bluuebunny/crossref_metadata_2025 huggingface dataset:
New Oleanane Glycosides from the Roots of Gomphrena macrocephala
Authors: Kuroda Minpei , Aoshima Taku , Haraguchi Mitsue , Young Maria Cláudia Marx , Sakagami Hiroshi , Mimaki Yoshihiro
Published: March 2019

Six new (1–6) and one known (7) oleanane glycosides have been isolated from the roots of Gomphrena macrocephala. On the basis of 1D- and 2D-NMR spectroscopic data and the results of hydrolysis, the structures of 1–6 were determined to be 3β-[(O-β-D-glucuronopyranosyl)oxy]oleana-11,13-dien-28-oic acid (1), 3β-[(O-β-D-galactopyranosyl-(1→3)-O-[β-D-glucopyranosyl-(1→2)]-β-D-glucuronopyranosyl)oxy]oleana-11,13-dien-28-oic acid (2), 3β-[(O-β-D-glucuronopyranosyl)oxy]oleana-9,12-dien-28-oic acid β-D-glucopyranosyl ester (3), 3β-[(O-β-D-galactopyranosyl-(1→3)-O-[β-D-glucopyranosyl-(1→2)]-β-D-glucuronopyranosyl)oxy]oleana-9,12-dien-28-oic acid β-D-glucopyranosyl ester (4), 3β-[(O-β-D-galactopyranosyl-(1→3)-O-[β-D-glucopyranosyl-(1→2)]-β-D-glucuronopyranosyl)oxy]-11-oxo-olean-12-en-28-oic acid β-D-glucopyranosyl ester (5), and 3β-[(O-β-D-galactopyranosyl-(1→3)-O-[β-D-glucopyranosyl-(1→2)]-β-D-glucuronopyranosyl)oxy]-11α-hydroxyolean-12-en-28-oic acid β-D-glucopyranosyl ester (6), respectively. Although 1–7 did not show apparent cytotoxicity against human oral squamous cell carcinoma (HSC-2) cells and normal human pulp cells (HPC), the aglycones 1a and 3a of 1 and 3 exhibited tumor-specific cytotoxicity against HSC-2 cells, and the IC50 value of 3a against HSC-2 cells was almost equal to that of etoposide, used as a positive control.
Butanolides from the Stem of Cinnamomum Kotoense
Authors: Chen Chung-Yi
Published: March 2019

Kotomolide (1), obtusilactone A (2), isoobtusilactone A (3), secokotomolide (4), kaempferol (5), quercetin (6), (-)-catechin (7), (-)-epicatechin (8), (-)-sesamin (9), isoeugenol (10), trans-ferulic acid (11), benzoic acid (12), p-hydroxybenzoic acid (13), p-hydroxybenzaldehyde (14), a mixture of β-sitosterol (15) and stigmasterol (16), and a mixture of β-sitosterol-D-glucoside (17) and stigmasterol-D-glucoside (18) were isolated from the stems of Cinnamomum kotoense Kanehira & Sasaki. Among them, 1 is a new compound. The structures of these compounds were characterized and identified by spectral analyses.
Nematicidal Activity of the Essential Oils from Pilocarpus microphyllus (Rutaceae) Samples
Authors: Romero Nirla R. , Andrade-Neto Manoel , Gonçalves Francisco J. T. , Nascimento Raimundo R. G. , Bezerra Franciglauber S. , de Oliveira Maria C. F. , Barbosa Francisco G. , Bezerra Antonio M. E. , Mafezoli Jair , Sena José S. P.
Published: March 2019

The composition and nematicidal activity of the essential oils from the leaves of native and six cultivated varieties of P. microphyllus are reported. Twenty-nine compounds were identified (86.2% sesquiterpenes and 13.8% aliphatic ketones) of which (E)-caryophyllene, germacrene-D, caryophyllene oxide, 2-tridecanone, and 1-hydroxy-2-tridecanone were found in all of the analyzed oils. The nematicidal activity of all the oils was evaluated against the second-stage juvenile nematode Meloidogyne incognita. Essential oils from native P. microphyllus and varieties Xingu and Linha V showed high nematicidal activity, while no activity was found for the other oils. This result was associated with the high concentrations of both 2-tridecanone and 1-hydroxy-2-tridecanone in the active oils. Both ketones were isolated from one of the active oils and showed 100% activity at 1000 ppm concentration.
Antibiotic-Induced Alterations in the Osmotic Resistance of Erythrocytes is Modulated by β-Carotene and L –Ascorbic Acid
Authors: Luqman Suaib , Prabu K V Obli , Pal Anirban , Saikia Dharmendra , Darokar Mahendra P , Khanuja Suman P S
Published: March 2019

Ciprofloxacin, Erythromycin and Norfloxacin are potent anti-microbials. These antibiotics, besides affecting bacteria, also exert toxic effects on mammalian cells. The present work was undertaken to study the effect of these antibiotics on the osmotic fragility profile of erythrocytes and the protective role played by vitamin supplementation, which exerts a stabilizing effect on the erythrocytes making them more resistant to lysis under hypotonic stress. The protective effect of β-carotene and L-ascorbic acid was significant (p < 0.01) at 0.1 mM and 0.01 mM concentrations. No significant effect was observed at lower concentrations. The free radical scavenging activity and effect of these vitamins on membrane fluidity and permeability may explain the protective role against the damage induced by the antibiotics on the erythrocytes membrane.
Antioxidant Effects on Lipid Peroxidation by Superoxide of Echinoisoflavanone and Sophoraisoflavanone D from Sophora Chrysophylla Seem
Authors: Toda Shizuo , Shirataki Yoshiaki
Published: March 2019

The possible antioxidant effect of two isoflavanones, echinoisoflavanone and sophoraisoflavanone D from Sophora chrysophylla Seem. was investigated. Both these compounds inhibited the superoxide anion-mediated lipid peroxidation of lecithin and scavenged superoxide anion generated by the xanthine-xanthine oxidase system. These results indicated the impressive antioxidant property of these two compounds.
Larvicidal Activity against Aedes Aegypti L. (Diptera: Culicidae) of Essential Oils of Lippia Species from Brazil
Authors: Santiago Gilvandete M. P. , Lemos Telma L. G. , Pessoa Otília D. L. , Arriaga Ângela M. C. , Matos Francisco J. A. , Lima Mary Anne S. , Santos Hélcio S. , Lima Maria da Conceição L. , Barbosa Francisco G. , Luciano João H. S. , Silveira Edilberto R. , de Menezes Gustavo H. A.
Published: March 2019

