bluuebunny/crossref_metadata_2025 huggingface dataset:
Guaiane Sesquiterpenes from the Rhizome of Curcuma xanthorrhiza and Their Inhibitory Effects on UVB-induced MMP-1 Expression in Human Keratinocytes
Authors: Park Ji-Hae , Mohamed Mohamed Antar Aziz , Thi Nhan Nguyen , Seo Kyeong-Hwa , Jung Ye-Jin , Shrestha Sabina , Lee Tae Hoon , Kim Jiyoung , Baek Nam-In
Published: March 2019

A new guaiane sesquiterpene, (1 R,4 S,5 S,10 R)-10-methyl guaianediol (1), along with five known compounds, 10-methylalismoxide (2), (+)-alismoxide (3), isozedoarondiol (4), zedoarondiol (5), and zedoalactone B (6), were isolated from the rhizomes of Curcuma xanthorrhiza Roxb. Compounds 1-6 were isolated from this plant for the first time. Chemical structures were determined using nuclear magnetic resonance (NMR), electron ionization mass spectrometry (EI/MS), polarimetry, circular dichroism (CD), and infrared spectroscopy (IR). Compounds 3 and 4 decreased MMP-1 expression in UVB-treated human keratinocytes by about 8.9-fold and 7.6-fold at the mRNA level, and by about 9.2-fold and 6.6-fold at the protein level, respectively. Results indicate that the isolated compounds have anti-aging effects by inhibiting MMP-1 expression in skin cells.
A Novel Cycloartane Triterpenoid Bisdesmoside from Actaea vaginata
Authors: Zou Qiongyu , Wu Meichun , Zhu Yindi , Shen Jinping , Ma Guoxu , Xu Xudong , Chen Gui , Zhang Li , Zhao Zijian , Chen Dizhao , Wu Haifeng
Published: March 2019

A new cycloartane triterpenoid bisdesmoside, soulieoside S (1), was isolated from the ethanolic extract of rhizomes of Actaea vaginata. The structure was determined by extensive spectroscopic analysis including 1D- and 2D NMR and HRESIMS, as well as chemical methods. Compound 1 was evaluated for its cytotoxic activities against HepG2, MDA-MB231 and A549 cancer cell lines.
A New Steroidal Glycoside Granulatoside C from the Starfish Choriaster granulatus, Unexpectedly Combining Structural Features of Polar Steroids from Several Different Marine Invertebrate Phyla
Authors: Ivanchina Natalia V. , Malyarenko Timofey V. , Kicha Alla A. , Kalinovsky Anatoly I. , Dmitrenok Pavel S. , Stonik Valentin A.
Published: March 2019

A new unique steroidal glycoside, granulatoside C (1), was isolated from the ethanol extract of the starfish Choriaster granulatus. The structure of 1 was elucidated by extensive NMR and ESI-MS techniques as (20 R)-16,21- O-di-(P-D-fucopyranosyl)-24-methyl-cholesta-5,24(28)-diene-3p,7a,16a,21-tetraol (1). This glycoside is unusual one, because combines some characteristic structural peculiarities of steroids from several different phyla of marine invertebrates, it has a range of structural features that not previously found in starfish polyhydroxysteroidal glycosides, such as Δ5-3β,7α,16α-trihydroxysteroidal nucleus, Δ24(28)-21-hydroxy-24-methyl-cholestane side chain and 16,21-diglycosylation by D-fucopyranosyl residues, but also characteristic of sponges, ophiuroids and soft corals, respectively.
Synthesis of an Antileukemic Pyrone from Alternaria phragmospora
Authors: Qu Yang , Kraus George A.
Published: March 2019

Antileukemic pyrone 1 was synthesized by way of a five-step procedure from 4-Hydroxy-5-methoxycarbonyl-6-methyl-2-pyrone (8). This is the first synthesis of 4-methoxy-6-methyl-5-(3-oxobutyl)-2H-pyran-2-one (1).
New Primula-type Flavones from Exudates of Selected Dionysia spp. (Primulaceae)
Authors: Hinterdobler Wolfgang , Valant-Vetschera Karin M. , Brecker Lothar
Published: March 2019

Hitherto unstudied Dionysia leucotricha and D. denticulata as well as new accessions of already studied species were analyzed for their exudate flavonoid profile. Results were compared with those of closely related species by HPLC-reinvestigation of existing exudate solutions. In addition to already known compounds typical of the Primula assemblage, three compounds were isolated from D. bryoides and identified as 2’-hydroxy-3’-methoxyflavone (1), 2’,3’-dimethoxyflavone (2) and 3’,5’-dimethoxyflavone (3), respectively, by HPLC and NMR. All compounds are new for the genus Dionysia, with compound 3 being novel and yet only described from synthesis. The occurrence of Primula-type flavones in Dionysia and the rare reports from genera outside Primulaceae are commented briefly.
DNA Topoisomerase I Inhibitory Activity of Quinochalcone C-glycosides from the Florets of Carthamus tinctorius
Authors: Yue Shi-Jun , Wang Wen-Xiao , Qu Cheng , Xin Lan-Ting , Tang Yu-Ping , Duan Jin-Ao , Wang Chang-Yun
Published: March 2019

The DNA topoisomerase (Topo) I inhibitory activity of six quinochalcone C-glycosides (QCGs) isolated from the florets of Carthamus tinctorius were evaluated in vitro. Among them, anhydrosafflor yellow B (AHSYB, 4) and carthorquinoside B (6) could inhibit DNA Topo I at concentrations as low as 100 μM. Molecular docking study revealed that both of them have the capacity to stabilize Topo I-DNA cleavage complex in silico interacting with the essential binding sites, such as Arg364, Thr718 and TGP11. Besides, both compounds 4 and 6 exhibited no antitumor activity by in vitro cytotoxicity assays.
A New Glycoside and in vitro Evalution of α-Glucosidase Inhibitory Activity of Constituents of the Mangrove Lumnitzera racemosa
Authors: Phuong Nguyen H. , Thuy Nguyen T. L. , Duc Nguyen T. , Tuyet Nguyen T. A. , Mai Nguyen T. T. , Phung Nguyen K. P.
Published: March 2019

