bluuebunny/crossref_metadata_2025 huggingface dataset:
The Effect of Cinnamtannin B1 on Cell Proliferation and Glucose Uptake of 3T3-L1 Cells
Authors: Taher Muhammad , Majid Fadzilah Adibah Abdul , Sarmidi Mohamad Roji
Published: March 2019

The effects of cinnamtannin B1 on cell proliferation and glucose uptake of 3T3-L1 cells were examined. Cinnamtannin B1 promoted cell proliferation of 3T3-L1 adipocytes at a concentration range between 0.11-0.17 mM. The effect of cinnamtannin B1 on cellular 2-deoxy-D-[1-3H] glucose uptake in differentiated 3T3-L1 adipocytes, following treatment with a 0.11 mM concentration of cinnamtannin B1 for 15, 30 and 60 minutes, was an increase in the glucose uptake from a basal value to 702.0, 1111.0 and 2226.0 cpm, respectively (p<0.005). The comparable glucose uptakes with insulin treatment were 660.0, 1039.0 and 2135.0 cpm, respectively. Wortmannin and cytochalasin B were found to inhibit cinnamtannin B1-stimulated glucose uptake, but sodium orthovanadate increased the glucose uptake.
Naturally Occurring 1,1′-Trimethylenebisuracil from the Marine Sea Hare Dolabella Auricularia
Authors: Narender Tadigoppula , Khaliq Tanvir , Srivastava M. N.
Published: March 2019

From the marine sea hare Dolabella auricularia, along with the RNA nucleobase, uracil (2), an unusual bisuracil analogue, 1,1′-trimethylenebisuracil (1) has been isolated and its structure established by extensive 1D NMR, 2D NMR and IR spectroscopic and mass spectrometric data.
Leaf Essential Oil Composition of Five Species of Beilschmiedia from Monteverde, Costa Rica
Authors: Setzer William N. , Haber William A.
Published: March 2019

The leaf essential oils of five species of Beilschmiedia from Monteverde, Costa Rica (Beilschmiedia alloiophylla, B. brenesii, B. costaricensis, B. tilaranensis, and an undescribed Beilschmiedia species “chancho blanco”) have been obtained by hydrodistillation and analyzed by GC-MS in order to discern the differences and similarities between the volatile chemical compositions of these species. The principal constituents of B. alloiophylla leaf oil were germacrene D (18.9%), cis- and trans-β-ocimene (18.8% and 9.3%, respectively), α-pinene (11.8%), and bicyclogermacrene (9.1%). The leaf oil of B. brenesii was composed largely of the sesquiterpenes germacrene D (19.3%), β-caryophyllene (13.4%), α-copaene (9.0%), α-humulene (8.1%), and δ-cadinene (5.8%), and the carbonyl compounds 2-undecanone (12.8%), trans-2-hexenal (8.8%), and 2-tridecanone (3.8%). α-Bisabolol (72.1%) dominated the leaf oil of B. costaricensis, while B. tilaranensis had germacrene D (54.9%), β-caryophyllene (14.8%), and δ-cadinene (5.1%) as major components. Beilschmiedia “chancho blanco” leaf oil was composed largely of β-caryophyllene (16.6%), bicyclogermacrene (14.1%), and α-pinene (12.1%).
Antibacterial Activity of the Essential Oil of Lippia oreganoides against Multiresistant Bacterial Strains of Nosocomial Origin
Authors: Velasco Judith , Rojas Janne , Salazar Poema , Rodríguez Mariseg , Díaz Tulia , Morales Antonio , Rondón María
Published: March 2019

Antibacterial activity of the essential oil of Lippia oreganoides was evaluated against thirty-nine multiresistant bacterial strains of nosocomial origin and five reference bacterial strains using the disk diffusion agar method. The results obtained have revealed strong antibacterial activity against methicillin resistant Staphylococcus aureus, extended spectrum β-lactamase producing Klebsiella pneumoniae, and multiresistant Acinetobacter baumannii with MIC values ranging from 20 to 40 μg/mL. The low dose antibacterial activity observed in this investigation suggested that the essential oil of L. oreganoides could be used in pharmaceutical preparations for the treatment of infections caused by multiresistant bacteria. According to the literature consulted, this is the first time that antibacterial activity of this species against multiresistant bacterial strains of nosocomial origin has been reported.
Antiproliferative Sesquiterpenes from the Red Sea Soft Coral Sarcophyton Glaucum
Authors: Sawant Swapnali S. , Youssef Diaa T.A. , Sylvester Paul W. , Wali Vikram , Sayed Khalid A. El
Published: March 2019

The Red Sea soft coral Sarcophyton glaucum was investigated for its sesquiterpene content. A novel 1,2-dioxolane sesquiterpene alcohol, dioxosarcoguaiacol (1) along with the known (+)-alloaromadendrene are reported. The structure of the new sesquiterpene was determined on the basis of extensive spectral analyses. (+)-Alloaromadendrene showed potent inhibition of the proliferation of the highly malignant + SA mammary epithelial cells at a dose of 20μM.
Two Salonitenolide Derivatives from the Aerial Parts of Centaurea Gigantea Inhibit the Growth of Colorectal Cancer Cells in Vitro
Authors: Shoeb Mohammad , Celik Sezgin , Nahar Lutfun , MacManus Stephen M. , Kong-Thu-lin Paul , Jaspars Marcel , Sarker Satyajit D.
Published: March 2019

The cytotoxic activity of two salonitenolide derivatives, 8-O-(3-hydroxy-2-methylpropanoyl)-salonitenolide (or arctiopicrin, 1) and 8-O-(4-hydroxy-3-methylbutanoyl)-salonitenolide (2), isolated and identified from the methanol extract of the aerial parts of Centaurea gigantea, was assessed by the MTT cytotoxicity assay using the colon cancer cell line, CaCo-2. The IC50 values for 1 and 2 were found to be 8.5 and 26.4 μM, respectively.
Umbraculolide E, A New Briarane Diterpenoid from the Gorgonian Gorgonella Umbraculum
Authors: Anjaneyulu Ammanamanchi S.R. , Rao Vadali Lakshmana , Sastry Vedula Girija , Rao Desiraju Venkata , Laatsch Harmut
Published: March 2019

