bluuebunny/crossref_metadata_2025 huggingface dataset:
Evaluation of Anti-glycation Activities of Phlorotannins in Human and Bovine Serum Albumin-methylglyoxal Models
Authors: Sugiura Shingo , Minami Yuya , Taniguchi Ryosuke , Tanaka Reiji , Miyake Hideo , Mori Tetsushi , Ueda Mitsuyoshi , Shibata Toshiyuki
Published: March 2019

In this study, the anti-glycation activities of phlorotannins contained in the Japanese Lessoniaceae ( Ecklonia cava, Eck. kurome, Eck. stolonifera, Eisenia arborea, and Eis. bicyclis) were tested using serum albumin-methlglyoxal (MGO) models. In the human serum albumin (HSA)-MGO model and the bovine serum albumin (BSA)-MGO model, the concentrations of crude phlorotannins at 50% inhibition (IC50) of fluorescent advanced glycation end products (AGEs) formation was in the range of 0.45 to 0.53 mg/mL and 0.43 to 0.53 mg/mL, respectively. Among the purified phlorotannins, phlorofucofuroeckol A with the benzobisbenzofuran skeleton had the highest inhibitory activities (IC50: 4.8 × 102 μM in HSA-MGO model and 4.1 × 102 μM in BSA-MGO model) against fluorescent AGEs formation, and showed about 13 times the inhibition in the HSA-MGO model, and about 20 times the inhibition in the BSA-MGO model, with respect to aminoguanidine hydrochloride, which was used as a positive control. In the test on MGO-scavenging activity using HPLC analysis, it showed that eckol and its simple dimers (dieckol and 8,8′-bieckol) had higher scavenging rate than aminoguanidine hydrochloride. In addition, it was revealed by liquid chromatography-electrospray ionization-mass spectrometry that eckol reacted with MGO and formed two adducts with it. These results strongly suggest that phlorotannins are novel and effective anti-glycation substances derived from natural plants.
Antibacterial and Antioxidant Activities of Leaf Extracts from Juglans sinensis, and its Phenolic Compositions
Authors: Han Kook-Il , Jung Eui-Gil , Patnaik Bharat Bhusan , Hong Chang-Il , Kim Young-Jun , Jung Seunghyeon , Han Man-Deuk
Published: March 2019

The beneficial properties of walnut depend on climate, genotype, and farming practices. We investigated the antibacterial and antioxidant activities of Juglans sinensis Dode cultivars grown in South Korea. Antibacterial activities were assessed using the minimum inhibitory concentration method and antioxidant activities using the 2,2-diphenyl-1-picryl-hydrazyl (DPPH) and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid (ABTS) assays. Ethyl acetate and chloroform extracts of J. sinensis leaves showed the highest antibacterial activity against Staphylococcus aureus SG511, Klebsiella aerogenes 1522E, and/or Enterobacter cloacae P99. DPPH and ABTS radical scavenging activities were found to be highest in the ethyl acetate extract. The total flavonoid and polyphenolic contents in the extract were 219.27 mg/g quercetin equivalents and 245.11 mg/g of gallic acid equivalents, respectively. Phenolic acids (gallic and vanillic) and flavonoids (catechin, rutin, and juglone) were detected by high performance liquid chromatography. We conclude that J. sinensis cultivars provide accessible sources of natural antibacterials and antioxidants.
Evaluation of Phenolic Compounds in Cistus creticus Bee Pollen from Greece. Antioxidant and Antimicrobial Properties
Authors: Atsalakis Emmanuel , Chinou Ioanna , Makropoulou Maria , Karabournioti Sofia , Graikou Konstantia
Published: March 2019

This study was carried out to evaluate the antioxidant properties of Greek endemic Cistus creticus L. (rock rose) bee pollen and define its phenolic compounds. In the framework of our scientific studies on Greek bee keeping products, we report herein our research on three Greek bee pollen samples from Cistus. Their pollinic spectra were obtained by Louveaux's quantitative microscopical analysis and it showed that one of them had Cistus sp. (Cistaceae) as abundant pollen (together with low percentage of Brassica sp. (Cruciferae). Throughout the chemical analysis of the extracts, several secondary metabolites of flavonoid structure have been identified as major components. Specifically, quercetin-7-rhamnoside (1), quercetin-3-neohesperidoside (2), kaempferol-3-neohesperidoside (3), myricetin-3-neohesperidoside (4), kaempferol-3-glucoside (5) and quercetin-3-glucoside (6) have been isolated and their structures were elucidated on the basis of spectral evidence. Moreover, the total phenolic and flavonoid content was estimated and the free radical scavenging activity was determined by DPPH and ABTS assays. The antimicrobial activity of the extracts was tested against six Gram-positive and -negative bacteria and three pathogenic fungi, and the butanol extract showed a very interesting broad antimicrobial profile (MIC 1.98•10−3 - 2.98•10−3 mg/ml) against all the assayed microorganisms.
Structural Basis for Great Protein-Binding Potential of Flavonoids: A Case Study of Quercetin
Authors: Gao Min , Tang Guang-Yan
Published: March 2019

Flavonoids exhibit a wide variety of biological effects and hold great protein-binding potential. In this study, we take quercetin, an extensively studied flavonoid, as an example to investigate the structural basis underlying their excellent protein-binding ability. Through calculating the pocket similarity of quercetin-binding proteins and comparing the binding modes between quercetins bound with different proteins, it was found that the great protein-binding capacity of quercetin not only arises from the structural conservation of target proteins, but also stems from its unique structure, in which molecular rigidity and flexibility is well-balanced and various chemical interactions could be formed between the small molecule and protein targets.
Antioxidant Sesquiterpenes from Penicillium citreonigrum
Authors: Yuan Wei-Hua , Zhang Ying , Zhang Peng , Ding Ru-Ru
Published: March 2019

