bluuebunny/crossref_metadata_2025 huggingface dataset:
Fruits of Rosa brunonii – A Source of Antioxidant Phenolic Compounds
Authors: Ishaque Muhammad , BiBi Yamin , Valant–Vetschera Karin M. , Schinnerl Johann , Bacher Markus
Published: March 2019

Phytochemical examination of matured fruits of Rosa brunonii collected in Northern Pakistan led to the isolation of three flavonol glycosides quercetin-3- O-rhamnoside (1), and the kaempferol glycosides astragalin (2) and tiliroside (3). Their structures were elucidated by 1D– and 2D–NMR spectroscopy and mass spectrometry. Radical scavenging activities of the crude extract and isolated compounds were assessed by a DPPH assay. The results show strong antioxidative activities of tiliroside (3) and lower activities of astragalin (2) and quercetin-3- O-rhamnoside (1). These data confirm previous reports and underline the biological activities of flavonol glycosides.
Chemical Constituents of Sinningia hatschbachii
Authors: Amorim Magali S. , Serain Alessandra F. , Salvador Marcos José , Stefanello Maria Élida A.
Published: March 2019

A new naphthoquinone, 6-hydroxy-7-methoxy-2- O-methylduniol (1), was isolated from the tubers of Sinningia hatschbachii Chautems (Gesneriaceae), together with 10 known compounds: 7-hydroxy-α-dunnione, 7-hydroxy-6-methoxy-α-dunnione, 2,4,4’,6-tetramethoxydihydrochalcone, 4’-hydroxy-2,4,6-trimethoxydihydrochalcone, 4’,2-dihydroxy-4,6-dimethoxydihydrochalcone, methyl 1-hydroxy-4-methoxy-2-naphthoate, methyl 1,4-dimethoxy-2-naphthoate, methyl 4-hydroxybenzoate, calceolarioside B, and conandroside. All compounds were identified by spectroscopic techniques, and comparison with literature. Extracts in hexane, CH2Cl2, EtOAc and EtOH were evaluated for antimicrobial activity against Staphylococcus aureus, S. epidermidis, Escherichia coli, Pseudomonas aeruginosa, Candida albicans, C. dubliniensis, C. glabrata, and C. parapsilosis. All extracts were inactive.
Rumphellolide J, an Ester of 4β,8β-Epoxycaryophyllan-5-ol and Rumphellaoic acid A, from the Gorgonian Rumphella antipathies
Authors: Lin Chi-Cheng , Chung Hsu-Ming , Su Yin-Di , Peng Bo-Rong , Wang Wei-Hsien , Hwang Tsong-Long , Wu Yang-Chang , Sung Ping-Jyun
Published: March 2019

Rumphellolide J (1), a novel sesquiterpenoid derivative, isolated from the gorgonian coral Rumphella antipathies, was determined to be an ester of 4β,8β-epoxycaryophyllan-5-ol and rumphellaoic acid by detailed spectroscopic analysis.
Xenocyloin Derivatives from Liquid Cultures of Xenorhabdus bovienii SN52
Authors: Yu Feng , Tian Xiaomei , Sun Ying , Bi Yuhui , Yu Zhiguo , Qin Li
Published: March 2019

Members of genus Xenorhabdus are symbiotically associated with entomopathogenic nematodes of genus Steinernema. Herein, we describe the isolation and purification of four novel metabolites, xenocyloins G-J (1–4), from liquid cultures of Xenorhabdus bovienii SN52 by extensive column chromatography and semi-preparative HPLC. Chemical structures of the xenocyloin derivatives were determined based on comprehensive NMR spectra and HR-ESI-MS analyses. All compounds exhibited significant collagen-induced anti-platelet aggregation activities, among which xenocyloin H (2) exhibited the strongest activity with an inhibition rate of 96.0 ± 0.1% at a concentration of 50 μM. The xenocyloin G (1) and H (2) exhibited anti-platelet activities with IC50 values which were 31.7 ± 4.4 μM and 27.5 ± 3.5 μM respectively; whilst under similar conditions the IC50 value for aspirin was 289.5 ± 15.7 μM, nearly ten times less than 1 and 2.
Microwave-assisted Acid Hydrolysis to Produce Vitexin from Crataegus pinnatifida Leaves and its Angiogenic Activity
Authors: Luo Meng , Ruan Xin , Hu Jiao-Yang , Yang Xuan , Xing Wen-Miao , Fu Yu-Jie , Mu Fan-Song
Published: March 2019

In this study, microwave-assisted acid hydrolysis (MAAH) to obtain vitexin (VIT) from Crataegus pinnatifida leaves was optimized. The single factor experiment was applied to optimize the operating parameters of MAAH. The 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay and ferric reducing ability of plasma (FRAP) were performed to evaluate the antioxidant activity of extract. The results showed that the optimum parameters of dealing with 1 g sample were 2.0 M hydrochloric acid concentration, 40 min microwave irradiation time, 1:10 solid–liquid ratio, 50% ethanol concentration, 70°C microwave extraction temperature and 600 W microwave power. The yields of VIT were 2.62 mg/g under the optimum conditions. The C. pinnatifida extracted by MAAH exhibited more antioxidant activity than extracted by microwave-assisted extraction (MAE). The number of vessels in chick chorioallantoic membrane indicated that C. pinnatifida leaves could promote angiogenesis. These findings suggested that MAAH provides an efficient technique to produce VIT.
Analysis of the Configuration of an Isolated Double Bond in Some Lipids by Selective Homonuclear Decoupling
Authors: Santalova Elena A. , Denisenko Vladimir A.
Published: March 2019

The purpose of this report is to demonstrate that selective homonuclear decoupling can be used as an alternative for 13C NMR method for identifying configuration of an isolated (mid-chain) double bond in some lipids. Using homodecoupling of allylic protons, the coupling constants Jcis or Jtrans between the olefinic protons of some fatty acid methyl esters and related compounds with ( n–7) and ( n–9) terminal structures were evaluated. The optimal conditions of the homodecoupling experiments on these compounds were examined. Empirical rules were proposed to predict the results of homodecoupling experiments on lipid with an isolated double bond.
Anti-HIV 1 Activity of Xanthones from the Bark of Mammea harmandii
Authors: Liangsakul Ponsiri , Kuhakarn Chutima , Hongthong Sakchai , Jariyawat Surawat , Suksen Kanoknetr , Akkarawongsapat Radeekorn , Limthongkul Jitra , Napaswad Chanita , Reutrakul Vichai
Published: March 2019

