bluuebunny/crossref_metadata_2025 huggingface dataset:
Composition and Antipathogenic Activities of the Twig Essential Oil of Chamaecyparis formosensis from Taiwan
Authors: Ho Chen-Lung , Hua Kuo-Feng , Hsu Kuan-Ping , Wang Eugene I-Chen , Su Yu-Chang
Published: March 2019

In this study, antipathogenic activities of the twig essential oil and its constituents from Chamaecyparis formosensis Matsum were evaluated in vitro against six plant pathogenic fungi. The essential oil from the fresh twigs was isolated using hydrodistillation in a Clevenger-type apparatus, and characterized by GC-FID and GC-MS. Twenty-five compounds were identified, representing 98.9% of the oil. The main components were β-eudesmol (25.1%), τ-muurolol (21.6%), elemol (15.0%), totarol (14.9%), and α-cadinol (12.4%). The twig oil (500 μg/mL) showed growth inhibitory activity against the phytopathogenic fungi, Fusarium oxysporum, Pestalotiopsis funereal, and Ganoderma austral, with antifungal indices of 92.7%, 71.1%, and 87.7%, respectively. In addition, the oil suppressed totally the growth of Rhizoctonia solani, Colletotrichum gloeosporioides, and Fusarium solani. In order to ascertain the source compounds of these antipathogenic activities, the main components were individually evaluated. τ-Muurolol and α-cadinol exhibited excellent activity against F. oxysporum, R. solani, C. gloeosporioides, and F. solani, with IC50< 50 μg/mL. These compounds also efficiently inhibited the mycelial growths of P. funereal and G. austral. Thus, α-cadinol and τ-muurolol could be considered as potential natural fungicides for controlling fungal pathogens and worth.
Chemical Composition and in vitro Evaluation of Antimicrobial and Anti-acetylcholinesterase Properties of the Flower Oil of Ferula lutea
Authors: Znati Mansour , Jabrane Aymen , Hajlaoui Hafedh , Harzallah-Skhiri Fethia , Bouajila Jalloul , Casanova Joseph , Jannet Hichem Ben
Published: March 2019

The present work describes the chemical composition and evaluates the antimicrobial and the anti-acetylcholinesterase properties of the flower oil from the Tunisian Ferula lutea obtained by hydrodistillation and analyzed by combination of GC/FID and GC/MS. The chemical composition of the flower oil of this species is reported for the first time. Seventeen compounds were identified accounting for 94.3% of the total oil. The chemical composition of this essential oil was characterized by a high proportion of monoterpene hydrocarbons (80.4%) among which δ-3-carene (31.2%) and α-pinene (25.8%) were the predominant compounds. The oxygenated monoterpenes represent the second major fraction (12.0%), 2,3,6-trimethylbenzaldehyde (10.9%) being the predominant one. Furthermore, the isolated oil was tested for its antimicrobial activity using the disc-diffusion and the microdilution assays against six Gram-positive and five Gram-negative bacteria as well as towards eight Candida species. It was found that flower oil of F. lutea exhibited interesting antibacterial and anticandidal activity (MIC = 39 μg/mL against Escherichia coli, Staphylococcus aureus and S. epidermidis and MIC = 156 μg/mL against Candida albicans). The anti-acetylcholinesterase effect of this oil was also evaluated in this work. Results showed that this oil exhibits significant activity (IC50 =70.25±5.41 μg/mL).
Flavonoid Constituents of Pistacia integerrima
Authors: Ullah Zia , Mehmood Rashad , Imran Muhammad , Malik Abdul , Afzal Rehana A.
Published: March 2019

Pistacides A and B (1–2), two new flavonoid glycosides, have been isolated from the methanolic extract of the aerial parts of Pistacia integerrima, along with 2′-hydroxyisoorientin (3), echioidinin 2′- O-β-D-(6″- O-acetyl) glucopyranoside (4), chrysoeriol (5), and diandraflavone A (6), reported for the first time from this species. Their structures were elucidated by spectroscopic analysis including 2D NMR, FAB-MS, and acidic hydrolysis.
Two New Phloroglucinol Derivatives and Five Photosensitizing Pheophorbides from Syzygium polyanthum Leaves (Salam)
Authors: Har Lee Wei , Shaari Khozirah , Boon Lee Hong , Kamarulzaman Fadzly A. , Ismail Intan S.
Published: March 2019

Two new phloroglucinol derivatives, identified as anthuminoate (1) and anthuminone (2), were isolated from the ichthyotoxic ethyl acetate fraction of Syzygium polyanthum leaves. In addition, bioassay-guided fractionation followed by dereplication of the photocytotoxic fraction of this plant part has resulted in the identification of five known pheophorbides as the bioactive constituents. The compounds were identified as pheophorbide-a, methyl pheophorbide-a, methyl hydroxypheophorbide-a, pheophorbide-b and hydroxypheophorbide-b. Inhibition of cell viability shown by the compounds ranged from 83.3 to 86.1% at a test concentration of 5 μg/mL. This shows that Syzygium polyanthum leaves are a potential new source in the studies of photocytotoxicity for photodynamic therapy.
Production of Curcuminoids in Different in vitro Organs of Curcuma longa
Authors: Pistelli Laura , Bertoli Alessandra , Gelli Federica , Bedini Laura , Ruffoni Barbara , Pistelli Luisa
Published: March 2019

Curcuma longa L. (turmeric) is one of the most important spice and safe food additives. Its main constituents, curcuminoids, showed anti-inflammatory, antitumor and antioxidant effects. In the present work, an in vitro propagation method was developed to achieve selected plant organs with quantified curcuminoid content. I n vitro plants were obtained from sprouting buds as primary explants. The major curcuminoid constituents, such as curcumin (CUR), demethoxycurcumin (DEM), and bis-demethoxycurcumin (bis-DEM) were examined in different organs by LC-DAD-ESI-MS. A significant production of curcumin (more than 260 μg g−1 fresh weight) was obtained from in vitro microrhizomes, especially grown in a Murashige and Skoog medium (MS) supplemented with kinetin (0.1 mg L−1), α-naphthaleneacetic acid (NAA, 1 mg L−1), sucrose (6%), agar (5%) and activated charcoal (0.1%). The analyzed microrhizomes showed reduced amounts of DEM and bis-DEM in comparison with CUR levels. In addition a shoot culture line was suitable to biosynthesize curcuminoids, in a ratio very similar to that identified in the fresh rhizomes of parent plants. This study represents the first direct quantification of curcuminoids in turmeric in vitro shoots and microrhizomes to be used in dietary supplements.
Determination of Chemical Constituents of Leaf and Stem Essential Oils of Artemisia monosperma from Central Saudi Arabia
Authors: Khan Merajuddin , Mousa Ahmad A. , Syamasundar Kodakandla V. , Alkhathlan Hamad Z.
Published: March 2019