A new briarane diterpenoid, umbraculolide E (1) has been isolated from the gorgonian Gorgonella umbraculum besides the known briarane diterpenoids, juncellin, umbraculolides A and D, and a steroid 22-acetoxy-3,25-dihydroxy-16-24,20-24-bisepoxy-(3β,16α, 20S, 22R, 24S)-cholest-5-ene. The structures of the compounds were elucidated from their spectral data.
A New Strychnos Alkaloid from Strychnos Scheffleri
Authors: Tchinda Alembert T. , Tane Pierre , Sterner Olov
Published: March 2019

A phytochemical investigation of the stem bark of Strychnos scheffleri resulted in the isolation of a new strychnos alkaloid Na-deacetylmalagashine (1) together with the known derivative malagashine (2). Elucidation of the structures was based mainly on 1D and 2D NMR and MS studies and by comparison with related compounds.
Anti-leishmanial Activity of Justicidone and its Synthetic Precursors
Authors: Boluda Carlos José , Piñero José , Romero Marialina , Cabrera-Serra María Gabriela , Valladares Basilio , Aragón Zulma , López Hermelo , Pérez José A. , Trujillo Juan M.
Published: March 2019

Justicidone, a C-5, C-8 dioxo-lignan of the arylnaphthalene type isolated from Justicia hyssopifolia, and its synthetic precursors were tested for the activity against Leishmania braziliensis and Leishmania amazonensis promastigotes in vitro. Justicidone showed activity against L. braziliensis with an IC50 of 181.90 μM, while, the diasteromeric mixture of one of its synthetic precursors exhibited activity against both parasite strains with an IC50 of 99.27 μM (L. braziliensis) and 181.75 μM (L. amazonensis). This activity has not previously been reported for dibenzylbutyrolactones and dioxo-lignans.
Anti-Babesial Compounds from Berberis Vulgaris
Authors: Elkhateeb A. , Yamada K. , Takahashi K. , Matsuura H. , Yamasaki M. , Maede Y. , Katakura K. , Nabeta K.
Published: March 2019

Extracts of nine North African medicinal plants have been evaluated for their anti-babesial properties in vitro. The extracts of Berberis vulgaris and Rosa damascena showed more than 90% inhibition of the parasite growth at a test concentration of 100 μg/mL. In addition to berberine alkaloids, we isolated nine active ingredients from B. vulgaris: E-coniferyl alcohol, (-)-simulanol, p-hydroxybenzaldehyde, 3-hydroxy-4,5-dimethoxybenzoic acid, trans-ferulic acid, syringic acid, vanillic acid, cis-ferulic acid, and syringaresinol-β-D-glucoside. These compounds are all known, but are newly reported for B. vulgaris. Among them, trans-ferulic acid showed the lowest IC50 value (7.33 μg/mL), not much above that of the standard drug, diminazene aceturate (0.60 μg/mL).
Antibacterial Activity of the Crude Extract and Constituents of Vismia Baccifera Var. Dealbata (Guttiferae) Collected in Venezuela
Authors: Salas Fabiola , Velasco Judith , Rojas Janne , Morales Antonio
Published: March 2019

The antibacterial activities of the crude extract of Vismia baccifera var. dealbata Triana & Planch and of compounds isolated from it (sesamin, friedelin and vismiaquinone) were evaluated against Staphylococcus aureus (ATCC 25923), Enterococcus faecalis (ATCC 29212), Escherichia coli (ATCC 25992), Klebsiella pneumoniae (ATCC 23357), and Pseudomonas aeruginosa (ATCC 27853) using the disc diffusion agar method. The results obtained have revealed antibacterial activity against S. aureus, E. faecalis and P. aeruginosa, pathogen opportunists that become resistant to the antibiotics frequently used. According to the literature consulted, this is the first report of the antibacterial activity of the crude extract of V. baccifera and its constituents.
Anhydrous Titanium(III) chloride as a New Lewis-Acid Catalyst for Ring Opening of Epoxides with Aromatic Amines
Authors: Bhatt Suchitra , Nayak Sandip K.
Published: March 2019

Anhydrous titanium(III) chloride was found to be a simple and efficient Lewis acid catalyst for ring opening of epoxides at ambient temperature. The reaction proceeded smoothly with anilines as well as azide ion as nucleophiles to give the corresponding β-amino alcohols and β-azido alcohols in moderate to good yields.
Various Dereplication Strategies Using LC-MS for Rapid Natural Product Lead Identification and Drug Discovery
Authors: Sashidhara Koneni V , Rosaiah Jammikuntla N
Published: March 2019

Natural products are the most consistently successful source of drug leads. The rapid identification of known compounds from natural product extracts, or ‘dereplication’, is an important step in an efficiently run drug discovery program. Modern spectroscopic methods have largely revolutionized compound identification and tremendously accelerated the pace at which isolated compounds can be identified. Dereplication strategies use analytical techniques and database searching to determine the identity of an active compound at the earliest possible stage in the discovery process. This prevents wasted effort on samples with no potential for development and allows resources to be focused on the most promising lead. In the past few years, advances in technology have allowed the development of tandem analytical techniques, such as HPLC-PDA, LC-MS, LC-MS-MS, LC-NMR, and LC-NMR-MS. This review describes the principles and performance of a number of hyphenated techniques involving LC-MS that can be used for dereplication of natural products for rapid lead identification.
Functional Expression and Characterization of Trichome-Specific (-)-Limonene Synthase and (+)-α-Pinene Synthase from Cannabis sativa
Authors: Günnewich Nils , Page Jonathan E. , Köllner Tobias G. , Degenhardt Jörg , Kutchan Toni M.
Published: March 2019