A new xanthone glycoside 1 together with four known flavonoid derivatives, astilbin (2), neoastilbin (3), isoastilbin (4), and epicatechin (5) were isolated from the ethyl acetate fraction partitioned from the methanol extract of the bark of Mammea harmandii. The chemical structures of all isolated compounds were established on the basis of their spectroscopic data. Compound 1 exhibited selective significant inhibitory activity in the anti-syncytium assay with an EC50 value of 11.44 μM (SI = 14.03) while it was found inactive against HIV 1 reverse transcriptase as well as cytotoxic activity.
Ferulic Acid, Methyl Ferulate, and Ferulic Acid Glucopyranosyl Ester Isolated from Cultured Cells of Phytolacca americana
Authors: Shimoda Kei , Kubota Naoji , Hamada Hiroki , Doi Shouta , Ishihara Kohji , Hamada Hatsuyuki , Fujitaka Yuya , Ono Tsubasa , Araki Minami
Published: March 2019

Production of secondary metabolites in cultured plant cells of Phytolacca americana was investigated. Three compounds, i.e., ferulic acid, methyl ferulate, and ferulic acid glucopyranosyl ester, were isolated from cultured P. americana cells.
Phyto-metabolites; An Impregnable Shield against Plant Viruses
Authors: Islam Waqar , Adnan Muhammad , Tayyab Muhammad , Hussain Mubasher , Islam Saif Ul
Published: March 2019

Worldwide, economically important crops are under continuous threat from plant viruses as they reproduce within the host and spread via various biological and non biological means. The problem can be minimized via application of integrated management approaches involving utilization of resistant genotypes and reducing the insect vector population. But such strategies are rarely applied in developing countries and farmers prefer to use chemicals against all type of diseases. But increasing use of pesticides is a leading cause of disaster to our ecosystem so alternative means such as phyto-metabolites should be explored for eco friendly management of plant viruses. So here we have reviewed about different phyto-metabolites that can be effectively and potentially used against various plant virus diseases. We further explained about the various primary and secondary metabolites such as alkaloids, essential oils, flavonoids, polysaccharides and proteins. The review highlights the recent advances in the field of phyto-metabolites utilization against plant viruses and sums up via hoping through prospects that future drugs will be safer for human beings and our ecosystem.
A New Diepoxy abietaneolide from Suregada multiflora
Authors: Gondal Humaira Yasmeen , Nisar Muhammad , Choudhary M. Iqbal
Published: March 2019

A new (1) and two known (2-3) diterpene lactones belonging to a rare class of diepoxy abietaneolide, were isolated from the cytotoxic extract of Suregada multiflora. New compound 1 is characterized as 3β-hydroxy-8,14β:11,12α-diepoxy-13(15)-abietane-16,12-olide, on the basis of extensive spectral studies. This is the first report describing 2D NMR studies of this unique class of diepoxy abietaneolide.
Two New Compounds from Medicinal Insect Blaps japanensis and Their Biological Evaluation
Authors: Zheng Tao , Ming Yan-Yong , Tu Zheng-Chao , Xu Fu Rong , Cheng Yong-Xian
Published: March 2019

Blaps japanensis is a medicinal insect used for the treatment of a variety of disorders in Yi-nationality of Yunnan province, China. In the present study, two new compounds, named pipajiains F and G (1 and 2), along with four known compounds, 3-indolealdehyde (3), L-tryptophan (4), ginsenine (5), and anoectochine (6) were isolated from B. japanensis. Their structures were identified on the basis of spectroscopic methods. Compound 1 is a phenolic compound bearing a pyridine-1-ium-1carboxylate motif in the structure which made 1 an unusual architecture. Compounds 2 is an indole alkaloid derivative. Biological activities of all these compounds towards COX-2, ROCK1/2, and JAK3 kinases were evaluated.
Pseudoguaianolides: Recent Advances in Synthesis and Applications
Authors: Barbero Margherita , Prandi Cristina
Published: March 2019

Pseudoguaianolides belong to the class of sesquiterpene lactones and are characterized by the lactone ring cis or trans-anellated (in 6,7- or 7,8- position) to fused seven- and five-membered rings; they differ from guaianolides for the position of the methyl group in 5. The unusual tricyclic fused core 5/7/5 was a challenge and inspired new synthetic methodologies to install substituents with proper stereochemistry. Despite their potential of application in different fields, their exploitation is so far very limited. Because of this, with this review we wanted to give perspectives in terms of availability and resupply of the most active compounds of the class.
Natural Phenyldihydroisocoumarins: Sources, Chemistry and Bioactivity
Authors: Çiçek Serhat S. , Vitalini Sara , Zidorn Christian
Published: March 2019

The present review gives an overview about naturally occurring phenyldihydroisocoumarins, their sources, and bioactivities. In total, 54 compounds are covered, including eight substances which are in fact alkaloids or protoalkaloids. These nitrogen containing compounds were exclusively found in the Papaveraceae family. The remaining 46 compounds have been reported from twelve different source families, ranging from mosses to angiosperms. Six of the nitrogen free compounds feature additional rings, while 40 are simple phenyldihydroisocoumarins with substituents in all possible positions, except 3, 2’, and 6’. Common substituents of these simple phenyldihydroisocoumarins are hydroxy groups, methoxy groups, and glucosyloxy groups; on the other hand, acuminosyloxy and rutinosyloxy groups have so far been found only in one and two naturally occurring phenyldihydroisocoumarins, respectively. Though a number of bioactivities have been proven for phenyldihydroisocoumarins, ranging from anticancer and antidiabetic to antimicrobial and anti-inflammatory activities, so far only one taxon, Hydrangea macrophylla var. thunbergii, is widely used. Moreover, the usage of this taxon is mainly due to the sweet taste properties of the contained phenyldihydroisocoumarin phyllodulcin and less based on the alleged health-promoting effects of its constituents.
Synthesis of Analogues of (+)-Gomphoside, a Potent HIF-1 Inhibitor and Cardenolide
Authors: Cuny Eckehard
Published: March 2019

The milkweed bush Gomphocarpus fruticosus R.Br. found in Australia contains the steroidal glycoside (+)-gomphoside, its derivatives (-)-3'-dehydrogomphoside and (+)-3'- epi-gomphoside, as well as other glycoside compounds. The key structural features of these unique herbal agents are bislinked steroid to sugar linkages. (+)-Gomphoside is an extremely potent cardenolide and highly effective Hypoxia-Inducible Factor (HIF)-1 inhibitor. In addition, (+)-gomphoside exhibits strong cytotoxicity on human breast cancer cell lines.