The leaf and stem essential oils of Artemisia monosperma from the desert region of central Saudi Arabia were analysed by gas chromatography-based techniques (GC–FID, GC–MS, Co-GC, LRI determination, database and literature search) using polar as well as non-polar columns, which resulted in the identification of 130 components, of which 81 were common to both oils. In the leaf oil 120 compounds were identified, while 91 were identified in the stem oil accounting for 98.4% and 99.7% of the oil composition, respectively. The major constituents of the leaf oil were β-pinene (50.3%), α-terpinolene (10.0%), limonene (5.4%) and α-pinene (4.6%), while the major constituents of the stem oil were β-pinene (36.7%), α-terpinolene (6.4%), limonene (4.8%), β-maaliene (3.7%), shyobunone (3.2%) and α-pinene (3.1%). The two oils showed an important qualitative similarity. However, some specific constituents (39 in the leaf oil and 10 in the stem oil) allow differentiation of the two essential oils.
Catalytic and Molecular Properties of Rabbit Liver Carboxylesterase Acting on 1,8-Cineole Derivatives
Authors: Loandos María del H. , Muro Ana C. , Villecco Margarita B. , Masman Marcelo F. , Luiten Paul G.M. , Andujar Sebastian A. , Suvire Fernando D. , Enriz Ricardo D.
Published: March 2019

Rabbit liver carboxylesterase (rCE) was evaluated as the catalyst for the enantioselective hydrolysis of (±)-3-endo-acetyloxy-1,8-cineole [(±)-4], which yields (1S,3S,4R)-(+)-3-acetyloxy-1,8-cineole [(+)-4] and (1R,3R,4S)-(-)-3-hydroxy-1,8-cineole [(-)-3]. Enantioselective asymmetrization of meso-3,5-diacetoxy-1,8-cineol (5) gives (1S,3S,4R,5R)-(-)-3-acetyloxy-5-hydroxy-1,8-cineole (6), with high enantioselectivity. rCE has been chosen to perform both experiments and molecular modeling simulations. Docking simulations combined with molecular dynamics calculations were used to study rCE-catalyzed enantioselective hydrolysis of cineol derivatives. Both compounds were found to bind with their acetyl groups stabilized by hydrogen bond interactions between their oxygen atoms and Ser221.
Three New Lactarane Sesquiterpenoids from the Mushroom Russula sanguinea
Authors: Yaoita Yasunori , Hirao Moe , Kikuchi Masao , Machida Koichi
Published: March 2019

Three new lactarane sesquiterpenoids, sangusulactones A – C (1 – 3), were isolated from the fruiting bodies of the mushroom Russula sanguinea (Bull.) Fr. (Russulaceae), together with two known ones, blennin A (4) and 15-hydroxyblennin A (5). The structures of the new compounds were elucidated on the basis of spectral data.
Bioactive-guided Identification of Labdane Diterpenoids from Aerial Parts of Aristeguietia glutinosa as anti-Trypanosoma cruzi agents
Authors: Varela Javier , Lavaggi María L. , Cabrera Mauricio , Rodríguez Alejandra , Miño Patricio , Chiriboga Ximena , Cerecetto Hugo , González Mercedes
Published: March 2019

A bioactive-guided investigation of the hydro-ethanolic extract of aerial parts of Aristeguietia glutinosa Lam. resulted in the isolation of two diterpenoids, (+)-15-hydroxy-labd-7-en-17-al (1) and (+)-13,14,15,16-tetranor-labd-7-en-l7,12-olide (2), as the anti- Trypanosoma cruzi active principles. The structures of 1 and 2 were determined by spectroscopic analysis. The hydro-ethanolic extract showed anti- T. cruzi activity (IC50= 19.6 μg/mL) whereas the isolated compounds 1 and 2 were near to seven- and one and a half-fold (IC50= 3.0 and 15.6 μg/mL), respectively more active than the original extract. Labdene 1, equipotent as the reference compound (Nifurtimox), displayed low hemolytic activity, low toxicity against murine macrophages, and absence of mutagenicity. These results support the vernacular medicinal use of this plant as an anti- T. cruzi agent.
Chemical Composition and Antimicrobial Activity of Salvia x jamensis Essential Oil
Authors: Fraternale Daniele , Flamini Guido , Bisio Angela , Albertini Maria Cristina , Ricci Donata
Published: March 2019

This is the first report about the composition of the essential oil of Salvia x jamensis. The major compounds identified by GC-MS were β-caryophyllene (14.8 %), β-pinene (6.8 %), caryophyllene oxide (6.0 %), δ-cadinene (5.5 %), α-pinene (5.2 %) and spatulenol (5.2 %). The oil showed antimicrobial activity against three Gram (+) bacteria: Bacillus cereus, Staphylococcus aureus, and S. epidermidis, and three Candida strains: C. albicans, C. glabrata and C. tropicalis, while it was inactive against three Gram (-) bacteria: Pseudomonas aeruginosa, Escherichia coli and Enterobacter cloacae.
Composition, Anticancer, and Antimicrobial Activities in vitro of the Heartwood Essential Oil of Cunninghamia lanceolata var. konishii from Taiwan
Authors: Su Yu-Chang , Hsu Kuan-Ping , Wang Eugene I-Chen , Ho Chen-Lung
Published: March 2019

This study investigated the chemical composition, anticancer, and antimicrobial activities in vitro of the essential oil isolated from the heartwood of Cunninghamia lanceolata var. konishii from Taiwan. The essential oil was isolated using hydrodistillation in a Clevenger-type apparatus, and characterized by GC-FID and GC-MS. Thirty-seven compounds were identified, representing 100% of the oil. The main components identified were cedrol (58.3%), α-cedrene (11.8%), α-terpineol (4.2%) and β-cedrene (3.5%). The oil exhibited cytotoxic activity against human lung, liver and oral cancer cells. The active source compound was cedrol. The antimicrobial activity of the oil was tested by the disc diffusion and micro-broth dilution methods against ten microbial species. The oil exhibited strong growth suppression against Gram-positive bacteria and yeast with inhibition zones of 42~50 mm to MIC values of 31.25~62.5 μg/mL, respectively. For the antimicrobial activities of the oil, the active compound was determined to be cedrol.
In Silico Prediction of the Cosmetic Whitening Effects of Naturally Occurring Lead Compounds
Authors: Fong Pedro , Tong Henry H. Y.
Published: March 2019