The larvicidal activity of the essential oils from leaves of five species of Lippia (L. alba, L. aff. gracilis, L. gracilis, L. microphylla and L. nodiflora) was studied on third instar larvae of Aedes aegypti. The larvae were exposed to serial concentrations from 500 to 12.5 μg/mL of the essential oils. The results indicate that the oil of L. gracilis has a higher larvicidal activity with a LC50 of 26.3 μg/mL The results suggest the use of these essential oils as natural larvicidal agents.
Alteration in the Respiratory Pathway of the Freshwater Fish Channa Punctatus Induced by Euphorbia Royleana Stem Bark Extract
Authors: Tiwari Sudhanshu , Singh Ajay
Published: March 2019

The piscicidal activity of the diethyl ether extract of Euphorbia royleana stem bark has been well established, but its ultimate mode of action and short, as well as long-term, biochemical effects are not yet known. Exposure of fish for either 24 or 96 hours to sub-lethal doses (40% and 80% of LC50) of the diethyl ether extract of the stem bark, significantly (P<0.05) altered total protein, total free amino acids, nucleic acids, glycogen, pyruvate, and lactate levels, as well as protease, aminotransferase, phosphatases and cytochrome oxidase enzyme activity in liver and muscle tissue of the freshwater fish Channa punctatus. These alterations were significantly (P<0.05) time and dose dependent. Thus, the diethyl ether extract of E. royleana stem bark shifts the aerobic pathway of fish respiration towards the anaerobic segment and also suppresses ATP production. This toxic effect was reversible, and seven days after withdrawal, all biochemical parameters were back to normal. These results support the view that the diethyl ether extract of E. royleana stem bark can be used for controlling unwanted populations of the predatory fish C. punctatus from aquaculture ponds.
Induction Effects of Apigenin, Luteolin and Vinpocetin on Neutral Endopeptidase (NEP) and Angiotensin-Converting Enzyme Activity (ACE) of SK-N-SH Cells
Authors: Ayoub Shereen , Melzig Matthias F.
Published: March 2019

The long-term effects of a number of flavonoids (such as apigenin, luteolin and amentoflavone) and vinpocetine on the neutral endopeptidase (NEP) and angiotensin-converting enzyme (ACE) were investigated. It was shown that apigenin, luteolin and vinpocetin are able to induce the activity of both NEP and ACE associated with the inhibition of the proliferation of the neuroblastoma cell line SK-N-SH. Amentoflavone has no effect on either NEP or ACE activity. An additional enhancement of cellular NEP activity could be detected after the treatment of the cells with a combination of both arabinosylcytosine and either apigenin or luteolin. This effect supports the assumption that apigenin and luteolin influence directly the gene expression of NEP. Taking into account the significant role of NEP and ACE in the degradation of amyloid beta peptides, the induction of both enzymes by long-term treatment with apigenin, luteolin and vinpocetine may have a beneficial effect regarding the prevention of the formation of amyloid plaques and the effect of these substances may be discussed as neuroprotective.
Antimicrobial Activity and Chemical Composition of Essential Oil of Eupatorium Glutinosum (Lam.)
Authors: El-Seedi Hesham R.
Published: March 2019

The essential oil obtained by steam distillation from the leaves and twigs of Eupatorium glutinosum Lam. (Asteraceae) showed antimicrobial activities against a Gram-positive bacterium, three Gram–negative bacteria and three fungi. The results from this study support the vernacular medicinal uses of the plant in folkloric medicine. The chemical composition of the essential oil was analysed by GC and GC-MS, resulting in the identification of 24 constituents accounting for 92.6% of the total mass. The major active component, carvacrol, was isolated using MPLC and characterized by NMR and MS analysis. β-Glucosidase-treatment of the aqueous plant residue yielded a volatile fraction that did not show antimicrobial activitiy, in which the major components were octen-3-ol and (Z)-hex-2-en-1-ol. The essential oil from the species is reported for the first time.
Pregnane Glycosides
Authors: Panda Nilendu , Banerjee Sukdeb , Mandal Nirup B. , Sahu Niranjan P.
Published: March 2019

Pregnane glycosides constitute a class of compounds widely distributed in the plant kingdom. Many of them have shown either anticarcinogenic or cancer inhibitory properties, besides other useful biological activities. New chromatographic techniques and advances in spectroscopic and spectrometric methods have accelerated the purification and structure determination of novel glycosides of this series. A compilation of the pregnane glycosides isolated from 1995 until the middle of 2005, along with their physical data, structures and occurrence are presented in this review, which also summarizes, with suitable examples, recent developments in isolation and purification techniques, and structural elucidation using modern spectrometric methods like ESIMS and tandem mass spectrometry, and 2D NMR spectroscopic strategies. The reported anticancer and other biological activities of pregnane glycosides are also discussed.
Polyphenolic Profile and Biological Study of Salvia Fruticosa
Authors: Moharram Fatma A. , Mahmoud Ibrahim I. , Mahmoud Madeha R. , Sabry Samah A.
Published: March 2019