From Lumnitzera racemosa Willd., a new glycoside, 2- O-galloyl-α-L-rhamnopyranosyl-(3→4’)-3’- O-galloyl-α-L-rhamnopyranose (1), as well as nine known compounds were isolated. Their chemical structures were elucidated by spectroscopic data analysis as well as comparison with the ones in the literature. The evaluation of α-glucosidase inhibitory activity of the extracts and some isolated compounds was measured.
Salicylic Glycosides in Salix mucronata with Antioxidant and Antiinflammatory Activities
Authors: Dissanayake Amila A. , Zhang Chuan-Rui , Gaber Mohamed K. A. , Nair Muraleedharan G.
Published: March 2019

The leaves of Salix mucronata (safsaf willow), widely distributed along the Nile River in Egypt, is used in traditional medicine. This prompted us to examine the bioactive components in its leaves using in-vitro antioxidant and antiinflammatory assays. Bioassay-guided purification of the methanolic extract afforded six known phenolic compounds (1-6). Hexane extract did not contain bioactive compounds except chlorophyll. Pure isolates 1-3 and 6 inhibited lipid peroxidation (LPO) by 56-86% at 5 μg/mL and cyclooxygenase enzymes (COX-1 and -2) by 22-75% at 25 μg/mL. This is the first report on the bioassay-guided characterization of constituents in S. mucronata leaves. Our results support the anecdotal medicinal claims of safsaf leaves.
Caffeic Acid Esters Affect Intracellular Oxidation and Vitality of Yeast Saccharomyces cerevisiae Cells
Authors: Petelinc Tanja , Medved Manca , Polak Tomaž , Jamnik Polona
Published: March 2019

The effect of four esters of caffeic acid, caffeic acid methanol ester (CAME), caffeic acid ethanol ester (CAEE), caffeic acid isopropyl ester (CAIPE) and caffeic acid phenethyl ester (CAPE) on intracellular oxidation, vitality and viability of the yeast Saccharomyces cerevisiae as a model eukaryotic organism was investigated. Results showed that each ester showed its own behavior at the concentrations tested. For CAPE, CAIPE and CAEE decreased intracellular oxidation and simultaneously increased cellular vitality with no changes in cellular viability compared to the control were determined. Additionally, a combination of CAIPE or CAPE with ethanolic propolis extract was observed to be more effective in decreasing intracellular oxidation compared to propolis extract alone.
Copper(II) Sulfate Stimulates Scopoletin Production in Cell Suspension Cultures of Angelica archangelica
Authors: Siatka Tomáš , Chlebekb Jakub , Hoštálková Anna
Published: March 2019

Plant tissue cultures represent an attractive alternative source of valuable natural substances. Many strategies have been proposed for improving production yields, among others, elicitation with heavy metals. In this work, the effect was investigated of copper(II) sulfate (at concentrations of 0, 0.1, 0.5, 1, 5, 10, 50, 100, and 200 μM) on scopoletin production, as well as on cell growth in Angelica archangelica (angelica) suspension cultures with the cultures maintained in the dark and in the light. Copper(II) sulfate up to 100 μM did not significantly affect either fresh or dry biomass in the cultures grown in either the dark or light, but at 200 μM they were slightly reduced. Copper(II) sulfate stimulated accumulation of scopoletin in a dose-dependent manner both in the cells and in the culture medium. Moreover, concerning scopoletin production, the cultures showed different sensitivity to copper ions depending on light conditions. The highest yields of scopoletin were found at copper concentrations of 5-50 μM and 50 μM in the light- and dark-grown cultures, respectively. Copper(II) sulfate has proved to be a suitable elicitor for improvement of scopoletin accumulation in cell suspension cultures of A. archangelica.
Comparative Analysis of Phenolic Compounds in Seven Hypericum Species and Their Antioxidant Properties
Authors: Zdunic Gordana , Godjevac Dejan , Savikin Katarina , Petrovic Silvana
Published: March 2019

A comparative analysis of the phenolic compounds in the 70% EtOH extracts of Hypericum acutum, H. androsaemum, H. barbatum, H. hirsutum, H. maculatum, and H. richeri has been carried out using high-performance liquid chromatography coupled with photodiode array UV detection and high resolution TOF mass spectrometry. Quercetin, astilbin, I3, II8-biapigenin, orientin, 2”- O-acetylorientin, three phenolcarboxylic acids, and eight flavonols 3- O-glycosides were identified in the extracts on the basis of their on-line UV spectra, accurate mass spectral data, and in comparison of retention times with those from the standards. Fingerprint analysis of the extracts revealed significant differences in the qualitative and quantitative chemical composition of the studied species. Antioxidant assays with various reaction mechanisms were used including ferric reducing antioxidant power (FRAP) assay, DPPH, ABTS, superoxide anion radical scavenging capacity and inhibition of liposome peroxidation induced by Fe2+. The most potent were extracts of H. acutum and H. maculatum indicating this Hypericum species interesting for further research aimed as a potentially new source of biologically active compounds.
Pectolinarigenin Suppresses Pancreatic Cancer Cell Growth by Inhibiting STAT3 Signaling
Authors: Zhou Bin , Hong Zhong , Zheng Hailun , Chen Min , Shi Lingyi , Zhao Chengguang , Qian Haixin
Published: March 2019

Pancreatic cancer is among the leading causes of cancer-related deaths with extremely poor prognosis. Thus, novel and effective therapies need to be developed to improve the poor survival rates of patients with advanced pancreatic cancer. Pectolinarigenin, a flavonoids compound, has been shown to possess numerous biologic activities such as anti-inflammation and anti-cancer. However, the function and mechanism of pectolinarigenin in pancreatic cancer are still not well understood. We evaluated the antitumor effects of pectolinarigenin, an active component of a medicinal plant. Pectolinarigenin exerted a strong antitumor effect in pancreatic cancer cell lines. Colony formation assay and wound healing assay indicated that pectolinarigenin inhibited cell viability and cell migration. Treatment with pectolinarigenin induced apoptosis and decreased phosphorylation of STAT3. Pectolinarigenin modulates the STAT3 signaling module, thereby inducing cytotoxicity in pancreatic cancer cells. This result verifies the potential use of pectolinarigenin as a new therapeutic agent for the treatment pancreatic cancer.
LC-MS/MS Analysis of Flavonoid Compounds from Zanthoxylum zanthoxyloides Extracts and Their Antioxidant Activities
Authors: Tine Yoro , Yang Yin , Renucci Franck , Costa Jean , Wélé Alassane , Paolini Julien
Published: March 2019

