bluuebunny/crossref_metadata_2025 huggingface dataset:
Quinolizidine Alkaloids from Sophora velutina subsp. zimbabweensis (Fabaceae: Sophoreae)
Authors: Korir Erick , Kiplimo Joyce J. , Crouch Neil R. , Moodley Nivan , Koorbanally Neil A.
Published: March 2019

Three novel quinolizidine alkaloids, N-methylenehydroxycytisine (1), 6,7-dihydroxylupanine (2), and velutinine (3) have been isolated from the fruits and pods (1 and 2) and stem bark (3) of Sophora velutina subsp. zimbabweensis along with the known quinolizidine alkaloids, 7-hydroxylupanine (4), thermopsine (5), N-methylcytisine (6), cytisine (7), an aromatic ester, methyl-3-(3′,4′-dimethoxyphenyl)-2-propenoate (8) and the triterpenoids, lup-20(29)-ene-3β-ol (9) and 12-oleanen-3-one (10). Compounds 6 and 10 showed good antibacterial activity against E. faecalis, with MIC values of 20.8 and 10.9 μg mL−1, respectively. The other compounds tested exhibited low to moderate antibacterial activity.
The Inhibitory Effects of Representative Chalcones Contained in Angelica keiskei on Melanin Biosynthesis in B16 Melanoma Cells
Authors: Arung Enos Tangke , Furuta Shoko , Sugamoto Kazuhiro , Shimizu Kuniyoshi , Ishikawa Hiroya , Matsushita Yoh-ichi , Kondo Ryuichiro
Published: March 2019

In our effort to find new whitening agents, we evaluated the effects of representative chalcones [4-hydroxyderricin (1), xanthoangelol (2), xanthoangelol H (3), deoxyxanthoangelol H (4), and deoxydihydroxanthoangelol H (5)] contained in the stem of Angelica keiskei on tyrosinase and melanin formation in B16 melanoma cells. In addition, the antioxidant effects of these chalcones in ORAC and DPPH assays were also determined. Interestingly, all chalcones (1–5) inhibit melanin formation in B16 melanoma cells, with low cytotoxicity.
Antioxidant and Anti-cholinesterase Activity of Globularia meridionalis Extracts and Isolated Constituents
Authors: Tundis Rosa , Bonesi Marco , Menichini Federica , Loizzo Monica R. , Conforti Filomena , Statti Giancarlo , Pirisi Filippo M. , Menichini Francesco
Published: March 2019

The antioxidant and anti-cholinesterase properties of Globularia meridional (Podp.) O. Schwarz (Globulariaceae) were investigated. G. meridionalis aerial parts and roots were extracted with methanol, and the total extract successively partitioned with n-hexane. The methanol fraction of the roots showed the highest antioxidant activity with IC50 values of 8.0 and 2.1 μg/mL in the DPPH and β-carotene bleaching tests, respectively. From this fraction, three flavonoids, namely pectolinarigenin 7- O-β-glucoside, apigenin 7- O-β-glucoside and luteolin, and two phenylethanoids, namely acteoside and isoacteoside, were isolated. Potential anti-cholinesterase effects were assessed through the acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes inhibition assay. The n-hexane fraction of the roots exhibited the highest activity against both AChE and BChE with IC50 values of 65.5 and 70.4 μg/mL, respectively.
Antioxidant Activities and Total Phenolic and Flavonoid Contents in Three Indigenous Medicinal Vegetables of North-east India
Authors: Handique Jyotirekha G. , Boruah Manas Pratim , Kalita Dipika
Published: March 2019

Antioxidant activities of the n-hexane, ethyl acetate and methanol extracts of three indigenous leafy vegetables of North East India viz., Polygonum microcephallum, Oxalis corniculata and Portulaca oleraceae were measured by spectroscopic methods using the 1, 1- diphenyl-2-picrylhydrazyl (DPPH•) radical assay and xanthine/xanthine oxidase assay. The total phenolic and total flavonoid contents of each extract were also measured to assess their effect on the antioxidant activity. It was observed that the methanol extracts of all the species showed the highest antioxidant activities and high values for total phenolic and flavonoid contents. A strong correlation between the antioxidant activities and the total phenolic content was observed for the three vegetables. It indicates that phenolics are one of the main components responsible for the antioxidant behavior of vegetables. HPLC analysis showed the presence of a number of identified phenolic compounds.
Synthesis and Biological Evaluation of Combretastatin A-4 and Three Combretastatin-Based Hybrids
Authors: González Miguel A. , Pérez-Guaita David , Agudelo-Goméz Lee S. , Tangarife-Castaño Verónica , Zapata Bibiana , Betancur-Galvis Liliana
Published: March 2019

The syntheses of combretastatin A-4 from gallic acid and of three combretastatin-based hybrids are described. Starting from commercial gallic acid, the phosphonium salt (3,4,5-trimethoxybenzylphosphonium bromide) is synthesized and coupled, through a Wittig reaction, with several aldehydes, including methoxymethyl-protected isovanillin, the aldehyde γ-bicyclohomofarnesal having a labdane skeleton, 3-(3-pyridyl) propanal, and furfural. The biological properties of the cis-coupled compounds as cytotoxic, antiviral and antifungal agents are also reported. In addition, pyrogallol, gallic and 3,4,5-trimethoxybenzoic acids have been studied biologically.
Quantitative Analysis of Fructo-oligosaccharides in Gynura divaricata subsp. formosana by High Performance Anion Exchange Chromatography-Pulsed Amperometric Detection
Authors: Chou Shen-Chieh , Lee Shoei-Sheng
Published: March 2019

High performance anion exchange chromatography-pulsed amperometric detection was employed in this study to conduct quantitative analysis of the inulin-related fructo-oligosaccharides present in Gynura divaricata subsp. formosana. Result obtained for the 1-kestose (GF2), nystose (GF3) and 1F-β-fructofuranosyl-nystose (GF4) contents were 146.60 ± 0.04, 24.70 ± 0.75 and 16.60 ± 0.91 μg/g, fresh weight, and 68.90 ± 0.02, 7.60 ± 1.34 and 149.30 ± 0.06 μg/g (mean ± RSD), dry weight, respectively. Using this method, the limit of quantitation was 20 μg/mL and the linear detectability between 0-250 μg/mL. The developed method provides a practical analysis for these low caloric value, prebiotic and non-digestible carbohydrates in the genus Gynura.
Polyketide Metabolites from the Endophytic Fungus Microdiplodia sp. KS 75-1
Authors: Shiono Yoshihito , Hatakeyama Taiji , Murayama Tetsuya , Koseki Takuya
Published: March 2019