Two recombinant, stereospecific monoterpene synthases, a (-)-limonene synthase (CsTPS1) and a (+)-α-pinene synthase (CsTPS2), encoded by Cannabis sativa L. cv. ‘Skunk’ trichome mRNA, have been isolated and characterized. Recombinant CsTPS1 showed a Km value of 6.8 μM, a Vmax of 1.1 × 10−4 μmol/min and Vmax/Km of 0.016; the pH optimum was determined at pH 6.5, and a temperature optimum at 40°C. Recombinant CsTPS2 showed a Km value of 10.5 μM, a Vmax of 2.2 × 10−4 μmol/min and Vmax/Km of 0.021; the pH optimum was determined at pH 7.0, and a temperature optimum at 30°C. Phylogenetic analysis showed that both CsTPSs group within the angiosperms and belong to the Tpsb subgroup of monoterpene synthases. The enzymatic products (-)-limonene and (+)-α-pinene were detected as natural products in C. sativa trichomes.
Biotransformation of a Monoterpene Mixture by in vitro Cultures of Selected Conifer Species
Authors: Dvořáková Marcela , Valterová Irena , Vaněk Tomáš
Published: March 2019

Biotransformation of monoterpenes is a mild and promising method for the production of stereospecific and regiospecific organic compounds. It is advantageous, especially for the preparation of substances with complicated structures and for those that need to be classed as “natural products“. Our study has focused on the biotransformation of a monoterpenic mixture, turpentine, by Picea abies and Taxus baccata suspension cultures. We identified the biotransformation products and compared the metabolite compositions of the tissue cultures. The major biotransformation products of turpentine were trans-pinocarveol, trans-verbenol, verbenone, myrtenol, α-terpineol and trans-sobrerol, which correspond with the products of biotransformation of the individual monoterpenes, α-pinene and β-pinene, by P. abies suspension culture.
Dihydroxysesquiterpenoids from Santalum insulare of French Polynesia
Authors: Butaud Jean-François , Gaydou Vincent , Bianchini Jean-Pierre , Faure Robert , Raharivelomanana Phila
Published: March 2019

Two new dihydroxysesquiterpene derivatives, elvirenol (1) and elvirol (2), along with five known compounds, (Z)-2β-hydroxy-14-hydro-β-santalol (3), (Z)-2α-hydroxyalbumol (4), (Z)-campherene-2β,13-diol (5), bisabola-2,10-dien-7,13-diol (6) and 2R-(Z)-campherene-2,13-diol (7) were isolated from the n-hexane extract of Santalum insulare (Santalaceae) from French Polynesia. Elvirol and elvirenol have a new sesquiterpene skeleton named elvirane. The structures were determined by extensive NMR studies. Compounds with antibacterial and antifungal activities identified in S. album heartwood were also present in S. insulare and may contribute to the recognized activities of this material in Polynesian traditional medicine.
Thebaine Synthase: A New Enzyme in the Morphine Pathway in Papaver Somniferum
Authors: Fisinger Ursula , Grobe Nadja , Zenk Meinhart H.
Published: March 2019

Along the poppy morphine biosynthetic pathway, the transition from salutaridinol-7-O-acetate to thebaine had previously been claimed to proceed non-enzymatically between pH 8–9. At pH 6–7, the acetate was transformed to an azonine derivative. These transformation reactions were revisited using Papaver somniferum protein extracts in search for a possible protein catalyst. After removal of residues and inhibitory low molecular weight compounds from the latex of P. somniferum, this latex serum was shown to convert salutaridinol-7-O-acetate to thebaine in high yield at the physiological pH of 7.0. A new enzyme, which was partly purified, was shown to catalyze this reaction and was partly characterized. As a result, a further enzymatic step had to be added to the morphine pathway in the poppy plant, involved in the transformation of 2 moles L-tyrosine to one mole of morphine.
Cytotoxic Xanthones from the Leaves of Garcinia Urophylla
Authors: Khalid Rozida Mohd , Jabit Md. Lip , Abas Faridah , Stanslas Johnson , Shaari Khozirah , Lajis Nordin H.
Published: March 2019

Two new xanthones, 7-hydroxydesoxymorellin (1) and isocaledonixanthone D (2), and four known ones, gaudichaudione H, 1,7-dihydroxy-3-methoxy-2-(3-methyl-2-butenyl)xanthone, 1,5-dihydroxy-3-methoxy-2-(3-methyl-2-butenyl)xanthone, and 1,3,7-trihydroxy-2-(3-methyl-2-butenyl)xanthone, as well as lupeol were isolated from the leaves of Garcinia urophylla (Guttiferae). Their structures were determined using a combination of 1D (1H NMR, 13C NMR, DEPT) and 2D (COSY, gHSQC, gHMBC) NMR spectroscopic techniques. Among the isolates, 7-hydroxydesoxymorellin (1), gaudichaudione H, 1,5-dihydroxy-3-methoxy-2-(3-methyl-2-butenyl)xanthone, and 1,3,7-trihydroxy-2-(3-methyl-2-butenyl)xanthone demonstrated cytotoxic activities against breast (MCF-7), prostate (DU-145), and lung (NCI-H460) human cancer cell lines.
A Phylogenetic Analysis of Tribes of the Asteraceae Based on Phytochemical Data
Authors: Calabria Lalita M. , Emerenciano Vicente P. , Ferreira Marcelo J. P. , Scotti Marcus T. , Mabry Tom J.
Published: March 2019

This work describes the first phylogenetic analysis of the entire Asteraceae based only on chemical data. The data matrix used in this study was based on a large chemical database comprising ~400 skeletal types of terpenes, coumarins, flavonoids, benzofurans and polyacetylenes isolated from the family. Hypotheses about the relationships among tribes are discussed based on the chemical data and compared with relationships inferred from the morphological and macromolecular based classifications.
Metabolomic Studies on the Chemical Ecology of the Xylariaceae (Ascomycota)
Authors: Stadler Marc , Fournier Jacques , Quang Dang N. , Akulov Alexander Y.
Published: March 2019

Fruiting bodies collected in the field during the vegetation period in different developmental stages and mycelial cultures of 50 representatives of xylariaceous fungi were tested for antimicrobial and nematicidal activities, and 50 of their characteristic metabolites were studied for comparison. Furthermore, analytical HPLC profiling using diode array and electrospray mass spectrometric detection was performed to identify and quantify the major constituents, revealing that up to 10% of the dry fruiting body biomass may be composed of secondary metabolites. In several species, significant antimicrobial effects were noted upon incubation of the fruiting bodies in an agar diffusion assay, i.e., without any need for extraction and concentration of active constituents. These results suggest that most of the characteristic constituents of subfamily Hypoxyloideae (i.e. Hypoxylon and related genera) are involved in non-specific defense reactions that underwent specific permutations in the course of evolutionary processes, resulting in a broad diversity of unique polyketides and other secondary metabolites.