Flavonoids are a large group of phenolic secondary metabolites having a wide range of biochemical and pharmacological effects. In this work, a targeted liquid chromatography (LC) coupled with tandem mass spectrometry (MS2) was used to characterize the flavonoid compositions of methanolic plant extracts from separated parts (fruits, leaves, stems, trunk barks, and root barks) of Zanthoxylum zanthoxyloides. Nine flavonoids were reported in this species, including three flavanones, five flavonols and one flavone. Quantitative analysis of flavonoid profiles from Z. zanthoxyloides extracts is useful to a better understanding of the pattern and distribution of metabolites in extract samples. The concentrations of two glycosylated flavanones (neohesperidin and hesperidin) and one flavonol (quercetin) were higher in root and trunk samples compared to fruit samples. These compounds were reported in small amounts in the stem and leaf samples. In contrast, four flavonols (hyperoside, quercetin-3- O-glucopyranoside, datiscin and quercitrin) were present in significant levels only in the leaf extracts. The presence of glycosylated flavanone (eriocitrin) has been reported only in fruit extract. The antioxidant properties of different extracts were tested regarding their scavenging activities on ABTS•+ radical. Leaf and trunk bark extracts exhibited antioxidant activities, while the extracts obtained from other organs (fruits, stems, and root barks) showed low antioxidant properties.
A Rapid Determination and Quantification of Three Biologically Active Polyisoprenylated Benzophenones using Liquid Chromatography-Tandem Mass Spectrometry (MRM) Method in Five Garcinia species from Cameroon
Authors: Biloa Bernadette Messi , Ho Raimana , Marti Guillaume , Lannang Alain Meli , Wolfender Jean-Luc , Hostettmann Kurt
Published: March 2019

Following investigation of Garcinia genus, a sensitive, rapid and simple reversed-phase high performance liquid chromatography-electrospray ionization mass spectrometry method has been developed for the identification and quantification of three polyisoprenylated benzophenones, garcinol (1), isogarcinol (2) and 7- epi-clusianone (3), in the extracts of five Garcinia species from Cameroon. The separation of those compounds was achieved on a RP-18 column using a solvent system consisting of a mixture of acetonitrile-water-formic acid as a mobile phase in a gradient elution mode. The identification of the three compounds was determined on a triple quadripole mass spectrometer with ESI interface operating in the negative mode. A multiple reaction monitoring (MRM) method was developed for the quantification of these polyisoprenylated benzophenones in the extracts of the Garcinia species. The method was validated through intra- and inter-day precision, with the relative standard deviation (RSD) less than 6%, limits of detection (LOD) and limits of quantification (LOQ) <1 ng. Overall recoveries ranged from 94% to 104%, with RSDs ranging from 0.8% to 4.5%. The results indicated that the fruits of G. preussii and the roots of G. brevipedicellata are good source of garcinol (1) and isogarcinol (2) respectively.
Exploring Co-fermentation of Glucose and Galactose using Clostridium acetobutylicum and Clostridium beijerinckii for Biofuels
Authors: Tang Mi , Liu Jiawen , Ye Zhuoliang , Zhuo Shumin , Zhang Weiying , Li Xiao , Chen Dongyang
Published: March 2019

There is growing interest to produce fuels from algae, namely the third generation biofuel. Galactose and glucose are basic chemicals for many red macroalgae, but fermentation of the mixed sugars may suffer significant glucose repression using yeast. Therefore, another fermentation, acetone-butanol-ethanol (ABE) fermentation of the mixed sugars was studied using Clostridium acetobutylicum and Clostridium beijerinckii. Both strains can use either galactose or glucose, and showed an optimal pH at ~ 5.0. Co-fermentation of the mixed sugar showed simultaneous consumption of glucose and galactose, and exhibited solvent production of 4.19 and 4.57 g/L using Clostridium acetobutylicum and Clostridium beijerinckii, respectively. The fermentation can become more industrially practical if improvement in galactose consumption can be further improved in the future.
Volatile Chemical Constituents of the Chilean Bryophytes
Authors: Cuvertino-Santoni Jorge , Asakawa Yoshinori , Nour Mohammed , Montenegro Gloria
Published: March 2019

The aim of this study is to increase the phytochemical knowledge of South American bryophytes, particularly from those of the southern tip of the continent, due to the uniqueness of its poorly known bryoflora. Thirty-two specimens were analyzed using GC-MS technique. Most of the molecules found in the present bryophyte species belong to sesquiterpenes. In general, liverworts resulted to be richer in terpenoid compounds, while mosses in n-alkanes. Oplopanone, trans- chrysanthenyl acetate and 6,7-secoeudesm-7(11)-en-6-al are compounds here newly reported to the bryophytes. α-Ylangene and α-herbertenol are new to hornworts, while α-herbertenol and n-heneicosane are new to mosses.
(+)-Pathylactone A, a New Natural Nor-sesquiterpenoid from the Octocoral Paralemnalia thyrsoides
Authors: Zhang Zhi-Jun , Chen Wu-Fu , Peng Bo-Rong , Wen Zhi-Hong , Sung Ping-Jyun
Published: March 2019

A new natural marine nor-sesquiterpenoid, (+)-pathylactone A (1), along with a know nor-sesquiterpenoid, napalilactoe (2), were isolated from the octocoral Paralemnalia thyrsoides. The structure of 1 was established on the basis of spectroscopic methods and by comparison of the spectral data with those of synthetic analogues. Nor-sesquiterpenoid 1 was found to inhibit the protein experssion of pro-inflammatory inducible nitric oxide synthase (iNOS) in a murine macrophage-like cell line.
A New 28-Nor-oleanane Triterpene from Excoecaria agallocha
Authors: Mo De-Juan , Li Jun , Li Min-Yi
Published: March 2019