The syntheses of (+)-gomphoside analogues with modified steroidal D rings are described here. The syntheses started with glycosylation of (+)-(2α,3β,5α)-2,3-cholestanediol with benzoylated 2-keto sugar bromides, promoted by silver carbonate. Two regioisomeric glycosides with bent up and bent down ring anellation geometry were obtained, because of the two hydroxyl groups in the diol. Modification of the sugar ring of these glycosides by base-induced elimination of benzoic acid yielded (-)-3'-dehydrogomphoside analogues. The analogues of (+)-gomphoside and (+)-3'- epi-gomphoside were then obtained by stereoselective reduction of the 3'-carbonyl function. Compared to natural (+)-gomphoside, these analogues have the following unique structural features: a steroidal D ring with C8H17-alkyl chain instead of an exocyclic butenolide moiety, a different configuration at bridgehead carbon-14, and lack of a hydroxyl group at this position. The resulting altered chemical properties make them interesting structures for pharmacological evaluation and they are potentially suitable candidates for the development of new inhibitors in cancer therapy.
On the Structure of (R)-2-Methylheptyl Isonicotinate: Evidence for the Structural Solution from Total Synthesis
Authors: Ponnapalli Mangala Gowri , Gundoju Narayana Rao , Theerthala Harikiran , Bokam Ramesh , Yalavarthi Nageswara Rao
Published: March 2019

The controversial molecular identification of ( R)-2-methylheptyl isonicotinate (1) has been settled. Despite its significance as a potent anti-microbial agent against several clinically relevant pathogens, the structure of natural product is uncertain so far due to controversial reports. Its structure has been resolved as bis (2-ethylhexyl) phthalate (2) by total syntheses of chain isomers. In addition, we have also revised bis (2-methylheptyl) phthalate (3) as (2) in some reports.
Polyisoprenylated Acylphloroglucinols from Garcinia nervosa
Authors: Nugroho Alfarius Eko , Nakamura Hitomi , Inoue Daisuke , Hirasawa Yusuke , Wong Chin Piow , Kaneda Toshio , Hadi A. Hamid A. , Morita Hiroshi
Published: March 2019

Two new polyisoprenylated acylphloroglucinols, 7- epi-isoxanthochymol and 7- epi-cycloxanthochymol (1 – 2), were isolated from the barks of Garcinia nervosa together with their 7-epimers isoxanthochymol (3) and cycloxanthochymol (4). Their structures were determined on the basis of NMR spectroscopic data. The cytotoxic activity of the isolated compounds against HL-60, MCF-7 (human breast adenocarcinoma), A549 (human lung adenocarcinoma) and HepG2 (human hepatocellular carcinoma) cells were evaluated, and all compounds showed cytotoxic activity against all cell lines.
Sesquiterpene Lactones and Phenolics from Roots of Leontodon hispidus subsp. hispidus
Authors: Michalska Klaudia , Pieron Katarzyna , Stojakowska Anna
Published: March 2019

The phytochemical investigation on roots of Leontodon hispidus L. subsp. hispidus, led to the isolation of nine sesquiterpene lactones including two eudesmanolides of santamarine type and three lactucin-like guaianolides together with four known phenolic compounds. The eudesmanolides – santamarine and 11 β,13-dihydrosantamarine, guaianolides – matricarin, deacetylmatricarin and deacetylmatricarin 8- O- β-glucopyranoside, and phenolics – syringaldehyde, 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone, syringin and dihydroconiferin were found for the first time in Leontodon.
Ginsenoside Rg1 Exhibits Anti-asthmatic Activity in an Aspergillus Protease-Induced Asthma Model in Mice
Authors: Lim Chiyeon , Lim Sehyun , Lee Byoungho , Cho Suin
Published: March 2019

Asthma is one of the most common chronic airway diseases and is characterized by symptoms, such as, wheezing and coughing. Its prevalence in Korea is gradually increasing among children and adults, especially among those older than 60 years. In this study, we investigated the effects of ginsenoside Rg1 (Rg1), one of the major constituents of Panax ginseng Meyer on ovalbumin (OVA) plus Aspergillus protease ( A. protease) allergen-induced asthmatic mice. Mice were orally administered Rg1 for 10 days from 8 days after OVA + A. protease sensitization and intranasally administered booster doses of OVA + A. protease for 4 days from 14 days after sensitization. The effects of Rg1 administration on airway hyperresponsiveness (AHR), immune cell distributions in bronchoalveolar lavage fluid (BALF), and serum level of immunoglobulin E (IgE) were investigated at 18 days after sensitization. Histopathological changes in hematoxylin and eosin (H&E)-stained lung sections were also examined. Treatment of OVA + A. protease-sensitized/challenged asthmatic mice with Rg1 significantly decreased total eosinophil counts in BALF as compared with those of phosphate-buffered saline (PBS)-treated sensitized/challenged controls, and significantly decreased methacholine-induced AHR. Furthermore, IgE serum levels were significantly lower in Rg1 administered OVA + A. protease-sensitized asthmatic mice than in PBS-treated sensitized/challenged controls. The study shows Rg1 protects against A. protease allergen-induced asthma in mice.
A Phytochemical and Pharmacological Review on Cynomorium songaricum as Functional and Medicinal Food
Authors: Cui Jin-Long , Gong Yi , Xue Xiao-Zan , Zhang Yan-Yan , Wang Meng-Liang , Wang Jun-Hong
Published: March 2019

