19.3%), while the oil of sample B showed a predominance of aliphatic compounds, mainly hexadecanoic acid (52.0%). Extracts of the dried fruit contained fourteen known compounds including nine lignoids (magnovatin A, magnovatin B, acuminatin, licarin A, oleiferin A, oleiferin C, kadsurenin M, 4- O-demethylkadsurenim M and 7- epi-virolin), two sesquiterpene lactones (parthenolide and michelenolide) and three alkaloids (lysicamine, lanuginosine and O-methylmoschatoline). Michelenolide, 7- epi-virolin and lisycamine are reported for the first time in the species, while the remaining compounds have already been reported in the leaves and/or trunk bark of Magnolia ovata. Acetylation of oleiferin A yielded a new compound, acetyl oleiferin A, whose NMR data and that of michelenolide are furnished.
Conformational Analysis of Antistaphylococcal Sesquiterpene Lactones from Inula helenium Essential Oil
Authors: Blagojević Polina D. , Radulović Niko S.
Published: March 2019

Isomeric eudesmane-type sesquiterpene lactones: alantolactone (1), isoalantolactone (2) and diplophyllin (3), the main constituents of Inula helenium L. root essential oil, are strong antistaphylococcal agents. Energetically favorable conformations of these were calculated (MM+ and MMFF94 molecular mechanics and AM1 and PM3 semi-empirical methods) and mutually compared. The compounds were additionally described in terms of selected 2D and 3D molecular descriptors. Alantolactone and isoalantolactone mainly adopt “U”-shaped conformations (>99%, calculated at 298 K; “closed” geometries), with the carbonyl moiety being rather sterically hindered by the axial methyl group. In contrast, the cyclohexene and lactone rings of diplophyllin are mutually oriented in such a way to give the overall “S”-shape to the molecule (“open” geometry). These conformational differences, inherently influencing the optimal interaction of lactones 1-3 with the binding region of target biomolecules, could be, at least partially, responsible for the higher observed antistaphylococcal activity of diplophyllin in comparison with the other two isomeric lactones.
Preparation of O-Methyl Substituted 2-Oxofuro- and 2-Oxopyrrolidinoindolines by Reductive Lactonization of Oxindol-3-Ylacetic Acids
Authors: Morales-Ríos Martha S. , Rivera-Becerril Ernesto , López-Camacho Perla Y. , Pérez-Rojas Nadia A. , Suárez-Castillo Oscar R.
Published: March 2019

A practical procedure for the preparation of O-methyl substituted 3a,8-dialkyl-2-oxofuroindolines is described. Reductive lactonization of the corresponding oxindol-3-ylacetic acids provides a route for the formation of this class of compounds. Further transformation of 2-oxofuroindolines into 2-oxopyrrolidinoindolines, and then to pyrrolidinoindolines demonstrates their versatility as key intermediates in natural products synthesis. The results of single-crystal X-ray crystallographic analyses are given for five of the studied compounds.
Thymus mastichina: Chemical Constituents and their Anti-Cancer Activity
Authors: Gordo Joana , Máximo Patrícia , Cabrita Eurico , Lourenço Ana , Oliva Abel , Almeida Joana , Filipe Mariana , Cruz Pedro , Barcia Rita , Santos Miguel , Cruz Helder
Published: March 2019

The cytotoxicity-guided study of the dichloromethane and ethanol extracts of Thymus mastichna L. using the HCT colon cancer cell line allowed the identification of nine compounds, sakuranetin (1), sterubin (2), oleanolic acid (3), ursolic acid (4), lutein (5), β-sitosterol (6), rosmarinic acid (7), 6-hydroxyluteolin-7- O-β-glucopyranoside (8), and 6-hydroxyapigenin-7- O-β-glucopyranoside (9). All compounds were tested for their cytotoxicity against the HCT colon cancer cell line. Compound 4 showed cytotoxicity with GI50 value of 6.8 μg/mL. A fraction composed of a mixture (1:1) of triterpenoid acids 3 and 4 displayed improved cytotoxicity with a GI50 of 2.8 μg/mL suggesting a synergistic behavior. This is the first report on the chemical constituents of Thymus mastichna L. based on structural assignments by spectroscopic analysis. The presence of these constituents identified by colon cancer cytotoxicity-guided activity indicates that extracts of T. mastichna L. may have a protective effect against colon cancers.
Effect of 1,5-Anhydro-D-Fructose on the Inhibition of Adipogenesis in 3T3-L1 Adipocytes
Authors: Kojima-Yuasa Akiko , Deguchi Yohei , Konishi Yotaro , Matsui-Yuasa Isao
Published: March 2019

