bluuebunny/crossref_metadata_2025 huggingface dataset:
Antioxidant, Antiproliferative and Antimicrobial Activities of the Volatile Oil from the Wild Pepper Piper capense Used in Cameroon as a Culinary Spice
Authors: Woguem Verlaine , Maggi Filippo , Fogang Hervet P. D. , Tapondjou Léon A. , Womeni Hilaire M. , Quassinti Luana , Bramucci Massimo , Vitali Luca A. , Petrelli Dezemona , Lupidi Giulio , Papa Fabrizio , Vittori Sauro , Barboni Luciano
Published: March 2019

Wild pepper (Piper capense L.f., Piperaceae) is a spice traditionally used in western Cameroon to make soups called ‘ Nkui’ and ‘ Nah poh’. In the present work, the essential oil hydrodistilled from fruits was analyzed by GC-FID and GC-MS, and for in vitro biological activities, namely cytotoxic, antioxidant and antimicrobial, by MTT, DPPH, ABTS and agar disc diffusion methods. The oil composition was dominated by monoterpene hydrocarbons (56.5%) responsible for the pepper odor, such as β-pinene (33.2%), sabinene (10.0%) and α-pinene (8.9%). The oil induced a concentration-dependent inhibitory effect on human tumor cells MDA-MB 231 (breast adenocarcinoma), A375 (malignant melanoma) and HCT116 (colon carcinoma), showing IC50 values of 26.3, 76.0 and 22.7 μg/ml, respectively. The oil showed total antioxidant activity with a Trolox equivalent antioxidant concentration (TEAC) value of 140 μmol/g. The essential oil of P. capense proved to be an effective scavenger of the ABTS+ radical, with an activity only about 30 times lower than that of Trolox. Moderate activity was observed against the Gram-positive species Staphylococcos aureus and Enterococcus faecalis, and the yeast Candida albicans. The notable inhibition of some human tumor cells is worthy of further investigation to discover the possible mechanisms of action responsible for the observed cytotoxic effect of this essential oil.
Boldine and Related Aporphines: From Antioxidant to Antiproliferative Properties
Authors: Muthna Darina , Cmielova Jana , Tomsik Pavel , Rezacova Martina
Published: March 2019

Plant and folk medicine represent nowadays a source of either new therapeutic substances or substrates for drug synthesis. One such promising group for possible further exploitation is the family of aporphine alkaloids containing boldine and related compounds. In this mini-review we focus on boldine and its newly described effects, which predominantly arise from its antioxidant properties. Moreover, we try to compare its antiproliferative properties with other better known members of the aporphine group.
Methods for Extraction and Determination of Phenolic Acids in Medicinal Plants: A Review
Authors: Arceusz Agnieszka , Wesolowski Marek , Konieczynski Pawel
Published: March 2019

Phenolic acids constitute a group of potentially immunostimulating compounds. They occur in all medicinal plants and are widely used in phytotherapy and foods of plant origin. In recent years, phenolic acids have attracted much interest owing to their biological functions. This paper reviews the extraction and determination methods of phenolic acids in medicinal plants over the last 10 years. Although Soxhlet extraction and ultrasonic assisted extraction (UAE) are commonly used for the extraction of phenolic acids from plant materials, alternative techniques such as supercritical fluid extraction (SFE), and accelerated solvent extraction (ASE) can also be used. After extraction, phenolic acids are determined usually by liquid chromatography (LC) owing to the recent developments in this technique, especially when it is coupled with mass spectrometry (MS). Also detection systems are discussed, including UV-Vis, diode array, electrochemical and fluorimetric. Other popular techniques for the analysis of this group of secondary metabolites are gas chromatography coupled with mass spectrometry (GC-MS) and capillary electrophoresis (CE).
A New Dolabellane Diterpenoid and a Sesquilignan from Aglaia odorata var. microphyllina
Authors: Liu Shuai , Yang Wei , Liu Shou-Bai , Wang Hui , Guo Zhi-Kai , Zeng Yan-Bo , Dong Wen-Hua , Mei Wen-Li , Dai Hao-Fu
Published: March 2019

One new diterpenoid, 11 α,12 βH-dolabella-4,8(17)-dien-3 α,7 β,18-triol (1) and one new sesquilignan, 9-methoxy-7′,8′- cis–7″,8″-cis-buddlenol B (2), together with three known compounds, (+)-diasyringaresinol (3), N-methyl-5- hydroxy-Δ3-pyrrolin-2-one (4) and marmin (5), have been isolated from Aglaia odorata var. microphyllina. Their structures were determined using 1D and 2D NMR spectroscopy. Compound 1 exhibited cytotoxic activity against the K562 cell line with an IC50 value of 12.5 μg/mL.
A New Diterpenoid from the Aerial Parts of Andrographis paniculata
Authors: Wang Chun-Hua , Li Wen , Qiu Rui-Xia , Jiang Miao-Miao , Li Guo-Qiang
Published: March 2019

One new and seven known diterpenoids were isolated from the aerial parts of Andrographis paniculata, and their structures elucidated on the basis of spectroscopic and spectrometric analysis, as well as chemical methods. The in vitro antiviral activities of these compounds against respiratory syncytial virus (RSV) were assayed.
Inhibitory Effect of the Plant Clusia fluminensis against Biological Activities of Bothrops jararaca Snake Venom
Authors: de Oliveira Eduardo Coriolano , Anholeti Maria Carolina , Domingos Thaisa Francielle , Faioli Camila Nunes , Sanchez Eladio Flores , de Paiva Selma Ribeiro , Fuly André Lopes
Published: March 2019

The ability of extracts of the plant Clusia fluminensis Planch & Triana (Clusiaceae Lindl.) to neutralize proteolysis, clotting, hemolysis, hemorrhagic and lethality activities of Bothrops jararaca snake venom was studied. Clusianone and lanosterol from the flower and fruit extracts, respectively, were also tested. The extracts of different organs of C. fluminensis inhibited proteolysis and hemolysis induced by B. jararaca venom, but with different potencies. Only the stems prevented blood clotting. Only the acetone extract of the fruit protected mice from hemorrhage while the acetone or methanol extracts prevented mice from death. Clusianone and lanosterol did not inhibit clotting or hemorrhage, but the former inhibited proteolysis and the latter hemolysis.
Antifungal Activity of Metabolites from the Marine Sponges Amphimedon sp. and Monanchora arbuscula against Aspergillus flavus Strains Isolated from Peanuts (Arachis hypogaea)
Authors: Arevabini Cynthia , Crivelenti Yasmin D. , de Abreu Mariana H. , Bitencourt Tamires A. , Santos Mário F. C. , Berlinck Roberto G. S. , Hajdu Eduardo , Beleboni Renê O. , Fachin Ana L. , Marins Mozart
Published: March 2019