A new chlorinated 11-noreremophilane-type sesquiterpene (1) together with 3-epiisopetasol, PR-amide and mycophenolic acid (2–4) were isolated from endophytic fungus Penicillium citreonigrum. The structures of 1–4 were elucidated by a combination of spectroscopic data and single-crystal X-ray diffraction analysis. Among them, compounds 1 and 4 showed moderate antioxidant capacities compared with ascorbic acid at 0.2 mM concentration.
Determination of Oleanolic and Ursolic Acids in Sambuci flos Using HPLC with a New Reversed-phase Column Packed with Naphthalene Bounded Silica
Authors: Gleńsk Michal , Włodarczyk Maciej
Published: March 2019

Elder flowers have traditionally been used for their anti-inflammatory properties. However little is known about triterpenoid components in this Pharmacopoeial herbal drug. Herein, we report the quantification of ursolic and oleanolic acid in Sambuci flos by HPLC method. These biologically active triterpenoids were effectively separated and quantified using the elaborated HPLC chromatographic method with a naphthalene bounded silica reversed phase column. In this study, a very simple mobile phase for HPLC was developed to simultaneously determine both acids and the factors affecting separation were also discussed. The average content of oleanolic acid and ursolic acid in the elder flowers determined by proposed method was 2.06 mg/g and 11.56 mg/g respectively. This study showed both successful applications of the new type of reversed phase column and important contribution of mentioned triterpenoids to elder flower composition presumably resulting in its pharmacological action.
Comparison of Anti-Inflammatory Activities of Structurally Similar Triterpenoids Isolated from Bitter Melon
Authors: Cheng Hsueh-Ling , Yang Ming-Hao , Anggriani Rista , Chang Chi-I
Published: March 2019

Momordica charantia L., or bitter melon, has been suggested to exhibit anti-inflammatory activity. In a previous study, three structurally similar triterpenes, namely 5β,19-epoxy-25-methoxycucurbita-6,23-diene-3β,19-diol (EMCD), 5β,19-epoxy-25-methoxycucurbita-6,23-dien-3β-ol (EMCO), and 5β,19-epoxy-19,25-dimethoxycucurbita-6,23-dien-3β-ol (EDMO), were isolated from bitter melon. EMCD has been shown to exhibit in vitro anti-inflammatory activity. In this study, the anti-inflammatory activities of EMCD, EMCO, and EDMO were compared. All three compounds were toxic to the RAW 264.7 macrophage cell line but not the FL83B cells. EMCD and EMCO inhibited tumor necrosis factor (TNF)-α-induced inducible nitric oxide synthase (iNOS) expression in FL83B cells, and the IC50 values were 19.8 and 25.7 μM, respectively. By contrast, EDMO did not effectively reduce iNOS expression. Furthermore, EMCD and EMCO suppressed other TNF-α-induced proinflammatory signals including the activation of inhibitor kappa B kinase complex, the phosphorylation of inhibitor of nuclear factor-κB, and the activation of c-Jun kinase. EMCD consistently exhibited a higher efficacy than did EMCO in these assays. Hence, the in vivo anti-inflammatory activity of EMCD was tested. EMCD clearly repressed 12- O-tetradecanoylphorbol-13-acetate (TPA)-induced ear edema in mice. In conclusion, differences in the functional group on carbon 19 do affect the anti-inflammatory activities of EMCD, EMCO, and EDMO. EMCD exhibited the highest anti-inflammatory activity among these molecules, and its in vivo anti-inflammatory activity was confirmed.
Cyclopiperettine, A New Amide from Piper nigrum
Authors: Ren Jie , Zeng Ting , Ali Zulfiqar , Wang Mei , Bae Jiyeong , Chittiboyina Amar G. , Wang Wei , Li Shunxiang , Khan Ikhlas A.
Published: March 2019

Cyclopiperettine, a new amide, was isolated from essential oil of Piper nigrum L. together with ten known compounds, including amides, monoterpenoids, and sesquiterpenoids. The structure of cyclopiperettine was established by 1D- and 2D- NMR and GC-MS techniques. Known compounds were identified as α-humulene, β-caryophyllene, caryophyllenol-II, β-elemene, elemol, 1-terpinen-4-ol, nerolidol, pellitorine, piperolein B and piperine. The crude oil and isolated compounds exhibited no antimicrobial activity against seven microbial strains up to 20 μg/mL.
Three New Bibenzyls from the Twigs of Smilax longifolia
Authors: Imura Yuka , Harada Kenichi , Kubo Miwa , Fukuyama Yoshiyasu
Published: March 2019

Three new bibenzyl compounds, 1-3, were isolated along with the previously known bibenzyls 4-6, one diarylpropanoid 7, and three diarylheptanoids 8-10 from the twigs of Smilax longifolia. The structures of the new compounds were elucidated by analyzing their spectroscopic data and comparing them with those of known compounds. Diarylheptanoid 9 exhibited potent lethality in the brine shrimp lethality test (BST).
High Anticancer Properties of Defatted Jatropha Curcus Seed Residue and its Active Compound, Isoamericanol A
Authors: Katagi Ayako , Sui Li , Kamitori Kazuyo , Suzuki Toshisada , Katayama Takeshi , Hossain Akram , Noguchi Chisato , Dong Youyi , Yamaguchi Fuminori , Tokuda Masaaki
Published: March 2019

Jatropha seeds have gained popularity as a biodiesel fuel resource. The process of biodiesel production from the seeds, however, also creates a tremendous amount of defatted residue as a byproduct. In this study, the potential for pharmaceutical usage of extracts from the defatted residue of crushed Jatropha curcus L. seed was examined. Organic and water fractions of both ethyl acetate (EtOAc) and methanol (MeOH) extracts from the seed residue exhibited an inhibitory growth effect on the human cancer cell lines hepatocellular carcinoma (HuH-7) and breast cancer (MCF-7). Later, the effect of isoamericanol A from the MeOH-organic fraction was compared across three human cell lines in search of human cell types suitable for treatment (HuH-7, MCF-7, cervical cancer (HeLa)). Our results indicate that the effect of three-day isoamericanol A treatment differs by cell type. Although effective to some extent, HeLa cell growth was most inhibited at the smallest dosage, whereas MCF-7 growth suffered the greatest inhibition at the highest dosage. Our findings reveal possibility for utilization of the Jatropha seed residue extract as well as its active compound, isoamericanol A, as practical cancer treatments for certain cell types in the future.
Antioxidant Activity of 1’-Hydroxyethylnaphthazarins and their Derivatives
Authors: Utkina Natalia K. , Pokhilo Natalia D.
Published: March 2019