A new 28-nor-oleanane triterpene, 28- nor-olean-2α, 3β-dihydroxy-14,17-diene-16-one with a rare cyclohexa-2,5-dienone moiety, together with three known triterpenes, viz.β-amyrin (2), 3α- O - trans -coumaroyl-betulinic acid (3), 3-acetyl-aleuritolic acid (4), were isolated from the twigs of Excoecaria agallocha L.. Their structures were determined by extensive spectroscopic data analysis and comparison with previous literatures (known compounds).
Non-redox Lipoxygenase Inhibitors from Nauclea orientalis
Authors: Surapinit Serm , Sichaem Jirapast , Tip-pyang Santi
Published: March 2019

Eight alkaloids recently isolated from the roots of Nauclea orientalis (L.) L. were obtained to evaluate the lipoxygenase (LOX) inhibitory activity. According to the LOX inhibitory assay, the cis isomer 1 (IC50 39.2±1.1 μM) was more potent than the trans isomer 2 (IC50 52.1±1.5 μM) (P < 0.05). Compound 5 (IC5057.8±1.8 μM) was more potent than 6 (IC50 97.6±3.4 μM), 3 (IC50 112.1±2.6 μM) and 4 (inactive) (P <0.05), respectively. Alkaloid glycosides 7 and 8 were completely inactive in a screening assay. All active indole alkaloids were inactive in DPPH and 13-HPOD scavenging assays at the concentration of 100 μM. Moreover, these compounds did not exhibit the interferential effects on the Fe2+/Fe3+ redox state as indicated by the iron reduction and oxidation assays. The enzyme kinetic study revealed that 1, 2 and 6 inhibited sb-LOX-1 through the mixed inhibition with a set of inhibition constants (K i and K' i) of 9 and 22, 17 and 46, and 16 and 32 μM, respectively. Indole alkaloids 3 and 5 were the uncompetitive and noncompetitive inhibitors with the K i of 24 and 8 μM. These findings undoubtedly demonstrated that these active indole alkaloids were non-redox lipoxygenase inhibitors.
Two New Isocoumarin Derivatives from an Endophytic Fungi Pestalotiopsis coffeae Isolated from a Mangrove Fishtail Palm
Authors: Wang Zhong , Fan Peng , Xue Tong-Dan , Meng Lin-Lin , Gao Wen-Bin , Zhang Jun , Zhao You-xing , Luo Du-Qiang
Published: March 2019

Two new isocoumarin derivatives, 6,8-dihydroxy-7-methyl-1-oxo-1H-isochromene-3-carboxylic acid (1) and 6,8-dihydroxy-3-methoxy-3,7- dimethyl-isochroman-1-one (2), together with five known compounds (3-7), were isolated from the endophytic fungus Pestalotiopsis coffeae derived from the Chinese plant fishtail palm. The structures of these compounds were determined mainly by analysis of their NMR spectroscopic data. The structure of compound 2 was further confirmed by X-ray diffraction.
Antimycotic Activity of Conifer Green Needle Complex against Clinical Strains of Candida Species
Authors: Soultanov Vagif S. , Kulyashova Lidia B. , Nikitina Tamara V. , Roschin Viktor I.
Published: March 2019

Resistance of some Candida species to antimycotic agents is a public health threat, with new treatments a priority. Conifer Green Needle Complex (CGNC) is a pharmaceutical-grade complex substance from the green verdure of Pinus sylvestris and Picea abies. Characterization of the chemical composition of CGNC (gas chromatography/mass spectrometry/HPLC) showed resin acids (ca 20 %w/w), unsaponafiables, primarily terpenoid alcohols (ca 22% w/w), higher fatty acids (ca 10% w/w), bound acids (ca 11% w/w) and polyprenols (ca 2.5% w/w). Other significant components include phytosterols, carotenoids, chlorophyll derivatives, vitamin E acetate and vitamin K1. CGNC has high antioxidant activity. Preliminary results for antimycotic activity against clinical strains of Candida albicans, C. glabrata and C. krusei showed some Candida spp. were sensitive to CGNC, including fluconazole- and ketoconazole-resistant strains. Antimycotic activity of CGNC should be investigated in larger studies.
Composition of Volatile Fraction from Inflorescences and Leaves of Dendrobium moschatum (Orchidaceae)
Authors: Robustelli della Cuna Francesco Saverio , Boselli Cinzia , Papetti Adele , Mannucci Barbara , Calevo Jacopo , Tava Aldo
Published: March 2019

The volatile fractions from fresh inflorescences and leaves of Dendrobium moschatum (Buchanan-Hamilton) Swartz (Orchidaceae) were isolated by steam distillation with a yield of 0.498% and 0.041% (weight/fresh weight basis), respectively. From GC/FID and GC/MS analyses, coumarin was identified to be the most abundant constituent and quantified as 48.8% and 47.8% of the total volatiles from inflorescences and leaves, respectively. Hydrocarbons, ketones, esters, acids and aldehydes were also detected. Long chain mono unsaturated hydrocarbons were quantified in higher amount in leaves and their structures were elucidated by GC/MS of their dimethyl disulfide derivatives. These compounds together with long chain ethyl esters and methyl ketones may represent a particular feature of this plant species and can play a critical role in the interaction with pollinator insect.
Chemical Composition of the Essential Oil of Phyllanthus acidus
Authors: Pérez-Colmenares Alida , Obregón-Díaz Ysbelia , Rojas-Fermín Luis , Aparicio-Zambrano Rosa , Carmona-Arzola Juan , Usubillaga Alfredo
Published: March 2019

The essential oil from the leaves of Phyllanthus acidus (Phyllanthaceae) was obtained by hydrodistillation and its composition determined by GC and GC/MS. Twenty-one compounds were identified, representing 92.8 % of the oil. The most abundant components were t -muurolol (20.4 %), α-cadinol (14.6 %), β-cadinene (8.9 %) and α-muurolene (7.5 %).
Isolation and Structure Determination of a New Lumichrome Glycoside Isolated from a Soil Streptomyces sp. KCB16C001
Authors: Son Sangkeun , Kim Eun , Kim Jong Won , Ko Sung-Kyun , Lee Byeongsan , Lee Jung-Sook , Hong Young-Soo , Jang Jae-Hyuk , Ahn Jong Seog
Published: March 2019