Through our screening for new natural compounds, four new polyketide metabolites, 7,8-dihydonivefuranone A (1), 6(7)-dehydro-8-hydroxyterrefuranone (2), 8-hydroxyterrefuranone (3), and 6-hydroxyterrefuranone (4) were isolated from the fermentation extract of Microdiplodia sp. KS 75–1, together with the known compounds nivefuranones A (5) and B (6); their structures were determined by spectroscopic (NMR, UV and IR) and MS analysis.. Compounds 1, 2, 4 and 5 showed antimicrobial activity against Candida albicans and Staphylococcus aureus.
Muscone Exerts Neuroprotection in an Experimental Model of Stroke via Inhibition of the Fas Pathway
Authors: Wei Gang , Chen Dong-Feng , Lai Xiao-Ping , Liu Dong-Hui , Deng Ru-Dong , Zhou Jian-Hong , Zhang Sai-Xia , Li Yi-Wei , Li Hui , Zhang Qiong-Dan
Published: March 2019

Identifying small molecules that are neuroprotective against stroke injury will be highly beneficial for treatment therapies. A cell viability assay and gas chromatography-mass spectrometry were used to identify active small molecules in XingNaoJing, which is a well known Chinese Medicine prescribed for the effective treatment of stroke. Studies have found that muscone is the active compound that prevents PC12 cell and cortical neuron damage following various injuries. Analysis of apoptosis indicated that muscone inhibited glutamate-induced apoptotic cell death of PC12 cells and cortical neurons. Fas and caspase-8 expression were upregulated following glutamate treatment in cortical neurons, and was markedly attenuated in the presence of muscone. Furthermore, muscone significantly reduced cerebral infarct volume, neurological dysfunction and inhibited cortical neuron apoptosis in middle cerebral artery occluded (MCAO) rats in a dose-dependent manner. Moreover, a significant decrease in Fas and caspase-8 expression in the rat cortex was observed in MCAO rats treated with muscone. Our results demonstrate that muscone may be a small active molecule with neuroprotective properties, and that inhibition of apoptosis and Fas is an important mechanism of neuroprotection by muscone. These findings suggest a potential therapeutic role for muscone in the treatment of stroke.
Variation in the Volatile Constituents of Different Plant Parts of Ligusticopsis wallichiana from Western Himalaya, India
Authors: Padalia Rajendra C. , Verma Ram S. , Chauhan Amit , Chanotiya Chandan S. , Yadav Anju
Published: March 2019

The essential oil composition of the leaves, stem, flowers and roots of Ligusticopsis wallichiana (DC.) Pimenov & Kljuykov were analyzed by GC-FID and GC-MS methods. Forty-five constituents, forming 93.2%–97.8% of the oil compositions, were dominated by acetylenic (31.5%–92.8%) compounds and sesquiterpenoids (0.3%–44.4%). The leaf essential oil was mainly composed 3,5-nonadiyne (35.8%), β-selinene (20.9%), α-funebrene (10.1%) and ( Z)-falcarinol (6.1%). The stem oil was dominated by acetylenic compounds (73.8%) represented by 3,5-nonadiyne (67.8%) and ( Z)-falcarinol (5.7%). On the contrary, the major components of the flower essential oil were sesquiterpenoids (37.5%), such as germacrene D (16.6%), α-funebrene (7.4%), and acetylenic compounds (31.5%), such as ( Z)-falcarinol (21.0%) and 3,5-nonadiyne (10.0%). Monoterpenoids constituted 23.9% of the flower oil with limonene (19.9%) as the single major constituent. The essential oil of the roots was dominated by 3,5-nonadiyne (90.5%). The results showed considerable qualitative and quantitative variations in the essential oil compositions of the different plant parts of L. wallichiana. ( Z)-Falcarinol (1.9%–21.0%) and α-funebrene (0.1%–10.1%) were reported for the first time from the essential oils of L. wallichiana.
Chemical Composition of the Essential Oils of Centaurea formanekii and C. orphanidea ssp. thessala, Growing Wild in Greece
Authors: Jemia Mariem Ben , Formisano Carmen , Bancheva Svetlana , Bruno Maurizio , Senatore Felice
Published: March 2019

The volatile constituents of the aerial parts of Centaurea formanekii Halacsy and the aerial parts, capitula and roots of C. orphanidea Heldr. & Sart. ex Boiss. ssp. thessala (Hausskn.) Dostál from Greece were extracted by hydrodistillation and analyzed. The main components in C. formanekii were hexadecanoic acid (13.6%), δ-elemene (9.1%), and spathulenol (6.9%). The main components in C. orphanidea ssp. thessala were γ-elemene (26.1%) and caryophyllene oxide (13.2%) in the aerial parts, hexadecanoic acid (33.5%) and heptacosane (6.3%) in the capitula, and hexadecanoic acid methyl ester (22.0%) and α-chamigrene (14.0%) in the roots. The chemotaxonomic significance with respect to other previously studied species of the same sections (Phalolepis and Achrolopus, respectively) is discussed.
Chemical Composition, Antimicrobial, Antioxidant and Cytotoxic Activity of Essential Oils of Plectranthus cylindraceus and Meriandra benghalensis from Yemen
Authors: Ali Nasser A. Awadh , Wurster Martina , Denkert Annika , Arnold Norbert , Fadail Iman , Al-Didamony Gamal , Lindequist Ulrike , Wessjohann Ludger , Setzer William N.
Published: March 2019