Contamination of preharvest and stored peanuts ( Arachis hypogaea L.) by aflatoxigenic strains of Aspergillus flavus is an important economical and food safety problem in many tropical and subtropical areas of the world. The present investigation reports the antifungal activity of a halitoxins/amphitoxins enriched extract obtained from the sponge Amphimedon sp. (HAEEAsp), and of batzelladine L isolated from the sponge Monanchora arbuscula on Aspergillus flavus isolated from stored peanuts. A PCR system directed against the ITS region and aflatoxin biosynthetic pathway genes of A. flavus was applied for identification of aflatoxin producing strains. The HAEEAsp extract and batzelladine L showed minimal inhibitory concentration (MIC) in the range between 1.9 to 15.6 μg/mL and between 1.9 to 7.8 μg/mL, respectively. The minimal fungicide concentration (MFC) of HAEEAsp extract and batzelladine L was in the range between 3.9 to 31.3 μg/mL and 3.9 to 15.6 μg/mL, respectively. These results indicate that these marine alkaloids may be further explored for the development of potential lead compounds active against aflatoxigenic fungi.
Synthesis of Sepiapterin-C via Hydrolysis of 6-Ethynylpteridine
Authors: Nxumalo Winston , Dinsmore Andrew
Published: March 2019

Acid hydrolysis of 6-ethynylpteridine catalyzed by mercury oxide gives 6-acetyl-2-amino-3,4-dihydropteridin-4-one in good yield. Partial reduction of the product with dissolved Al in NH3 solution afforded sepiapterin-C.
Determination of Catechins from Elephantorrhiza elephantina and Pentanisia prunelloides using Voltammetry and UV spectroscopy
Authors: Mpofu Smart J. , Arotiba Omotayo A. , Hlekelele Lerato , Ndinteh Derek T. , Krause Rui W.M.
Published: March 2019

In this work, we report the identification and quantification of catechins by electrochemistry and UV-Vis spectroscopy in Elephantorrhiza elephantina (Fabaceae) and Pentanisia prunelloides (Rubiaceae), both of which are medicinal plants that are widely used in Southern Africa to remedy various ailments. A comparative study of the catechin content as (-)-epicatechin equivalent is reported for the first time, with E. elephantina exhibiting a higher concentration relative to P. prunelloides in both aqueous and methanol extracts.
Induction of Apoptosis and Cell Cycle Arrest in Human Colon Carcinoma Cells by Corema album Leaves
Authors: León-González Antonio J. , Manson Margaret M. , López-Lázaro Miguel , Navarro Inmaculada , Martín-Cordero Carmen
Published: March 2019

The leaves of Corema album (Ericaceae), an endemic shrub which grows in Atlantic coastal areas of the Iberian Peninsula, are rich in flavonoids and other secondary metabolites. Silica gel column chromatography of the ethyl acetate extract from dried leaves was performed and a flavonic active fraction was obtained. The cytotoxic activity of this fraction was assessed using the colon cancer cell lines HCT116 and HT29. After 48 hours of treatment, cell viability was determined with luminescence-based ATPLite assay, showing IC50 values of 7.2 ± 0.7 and 6.8 ± 1.2 μg/mL, respectively. The study by flow cytometry revealed that the cytotoxicity of this fraction was mediated, at least in part, by induction of apoptosis and G2/M cell cycle arrest. The active fraction was then subjected to Sephadex LH-20 chromatography and two flavonoids were separated and identified as the flavanone pinocembrin and 2′,4′-dihydroxychalcone after UV, MS and NMR analysis.
8-Hydroxycudraxanthone G Suppresses IL-8 Production in SP-C1 Tongue Cancer Cells
Authors: Setiawan Arlette S. , Oewen Roosje R. , Supriatno  , Soewondo Willyanti , Sidik  , Supratman Unang
Published: March 2019

Production of IL-8 primarily promotes angiogenic responses in cancer cells, which lead to favorable disease progression. Suppressing this production may, therefore, be a significant therapeutic intervention in targeting tumor angiogenesis. This study aimed to evaluate the reduction effects of xanthones in cancer cell lines. Nine known prenylated xanthones (1–9), isolated from the pericarp of Garcinia mangostana Linn (GML), were tested for their ability to suppress IL-8 (interleukin-8) of the SP-C1 (Supri's Clone 1) tongue cancer cell line. Of these compounds, 8-hydroxycudraxanthone-G (4) suppressed IL-8 within 48 hours. This is the first report of 8-hydroxycudraxanthone G suppressing the production of IL-8 (45% at 15.7 μg/mL in 48 hours). These results suggest that the prolonged suppression of IL-8 production by cancer cell lines is concerned in the anti-cancer activity of 8-hydroxycudraxanthone.
Antiplatelet Aggregation Effects of Phenanthrenes from Calanthe arisanensis
Authors: Lee Chia-Lin , Yen Ming-Hon , Chang Fang-Rong , Wu Chin-Chung , Wu Yang-Chang
Published: March 2019

Three phenanthrenes (1–3), four indole alkaloids (4–7) and one steroid (8) were isolated from the leaves of Calanthe arisanensis for the first time. In the antiplatelet aggregation assay, phenanthrenes 1 and 2 showed potential antiplatelet activity. We have reported and discussed here the antiplatelet aggregation properties of the eleven naturally-occurring phenanthrenes (1–2 and 9–17) isolated from the underground part of the plant and eighteen chemically synthesized phenanthrenes (18–35). Overall, our data demonstrated that 1,4-phenanthrenequinones 20, 21 and 22 (collagen, IC50 0.2, 0.2, 0.1 μg/mL; thrombin, IC50 0.8, 1.0, 1.1 μg/mL, respectively) could be promising lead candidates for further cardiovascular disease studies.
In Vivo Anti-inflammatory Activity of Some Naturally Occurring O- and N-Prenyl Secondary Metabolites
Authors: Epifano Francesco , Genovese Salvatore , Fiorito Serena , Loggia Roberto della , Tubaro Aurelia , Sosa Silvio
Published: March 2019