Microbial studies of soil samples collected at Ochang, Korea led to the isolation of the actinobacterium Streptomyces sp. KCB16C001. Subsequent LC/MS analysis of the culture extract for dereplication purposes enabled the identification of a new metabolite ochangoside (1), whose chemical structure was determined to be 1-( α -L-rhamnosyl)-lumichrome by scale-up purification and structure elucidation procedures based mainly on NMR and MS spectroscopic data. Determination of the stereochemistry of the sugar moiety was achieved by LC/MS analysis of the sugar derivatized with L-cysteine methyl ester and o -tolyl isothiocyanate. Our results represent a rare example of natural lumichrome glycoside with a sugar unit attached at N −1.
Green Soybean Extract Ameliorates Dextran Sodium Sulfate-Induced Colitis
Authors: Yoshikawa Yuko , Murakami Takuya , Katayanagi Yuki , Yasui Kensuke , Ohgo Yasushi , Imai Shinjiro , Ohashi Norio
Published: March 2019

Green-mature soybean ( Glycine max) extract (GSE) inhibits the progression of immunoglobulin E-mediated inflammation more than the ordinary yellow-pigmented soybean extract (YSE). The inhibition of nitric oxide (NO) production by GSE in lipopolysaccharide-stimulated RAW264.7 cells has been found to be lower than that by YSE. However, this inhibitory ability became markedly pronounced by visible light irradiation. We investigated the anti-inflammatory effects of GSE and visible light-irradiated GSE (L-GSE) on dextran sodium sulfate (DSS)-induced colitis, immunoglobulin E-independent inflammation, and assessed whether light irradiation affects their anti-inflammatory properties. The severity of DSS-induced colitis was moderated by the ingestion of any of the soybean extracts, and L-GSE was the most effective in moderating the progression in colitis. GSE and L-GSE, except for YSE, inhibited the mRNA expressions of pro-inflammatory cytokines and chemokine in mice colons. All soybean extracts suppressed the mRNA expression of inducible nitric oxide synthase (iNOS), whereas GSE and L-GSE also inhibited the expression of the iNOS protein in the early phase of colitis. These results suggest that GSE is likely to suppress NO production, unlike in vitro results. Unfortunately, a significant difference in the anti-inflammation ability of GSE and L-GSE was not observed in the DSS-induced colitis mice. However, GSE and L-GSE are likely to become new candidate agents for the inhibition of inflammation and excessive NO production.
Chemical Composition of the Essential Oil from the Roots of Ferula kuhistanica Growing Wild in Tajikistan
Authors: Khalifaev Payrav D. , Sharopov Farukh S. , Safomuddin Abduahad , Numonov Sodik , Bakri Mahinur , Habasi Maidina , Aisa Haji Akber , Setzer William N.
Published: March 2019

Three samples of Ferula kuhistanica were collected from two different locations in the central part of Tajikistan. The essential oils were obtained by hydrodistillation and analyzed by GC-FID and GC-MS. A total of 77 compounds were identified representing 95.8-99.9 % of total oil compositions. The essential oils of the roots of F. kuhistanica were dominated by the monoterpene hydrocarbons α-pinene (57.7-70.6%), β-pinene (8.2-27.1%), β-phellandrene (0.1-7.2%), and myrcene (1.5-2%). To our best knowledge, this is the first report concerning the chemical composition of the essential oil obtained from the roots of F. kuhistanica.
Medical Cannabis for the Treatment of Inflammation
Authors: Namdar Dvory , Koltai Hinanit
Published: March 2019

The connection between Cannabis sativa‘s chemical compounds and their ability to treat three different inflammatory ailments including bowel diseases, (IBD, e.g., Crohn's and ulcerative colitis), neuronal diseases (IND, e.g., Parkinson and Alzheimer), and a wide range of inflammatory skin diseases (ISD, e.g., atopic dermatitis and psoriasis) is presented. We review the range of experiments conducted over the last decade using either the whole extract of cannabis or separated mono-phytocannabinoids in the attempt to decipher the lead molecules, the receptors involved, the effects on genes and proteins, and especially the therapeutic potency of cannabis-derived compounds for treating these different inflammatory diseases. Along with the specifications for its current cutting-edge potential, the drawbacks and the designated needs for additional specific information from future research are indicated.
A Review on Recent Syntheses of Amaryllidaceae Alkaloids and Isocarbostyrils (Time period mid-2016 to 2017)
Authors: van Otterlo Willem A. L. , Green Ivan R.
Published: March 2019

Alkaloids from the Amaryllidaceae have become valuable targets for synthetic organic chemists, mainly due to their wide variety of bioactivities and potential for utilization in medicinal chemistry ventures. In addition, the structural complexity of a number of these alkaloids has also been a reason for the interest in these compounds. In this review, the last 18 months of literature was perused and synthetic highlights have been presented here, with the hope to further focus attention on this interesting class of compounds and to encourage others to synthesize these compounds and their derivatives and/or analogues. The review contains examples of syntheses from most of the important alkaloid scaffold classes previously isolated from the Amaryllidaceae, namely: lycorine, crinine, galanthamine, tazettine, montanine, phenanthridone, phenanthridine, plicamine, mesembrine and some minor scaffolds (like gracilamine).
Oxidation of 3β-Acetoxy-21β-acetyl-20β,28-epoxy-18α,19βH-ursane into Novel gem-Chloronitro- and 1,2,4,5-tetraoxane derivatives
Authors: Yamansarov Emil Yu. , Khusnutdinova El'mira F. , Lobov Alexander N. , Kazakova Oxana B. , Suponitsky Kirill Yu.
Published: March 2019

The first oxidative transformations of 3β-acetoxy-21β-acetyl-20β,28-epoxy-18α,19β H-ursane at the 21β-acetyl reaction center were performed. Ursane-type 1,2,4,5-tetraoxanes were synthesized by acid-catalyzed peroxy-condensation with cyclohexanone bis-hydroperoxide, and oxidation of the C(28)H2 group to C(28)=O was also observed. The ursane-bearing exogenous oximino-moiety was formed as a mixture of syn- and anti-isomers (1:1). Oxidative chlorination of oxime via NaCl/oxone led to the diastereomeric mixture of novel ( R) and ( S)- gem-chloronitro-derivatives (1:1). The stereochemistry of oximino- and gem-chloronitro- derivatives was established through X-ray analysis and NMR spectroscopy.
A New Saponin with Anti-HIV-1 Protease Activity from Acacia pennata
Authors: Nguyen Van-Dung , Nguyen Hong-Loan Thi , Do Linh-Chi , Van Tuan Vu , Thuong Phuong Thien , Phan Tuan-Nghia
Published: March 2019