1,5-Anhydro-D-fructose (1,5-AF) is a monosaccharide that shares a structural similarity to glucose. 1,5-AF is found in fungi, algae, Escherichia coli and rat liver and is produced by the degradation of starch and glycogen, which is catalyzed by the enzyme α-1,4-glucan lyase. However, the physiological role of 1,5-AF in mammalian tissues is not well understood. Here, we investigated the anti-obesity potential of 1,5-AF on adipogenesis in 3T3-L1 adipocytes. 1,5-AF caused a significant decrease in GPDH activity in 3T3-L1 preadipocytes and mature adipocytes without eliciting cytotoxicity, and inhibited cellular lipid accumulation through down-regulation of transcription factors such as PPARγ and C/EBPα. 1,5-AF also induced dose-dependent phosphorylation of AMP-activated protein kinase (AMPK), a cellular energy sensor. However, the total AMPK protein content remained unchanged. Furthermore, 1,5-AF increased the levels of reactive oxygen species, an important upstream signal for AMPK activation in 3T3-L1 adipocytes. Our results show that 1,5-AF exerts anti-obesity action in vitro and suggest that 1,5-AF is potentially a novel preventative agent for obesity and other metabolic diseases.
Composition of the Essential Oils from Peucedanum Cervaria and P. Alsaticum Growing Wild in the Urban Area of Vienna (Austria)
Authors: Chizzola Remigius
Published: March 2019

The composition of the essential oil from the different above ground plant parts of Peucedanum cervaria and P. alsaticum (Apiaceae) collected in the urban area of Vienna has been studied. P. cervaria fruits and inflorescences had 1.5 and 1.8% essential oil, respectively. All the oils of P. cervaria were dominated by monoterpenes, with the main components being β-pinene (7-58%), α-pinene (7-22%), sabinene (up to 22%), and β-phellandrene with limonene (6-21%). P. alsaticum fruits afforded 0.3-0.4% essential oil. These oils were made up mainly by α-pinene (11-40%), sabinene (16-34%) and β-phellandrene (12-31%). Stems and leaves produced only very small amounts of essential oil (< 0.05%). Besides monoterpenes, these oils contained also E-nerolidol (5-22%), spathulenol (up to 18%), dodecanal (up to 7.5%) and caryophyllene oxide (up to 7%).
Chemical Constituents from the Aerial Parts of Gynura Bicolor
Authors: Chen Jian , Mangelinckx Sven , Adams An , Li Wei-lin , Wang Zheng-tao , De Kimpe Norbert
Published: March 2019

Gynura bicolor (Willd.) DC., is used in folk recipes for the treatment of diabetes mellitus in Jiangsu, Zhejiang and Sichuan province in the south of China. A previous pharmacological study proved that the plant showed significant hypoglycemic activity on normal and alloxan-diabetic mice. In this study, two terpenes, four megastigmane-type norisoprenoids and two glycosides were isolated from the aqueous ethanolic extract of the aerial parts of Gynura bicolor and characterized mainly by NMR spectroscopy and mass spectrometry. These compounds were isolated for the first time from this plant, and no evidence could be found for the previous reported presence of megastigmane-type norisoprenoids in the genus Gynura.
Conversional Synthesis of Heteratisine
Authors: Wang Ling , Chen Qi-Feng , Wang Feng-Peng
Published: March 2019

The first conversional synthesis of heteratisine has been accomplished in 14 steps and 3.2% overall yield from deltaline, mainly including deoxygenation at C- 10, removal of the dioxymethylene moiety, O-demethylation, as well as Baeyer-Villiger oxidation.
Two New Biisoflavonoids from the Roots of Daphne Oleoides
Authors: Yasmeen Shazia , Anwar Muhammad Aijaz , Ferheen Sadia , Afza Nighat , Malik Abdul , Iqbal Lubna
Published: March 2019