Cynomorium songaricum Rupr. (CSR) has a long history of being widely used as a functional food and medicine by different ethnic groups worldwide; CSR is used to treat impotence and premature ejaculation and traditionally used as natural source of tonic food. Numerous bioactive compounds linked with human health were recently identified. In this work, all available information on CSR were retrieved from NCBI PubMed and CNKI database, and the recent findings about the compositions and functions of CSR were summarized. At least 76 bioactive compounds, including flavonoids, terpenoids, steroids, organic acids, saccharides, glycosides, and phloroglucinol adducts, were isolated and identified in CSR. These compounds render CSR with pharmacological functions, such as anti-aging, anti-oxidation, anti-fatigue, and anti-HIV activities, and the effects of CSR on immune system, nervous system, reproductive system, and other bioactivities were well reviewed; results serve as valuable data for further research and for development of human health-related products. However, studies on CSR were far from perfect, and further research is warranted. This paper highlights the components and pharmacological functions of CSR, with the aim to provide a comprehensive review and useful data for future studies and for the development of relevant food products.
Chemical Composition and Antinociceptive Potential of Plinia edulis Fruits Peels
Authors: Nesello Luciane Angela Nottar , Campos Adriana , Capistrano Karla , de Campos Buzzi Fátima , Filho Valdir Cechinel
Published: March 2019

The present study deals with the chemical composition and antinociceptive effects of Plinia edulis fruit peels, analyzed by writhing, formalin, glutamate and capsaicin tests and comparison with two reference analgesic drugs, acetylsalicylic acid and acetaminophen. Phytochemical analyses of the nonpolar fraction (dichloromethane) obtained from the peels of P. edulis fruits revealed the presence of two triterpenes, maslinic acid and ursolic acid. The methanol extract of P. edulis peels showed a pronounced antinociceptive activity in the writhing test, with inhibition of 91.3% at 10 mg/kg, and its dichloromethane and ethyl acetate fractions presented inhibition of 68.3% and 51.5%, respectively. Maslinic acid showed a dose-dependent effect with inhibition of 60.8% at a dose of 10 mg/kg and ID50 value of 3.31 (2.75 to 4.0) mg/kg. The dichloromethane fraction, evaluated in the formalin-induced pain model at a dose of 10 mg/kg, showed a significant effect on both phases of pain. Maslinic acid was evaluated at different doses (1, 3 and 6 mg/kg) and presented a dose-dependent profile in both phases of pain, being more effective than the reference drug (acetaminophen), which was evaluated at 10 mg/kg. The dichloromethane fraction also inhibited the pain induced by glutamate and capsaicin by around 54% and 44%, respectively, whereas maslinic acid was more effective against glutamate, with 62.5% inhibition at 6 mg/kg, and 32% inhibition against capsaicin-induced pain. The results demonstrated that the pronounced antinociceptive effect presented by P. edulis fruits peels is related, at least in part, to the presence of the triterpenes evidenced in this study.
Flavonoid Aglycones and Glycosides from the Leaves of some Japanese Artemisia Species
Authors: Uehara Ayumi , Shimoda Kazuhide , Murai Yoshinori , Iwashina Tsukasa
Published: March 2019

Sixteen Japanese Artemisia taxa were surveyed for flavonoid aglycones and glycosides. The leaves were rinsed with acetone and then extracted with MeOH. Isolated flavonoids were identified by UV, LC-MS, acid hydrolysis, 1H and 13C NMR, and/or HPLC comparisons with authentic samples. Thus, nine flavone aglycones, apigenin (10), luteolin (5), chrysoeriol (11), hispidulin (6), jaseosidin (7), nepetin (15), sudachitin (8), luteolin 7-methyl ether (13) and eupatilin (14), three flavonol aglycones, axillarin (9), quercetin 3-methyl ether (16) and 5,7,4′-trihydroxy-3,6-dimethoxyflavone (12), one flavanone aglycone, pinocembrin (4), three dihydroflavonol aglycones, taxifolin (1), taxifolin 3-acetate (2) and padmatin (3) were found in their Artemisia taxa with the various combination. On the other hand, four flavonol glycosides, quercetin 3- O-rutinoside (17), quercetin 3- O-glucoside (18), patuletin 3- O-glucoside (19) and patuletin 3- O-rhamnosylglucoside (20), were isolated from a few Artemisia taxa.
Antioxidant and Cosmeceutical Activities of Agarum cribrosum Phlorotannin Extracted by Ultrasound Treatment
Authors: Phasanasophon Kasira , Kim Sang Moo
Published: March 2019

An ultrasonic process for the effective extraction of phlorotannins from Agarum cribrosum with high total phlorotannin content (TPC) was optimized using response surface methodology (RSM). Optimal conditions for ultrasound extraction consisted of temperature: 30°C; time: 5.75 h; ratio of solvent to solid: 35 mL/g, where the TPC was 19.59 mg PGE/g. The crude extract was further partitioned using hexane, dichloromethane, ethyl acetate (EtOAc), and water, in that order. The EtOAc fraction with the highest TPC exhibited the strongest radical-scavenging activity against DPPH, ABTS, hydrogen peroxide, and reducing power, which was similar to that of ascorbic acid. Furthermore, the IC50 values of the EtOAc fraction against collagenase, elastase, and tyrosinase inhibitory activity were 29.63, 16.13, and 6.17 μg/mL, respectively, whereas epigallocatechin gallate (EGCG), EGCG, and kojic acid, the counterpart positive controls, were 68.90, 23.34, and 43.29 μg/mL, respectively. The EtOAc fraction was further fractionated using Sephadex LH-20 column chromatography, which yielded two major and four minor subfractions. The structure of the SF5 and SF6 subfractions were further determined through HPLC-DAD-QMS analyses and 1H and 13C NMR, in which only trifuhalol A was identified. The SF5 and SF6 subfractions exhibited significantly higher radical-scavenging activity against DPPH and reducing power than the EtOAc fraction, but no statistically significant differences were detected for ABTS, hydrogen peroxide, collagenase, elastase, and tyrosinase inhibitory activity. Based on the results, we propose that A. cribrosum phlorotannins could be a good source for natural antioxidants and cosmeceutical.
Synthesis of Sex Pheromones of the Citrus Leafminer (CLM) (Phyllocnistis citrella)
Authors: Kumar Alleni Suman , Satyanarayana Vavilapalli , Alghamdi Ahmad Alkhazim , Yadav Jhillu Singh
Published: March 2019