In contrast, the fruiting bodies of representative species of Biscogniauxia and subfamily Xylarioideae generally contained no significant activities. Only cultures of most Xylarioideae exhibited antimicrobial effects, due to the presence of cytochalasins and other toxins, while extracts from cultures of Hypoxyloideae, except for Daldinia and Entonaema, were only weakly active. Cytochalasins and other yet unidentified compounds that do not constitute pigments are responsible for enhanced biological activity in maturing stromata of H. howeanum, H. rubiginosum, and H. fuscum from Alnus, whereas in H. fuscum from Corylus and further species of Hypoxylon and Annulohypoxylon, merely the concentrations of major metabolites varied during the vegetation period. Usually, the highest yields of secondary metabolites and the strongest activities were observed in the growing stromata of Hypoxyloideae, prior to or concurrent with the production of the sexual stage. These results are discussed with regard to current hypotheses on the evolution and phylogeny of the Xylariaceae.
Heliotropin, Heliotrope Odor and Tahitian Vanilla Flavor: The End of a Saga?
Authors: Joulain Daniel , Laurent Raymond , Masson Jerome , Beolor Jean-Claude , Brevard Hugues
Published: March 2019

A targeted search for heliotropin (or piperonal) in the flower fragrance of heliotrope and in cured vanilla beans of Tahitian origin is reported. Heliotropin is not detected in the fragrance emitted by heliotrope, using dynamic headspace SBSE sampling, followed by thermal desorption and analysis by conventional GC-MS. Main constituents are anisaldehyde and benzaldehyde, which confirms previous findings. Less than one part per million of heliotropin is accurately detected in authentic Tahitian vanilla bean, in using both GC-MS and LC-MS/MS. This confirms previous observations, which had shown that 4-methoxyaromatic compounds are the characteristic elements in the flavor of Tahitian vanilla, with p-anisaldehyde as the the main aroma donator. We suggest that heliotropin was named after the discovery of piperonal by degradation of piperine, the odor of which was reminiscent of the heliotrope flower. Later, its identification in vanilla extracts was the result of either a wrong interpretation of analytical data, or, much more probably, adulterations of these extracts. As a result, heliotropin should not be cited any longer as a characteristic consituent of Tahitian vanilla.
Chemical Systematization of the Genus Foeniculum Mill. Based on the Accumulation and Qualitative Differentiation of the Essential Oil
Authors: Bernáth Jenő , Németh Éva
Published: March 2019

All members of the genus Foeniculum Mill. accumulate volatiles, including terpenoid and phenylpropanoid compounds. The genus shows a large diversity from both the morphological and chemical points of view. Based on the former morpho-phenological systematization, two subspecies (subsp. piperitum and subsp. capillaceum) and three varieties (var. vulgare, var. dulce, and var. azoricum) were distinguished. As a result of detailed analysis of 185 gene-bank accessions and evaluation of literature references a more sophisticated chemical classification of the genus has been completed by us.

According to our anatomical investigations the oil ducts (vittae) appear in the early stages of development of generative organs, even at the time of bud formation. The maximum yield of essential oil and dry matter coincide with the ripening phase of the fruit, while the relative percentage of oil shows its maximum much earlier, at the beginning of fruit development, when the accumulation process of starches is just about to start. However, for the chemical classification of the genus, analysis of the oil distilled from the ripe fruits seems to be optimal because of its relative quantitative and qualitative stability.

Based on the evaluation of Foeniculum vulgare (Mill.) populations of different origin the distinction of F. vulgare subsp. piperitum seems to be a relatively simple procedure because of the unique morphological markers and the presence of piperitone and piperitone oxide, as well as the high accumulation level of limonene. Similarly, in the case of F. vulgare subsp. capillaceum var. azoricum, the relatively high level of (E)-anethole and low accumulation level of methyl chavicol helps the orientation. Three inner groups of chemovarietal rank of F. vulgare subsp. capillaceum var. dulce can be distinguished according to the accumulation level of (E)-anethole and methyl chavicol. The intra-specific chemical classification of F. vulgare subsp. capillaceum var. vulgare group raises many more difficulties. Evaluating a large number of populations, as well as the literature references, distinction of three chemovarieties [(E)-anethole, fenchone and methylchavicol types] and four chemoforms of a lower chemical rank (segregated by a different ratio of (E)-anethole and methyl chavicol) were identified.
Antitubercular Activity of Mushrooms (Basidiomycetes) and their Metabolites
Authors: Zjawiony Jordan K.
Published: March 2019

Re-emergence of multi-drug resistant and HIV-associated tuberculosis justifies the search for new anti-TB agents. Mushrooms (Basidiomycetes) and their secondary metabolites are relatively little explored in this respect. A short review of antitubercular mushrooms and their active metabolites is presented here.
Phytochemical Investigation and Anticonvulsant Activity of Paeonia parnassica Radix
Authors: Kritsanida Marina , Magiatis Prokopios , Skaltsounis Alexios-Leandros , Stables James P.
Published: March 2019

Based on traditional reports of the use of plants of the genus Paeonia in the treatment of epilepsy, we have screened extracts of the roots of three Greek Paeonia species ( P. parnassica, P. mascula subsp. hellenica, P. clusii subsp. clusii) for anticonvulsant activity. This led to the identification of some interesting prophylactic anticonvulsant activity of the extracts of P. parnassica. From the roots of this species, seventeen compounds were subsequently isolated and identified. Amongst these, seven contained the characteristic cage-like terpenic skeleton that is found only in plants of the genus Paeonia. Two of the above products: 4- O-methylpaeoniflorin (1) and paeonidanin (2) are described for the first time as natural products. The structures of all compounds have been elucidated on the basis of their spectral data.
New Oplopane-type Sesquiterpenoids from Ligularia duciformis
Authors: Tori Motoo , Fujiwara Miho , Okamoto Yasuko , Tanaka Masami , Gong Xun , Shen Yuemao , Hanai Ryo , Kuroda Chiaki
Published: March 2019