Two new flavone glycosides, scutellarin 3,8-di-C-β-D-4C1-glucopyranoside (1) and luteolin 7-O-β-D-4C1-glucopyranoside-6′‘ sulfate (2) together with sixteen known metabolites viz diosmin (3), apigenin 7-O-β-D-rutinoside (4), luteolin 7-O-β-D-rutinoside (5) luteolin 7-O-(6′‘-O-acetyl)-β-D-4C1-glucopyranoside (6), luteolin 7-O-β-D-4C1-galacturonopyranoside (7), luteolin 7-O-β-D-4C1-glucuronopyranoside (8), apigenin 7-O-β-D-4C1-glucouronopyranoside (9), apigenin 7-O-β-D-4C1-glucouronopyranoside methyl ester (10), luteolin 7-O-β-D-4C1-glucuronopyranoside methyl ester (11), cosmosiin (12), cinaroside (13), homoplontagenin (14), apigenin (15), luteolin (16), caffeic (17) and chlorogenic acids (18) were isolated from the aerial parts of Salvia. fruticosa Mill. Compounds 3, 6, 7, 10 and 11 were isolated for the first time from this genus, while 4, 5 and 14 isolated for the first time from S. fruticosa. Their chemical structures have been established on the basis of chemical and spectroscopic evidence. It was found that both 80% methanol and chloroform extracts of S. fruticosa are non-toxic to mice (LD50 up to 4 g. Kg−1 b. wt.). Their administration at 100 and 200 mg Kg−1 b. wt. improved liver functions, reduced the hepatotoxicity and the 80% methanol extract showed significant hypoglycemic effect and antispasmodic activity, as well.
The Chemical Composition of Phymatidium Delicatulum and P. Tillandsioides (Orchidaceae) Floral Oils
Authors: Reis Mariza G. , Singer Rodrigo B. , Gonçalves Renato , Marsaioli Anita J.
Published: March 2019

The chemistry of the floral oils of Phymatidium delicatulum and P. tillandsioides (Orchidaceae) is described. These small epiphytes produce the oils in a complex gland (the elaiophore) located on the median petal. The floral oils of P. tillandsioides were shown to be comprised mostly of acylglycerols, as in many other Oncidiinae orchids from southeastern Brazil. Surprisingly, the floral oil of P. delicatulum was composed, predominantly, of relatively simple linear hydrocarbons. Evidence that P. delicatulum is pollinated by females of the oil-gathering bee genus Tetrapedia (Apidae: Tetrapediini) is presented.
TiCl3 as a New Catalyst for the Imino Diels-Alder Reaction
Authors: Mayekar Narayan V. , Nayak Sandip K. , Chattopadhyay Subrata
Published: March 2019

Titanium(III) chloride was found to be an effective catalyst for the imino Diels-Alder reaction between an imine (generated in situ) and an activated alkene in acetonitrile at ambient temperature. The reaction proceeds smoothly to afford the corresponding adduct as a mixture of chromatographically separable cis- and trans isomers in moderate to good yields.
Alkaloids from the Root of Flueggea Virosa
Authors: Gan Li-She , Yue Jian-Min
Published: March 2019

Nine alkaloids, including one new norsecurinine derivative norsecurinic acid (1), and two artificial alkaloid products, 15β-butoxy-14,15-dihydronorsecurinine (2) and 15α-butoxy-14,15-dihydronorsecurinine (3), were isolated from the root of Flueggea virosa. Their structures and configurations were elucidated by chemical and spectroscopic methods, especially 2D NMR techniques.
Constituents of Medicinal Plants of Lombok: A New Antibacterial Alkaloid from Voacanga Foetida (Bl.) Rolfe
Authors: Hadi Surya , Bremner John B.
Published: March 2019

A new, weakly antibacterial indole alkaloid, named lombine, together with the known alkaloid voacangine, have been isolated from the bark of Voacanga foetida (Bl.) Rolfe (Apocynaceae), a plant used on Lombok, Indonesia, for medicinal purposes. A combined chemo- and bio-rational strategy was developed to target this plant for investigation. Lombine was shown to be bactericidal against Staphylococcus aureus and Escherichia coli.
Progress on Cassaine-Type Diterpenoid Ester Amines and Amides (Erythrophleum Alkaloids)
Authors: Qu Jing , Yu Shishan , Tang Wenzhao , Liu Yunbao , Liu Yue , Liu Jing
Published: March 2019

The structures, spectral characteristics, and bioactivities of 39 natural cassaine-type diterpenoid ester amines and amides (Erythrophleum alkaloids) and 31 synthetic analogues are reviewed. Cassaine-type diterpenoid ester amines and amides, the so called Erythrophleum alkaloids, have the skeleton of cassane-type diterpenoids with a N-containing side chain, and are classified into two groups, ester amines and amides. Cassaine-type diterpenoid ester amines and amides show remarkable inotropic action on the heart, inhibition of Na+/K+-ATPase, cytotoxities, and other major bioactivities. Structural modification of cassaine-type diterpenoid ester amines and amides has been carried out to furnish many derivatives to study the structure-activity relationships.
Asymmetric Synthesis of Quinine: A Landmark in Organic Synthesis
Authors: Nair Vijay , Menon Rajeev S. , Vellalath Sreekumar
Published: March 2019

Ever since its isolation in 1820, Quinine has played a crucial role in the development of organic chemistry, the chemical industry and modern medicine. A total synthesis of quinine, widely regarded as an event of epochal importance, was claimed by Woodward and Doering in 1945. This work, however, heavily relied on unsubstantiated literature reports and it appears that Woodward's work fell short of a total synthesis of quinine. The first total synthesis of quinine was reported by Uskokovic in the 1970s. The first stereoselective total synthesis of quinine was accomplished only in 2001, by Stork, who incidentally is the originator of the concept of stereoselectivity in total synthesis. Apart from the stereoselectivity, Stork's synthesis of quinine is remarkable for its conceptual uniqueness and retrosynthetic novelty. Naturally, this work has been attested as a landmark in organic synthesis by leaders in the field. Subsequently, Jacobson and Kobayashi reported the catalytic asymmetric synthesis of quinine in 2003 and 2004, respectively. Both these synthesis have followed a similar approach. The present review has attempted to provide a concise account of the synthesis of quinine from a historical perspective.
Chemodiversity of Exudate Flavonoids, as Highlighted by Selected Publications of Eckhard Wollenweber
Authors: Valant-Vetschera Karin M. , Brem Brigitte
Published: March 2019

Chemodiversity, as a new research concept, is highlighted by a discussion of selected publications of Professor Dr E. Wollenweber. Excretion phenomena of flavonoid aglycones are addressed, such as localization, chemosystematic, and applied aspects. Various classes of flavonoids have been reported from exudates; even flavonoid glycosides and biflavonoids were accumulated on the leaf surfaces of plants. The production of other exudate constituents outside the flavonoid pathway is briefly addressed. The connective role to biological disciplines is stressed, particularly as far as secretory structures are concerned.
Two New Cyclopentanoids from the Endophytic Fungus Aspergillus sydowii Associated with the Marine Alga Acanthophora Spicifera
Authors: Teuscher Franka , Lin Wenhan , Wray Victor , Edrada RuAngelie , Padmakumar K. , Proksch Peter , Ebel Rainer
Published: March 2019