A series of O- and N-prenyl secondary metabolites of insect, fungal, and plant origin have been evaluated for their topical anti-inflammatory activity using the Croton oil ear test in mice as a model of acute inflammation. Some of the tested compounds revealed an effect (ID50 = 0.31 +0.56 μmol/cm2) comparable with that of the reference non-steroidal anti-inflammatory drug indomethacin (ID50 = 0.23 μmol/cm2).
Enzyme-treated Asparagus officinalis Extract Shows Neuroprotective Effects and Attenuates Cognitive Impairment in Senescence-accelerated Mice
Authors: Sakurai Takuya , Ito Tomohiro , Wakame Koji , Kitadate Kentaro , Arai Takashi , Ogasawara Junetsu , Kizaki Takako , Sato Shogo , Ishibashi Yoshinaga , Fujiwara Tomonori , Akagawa Kimio , Ishida Hitoshi , Ohno Hideki
Published: March 2019

Increases in the number of patients with dementia involving Alzheimer's disease (AD) are seen as a grave public health problem. In neurodegenerative disorders involving AD, biological stresses, such as oxidative and inflammatory stress, induce neural cell damage. Asparagus ( Asparagus officinalis) is a popular vegetable, and an extract prepared from this reportedly possesses various beneficial biological activities. In the present study, we investigated the effects of enzyme-treated asparagus extract (ETAS) on neuronal cells and early cognitive impairment of senescence-accelerated mouse prone 8 (SAMP8) mice. The expression of mRNAs for factors that exert cytoprotective and anti-apoptotic functions, such as heat-shock protein 70 and heme oxygenase-1, was upregulated in NG108–15 neuronal cells by treatment with ETAS. Moreover, when release of lactate dehydrogenase from damaged NG108–15 cells was increased for cells cultured in medium containing either the nitric oxide donor sodium nitroprusside or the hypoxia mimic reagent cobalt chloride, ETAS significantly attenuated this cell damage. Also, when contextual fear memory, which is considered to be a hippocampus-dependent memory, was significantly impaired in SAMP8 mice, ETAS attenuated the cognitive impairment. These results suggest that ETAS produces cytoprotective effects in neuronal cells and attenuates the effects on the cognitive impairment of SAMP8 mice.
The Use of Cycleave PCR for the Differentiation of the Rejuvenating Herb Species Pueraria candollei (White Kwao Khruea), Butea superba (Red Kwao Khruea), and Mucuna macrocarpa (Black Kwao Khruea), and the Simultaneous Detection of Multiple DNA Targets in a DNA Admixture
Authors: Wiriyakarun Suchaya , Zhu Shu , Komatsu Katsuko , Sukrong Suchada
Published: March 2019

Kwao Khruea, the tuberous roots of Pueraria candollei Graham ex Benth. (White Kwao Khruea), Butea superba Roxb. (Red Kwao Khruea), and Mucuna macrocarpa Wall. (Black Kwao Khruea), are used as rejuvenating herbs in traditional medicine in many tropical countries. Although Kwao Khruea has attracted strong interest because of its rejuvenation properties, each species is used for specific purposes and effects. P. candollei shows estrogenic effects in females. In contrast, B. superba and M. macrocarpa show androgenic effects in males. The potential misidentification of dried tuberous roots of various Kwao Khruea species might cause problems in the drug market, especially when they are reduced into powders. A cycleave PCR, which is based on the sequence of chloroplast matK gene, was developed to differentiate P. candollei, B. superba, and M. macrocarpa. The results showed that cycleave PCR is able to identify specific Kwao Khruea species. A multiplex cycleave PCR was optimized for the simultaneous detection of two different DNA targets in a DNA admixture. The specificity of this technique was confirmed by its ability to distinguish M. macrocarpa from five related Mucuna species. Cycleave PCR can be a specific, sensitive, and rapid method for the identification of medicinal plants and crude plant samples.
Chemical Compositions and Antimicrobial Activity of the Essential Oils of Hornstedtia havilandii (Zingiberaceae)
Authors: Hashim Siti Ernieyanti , Sirat Hasnah Mohd , Yen Khong Heng
Published: March 2019

The chemical compositions and antimicrobial activity of the fresh rhizome and flower oils of Hornstedtia havilandii were studied. The components present were analyzed using GC and GC-MS. A total of forty-eight constituents were successfully identified from the flower and rhizome oils, representing 93.4% and 89.6%, respectively. The most abundant components of the flower oil were β-pinene, (19.5%), β-elemene, (10.0%), β-cubebene, (6.2%), α-pinene, (5.6%), γ-cadinene, (4.3%) and germacrene D, (3.3%), while α-copaene, (10.2%), β-selinene, (8.4%), β-elemene, (7.0%), γ-cadinene, (6.9%), β-cubebene, (5.3%) and germacrene D, (5.3%) were found as the main components of the rhizome oil. The essential oils were tested for antimicrobial activity against Gram-positive bacteria, Gram-negative bacteria and yeasts. Both oils showed activity against the Gram-positive bacterium, Staphylococcus aureus, with moderate MIC values of 112.5 μg/mL, however, for Gram-negative bacteria, the flower oil showed weak antimicrobial activity with a MIC value of 225 μg/mL. Only very weak activity was shown against the yeasts Candida albicans and C. glabrata, with MIC values of 900–1800 μg/mL.
Antinociceptive and Anti-edematous Activities of the Essential Oils of Two Balkan EndemicLaserpitium Species
Authors: Popović Višnja , Petrović Silvana , Tomić Maja , Stepanović-Petrović Radica , Micov Ana , Pavlović-Drobac Milica , Couladis Maria , Niketić Marjan
Published: March 2019