The chemical constituents of the root of Ligularia duciformis, collected in Yunnan Province of China, was studied and two new oplopane-type sesquiterpenoids were isolated, whose structures were determined on the basis of spectroscopic evidence. Quite recently, oplopane-type compounds were found in Ligularia narynensis, and this is the second example to isolate oplopane-type sesquiterpenoids from Ligularia plants.
Bisabolenes and Nor-Sesquiterpenes from Bazzania tridens
Authors: Wu Chia-Li , Chen Wei-Yu , Chu Chi-Sheng
Published: March 2019

Two bisabolene sesquiterpenes (1 and 2), two nor-sesquiterpene ketones (3 and 4) and one humulene epoxide (6) were identified from the Taiwanese liverwort Bazzania tridens. Among them, 3 was novel, and 2, 4 and 6 were reported for the first time from a natural source. Their structures were mainly elucidated by analysis of various NMR spectra.
Carbohydrate Microarray on Glass: A Tool for Carbohydrate-Lectin Interactions
Authors: Tetala K. Kishore R. , Giesbers Marcel , Visser Gerben M. , Sudhölter Ernst J. R. , van Beek Teris A.
Published: March 2019

A simple method to immobilize carbohydrates on a glass surface to obtain a carbohydrate microarray is described. The array was used to study carbohydrate-lectin interactions. The glass surface was modified with aldehyde terminated linker groups of various chain lengths. Coupling of carbohydrates with an amino terminated alkyl spacer to the aldehyde terminated glass followed by reductive amination resulted in carbohydrate microarrays. Fluorescently labeled (FI-TC) lectins (concanavalin A and Arachis hypogaea) were used to study specific carbohydrate-lectin interactions. contact angle, atomic force microscopy (AFM) and confocal laser fluorescence microscopy (CLFM) techniques were used in this study to monitor the modification of the glass and the successful selective binding of lectins to the carbohydrate microarray.
Biotransformation of Monoterpenoids by the Larvae of Common Cutworm (Spodoptera litura)
Authors: Miyazawa Mitsuo , Takechi Hiromune
Published: March 2019

Biotransformations of monoterpenoids by Spodoptera litura are reviewed. Various substrates used for the transformations are included in this review of the literature for the period 1996–2006. The metabolism of monoterpenoids in S. litura may involve the following transformation; 1) position specific hydroxylation of Me or CH2 group; 2) formation of allylic alcohol by hydroxylation; 3) C=C epoxidation followed by hydration to a vicinal diol; 4) oxidation of a primary alcohol to a carboxylic acid.
Essential Oils from Lamiaceae Species as Promising Antioxidant and Antimicrobial Agents
Authors: Mimica-Dukić Neda , Božin Biljana
Published: March 2019

Overproduction of free radicals in organisms and lipid peroxidation in cell membranes have been implicated in various pathophysiological disorders, including cardiovascular diseases, atherogenesis, mutagenesis, diabetes, etc. Furthermore, the oxidation of lipids in food, cosmetic and pharmaceutical products, together with the growth of undesirable microorganisms result in off-flavour, spoilage and deterioration, rendering such products unfit for human consumption. Increasing environmental pressure for industry to use “clean technology” and to utilize sustainable sources of materials for the manufacturing process, have concentrated recent investigations towards natural sources of antioxidants and antimicrobials. Although plant phenolics have been recognized as the most powerful natural antioxidants, recent studies suggest that terpenoids in essential oil could also contribute to the overall antioxidant capacity of many spice plants. This review summarizes the scientific evidence regarding the antioxidative and antimicrobial efficiency of essential oils of aromatic plants belonging to the Lamiaceae family, and consequently their possible utilization as safe and healthy food supplements.
Naturally Occurring Homoisoflavonoids: Phytochemistry, Biological Activities and Synthesis
Authors: Abegaz Berhanu M. , Mutanyatta-Comar Joan , Nindi Mathew
Published: March 2019

This review covers the phytochemical, biological properties, and synthesis of naturally occurring homoisoflavonoids. Homoisoflavonoids are a very important class of secondary metabolites whose numbers have grown from 20 in 1981 to 157 at the present time. They are found to occur in seven plant families. For the purpose of this review they are classified into five groups: 3-benzylchroman-4-ones, 3-benzylflavans, Δ3,9 and Δ2,3 3-benzylchroman-4-ones, benzocyclobutenes (scillascillins) and rearranged homoisoflavonoids (brazilin and related compounds). Biosynthetically, the 3-benzylchroman-4-ones and the 3-hydroxy-derivatives have been shown to arise from a chalcone precursor (sappanchalcone) and there is strong evidence that this isolable intermediate can be converted into the diverse structures such as the benzocyclobutenes (scillascillins) and the rearranged, brazilin-type compounds. Homoisoflavonoids possess a wide range of biological activities, including, antimicrobial, antimutagenic, anti-inflammatory, antidiabetic, etc, properties. The review also surveys the chemical synthesis of natural homoisoflavonoids. Analytical methods for the determination of these important metabolites are also reviewed. The last section is devoted to a brief review of the diagnostic NMR spectroscopic features of homoisoflavonoids. A comprehensive Table has also been compiled listing all known metabolites, their sources, melting points and optical rotation values (where available) and references.
The in vitro Immunomodulatory Activity of Oleuropein, a Secoiridoid Glycoside from Olea europaea L
Authors: Randon Andrew Mangion , Attard Everaldo
Published: March 2019

Oleuropein, a secoiridoid glycoside, is a potential antioxidant and antimicrobial agent. The aim of the present study was to investigate the in vitro effects of oleuropein and Olea europaea extracts on unstimulated lymphocytes. Oleuropein did not produce any significant cytotoxic effects on lymphocytes. On the contrary, it had a stimulatory effect, and was capable of inducing and maintaining high proliferation rates in lymphocytes. The stimulatory effects of oleuropein and extracts were concentration-dependent with a range of median stimulatory concentration 1 mM at 48 h. The cytotoxicity effect of oleuropein and extracts increased with time resulting in a greater cytotoxic effect on already-stimulated lymphocytes at 96 h even though dose dependence was not demonstrated. Morphological observations showed that oleuropein and extracts induced blastogenesis similar to that of phytohaemagglutinin (PHA). In fact, from lymphocyte activation studies, oleuropein exhibited a high degree of lymphocyte aggregation, which is an indicator of cell activation and proliferation.
Polyhydroxylated Steroidal Saponins from the Rhizomes of Convallaria majalis
Authors: Higano Taro , Kuroda Minpei , Jitsuno Maki , Mimaki Yoshihiro
Published: March 2019