The identification of tyrosinase inhibitors is important, not only for the treatment of skin hyperpigmentation disorders, such as melasma, but also for the production of cosmetic whitening effects. The aim of this study was the in silico prediction of the naturally occurring lead compounds in three commonly used skin-whitening herbs: Ampelopsis japonica, Lindera aggregata, and Ginkgo biloba. The active ingredients responsible for the whitening effect of these herbs remain largely unknown. The tyrosinase binding affinities and skin permeation, skin irritancy, and corrosive properties of 43 natural constituents of the three herbs were predicted by docking simulations using Surflex-Dock and the QSAR-based Dermal Permeability Coefficient Program (DERMWINTM) and Skin Irritation Corrosion Rules Estimation Tool (SICRET) implemented in Toxtree. Nine constituents of the three herbs were found to have more advanced binding energies than the gold standard whitening agents, arbutin and kojic acid, but 40 were indicative of at least one skin sensitization alert, and many exhibited poor skin permeability. Linderagalactone c and (+)- n-methyllaurotetanine were found to have the strongest prospects for use in topical formulations, as they achieved high predicted tyrosinase binding scores and displayed good skin permeation properties and minimal potential for skin sensitization and irritation.
Thymofolinoates A and B, New Cinnamic Acid Derivatives from Euphorbia thymifolia
Authors: Hussain Riaz , Ali Bakhat , Imran Muhammad , Malik Abdul
Published: March 2019

Two new cinnamic acid derivatives, thymofolinoates A (1) and B (2) have been isolated from the chloroform soluble fraction of Euphorbia thymifolia and their structures assigned from 1H and 13C NMR spectra, DEPT and by 2D COSY, HMQC and HMBC experiments. In addition, p-hydroxy cinnamic acid (3), 5-hydroxy-6,7,8,4′-tetramethoxy flavone (4), and 5-hydroxy-3′,4′,6,7,8-pentamethoxy flavone (5) have also been isolated for the first time from this species.
Norlignans from Asparagus Cochinchinensis
Authors: Li Xing-Nuo , Chu Chu , Cheng Dong-Ping , Tong Sheng-Qiang , Yan Ji-Zhong
Published: March 2019

A new norlignan glycoside, named iso-agatharesinoside (2), and its aglycone, iso-agatharesinol (1), were isolated from the tuberous roots of Asparagus cochinchinensis. Their structures were established on the basis of spectral data, particularly by the use of 1D NMR and several 2D shift-correlated NMR pulse sequences (1H-1H COSY, HSQC, HMBC and ROESY).
Larvicidal Activity against Aedes Aegypti of Essential Oils from Northeast Brazil
Authors: Lavor Patrícia L. , Santiago Gilvandete M. P. , da Silva Gois Roberto W. , de Sousa Leôncio M. , Bezerra Gabrieli da P. , Romero Nirla R. , Arriaga Ângela M. C. , Lemos Telma L. G. , Alves Péricles B. , Gomes Paulo C. S.
Published: March 2019

The larvicidal activities of essential oils from the leaves of Artemisia vulgaris L., Cymbopogon flexuosus(Nees ex Steud.) Wats. and Piper tuberculatum Jacq. were evaluated using third-instar larvae of Aedes aegypti. The essential oils were obtained by hydrodistillation and analyzed by GC and GC-MS. The essential oil of P. tuberculqatum had the lowest LC50 value (106.3 ± 2.2 μg/mL), followed by that of A. vulgaris(114.1 ± 1.7 μg/mL) and C. flexuosus(121.6 ± 0.8 μg/mL). The results show that these essential oils may be potent sources of natural larvicides.
Composition and Antipseudomonal Effect of Essential Oils Isolated from Different Lavender Species
Authors: Végh Anna , Bencsik Tímea , Molnár Péter , Böszörményi Andrea , Lemberkovics Éva , Kovács Krisztina , Kocsis Béla , Horváth Györgyi
Published: March 2019

The aims of our research include the phytochemical characterization of the essential oils extracted from different lavender species ( Lavandula vera L., L. intermedia L., L. pyrenaica DC., and L. stoechas subsp. stoechas) that are important from therapeutic and economic aspects, as well as the optimization of the tube dilution method for microbiological investigation of the effect of essential oils on the selected Pseudomonas strain. The chemical and percentage compositions of the essential oils were analysed by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). The main component of the essential oils in the majority of lavender species was linalool, while L-fencone was identified in the largest amount in L. stoechas subsp. stoechas. Tube dilution is one of the most frequently used methods for microbiological investigation. Its advantages are that it is easy to perform and provides information about minimum bactericidal concentration (MBC). Because of the lipophilic character of essential oils, the tube dilution method should be optimized for the detection of antibacterial activity of these plant extracts, and, therefore, emulsions containing 0.2% polysorbate 80 were prepared from the samples. In each of the eight investigated essential oils an inhibitory effect was detected, and MBC values were in the range 12.5-50 μL/mL in seven cases.
Essential Oil of Croton Argyrophylloides: Toxicological Aspects and Vasorelaxant Activity in Rats
Authors: de França-Neto Aldair , Cardoso-Teixeira Ana Carolina , Medeiros Thiago Coutinho , do Socorro Quinto-Farias Maria , de Souza Sampaio Celia Maria , Coelho-de-Souza Andrelina Noronha , Lahlou Saad , Leal-Cardoso José Henrique
Published: March 2019