The chemical composition, antimicrobial, antioxidant and cytotoxic activities of the essential oils isolated from the leaves of Plectranthus cylindraceus Hoechst. ex. Benth. (EOPC) and Meriandra benghalensis (Roxb.) Benth. (EOMB) were investigated. Sixteen compounds were identified in P. cylindraceus oil representing 94.5% of the oil content with thymol (68.5%), terpinolene (5.3%), β-selinene (4.7%), β-caryophyllene (4.0%), δ-cadinol (2.1%), and ar-curcumene (1.7%) as the major compounds. In M. benghalensis oil, 12 compounds were identified, which made up 82.0% of the total oil. The most abundant constituents were camphor (43.6%), 1,8-cineole (10.7%), α-eudesmol (5.8%), caryophyllene oxide (5.8%), camphene (5.3%) and borneol (3.4%). The antimicrobial activities of both oils were evaluated against five microorganisms with the disc diffusion test, the broth micro-dilution method and a semiquantitative bioautographic test. The most sensitive microorganisms for P. cylindraceus oil were S. aureus, B. subtilis, and C. albicans with inhibition zones of 38, 42, and 43 mm and MIC values of 0.39, 0.18, and, 0.18 μL/mL, respectively. M. benghalensis oil showed weak to moderate activity against the tested microorganisms. 2,2-Diphenyl-1-picrylhydrazyl (DPPH) assay was employed to study the potential antioxidant activities of both oils. The antioxidant activity of P. cylindraceus oil (IC50 34.5 μg/mL) appeared to be higher than that of M. benghalensis oil (IC50 935 μg/mL). At a concentration of 100 μg/mL, EOMB showed a stronger cytotoxic activity, with growth inhibition of 71% against HT29 tumor cells, than EOPC (18%).
Analytical Profiling of Bioactive Constituents from Herbal Products, using Metabolomics - A Review
Authors: Satheeshkumar Nanjappan , Nisha Narayanan , Sonali Nirmal , Nirmal Jayabalan , Jain Gaurav K. , Spandana Vudataneni
Published: March 2019

Natural products have been the source of many active substances in drug discovery. There are several strategies/approaches in the field of biology, drug discovery, molecular and cell biology for identification of bioactive molecules. Metabolomics involves fewer complexities, is more precise and provides more relevant data compared with other techniques. This approach is based on the application of new technologies and provides real-world end points that complement and help in the interpretation of genomic and proteomic data in drug discovery. It has also been proven to be a valuable analytical tool for the identification of secondary metabolites from medicinal plants, particularly for evidence-based development of new phytotherapeutical agents and nutra-ceuticals. This review outlines the different analytical techniques used to detect and measure the multiplexed metabolites and biomarkers in the herbal field.
Antiparasitic and Anticancer Carvotacetone Derivatives of Sphaeranthus bullatus
Authors: Machumi Francis , Yenesew Abiy , Midiwo Jacob O. , Heydenreich Matthias , Kleinpeter Erich , Tekwani Babu L. , Khan Shabana I. , Walker Larry A. , Muhammad Ilias
Published: March 2019

The CH2Cl2-MeOH (1:1) extract of the aerial parts of Sphaeranthus bullatus, an annual herb native to tropical East Africa, showed activity against chloroquine sensitive D6 (IC50 9.7 μg/mL) and chloroquine resistant W2 (IC50 15.0 μg/mL) strains of Plasmodium falciparum. Seventeen secondary metabolites were isolated from the extract through conventional chromatographic techniques and identified using various spectroscopic methods. The compounds were evaluated for their in vitro antiplasmodial, antileishmanial and anticancer activities revealing activity of four carvotacetone derivatives, namely 3-acetoxy-7-hydroxy-5-tigloyloxycarvotacetone (1), 3,7-dihydroxy-5-tigloyloxycarvotacetone (2), 3-acetoxy-5,7-dihydroxycarvotacetone (3) and 3,5,7-trihydroxy-carvotacetone (4); with antiplasmodial IC50 values of 1.40, 0.79, 0.60 and 3.40 μg/mL, respectively, against chloroquine sensitive D6 strains of P. falciparum; antiplasmodial activity of IC50 2.00, 0.90, 0.68 and 2.80 μg/mL, respectively, against chloroquine resistant W2 strains of P. falciparum; antileishmanial IC50 values of 0.70, 3.00, 0.70 and 17.00 μg/mL, respectively, against the parasite L. donovanii promastigotes, and anticancer activity against human SK-MEL, KB, BT-549 and SK-OV-3 tumor cells, with IC50 values between <1.1 - 5.3 μg/mL for 1-3. In addition, cytotoxic effects of the active compounds were evaluated against monkey kidney fibroblasts (VERO) and pig kidney epithelial cells (LLC-PK11). The structures of carvotacetone derivatives were determined by 1D and 2D NMR spectroscopy; the absolute stereochemical configuration of 3-acetoxy-7-hydroxy-5-tigloyloxycarvotacetone (1) was determined as 3 R, 4 R, 5 S by circular dichroism, specific rotation, 1H NMR and 2D NMR ROESY and NOESY experiments.
Sesquiterpenes from Onopordum illyricum and their Antifeedant Activity
Authors: Rosselli Sergio , Maggio Antonella Maria , Canzoneri Marisa , Simmonds Monique S. J. , Bruno Maurizio
Published: March 2019

Phytochemical investigation of the acetone extract of the aerial parts of Onopordum illyricum L. afforded five known sesquiterpenoids: compounds 3 and 4 already isolated from O. illirycum, and 8α-[4′-hydroxymethacryloyloxy]-sonchucarpolide (1), 8α-[4′-hydroxymethacryloyloxy]-4-epi-sonchucarpolide (2) and 8-(4′-hydroxymethacryloyl)-dehydromelitensin (5), not previously detected in this species. Compounds 4 and 5 showed moderate antifeedant activity against larvae of Spodoptera littoralis.
Characterization of Yew Tree (Taxus) Varieties by Fingerprint and Principal Component Analyses
Authors: Truus Kalle , Vaher Merike , Borissova Maria , Robal Marju , Levandi Tuuli , Tuvikene Rando , Toomik Peeter , Kaljurand Mihkel
Published: March 2019