A convergent and efficient total synthesis of sex Pheromones has been achieved. The synthesis exploits the Wittig reaction, hydrogenation and oxidation as key steps.
Composition, Anti-inflammatory Activity, and Bioaccessibility of Green Seaweeds from Fish Pond Aquaculture
Authors: Ripol Andrea , Cardoso Carlos , Afonso Cláudia , Varela João , Quental-Ferreira Hugo , Pousão-Ferreira Pedro , Bandarra Narcisa M.
Published: March 2019

The nutritional composition was studied of green seaweeds ( Chaetomorpha linum, Rhizoclonium riparium, Ulva intestinalis, U. lactuca, U. prolifera) grown in fish pond aquaculture systems. Moreover, anti-inflammatory activities were measured. The effects of bioaccessibility on this property were assessed. There were qualitative differences in the lipid composition, since fatty acid profiles varied among seaweed species. Whereas U. lactuca and U. intestinalis fatty acid profiles were very similar, all other profiles differed significantly. U. prolifera was very rich in ω6 PUFA, while R. riparium was richer in ω3 PUFA. Concerning the ω3/ω6 ratio, the highest value was found for C. linum. The anti-inflammatory activity was higher for U. prolifera and C. linum with high cyclooxygenase-2 activity inhibition (ranging between 18 and 27 %) upon incubation of 100 μg/mL of these green seaweed extracts. Though the compounds causing this effect were not bioaccessible, U. prolifera seems to be a potential source of bioactive compounds.
A New Immunosuppressive Pregnane Glycoside and Two Known Analogues from Epigynum cochinchinensis
Authors: Shao Yuting , Zhao Yan , Zhang Hong , Jiang Mengjun , Khan Afsar , Zhao Tianrui , Zhou Zhihong , Cheng Guiguang , Cao Jianxin
Published: March 2019

Phytochemical investigation of the ethyl acetate soluble fraction from the leaves of Epigynum cochinchinensis led to the isolation of one new C21 pregnane glycoside, epigycoside C (1), along with two known analogues epigycoside A (2) and epigynoside G (3). Their structures were elucidated on the basis of extensive spectroscopic techniques. The in vitro immunosuppressive activity of compound 1 was evaluated against concanavalin A (Con A)- and lipopolysaccharides (LPS)-stimulated proliferation of mice splenocytes. Compound 1 displayed significant immunosuppressive activities in a dose-dependent manner.
Bioactive Components of Fissistigma cupreonitens
Authors: Chen I-Hsiao , Yang Ming-Yi , Juang Shin-Hun , Lee Chia-Lin , Thang Tran-Dinh , El-Shazly Mohamed , Lan Yu-Hsuan
Published: March 2019

Phytochemical investigation of Fissistigma cupreonitens (Annonaceae) led to the isolation of 34 compounds. The chemical structures of all compounds were determined by spectroscopic methods. Among the isolates, compounds 20–27 and 31–34 were reported from this genus for the first time. From the results of the cytotoxicity assay against three human cancer cell lines (NCI-H226, NPC-TW01, and Jurkat E6–1), oxoaporphine compounds oxoxylopine (1), oxocrebanine (3), kuafumine (4) and lysicamine (5), and the flavonoid adunctin E (26) displayed significant cytotoxicity against NCI-H226 cell line, with IC50 values of 8.45, 8.10, 8.54, 12.83 and 12.00 μM, respectively, in comparison with the standard drug, cisplatin with IC50 of 13.37 μM.
Indole Alkaloids from Tropical Sponge Hyrtios sp. as Isocitrate Lyase Inhibitors
Authors: Park Seung-Il , Lee Yeon-Ju , Won Hoshik , Oh Ki-Bong , Lee Hyi-Seung
Published: March 2019

A new β-carboline alkaloid, 3,4-dihydrohyrtiosulawesine (8), and fifteen known alkaloids were isolated from the tropical marine sponge Hyrtios sp. Among these known compounds, β-ketoserotonin (10) has been isolated for the first time from a natural source. The structures of the isolated compounds were determined by spectroscopic analyses and comparison with literature values. Compound 8 displayed potent inhibitory activities against isocitrate lyase (IC50: 92.9 μM) from Candida albicans.
A New Anti-inflammatory Phenolic Monosaccharide from the Australian Native Rainforest Plant Elaeocarpus Eumundi
Authors: Singh Ahilya , Münch Gerald , Reddell Paul , Radzieta Michael , Jensen Slade O. , Raju Ritesh
Published: March 2019

Chemical analysis of the ethanolic extract of the Australian rainforest plant Elaeocarpus eumundi yielded a new phenolic monosaccharide (1) and the known dihydropieceid (2). The structures of both compounds were elucidated based on the spectroscopic methods including UV, HR-ESIMS and 1D, 2D NMR data. Compounds 1 and 2 exhibited good anti-inflammatory activity in LPS and IFN-γ activated RAW 264.7 macrophage cells.
A New Compound from the Rhizomes of Boesenbergia pandurata
Authors: Van Do Truong Nhat , Nguyen Hai Xuan , Le Tho Huu , Ngo Trang My Thi , Dang Phu Hoang , Phung Nghia Hieu , Vo Nghia Trong , Nguyen Duc Minh , Le Nhan Hong Thi , Le Thanh Thanh , Nguyen Mai Thanh Thi , Awale Suresh , Nguyen Nhan Trung
Published: March 2019

Phytochemical investigation of the methanol extract of the rhizomes of Vietnamese Boesenbergia pandurata resulted in the isolation of a new secondary metabolite named panduratin P (1). The structure of this compound was elucidated by NMR spectroscopic analysis. Compound 1 exhibited a mild activity against PANC-1 human pancreatic cancer cell lines in nutrient-deprived medium (NDM) with PC50 value of 55.9 μM.
Isolation a Homogalacturonan from the Outer Seed Coat of Shaddock (Citrus grandis Osbeck)
Authors: Wang Heng Long , Tu Chin Wei , Wu Wei Zhi , Lin Chen Yi , Chen Su Yu , Yang Wen Jen , Chang Jer Chia , Lu Mei Kuang , Liao Wei Tung
Published: March 2019