Six new polyhydroxylated spirostanol saponins (1–6) were isolated from the methanolic extract of the rhizomes of Convallaria majalis. On the basis of extensive spectroscopic analysis, including 2D NMR data, and a few chemical transformations, the structures of 1–6 were determined to be 1β,2β,3β-trihydroxy-5β-spirost-25(27)-en-5-yl β-D-galactopyranoside (1), (25 S)-1β,2β,3β-trihydroxy-5β-spirostan-5-yl β-D-galactopyranoside (2), 1β,2β,3β,4β-tetrahydroxy-5β-spirost-25(27)-en-5-yl β-D-galactopyranoside (3), (25 S)-1β,2β,3β,4β-tetrahydroxy-5β-spirostan-5-yl β-D-galactopyranoside (4), 1β,2β,3β,4β-tetrahydroxyspirost-25(27)-en-5-yl α-L-arabinopyranoside (5), and (25 S)-1β,2β,3β,4β-tetrahydroxy-5β-spirostan-5-yl α-L-arabinopyranoside (6), respectively.
Antioxidant and XOD Inhibitory Coumarins from Pterocaulon polystachyum DC
Authors: Vera Nancy , Zampini Catiana , Isla María Inés , Bardón Alicia
Published: March 2019

The antioxidant capacity of prenyletin (6-hydroxy-7-isoprenyloxycoumarin (1), prenyletin-6-methylether (6-methoxy-7-isoprenyloxycoumarin (2), and ayapin (6,7-methylenedioxycoumarin (3), isolated from an Argentine collection of Pterocaulon polystachyum, was investigated. Compound 1 displayed a higher scavenging activity on DPPH (72%) and ABTS (89%), at 100 μg/mL, than 2 and 3. In the non-enzymatic system of O2•- generation, compound 1 scavenged (46%) superoxide radicals at a scavenging concentration (SC50) of 100 μg/mL. In addition, 1 inhibited 82% uric acid formation at 100 μg/mL, while allopurinol, employed as positive control, displayed 93% inhibition at the same concentration. The antioxidant ability of 1 is dose-dependant and apparently its OH group on C-6 is a structural requirement for the observed activity. A synergistic scavenging action of a ternary mixture (ratio 1:8:1) of 1, 2 and 3 was also observed.
Chemical Composition of the Essential Oil of Centella asiatica (L.) Urb. from Western Himalaya
Authors: Joshi Virendra P. , Kumar Neeraj , Singh Bikram , Chamoli R. P.
Published: March 2019

The chemical composition of the essential oil obtained by hydrodistillation of the whole plant of Centella asiatica (L.) Urb., growing wild in western Himalaya, was investigated by GC-FID and GC-MS on two columns of different polarities. The oil contained 73.3% of sesquiterpene hydrocarbons, comprised mainly of β-caryophyllene (23.2%), α-humulene (23.1%), trans-β-farnesene (6.3%), germacrene-D (5.4%) and caryophyllene oxide (3.3%).
Chemical Composition, Olfactory Evaluation and Antioxidant Effects of the Leaf Essential Oil of Corymbia citriodora (Hook) from China
Authors: Jirovetz Leopold , Bail Stefanie , Buchbauer Gerhard , Stoilova Ivanka , Krastanov Albert , Stoyanova Albena , Stanchev Vesselin , Schmidt Erich
Published: March 2019

The chemical composition of a sample of lemon eucalyptus essential oil ( Corymbia citriodora) from China was determined by GC/FID and GC/MS. Citronellal (76.3%), citronellol (5.7%) and neo-isopulegol (5.5%) were the major components. The odor of the sample was evaluated as fresh, citrus-like and mildly fruity, with a pleasant woody background note.

Lemon eucalyptus oil was found to exhibit antiradical activity with respect to DPPH and hydroxyl (OH•) radicals. The effect exercised on OH• radicals significantly exceeded that observed for the DPPH radical – the respective concentrations for 50% inhibition of the radicals were 0.38 μg/mL for OH• and 344.0 μg/mL for DPPH. Furthermore, the essential oil revealed antioxidant activities in a model system comprised of a linoleic acid emulsion. At a concentration of 0.1%, inhibition of conjugated dienes-formation by 59.8% was observed and the formation of secondary oxidized products of linoleic acid by 84.7%.
Phytochemistry, Pharmacology and Clinical Use of Andrographis paniculata
Authors: Samy R. Perumal , Thwin M.M. , Gopalakrishnakone P.
Published: March 2019

Andrographis paniculata (Burma f.) Wall ex Nees (Acanthaceae) is a common weed distributed throughout the tropical and subtropical regions. All parts of A. paniculata are extremely bitter in taste. This plant is well known in Siddha, Ayurvedic and traditional (tribal) systems of medicine in India. A. paniculata is used for the treatment of infectious diseases, which account for the major proportion of health problems, and which are most often used in the traditional system of medicine. The major active components of the plant are andrographiloids, which have been extensively studied in a variety of models including human clinical trials for their therapeutic effects. Moreover, A. paniculata is known to have very low toxicity in animals and humans. The plant also exhibits antifertility effects. Most of the traditional uses of the species have some scientific basis. This review is an attempt to summarize the available information on A. paniculata for further investigation.
Diversity on Diterpene Composition in Two Populations of Parentucellia viscosa: Labdane and Clerodane Chemotypes
Authors: Grande Manuel , Fernández-Mateos Alfonso , Blanco Juan José , Herrador M. Mar , del Moral José F. Quílez , Arteaga Pilar , Arteaga Jesús F. , Barrero Alejandro F.
Published: March 2019