The ABTS•+ radical cation scavenging activity of known (2-5, 9, 10) and new (6-8) 1’-hydroxyethylnaphthazarins and their products of esterification and etherification was evaluated and a structure-activity relationship was studied. It was shown, that the structure of side chains does not affect the radical scavenging activity of 1’-hydroxyethylnaphthazarins and their derivatives. The presence of methoxyl groups on the naphthazarin core slightly enhanced the antioxidant activity of compounds compared with compounds without methoxyl groups. The presence of the additional hydroxyl group on the naphthazarin moiety of isonorlomazarin (5) and its derivative (6) is essential for the activity.
In vitro Anthelmintic Activity of Two Aloe-derived Active Principles against Sheep Gastrointestinal Nematodes
Authors: Fichi Gianluca , Mattellini Matteo , Meloni Elisa , Flamini Guido , Perrucci Stefania
Published: March 2019

The in vitro anthelmintic activity on sheep gastrointestinal strongyle (GIS) eggs and larvae of 0.5% aloin and 0.1% aloe-emodin was investigated. From fresh faecal samples collected by ewes naturally infected by Haemonchus, Trichostrongylus and Teladorsagia nematodes, GIS eggs were isolated and cultivated in Petri dishes (100 eggs/dish). For the in vitro evaluation of the anthelmintic activity of tested compounds, the Egg hatch test (EHT), the Larval development test (LDT) and the Larval mortality/paralysis test (LMT) were used. In each assay, the activity of tested compounds was compared to untreated and treated (0.1% thiabendazole, TBZ) controls. Six repetitions were made through the experiment. Obtained data were statistically elaborated using the X2 test. In EHT, 0.5% aloin gave highly significantly different (P<0.01) results from the untreated controls. In LDT, both 0.1% aloe-emodin and 0.5% aloin almost completely prevented the larval development from L1 to L3, showing no significant differences (P<0.01) when compared to TBZ. In LMT, larval mortality observed in 0.5% aloin treated plates was significantly higher (P<0.01) than that observed in TBZ treated controls. These results show the in vitro anthelmintic properties on sheep GIS of the examined plant secondary metabolites. In LDT and/or LMT, the activity of 0.5% aloin and 0.1% aloe-emodin was comparable to or higher than that of the reference drug.
A New Cytotoxic Polyacetylenic Alcohol from a Sponge Callyspongia sp
Authors: Balansa Walter , Trianto Agus , de Voogd Nicole J. , Tanaka Junichi
Published: March 2019

A new cytotoxic polyacetylenic alcohol 1 was isolated from an Indonesian sponge Callyspongia sp. The structure of compound 1 was elucidated by spectral analyses and by applying modified Mosher's method. Compound 1 killed the cultured NBT-II rat bladder carcinoma cells at 5 and 10 μg/mL.
Structural Analysis of Two Bioactive Components of an Edible Mushroom, Termitomyces microcarpus
Authors: Bhanja Sunil Kumar , Rout Dilip
Published: March 2019

Two glucans, one α-glucan (TM-I) and one β-glucan (TM-II) were isolated from an edible mushroom, Termitomyces microcarpus by extraction with 5% NaOH/0.05% NaBH4, followed by a precipitation with 1 M acetic acid. The repeating units of two polysaccharides have been identified by means of NMR studies (1H, 13C, DEPT-135 and HSQC) and chemical investigations. The structures of repeating units of two polymers were established as
Ethanolic Extract of Rubus coreanus Fruits Inhibits Bone Marrow-Derived Osteoclast Differentiation and Lipopolysaccharide-Induced Bone Loss
Authors: Kim Tae-Ho , Jeong Chae Gyeong , Son Hyeong-U , Huh Man-Il , Kim Shin-Yoon , Kim Hong Kyun , Lee Sang-Han
Published: March 2019

The inhibition of osteoclast differentiation/bone resorption is a well-known therapeutic strategy for controlling pathological and postmenopausal bone loss. Natural products that specifically inhibit osteoclastogenesis could therefore be developed as antiresorptive drugs for the treatment of metabolic bone disorders characterized by excessive osteoclastic bone resorption. We therefore examined the effects of Rubus coreanus extract (eeRc) on receptor activator of nuclear factor kappa-B ligand (RANKL)-induced differentiation of bone marrow macrophages (BMMs) into osteoclasts and pit formation in vitro. Additionally, the in vivo effects of the eeRc were observed in mice with lipopolysaccharide (LPS)-induced bone erosion. In this study, we found that the ethanolic extract of Rubus coreanus fruits considerably suppressed the RANKL-induced differentiation of primary BMMs into osteoclasts and bone-resorbing activity of mature osteoclasts. Oral administration of eeRc attenuated LPS-induced bone loss in vivo, as demonstrated by the reversal of LPS-induced reduction in bone volume per tissue volume, bone mineral density, and trabecular number to some extent in eeRc-treated mice. In addition, eeRc slightly decreased the serum levels of C-terminal telopeptide fragments of type I collagen, the collagen-breakdown product generated by osteoclasts. Collectively, our results indicate that eeRc has the potential to inhibit bone loss by blocking osteoclast differentiation and could therefore be a promising natural product for the prevention and/or treatment of inflammatory bone loss.
Volatile Compounds in the Aerial Parts of Achillea collina Collected in the Urban Area of Vienna (Austria)
Authors: Chizzola Remigius
Published: March 2019

The variability of the essential oils produced by Achillea collina( A. millefolium agg., Asteraceae) has been studied. Plants were collected at five different sites in the urban area of Vienna, Austria, and separated into inflorescences, leaves and stems. A remarkable variability could be observed. Chamazulene was present in all samples and was the main oil compound in inflorescences and the lowest in stems. β-Pinene, sabinene, and 1,8-cineole were the most important monoterpenes and β-caryophyllene, germacrene D and caryophyllene oxide prevailed amongst the sesquiterpenes. Stems being low in volatiles showed high proportions of linoleic and palmitic acid in their oils. In comparison to other taxa of the A. millefolium group the present A. collina plants contained only very low proportions of borneol and camphor in their oils.
Chemical Composition of Essential Oil, Antioxidant, Antidiabetic, Anti-obesity, and Neuroprotective Properties of Prangos gaubae
Authors: Bahadori Mir Babak , Zengin Gokhan , Bahadori Shahram , Maggi Filippo , Dinparast Leila
Published: March 2019