Phytochemical investigation of the ethyl acetate soluble fraction of the methanol soluble extract of the roots of Daphne oleoides resulted in isolation and identification of two new isomeric biisoflavonoids characterized as 8,8′’-bi-6-hydroxyorobol (1) and 8,8′’-bi-6, 2′-dihydroxygenistein (2). The structures of these compounds were established by analysis of their 1D and 2D NMR and HRMS data.
Efficient Preparation of Hangekobokuto (Banxia-Houpo-Tang) Decoction by Adding Perilla Herb before Decoction is Finished
Authors: Sumino Megumi , Saito Yuko , Ikegami Fumio , Hirasaki Yoshiro , Namiki Takao
Published: March 2019

Hangekobokuto (banxia-houpo-tang) is a Kampo (traditional Japanese) medicine used mostly for anxiety disorder and consists of Pinellia Tuber, Poria Sclerotium, Magnolia Bark, Perilla Herb and Ginger. Perilla Herb contains an essential oil rich in perillaldehyde, which has a pleasant flavor, but this is easily lost due to heating. We therefore investigated how the major constituents of hangekobokuto, namely perillaldehyde, rosmarinic acid, magnolol and [6]-gingerol, varied with time during decoction and approached an optimal condition for decoction. Rosmarinic acid at 15 min after boiling, and magnolol and [6]-gingerol at 30 min were mostly extracted, while 0.09 mg of perillaldehyde remained at 15 min, but was not detected at 30 min. From these results, a decoction was prepared by adding Perilla Herb 1, 2, 5 and 10 min prior to the termination time of decoction at 30 min. When Perilla Herb was added 1 min beforehand, perillaldehyde was abundant (1.58 mg) and the amount of rosmarinic acid was already the same as that in the conventional decoction at 30 min, but the amount of total extract was inadequate. When Perilla Herb was added 5 min beforehand, perillaldehyde remained to some extent (0.61 mg) and rosmarinic acid was significantly increased compared with that in the conventional decoction at 30 min. From these results, we can conclude that the decoction should be prepared by boiling for not more than 30 min and, if possible, Perilla Herb should be added 5 min prior to the termination time. Considering the antidepressant-like activity of perillaldehyde and rosmarinic acid, the suggested method will not only achieve better treatment for anxiety, but also provide an effective use of crude drugs in the resource-limited environment.
Chemical Composition, Antimicrobial and Antioxidant Properties of the Volatile Oil and Methanol Extract of Xenophyllum Poposum
Authors: González Ana M. , Tracanna María I , Amani Sara M. , Schuff Carola , Poch Miguel J. , Bach Horacio , Catalán César A. N.
Published: March 2019

The essential oil and methanol extract of northwestern Argentina medicinal plant Xenophyllum poposum, collected in Catamarca province, were investigated. GC and GC-MS analyses of the essential oil identified 56 compounds accounting for 92.9%. The main components of the oil were δ-cadinene (16.5%), 6-hydroxytremetone (14.7%), epi-α-cadinol (12.0%), α-cadinol (8.8%), γ-cadinene (7.5%), 1- epi-cubenol (4.2%) and α-muurolene (3.0%). The essential oil exhibited antibacterial activities against five pathogenic strains as well as antifungal activities against two pathogenic fungi. The methanol extract showed antibacterial activity against two strains of Staphylococcus aureus and two pathogenic fungal strains. The main components isolated from the methanol extract were the antifungal 4-hydroxy-3-(isopenten-2-yl)-acetophenone, 6-hydroxytremetone, and tremetone. 6-Hydroxytremetone showed activity against all the fungal strains and one of the S. aureus strains assayed. Antioxidant and radical-scavenging properties of the methanol extract and essential oil were determined using the 2,2′-diphenyl-1-picrylhydrazyl assay and β-carotene bleaching (BCB) test. The methanol extract and the essential oil showed, respectively, moderate and weak antioxidant activity when compared to butylated hydroxytoluene.
Some Secrets of Argania spinosa Water Economy in a Semiarid Climate
Authors: Barradas Mari Cruz Díaz , Zunzunegui María , Esquivias Mari Paz , Boutaleb Said , Valera-Burgos Javier , Tagma Tarek , Ain-Lhout Fátima
Published: March 2019