The composition of varieties of Taxus growing in Estonia was analyzed by capillary electrophoresis with diode array detection (CE-DAD) for the separation of phenolic compounds, and by high performance liquid chromatography-mass spectrometry (HPLC-MS) for the determination of taxoids. The main purpose of this study was the chemotaxonomic differentiation of varieties of Taxus by using data from these analyses. Fingerprints scanned at 214 nm on the basis of CE separation at pH 9.3 were used to characterize seven varieties of yew. The contents of four key taxoids (10-deacetylbaccatin, baccatin III, cephalomannine and paclitaxel) in six Taxus varieties were comparatively determined by HPLC-MS. The set of electropherograms/chromatograms of the various Taxus extracts were subjected to principal component analysis (PCA), using the peak areas of 16 phenolic compounds and 14 taxoids as characteristics. The formation of distinct clusters in accordance with botanical classification proves the suitability of PCA for differentiating varieties of Taxus.
Identification of Triterpenes from Milkweed (Asclepias syriaca)
Authors: Háznagy-Radnai Erzsébet , Wéber Edit , Czigle Szilvia , Máthé Imre
Published: March 2019

The chloroform extract of Asclepias syriaca stem were investigated. Three triterpenes were isolated by TLC, VLC, and preparative chromatography, and their structures established by one and two-dimensional NMR spectroscopy. Lupenyl acetate has been isolated for the first time from A. syriaca; this is the first representative of a triterpene bearing a lupane skeleton in this species. In addition, α-amyrin acetate and α-amyrin butyrate were isolated.
Evaluation of the Anti-angiogenic Activity of Saponins from Maesa lanceolata by Different Assays
Authors: Foubert Kenn , Breynaert Annelies , Theunis Mart , Van Den Bossche Rita , De Meyer Guido R.Y. , Van Daele André , Faizal Ahmad , Goossens Alain , Geelen Danny , Conway Edward M. , Vlietinck Arnold , Pieters Luc , Apers Sandra
Published: March 2019

Angiogenesis, in which a vascular network is established from pre-existing vessels, is a complex multistep process. Mechanisms underlying angiogenesis can be investigated using a variety of in vitro, ex vivo and in vivo approaches. Evaluation of several promising plants and plant metabolites, including terpenoids, revealed promising anti-angiogenic activity. Since the maesasaponins displayed anti-angiogenic activity in the chick chorioallantoic membrane (CAM) assay, their activity was further investigated in several test systems. The rat aorta ring assay was compared with the placental vein assay and then selected for the ex vivo investigation of the saponins. Besides their effect on the viability of HUVEC, the anti-angiogenic capacity of the compounds was also investigated in an in vivo zebrafish assay. The activity of the saponins in the viability assay was more pronounced than in the rat aorta ring assay and similar to the effect observed in the CAM assay. The use of different test systems, however, implies different results in the case of saponins.
Conversion of Protopanaxadiol Type Saponins to Ginsenoside Rg3 by Lemon
Authors: Sun Cheng-Peng , Gao Wei-Ping , Zhao Bao-Zhong , Cheng Le-Qin
Published: March 2019

The ability of fresh lemon ( Citrus limon) to convert protopanaxadiol-type saponins into ginsenoside Rg3 was investigated, and the structures of 20( S)-ginsenoside Rg3 (1) and 20( R)-ginsenoside Rg3 (2) were identified by 1H NMR and 13C NMR spectroscopy. The experiment showed that lemon possesses the strong ability to hydrolyze ginsenosides. When protopanaxadiol-type saponins (16 mg/mL) were hydrolyzed by fresh lemon juice at 80°C for 3 hrs, the conversion ratios of ginsenoside Rb1, Rb2, Rc and Rd were 92.9%, 90.0%, 96.9% and 55.5%, respectively, and the yields of 20( S)-ginsenoside Rg3 and 20( R)-ginsenoside Rg3 were, respectively, 31.2% and 28.3%.
Osteoclastogenesis Inhibitory Effect of Ergosterol Peroxide Isolated from Pleurotus eryngii
Authors: Yokoyama Satoru , Bang Tran Hai , Shimizu Kuniyoshi , Kondo Ryuichiro
Published: March 2019

Ergosterol peroxide was isolated from the ethanol extract of Pleurotus eryngii as an inhibitor of osteoclast differentiation. This compound showed an inhibitory effect in a dose-dependent manner and an inhibition rate of up to 62% with low cytotoxicity, even at a concentration as low as 1.0 μg/mL.
A Novel Sterol Sulfate and New Oligosaccharide Polyester from the Aerial Parts of Polygala sibirica
Authors: Song Yue Lin , Zhou Si Xiang , Wei He Lin , Jiang Yong , Tu Peng Fei
Published: March 2019

Polygalasterol A (1), a new sterol sulfate, and a new oligosaccharide ester, polygalasibiricose I (2), have been isolated from the n-butanol soluble fraction of the aerial parts of Polygala sibirica L.. Their structures were determined to be (24 R)-24-sulfo-5 α-cholestane-3 α,7 α,12 α,24-tetrol (1) and 3- O-benzoyl- β-D-fructofuranosyl-(2→1)-[ β-D-glucopyranosyl-(1→2)]-4- O-{4- O-[3- O-[3- O-benzoyl-(2- O-acetyl)- α-L-rhamnopyranosyl-(1→3)]-2- O-acetyl- α-L-rhamnopyranosyl]-( Z)- p-coumaroyl} -α-D-glucopyranoside (2), respectively, by HRESIMS, and 1D and 2D NMR spectroscopic studies.
Antifungal Activity of Hydrochloride Salts of Tylophorinidine and Tylophorinine
Authors: Dhiman Mini , Parab Rajashri R. , Manju Sreedharannair L. , Desai Dattatraya C. , Mahajan Girish B.
Published: March 2019

The antimicrobial efficacy of two phenanthroindolizidine alkaloids, tylophorinidine hydrochloride (TdnH) and tylophorinine hydrochloride (TnnH), isolated from the plant Tylophora indica (local name, Antamul) was evaluated. These were screened for in vitro antifungal and antibacterial activities. Both compounds exhibited potent antifungal activity displaying minimum inhibitory concentrations (MIC) in the range of 2-4 μg/mL for TdnH and 0.6-2.5 μg/mL for TnnH against Candida species.
Evaluation of Antibacterial and Anti-biofilm Activities of Cinchona Alkaloid Derivatives against Staphylococcus aureus
Authors: Skogman Malena E. , Kujala Janni , Busygin Igor , Leino Reko , Vuorela Pia M. , Fallarero Adyary
Published: March 2019