Chemical composition of essential oil and the potential of Prangos gaubae for the management of public health problems such as Alzheimer's disease, obesity, Diabetes mellitus, and skin diseases were evaluated for the first time. In this direction, enzyme inhibitory effects, antioxidant activity, and total bioactive contents of the plant were determined. EO showed high acetylcholinesterase (2.97 mg GEs/g oil), α-amylase (1.35 mmol ACEs/g oil), α-glucosidase (38.84 mmol ACEs/g oil), and lipase (1.59 mmol OEs/g oil) inhibitory activities. Moreover, strong antioxidant effects were observed in antiradical (DPPH and ABTS), reducing power (CUPRAC and FRAP), total antioxidant, and metal chelating assays. Methanol extract exhibited promising DPPH radical scavenging activity (0.47 mmol TEs/g extract) and also high reducing power in CUPRAC (0.89 mmol TEs/g extract) and FRAP (0.52 mmol TEs/g extract) assays. All extracts showed low total flavonoid but high total phenolics content. Furthermore, they exhibited strong skin-care effect in tyrosinase inhibition assay. EO analysis showed the presence of germacrene D (26.7%), caryophyllene oxide (14.3%), ( E)-caryophyllene (13.8%), and spathulenol (11.3%) as the major volatile components. Results indicated that P. gaubae has promising potential for possible uses in food, cosmetic, and pharmaceutical industries due to its valuable phytoconstituents and biological activities.
Exploring the Effect of the Composition of Three Different Oregano Essential Oils on the Growth of Multidrug-Resistant Cystic Fibrosis Pseudomonas aeruginosa Strains
Authors: Maggini Valentina , Pesavento Giovanna , Maida Isabel , Nostro Antonella Lo , Calonico Carmela , Sassoli Chiara , Perrin Elena , Fondi Marco , Mengoni Alessio , Chiellini Carolina , Vannacci Alfredo , Gallo Eugenia , Gori Luigi , Bogani Patrizia , Bilia Anna Rita , Campana Silvia , Ravenni Novella , Dolce Daniela , Firenzuoli Fabio , Fani Renato
Published: March 2019

Oregano essential oils (EOs) could represent interesting therapeutic strategies to treat multidrug-resistant (MDR) pathogens as Pseudomonas aeruginosa, responsible for respiratory infections in cystic fibrosis (CF) patients. There could be a great variability in EOs composition when extracted from different plant species. The aim of this study was to chemically characterize and to test EOs, extracted from Origanum compactum, Origanum vulgare and Origanum vulgare var. hirtum, for in vitro antimicrobial activity against a panel of twenty MDR P. aeruginosa strains isolated from CF patients. EOs main components were carvacrol (71.8-73.8-47.1%), thymol (1.6-2.3-21.5%), p-cymene (11.6-7.4-10.8%) and γ-terpinene (1.7-3.1-8.4%). In general, the EOs showed inhibitory activity even at low concentration: 0.5% (v/v) OvEO and OhEO were able to inhibit the 80% of P. aeruginosa strains. Furthermore, the three EOs killed at least 75% of the strains at concentrations lower than 1% (v/v). Average MIC and MBC values were not significantly different. Similar levels of OEOs antimicrobial activities might be related to the fact that the main chemical class (i.e. carvacrol/thymol) is represented in quite similar percentages. Hence, the results of the present study shed light on a carvacrol/thymol-rich EO with a well-represented monoterpene hydrocarbons class as promising standardized antimicrobial herbal product.
Antifungal Activity Based Studies of Amaryllidaceae Plant Extracts
Authors: Nair Jerald J. , van Staden Johannes
Published: March 2019

The growth in demand for cosmetic, graft and organ transplant surgical procedures, the increased use of antineoplastic and immunosuppressive agents, as well as multidrug resistance are some of the factors responsible for the marked rise in fungal infection rates in recent years. Consequently, there have been renewed calls from both the public and private sectors for new and improved drug targets to replace existing antifungal therapies, many of which have been in clinical circulation for several decades. Plants select themselves in such endeavors owing to their superior numbers and vast chemical diversities. With this as a backdrop, this survey examines the antifungal activities of Amaryllidaceae plant extracts against various fungal pathogens. Good growth inhibitory activities (MICs <1 mg/mL) reported in several instances are noteworthy and could guide efforts targeting the active antifungal principles.
Iridoid Glycosides and Phenolic Glycosides from Buddleja asiatica with Anti-inflammatory and Cytoprotective Activities
Authors: Hien Truong Thi Thu , Quang Tran Hong , Tai Bui Huu , Nhiem Nguyen Xuan , Yen Pham Hai , Yen Duong Thi Hai , Cuong Le Canh Viet , Kim Youn-Chul , Oh Hyuncheol , Van Minh Chau , Van Kiem Phan
Published: March 2019

Chemical investigation of the methanol extract of the aerial parts of Buddleja asiatica resulted in the isolation of a new iridoid glycoside, buddlejasiaside A (1) and 11 known compounds: 6- O -[α-L-(4-isoferuloyl)-rhamnopyranosylcatalpol (2), specioside (3), verminoside (4), minecoside (5), 6- O -( p -hydroxybenzoyl)-ajugol (6), 6- O -caffeoyl ajugol (7), litanthosalin 8), eurostoside (9), 10- O -caffeoylaucubin (10), phlorizin (11), and garashangin (12). Their chemical structures were identified based on the MS and NMR spectroscopic analyses and comparing with the data reported in the literature. Compounds 1, 2, and 8-10 showed the modest inhibitory effects against nitrite production in LPS-stimulated BV2 microglia, with IC50 values ranging from 43.5-79.6 μM. Compounds 6, 7, and 11 protected HT22 hippocampal cells from glutamate-induced cell death, with EC50 values of 38.9, 14.8, and 27.1 μM, respectively.
High Level Production of δ-Guaiene, a Bicyclic Sesquiterpene Accumulated in Agarwood, by Co-expression of δ-Guaiene Synthase and Farnesyl Diphosphate Synthase Genes in Tobacco BY-2 Cells
Authors: Kato Takahiro , Taura Futoshi , Lee Jung-Bum , Kurosaki Fumiya
Published: March 2019