We investigated the phytochemicals from an ethanol extract of Acacia pennata (L.) Willd stems, a Vietnam medicinal plant, which led to the isolation of a new saponin termed 21β- O-[(2 E)-6-hydroxyl-2,6-dimethyl-2,7-octadienoyl] pitheduloside G (1), as well as pitheduloside G (2), a known saponin. The structures of compounds 1 and 2 were elucidated via spectroscopy and compared with those reported in the literature. The isolates (1 and 2) were tested for their inhibitory effects on human immunodeficiency virus type 1 (HIV-1) protease (PR). We found that the new compound, 21β- O-[(2 E)-6-hydroxyl-2,6-dimethyl-2,7-octadienoyl] pitheduloside G (1), possessed potent anti-HIV-1 PR activity, with a half-maximum inhibitory concentration (IC50) value of 2.0 ± 0.2 μM. In contrast, pitheduloside G (2) exhibited much less inhibition, with an IC50 value of 18 ± 0.5 μM. Both compounds were nontoxic in human embryonic kidney 293T cells at concentrations effective against HIV-1 PR. This is the first report regarding the isolation of an anti-HIV-1 PR compound (1) from an Acacia plant species.
In vitro Shoot Cultures of Pterospartum tridentatum as an Alternative to Wild Plants as a Source of Bioactive Compounds
Authors: Gonçalves José Carlos , Coelho Maria Teresa , da Graça Diogo Maria , Alves Vitor D. , Bronze Maria Rosário , Coimbra Manuel António , Martins Vitor Manuel , Moldão-Martins Margarida
Published: March 2019

The aim of this study was to evaluate the composition of aqueous extracts of in vitro shoot cultures and wild plants of Pterospartum tridentatum in order to promote the use of this plant material as a possible source of bioactive compounds. The extraction yield from wild plants compared with in vitro shoot cultures was lower. The total phenolic contents of in vitro shoots were significantly lower compared with those of wild plants. The phenolic profiles of in vitro shoots were very similar to those of wild plants, regardless of the source. However, taxifolin-6- C-glucoside, as well as rutin and isoquercitrin, were not present in extracts of in vitro shoots. An interesting result was the higher molar percentages of rhamnose and uronic acids detected in in vitro shoots compared with the wild plants, which can make the in vitro plant material very useful for obtaining these compounds.
Resveratrol Oligosaccharide Induces mRNA Expression for SIRT
Authors: Hamada Hiroki , Shimoda Kei , Saitoh Yasukazu , Doi Shouta , Fujitaka Yuya , Ono Tsubasa , Hamada Hatsuyuki , Araki Minami
Published: March 2019

Piceid (resveratrol 3- O-β-D-glucoside) was glycosylated by cyclodextrin glucanotransferase to give oligosaccharides of resveratrol. Resveratrol oligosaccharides induced mRNA expression of SIRT1–6.
Molecular Insights of Hyaluronic Acid as Potential Source of Polymer-Drug Conjugate in the Target-Mediated Treatment of Cancer
Authors: Shanmugam Gnanendra , Varadharajan Rajesh Salem , Prabakar Desika , Mohammed Syed , Renganathan Sathiyapriya , Erminio Murano , Aroulmoji Vincent
Published: March 2019

The naturally occurring polysaccharide hyaluronic acid (HA) is a major component of the extracellular matrix and is found over expressed in many cancer cells. Hyaluronic acid is reported to be a potential carrier for drug delivery with the dual advantage of accumulation at the tumor site and receptor-mediated uptake. The use of drugs conjugated with macromolecules was shown to improve the drug pharmacokinetic profile. The various biological potentials such as biodegradability, biocompatibility, non-toxicity, hydrophilicity and non-immunogenicity, together with the availability of various chemical groups that allow the conjugation of drugs, put forward HA as a potential choice for the development of drug conjugates. In this context, the present study is focused to provide, through docking studies, insights on the activity of cancer drugs such as methotrexate, 3′,5′-dichloromethotrexate and ornithine-methotrexate and their activity against the receptor caspase-1, which is a well-established drug target in the treatment of cancer. The docking study envisages that the usage of methotrexate properly conjugated to the natural polysaccharide HA might serve as a potential drug to effectively treat some cancer diseases.
Sesquiterpene Lactones and Phenols from Polyfollicles of Magnolia vovidessi and their Antimicrobial Activity
Authors: Ramírez-Reyes Thalía , Monribot-Villanueva Juan L. , Jiménez-Martínez Oscar D. , Aguilar-Colorado Ángel S. , Bonilla-Landa Israel , Flores-Estévez Norma , Luna-Rodríguez Mauricio , Guerrero-Analco José A.
Published: March 2019

Bioassay-guided fractionation of an active crude extract (EtOAc) of polyfollicles of Magnolia vovidessi, an endemic medicinal plant of the cloud forest of Mexico, led to the isolation and identification of shizukolidol (1), an eudesmane-type sesquiterpenoid lactone that showed antibacterial activity against the economically important phytopathogenic bacterium Chryseobacterium sp. (MIC= 400 μg/mL). In addition, 4α,8β-dihydroxy-5α(H)-eudesm-7(11)-en-8,12-olide 8 (2), rutin, scopoline and scopoletine were also isolated as were mexicanin, parthenolide, costunolide, astragalin, quercetin, hesperidin, p-coumaric acid, chlorogenic acid, vanillin, vanillic acid, 4-hydroxybenzoic acid, protocatechuic acid and shikimic acid identified by a dereplication-like procedure using LC-ESI-MS/MS. Rutin displayed mild anti-oomicite activity against phytopathogen Phytophthora cinnamomi.
Protective Effects of Compounds in Bombax ceiba flower on Benzo[a]pyrene-Induced Cytotoxicity
Authors: Nakashima Souichi , Oda Yoshimi , Ogawa Yuki , Nakamura Seikou , Uno Miyako , Kishimoto Mariko , Yoshikawa Masayuki , Matsuda Hisashi
Published: March 2019