An acidic mucilage was isolated from the outer-layer seed coat of shaddock (Citrus grandis Osbeck) by water extraction at room temperature, and purified by DE-52 anion-exchange chromatography using 0.26 – 0.37 M NaCl. This purified mucilage was almost entirely composed of galacturonic acid residues. Glycosyl-linkage analysis showed that the backbone was 1→4 linked. Fourier Transform Infrared Spectroscopic analysis and determination of the degree of methylation further revealed that the mucilage was a low-degree (11.94%) esterified homogalacturonan. Size exclusion chromatography showed that the major molecular weight distribution of 610.9 kDa.
Production of Antioxidant Hydrolyzates from a Lupinus mutabilis (Tarwi) Protein Concentrate with Alcalase: Optimization by Response Surface Methodology
Authors: Intiquilla Arturo , Jiménez-Aliaga Karim , Zavaleta Amparo Iris , Hernández-Ledesma Blanca
Published: March 2019

Lupinus mutabilis (tarwi) is a cultivated legume used principally as a protein source in human and animal nutrition. In this study, protein concentrate was obtained from debittered and defatted tarwi seed flour. SDS-PAGE analysis revealed the presence of highly intense bands ranged between 35 and 60 kDa. Tarwi protein concentrate was subjected to the action of alcalase to produce hydrolyzates with antioxidant activity. A central composite design was employed to study the effect of the experimental variables, enzyme/substrate ratio and incubation time, on the degree of hydrolysis and the radical scavenging capacity. The influence of both variables on the variable responses was demonstrated. The optimal conditions to obtain the highest degree of hydrolysis were enzyme/substrate ratio of 1.72% and 133 min of incubation. The highest radical scavenging activity (TEAC value of 2.7 ± 0.1 μmol Trolox equivalents/mg protein and ORAC value of 3.8 ± 0.1 μmol Trolox equivalents/mg protein) was found in hydrolyzates with alcalase after 138 min and an enzyme/substrate ratio of 1.87%. Peptides released by the action of alcalase and containing hydrophobic and aromatic amino acids could contribute to the antioxidant effects observed. Tarwi proteins could be a new alternative as a food additive with antioxidant properties or as an ingredient of functional foods for health promotion and prevention of free radical-induced chronic diseases.
Design, Synthesis and Cytotoxic Evaluation of Novel Lupane Triterpenoid and Ursolic Acid Derived 2-Aminobenzamides
Authors: Anh Dang Thi Tuyet , Cuc Dinh Thi , Giang Le Nhat Thuy , Hien Nguyen Thi , Doan Vu Ngoc , Thanh Nguyen Ha , Van Tuyen Nguyen , Van Kiem Phan
Published: March 2019

Series of novel triterpenoid hybrids were designed and synthesized by introducing 2-aminobenzamide moiety at C28 position of triterpenoid derivatives. Thirteen new conjugates were thus successfully prepared and evaluated as cytotoxic agents, revealing an interesting anticancer activity in KB and HepG2 cancer cell lines.
Phytochemical Profiles, Antioxidant and Antimicrobial with Antibiofilm Activities of Wild Growing Potentilla visianii Extracts
Authors: Radojević Ivana D. , Branković Snežana R. , Vasić Sava M. , Ćirić Andrija R. , Topuzović Marina D. , Čomić Ljiljana R.
Published: March 2019

We investigated the phytochemical profiles, antioxidant and antimicrobial with antibiofilm activities of methanol and ethyl acetate extracts from the whole plant of Potentilla visianii (Vis. et Panč.) Panč. The major compounds were: epicatechin and quercetin in both extracts. Total phenolic content was determined using spectrophotometric method with Folin-Ciocalteu reagent, the concentration of flavonoids with aluminum chloride and amount of tannins with butanol-HCl reagent. The methanol extract has a significantly higher yield, as well as the content of total phenols and condensed tannins. The antioxidant activity was monitored spectrophotometrically and expressed in terms of IC50 (for methanol extracts 23.8 μg/mL). In vitro antimicrobial activity was investigated by microdilution method against 17 microorganisms. The best results for MIC <0.02 mg/mL showed ethyl acetate extract against Staphylococcus aureus. The antifungal activity of extracts on Penicillium chrysogenum was in the range of positive control. The influence on biofilm formation and preformed biofilm was different. Escherichia coli ATCC 25922 and Bacillus subtilis ATCC 6633 were more sensitive as formed biofilms. S. aureus ATCC 25923 could be influenced by extracts only during the biofilm formation.
Apoptotic-induced Effects of Castanea sativa Bark Extract in Human SH-SY5Y Neuroblastoma Cells
Authors: Santulli Chiara , Brizi Claudia , Durante Miriam , Micucci Matteo , Budriesi Roberta , Chiarini Alberto , Frosini Maria
Published: March 2019

Castanea sativa Mill. wood extract (ENC) has health-promoting qualities such as antibacterial, antiviral, antispasmodic, cardio- and neuroprotective-activities. Its potential towards cancer cells of the central nervous system, however, is still unexplored. This study investigates the apoptotic-enhancing effect of ENC in human neuroblastoma SH-SY5Y cell line. This extract irreversibly decreased cell viability with IC50 of 142.8±20.2, 109.3±16.6 and 82.5±8.6 μg/mL for 24h, 48 and 72h of treatment, respectively. This was accompanied by cell shrinkage and tendency to round-up. A concentration-dependent increase in sub G0/G1 cells as well as a rise in cells with nuclear fragmentation and chromatin condensation, both typical of apoptosis, was also observed. In conclusion, the present findings provide initial data on the potential of ENC for neuroblastoma treatment and offer the rationale for further studies aimed at elucidating the full mechanism(s) underlying its effects.
Ethnopharmacological, Phytochemical, Pharmacological and Toxicological Aspects of Bauhinia forficata: A Mini-Review Covering the Last Five Years
Authors: Cechinel-Zanchett Camile Cecconi , de Andrade Sérgio Faloni , Cechinel-Filho Valdir
Published: March 2019

This mini review focuses on the ethnopharmacology, phytochemical, and biological/pharmacological activity and toxicology of the medicinal plant, Bauhinia forficata reported during 2012–2016. The results confirmed the continuous use of this plant, especially the leaves, for medicinal purposes, particularly as remedies for the treatment of diabetes and other ailments. Other new biological potential was evidenced, including anti-ulcerogenic, hypocholesterolemic, hepatoprotective and diuretic effects. Clinical and toxicological studies have advanced gradually, requiring more detailed experiments, to ensure the safe use of this plant for medication. Some new flavonoids were detected in this species, but significant differences were observed when comparing the chemical composition of its sub-species.
Synthesis of Ester-linked Taxol-oligosaccharide Conjugate and Its Drug Delivery System Using Bio-nanocapsules and Hybrid-bio-nanocapsules
Authors: Hamada Hiroki , Okada Shouta , Masuoka Noriyoshi , Fujitaka Yuya , Shimoda Kei , Doi Shouta , Mikuni Katsuhiko
Published: March 2019