Two genes encoding δ-guaiene synthase ( GS) and farnesyl diphosphate synthase ( FPS) involved in δ-guaiene biosynthesis in Aquilaria microcarpa were co-expressed in tobacco ( Nicotiana tabacum) BY-2 cells by Agrobacterium -mediated transformation. GC-MS analysis revealed that the transformed tobacco cells liberated δ-guaiene, and the compound was found in the headspace of the culture but not accumulated either in the medium or in the cells. Tobacco cells transformed by solely GS produced 0.2 mg δ-guaiene /L culture, however, concentration of the compound elevated to 0.6 – 5.9 mg/L when GS and FPS were co-expressed in the cells. The stirring efficiency of the cell suspension was improved by the reduction of the culture volume in the vials, and this resulted in an appreciable increase in δ-guaiene content to the level of 102 mg/L culture. Addition of mevalonolactone as the precursor markedly activated δ-guaiene production, and content of the compound elevated to more than 400 mg/L culture. These results strongly suggested that tobacco BY-2 is a suitable host to construct the bio-production system of sesquiterpene compounds, and co-expression of FPS and appropriate sesquiterpene synthase genes in the cells should be the good strategy to establish the highly productive platform of this class of compounds.
A New Guaiane-type Sesquiterpenoid from a Bornean Soft Coral, Xenia stellifera
Authors: Phan Chin-Soon , Kamada Takashi , Ishii Takahiro , Hamada Toshiyuki , Vairappan Charles Santhanaraju
Published: March 2019

A new guaiane-type sesquiterpenoid, 10β- O-methyl-1αH,5αH-guaia-6-en-4β-ol (1) along with two known compounds, 10- O -methyl alismoxide (2) and alismoxide (3) were isolated from a population of Bornean soft coral Xenia stellifera. The structure of this metabolite was elucidated based on spectroscopic data such as NMR and HRESIMS. These compounds were evaluated for their biological activity against adult T-cell leukemia cell line.
Fusariumins B-D, Three New Alkylamine Octanoylated Derivatives from Fusarium sp
Authors: Liu Liang-Yan , Feng Tao , Li Zheng-Hui , Liu Ji-Kai
Published: March 2019

Three new alkylamine octanoylated derivatives, fusariumins B-D (1-3), and four known compounds 4-7 were isolated from the culture broth of the fungus Fusarium sp. Compounds 1-3 maintaining an unusual tetradecan-2-amine or tetradecan-3-amine moiety with an octanoyl group were characterized based on HRMS, 1D and 2D NMR spectroscopic data.
Optimization of Thin-layer Chromatography and High-Performance Liquid Chromatographic Method for Piper guineense Extracts
Authors: Mgbeahuruike Eunice Ego , Vuorela Heikki , Yrjönen Teijo , Holm Yvonne
Published: March 2019

In this study, a thin-layer chromatography (TLC) and a high performance liquid chromatographic (HPLC) methods were developed for the chemical profiling, qualitative and quantitative analysis of P. guineense extracts. To obtain a chromatogram with satisfactory resolution and favorable retention time, DryLab software was used to simulate and optimize a HPLC method for the analysis of P. guineense extracts. The aim was to achieve the best possible overall resolution while keeping the analysis time and solvent consumption to a minimum. With the optimized method, a total of 16 main components in the extract were separated with favorable resolution. Optimal TLC conditions were also developed using solvents of various solvent strength (ST) and solvent selectivity (PS) values. The mobile phase composition was systematically tested using various proportions of solvents differing in ST and PS values under the same experimental conditions. During the optimization, emphasis was set on achieving the best possible overall separation of the main components of the extracts (for example piperine). In addition, the effects of the developing chamber was tested using three types of unsaturated chamber conditions: horizontal chamber in sandwich configuration, horizontal chamber in non-sandwich configuration and twin-trough vertical chamber. During the study, a TLC method was developed, and the best mobile-phase composition giving favorable resolution of the bands was toluene: ethyl acetate (PS 6-4 corresponding to 60:40 % v/v). The developing chamber conditions did not affect the TLC separation efficacy in the analysis of P. guineense extracts. The HPLC method was applied to determine the percentage content of piperine in P. guineense. The piperine content was 0.43 % w/w, linearity (0.997), interday precision (% relative standard deviation (RSD), 1.6), intraday precision (% RSD, 2.7 – 5.9), recovery (98.4%), limit of detection (0.001 μg /mL) and limit of quantification (0.003 μg /mL).
Anti-HIV Activity of Alkaloids from Dasymaschalon echinatum
Authors: Bunteang Samreang , Chanakul Waraporn , Hongthong Sakchai , Kuhakarn Chutima , Chintakovid Watcharra , Sungchawek Natthapat , Akkarawongsapat Radeekorn , Limthongkul Jitra , Nantasaen Narong , Reutrakul Vichai , Jaipetch Thaworn
Published: March 2019

Bioassay-guided fractionation of the aerial parts of Dasymaschalon echinatum led to the isolation of five known aristolactams; aristolactam AII (1), aristolactam BII (2), piperolactam A (3), piperolactam C (4), and goniopedaline (5), together with two aphorphine alkaloids; duguevalline (6) and noraristolodione (7) and two amide derivatives; asperphenamate (8), and N -benzoyl-L-phenylalaninol (9). Alkaloids 2 and 7 were isolated for the first time from the Dasymaschalon genus. The anti-HIV 1 reverse transcriptase (RT) activity of all isolated compounds was determined. Except for aristolactam BII (2), this is the first report of the anti-HIV 1-RT activity of compounds 1 and 3-9. Compounds 1, 3, 5, 6 and 8 showed weak anti-HIV 1-RT inhibitory activity with IC50 ranging from 112.74 to 225.55μM.
A New Purine Derivative from the Roots of Phyllanthus flexuosus
Authors: Zhu Guanlin , Wang Hongying , Gan Kunrong , Gao Heng , Li Wei
Published: March 2019