A marine-derived endophytic fungus, identified as Aspergillus sydowii was isolated from the inner tissue of the marine red alga Acanthophora spicifera. After mass cultivation of the fungus, chemical investigation afforded two new chlorinated 2,5-diarylcyclopentenones, which were named sydowin A and B. The structures of the new compounds were established on the basis of NMR spectroscopic (1H, 13C, 1H detected direct, and long range 1H-13C correlations) and mass spectrometric (ESI and FT-ICR-MS) data. Structurally related fungal compounds have hitherto only been described from higher basidiomycetes, but are characterized for the first time from an ascomycete in this study.
Bioactive Flavonoids from Tephrosia Purpurea
Authors: Kassem Mona E. S. , Sharaf Mohamed , Shabana Manal H. , Saleh Nabiel A. M.
Published: March 2019

A new naturally occurring flavonol diglycoside, tamarixetin 3-O-β-glucopyranoside -7-O-α-rhamnopyranoside, was isolated along with two known flavonol diglycosides from the aerial parts of Tephrosia purpurea (L.) Pers. (Fabaceae). Bioassay guided fractionation of the light petroleum extract afforded two bioactive 5-deoxyflavones, pseudosemiglabrin and glabratephrin. Both showed cytotoxicity to the Hepg2 hepatic human cell line with IC50 values of 0.87 and 4.03 μg/mL, respectively. The isolated compounds were characterized by spectroscopic (UV, 1H, 13C, HMQC and HMBC NMR) and spectrometric (EI-MS, ESI-MS) analyses.
Carbon-13 NMR Chemical Shift of Methyl Group: A Useful Parameter for Structural Analysis of C-Methylated Flavonoids
Authors: Agrawal Pawan K. , Agrawal Chandan , Agrawal Shravan
Published: March 2019

The 13C NMR resonances corresponding to the C-Me group of C-6 and/or C-8 C-methylated-flavonoids absorb between 6.7–10.0 ppm and typically between 6.7–8.7 ppm. A comparative 13C NMR study reflects that the 13C NMR chemical shifts reported for 6-hydroxy-5-methyl-3′,4′,5′-trimethoxyaurone-4-O-α-L-rhamnoside from Pterocarpus santalinus and 8-C-methyl-5,7,2′,4′- tetramethoxyflavanone from Terminalia alata are inconsistent with the assigned structures, and therefore need reconsideration.
Characterization of a Novel Flavone O-Methyltransferase Gene in Rice
Authors: Zhou Jian-Min , Fukushi Yukiharu , Wang Xiao-Feng , Ibrahim Ragai K.
Published: March 2019

We report the characterization of a novel flavone O-methyltransferase cDNA (OsOMT1) from the rice genome database. Its recombinant protein utilizes tricetin as the preferred substrate, catalyzing its stepwise methylation to the monomethyl- (selgin), dimethyl- (tricin), as the major product, and trimethyl ether derivatives. The use of this gene to increase tricin content in grain crops is discussed in relation to its potential health benefits.
The B Group Vitamins and Mineral Elements in the Selective Removal of Wheat Kernel Layers
Authors: Vucelic-Radovic Biljana V. , Nesic Vjaceslav M. , Demin Mirjana A. , Milovanovic Mirjana M.
Published: March 2019

The objective of this study was to investigate how selective removal of the surface layers of whole wheat grains by abrasive scouring affects the distribution of mineral elements (macronutrients, micronutrients and trace elements) and the B group vitamins (thiamin, riboflavin pyridoxine, pantothenic acid and niacin) in three soft winter wheat varieties (Partizanka, Novosadska rana and Lasta). Although representing technologically different quality classes of wheat, the varieties were not significantly different in the B group vitamin contents, except for pyridoxine. Whole grains of all varieties exhibited very similar scouring behavior in reduction of vitamins: the most intensive investigated regime only slightly, but not significantly reduced the concentration of the B group vitamins. The nutritive value of scoured wheat grains with regard to the B group vitamins was preserved.

The investigated minerals were: Na, K, Ca, Mg, Mn, Fe, Cu, Zn, Ni, Cr, Se, Pb and Cd. The concentrations of minerals in scoured wheat grains were significantly reduced, dropping on average to 65% of the initial values for macro and 55% for microelements. The change of concentrations with the duration of applied treatment followed different patterns for different elements. Furthermore, a different pattern of the change for the same element in different wheat varieties was noticed. This might be due either to different mechanical properties of bran and bran layer interfaces or genotypic variability in distribution of elements in wheat grain. Severe reduction in Pb concentrations was achieved leading to improvement of whole-wheat food safety.
Phytochemical Quality and Bioactivity of Edible Sprouts
Authors: Moreno Diego A. , Pérez-Balibrea Santiago , García-Viguera Cristina
Published: March 2019

Edible sprouts are phytonutrient-rich plant foods, good source of flavonoids, other polyphenols, glucosinolates, isothiocyanates, proteins, minerals and vitamins. The increasing consumption of sprouts requires optimisation of their quality, palatability and bioactivity. Multiple genetic and environmental factors (growth conditions, stress, elicitors) affect the production and accumulation of phytochemicals in these foods, offering the basis for further research on the improvement of the nutritional and health-relevant functional value of edible sprouts. In the present review, we focus on the phytochemical characteristics of edible sprouts, which can be regarded as a safe and promising a new dietary source of natural products for human health.
New Flavonoid Glycosides from Chrozophora senegalensis and Their Antioxidant Activity
Authors: Vassallo Antonio , Cioffi Giuseppina , De Simone Francesco , Braca Alessandra , Sanogo Rokia , Vanella Angelo , Russo Alessandra , De Tommasi Nunziatina
Published: March 2019