The terpenic compositions of two populations of Parentucellia viscosa growing in the west-central and southern parts of the Iberian Peninsula have been studied. Seven labdadienes were identified from the former population, whereas the main terpenic constituents of the latter were ent-clerodadienes. The biosynthetic significance of this dramatic change in the diterpenic distribution of both populations is discussed.
Saponins and Volatile Constituents from Lonicera japonica Growing in the Western Himalayan Region of India
Authors: Kumar Neeraj , Bhandari Pamita , Singh Bikram , Kaul Vijay K.
Published: March 2019

Chemical investigation of the leaves and fresh flowers of Lonicera japonica lead to the isolation of a new pentacyclic triterpene saponin, 3- O-[α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranosyl]-hedragenin (1) along with two known saponins, 3- O-[α-L-arabinopyranosyl]-hedragenin (2) and 3- O-[α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl]-hedragenin (3), two fatty acid esters, methyl (Z,Z) 9,12-octadecadienoate (methyl linoleate) (4) and methyl (Z,Z,Z) 9,12,15-octadecatrienoate (methyl linolineate) (5) and two long chain hydrocarbons, octadecane (6) and heneicosane (7). The structures were established on the basis of IR, 1D- and 2D-NMR (HMQC and HMBC) spectroscopic and ESI-QTOF-MS/MS analysis. Simultaneously, the volatile composition of fresh flowers of L. japonica, analyzed by GC/MS, indicated the presence of two long chain hydrocarbons, heneicosane (37.5%) and octadecane (34.5%) as major constituents. Other metabolites characterized were fatty acids and their esters, such as palmitic acid (1.7%), linolenic acid (2.5 %), linoleic acid (1.3%), methyl palmitate (2.3%), methyl 9,12-octadecadienoate (4.5%) and methyl ( Z,Z,Z)-9,12,15-octadecatrienoate, along with oxygenated monoterpenes and sesquiterpenes, namely linalool, cis-linalool oxide, terpine-4-ol and trans-nerolidol.
Excelsinidine, A Quaternary Alkaloid from Aspidosperma excelsum
Authors: Layne Tanya H. , McLean Stewart , Reynolds William F. , Tinto Winston F.
Published: March 2019

A chemical investigation of Aspidosperma excelsum yielded excelsinidine (1), a quaternary indole alkaloid possessing an unusual 1-azoniatricyclo[4.3.3.0]undecane moiety, along with the known compound aspidodasycarpine (2). Structural elucidation was effected by a combination of 1D- and 2D-NMR spectroscopic techniques, along with mass spectral studies.
Coumarins from Seseli hartvigii Roots
Authors: Tosun Alev , Baba Masaki , Okuyama Toru
Published: March 2019

Three angular-type pyranocoumarins, (-)-anomalin (1), (+)-(3' R,4' R)-3′,4′-disenecioyloxy-3′,4′-dihydroseselin (2), and (-)-(3' R,4' R)-3′-angeloyloxy-4′-acetoxy-3′,4′-dihydroseselin (3), two linear-type furocoumarins, bergamottin (4) and isoimperatorin (5), and a simple coumarin, suberosin (6) have been isolated from the roots of Seseli hartvigii (Umbelliferae). The structures of these compounds were determined from spectral and physical information, and with reference to literature data.
A New Biflavonoid from Selaginella rupestris
Authors: Reddy Nimmanapalli P. , Reddy Bandi A.K. , Gunasekar Duvvuru , Blond Alain , Bodo Bernard
Published: March 2019

A new biflavanone, 7,4″’-di- O-methyltetrahydrohinokiflavone (1) together with two known biflavonoids, tetrahydrohinokiflavone (2) and amentoflavone (3) were isolated from the whole plant of Selaginella rupestris. The structures of these compounds were elucidated by 1D- and 2D-NMR spectroscopy, and by mass spectrometry.
Oxidation of Polyphenols by Extracellular Peroxidase in Suspension Cell Culture of Liverwort Heteroscyphus planus
Authors: Tjandrawaskitasari Leily , Hata Rie , Chiba Hanami , Hashimoto Makoto , Takahashi Kosaku , Nabeta Kensuke
Published: March 2019

Peroxidase secretion and activity in the oxidation of polyphenols bisphenol A (BPA, 2,2-bis(4-hydroxyphenyl)propane) and lignin model compound (LMC, guaiacylglycerol-β-guaiacylether) were observed in a suspension cell culture of liverwort Heteroscyphus planus. When BPA was co-incubated in a suspension cell culture of liverwort for 5 days, it was depleted by approximately 63%. Oxidation of BPA was observed in culture filtrates of liverwort, and most of the oxidation products were insoluble higher molecular-weight compounds (30%). The oxidative degradation products of BPA and LMC were analyzed by GC-MS and were identified by comparing their retention time and MS spectra with those of the authentic compounds. BPA was degraded to 4-isopropenylphenol and p-hydroxyacetophenone. The formation of these products was examined using [2H14]-BPA. The lignin model compound was degraded to guaiacol, vanillin, coniferyl alcohol and ferulic acid. Biphenyl dehydrodimer was detected in both the reaction mixtures of the suspension cell culture and the culture filtrates incubated with the LMC. The dimer was identified as 1,1′-(4,4′-dihydroxy-3,3′-dimethoxy-5,5′-biphenylene)- bis[8-(2″-methoxyphenoxy)-7,9-propanediol] by 1D and 2D NMR analysis. The activity of secreted peroxidase in the suspension cell culture (0.045 U/mL) was slightly enhanced by addition of LMC (0.059 U/mL), p-cresol (0.064 U/mL), and 2,6-dimethoxyphenol (0.082 U/mL) 7 days after the beginning of incubation.
Detection, Isolation and Partial Characterization of Antifungal Compound(s) Produced by Pediococcus acidilactici LAB 5
Authors: Mandal Vivekananda , Sen Sukanta K. , Mandal Narayan C.
Published: March 2019