A new purine derivative, 1-methyl-3-isopentenylisoguanine (1), together with six known compounds (2-7), was isolated from the roots of Phyllanthus flexuosus. The newly isolated structure was established by means of extensive spectroscopic analysis and single-crystal X-ray diffraction experiment. All isolates were evaluated for their in vitro cytotoxicities against two human hepatocellular carcinoma cell lines (HepG2 and SMMC-7721) by CCK-8 assays. Among them, three cleistanthane diterpenes (2–4) exhibited different levels of cytotoxicities against these cells with IC50 values ranging from 27.34 to 53.28 μM. Furthermore, acetylcholinesterase inhibitory effect for the new purine derivative was also assessed.
Cytotoxicity against Cholangiocarcinoma and HepG2 Cell Lines of Lignans from Hernandia nymphaeifolia
Authors: Suthiwong Jittra , Boonloh Kampeebhorn , Kukongviriyapan Veerapol , Yenjai Chavi
Published: March 2019

Eleven lignans (1-11) were isolated from the seed of Hernandia nymphaeifolia. Most of the lignans exhibited strong to moderate cytotoxicity against cholangiocarcinoma KKU-M156 and HepG2 cell lines. Compounds 4 and 8 showed cytotoxicity against the KKU-M156 cell line with IC50 values of 5.2 μ M (Emax 96%) and 5.4 (Emax 59%) μM, respectively. In the cases of cytotoxicity against the HepG2 cell line, compounds 2, 3, 4, and 8 showed cytotoxicity with IC50 values of 1.7 M (Emax 84%), 4.1 μM (Emax 74%), 4.5 μM (Emax 68%), and 5.2 μM (Emax 78%), respectively.
Distinguishing Glycyrrhiza species using NMR-based Metabolomics
Authors: Suzuki Ryuichiro , Nakano Fusako , Ohno Hirokazu , Murakami Toshiyuki , Okada Yoshihito , Shirataki Yoshiaki
Published: March 2019

Glycyrrhiza species are widely used as natural medicines and as well as food additives. Quality control during methods development is therefore critically important. In this study, we conducted NMR-based metabolomics analyses to distinguish Glycyrrhiza species ( G. glabra, G. uralensis, and G. inflata). Principle component analysis (PCA) of 1H-NMR spectra of extracts of Glycyrrhiza species enabled categorization of the three species. We conducted solid-phase extraction of methanol extracts of Glycyrrhiza roots prior to NMR measurements. Most studies of Glycyrrhiza species have used mass spectra to distinguish species. By conducting solid-phase extraction prior to NMR analysis, we could distinguish species clearly by PCA score plots. These results indicate that solid-phase extraction enables clear discrimination of Glycyrrhiza species in NMR metabolomics analyses. Furthermore, saponin fractions prepared by solid-phase extraction from water extracts were also discriminated according to the species using NMR metabolomics. Saponins such as glycyrrhizin are important constituents of Glycyrrhiza species. These results thus indicate that there are species-specific differences in root saponins in Glycyrrhiza.
Genoprotective Effects of Thai Royal Jelly against Doxorubicin in Human Lymphocytes in Vitro
Authors: Jenkhetkan Wantha , Thitiorul Sumon , Jansom Chalerm , Ratanavalachai Treetip
Published: March 2019

Genoprotective effects of royal jelly (RJ) treatments against doxorubicin (DXR), a potent genotoxic chemotherapeutic compound in human lymphocytes were investigated using the sister chromatid exchange (SCE) assay, and their molecular mechanisms were examined by Western blot. Results showed that RJ pretreatments at 0.005 and 0.05 mg/mL significantly decreased DXR-induced SCE levels by 1.2-fold (p<0.05), compared to DXR treatment alone. Co-treatment of RJ (5 mg/mL) with DXR (0.2 μg/mL) increased the ratios of BCL2/BAX (1.5-fold), NRF2/BAX (1.3-fold), and hTERT/BAX (1.1-fold) compared to the DXR alone, suggesting its power in enhancing cell survival, antioxidative potentials, and longevity over cell death. The study suggested that RJ protected human cells from DXR-induced genotoxicity, possibly mediated through anti-apoptotic, anti-oxidative, and anti-aging properties of RJ. However, lower doses of RJ co-treatments enhanced DXR toxicity. Further, in vivo molecular study is required to validate this in vitro study.
Essential Oil Composition, Antioxidant, Anticholinesterase and Anti-tyrosinase Activities of Two Turkish Plant Species: Ferula elaeochytris and Sideritis stricta
Authors: Deveci Ebru , Tel-Çayan Gülsen , Duru Mehmet Emin
Published: March 2019

The aim of the present study is to characterize chemical compositions and antioxidant, anticholinesterase and anti-tyrosinase activities of Ferula elaeochytris and Sideritis stricta essential oils. The hydrodistilled essential oils were analyzed by GC/FID and GC/MS. A total of thirty-three and twenty-seven compounds representing 99.6 % and 99.4 % were identified in F. elaeochytris and S. stricta, respectively. The main compounds of essential oil of F. elaeochytris were β-cubebene (21.3 %), caryophyllene oxide (17.5 %) and β-caryophyllene (14.9 %), while the major compounds of S. stricta essential oil were δ-cadinene (18.3 %), cubenol (17.6 %) and β-caryophyllene (14.4 %). The antioxidant activity was tested by β-carotene-linoleic acid, DPPH free radical scavenging, ABTS cation radical scavenging, CUPRAC and metal chelating assays. The essential oil of F. elaeochytris showed the highest antioxidant activity in all assays. Also, the anticholinesterase and anti-tyrosinase activities of essential oils were performed against acetylcholinesterase (AChE), butyrylcholinesterase (BChE) and tyrosinase enzymes. F. elaeochytris essential oil indicated the highest anticholinesterase and anti-tyrosinase activities as well. This is the first report describing antioxidant, anticholinesterase and anti-tyrosinase activities of essential oils of F. elaeochytris and S. stricta.
Novel Ent-Kaurene Glycosides with Eight Glycosyl Units from Stevia rebaudiana
Authors: Prakash Indra , Wang Bin , Ma Gil , Harrigan George , Sukits Steven F. , Devkota Krishna P. , Charan Romila D. , Donovan Ryan , Snyder Tara M.
Published: March 2019