In this paper antinociceptive and anti-edematous effects are examined of the essential oils of the underground parts of two Balkan endemic Laserpitium species (Apiaceae), L. zernyi and L. ochridanum. Furthermore, the essential oil of the underground parts of L. ochridanum is chemically characterised by GC and GC-MS. Antinociceptive and anti-edematous effects were measured in a rat model of localized inflammation, induced by carrageenan, using apparatus for the modified paw-pressure test, and plethysmometer, respectively. The effects of both Laserpitium essential oils were measured after oral gavage administration to male Wistar rats in doses of 25, 50 and 100 mg/kg. The main constituents of L. ochridanum essential oil were: α-pinene (33.2%), α-bisabolol (10.3%) and chamazulene (14.9%). The essential oil of L. zernyi was previously shown to be rich in α-pinene (31.6%) and α-bisabolol (30.9%). Both examined essential oils produced a significant dose-dependent antinociceptive effect. The corresponding ED50±SEM in producing antinociception were 45.9±4.9 mg/kg and 42.4±2.1 mg/kg for L. zernyi and L. ochridanum oil, respectively. Both essential oils also significantly reduced paw edema in a dose-dependent manner. The estimated ED50±SEM values for the anti-edematous effect were 36.3±4.5 mg/kg for L. zernyi oil and 45.1±11.3 mg/kg for L. ochridanum oil. These results suggest that the essential oils of both investigated Laserpitium species may be effective against pain and edema present in various inflammatory conditions.
Intraspecific Variability of the Essential Oil of Cladanthus mixtus from Morocco
Authors: Elouaddari Anass , Amrani Abdelaziz El , JamalEddine Jamal , Barroso José G. , Pedro Luis G. , Figueiredo Ana Cristina
Published: March 2019

Air-dried aerial parts of wild Cladanthus mixtus were collected from two different regions of Morocco, Bouznika and Oujda, during 2011 and 2012. Forty individual plant samples were hydrodistilled using a Clevenger apparatus and the obtained essential oils were analyzed by GC and GC/MS. The yield obtained varies greatly with a range of 0.3 to 0.8%. The chemical composition of C. mixtus oils changes from one region to another. A total of 53 constituents were identified. To the best of our knowledge, two chemotypes were defined for the first time for this species in the regions studied. 2-Methyl-2- trans-butenyl methacrylate (32.8–35.2%) / ar-curcumene (13–14%) characterize the chemotypeof the C. mixtus plants from Bouznika, and trans-β-farnesene (35.5–50.3%) the chemotype from Oujda.
Volatile Organic Compounds of six French Dryopteris Species: Natural Odorous and Bioactive Resources
Authors: Froissard Didier , Rapior Sylvie , Bessière Jean-Marie , Fruchier Alain , Buatois Bruno , Fons Françoise
Published: March 2019

Aerial parts of six Dryopteris species collected in France were investigated for volatile organic compounds (VOC) for the first time. Fifty-three biosynthesized VOC from the shikimic, lipidic and terpenic pathways were identified using gas chromatography/mass spectrometry. Many bioactive polyketide compounds as filicinic derivatives (from 8.5 to 23.5%) and phloroglucinol derivatives (from 8.2 to 53.8%) with various pharmacological activities were detected in high amount from five analysed Dryopteris species, in particular D. oreades and D. borreri, i.e., propionylfilicinic acid (> 10% in D. affinis and D. ardechensis) and 2,6-dihydroxy-4-methoxy-3-methylbutyrophenone (aspidinol) (19.1% and 14.6% in D. oreades and D. borreri, respectively). Several terpenic derivatives with a low odor threshold were identified, i.e., carota-5,8-diene (from 2.5 to 18.4%: floral, woody or fresh bark note), ( E)-nerolidol (> 10% for D. borreri and D. cambrensis; floral or woody odor), α-selinene (> 7% for D. ardechensis; woody-spicy odor), and aristolene (12.8% in D. affinis; flower, sweet odor). The main isoprenoid derivatives were 4-hydroxy-5,6-epoxyionol, 3-oxo-α-ionol and 4-oxo-7,8-dihydro-β-ionone (essentially in D. remota), whereas the main aromatic compound was 4-hydroxy-3-methoxyacetophenone (20.6% and 12.6% in D. cambrensis and D. borreri, respectively) and the main lipid derivative was 1-octen-3-ol with a mushroom-like odor (from 0.4 to 8.3%). Dryopteris species resources are of great interest as a reservoir of odorous and bioactive compounds.
Essential Oil Compositions of Two Populations of Salvia samuelssonii Growing in Different Biogeographical Regions of Jordan
Authors: Bader Ammar , Cioni Pier Luigi , De Tommasi Nunziatina , Flamini Guido
Published: March 2019

The composition of the essential oils of flowering aerial parts of Salvia samuelssonii Rech. fil. (Lamiaceae Section Aethiopis), collected in two different biogeographical regions, has been analyzed. Sample1, collected in a Mediterranean-like region, “As-Subayhi”, contains mainly monoterpenes (54.2%), sesquiterpenes (27.6%) and phenylpropanoids (10.5%), while sample 2, collected in the Irano-Turanian region, “Al-Adasiyyah”, contains mainly phenylpropanoids (30.6%), monoterpenes (24.9%) and sesquiterpenes (21.2%). In Sample1, the most representative constituents were sabinene (21.5%), cis-chrysanthenyl acetate (20.8%), germacrene D (9.3%) and myristicin (5.9%), while in sample 2, myristicin (24.1%), sclareoloxide (6.3%), and germacrene D (5.7%) were main constituents. The rate of oxygenated derivatives in the Irano-Turanian sample was higher than the Mediterranean sample. Myristicin is an unusual constituent of Salvia species.
A New Eudesmane Sesquiterpene from Dichrocephala integrifolia
Authors: Qin Fang , Wu Yi-Bing , Guo Rui-xia , Dong Mei , Sauriol Françoise , Shi Qing-Wen , Gu Yu-Cheng , Kiyota Hiromasa
Published: March 2019

A new sesquiterpene, eudesm-11-ene-4α,7β,9β-triol, was isolated from the EtOH extract of aerial parts of Dichrocephala integrifolia. Its structure was determined on the basis of spectral analysis of 1D and 2D NMR data.
Further Characterization of Foliar Flavonoids in Crossostephium chinense and their Geographic Variation
Authors: Uehara Ayumi , Kitajima Junichi , Kokubugata Goro , Iwashina Tsukasa
Published: March 2019