Bacterial biofilms are resistant to most of the commonly available antibacterial chemotherapies. Thus, an enormous need exists to meet the demands of effective anti-biofilm therapy. In this study, a small library of cinchona alkaloids, including the naturally occurring compounds cinchonidine and cinchonine, as well as various synthetic derivatives and analogues was screened for antibacterial and anti-biofilm activity against the Staphylococcus aureus biofilm producing strain ATCC 25923. Two methods were used to evaluate activity against biofilms, namely crystal violet staining to measure biomass and resazurin assay to measure biofilms viability. Cinchonidine was found to be inactive, whereas a synthetic derivative, 11-triphenylsilyl-10,11-dihydrocinchonidine (11-TPSCD), was effective against planktonic bacteria as well as in preventing biofilm formation at low micromolar concentrations. Higher concentrations were required to eradicate mature biofilms.
Simultaneous Determination of Alkaloids and Flavonoids from Aerial Parts of Passiflora Species and Dietary Supplements using UPLC-UV-MS and HPTLC
Authors: Avula Bharathi , Wang Yan-Hong , Rumalla Chidananda Swamy , Smillie Troy J. , Khan Ikhlas A.
Published: March 2019

A rapid UPLC method was developed for the simultaneous analysis of five indole alkaloids (harmalol, harmol, harmane, harmaline and harmine) and four flavonoids (orientin, isoorientin, vitexin, and isovitexin) from the aerial parts of Passiflora incarnata L. (Passifloraceae), other species of Passiflora (P. violacea Vell., P. edulis Sims., P. suberosa L., P. morifolia Mast. and P. quadrangularis L.), Peganum harmala, and dietary supplements that claim to contain Passiflora. The separation was achieved within eight minutes by using C-18 column, a water/acetonitrile mobile phase, both containing formic acid, using a gradient system and a temperature of 35°C. The method was validated for linearity, repeatability, limits of detection (LOD), and limits of quantification (LOQ). The wavelength used for quantification with the diode array detector was 340 nm for flavonoids and alkaloids. The developed method is simple, economic, fast and especially suitable for quality control analysis of flavonoids and alkaloids in plant samples and dietary supplements. The compounds (including isoschaftoside and schaftoside) in plant samples and commercial products of Passiflora were identified and confirmed by UPLC-MS. A HPTLC method was also developed for the chemical fingerprint analysis of Passiflora samples.
Simultaneous Determination of Four Major Constituents of Semen Vaccariae Using HPLC-DAD
Authors: Zhang Haijiang , Yao Wei , Chen Yunyun , He Peipei , Chen Yao , Chen Peipei , Han Jia , Li Xiaoyu
Published: March 2019

A simple and reliable HPLC method was developed and validated for the simultaneous quantification of four major constituents in Semen Vaccariae. The chromatographic separation was performed on an Agilent Zorbax SB-C18 column with gradient elution using methanol and water. The calibration curves showed good linearity of R2 > 0.9999 with LOQs (S/N = 10) of 0.20–1.16 μg/mL. The precision was evaluated by intra- and inter-day assays and R.S.D. values were less than 2.09%. The recovery rates were between 97.0% and 105.0%. The developed method was applied to the quantitative analysis of Semen Vaccariae and its stir-fried products. During the stir-frying process, vaccarin degraded and yielded isovitexin-2″- O-arabinoside. The preferable stir-frying temperature is around 120°C. The developed HPLC method can be applied to the quality control of crude and stir-fried Semen Vaccariae.
Oligonol-induced Degradation of Perilipin 1 is Regulated through Lysosomal Degradation Machinery
Authors: Ogasawara Junetsu , Kitadate Kentaro , Nishioka Hiroshi , Fujii Hajime , Sakurai Takuya , Kizaki Takako , Izawa Tetsuya , Ishida Hitoshi , Ohno Hideki
Published: March 2019

The results obtained from our previous study showed that the addition of a lychee fruit-derived low molecular form of polyphenol, Oligonol, provoked higher levels of lipolytic activity via the degradation of perilipin 1 in primary rat adipocytes. In the current study, we investigated the possible mechanisms by which Oligonol could promote the degradation of perilipin 1 protein. The addition of Oligonol caused the degradation of GFP-tagged perilipin 1 in a time-dependent manner. Meanwhile, the co-addition of Oligonol and NH4Cl, a lysosome inhibitor, failed to promote the degradation of perilipin 1, while the co-addition of Oligonol and MG132, a proteasome inhibitor, induced a reduction in the levels of perilipin 1. These results suggest that the Oligonol-induced degradation of perilipin 1 is regulated via a lysosome-dependent mechanism.
Plant Growth Inhibitor from the Malaysian Medicinal Plant Goniothalamus andersonii and Related Species
Authors: Takemura Tomoko , Kamo Tsunashi , Ismil Raihan , Bakar Baki , Wasano Naoya , Hiradate Syuntaro , Fujii Yoshiharu
Published: March 2019

A crude methanol extract of Goniothalamus andersonii J. Sinclair strongly inhibited elongation of lettuce ( Lactuca sativa L.) radicles. We conducted bioassay-guided purification of G. andersonii bark extract and obtained goniothalamin as the major bioactive compound. Its EC50 values against elongation of lettuce radicles and hypocotyls were 50 and 125 μmol L−1, respectively. Among the six species tested, timothy was the most sensitive to goniothalamin. Quantification of this compound in other Goniothalamus species suggested that the plant inhibitory activity of this genus is explainable by goniothalamin, with G. calcareus as an exception.
Activity of Alkanediol Alkanoates against Pathogenic Plant Fungi Rhizoctonia solani and Sclerotium rolfsii
Authors: Shukla Paraj , Walia Suresh , Ahluwalia Vivek , Parmar Balraj S. , Nair Muraleedharan G.
Published: March 2019

Thirty known dialkanoates of ethylene, propylene and diethylene glycols were synthesized by reacting the glycols with acyl chlorides and their structures confirmed by IR, NMR and mass spectral analyses. They exhibited significant antifungal activity against two phytopathogenic fungi Rhizoctonia solani Kuehn and Sclerotium rolfsii Sacc in a dose dependent manner. Propylene glycol dipentanoate was the most active against R. solani. followed by diethylene glycol dibutanoate and ethylene glycol dibutanoate. Against S. rolfsii ethylene glycol diheptanoate was found to be most active followed by diethylene glycol diisobutanoate As compared to the standard reference benomyl (EC50 5.16 μg/mL), the potential alkanediol dialkanoates showed EC50 in the range of 33 – 60 μg/mL.
A Somaclonal Variant of Rose-Scented Geranium (Pelargonium spp.) with Moderately High Content of Isomenthone in its Essential Oil
Authors: Kulkarni Swaroop S , Ravindra Nagawara S , Srinivas Kalavagunta V N S , Kulkarni Raghavendra N
Published: March 2019