Several steviol glycosides from Stevia rebaudiana are associated with extremely potent sweetness and are sought-after as low-calorie alternatives to sucrose. With the exception of a few nine sugar glycosides, steviol glycosides described in the scientific literatures contain less than a total of seven glycosyl units. We present here two new steviol glycosides, rebaudioside VIIIa (1) and VIIIb (2) containing eight sugar units isolated from S. rebaudiana Bertoni. The complete structure elucidation of these ent -kaurene diterpene glycosides with eight sugar units was completed using 1D- and 2D-NMR spectroscopy experiments (1H, 13C, 1H-1H COSY, 1H-13C HSQC-DEPT, 1H-13C HMBC, 1D TOCSY, and 1H-1H ROESY) and mass spectral data. Both compounds have four glycosyl units each attached to the C-13 and C-19 positions of aglycone core but vary in the glycosylation pattern and number of glucose and rhamnose units. This report therefore expands the catalog of highly glycosylated components from S. rebaudiana.
Oleanane-type Triterpenes with Highly-Substituted Oxygen Functional Groups from the Flower Buds of Camellia sinensis and Their Inhibitory Effects against NO Production and HSV-1
Authors: Yoneda Taichi , Nakamura Seikou , Ogawa Keiko , Matsumoto Tomoko , Nakashima Souichi , Matsumura Kiriko , Tanaka Aoi , Ryu Kaori , Fukaya Masashi , Fujimuro Masahiro , Yoshikawa Masayuki , Matsuda Hisashi
Published: March 2019

Acylated oleanane-type triterpenes named chakasapogenins I (1), II (2), and III (3) were isolated from the hydrolysis product of the extract obtained from the flower buds of Camellia sinensis. The chemical structures of new triterpenes were elucidated on the basis of chemical and physicochemical evidence. chakasapogenin III (3) inhibited nitric oxide (NO) production in lipopolysaccharide- (LPS) activated RAW264.7 macrophages. In addition, R1-barrigenol (7) showed antiviral effect at 10μM against herpes simplex virus type-1 (HSV-1).
Triterpene Glycosides from the Sea Cucumber Eupentacta fraudatrix. Structure and Cytotoxic action of Cucumarioside D with a Terminal 3-O-Me-Glucose Residue Unique for this Species
Authors: Silchenko Alexandra S. , Kalinovsky Anatoly I. , Avilov Sergey A. , Popov Roman S. , Kalinin Vladimir I , Andrijaschenko Pelageya V. , Dmitrenok Pavel S. , Yurchenko Ekaterina A.
Published: March 2019

New minor triterpene glycoside, cucumarioside D (1) identified earlier as a candidate to new glycoside using LC-ESI QTOF-MS has been isolated from the sea cucumber Eupentacta fraudatrix as individual substance. The structure of the glycoside was elucidated using 2D NMR spectroscopy and MS. The glycoside has non-sulfated pentasaccharide carbohydrate chain branched by the second sugar (quinovose) and having 3-O-methylglucose as a terminal monosacharide residue that is an unique structural feature of sea cucumber triterpene glycosides from this species. A moderate cytotoxic activity of the glycoside 1 against the ascyte form of Echlich carcinoma cells and hemolytic activity has been found.
Preparation and Regeneration of Protoplasts from the Ethyl Vincamine Producing Fungus CH1 (Geomyces sp.)
Authors: Ren Na , Liu Jiajia , Yang Dongliang , Liu Xiong , Zhou Jing , Peng Yingzi
Published: March 2019

Vinpocetine, a semi-synthetic compound derived from the alkaloid vincamine, exhibits effective pharmacological activities for the treatment and prevention of cerebrovascular circulation and vascular cognitive disorders. Vinpocetine can be produced through a one-step chemical reaction beginning with ethyl vincamine, and a two-step chemical reaction beginning with vincamine. In our previous study, the endophytic fungus CH1, Geomyces sp., was isolated and identified as a producer of ethyl vincamine, which was first obtained by endophytic fungal fermentation. However, the production was largely limited. Fungal protoplasts are a valuable experimental tool for physiological and genetic research such as protoplast fusion, gene transfer and metabolite production. In this paper, we optimized some key factors for the preparation and regeneration of protoplasts from strain CH1. Using an enzymes mixture consisting of cellulase (2.0%, w/v), glusulase (3.0%, w/v) and driselase (1.0%, w/v) in osmotic stabilizer (0.7 mol/L NaCl), the highest yield of protoplasts (6.78×107/mL) was obtained with mycelia after 72 h at pH 5.0-6.0 by digesting for 1.5 h at 30°C. After purification of the prepared protoplasts, they were regenerated in the regeneration medium using a bilayer plate culture method.
Antimicrobial Activity of the Constituents of Dalbergia tonkinensis and Structural-Bioactive Highlights
Authors: Son Ninh The , Oda Masataka , Hayashi Naoki , Yamaguchi Daiki , Kawagishi Yu , Takahashi Fumi , Harada Kenichi , Cuong Nguyen Manh , Fukuyama Yoshiyasu
Published: March 2019