Foliar flavonoids of Crossostephium chinense in Japan and Taiwan were isolated and further characterized. Eighteen flavonoid aglycones, luteolin, apigenin, hispidulin, chrysoeriol, 5,7,4′-trihydroxy-6,3′,5′-trimethoxyflavone, jaceosidin, cilsimaritin, quercetin 3-methyl ether, axillarin, chrysosplenol-D, cirsiliol, apometzgerin, 5,7,3′-trihydroxy-6,4′,5′-trimethoxyflavone, luteolin 3′,4′-dimethyl ether, cirsilineol, eupatilin, nepetin and 5,7,3′,4′-tetrahydroxy-6,5′-dimethoxyflavone, were identified by UV, 1H and 13C NMR spectroscopic, LC-MS and HPLC comparisons with authentic samples. The compounds existed on the leaf surface. Four flavonoid glycosides, quercetin 3,7-di- O-glucoside, quercetin 3- O-rutinoside, luteolin 7- O-glucoside and apigenin 7- O-rutinoside, were also isolated as the intracellular flavonoids. It was shown by HPLC survey that variation of the species’ flavonoids occurs among the collection sites.
Hawaiian Propolis: Comparative Analysis and Botanical Origin
Authors: Inui Saori , Hosoya Takahiro , Kumazawa Shigenori
Published: March 2019

Propolis is a resinous mixture of substances collected and processed from various botanical sources by honeybees ( Apis mellifera). We recently obtained Hawaiian propolis, the study of which, to our knowledge, has not been reported. The purpose of this study was to analyze the composition of Hawaiian propolis and to identify its botanical origin. A comparative analysis of Hawaiian and Okinawan propolis and of the glandular trichomes on Macaranga tanarius fruit (the botanical origin of Okinawan propolis) was performed using reversed-phase high-performance liquid chromatography coupled with high resolution-electrospray mass spectrometry. Hawaiian propolis contained nine prenylflavonoids that were also isolated from Okinawan propolis. In conclusion, we suggest that the botanical origin of Hawaiian propolis is M. tanarius, the same as that of Okinawan propolis.
In Silico Prediction of Tyrosinase and Adenylyl Cyclase Inhibitors from Natural Compounds
Authors: Fong Pedro , Tong Henry H. Y. , Chao Chi M.
Published: March 2019

Although many herbal medicines are effective in the treatment of hyperpigmentation, the potency of different constituents remains unknown. In this work, more than 20,000 herbal ingredients from 453 herbs were docked into the crystal structures of adenylyl cyclase and a human homology tyrosinase model using Surflex-Dock. These two enzymes are responsible for melanin production and inhibition of them may attain a skin-whitening effect superior to currently available agents. The essential drug properties for topical formulation of the herbal ingredients, including skin permeability, sensitization, irritation, corrosive and carcinogenic properties were predicted by Dermwin, Skin Sensitization Alerts (SSA), Skin Irritation Corrosion Rules Estimation Tool (SICRET) and Benigni/Bossa rulebase module of Toxtree. Moreover, similarity ensemble and pharmacophore mapping approaches were used to forecast other potential targets for these herbal compounds by the software, SEArch and PharmMapper. Overall, this study predicted seven compounds to have advanced drug-like properties over the well-known effective tyrosinase inhibitors, arbutin and kojic acid. These seven compounds have the highest potential for further in vitro and in vivo investigation with the aim of developing safe and high-efficacy skin-whitening agents.
Molecular Docking and Reaction Kinetic Studies of Chrysin Binding to Serum Albumin
Authors: Jiang Bingli , Zhao Anran , Miao Jianhua , Chang Pengfei , Chen Hailin , Pan Weigao , Lin Cuiwu
Published: March 2019

The binding properties of chrysin with serum albumin (SA) were investigated under physiological conditions by calorimetry, circular dichroism (CD) spectroscopy, and molecular modeling. Based on the thermodynamic data, molar reaction enthalpy, reaction order ( n) and the rate constant ( k) were calculated. The results of CD spectroscopy showed that chrysin could bind to SA and the conformation of SA did not have any high-ordered structural change. Computational mapping revealed chrysin binding to the subdomain IB in SA. The chrysin-serum albumin complex was stabilized by hydrophobic force and hydrogen bonding and the reaction was a spontaneous process.
New Chromone and Triglyceride from Cucumis melo Seeds
Authors: Ibrahim Sabrin R. M.
Published: March 2019

Re-investigation of the MeOH extract of the seeds of Cucumis melo L. var. reticulatus (Cucurbitaceae) led to the isolation of a new chromone derivative (5,7-dihydroxy-2-[2-(3-methoxy-4-hydroxyphenyl)ethyl]chromone (5) and a triglyceride (1,3-di-(6 Z,9 Z)-docosa-6,9-dienoyl-2-(6 Z) hexacos-6-enoylglycerol (1), together with three known compounds; α-spinasterol (2), stigmasta-7,22,25-trien-3-ol (3), and D:B-friedoolean-5-ene-3-β-ol (4), are reported from this species for the first time. Their structures were determined by extensive 1D (1H, 13C, and DEPT) and 2D (1H-1H COSY, HMQC, and HMBC) NMR and mass spectral measurements. Compound 5 displayed significant cytotoxic activity against L5178Y cells, with an ED50 of 5 μM. The MeOH extract and 5 showed antioxidant activity using the DPPH assay.
Five New Acylphloroglucinol Glycosides from the Leaves of Eucalyptus robusta
Authors: Guo Qian-Yi , Huang Xiao-Jun , Zhao Bing-Xin , Jian Yu-Qing , Luo Shi-Lin , Wang Ying , Ye Wen-Cai
Published: March 2019

Five new acylphloroglucinol glycosides, robustasides A-E (1–5), together with a known one (6), were isolated from the leaves of Eucalyptus robusta. The structures were elucidated on the basis of extensive spectroscopic and spectrometric analysis and chemical evidence. The absolute configuration of 1 was further determined by quantum chemical CD calculation.
Usnic acid and Triacylglycerides Production by the Cultured Lichen Mycobiont of Ramalina celastri
Authors: Fazio Alejandra T. , Adler Mónica T. , Maier Marta S.
Published: March 2019