Synthesis of ester-linked oligosaccharide conjugate of taxol, i.e., 7-glycolyltaxol 2″- O-α-maltotrioside, was investigated by enzymatic procedure. The starting material, 7-glycolyltaxol 2″- O-α-D-glucoside, was glycosylated by cyclodextrin glucanotransferase to 7-glycolyltaxol 2″- O-α-maltooligosides [α-maltooligosaccharides; α-Glc-1→(4-α-Glc-1→)n-14-α-glucosides (n = 1–4)]. The enzymatic hydrolysis of 7-glycolyltaxol 2″- O-α-maltooligosides gave 7-glycolyltaxol 2″- O-α-maltotrioside. Both bio-nanocapsules and hybrid-bio-nanocapsules containing 7-glycolyltaxol 2″- O-α-maltotrioside exhibited high in vitro anti-tumor activities.
Inhibitory Effect of Pelargonidin on Secretory Group IIA Phospholipase A2
Authors: Lee In-Chul , Bae Jong-Sup
Published: March 2019

The expression of secretory group IIA phospholipase A2 (sPLA2-IIA) has been shown to be elevated in various inflammatory diseases, and lipopolysaccharide (LPS) up-regulates the expression of sPLA2-IIA in human umbilical vein endothelial cells (HUVECs). Pelargonidin (PEL) is a well-known red pigment found in plants, and has been reported as having important biological activities that are potentially beneficial for human health. Here, PEL was examined for its effects on the expression and activity of sPLA2-IIA in HUVECs and mouse. Post treatment of cells or mouse with PEL inhibited LPS-induced expression and activity of sPLA2-IIA. Therefore, these results suggest that PEL inhibited LPS mediated expression of sPLA2-IIA.
Identification of Plant Origin of Propolis from Thailand Stingless Bees by Comparative Analysis
Authors: Ishizu Eriko , Honda Sari , Vongsak Boonyadist , Kumazawa Shigenori
Published: March 2019

Propolis is a resinous mixture of substances collected by honey bees from certain plants. It has gained popularity as a food and alternative medicine. We recently obtained Thailand stingless bee propolis. However, to the best of our knowledge, there are only a few studies on native Thailand stingless bee propolis. The purpose of this study was to analyze the composition of Thailand stingless bee propolis and to identify its plant origin. Comparative analysis of the 70% ethanol extracts of Thailand stingless bees propolis and the yellow resin from the fruit surface of Garcinia mangostana was performed using reversed-phase high-performance liquid chromatography coupled with high resolution-electrospray mass spectrometry. The extracts showed the similar chromatographic patterns. In conclusion, we suggest that the plant origin of Thailand stingless bee propolis is the yellow resin from fruit surface of G. mangostana.
Potent α-Glucosidase Inhibitors from the Roots of Aruncus sylvester
Authors: Li Zhang-Peng , Que Meng , Gao Wen-Yuan , Su Yan-Fang
Published: March 2019

Two new acyl glucoses, 1,3,6-tri- O-( E)-caffeoyl-β-D-glucopyranoside (1) and 3,4-di- O-( E)-caffeoyl-α/β-D-glucopyranose (2), along with four known ones (3–6), were isolated from the roots of Aruncus sylvester. Their structures were elucidated on the basis of NMR spectroscopic analysis. Compounds 1 and 3 showed potent α-glucosidase inhibitory activity with IC50 values of 1.16 μM and 0.71 μM, respectively.
Cytotoxic Compounds from the Seeds of Sophora alopecuroides
Authors: Song Ping , Chen Hao , Wen Yanzhang , Lv Yibing , Deng Shihao , Yang Xinzhou
Published: March 2019

Chemical purification of the ethyl acetate extract from the seeds of Sophora alopecuroides yielded a new natural product, ethyl 2-(4-hydroxybenzyl) malic acid (1), along with 7 known compounds, methyl eucomate (2), eucomic acid (3), piscidic acid (4) and ethyl 2-(4-hydroxybenzyl) tartrate (5), butein-4'-O-β-D-glucopyranoside (6), iso-liquiritigenin (7), and butein (8). The structure of 1 was determined by spectroscopic analyses including extensive 1D (1H NMR, 13C NMR) and 2D NMR spectra (COSY, HSQC and HMBC) as well as MS data. All compounds were evaluated for their cytotoxic activities against hepato-cellular carcinoma (HCC) cell lines, HepG2 andHep3B. Compound 8 significantly inhibited the cancer cell growth in a concentration-dependent manner.
Anti-Melanogenic Effect of Chestnut Spike Extract through Downregulation of Tyrosinase-Related Proteins and Activation of ERK 1/2
Authors: Byeon Jung-Hee , Alam Md Badrul , Kim Ki-Chan , Heo Sangsun , Lim Ji-young , Kwon Yoon-Gyung , Zhao Peijun , Cha Yeong-Ho , Choi Hee-Jeong , Lee Sang-Han
Published: March 2019

Melanin has been reported to be the key factor for skin homeostasis. Besides defining an important human phenotypic trait, melanin overproduction may cause various disorders such as vitiligo, Addison's disease, Cushing's syndrome, and melasma. In this study, we aimed to investigate the anti-melanogenic potential of dried spike extract of chestnut. The extract inhibited tyrosinase (TYR) activity in a dose-dependent manner. Cellular melanin content decreased markedly after treatment with the extract. The spike extract inhibited microphthalmia-associated transcription factor (MITF) expression and downregulated TYR, TYRP-1, and TYRP-2 protein expression by increasing the phosphorylation of extracellular signal-regulated kinase (ERK)1/2 signalling pathway in melan-a cells. In addition, treatment with U0126, a specific inhibitor of ERK, restored melanin content. Collectively, these results suggest that the chestnut spike extract attenuated melanogenesis by inhibiting MITF expression and downregulating TYR, TYRP-1, and TYRP-2 protein expressions via activation of ERK1/2 pathway.
Analysis of the Volatile Components of Pouteria sapota (Sapote Mamey) Fruit by HS-SPME-GC-MS
Authors: Rodríguez Candelario , Durant-Archibold Armando A. , Santana Ana , Murillo Enrique , Abuín Carlos M. Franco
Published: March 2019