Croton argyrophylloides Muell. Arg. is widely used in Brazilian folk medicine to treat diabetes and venereal diseases. This study examined the acute toxicity and cytotoxicity of the essential oil of C. argyrophylloides(EOCA). In addition, vascular effects of the EOCA have been examined. In mice, an oral acute toxicity test revealed that EOCA could be considered as a non toxic essential oil since it showed a very high LD50 (9.84 ± 0.01 g/kg). In the brine shrimp ( Artemia salina) cytotoxic assay, the LC50 value of EOCA was 275 [165-534] μg/mL. EOCA (1-1000 μg/mL) relaxed isolated endothelium-intact aortic rings precontracted with phenylephrine with an IC50 value of 126.7 [89.8-163.7] μg/mL. In rat mesenteric bed preparations precontracted with phenylephrine, EOCA (1-300 μg/mL) also induced a reversible, vasodilator effect with an IC50 value of 46.0 [33.3-58.7] μg/mL. It is concluded that EOCA is a very interesting agent from the point of view of the possibility of therapeutic application. This is because, whilst showing a very small acute toxicity, EOCA also showed maximal efficacy as a vascular antispasmodic agent with a pharmacological potency similar to that of other Croton species essential oils.
Ophiobolin O and 6-Epi-Ophiobolin O, Two New Cytotoxic Sesterterpenes from the Marine Derived Fungus Aspergillus Sp
Authors: Zhang Dahai , Fukuzawa Seketsu , Satake Masayuki , Li Xianguo , Kuranaga Takafumi , Niitsu Ai , Yoshizawa Kentaro , Tachibana Kazuo
Published: March 2019

Two new sesterterpenes, ophiobolin O (1) and 6-epi-ophiobolin O (2), together with the known ophiobolins G (3), H (4), and K (5), and 6-epi-ophiobolin K (6) were isolated from the marine derived fungus Aspergillus sp. The structures of these compounds were elucidated based on chemical and physicochemical evidence, including MS, UV, IR and NMR spectra. The stereochemistry of 1 was further confirmed by catalytic reaction of 5 with p-TsOH as a catalyst. Compounds 1 to 6 showed cytotoxicity against mouse leukemia cell line P388, with IC50 values of 4.7, 9.3, 24.6, 105.7, 13.3 and 24.9 μM, respectively.
A New Monodesmosidic Triterpenoid Saponin from the Leaves of Pometia Pinnata
Authors: Mohammad Faryal Vali , Noorwala Mushtaq , Ahmad Viqar Uddin , Zahoor Aqib , Nordin HJ.
Published: March 2019

Phytochemical investigation of the leaves of Pometia pinnata resulted in the isolation of a new triterpenoid saponin (1), together with a known compound, kaemferol 3- O-α-L-rhamnopyranoside (2). The structure of 1 was established as 3- O-[α-L-arabinofuranosyl-(1→4)–α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl]-hederagenin. The structure elucidation of the isolated compounds was based primarily on 1D- and 2D-NMR techniques, including 1H and 13C NMR spectra, DEPT, and by 2D COSY, HMQC, HMBC and TOCSY experiments.
New Holostan-type Triterpene Glycosides from the Sea Cucumber Apostichopus Japonicus
Authors: Wang Zenglei , Gong Wei , Sun Guoquan , Tang Hua , Liu Baoshu , Li Ling , Yi Yanghua , Zhang Wen
Published: March 2019

Two new holostan-type glycosides, holotoxin D1 (1) and 25,26-dihydroxy-holotoxin A1 (2), together with two known analogues, stichlorosides C1 (3) and bivittoside D (4), were isolated from the sea cucumber Apostichopus japonicus Selenka. The structures of the new compounds were elucidated on the basis of detailed spectroscopic analysis. Glycosides 1 and 3 exhibited potent antifungal activity.
Freshwater Clam Extract Inhibits Inflammatory Responses in LPS-Activated Macrophages by Reducing the Activation of Mitogen-Activated Protein Kinases and NF-κB
Authors: Hua Kuo-Feng , Chen Guan-Ming , Ho Chen-Lung , Chen Ming-Chung , Chen Yi-Lin Sophia , Chen Wei-Jung , Huang Jeng-Fang , Perng Yuan-Shing , Lin Chai-Ching
Published: March 2019

Recent studies demonstrated that freshwater clam (Corbicula fluminea) has lipid-lowering and hepatoprotective activities, but its effect on immune responses has not yet been addressed. Here we showed that ethanol extracts of C. fluminea (ECF) reduced nitrite oxide, interleukin-1β, interleukin-6, and tumor necrosis factor-α in lipopolysaccharide-activated macrophages. Further, ECF was fractionated into n-hexane, ethyl acetate, ethanol, and water soluble fractions. Of these, the ethyl acetate soluble fraction (EACF) had the highest capacity to inhibit pro-inflammatory mediators expression. The underlying mechanisms for the anti-inflammatory activity of EACF were demonstrated as down-regulation of ERK1/2, JNK1/2, and p38 phosphorylation and NF-κB activity. Using gas chromatography-mass spectrometric analysis EACF was found to be composed mainly of fatty acids and steroids. Our results provide evidence that freshwater clam has anti-inflammatory activity, and support the possibility for the development of freshwater clam as a health supplement or adjuvant therapeutic agent for either preventing or treating inflammation related diseases.
A New Monoterpenoid Oxindole Alkaloid from Hamelia Patens Micropropagated Plantlets
Authors: Paniagua-Vega David , Cerda-García-Rojas Carlos M. , Ponce-Noyola Teresa , Ramos-Valdivia Ana C.
Published: March 2019

Chemical studies on Hamelia patens (Rubiaceae) micropropagated plantlets allowed production of a new monoterpenoid oxindole alkaloid, named (–)-hameline (7), together with eight known alkaloids, tetrahydroalstonine (1), aricine (2), pteropodine (3), isopteropodine (4), uncarine F (5), speciophylline (6), palmirine (8), and rumberine (9). The structure of the new alkaloid was assigned on the basis of 1D and 2D NMR spectroscopy, mass spectrometry, and molecular modeling.
Neohesperidin Induces Cellular Apoptosis in Human Breast Adenocarcinoma MDA-MB-231 Cells via Activating the Bcl-2/Bax-mediated Signaling Pathway
Authors: Xu Fei , Zang Jia , Chen Daozhen , Zhang Ting , Zhan Huiying , Lu Mudan , Zhuge Hongxiang
Published: March 2019