A strain of the lichen mycobiont of Ramalina celastri, isolated from ascospores, was cultured axenically on two solid media containing high amounts of the carbon source: sucrose in MY10 and mannitol in BMRM. Usnic acid, the major cortical lichen metabolite, was produced by the colonies grown on MY10, with a very high yield (7.9%) in comparison with that in the lichen thallus. Mycelia grown on BMRM did not produce the lichen secondary metabolite and rendered triacylglycerides (8.5%) instead. Analysis by GC-MS of the fatty acid methyl esters revealed the presence of oleic, palmitic and stearic acids as the main triacylglyceride constituents. The present results highlight the impact of the culture conditions on the lichen mycobiont secondary metabolism and confirm that MY10 is a useful medium to obtain usnic acid from mycobionts in the laboratory.
Synthesis of 2-Acetyl-1,4-Dimethoxynaphthalene, A Potential Intermediate for Disubstituted Naphtho[2,3,c]pyran-5,10-dione
Authors: Chinea Kimberly , Vera Willian , Banerjee Ajoy K.
Published: March 2019

2-Acetyl-1-hydroxynaphthalene was converted into the title compound in three steps (bromination, substitution and methylation). 1-Methoxynaphthalene on bromination, substitution and acetylation, respectively, also yielded the target compound.
Isolation of the Tetrapeptide Apicidins G, H and I from the Fungus Fusarium semitectum
Authors: Suciati  , Garson Mary J.
Published: March 2019

This study reports the isolation and characterization of three new tetrapeptides, apicidins G (1), H (2) and I (3), along with the known apicidin (4), apicidin A (5), apicidin C (6), diketopiperazine 7, equisetin (8) and 7-hydroxy-2-(2-hydroxypropyl)-5-methylchromone (9). The structures of the new compounds were deduced by 2D NMR spectroscopic and MS data.
PSY-1, a Taxus chinensis var. mairei Extract, Inhibits Cancer Cell Metastasis by Interfering with MMPs
Authors: Zheng Zao-qian , Fu Ying-Ying , Li Bo-Heng , Zhang Mei-Ling , Yang Xiu-Li , Xin Chuan-wei , Shi Jia-na , Ying Yin , Huang Ping
Published: March 2019

Cancer is the most common disease worldwide, with death often occurring as a result of metastasis. Thus, interfering with metastasis has been regarded as a promising strategy to improve the current cancer treatments. However, exploration and development of novel anti-metastatic agents remains a major challenge. Recent evidence indicated that a polysaccharide isolated from Taxus yunnanensis suppressed tumor cells proliferation. With the objective of seeking bioactive extracts, we had previously isolated, purified and characterized a complex, water-soluble polysaccharides, PSY-1, from the leaves of Taxus chinensis var. mairei, and identified its anti-neoplastic effects. In this study, we focused on the effects of PSY-1 on cancer metastasis and its mechanism(s). The results illustrated that PSY-1 effectively suppressed the migration and invasion ability of the melanoma cancer cell line B16-F10, caused down-regulation of MMP-2 and MMP-9, and that the NF-κB pathway was involved in the anti-metastatic effects imposed by PSY-1.
The Essential Oil of Populus balsamifera Buds: Its Chemical Composition and Cytotoxic Activity
Authors: Piochon-Gauthier Marianne , Legault Jean , Sylvestre Muriel , Pichette André
Published: March 2019

The chemical composition of Populus balsamifera essential oils obtained from spring buds, fall buds, and young leaves were determined by GC and GC-MS analyses. The major constituent, (+)-α-bisabolol, a rare sesquiterpene, was isolated from spring oil using reverse-phase preparative HPLC. The cytotoxic activity of balsam poplar oils and isolated (+)-α-bisabolol was assessed in vitro against human lung carcinoma (A549) and colorectal adenocarcinoma (DLD-1) cell lines. Essential oils were cytotoxic with IC50 ranging from 35 to 50 μg/mL. (+)-α-Bisabolol exhibited pronounced activity (IC50 14 μg/mL) against both cancer cell lines. It also exhibited interesting cytotoxic activity (IC50 23 μg/mL) against human glioma (U251), higher than the one observed for (-)-α-bisabolol (IC50 34 μg/mL), which is known for its apoptosis-inducing effect against glioma cells.
Comparative Chemical Study and Cytotoxic Activity of Uvariodendron angustifolium Essential Oils from Benin
Authors: Noudogbessi Jean-Pierre , Gary-Bobo Magali , Adomou Aristide , Adjalian Elvis , Alitonou Guy Alain , Avlessi Félicien , Garcia Marcel , Sohounhloue Dominique C. K. , Menut Chantal
Published: March 2019

This study aimed to compare the chemical composition of volatile extracts obtained by hydrodistillation of leaves, stems, bark and roots of Uvariodendron angustifolium (Engl. & Diels) R. E. Fries. The essential oils, obtained with yields between 0.12 and 0.66%, were analyzed by GC/FID and GC/MS. A great variability in the chemical composition was observed depending on the plant part treated. The essential oils obtained from leaves and stems contained mainly neral (29.7–30.5%) and geranial (42.9–47.3%), while methyl eugenol was the major component of the volatile extracts from bark (68.3%) and roots (85.3%). Interesting cytotoxic properties of these essential oils on human breast cancer cells MCF-7 were demonstrated.
Composition of Essential Oil from Tagetes minuta and its Cytotoxic, Antioxidant and Antimicrobial Activities
Authors: Ali Nasser A. Awadh , Sharopov Farukh S. , Al-kaf Ali G. , Hill Gabrielle M. , Arnold Norbert , Al-Sokari Saeed S. , Setzer William N. , Wessjohann Ludger
Published: March 2019