The methanolic extract of the flower of Bombax ceiba was found to show protective effects on cytotoxicity induced by benzo[a]pyrene (BaP) in HT1080 cells. We therefore tried to examine and estimate the active constituents. We isolated 16 compounds from the extract, including four butyrolactones and two ascorbic acid derivatives, as well as mangiferin. Among the isolated compounds, a butyrolactone derivative, (-)-loliolide, and two flavonoids, kaempferol 3- O-β-D-glucopyranoside and quercetin 3- O-β-D-glucopyranoside, protected the cells against the BaP-induced cytotoxicity. Quercetin, the aglycone of one of the active constituents, showed a weaker effect than its glycoside. This is the first report of the protective effects of the methanolic extract of B. ceiba and its constituents on BaP-induced cytotoxicity.
Bentonite as a Refining Agent in Waste Cooking Oils Recycling: Flash Point, Density and Color Evaluation
Authors: Mannu Alberto , Vlahopoulou Gina , Sireus Veronica , Petretto Giacomo Luigi , Mulas Gabriele , Garroni Sebastiano
Published: March 2019

Clarification of waste recycled cooking oil (WCO) is very important in order to refine the intermediate regenerated base resulting from the previous steps. Bentonite has been historically employed as a filling material for oil refining filters due to its easy availability and its cheap price. In the present communication our early results from the filtration of degummed WCO through a pad of bentonite are presented. In particular, the variation of density, flash point and color have been monitored prior and after the filtration process and compared with samples of non-filtered WCO. An early classification of the bentonite employed has been conducted on the basis of FT-IR and XRD measurements.
Circadian Rhythm, and Antimicrobial and Anticholinesterase Activities of Essential Oils from Vitex gardneriana
Authors: Pereira Evaristo Jose Pires , do Vale Jean Parcelli Costa , da Silva Priscila Teixeira , Lima Joyce dos Reis , Alves Daniela Ribeiro , Costa Patricia Silva , Rodrigues Tigressa Helena Soares , de Menezes Jane Eire Silva Alencar , de Morais Selene Maia , Bandeira Paulo Nogueira , Fontenelle Raquel O.S. , Santos Hélcio Silva
Published: March 2019

Vitex gardneriana, popularly known as “jaramataia”, is a shrub commonly found in the caatinga biome located in northeast Brazil. In folk medicine, its leaves have been used as analgesic and anti-inflammatory agents. Here we describe, for the first time, the chemical composition of the leaf essential oils extracted at 8.00, 12.00 and 17.00 h from V. gardneriana and report on their circadian rhythm, and antimicrobial and anticholinesterase activities. The essential oils’ antifungal activity was evaluated by a broth microdilution method using strains of dermatophytes, fungi and yeasts. The modulatory activity assays were performed by the checkerboard technique using ketoconazole as a standard drug, and acetylcholinesterase inhibitory activity was performed using Ellman's colorimetric method and compared with a reference acetycholinesterase inhibitor (physostigmine). The essential oils extracted from the leaves were analyzed by GC/MS and GC/FID. Twenty-five constituents (94.7%) were identified in the 8 o'clock oil, these being 2 monoterpenes (0.4%) and 23 sesquiterpenes (94.3%). For the essential oil extracted at 12 o'clock, 26 constituents (91.8%) were identified, of which 2 were monoterpenes (0.3%) and 24 sesquiterpenes (91.5%). For the essential oil extracted at 17.00 h, 32 constituents (91.4%) were identified, of which 5 were monoterpenes (3.4%) and 27 sesquiterpenes (88%). The main constituents of the 8.00, 12.00 and 17.00 h essential oils were the sesquiterpenes cis-calamenene (27.9, 24.5 and 25.8%), 6,9-guaiadiene (21.8, 11.2 and 18.4%) and caryophyllene oxide (16.7, 26.3 and 13.8%), respectively. The essential oils showed activity against strains of Trichophyton rubrum.
Pteridaceae Fragrant Resource and Bioactive Potential: A Mini-review of Aroma Compounds
Authors: Fons Françoise , Froissard Didier , Morel Sylvie , Bessière Jean-Marie , Buatois Bruno , Sol Vincent , Fruchier Alain , Rapior Sylvie
Published: March 2019

Seven ferns of Pteridaceae, grown in a botanical garden or wild, harvested in France were investigated for their Volatile Organic Compounds (VOC) profile using GC-MS: Adiantum pedatum L., Adiantum peruvianum Klotzsch, Anogramma leptophylla (L.) Link, Cheilanthes maderensis Lowe, Cryptogramma crispa (L.) R. Br., Pteris cretica L. and Pteris vittata L. Fifty-three VOC biosynthesized from lipidic, shikimic, terpenic and carotenoid pathways were identified. The two Adiantum species show different VOC composition. The main linalool (10.8%) in A. pedatum has several biological activities of great interest. This Maidenhair fern contains the highest proportion (57.9%) of isoprenoid flavor precursors, i.e., ionone derivatives with various scent notes. The two major odorant unsaturated hexenoic acids derivatives of A. peruvianum are used as flavouring agents. Anogramma leptophylla concentrates 6-methoxymellein (71.5%), a bitter phytoallexin which contributes to stress or pathogen resistance. Cheilanthes maderensis produces mainly coumarin (89%) and vanillin (3.5%) with a low odor detection threshold, both used in perfumery and cosmetic industry or as flavouring agent and drug additives. Cryptogramma crispa accumulates a broad-spectrum of carotenoid derivatives (52.1%) and three major shikimic derivatives: the spicy 4-vinylguaiacol (flavouring agent), the floral phenylethanal and benzyl alcohol with floral, balsamic scent. Pteris cretica accumulates mostly furan derivatives, i.e., 5-hydroxymethylfurfural (33.2%) and 3-hydroxy-2,3-dihydromaltol (18.3%) used as food and beverage additives with caramel or roasty flavour and also found in fortified wines, toasty or heat-treated foods. Pteris vittata produces predominantly shikimic derivatives applied in perfumery and food industries as benzaldehyde (26%, with almond scent), benzyl alcohol (22%, floral fruity balsamic scent), nonanal (19.8% cucumber note) and phenylethanal (11%; floral note). Pteridaceae resources are of great interest as a reservoir of odorous and bioactive compounds.
Synthesis and Cytotoxicity of 28-N-Propargylaminoalkylated 2,3-Indolotriterpenic acids
Authors: Khusnutdinova Elmira F. , Petrova Anastasiya V. , Kukovinets Olga S. , Kazakova Oxana B.
Published: March 2019