Neohesperidin, a flavonoid compound found in high amounts in Poncirus trifoliata, has free radical scavenging activity. For the first time, our study indicated that neohesperidin also induces cell apoptosis in human breast adenocarcinoma MDA-MB-231 cells, which was possibly mediated by regulating the P53/Bcl-2/Bax pathway. MDA-MB-231 cells were subjected to treatment with neohesperidin. MTT and Trypan blue exclusion assays were applied to assess the cell viability. The morphological changes of cells were observed using an inverted microscope, and cell apoptosis was detected by flow cytometric analysis. Immunoblot analysis was conducted to evaluate the protein expressions of apoptosis-related genes, including P53, Bcl-2 and Bax. Our results indicated that the proliferation of MDA-MB-231 cells was inhibited by the treatment with neohesperidin in a time- and dose-dependent manner. The IC50 values of neohesperidin at 24 and 48 h were 47.4±2.6 μM and 32.5±1.8 μM, respectively. The expressions of P53 and Bax in the neohesperidin-treated cells were significantly up-regulated, while that of Bcl-2 was down-regulated. Our study suggested that neohesperidin could induce apoptosis of MDA-MB-231 cells, a process which was associated with the activation of the Bcl-2/Bax-mediated signaling pathway.
New Secoiridoid Glycosides from the Buds of Lonicera macranthoides
Authors: Liu Jiang , Zhang Jing , Wang Feng , Chen Xingfu
Published: March 2019

Two new secoiridoid glycosides, named ethyl secologanoside (1) and 6′- O-α-L-arabinopyranosyl demethylsecologanol (2), together with three known ones, secologanoside (3), secoxyloganin (4), and loniceroside (5), were isolated from the dried buds of Lonicera macranthoides. The structures of the new compounds were determined on the basis of detailed spectroscopic analyses and acidic hydrolysis.
A Practical, Enantiospecific Synthesis of (S)-Trans-γ-Monocyclofarnesol
Authors: Serra Stefano
Published: March 2019

An expedient and concise synthesis of (S)-trans-γ-monocyclofarnesol is here described. The aforementioned sesquiterpene was prepared starting from enantioenriched (S)-γ-dihydroionone, which was in turn obtained from racemic α-ionone through the combined use of two previously developed processes. Key steps of the presented synthesis are the stereoselective Horner-Wadsworth-Emmons reaction between triethyl phosphonoacetate and γ-dihydroionone and the effective fractional crystallization of the γ-monocyclofarnesol-3,5-dinitrobenzoate esters. By these means the target compound was obtained in good yield and with very high stereoisomeric purity.
Cucurbitane-Type Triterpenoids from the Fruit Pulp of Momordica Charantia
Authors: Liao Yun-Wen , Chen Chiy-Rong , Kuo Yueh-Hsiung , Hsu Jue-Liang , Shih Wen-Ling , Cheng Hsueh-Ling , Huang Tzou-Chi , Chang Chi-I
Published: March 2019

Three new cucurbitane-type triterpenoids, 5β,19-epoxy-23(R)-methoxycucurbita-6,24-dien-3β-ol (1), 5β,19-epoxy-23(S)-methoxycucurbita-6,24-dien-3β-ol (2), and 3β-hydroxy-23(R)-methoxycucurbita-6,24-dien-5β,19-olide (3), were isolated from the fruit pulp of Momordica charantia. Their structures were established on the basis of extensive NMR (1H, 13C, COSY, HMQC, HMBC, and NOESY) and EI-MS studies. Compound 1 exhibited cytotoxic activity against the SK-Hep 1 cell line.
Ochnaflavone and Ochnaflavone 7-O-Methyl Ether two Antibacterial Biflavonoids from Ochna pretoriensis (Ochnaceae)
Authors: Makhafola Tshepiso J. , Samuel Babatunde B. , Elgorashi Esameldin E. , Eloff Jacobus N.
Published: March 2019

The acetone extract of Ochna pretoriensis was evaluated for antibacterial activity using bioautography and serial microplate dilution methods against four nosocomial bacterial pathogens namely: Escherichia coli, Staphylococcus aureus, Enterococcus faecalis and Pseudomonas aeruginosa. A bioassay-guided fractionation of the crude extract led to the isolation of two antibacter ial biflavonoids, ochnaflavone and ochnaflavone 7- O-methyl ether. Gram-negative bacteria were more sensitive to the isolated compounds than the Gram-positive bacteria (MIC values: 31.3 μg/mL for P. aeruginosa and 62.5 μg/mL for S. aureus). In addition, the isolated com pounds were assessed for their pot ential toxic effects in the MTT toxicity assay using monkey kidney vero cells and Ames genotoxicity test using Salmonella typhimurium strain TA98. LC50 values were 125.9 μg/mL for ochnaflavone and 162.0 μg/mL for ochnaflavone 7-O- methyl ether. The isolated compounds have selectivity index values r anging from 1.29 to 4.03. Selectivity index values higher than one indicate that test samples are less toxic to the host cells than to the pathogens. The biflavonoids did not have any mutagenic effects in the Salmonella/microsome assay without metabolic activation.
Cinnamic Acid Derivatives Acting against Aspergillus Fungi.Taq Polymerase I a Potential Molecular Target
Authors: Gutierrez Lucas J. , Mascotti Maria L. , Kurina-Sanz Marcela , Pungitore Carlos R. , Enriz Ricardo D. , Giannini Fernando A.
Published: March 2019

Some members of a series of cinnamic acid derivatives possess promising inhibitory activities in cellular assays against fungi of the Aspergillus genus. In order to search for a possible molecular target of such compounds, their role as Taq polymerase I inhibitors was studied. Four of the compounds studied displayed IC50 values within the range of those considered active as DNA polymerase inhibitors when searching for new cytotoxic molecules. The results obtained in our molecular modeling study appear to show that the inhibitory activity depends on the presence of a stabilizing interaction between the phenylpropanoid derivatives and the residues Asp610, Thr664, Phe667, Tyr671, and Asp785 located in the active site of Taq polymerase I. Also, it is possible to assert that the polymerization of DNA would be the molecular target of cinnamic acid derivatives with antifungal activity, which correlates with the inhibition of Taq polymerase I and the quantitative descriptor for the lipophilia (ClogP).
Insecticidal Effects of Acetogenins from Rollinia Occidentalis Seed Extract
Authors: Tolosa Diego , Colom Olga Álvarez , Bardón Alicia , Neske Adriana
Published: March 2019