The essential oil from the leaves of Tagetes minuta L., growing wild in Yemen, was obtained by hydrodistillation and analyzed by gas chromatography-mass spectrometry. A total of 28 compounds were identified representing 74.2% of total oil composition. Major components of the essential oil were ( Z)-ocimenone (15.9%), ( E)-ocimenone (34.8%), ( Z)-β-ocimene (8.3%), limonene (2.3%), ( Z)-tagetone (1.8%), dihydrotagetone (1.4%) and an unidentified dimethylvinylketone derivative (20.6%). The oil showed moderate cytotoxic activity against MCF-7 breast tumor cells, with an IC50 of 54.7 ± 6.2 μg/mL. In the DPPH radical scavenging assay, T. minuta oil showed potent antiradical activity with an IC50 value of 36 μg/mL. Antimicrobial activity was also investigated on several microorganisms, and the essential oil exhibited high activity against methicillin-resistant Staphylococcus aureus (MRSA) with an inhibition zone of 23 mm. It also exhibited remarkable antifungal activity against Candida albicans with an inhibition zone of 26 mm.
Chemical Composition of Angelica pancicii Essential Oil Determined by Liquid and Headspace GC-MS Techniques
Authors: Simonović Strahinja R. , Stankov-Jovanović Vesna P. , Mitić Violeta D. , Ilić Marija D. , Petrović Goran M. , Stojanović Gordana S.
Published: March 2019

The essential oil of the Balkan endemic species, Angelica pancicii, obtained by hydrodistillation, was analyzed by GC and GC-MS, applying the liquid injection mode. These results were compared with the chemical composition of volatiles achieved by the “headspace” injection mode, followed by GC and GC-MS (HS-GC-MS). A total of 40 compounds were identified in the essential oil (98.8% of the total oil) and 44 by HS-GC-MS (99.8% of the total oil). The most abundant class of compounds in both cases was monoterpenoids, which formed 92.7% of the essential oil (97.7% by HS-GC-MS) of total identified compounds. The major components in both cases were β-phellandrene (54.9% and 60.1%, respectively), α-pinene (14.5% and 20.1%, respectively) and α-phellandrene (4.5% and 4.3%, respectively).
Chemical Description and Essential Oil Yield Variability of Different Accessions of Salvia lavandulifolia
Authors: Usano-Alemany Jaime , Palá-Paúl Jesús , Rodríguez Manuel Santa-Cruz , Herraiz-Peñalver David
Published: March 2019

The amount and chemical composition of essential oils are crucial for the modulation of the flavor, scent and therapeutic properties of aromatic and medicinal plants. The aim of this study was to evaluate the effects of phenology and weather conditions on the essential oil yield obtained from the aerial parts of Salvia lavandulifolia Vahl. Besides, we tried to carry out an approach to the chemical composition at the time of full bloom. Essential oil production of several accessions was monitored throughout the whole phenological cycle, both, at the original location growing wild and at the experimental plot as cultivated plants. Local pedoclimatic conditions seem to be crucial for the plant essential oil production. Our results showed high conditioning rates from both yearly climatic conditions and developmental stage of the plants. Maximum yield production was reported at the full seed maturation stage (average 1.74%) and after a slight dry period (average 2.16%). Phytochemical differences were maintained when plants were forced to grow under common pedoclimatic conditions. Thereby, essential oil analysis showed some populations formed by clearly distinct individuals while others had more homogenous plants. Compounds such α-pinene, β-pinene + myrcene, limonene, 1,8-cineol, camphor and β-caryophyllene were the main compounds of the essential oils of S. lavandulifolia.
In vitro Antibacterial Activity of Libanotis montana Essential Oil in Combination with Conventional Antibiotics
Authors: Miladinović Dragoljub L. , Ilić Budimir S. , Mihajilov-Krstev Tatjana M. , Jović Jovana L. , Marković Marija S.
Published: March 2019

The chemical composition and antibacterial activity were examined of Libanotis montana Crantz subsp. leiocarpa (Heuff.) Soó. (Apiaceae) essential oil. Gas chromatography and gas chromatography/mass spectrometry were used to analyze the chemical composition of the oil. The antibacterial activity was investigated by the broth microdilution method against thirteen bacterial strains. The interactions of the essential oil and three standard antibiotics: tetracycline, streptomycin and chloramphenicol toward five selected strains were evaluated using the microdilution checkerboard assay in combination with chemometric methods: principal components analysis and hierarchical cluster analysis. Sesquiterpene hydrocarbons were the most abundant compound class in the oil (67.2%), with β-elemene (40.4%) as the major compound. The essential oil exhibited slight antibacterial activity against the tested bacterial strains in vitro, but the combinations L. montana oil-chloramphenicol and L. montana oil-tetracycline exhibited mostly either synergistic or additive interactions. These combinations reduced the minimum effective dose of the antibiotics and, consequently, minimized their adverse side effects. In contrast, the association of L. montana essential oil and streptomycin was characterized by strong antagonistic interactions against Escherichia coli ATCC 25922. In the PCA and HCA analyses, streptomycin stood out and formed a separate group.
Simple and Short Synthesis of Trans-(R)-Nerolidol, a Pheromone Component of Fruit Spotting Bug
Authors: Le Thanh C. , Chauhan Kamlesh R.
Published: March 2019

A three-step synthesis of enantiomerically pure ( R) and ( S)- trans nerolidol from commercially available E, E-fanesol is described. Trans nerolidol is an abundant sesquiterpene in many plant species, almost enantiomerically pure; however, the configuration of chirality is S. There is no natural resource for R-trans nerolidol, which has recently been identified as a pheromone component of the fruit spotting bug Amblypelta lutescens. The simple syntheses reported here will make enantiomerically pure R- and S-trans nerolidol and homologues available for further research and ultimately for use in integrated pest management strategies comprising pheromones.
Monoterpene Citral Derivatives as Potential Antimalarials
Authors: Singh Soni , Khandare Reena P. , Sharma Manish , Bhasin Virendra K. , Bhat Sujata V.
Published: March 2019

Conjugated acid derivatives containing nitrogen have been synthesized from the simple acyclic monoterpene citral, using various reactions, including Wittig, Baylis Hillman, amide and ester condensations. Similarly, amine peroxides were synthesized by subjecting citral to Mannich type reaction with amines and t-butyl hydroperoxide. Molecules 3–10 were evaluated for antimalarial activity against erythrocytic stages of chloroquine sensitive P. falciparum strain 3D7. Four derivatives displayed interesting activity with an IC50< 2.5 μM, and warrant further investigations.
Chemotaxonomic Value of Magastigmane Glucosides of Cichorium calvum
Authors: Michalska Klaudia , Beharav Alex , Kisiel Wanda
Published: March 2019