Rose-scented geranium ( Pelargonium spp.), which is highly valued for its essential oil, is exclusively propagated vegetatively. Hence no genetic improvement work is possible through conventional breeding. Somaclonal variation was generated with and without in vitro mutagenesis using N-nitroso- N-methyl urea (NMU) in an Indian cultivar ‘Bourbon’, and a clone ‘Narmada’. A somaclonal variant (N75) with a moderately high content of isomenthone in its essential oil was isolated from somaclones generated after treatment of internodal explants of clone, ‘Narmada’ with 0.25 mM NMU for 1 h. The contents of isomenthone in its essential oil were 26% and 35%, respectively, in SC2/VM2 and SC3/VM3 generations (second and third vegetative generations, respectively, after in vitro mutagen treatment) as compared with 0.7% and 0.3%, respectively, in the parental clone, ‘Narmada’. The contents of alcohols and their esters (linalool, citronellol, geraniol, citronellyl formate and geranyl formate) in the essential oil of N75 in SC2/VM2 and SC3/VM3 generations were 49% and 35%, respectively, as compared with 69% and 63%, respectively, in the parental clone, ‘Narmada’. This is the first report on a chemovariant of rose-scented geranium with a moderately high content of isomenthone. All earlier reported isomenthone-rich variants of rose-scented geranium had quite high contents of isomenthone (64-71%) in their essential oils. The probable modes of origin of this somaclonal variant, its parental clone ‘Narmada’ (with very low content of isomenthone) and four earlier reported isomenthone-rich variants of Indian cultivars of geranium are discussed.
Comparative Study of the Chemical Composition of Essential Oils of Five Tagetes Species Collected in Venezuela
Authors: Armas Kaylin , Rojas Janne , Rojas Luis , Morales Antonio
Published: March 2019

The leaves and inflorescences of five species of Tagetes, family Asteraceae, were collected from different locations in Mérida state, Venezuela, and their essential oils analyzed by GC and GC/MS. Several differences were observed in the composition of these oils, mainly regarding the major components, which for T. caracasana were trans-ocimenone (64.3%) and cis-tagetone (13.7%), and for T. erecta, piperitone (35.9%) and terpinolene (22.2%). High amounts of trans-anethole (87.5%) and estragole (10.7%) were observed in T. filifolia, while T. subulata essential oil contained terpinolene (26.0%), piperitenone (13.1%) and limonene (10.8%). For T. patula, two different oil samples were analyzed, leaves (TPL) and inflorescences (TPI). The TPL oil showed terpinolene (20.9%) and piperitenone (14.0%) as main components, while the TPI sample was composed mainly of β-caryophyllene (23.7%), terpinolene (15.6%) and cis-β-ocimene (15.5%).
Chemical Composition and Antiphytoviral Activity of Essential Oil of Micromeria graeca
Authors: Vuko Elma , Dunkić Valerija , Bezić Nada , Ruščić Mirko , Kremer Dario
Published: March 2019

Phytochemical analysis of the essential oils of Micromeria graeca (L.) Rchb from Vis and Komiža on the island of Vis (Croatia) showed them to have a similar chemical composition. The oxygenated sesquiterpene α-bisabolol was a major component of both oils with percentages of 13.9% in the oil from Vis and 15.5% in the oil from Komiža. A comparison of the mean number of lesions on the essential oil-treated Chenopodium quinoa plants infected with satellite-associated cucumber mosaic virus (satCMV) with the corresponding control showed that the oil from Vis caused delay in the development and reduction of the number of lesions by 59.3%. The essential oil of M. graeca from Komiža was not effective in the reduction of satCMV infection.
Antimicrobial and Antioxidant Activities of Stachys lavandulifolia subsp. lavandulifolia Essential Oil and its Infusion
Authors: İşcan Gökalp , Demirci Betül , Demirci Fatih , Göger Fatih , Kırımer Neşe , Köse Yavuz B. , Başer Kemal Hüsnü Can
Published: March 2019

Stachys lavandulifolia Vahl. subsp. lavandulifolia (Lamiaceae) is widely used in south Anatolia as a herbal tea. It is used for the treatment of gastrointestinal and respiratory disorders. Constituents of the essential oil obtained by hydrodistillation were analyzed both by GC-FID and GC/MS, simultaneously. Thirty-seven compounds representing 98.3% of the oil were characterized. β-Phellandrene (27%), α-pinene (18.5%) and germacrene-D (13%) were found as major components of the oil. Anticandidal, antibacterial and antioxidant properties of the oil and the prepared infusion were evaluated using several methods. The oil exhibited good inhibitory activity on Candida tropicalis (MIC 0.094 mg/mL). Staphylococcus aureus and Salmonella typhimurium growths were also inhibited by the oil at a concentration of 0.375 mg/mL. The prepared infusion of the flowering aerial parts showed weak antimicrobial effects against all the tested microorganisms, but demonstrated a remarkably radical scavenging activity (IC50: 3.9 μg/mL).
Antiplasmodial Activity of the Ethnobotanical Plant Cassia fistula
Authors: Grace Mary H. , Lategan Carmen , Graziose Rocky , Smith Peter J. , Raskin Ilya , Lila Mary Ann
Published: March 2019