From the methanol seed extract of Rollinia occidentalis five acetogenins were isolated, sylvaticin (1), rolliniastatin-1 (2), rolliniastatin-2 (3), motrilin (4) and desacetyluvaricin (5), and evaluated for their toxicity and nutritional alterations on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae). All but one of the compounds produced more than 90% mortality on early larval instars at 50 and 100 μg per g of diet. Sylvaticin caused 15 and 60% mortality at 50 and 100 μg/g, respectively, while the methanol seed extract reached 35 and 50% at 100 and 250 μg/g, respectively. The addition of R. occidentalis methanolic seed extract (100 and 250 μg/g) and sylvaticin (100 μg/g) to the larval diet brought about significant changes to the nutritional indices in connection with larvae fed the control diet. This is the first report on the isolation of acetogenins from R. occidentalis and their insecticidal effects on S. frugiperda.
Chemical Compositions, Antioxidant and Antimicrobial Activity of the Essential Oils of Piper officinarum (Piperaceae)
Authors: Salleh Wan Mohd Nuzul Hakimi Wan , Ahmad Farediah , Yen Khong Heng , Sirat Hasnah Mohd
Published: March 2019

This study was designed to investigate the antioxidant and antimicrobial activities of the essential oils from Piper officinarum C. DC. GC and GC/MS analysis of the leaf and stem oils showed forty one components, representing 85.6% and 93.0% of the oil, respectively. The most abundant components in the leaf oil were β-caryophyllene (11.2%), α-pinene (9.3%), sabinene (7.6%), β-selinene (5.3%) and limonene (4.6%), while β-caryophyllene (10.9%), α-phellandrene (9.3%), linalool (6.9%), limonene (6.7%) and α-pinene (5.0%) were the main components of the stem oil. The antioxidant activities were determined by using complementary tests: namely β-carotene-linoleic acid, DPPH radical scavenging and total phenolic assays. The stems oil showed weak activity (IC50 = 777.4 μg/mL) in the DPPH system, but showed moderate lipid peroxidation inhibition in the β-carotene-linoleic acid system (88.9 ± 0.35%) compared with BHT (95.5 ± 0.30%). Both oils showed weak activity against P. aeruginosa and E. coli with M IC values of 250 μg/mL.
Phytochemical and Micromorphological Traits of Endemic Micromeria pseudocroatica (Lamiaceae)
Authors: Kremer Dario , Müller Ivna Dragojević , Stabentheiner Edith , Vitali Dubravka , Kopričanec Martina , Ruščić Mirko , Kosalec Ivan , Bezić Nada , Dunkić Valerija
Published: March 2019

Micromeria pseudocroatica Şilic is an endemic species distributed in southern Croatia. Chemical composition of the essential oil (analysed by GC and GC-MS), and the content of macroelements and trace elements analysed by ICP-AES was conducted. Additionally, a study on the types and distribution of trichomes was done by scanning electron microscopy. The essential oil was characterized by a high concentration of oxygenated monoterpenes, whose major compounds are borneol (22.7% and 24.8%) and camphor (16.1% and 13.9%). The content of Ca was highest (13202.69 mg/kg and 13223.83 mg/kg) among the investigated macroelements, while Fe was the most represented element (100.68 and 326.48 mg/kg) among the micronutrients. The content of potentially toxic elements that is Se, Cu, and Hg was below the limit of quantification. Non-glandular trichomes, peltate trichomes, and two types of capitate trichomes (type 1: one basal epidermal cell, one head cell with subcuticular space; type 2: one basal epidermal cell, two stalk cells, and one head cell with subcuticular space) were observed on leaves, bracteoles, calyx, corolla and stem.
Essential oil Composition of Ficus Benjamina (Moraceae)and Irvingia Barteri (Irvingiaceae)
Authors: Ogunwande Isiaka A. , Jimoh Razaq , Ajetunmobi Adedoyin A. , Avoseh Nudewhenu O. , Flamini Guido
Published: March 2019

Essential oils obtained by hydrodistillation of leaves of two Nigerian species were analyzed for their constituents by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). The leaf oil of Ficus benjamina L. (Moraceae), collected during the day, contained high contents of α-pinene (13.9%), abietadiene (9.7%), cis-α-bisabolene (8.2%) and germacrene-D-4-ol (8.4%), while the night sample was dominated by germacrene-D-4-ol (31.5%), 1,10-di- epi-cubenol (8.8%) and hexahydrofarnesylacetone (8.3%). This could be a possible indication of differences in emissions of volatiles by F. benjamina during the day and night. The main compounds of Irvingia barteri Hook. f. (Irvingiaceae) were β-caryophyllene (17.0%), (E)-α-ionone (10.0%), geranial (7.6%), (E)-β-ionone (6.6%) and β-gurjunene (5.1%).
Argan Oil-contained Antioxidants for Human Mitochondria
Authors: López Luis C. , Cabrera-Vique Carmen , Venegas Carmen , García-Corzo Laura , Luna-Sánchez Marta , Acuña-Castroviejo Darío , Escames Germaine
Published: March 2019

The powerful antioxidant capacity of virgin argan oil is attributed to its content of antioxidant molecules. Recent investigations have identified CoQ10 and melatonin as some of these antioxidant molecules. In this review, we summarize the most recent data about the content of CoQ10 and melatonin in virgin argan oil and the differences found in samples extracted by the traditional and half-industrialized methods. We also emphasize the importance of these two molecules for human health, focusing on their actions in mitochondria. Finally, we refer to other abundant antioxidants in virgin argan oil: tocopherols and polyphenols.
Fusaodavinvin, a Novel Metabolite Containing Sulfur from the Endophytic Fungus Fusarium sp. (CTGU-ZL-34)
Authors: Zhang Liang , Liu Yanhui , Deng Zhangshuang , Guo Zhiyong , Chen Jianfeng , Tu Xuan , Zou Kun
Published: March 2019

A novel metabolite containing sulfur, fusaodavinvin (1), was isolated from an endophytic fungus Fusarium sp.(CTGU-ZL-34), together with seven known compounds 2-8, and their structures were elucidated by NMR spectroscopy and MS. This is the first record of 3-(2R-hydroxyl-1-one-propane)-indole (compound 2) from nature. The isolated compounds were evaluated using the A549, Hep G2, Caski and MCF-7 cell lines by the MTT method, and compound 1 displayed significant inhibiting activity of four cancer cell lines with IC50 values of 11.5, 15.3, 15.2 and 60.5 μg/mL, respectively. However, compound 2 displayed no significant anticancer activity to the above four cancer cell lines.
Effect of Hypogymnia physodes Extracts and their Depsidones on Micronucleus Distribution in Human Lymphocytes
Authors: Stojanović Igor Ž. , Stanković Miroslava , Jovanović Olga , Petrović Goran , Šmelcerovic Andrija , Stojanović Gordana S.
Published: March 2019