The vulnerable plant Dalbergia tonkinensis Prain, is a rare species, native to Vietnam. Phytochemical investigations and biological evaluations of this species are quite limited. Antimicrobial screening has suggested that, at the low dose of 1.0 mg/mL, the methanol extracts of the leaf, stem bark, and root, as well as chloroform fraction of heartwood can serve as useful sources against seven gram-positive skin microbacteria, Bacillus cereus (ATCC27522), Escherichia coli (JM109), Staphylococcus aureus (ATCC25923), Staphylococcus epidermidis (ATCC14990), Streptococcus pneumonia (ATCC49619), Streptococcus pyogenes (ATCC12344), and Vibrio parahaemolyticus (RIMD2210010), and four oral gram-positive microbacteria Streptococcus mutans (ATCC 25175), Streptococcus mitis (ATCC903), Streptococcus sobrinus (ATCC 33478), and Porphyromonas gingivalis (ATCC33277), with an inhibitory percentage of 60-80% growth for several strains Bacillus cereus, Escherichia coli, and Streptococcus pneumonia. We further assessed antimicrobial activities of the enriched diverse flavonoids from chloroform fraction of its heartwood. Extensive structural activity relationship studies showed structure function closely related to the antimicrobial activity, in which methoxylation at C-2’, and 4’ in isoflavanones, hydroxylation at C-3’ in flavones, substitution at C-5 in isoflavones, and lactone opened ring in neoflavonoids were found to increase the effective inhibitions. In the second antimicrobial assessment, the isolated flavonoid liquiritigenin showed the MIC values of 50, and 100 μg/mL against the microbacterial strains Staphylococcus aureus subsp. aureus (ATCC 11632), and Aspergillus niger (439), respectively, whereas the MIC value of 100 μg/mL was assignable to biochanin A against microbacterium Staphylococcus aureus subsp. aureus.
Development of a Bioproduct for Medicinal Use with Extracts of Zuccagnia-type Propolis
Authors: Salas Ana , Zampini Iris Catiana , Maldonado Luis , Isla María Inés
Published: March 2019

Propolis with a botanic origin in Zuccagnia punctata Cav. (Fabaceae), a plant species widely distributed in the Argentinean Monte region, was used to produce a standardized propolis extract by biological activity and chemical composition. In this paper the effect on microorganisms isolated from otitis was determined. The extract was active against different Staphylococcus strains with MIC and MBC values (75 and 150 μg DE/mL, 200 and 600 μg DE/mL, respectively) and with MIC values of 800 μg DE/mL against Proteus mirabilis. A pharmaceutical product, ear drops containing this extract as bioactive was developed. Stability of ear drops was evaluated for 6 months, and their biological activity, physical and phytochemical properties were preserved. Ear drops showed inhibitory activity on pro-inflammatory enzymes such as lipoxygenase (IC50 values 90 and 100 μg DE/mL), free radical-scavenging effect (SC50 values 23 and 30 μg DE/mL), antihelmintic (LC50 values 70 and 71 μg DE/mL), anti-candida (400 μg DE/mL) and antibacterial activity against Gram-positive bacteria (200 μg DE/mL) at zero time and during six month-storage, respectively. The content of two chalcones, chemical markers of Zuccagnia -type propolis was quantified and its level was maintained while stored at room temperature. Its toxicity was also assayed. Our results are interesting since the extract and ear drops of Zuccagnia -type propolis developed could be promising for use in alternative medicine or phytomedicine as antibacterial, anti-candida, antihelmintic, anti-inflammatory and antioxidant.
Argentinean Larrea Dry Extracts with Potential Use in Vaginal Candidiasis
Authors: Moreno María Alejandra , Córdoba Susana , Zampini Iris Catiana , Mercado María Inés , Ponessa Graciela , Sayago Jorge Esteban , Ramos Liudis Leidy Pino , Schmeda-Hirschmann Guillermo , Isla María Inés
Published: March 2019

Larrea divaricata (Ld), Larrea cuneifolia (Lc) and Larrea nitida (Ln) are shrubs occurring in Northwestern Argentina used in traditional medicine to treat fungal and bacterial infections and as anti-inflammatory. Antibacterial and antifungal activity of several Larrea species has been reported. However, their potential use in vaginal infections has been so far not assessed. The aim of this work was to determine the botanical difference between Larrea species, the chemical composition and the activity of Larrea dry extracts (DE) on Candida species isolated from vaginal infections and to assess their potential as antioxidant agents because infections are usually associated with oxidative processes. The main botanical difference between Larrea species resides in the morphology and shape of leaf, leaflets and stipules, presence or absence of mucron and rachis, percentage of coalescence of the leaflets. The position and abundance of the sclerenchymatic tissue at the mind vein and petiole transection allows the differentiation of the three species. The profile of phenolic compounds in the Larrea DE was determined. HPLC-ESI-MS/MS analysis of DE allowed the identification of 2 flavonoids and 10 lignans. Trihydroxy-6,7′cyclolignan was found only in L. divaricata and dihydroxy-methoxy-epoxylignan in L. cuneifolia and L. nitida, nordihydroguaiaretic acid (NDGA) was found in the three species. All extracts showed antioxidant capacity. The DE showed to be effective against Candida albicans and non-albicans strains. According to our results, the local vaginal use of Larrea DE in the concentration range of MIC values for Candida species does not affect the Lactobacillus normal vaginal microbiota. This work adds evidence to the potential use of Larrea DE as phytomedicine in vulvovaginal candidiasis with multiple effects, including antifungal and antioxidant activity.
The Mechanisms of Shcisandrol A in Immune Function Modulation in Immunosuppressed Mice
Authors: Xu Guangyu , Liu Xu , Wang Chunmei , Li He , Zhang Chengyi , Chen Jianguang , Sun Jinghui
Published: March 2019

The population of people with immunodeficiency is increasing due to the accelerating pace of life, increase in work pressure, and lack of exercise, irregularity of diet and rest, and problems of environmental pollution. Chinese herbal medicines have been shown to improve immunity, with little to no side effects. In recent years, studies have shown that Shcisandrol A (Sch A) regulates immune functioning and inhibits inflammation of the nervous system. The current study used gene expression profiling of spleen tissue to screen differentially expressed genes related to Sch A treatment on cyclophosphamide (Cy)-induced immunosuppressed mice. The differentially expressed gene-related pathways were analyzed by gene ontology function cluster analysis and qPCR. Five genes related to immune functioning were found to be regulated by Sch A treatment: Mapk3, Pik3r1, Pik3r5, Ikbkg, and Cd247. qPCR analysis showed that all five genes were significantly down-regulated in mice treated with Sch A compared to untreated immunosuppressed mice. These results suggest potential mechanisms through which Sch A regulates immune functioning.