Bioassay-directed fractionation of an antioxidant methanol extract of the leaves of Chrozophora senegalensis using DPPH assay led to the isolation of three new flavonoid glycosides, quercetin 3-O-(6″-caffeoyl)-β-D-glucopyranoside-3′-O-β-D-glucopyranoside (1), quercetin 3-methyl ether-7-O-α-L-rhamnopyranosyl-(1→6)-(2″-p-coumaroyl)-β-D-glucopyranoside (2), acacetin 7-O-(6″-p-coumaroyl)-β-D-glucopyranoside (3), along with five known flavonoids, one phenolic derivative, and three megastigmane glycosides. Their structures were established on the basis of detailed spectral analysis. All isolated compounds were tested for their antioxidant activity on DPPH stable radical, superoxide anion, metal chelating activity, and DNA cleavage induced by the photolysis of H2O2. Quercetin 3-O-(6″-caffeoyl)-β-D-glucopyranoside-3′-O-β-D-glucopyranoside (1), quercetin 3′-methyl ether-3-O-α-L-rhamnopyranoside (4), and 4″'-methyl ether amenthoflavone (9) exhibited the highest antioxidant capacity being also able to modulate hydroxyl radical formation more efficiently than other compounds acting as direct hydroxyl radical scavengers and chelating iron.
Molecular Identification of Panax ginseng C.A. Meyer in Ginseng Commercial Products
Authors: Del Serrone Paola , Attorri Lucilla , Gallinella Bruno , Gallo Francesca Romana , Federici Elena , Palazzino Giovanna
Published: March 2019

Molecular techniques (PCR and RFLP) were used to verify the presence of Panax ginseng C.A. Meyer in commercial products containing ginseng. DNA, extracted from four vegetable forms present in marketed products, was amplified with 18df/28ccr primers. The RFLP of the DNA amplified products, obtained using Inf I, Sau 3A1 and Taq I endonucleases, allowed the identification of P. ginseng and its differentiation from P. quinquefolium. P. ginseng was detected in 9 out 16 samples tested which, according to the declaration on the labels, contained the drug. Negative results were obtained for products containing the dried extract of the drug. A comparison of the results acquired using the molecular techniques with those using HPLC is also reported.
Non-nitrogenous Plant-derived Constituents with Antiplasmodial Activity
Authors: Bilia Anna Rita
Published: March 2019

The paper is a compilation of the studies reported in the literature concerning non-nitrogenous natural constituents that have shown antiplasmodial activity and aims to provide a basis for further in vivo studies as well as for clinical trials to develop new antimalarial agents. Due to the increasingly unsatisfactory outcomes for N-heterocyclic drugs, coupled with the rising incidence of the deadly falciparum malaria, the advent of non-nitrogenous lead compounds is timely, signaling a new era of antimalarial chemotherapy. Currently a few non-nitrogenous molecules are used in therapy, but many promising molecules of plant origin are under study, such as peroxide sesquiterpenes, quinoid triterpenes, quassinoids, gallic acid derivatives, lignans, flavonoids and biflavonoids, xanthones, naphthoquinones and phenylanthraquinones. Many of these constituents are isolated from plants used traditionally to treat malaria and fever. Ethnopharmacology can still be considered as a rich source of lead molecules.
Three Pregnane Glycosides from Pergularia Pallida
Authors: Srivastava Sangeeta , Khare Naveen K. , Khare Anakshi
Published: March 2019

Three new pregnane glycosides designated as pergulinine, pallicine and pallicinine have been isolated from the chloroform soluble extract of Pergularia pallida. On the basis of chemical and spectroscopic evidence their structures were established as drevogenin P-3-O-α-L-rhamnopyranosyl-(1→4)-O-β-D-cymaropyranoside, cissogenin-3-O-β-D-oleandropyranoside and calogenin-3-O-α-L-diginopyranosyl-(1→4)-O-β-D-digitoxopyranoside, respectively.
Isoquinoline Alkaloids from the Leaves of Dehaasia Hainanensis
Authors: Chen Chien-Kuang , Chen Su-Chang , Chen Chung-Hsiung , Lee Shoei-Sheng
Published: March 2019

This study was aimed at investigating the alkaloids present in the leaves of Dehaasia hainanensis. Thirteen isoquinolines were isolated and characterized. Of these, four aporphines [(+)-laurolitsine, (+)-corydine, (+)-laurotetanine and (+)-lindcarpine], two morphinans [(-)-sinoacutine and (-)-ocobotrine], four benzylisoquinolines [(+)-reticuline, (+)-roefractine, (+)-reticuline N-oxide, and O-methylarmepavine], and one bisbenzylisoquinoline [(-)-N,N'-dimethyllindoldhamine] are reported for the first time from Dehaasia species. The structures were elucidated by spectral analysis.
Essential Oil Composition of the Umbels and Fruit of Prangos Uloptera DC
Authors: Nazemiyeh Hossein , Razavi Seied M. , Delazar Abbas , Hajiboland Rogaieh , Mozaffarian Valiollah , Nahar Lutfun , Sarker Satyajit D.
Published: March 2019

The composition of the essential oils of the umbels and fruit of Prangos uloptera, an indigenous Iranian medicinal plant, was determined by GC-MS analyses. A total of 10 and 18 compounds were identified, respectively, from the essential oils of the umbels and the fruit. The identified compounds represented, respectively, 93.2% and 83.0% of the total essential oils. While the main components of the umbels oil were α-pinene (31.78%), β-bourbonene (15.9%), α-curcumene (10.65%), spathulenol (9%) and m-cymene (5.51%), those of the fruit oil were α-pinene (14.98%), β-bourbonene (7.81%), α-humulene (7.74%), germacrene B (7.23%) and n-tetracosane (6.65%).
Steroidal Saponins and Sapogenins from the Agavaceae Family
Authors: Simmons-Boyce Joanne L. , Tinto Winston F.
Published: March 2019

Plants belonging to the family Agavaceae are used in folkloric medicinal practices worldwide and chemical investigations of these plants have shown that they are an abundant source of steroidal saponins and sapogenins. Despite the large number of secondary metabolites isolated from this family so far, there have been few reports on the bioactivity of these compounds. This article provides a comprehensive review of the steroidal constituents of plants from the genera Agave, Cordyline, Dracaena, Furcraea, Nolina, Sansevieria and Yucca up to June 2006, and reports on the bioactivity of these compounds where available.
Phytochemical Analysis and Comparison for Differentiation of Boswellia Carterii and B. Serrata
Authors: Hanuš Lumír O. , Moussaieff Arieh , Řezanka Tomáš , Abu-Lafi Saleh , Dembitsky Valery M.
Published: March 2019