Argania spinosa is an example of an avoider tree growing under semi-arid conditions in Morocco. To assess what are the physiological strategies of this species, different variables were measured through an annual cycle in two populations located in the species’ main distribution area. Results show the expected decrease of leaf water potential (Ψ) with an increase of water-use efficiency (A/gs) with the onset of the dry season. In summer, leaf conductance (gs) was sensitive to vapour pressure deficit (VPD), and stomatal closure occurred over 30 mbar of VPD. Surprisingly, carbon isotope discrimination (δ13C) maintained very low values over the year, with almost no relationship with any physiological or morphological variable. Hence Argania spinosa presents a complex set of mechanisms to avoid water deficit, but δ13C cannot be used as an ecological tracer of long term WUE.
Effect of Argan and Olive Oil Consumption on the Hormonal Profile of Androgens Among Healthy Adult Moroccan Men
Authors: Derouiche Abdelfettah , Jafri Ali , Driouch Issam , Khasmi Mohammed El , Adlouni Ahmed , Benajiba Nada , Bamou Youssef , Saile Rachid , Benouhoud Mohammed
Published: March 2019

This study aimed to assess the effect of virgin argan oil (VAO) and extra virgin olive oil (EVO) on the hormonal profile of androgens and anthropometric parameters among healthy adult Moroccan men during a controlled nutritional intervention. The study was carried out on 60 young and healthy male volunteers aged between 23 and 40 years old. During a stabilization period of 2 weeks they consumed butter. The group was then randomized into two categories, the first one consuming VAO and the second EVO for 3 weeks. Testosterone (T), luteinizing hormone (LH) and dehydroepiandrosterone (DHEAS) serum concentrations were measured at the beginning of the study and at the end of each period. The Mann-Whitney test was used to compare the two groups (VAO and EVO) during each step of the study. Differences in androgens and anthropometric parameters between the baseline and after 3 weeks of the diet in the VAO and EVO groups were analyzed using the Wilcoxon test. T and LH serum concentrations significantly increased after the intervention period. T levels increased by 19.9% and 17.4% (p < 0.0001), and LH levels by 18.5% (p < 0.007) and 42.6% ( p < 0.0001), respectively, for VAO and EVO ( p < 0.0001). However, DHEAS serum concentrations, body weight, body mass index, arterial pressure and daily energetic intake did not show any significant variation after the intervention with either argan or olive oils. The results suggest that consumption of AVO and EVO might be the origin of a positive action on the androgen hormonal profile of men.
Chemical Composition and Biological Activities of Soldiers of the Brazilian Termite Species, Nasutitermes macrocephalus (Isoptera: Natutitermitinae)
Authors: de la Cruz Márcia N. S. , Júnior Helvécio M. S. , Oliveira Denilson F. , Costa-Lotufo Letícia V. , Ferreira Antonio G. , Alviano Daniela S. , Rezende Claudia M.
Published: March 2019

The defensive secretion of the frontal gland from termite soldiers is a mixture of monoterpenes, sesquiterpenes and diterpenes, the latter being the most representative. Analyses of the dichloromethane extract from soldiers of the Brazilian termite, Nasutitermes macrocephalus (Silvestri, 1903) (Isoptera, Nasutitermitinae), described for the first time, allowed to identify the presence of two monoterpenes (α-pinene and limonene) and two sesquiterpenes (β-trans- caryophyllene and α-selinene) by GC-EIMS, and the isolation of one rippertane and six trinervitane diterpenes by RP-HPLC. The chemical structures of the purified compounds were elucidated by interpretation of their spectroscopic data (1D and 2D NMR, EIMS, HRESIMS, and specific optical rotation) and the complete unequivocal assignment of the 3α-hydroxy-trinervita-1(15),8(19)-dien-2-one (6) was included in this paper, to complement the lack of information in the literature. Antibacterial, antifungal and cytotoxicity against cancer cell lines activities were evaluated. In particular, the compounds 2α,3β-dihydroxy- trinervita-1(15),8(19)-diene (2) and 3α-hydroxy-15-rippertene (7) exhibited the better activities against the clinically isolated Gram-positive bacterium methicillin-resistant Staphylococcus aureus BMB 9393, both with a MIC value of 31.2 μg mL−1. This is the first description of a rippertane diterpene (7) as an antibacterial agent.