Pediococcus acidilactici LAB 5 produces antifungal compound(s), as well as bacteriocin, which was isolated from vacuum packed fermented meat. This bacterium exhibits varying degrees of antifungal activity against a number of food and feed borne molds and plant pathogenic fungi, such as Alternaria solani, Aspergillus fumigaus, A. parasiticus, Cladosporium herbarum, Colletotrichum acutatum, Curvularia lunata, Fusarium oxysporum, Microsporium sp, Mucor sp, and Penicillium sp. The production of antifungal compound(s) showed a great degree of media specificity and it was strictly restricted to MRS agar media. No production of antifungal compounds was detected in TGE, and TGE+ Tween 80 plates, though the latter supported the highest amount of bacteriocin production at 37°C after 24 hrs. Antifungal compound produced by LAB 5 was extracted using diethyl ether. The minimum inhibitory concentration (MIC) and minimum fungicidal concentration (MFC) of the compound were determined against Curvularia lunata. Chemically the antifungal substance was a phenolic compound with aromatic unsaturation, as evidenced by UV and IR spectroscopy. This is the first report of the production of antifungal compounds by Pediococcus acidilactici LAB 5.
Chemical Composition and Antibacterial Activity of Extracts of Helleborus bocconei Ten. subsp. intermedius
Authors: Rossellia Sergio , Maggio Antonella , Formisano Carmen , Napolitano Francesco , Senatore Felice , Spadaro Vivienne , Bruno Maurizio
Published: March 2019

Helleborus bocconei Ten. subsp. intermedius (Ranunculaceae) is a Sicilian medicinal plant used for the treatment of pneumonia affecting cows and horses and for the removal of human decayed molars. The goal of our study was to assess the biological activity of Helleborus bocconei subsp. intermedius by testing its extracts for their activity against bacteria known to cause respiratory diseases. The two more active extracts (light petroleum from roots and aerial parts), as well as the dichloromethane extracts, were analyzed by GC/MS and their composition is reported.
Chemical Composition and Cruzain Inhibitory Activity of Croton draco Bark Essential Oil from Monteverde, Costa Rica
Authors: Setzer William N. , Stokes Sean L. , Bansal Anita , Haber William A. , Caffrey Conor R. , Hansell Elizabeth , McKerrow James H.
Published: March 2019

American trypanosomiasis, Chagas disease, is a great cause of human morbidity and mortality in the Neotropics. Although there is currently no effective treatment for this parasitic disease, a number of potential biochemical targets have been identified, including the cysteine protease cruzain. Croton draco Cham. & Schldl. (Euphorbiaceae), commonly known as sangre de drago, is used in traditional medicine for a number of maladies. In this study, Croton draco bark essential oil has been shown to inhibit the activity of cruzain. The bark oil has been analyzed by GC-MS and the major components found to be β-caryophyllene (31.9%), caryophyllene oxide (22.0%), 1,8-cineole (6.2%), and α-humulene (5.6%). The major components have been tested for cruzain inhibitory activity, but show minimal activity, so it is not clear if the activity of Croton draco bark oil is due to a synergistic effect of the essential oil components or due to very active minor components. Croton draco bark oil has also been tested for cytotoxic activity against a panel of human tumor cell lines, but shows little activity.
Eastern Polynesian Sandalwood Oil (Santalum insulare Bertero ex A. DC.) – a Detailed Investigation
Authors: Braun Norbert A. , Butaud Jean-François , Bianchini Jean-Pierre , Kohlenberg Birgit , Hammerschmidt Franz-Josef , Meier Manfred , Raharivelomanana Phila
Published: March 2019

Three qualities of Eastern Polynesian sandalwood oil were analyzed using GC and GC-MS. Sixty-six constituents were identified: 5 monoterpenes, 58 sesquiterpenes and 3 others. The main constituents of the essential oils were ( Z)-α-santalol and ( Z)-β-santalol. Beside chemical composition, olfactory evaluation and chiral gas chromatography of β- and epi-β-bisabolol isomers confirmed the close relationship of Eastern Polynesian to East Indian and New Caledonian sandalwood oil.
Malagasy Liverworts, Source of New and Biologically Active Compounds
Authors: Harinantenaina Liva , Asakawa Yoshinori
Published: March 2019

The phytochemical investigation of eight Jungermaniales liverwort species: Bazzania decrescens, B. madagassa (Lepidoziaceae), Plagiochila barteri, P. terebrans (Plagiochilaceae), Isotachis aubertii (Isotachidaceae), Mastigophora diclados (Lepicoleaceae), Radula appressa (Radulaceae), and Thysananthus spathulistipus (Lejeuneaceae), collected from Madagascar, has been carried out to afford new and structurally interesting terpenoids and aromatic compounds. The biological activities of the isolated secondary metabolites were determined and the herbertene-type sesquiterpenoids were shown to have antibacterial activity. A new ent-clerodane diterpene from Thysananthus spathulistipus and bis-bibenzyls-type aromatic compounds exhibited strong inhibition of NO production in RAW 264.7 cells, while marchantin C produced moderate α-glucosidase inhibition. The chemosystematics of the studied species are discussed.
The Dawn of Marine Natural Product Chemistry – the Brazilian Origin
Authors: Christophersen Carsten
Published: March 2019

The structure of a purple water-soluble pigment from the marine bryozoan, Bugula neritina, has been studied for more than 100 years, but is still entirely unknown. The compound is presumably the first marine natural product to be studied in detail and the first papers to be registered in the literature originate from Brazil.
Three Oleanolic Acid Glycosides from the Seeds of Achyranthes aspera
Authors: Rashmi  , Dayal Rameshwar , Nagatsu Akito
Published: March 2019

From the seeds of Achyranthes aspera three triterpenoid glycosides were isolated and their structures elucidated on the basis of NMR spectroscopic, mass spectrometric and degradative studies as α-L-rhamnopyranosyl-(1→4)-(β-D-glucopyranosyluronic acid)-(1→3)-oleanolic acid, α-L-rhamnopyranosyl-(1→4)-(β-D-glucopyranosyluronic acid)-(1→3)-oleanolic acid-28- O-β-D-glucopyranoside and α-L-rhamnopyranosyl-(1→4)-(β-D-glucopyranosyluronic acid)-(1→3)-oleanolic acid-28- O-β-D-glucopyranosyl-(1→4)-β-D-glucopyranoside.