Three lichen depsidones, physodalic acid (1), physodic acid (2), and 3-hydroxy physodic acid (3), were isolated from Hypogymnia physodes diethyl ether extract using column chromatography, and their structures determined by comparing their UV,1H and 13C NMR spectroscopic and MS data with those given in the literature, as well as with data computed by CHEM draw ultra 11 software. The contents of 1, 2 and 3 were determined in the methanol (ME), acetone (AE), and diethyl ether (EE) extracts using reversed-phase high performance liquid chromatography with photodiode array detection. The extracts, isolated depsidones 1-3 and EE fraction F23 (consisting of 90% 2 and 3, in the ratio 5.5: 1) were evaluated for their in vitro effects on chromosome aberrations in peripheral human lymphocytes using the cytochalasin-B blocked micronucleus (CBMN) assay in doses of 1 μg/mL and 2 μg/mL of final culture solution. The frequency of MN was scored in binucleated cells, and nuclear proliferation index was calculated. It was found that 1, 2, 3, F23, and EE at 1.0 μg/mL exerted a beneficial effect on lymphocyte cells giving a significant decrease of the frequency of MN in comparison with the positive control Amifostin WR-2721. Among the tested depsidones at a concentration of 1 μg/mL, 3 exhibited the most prominent effect decreasing the frequency of MN by 30.3%, followed by 2 (28.2%) and 1 (22.0%). The extracts were less effective than the isolated depsidones.
A New Lyoniresinol Derivative from Smilax microphylla
Authors: Liu Li-Sha , Huang Hui-Lian , Liu Rong-Hua , Ren Gang , Shao Feng , Ye Yao-Hui , Lin Tao
Published: March 2019

A new lignan, lyoniresinol-9- O-8″-syringylglycerol ether (1), together with five known compounds, piceatannol (2), resveratrol (3), oxyresveratrol (4), quercetin-3′-glucoside (5) and diosgenin (6) were isolated from the rhizomes of Smilax microphylla. The structure of the new compound was determined by means of chemical evidence and 1D-and 2D-NMR (1H, 13C, HSQC, HMBC, 1H-1H COSY and NOESY) spectroscopic analysis and HR-ESI-MS.
Synthesis of 3,5,3′, 4′-Tetrahydroxy-trans-stilbene4′-O-β-D-glucopyranoside by Glucosyltransferases from Phytolacca americana
Authors: Iwakiri Tomoya , Imai Hiroya , Hamada Hiroki , Nakayama Toru , Ozaki Shin-ichi
Published: March 2019

Two glucosyltransferase isozymes from Phytolacca americana, PaGT3 and PaGT2, catalyzed stereo- and regio-selective monoglucosylation of 3,5,3′,4′- tetrahydroxy-trans-stilbene to yield 3,5,3′,4′-tetrahydroxy-trans-stilbene-4′-O-β-D-glucopyranoside.
Chemopreventive Effect of Sarcophine-diol on NOR-1-Induced TPA-Promoted Skin Carcinogenesis in Female HOS:HR-1 Mice
Authors: Szymanski Pawel T. , Ahmed Safwat A. , Khalifa Sherief , Tokuda Harukuni , Ichiishi Eiichiro , Iida Akira , Suzuki Nobutaka , Fahmy Hesham
Published: March 2019

The cancer chemopreventive potential of sarcophine-diol in a chemical carcinogen initiation–promotion experimental tumor model in mice was evaluated. Sarcophine-diol, when given orally, afforded significant protection in the mouse skin cancer model initiated by the topical administration of (±)-( E)-4-methyl-2-[( E)-hydroxyamino]-5-nitro-6-methoxy-3-hexanamide (NOR-1) and promoted by 12- O-tetradecanoylphorbol-13-acetate (TPA). These findings, along with our initial reports, suggest that sarcophine-diol is an effective cancer chemopreventive agent, even when administered orally and at a very low dose and thus indicating possible potential human applications in the control of malignancy.
Two New Amides from Streptomyces michiganensis
Authors: Xue Jinghua , Xu Liangxiong , Jiang Zi-Hua , Wei Xiaoyi
Published: March 2019

A new amide glycoside, 3-α-glucopyranosyloxy- N-methyl-3-phenylpropanamide (1), and a new cyclodipeptide, (3 S,6 S)-3,6-bis(4-acetamidobutyl)piperazine-2,5-dione (2), were isolated from the solid culture of Streptomycetes michiganensis strain SC0642. Their structures were elucidated by spectroscopic methods.
Antiproliferative Effects of an Analog of Curcumin in Hep-2 cells: A Comparative Study with Curcumin
Authors: Kumaravel Mohankumar , Sankar Pajaniradje , Latha Periyasamy , Benson Chellakan S , Rukkumani Rajagopalan
Published: March 2019

Curcumin, the major active principle of Curcuma longa, is one of the promising, plant-derived, chemopreventive agents being studied for its anticarcinogenic and antioxidant properties. Hence, in our study, we aimed at testing the antiproliferative efficacy of an o-hydroxyl substituted analog of curcumin, bis demethoxy curcumin analog (BDMC-A), and comparing its efficacy with that of curcumin. BDMC-A was synthesised with a yield of 78% and 98% purity. Hep-2 cells and the MTT cell viability assay were used to examine cell proliferation. LDH assay and cell counts were performed to assess the cytotoxicity and anti-proliferative effects of the compound, respectively. Flow cytometry followed by Western blot were performed to investigate the cell cycle distribution. BDMC-A inhibited cell proliferation at a much lower concentration (IC50 20 μM) than curcumin (IC50 50 μM). Similar effects were observed in the LDH release and cell count assays. Flow cytometric studies using propidium iodide showed accumulation of cells in the G0/G1 phase and the arrest was further confirmed by immunoblotting of protein cyclin D1. BDMC-A was more potent in inhibiting the cells at a lower dose when compared with curcumin. Our results showed that the analog of curcumin is likely to possess more efficacy compared with curcumin in inhibiting cancer.
Antifeedant Activity of Spin-Labeled Derivatives of Deoxypodophyllotoxin against Brontispa longissima Larvae
Authors: Feng Gang , Zhang Jing , Yang Liu , Liu Ying-Qian , Zhang Zhi-Wei , Tian Xuan , Jin Qi-An , Peng Zheng-Qiang
Published: March 2019