Frankincense (Boswellia carterii) and olibanum (B. serrata) were chemically analyzed to determine compounds that would enable the differentiation of the two products. Typical compounds for both species were identified. Three new compounds, 24-noroleana-3,9(11),12-triene, 24-norursa-3,9(11),12-triene, and 24-norursa-3,12-diene-11-one, were identified in olibanum; these may be either naturally occuring or pyrolytic products.
Occurrence, Biosynthesis, Biological activity and NMR Spectroscopy of D and B, D Ring Seco-limonoids of Meliaceae Family
Authors: Narender Tadigoppula , Khaliq Tanvir , Shweta  , Reddy Kancharla P. , Sharma Ravi K.
Published: March 2019

Limonoids are modified tetranortriterpenoids, classified on the basis of which of the four rings (A, B, C and D) in the intact triterpene nucleus have been oxidized. The order Rutales produces a variety of seco-limonoids, such as A, B, C, D, AB, AD, and BD-ring seco-limonoids. The Meliaceae family, belonging to the order Rutales, has yielded several D-ring and B, D-ring seco-limonoids This review describes the occurrence, biosynthesis, biological activity and NMR spectroscopy of D ring seco-limonoids, such as gedunin derivatives and B, D-ring seco-limonoids, such as methyl angolensates, xyloccensins, methyl meliacates, phragmalins and modified phragmalins. The literature from 1990 to 2005 is reviewed.
Oleanane-type Triterpene Glycosides from Glycyrrhiza Uralensis
Authors: Li-Yang Jinwei , Nakajima Jun-ichiro , Kimura Nobuhito , Saito Kazuki , Seo Shujiro
Published: March 2019

Chemical investigation of the roots of Glycyrrhiza uralensis resulted in the isolation of six oleanane-type triterpene glycosides (1 – 6), including one new saponin (1) and two (2 and 3) obtained as natural products for the first time. The new licorice saponin (1) was identified as 22β–acetoxylglycyrrhizin from [α]D, mass spectrometric, and UV, IR, and NMR spectroscopic data.. Full assignments of 1H and 13C-NMR data for compounds 2, 3, 4, 5 and 6 were made for the first time according to 2D NMR methods.
Identification of Ellagic Acid Derivatives from Stem Bark of Syzygium Guineense (Myrtaceae)
Authors: Djoukeng Jules Desire , Abou-Mansour Eliane , Tapondjou Leon Azefack , Lontsi David , Tabacchi Raffaele
Published: March 2019

An LC-DAD-ESI-MSn technique was developed to investigate crude extracts of the stem bark of S. guineense for phenolic compounds. Ellagic acids were detected on the basis of their UV absorption spectra and ESI-MS fragmentation patterns. Six ellagic acid conjugates in the complex extract of S. guineense were identified. With the aim to confirm the structures, further purification of the extract afforded the known 3-O-ellagic acid-4′-O-α-rhampyranonosides (3), two new ellagic acid rhamnopyranosides, 3-O-methylellagic acid-4′-O-α-2″-O-acetylrhamnopyranoside (4) and 3-O-methylellagic acid-4′-O-α-3″-O-acetylrhamnopyranoside (6). The structures were identified on the basis of 1D- and 2D- NMR, IR, and UV spectroscopic and mass spectrometric data. The HMBC and NOESY data of these compounds were most useful for determination of their structures. Radical scavenging activities were evaluated in the 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. Compounds 3, 4 and 6, with IC50 values of 6.1 ± 0.5, 5.8 ± 0.4, and 6.2 ± 0.4 μM, respectively were as active as ellagic acid (1) (IC50 = 4.9 ± 0.3 μM) and more active than catechin (IC50=10.8 ± 0.3 μM).
The Phytoalexins from Brassicaceae: Structure, Biological Activity, Synthesis and Biosynthesis
Authors: Pedras M. Soledade C. , Zheng Qing-an , Sarma-Mamillapalle Vijay K.
Published: March 2019

The structures, biological activity, synthesis and biosynthesis of crucifer phytoalexins are reviewed.
New reports on surface flavonoids from Chamaebatiaria (Rosaceae), Dodonaea (Sapindaceae), Elsholtzia (Lamiaceae), and Silphium (Asteraceae)
Authors: Wollenweber Eckhard , Roitman James N.
Published: March 2019

Lipophilic exudates of one species each of Chamaebatiaria and Elsholtzia, two species of Silphium and four Dodonaea species were analyzed for flavonoid aglycones. In addition to a number of well-known and widely distributed flavonoids, several very rare and one novel natural flavonol were isolated and identified. 1H and 13C NMR data of four flavanones and two flavones are reported.
Correlation between Chemical Composition of Greek Essential Oils and their Antibacterial Activity against Food-borne Pathogens
Authors: Chorianopoulos Nikos G. , Evergetis Epameinontas T. , Aligiannis Nektarios , Mitakou Sofia , Nychas George-John E. , Haroutounian Serkos A.
Published: March 2019

The compositions of forty-nine essential oils obtained from plants growing in areas of biodiversity in Greece were determined by means of gas chromatography and gas chromatography–mass spectrometry. The in vitro antibacterial activities of the oils were evaluated against a panel of five common food-borne bacteria ( Escherichia coli 0157:H7 NCTC 12900, Salmonella Enteritidis PT4, Staphylococcus aureus ATCC 6538, Listeria monocytogenes Scott A and Bacillus cereus FSS 134). Monoterpene hydrocarbons, phenolic monoterpenes and alcohols were the major constituents of the oils, but their concentrations varied greatly between the samples examined. The essential oils obtained from the species endemic to Greece ( Satureja and Origanum) had the most potent bactericidal properties. The chemical composition data were statistically processed through Principal Component Analysis (PCA) and correlated with the antibacterial activities, allowing a rough estimation of the potential of the essential oils antibacterial activity.
Chemotaxonomic Significance of the Balkan Achillea Volatiles
Authors: Radulovic Niko , Zlatković Bojan , Palic Radosav , Stojanovic Gordana
Published: March 2019