A new series of propargylaminoalkyl derivatives with N-methylpiperazine and morpholine fragments was obtained by modification of the carboxyl group of [3,2b]-indolotriterpenic acids ( N-propargylation, Cu(I) catalyzed Mannich reaction). Cytotoxicity assays demonstrated that oleanane-type conjugate with N-methylpiperazine exhibited high antitumor activity against leukemia cell line SR and non-small cell lung cancer cell line NCI-H460.
Atropisomerism of a Podophyllotoxin Derivative: Experimental and Computational Study
Authors: Zhou Shi-Wen , Jiang Fei , Yu Yang , Huang Xiu-Yong , Wang Yong-Heng , Luo Shi-Lin
Published: March 2019

Diphyllin-7′- O-β-D-glucoside, a podophyllotoxin derivative, was isolated from the roots of Dysosma versipellis. The 1H and 13C NMR spectra acquired at 300 K exhibited doubling of signals, suggesting the existence of two rotamers in solution. Variable-temperature 1H NMR experiments indicated a dynamic exchange process between the two rotamers. DFT calculations verified nearly equal energies for the two rotamers about the single bond C7′-O7.
Pestalotilide A, a New Cytotoxic Diphenyl Ether Derivative from Pestalotiposis guepinii
Authors: Xiao Jian , Zhong Wan-Tong , Lin Li-Bin , Zhao Xiang , Shi Wei , Hu Jia-Yao , Duan Dong-Zhu , Wang Le , Wang Xiao-Ling
Published: March 2019

A new diphenyl ether derivative, named pestalotilide A (1), along with four known compounds (2-5) have been isolated from the organic extracts of an endophytic fungus Pestalotiposis guepinii. Their structures were elucidated on the basis of HR-ESI-MS, 1D and 2D NMR spectroscopic data analyses. These isolates were evaluated for cytotoxicity against three cancer cell lines: Hela, HCT116 and A549; pestalotilide A exhibited weak in vitro anti-proliferative activities against the tested cell lines, with IC50 values of 23.8, 18.4 and 35.2 μM, respectively.
Chemical Composition and Antibacterial Activity of Bornean Medicinal Ginger Alpinia aquatica
Authors: Kamada Takashi , Ng Shean-Yeaw , Phan Chin-Soon , Vairappan Charles S.
Published: March 2019

One new phenylbutenoid, (3 Z)-2′,4′,5′-trimethoxyphenylbutadiene (1) along with five known metabolites were isolated from aquatic galangal ( Alpinia aquatica Rosc.) and their chemotaxonomy importance in five populations of A. aquatica collected from Kota Kinabalu, Ranau and Kota Belut in Sabah, Malaysia. The antibacterial potential as well as the chemosystematics importance of this discovery is discussed.
Sulforaphane Suppresses Sepsis-Mediated Renal Functions in Cecal Ligation and Puncture Mouse Model
Authors: Lee In-Chul , Bae Jong-Sup
Published: March 2019

Sulforaphane (SFN), a natural isothiocyanate present in cruciferous vegetables such as broccoli and cabbage, is effective in preventing carcinogenesis, diabetes, and inflammatory responses. This study was initiated to determine whether SFN could modulate renal functional damage in a mouse model of sepsis and to elucidate the underlying mechanisms. The potential of SFN treatment to reduce renal damage induced by cecal ligation and puncture (CLP) surgery in mice was measured by assessment of serum creatinine, blood urea nitrogen (BUN), lipid peroxidation, total glutathione, glutathione peroxidase activity, catalase activity, and superoxide dismutase activity. Treatment with SFN resulted in elevated plasma levels of BUN and creatinine, and of protein in urine in mice with CLP-induced renal damage. SFN treatment also reduced the plasma levels of interleukin-6 (IL-6) and tumor necrosis factor-α (TNF-α),▢increased lipid peroxidation, and markedly enhanced the antioxidant defense system by restoring the levels of superoxide dismutase, glutathione peroxidase, and catalase in kidney tissues. The present results suggested that SFN protects mice against sepsis-triggered renal injury.
Chemical Profile of Leaf Essential Oil of Cinnamomum walaiwarense and Comparison of its Antioxidant and Hypoglycemic Activities with the Major Constituent Benzyl Benzoate
Authors: Sriramavaratharajan Venkatraman , Murugan Ramar
Published: March 2019

Leaf essential oils of an unexplored wild cinnamon, Cinnamomum walaiwarense Kosterm. collected from seven different locations in the southern Western Ghats, India were characterized by GC-FID and GC-MS analyses. Benzyl benzoate was the principal constituent of the leaf essential oil present at a concentration from 65 to 89.8%. Another major constituent was phenylethyl benzoate. The results on antioxidant (ABTS and DPPH radical scavenging) and hypoglycemic (α-amylase and α-glucosidase inhibitory) activities show that the leaf essential oils exhibited better activities than benzyl benzoate. The very least antioxidant and inhibitory activities of benzyl benzoate show that these activities of the leaf essential oils were due to the synergistic action of minor constituents. The rich content of benzyl benzoate in the leaf essential oil makes C. walaiwarense a potential natural source of this compound. As benzyl benzoate is an excellent scabicide and pediculicide, the essential oil may be further investigated for industrial and other medicinal applications.
Cycloartane Triterpenoids with Anti-melanin Deposition Activity
Authors: Nugroho Alfarius Eko , Matsumoto Misaki , Sotozono Yayoi , Kaneda Toshio , Hadi A. Hamid A. , Morita Hiroshi
Published: March 2019

Bioactivity guided separation of the extract of Malaysian Garcinia sp. resulted in the isolation of 23-acetoxy-mangiferonic acid (1) and the absolute configuration of C-23 was elucidated to be R by the advanced Mosher's method. The anti-melanin deposition activity of 1 was caused by the down regulation of tyrosinase gene expression.