In our ongoing investigation of new compounds with activity against malaria parasites, we tested the in vitro antiplasmodial activity of fractions and purified compounds from Cassia fistula L., a plant traditionally used by native populations of Tanzania, Zimbabwe, Mozambique and Brazil to treat malaria or symptoms associated with this disease. Crude extracts from leaves, bark and fruits were tested for their antiplasmodial activity against the chloroquine-sensitive strain of Plasmodium falciparum(D10), where leaf extracts showed the highest activity. The chloroform extract of the leaves was further bioassay-guided fractionated using a combination of centrifugal partition chromatography and flash column chromatography. Three main antiplasmodial principles, phytol (1) (IC50 18.9 ± 0.60 μM), lutein (2) (IC50 12.5 ± 0.35 μM), and di-lineolylgalactopyranosyl-glycerol (DLGG) (IC50 5.8 ± 0.27 μM) (3), were isolated and identified using spectroscopic methods. When the three active principles were tested for their cytotoxicity using a Chinese Hamster Ovarian (CHO) cell line, compound 3 showed very weak toxicity (IC50 75.9 ± 0.28 μM), while the other two compounds were nontoxic, even at the highest concentration tested. The study provides evidence to support the use of Cassia fistula as an antimalarial remedy and describes the antiplasmodial constituents from the leaves.
Trichilone, a New C21 Steroid from Trichilia Connaroides
Authors: Zhang Qiang , Zhang Yu , He Hong-Ping , Di Ying-Tong , Hao Xiao-Jiang
Published: March 2019

Phytochemical investigation of the leaves of Trichilia connaroides led to the isolation of a new pregnane, trichilone (1), featuring a 2-methoxycyclopent-2-enone moiety, along with a related known compound, 3 β,4 α-dihydroxypregnane-16-one (2). The structure of 1 was established on the basis of extensive spectroscopic analysis. Compound 1 showed significant root-growth inhibition activity against Amaranthus. mangostanus with an IC50 value of 23.1 ppm.
Three Novel Immunosuppressive Steroidal Glycosides from the Stems of Stephanotis Mucronata
Authors: Li Xiao-yu , Zong Shu-ling , Chen Feng-yang , Xu Shi-fang , Ye Yi-ping
Published: March 2019

Three novel and one known C21 steroidal glycosides were isolated from the stems of Stephanotis mucronata. Their structures were determined on the basis of chemical evidence and extensive spectroscopic methods. The four C21 steroidal glycosides displayed significant immunosuppressive activities in vitro.
Quantitative Analysis of Substituted N,N-Dimethyl-tryptamines in the Presence of Natural Type XII Alkaloids
Authors: Ivanova Bojidarka , Spiteller Michael
Published: March 2019

This paper reports the qualitative and quantitative analysis (QA) of mixtures of hallucinogens, N,N-dimethyltryptamine (DMT) (1), 5-methoxy- (1a) and 5-hydroxy- N,N-dimethyltryptamine (1b) in the presence of β-carbolines (indole alkaloids of type XII) {(2), (3) and (5)}. The validated electronic absorption spectroscopic (EAs) protocol achieved a concentration limit of detection (LOD) of 7.2.10-7 mol/L {concentration limit of quantification (LOQ) of 24.10-7mol/L} using bands (λmax) within 260±0.23-262±0.33 nm. Metrology, including accuracy, measurement repeatability, measurement precision, trueness of measurement,and reproducibility of the measurements are presented using N,N- dimethyltryptamine (DMA) as standard. The analytical quantities of mixtures of alkaloids 4, 6 and 7 are: λmax 317±0.45, 338±0.69 and 430±0.09 for 4 (LOD, 8.6.10-7 mol/L; LOQ, 28.666, mol/L), as well as 528±0.75 nm for 6 and 7 (LOD, 8.2. 10-7 mol/L; LOQ, 27.333, mol/L), respectively. The partially validated protocols by high performance liquid chromatography (HPLC), electrospray ionization (ESI), mass spectrometry (MS), both in single and tandem operation (MS/MS) mode, as well as matrix/assisted laser desorption/ionization (MALDI) MS are elaborated. The Raman spectroscopic (RS) protocol for analysis of psychoactive substances, characterized by strong fluorescence RS profile was developed, with the detection limits being discussed. The known synergistic effect leading to increase the psychoactive and hallucinogenic properties and the reported acute poisoning cases from 1-7, make the present study emergent, since as well the current lack of analytical data and the herein metrology obtained contributed to the elaboration of highly selective and precise analytical protocols, which would be of interest in the field of criminal forensic analysis.
HPLC Analysis of Stemokerrine and Oxystemokerrine in the Thai Medicinal Plant Stemona kerrii
Authors: Kongkiatpaiboon Sumet , Keeratinijakal Vichien , Gritsanapan Wandee
Published: March 2019

A HPLC-UV method was developed and validated for determination of stemokerrine and oxystemokerrine in Stemona kerrii roots. The chromatographic separation was performed on a Hypersil BDS C18-column eluted with methanol: 50 mM ammonium acetate solution using a gradient system with a flow rate of 1 mL/min and detection at 300 nm. Stemokerrine and oxystemokerrine showed a linear relationship within the range of 0.5-100 μg/mL. The method was shown to be precise with a RSD <2%. The average percent recovery of stemokerrine was 101.6% and for oxystemokerrine 99.5%. Two samples of S. kerrii were analyzed and the average contents of stemokerrine and oxystemokerrine were 0.2 and 0.05%, w/w, respectively. The present work will provide a useful standardization method for S. kerrii raw materials for further pharmaceutical development.
Dihydroflavonol and Flavonol Derivatives from Macaranga Recurvata
Authors: Tanjung Mulyadi , Hakim Euis H. , Elfahmi  , Latip Jalifah , Syah Yana M.
Published: March 2019

Two new dihydroflavonol derivatives, macarecurvatins A and B, have been isolated from the leaves of Macaranga recurvata(Euphorbiaceaae), along with the known compounds diisoprenylaromadendrin, glyasperin A and broussoflavonol F. The structures of the new compounds were determined on the basis of spectroscopic evidence. Upon cytotoxic evaluation against P-388 cells, macarecurvatin B showed strong activity with an IC50 of 0.83 μM.
A New Prenylated Acetophenone from the Root Bark of Derris indica
Authors: Edayadulla Naushad , Ramesh Penugonda
Published: March 2019

A new acetophenone, 1-[2,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl]ethanone (1) was isolated from the root bark of Derris indica, along with 3,7,-dimethoxy-3’,4’-methylenedioxyflavone (desmethoxykanugin) (2), 5-methoxyfurano[4″, 5″: 6, 7] flavone (pinnatin) (3), and 3′-hydroxyfurano[4″,5″:7,8]flavone (pongol) (4). The structures of these compounds were established by means of chemical and spectral studies. The occurrence of this prenylated acetophenone in D. indica is of biogenetic and chemotaxonomic significance.
Phytotoxic Furanocoumarins from the Shoots of Semenovia Transiliensis
Authors: Sondhia Shobha , Duke Stephen O. , Green Solomon , Gemejiyeva Nadezhda G. , Mamonov Leonid K. , Cantrell Charles L
Published: March 2019