The present review describes and discusses the chemistry and chemotaxonomic implications, as well as hypothetical biogenetic considerations, of the essential oils isolated from 23 taxa of Balkan Achillea using multivariate statistical analysis.
The Steroidal Glycosides of Allium waldsteini G. Don
Authors: Eristavi Lina , Gugunishvili Darejan , Gvazava Lili
Published: March 2019

Three steroidal compounds were isolated from the air-dried, pulverized, over ground parts of Allium waldsteini G. Don, and, on the basis of physical and chemical investigations, their structures were elucidated as (25 R)-spirost-5-ene-1β,3β-diol 1-0-[α-Lrhamnopyranosyl.(1→2)-α-L-arabinopyranoside], (25R)-spirost-5-ene-1β,3β-diol 1-0-[β-D-glucopyranosyl.(1→3)-α-Lrhamnopyranosyl.(1→2)-α-L-arabinopyranoside] and 26-0-β-D-glucopyranosyl-(22R,25R).furost-5-ene-1β,3β,22α,26-tetrol 1-0-[α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside].
Biocatalytic Studies of the Furanocoumarins Angelicin and Chalepensin
Authors: Orabi Khaled Y. , El Sayed Khalid A.
Published: March 2019

Bioconversion studies conducted on the furanocoumarins angelicin and chalepensin have revealed that angelicin was metabolized by Lipomyces lipofer (ATCC 10742) to give the corresponding reduced acid 3 and chalepensin was transformed by Cunninghamella blakesleeana (SC-2138) to give the diol metabolite 4. The structures of the new metabolites have been established on the basis of spectral data. The absolute stereochemistry around C-2″ in 4 was confirmed by Horeau's method. Angelicin and chalepensin were shown to possess antifungal activity against Candida albicans and Cryptococcus neoformans.
Chemical Composition and Antibacterial Activity of Essential Oil of Anvillea radiata Coss. & Dur
Authors: Hanbali Fadwa El , El Hakmaoui Ahmed , Mellouki Fouad , El Rhaffari Lahoussine , Akssira Mohamed
Published: March 2019

The essential oil of the aerial parts of Anvillea radiata Coss. & Dur. was examined by GC-MS. Twenty-nine constituents were identified, representing 88.8% of the total. 6-Oxocyclonerolidol (66.6%) and 6-hydroxycyclonerolidol (11.4%) were found to be the major components. The disc diffusion method, used for antimicrobial activity testing, showed that the essential oil had a significant antibacterial activity against all tested microorganisms.
Analysis of Ginsenosides in Ginseng Drugs Using Liquid Chromatography-Fourier Transform Ion Cyclotron Resonance Mass Spectrometry
Authors: Tanaka Ken , Kubota Masayuki , Zhu Shu , Sankawa Ushio , Komatsu Katsuko
Published: March 2019

Analysis of ginsenosides in five Ginseng drugs derived from Panax ginseng (white ginseng), P. quinquefolius, P. japonicus produced in Japan, P. notoginseng, and P. vietnamensis using Liquid Chromatography-Fourier Transform Ion Cyclotron Resonance Mass Spectrometry (LC-FTICR-MS) was performed. Ginsenosides in the drugs were identified by the molecular formula obtained from high-resolution mass data and multiple stage MS/MS analysis. Twenty-six known ginsenosides were identified as the major constituents in the extracts of the Ginseng drugs. The five Ginseng drugs showed different reconstructed mass chromatographic profiles and were discriminated from each other.
Distribution of Iridoid Glucosides in Plants from the Genus Lippia (Verbenaceae): An investigation of Lippia alba (Mill.) N.E. Brown
Authors: Filho José G. Sena , Duringer Jennifer M. , Uchoa Daniel E. A. , Xavier Haroudo S. , Filho Jose M. Barbosa , Filho Raimundo Braz
Published: March 2019

The distribution of iridoid glucosides in plants from the genus Lippia (Verbenaceae) is described. In the present work, three known iridoids (theviridoside, mussaenoside and gardoside) were isolated from the roots of L. alba and were confirmed by NMR (1H and 13C) spectroscopic data. This information was combined with previous work on seven other Lippia species (obtained through a literature review) to give a thorough account of the iridoid glucosides currently found in this genus.
Occurrence of Sulfur-Containing Fatty Acids in Allium sativum
Authors: Dembitsky Valery M , Abu-Lafi Saleh , Hanuš Lumír O
Published: March 2019

The occurrence of saturated (14:0, 15:0, 16:0, and 18:0), and unsaturated (7–16:1, 7–18:1, 9–18:1, 9,12–18:2, 9,12,15–18:3) acids, together with novel cyclic sulfur-containing fatty acids in garlic ( Allium sativum) is reported. Organosulfur compounds, fatty acids, and sulfur-containing fatty acids were separated and characterized by GC–MS with serially coupled capillary columns with consecutive nonpolar and semipolar stationary phases.
A Cytotoxic and Hepatoprotective Agent from Withania somnifera and Biological evaluation of its Ester Derivatives
Authors: Saxena Mohit , Faridi Uzma , Srivastava S.K. , Darokar M. P. , Mishra Rupal , Pal Anirban , Shisodia Brijesh , Khanuja S. P. S.
Published: March 2019

Detailed chemical investigation of Withania somnifera roots resulted in the isolation and identification of a cytotoxic and hepatoprotective agent, palmitic acid (1), which was converted to eight semi-synthetic ester derivatives 2–9. t-Butyl palmitate (8) and amyl palmitate (9) were 4–6 times more active than 1 against adherent and suspension colon cancer cell lines. Interestingly, palmitic acid (1) and its ester derivatives 2–9 also showed hepatoprotective activity which is being reported for the first time.
Preparative Isolation of a Novel Flavonoid from an Infusion of Byrsonima basiloba Leaves by High-Speed Counter-Current Chromatography
Authors: Sannomiya Miriam , Figueiredo Maria E. , da Silva Marcelo A. , Rodrigues Clenilson M. , dos Santos Lourdes C. , Souza-Brito Alba R. M. , Vilegas Wagner
Published: March 2019