To continue our search for natural product-based compounds for the control of Brontispa longissima larvae, eight spin-labeled podophyllotoxin derivatives (4a-h) and the intermediates 2 and 3 were tested for their insect antifeedant activity against third-instar larvae of B. longissima. Among all the tested compounds, 4a, 4c, 2 and 3 showed pronounced antifeedant activities with AFC50 values of 0.16, 0.31, 0.15 and 0.28 mg/mL, respectively. The different antifeedant activity ranges of these compounds indicated that variation of the structures of L-amino acids in these compounds markedly affected the activity profiles of this compound class, and some important SAR information has been revealed from it.
Chemical Composition and Biological Activity of the Essential Oil of Amomum biflorum
Authors: Singtothong Chakkrapat , Gagnon Michel J. , Legault Jean
Published: March 2019

The aim of this study was to investigate the chemical composition and bioactivity of Amomum biflorum Jack harvested in the region of Petchaboon, Thailand. The essential oil of the fresh whole plant obtained by hydrodistillation was analyzed by gas chromatography (GC) (Kovats index) and gas chromatography coupled with mass spectrometry (GC/MS). The average yield of essential oil of A. biflorum was 0.21 ± 0.05 % (w/w). The major chemical constituents were camphor (17.6 %), α-bisabolol (16.0 %), camphene (8.2 %) and α-humulene (5.1 %). The essential oil was active against Staphylococcus aureus (MIC: 30 μ/mL) and had an antioxidant activity with an ORAC index of 23 ± 5 μmol Trolox/mg.
Composition, in-vitro Anticancer, and Antimicrobial Activities of the Leaf Essential Oil of Machilus mushaensis from Taiwan
Authors: Su Yu-Chang , Ho Chen-Lung
Published: March 2019

This study investigated the chemical composition, in-vitro anticancer, and antimicrobial activities of the essential oil isolated from the leaf of Machilus mushaensis from Taiwan. The essential oil was isolated using hydrodistillation in a Clevenger-type apparatus, and characterized by GC-FID and GC-MS. Forty compounds were identified, representing 100% of the oil. The main components identified were n-decanal (61.0%), and α-cadinol (20.8%). The oil exhibited cytotoxic activity against human oral, liver, lung, colon, melanoma, and leukemic cancer cells. The antimicrobial activity of the oil was tested by the disc diffusion and micro-broth dilution methods against ten microbial species. The oil exhibited moderate growth suppression against Gram-positive bacteria and yeast with inhibition zones of 25-29 mm to MIC values of 375-500 μg/mL, respectively. α-Cadinol was found to show promising anticancer and antimicrobial activities.
Preparation and Application of Reversed Phase ChromatorotorTM for the Isolation of Natural Products by Centrifugal Preparative Chromatography
Authors: Muhammad Ilias , Samoylenko Volodymyr , Machumi Francis , Zaki Mohamed Ahmed , Mohammed Rabab , Hetta Mona H. , Gillum Van
Published: March 2019

A method of preparation of rotors with a reversed phase (RP) solid silica gel sorbent layer has been developed for centrifugal preparative chromatography (CPC), also known as rotational planar chromatography (RPC). The rotors consist of binder free RP solid SiO2 layers of different thicknesses packed between two supported circular glass discs and can be used in any appropriate device for centrifugal chromatography, like Chromatotron® and CycloGraph®. Polar and /or semi-polar compounds with close R f values, as well as extracts and column fractions were separated and /or purified in a preparative and / or semi-preparative scale using the RP rotors, eluted with mixtures of aqueous-based solvents. We herein report three examples of its application, using RP ChromatorotorsTM, for the isolation of the diastereoisomeric alkaloids banistenosides I and II from Banisteriopsis caapi, saponins III and IV from Fagonia cretica, and the sesquiterpenes artemisinin (V) and artemisinic acid (VI) from Artemisia annua.
Two Spirostan Steroid Glycoside Fatty Esters from Dioscorea cayenensis
Authors: Ali Zulfiqar , Smillie Troy J. , Khan Ikhlas A.
Published: March 2019

Two new fatty acid-spirostan steroid glycoside esters, progenin III palmitate (1) and progenin III linoleate (2), were isolated from the MeOH extract of Dioscorea cayenensis rhizomes. The extract also yielded seven previously known spirostan and furostan steroid glycosides (3-9). The structures of the new compounds were established as (25 R)-spirost-5-en-3β-yl O-α-L-rhamnopyranosyl-(1→2)-[6- O-palmitoyl]- O-β-D-glucopyranoside (1) and (25 R)-spirost-5-en-3β-yl O-α-L-rhamnopyranosyl-(1→2)-[6- O-linoleoyl]- O-β-D-glucopyranoside (2) by chemical and spectroscopic methods, including 1D and 2D NMR. The known compounds were identified as progenin III (3), dioscin (4), deltonin (5), asperin (6), gracillin (7), protodioscin (8)], and methyl protodioscin (9).
Andrographidine G, a New Flavone Glucoside from Andrographis paniculata
Authors: Hapuarachchi Swarna D. , Ali Zulfiqar , Abe Naohito , Sugandhika Suresh T. , Sandun Senerath T. P. , Khan Ikhlas A.
Published: March 2019

A new flavone glucoside, andrographidine G (1), was isolated from Andrographis paniculata together with 13 known compounds, including flavonoids, diterpenoids, and iridoids. The structure of 1 was established by spectroscopic and spectrometric techniques, including HR-ESI-TOF-MS, 1D and 2D NMR, and chemical methods. The known compounds were identified as andrographidine A (2), (2 R)-5-hydroxy-7,8-dimethoxyflavanone-5- O-β-D-glucopyranoside (3), acanthoside B (4), neoandrographiside (5), andropanoside (6), andrographiside (7), andrographolide (8), 14-deoxy-11,12-didehydroandrographiside (9), 14-deoxy-11,12-didehydroandrographolide (10), procumbide (11), procumboside (12), 6-epi-8- O-acetylharpagide (13), and curvifloruside F (14).