Discovery of novel, natural herbicides has become important to manage increasing weed resistance to synthetic herbicides and environmental issues. The systematic bioassay-guided fractionation and purification of the methylene chloride/methanol extract of the shoots of Semenovia transiliensis led to the isolation of several phytotoxic compounds. Lactuca sati v a L. (lettuce, a dicot) and Agrostis stolonifera L. (bentgrass, a monocot) bioassays were used to identify and isolate the phytotoxic fractions. A number of furanocoumarin compounds isolated from S. transiliensis shoots were phytotoxic to both test species. These included psoralen, isopsoralen, heratomin, isopentenyloxyisobergapten, imperatorin, bergapten, xanthotoxin, heraclenin, and heraclenol. All the active secondary metabolites isolated from the shoots of S. transiliensis were furanocoumarins. Identification of these was accomplished using mass spectrometry and 1- and 2-dimensional NMR techniques. Phytotoxic activity of isolated compounds was evaluated in a dose–response manner from 0.3 to 1000 μM. In general, all of the compounds were more active on A. stolonifera than L. sativa. Bergaptin and xanthotoxin were the most active of the compounds, with moderate activity at 100 μM. Imperatorin and xanthotoxin inhibited growth of Lemna paucicostata Hegelm. by 50% at 29 and 60 μM, respectively. Our results show that S. transiliensis is rich in furanocoumarins, which are probably involved in various aspects of the chemical ecology of the species. Unfortunately, the general cytotoxicity of furanocoumarins makes them an unlikely candidate for pesticide discovery.
Novel Sorbicillin Analogues from the Marine Fungus Trichoderma sp. Associated with the Seastar Acanthaster Planci
Authors: Lan Wen-Jian , Zhao Yang , Xie Zhong-Liang , Liang Li-Zhen , Shao Wei-Yan , Zhu Long-Ping , Yang De-Po , Zhu Xiao-Feng , Li Hou-Jin
Published: March 2019

Two novel sorbicillinoid analogues, (4' Z)-sorbicillin (1) and (2 S)-2,3-dihydro-7-hydroxy-6-methyl-2-[( E)-prop-1-enyl]-chroman-4-one (2), together with three known compounds, (2 S)-2,3-dihydro-7-hydroxy-6,8-dimethyl-2-[( E)-prop-1-enyl]-chroman-4-one (3), sorbicillin (4), and 2',3'-dihydrosorbicillin (5), were isolated from the culture broth of the fungus Trichoderma sp. associated with the seastar Acanthaster planci. Their structures were determined by analysis of the NMR and MS data. Compound 1 was the first example with a Z-configuration of the C-4'/C-5’ double bond in the sorbyl side chain. Compounds 2 and 3 were uncommon monomeric sorbicillinoids with a cyclic sorbyl chain. 2, 3 and 5 showed moderate cytotoxic activities against various cancer cell lines.
Cytotoxic Bioactivity of Some Phenylpropanoic Acid Derivatives
Authors: Reta Guillermo F. , Tonn Carlos E. , Ríos-Luci Carla , León Leticia G. , Pérez-Roth Eduardo , Padrón José M. , Donadel Osvaldo J.
Published: March 2019

In this study, we synthesized a series of phenylpropanoic acid derivatives based on modifications at four selected points of the molecular scaffold. The in vitro antiproliferative activities of the compounds were examined in representative human solid tumor cell lines. A SAR was established pointing out the relevance of the substituents. The best activity profiles were obtained for the derivatives bearing more lipophilic esters (GI50 3.1-21 μM).
Anti-Helicobacter Pylori Activities of Natural Isopentenyloxycinnamyl Derivatives from Boronia Pinnata
Authors: da Silva Cécile Ribeiro , Michel Valérie , Genovese Salvatore , Prévost Marie-Christine , Epifano Francesco , Touati Eliette
Published: March 2019

In this study we investigated the anti- Helicobacter pylori activity of four isopentenyloxycinnamyl derivatives from the Australian shrub Boronia pinnata Sm. (Rutaceae), structurally related to boropinic acid: ( E)-3-(4-(3-methylbut-2-enyloxy)-3,5-dimethoxyphenyl)acrylaldehyde (1), boropinol C (2), boropinal (3) and boropinol A (4). In vitro growth of H. pylori strains 26695 and B128 was analyzed in liquid culture with increasing doses of these compounds. Bacterial morphology was visualized by scanning electron microscopy. The in vivo effects of the two most efficient molecules that reduced bacterial growth in vitro, compounds 3 and 4, were investigated on H. pylori gastric colonization in the mouse model. The presence of these compounds in the bacterial cultures led to alterations of bacterial surface and flagella. In vivo, both compounds 3 and 4 at 250 μM reduced significantly the ability of H. pylori to colonize the gastric mucosa of mice, compared with untreated ones. These data indicate that these natural isopentenyloxycinnamyl derivatives related to boropinic acid can be considered as novel antibacterial agents with anti- H. pylori activity.
Novel Application of Mahua (Madhuca sp.) Flowers for Augmented Protease Production from Aeromonas sp. S1
Authors: Bhattacharya Amrik , Saini Vandana , Gupta Anshu
Published: March 2019

The present study explored the utilization of Mahua ( Madhuca sp.) flowers, a major non-timber forest product (NTFP) of India, as a low-cost, natural substrate for protease production under submerged fermentation. Bacterial strain Aeromonas sp. S1, previously reported by us, was used as the protease producer. Using Mahua flower extract (MFE) as the medium additive, the protease production could successfully be enhanced by 5.6-fold (564.5 UmL−1) after 24 h of fermentation under optimized conditions compared with initial production of 99.9 UmL−1 in the absence of MFE. The cultural parameters for optimum production of protease were determined to be: incubation time-24 h; pH-7.0; MFE concentration-5% (v/v); inoculum size-0.3% (v/v) and agitation rate-200 rpm. The results obtained demonstrate the potential of cheaper and abundantly available Mahua flowers for induction of proteases, and thus offer a new approach for value addition to this biomass through industrial enzyme production.