Morphological characters and molecular analyses of Cichorium calvum and C. pumilum do not allow clear discrimination between these closely related wild species. Therefore, the aim of this study was to characterize the secondary metabolites of C. calvum and to select chemical markers which are unique to this species. From roots of C. calvum, ten sesquiterpene lactones were isolated, including seven lactucin-type guaianolides reported earlier from C. pumilum. Aerial parts also afforded secondary metabolites common to both species, along with the megastigmane glucosides staphylionoside D, saussureoside B and komaroveside A. This is the first report of the occurrence of these norisoprenoids in Cichorium species and the second record of their isolation from plants. Therefore, chemical discrimination of C. calvum is possible on the basis of its norisoprenoid composition.
Anti-influenza Sesquiterpene from the Roots of Reynoutria japonica
Authors: Nhiem Nguyen Xuan , Van Kiem Phan , Van Minh Chau , Hoai Nguyen Thi , Duc Ho Viet , Tai Bui Huu , Quang Tran Hong , Le Tuan Anh Hoang , Yeo Sang-Gu , Song Jae-Hyoung , Cheon Doo-Sung , Park Moon Ho , Ko Hyun-Jeong , Kim Seung Hyun
Published: March 2019

One new flavonol glycoside, 4′- O-methylmyricitrin 3′- O-β-D-glucopyranoside (1), one new sesquiterpene, reynoudiol (11), as well as the 12 known compounds (2–10, 12–14) quercetin 3- O-methyl ether (2), quercitrin (3), isorhamnetin 3- α-L-rhamnopyranoside (4), tamarixetin 3- α-L-rhamnopyranoside (5), myricitrin (6), 4′- O-methylmyricitrin (7), isorhamnetin 3- O-β-D-xylopyranosyl (1→2)- O-β-D-glucopyranoside (8), isorhamnetin 3- O-β-D-apiofuranosyl-(1→2)- O-β-D-glucopyranoside (9), (+)-catechin (10), 7-drimene-3,11,12-triol (12), clovane-2 β,9 α-diol (13), and α-cadinol (14), were isolated from the methanol extract of Reynoutria japonica roots. Based on in vitro screening of the anti-influenza activity of the isolated compounds, reynoudiol showed significantly higher activity than that of oseltamivir phosphate at the same concentration, and did not induce any detectable cytopathic effect in MDCK cells. The CC50 of reynoudiol was above 50 μM and could inhibit influenza virus infection with an IC50 of 0.29 ± 0.01 μM. The therapeutic index (TI) of reynoudiol against influenza infection was 172.4, and thus, this compound can be potentially used to treat oseltamivir-resistant influenza virus infection.
Laurane-, Cyclolaurane-, and Cuparane-type Sesquiterpenes from the Marine Red Alga Laurencia okamurai
Authors: Liang Yi , Li Xiao-Ming , Li Chun-Shun , Sun Hong , Wang Bin-Gui
Published: March 2019

Chemical investigation of the secondary metabolites extracted from the marine red alga Laurencia okamurai has resulted in the isolation of one new (lauramurin, 1) and six known (2–7) sesquiterpenes. On the basis of the data obtained by our detailed spectroscopic analysis as well as by comparison with those reported, the structures of these compounds were elucidated as four laurane sesquiterpenes including lauramurin (1), laur-11-en-10-ol (2), aplysinol (3), and debromoaplysinol (4), two cyclolaurane sesquiterpenes laurequinone (5) and laurentristich-4-ol (6), and one cuparane ether sesquiterpene (7). The antibacterial activity against Staphylococcus aureus and brine shrimp ( Artemia salina) lethality for the isolated compounds were evaluated. Compounds 2 and 5–7 displayed moderate lethality against brine shrimp.
Facile Access to Optically Active Ring C Aromatic Diterpene Derivatives from (+)-Manool. First Synthesis of 13,14-Dihydroxy-8,11,13-podocarpatrien-7-one
Authors: Nóvoa María L. , Salazar Franklin J. , Gámez Carlos , Angarita Ana Y. , Tropper Eleonora , Canudas Nieves , Villamizar José E.
Published: March 2019

14,15,17-Trinorlabdan-8,13-dione 6 was efficiently synthesized via ozonolysis of (+)-manool (4) followed by treatment with aqueous NaOH in the presence of tetra- n-butylammonium bromide as catalyst. This protocol has the advantages of high yield, mild conditions and simple procedure. Utilizing this strategy, the first enantiospecific synthesis of 13,14-dihydroxy-8,11,13-podocarpatrien-7-one (1), a constituent of Taiwania cryptomerioides and Celastrus paniculatus, was achieved starting from (+)-manool (4) after a four-step sequence in 24% overall yield.
T-DNA Insertion Alters the Terpenoid Content Composition and Bioactivity of Transgenic Artemisia annua
Authors: Karaket Netiya , Wiyakrutta Suthep , Lacaille-Dubois Marie-Aleth , Supaibulwatana Kanyaratt
Published: March 2019

In this study, the interference of T-DNA insertion upon Agrobacterium-mediated transformation on the biochemical expression of the host genome is discussed. Plant extracts of transgenic Artemisia annua L. with or without an overexpressed farnesyl pyrophosphate synthase gene have been investigated for their bioactivity and metabolic profile in comparison with wild type A. annua. The highest antimicrobial activity against Staphylococcus aureus, Bacillus subtilis and Candida albicans was observed in the T253 transgenic lines. Moreover, the crude extract from T253 showed higher antimalarial activity against the Plasmodium faciparum K1 strain than those of the others. The terpenoid constituents and antimicrobial properties of the plant samples were grouped by hierarchical clustering analysis. The clustering showed that squalene is a putative compound that might be involved in increasing the bioactivity of the transgenic line. In addition, T253 had a triterpene content that was about twice as great as that of the T253-2 line, which had a higher content of sesquiterpenes. However, both lines were transformed by the same FPS gene. These results suggested that the different bioactive properties observed in each transgenic line may be caused by variations in their terpenoid composition, which is affected by T-DNA insertion at different positions in the host plant.