The comparison of SPME fiber coatings, and optimization of temperature and time of extraction for headspace solid phase microextraction (HS-SPME) of volatile organic compounds (VOCs) present in Pouteria sapota (sapote mamey) fruits is presented. The PDMS/DVB coating afforded the highest extraction efficiency. The extraction conditions were optimized by using Doehlert experimental design. By using the optimized HS-SPME method, 21 VOCs were identified, which include mainly terpenoids and esters, followed by aromatic hydrocarbons, aldehydes, alcohols and ketones. The most abundant compounds in Pouteria sapota pulp were cedrol (25.0%), azulene (7.3%), β-ionone (5.7%) naphthalene (5.6%), α-pinene (5.0%), and benzaldehyde (4.3%). Seventeen VOCs were identified for the first time in the fruit.
Antifungal and Insecticidal Properties of Juniperus thurifera Leaves
Authors: Jemli Meryem El , Khattabi Naima , Lachqer Khadija , Touati Driss , Jemli Yousra El , Marmouzi Ilias , Wakrim El Mahdi , Cherrah Yahia , Alaoui Katim
Published: March 2019

The hydro-distilled essential oil from the leaves of Juniperus thurifera L. (JTEO) was analyzed by GC-MS and examined for its insecticidal, antifungal and antioxidant activities. A total of 51 compounds were identified. The major components were sabinene (22.4%), followed by terpinen-4-ol (11.0%) and α-pinene (5.9%). JTEO exhibited interesting insecticidal activity against adults of Acanthoscelides obtectus, Tribolium castaneum and Sitophilus oryzae, with LC50 values of 0.1, 0.6 and 2.0×10−2 μL/mL, respectively. Moreover, JTEO showed inhibitory activity against Alternaria alternata, Fusarium oxysporum, Fusarium solani, Rhizoctonia solani and Verticillium dahlia with mycelial growth inhibition ranging from 24.0% to 92.1%. Finally, JTEO demonstrated a moderate antioxidant effect.
A New Triterpene Glucoside from Genista numidica
Authors: Benayache Feryal , D'Ambola Massimiliano , Cotugno Roberta , Chaouche Massika , Benayache Samir , Benayache Fadila , Braca Alessandra , De Tommasi Nunziatina
Published: March 2019

A new oleanolic acid triterpene glucoside, 3- O-β-D-glucopyranosyl-3β,21β,28-trihydroxy-olean-12-en-27-oic acid (1), has been isolated together with twelve known compounds from the chloroform and ethyl acetate extracts of Genista numidica Spach (Fabaceae) aerial parts. The structures were elucidated by spectroscopic and spectrometric analyses, mainly 1D-, 2D-NMR and MS data, and comparison with the literature. The antiproliferative activity of isolates was investigated on Jurkat, HeLa, and MCF7 cell lines. The most active triterpene, 3- O-β-D-glucopyranosyl-olean-12-en-3β,27,28,29-tetraol, showed activity in all cell lines. Further studies revealed that this compound induced in HeLa cells a cytostatic response.
Biological Effects of Saponin Fractions from Astragalus verrucosus in Tumor and Non-tumor Human cells
Authors: Facioni Maria Sole , Soares Joana , Adinolfi Barabara , Gomes Sara , Raimundo Liliana , Contini Adele , Ruffoni Barbara , Azzarà Alessia , Tavanti Arianna , Bertoli Alessandra , Pistelli Luisa , Saraiva Lucilia , Scarpato Roberto
Published: March 2019

Among natural chemicals used as cancer chemo-preventive and/or chemotherapeutic agents, saponins represent one of the most promising and interesting family of compounds. In this work, we aimed to elucidate the biological effects on human cells of six saponin fractions (SFs) obtained from in vitro cultures of Astragalus verrucosus Moris, a poorly characterized species. Interestingly, SF (3) showed a strongly inhibitory effect on the proliferation of human colon adenocarcinoma cell line (HCT116) via activation of a p53-dependent apoptotic pathway. In addition, SF (3) and the other SFs did not display genotoxic activity in human peripheral lymphocytes.
Cannabichromene
Authors: Pollastro Federica , Caprioglio Diego , Del Prete Danilo , Rogati Federica , Minassi Alberto , Taglialatela-Scafati Orazio , Munoz Eduardo , Appendino Giovanni
Published: March 2019

Cannabinochromene (CBC, 1a) is the archetypal member of a class of more than twenty isoprenylated 5-hydroxy-7-alkyl(aralky)benzo[2 H]pyranes first reported from Cannabis sativa L. but also occurring in unrelated plants ( Rhododendron species) as well as liverworts and fungi. The chemistry, synthesis, and bioactivity of CBC (1a) is reviewed, highlighting its underexploited pharmacological potential and rich chemistry.
Synthetic Esterification of Yacon Sesquiterpene Lactone, Sonchifolinic Acid led to Cytotoxic SARs Study
Authors: Kitai Yurika , Nishiwaki Hisashi , Yonekura Lina , Tamura Hirotoshi
Published: March 2019

Cytotoxicity on sonchifolinic acid (1) isolated from Samallunthus leaf and synthetic compounds related to compound 1 were comparatively studied for the first time. Derivatives of 1 such as propyl (1a), butyl (1b), pentyl (1c) and 2-methoxy ethyl (1d) sonchifolate were prepared and their cytotoxic activity on HeLa cells were compared with sonchifolin (2), a structurally related natural compound. Alkylation of the carboxylic acid group at C-14 position in 1 enhanced the cytotoxic activity 2–5 times (1a - 1d and 2, IC50 5.29 - 21.07 μM) compared with that of sonchifolinic acid (1) (IC50 47.12 μM). Higher lipophilicity and moderate bulkiness of the inserted alkyl group contributed to the increased SL cytotoxicity in vitro. This result shows sonchifolinic acid (1) could be a valuable leading compound for semi-synthetic derivatives in order to develop new potent anticancer drugs.