A method for the isolation of three compounds from the infusion of leaves of Byrsonima basiloba A. Juss. by high-speed counter-current chromatography (HSCCC) was developed. This technique led to the separation of a novel compound, quercetin 3- O-α-L-rhamnopyranosyl-(1→3)- O-[α-L-rhamnopyranosyl-(1→6)]-β-D-allopyranoside, and two known compounds quercetin-3- O-α-L-rhamnopyranosyl-(1→6)-β-D-galactopyranoside and (+)-catechin in 4 h with purities of over 92%. The structures of the compounds were determined by one- and two-dimensional NMR spectroscopy and HPLC.
Cytotoxicity and Brine Shrimp Lethality of Rotenoids and Extracts from Sarcolobus globosus
Authors: Wangensteen Helle , Alamgir Mahiuddin , Rajia Sultana , Meza Trine J. , Samuelsen Anne Berit , Malterud Karl E.
Published: March 2019

The present study was performed to examine the brine shrimp toxicity and cytotoxic effect of the mangrove plant Sarcolobus globosus. The Et2O and EtOAc extracts were toxic to brine shrimp larvae (LC50 = 1.6 and 4.0 μg/mL) and Caco-2 cells (IC50 = 6.7 and 21.2 μg/mL). Three rotenoids isolated from S. globosus, tephrosin, sarcolobin and 12a-hydroxyrotenone, showed high toxicity in the brine shrimp assay with LC50 values of 2.2, 2.8 and 1.9 μM, respectively.
Design, Synthesis and Fungicidal Activity of Novel (E)-Methyl 2-{2-[(coumarin-7-yloxy)methyl]phenyl}-3-methoxyacrylates
Authors: Liu Chang-Ling , Li Miao , Guan Ai-Ying , Zhang Hong , Li Zheng-Ming
Published: March 2019

A number of 7-hydroxycoumarins (5), on treatment with one equivalent of ( E)-methyl 2-{2-[(chloromethyl)phenyl]}-3-methoxyacrylate (6) at 80°C for 6–8 h, afforded ( E)-methyl 2-{2-[(coumarin-7-yloxy)methyl]phenyl}-3-methoxyacrylates (2) in 80–85% yields. The 7-hydroxycoumarins (5) were in turn prepared from resorcinols (3) and substituted ethyl 3-oxopropanoate (4). Subsequently, results of biological activities evaluated in the greenhouse indicated that several of these compounds have good fungicidal activity against cucumber downy mildew (CDM) at 25g ai/ha.
Ailanthus Quassinoids and Their Biological Activity
Authors: Joshi Bipin Chandra , Sharma Ram Prakash , Khare Anakshi
Published: March 2019

Ailanthus is an important genus of the Simaroubaceae family that is widely distributed in Asia and north Australia, and which is used in folk medicines. The plants of this genus have numerous therapeutic applications and have, therefore, been the subject of extensive chemical examination. The genus is a rich source of quassinoids, and more than 60 have been identified so far from this genus. Those reported to date have been compiled in this review, together with bioactivity data in an effort to show the rapid development in the phytochemistry and therapeutic applications of the Ailanthus species.
A New Triterpenoidal Saponin and a Flavone Glycoside from Stachys parviflora
Authors: Ahmad Viqar Uddin , Arshad Saima , Bader Sadia , Ahmed Amir , Iqbal Shazia , Khan Afsar , Khan Saleha Suleman , Tareen Rasool Bakhsh
Published: March 2019

A new triterpenoidal saponin, stachyssaponin C (1), identified as 3β, 15α, 21β-trihydroxy-olean-12-ene-28-oic acid 3- O-[α-L-rhamnopyranosyl-(1→3)- O-6″- O-acetyl-β-D-glucopyranosyl-(1→2)- O-β-D-glucopyranoside] and a flavone glycoside stachyfloroside A (2), characterized as 5,8-dihydroxy-2-(3′-hydroxy-4′-methoxy)-7 [(6″”- O-acetyl-β-D-allopyranosyl-(1→2)- O-α-D-glucopyranosyl-(1→2)- O-β-D-glucopyranosyl)oxy]-4H-1-benzopyran-4-one, were isolated from the n-butanol extract of Stachys parviflora (Lamiaceae). The structures were elucidated by extensive spectroscopic (especially 2D NMR) experiments.
Flavonoids and Triterpenoid Saponins from Pimenta dioica (Merr.) L
Authors: Moharram Fatma A. , Mohamed Mona A , Marzouk Mohamed SA , Aboutabl Elsayed A
Published: March 2019

The defatted and desalted 80% methanolic extract of the leaves of Pimenta dioica (Mirr.) L. resulted in the isolation of three triterpenoid saponins, 23-hydroxy-3α-[( O-α-L-rhamnopyranosyl-(1→2)- O-α-L-arabinopyranosyl) oxy] olean-12-en-28-oic acid O-α-L-rhamnopyranosyl-(1→4)- O-β-D-galactopyranosyl-(1→6)- O-β-D-galactopyranosyl ester (1), 2α,3α,23-trihydroxyolean-12-en-28-oic acid O-β-D-glucopyranosyl ester (2), and 2α,3α,23-trihydroxyolean-13(18)-en-28-oic acid O-β-D-glucopyranosyl ester (3), along with a novel dihydrokaempferol glucoside, namely, 3-carboxy-6,8-di- C-methyl-dihydrokaempferol 3- O-β-D-glucopyranoside (4), together with three known flavonoids, quercetin 3- O-β-D-glucuronopyranoside (5), quercitrin (6) and mernesitin (7), all for the first time from the genus Pimenta. The structures were identified on the basis of chemical and physicochemical analysis (UV, HRESI-MS, 1 and 2D NMR).
Two New Flavonoid Glycosides from the Fern Dryopteris villarii
Authors: Imperato Filippo
Published: March 2019

During a search for new flavonoids, two new natural products identified by chemical and spectral methods as quercetin 3- O-(2″,3″,6″-triacetylglucoside) and apigenin 4′- O-(6″- p-coumaroylglucoside) have been found in the fern Dryopteris villarii. In addition a new fern constituent (kaempferol 3- O-(6″-acetylglucoside)-7- O-rhamnoside) together with kaempferol 3, 7-di- O-rhamnoside have been identified in this fern. Dryopteris villarii is the only Dryopteris species having a number of acylated flavonoid glycosides.