bluuebunny/crossref_metadata_2025 huggingface dataset:
Virescenols: Sources, Structures and Chemistry
Authors: Marcotullio Maria Carla , Rosati Ornelio , Curini Massimo
Published: March 2019

This review provides the first overview on the isolation and structure elucidation of a class of isopimaric diterpenes: virescenols. An important part of this review deals with the structural modifications of virescenols leading to several different natural product frameworks.
Chemical Composition, Olfactory Evaluation and Antioxidant Effects of the Essential Oil of Satureja Montana L
Authors: Stoilova Ivanka , Bail Stefanie , Buchbauer Gerhard , Krastanov Albert , Stoyanova Albena , Schmidt Erich , Jirovetz Leopold
Published: March 2019

The composition of an essential oil of savory ( Satureja montana L.) from Slovenia was determined by GC/FID and GC-MS; the major components were carvacrol (41.5%), p-cymene (11.0%), thymol (8.6%), γ-terpinene (6.2%) and β-caryophyllene (4.1%). Using olfactory evaluations of the oil, a characteristic odor with strong carvacrol and thymol-notes was found.

Savory oil was capable of antiradical activity with respect to the DPPH, hydroxyl (OH•), and superoxide radicals. The concentrations sufficient for 50% neutralization (IC50) of the respective radicals were 18.7 μg/mL for DPPH and 0.0067 μg/mL for OH•. The neutralization of the superoxide radical at a concentration of 50 μg/mL was by 78.8%. The antiradical activity of savory oil with regard to the DPPH and OH• radicals was substantially greater than that of its major phenolic components, carvacrol and thymol. Savory essential oil demonstrated antioxidant activity in a model system comprised of linoleic acid emulsion, inhibiting at a concentration of 0.01% the conjugated dienes formation by 64.5% and the generation of linoleic acid secondary oxidized products by 73.3%.
Chemical Composition, Olfactory Evaluation and Antioxidant Effects of an Essential Oil of Origanum Vulgare L. from Bosnia
Authors: Stoilova Ivanka , Bail Stefanie , Buchbauer Gerhard , Krastanov Albert , Stoyanova Albena , Schmidt Erich , Jirovetz Leopold
Published: March 2019

The chemical composition of an essential oil of oregano ( Origanum vulgare L.) from Bosnia was analyzed by GC/FID and GC-MS. In total, 33 constituents were identified and carvacrol (66.2%), p-cymene (9.1%), γ-terpinene (7.3%) and β-caryophyllene (4.1%) were found to be the main compounds. In addition, olfactory evaluation data of the sample and correlations with the odor attributes of the single components are presented to explain the complex aroma impression of this essential oil.

The oil possessed antiradical activity with respect to DPPH radicals, exceeding that of its major phenolic component, carvacrol. The oil also revealed scavenging potential with respect to hydroxyl radicals (OH•), which was superior to that towards the DPPH radical; the respective concentrations needed for 50% inhibition (IC50) were 53.8 μg/mL for DPPH and 0.31 μg/mL for OH•. The superoxide scavenging activity of oregano oil was 82.7% at 50 μg/mL. The oil also demonstrated antioxidant activity in a linoleic acid emulsion model system; at 0.05% concentration it inhibited conjugated dienes formation by 69.0% and the generation of secondary oxidized products from linoleic acid by 73.1 %.
Chemical Composition, Olfactory Evaluation and Antioxidant Effects of an Essential Oil of Thymus Vulgaris L. from Germany
Authors: Stoilova Ivanka , Bail Stefanie , Buchbauer Gerhard , Krastanov Albert , Stoyanova Albena , Schmidt Erich , Jirovetz Leopold
Published: March 2019

The composition of an essential oil of thyme from Germany was analyzed by GC/FID and GC-MS. Thirty constituents were identified with thymol (49.6%), p-cymene (16.4%), γ-terpinene (8.0%), linalool (4.6%) and carvacrol (4.0%) as the main compounds. In addition, olfactory evaluations were made of the thyme sample, as well as correlations of odor-impressions of the single constituents with published data. A pleasant aroma, characteristic of thyme oils was determined, with some main and minor constituents as odor-active compounds.

The thyme oil possessed antiradical activity with respect to DPPH, which was greater than the activities of its major individual phenolic components, carvacrol and thymol. The oil also demonstrated a scavenging effect with respect to hydroxyl radicals (OH•), exceeding the effect exercised on the DPPH radical, the respective concentrations resulting in a 50% inhibition (IC50) being 41.4 μg/mL for DPPH and 2.9 μg/mL for OH•. Scavenging of the superoxide radical at a concentration of 50 μg/mL was 76.9%. Thyme essential oil revealed antioxidant activity in a model system comprised of a linoleic acid emulsion where, at a concentration of 0.05%, it caused 59.5% inhibition of conjugated dienes formation and 72.4% inhibition of the generation of secondary oxidized products from linoleic acid.
Chemical Composition, Olfactory Evaluation and Antioxidant Effects of the Essential oil of Origanum Majorana L. from Albania
Authors: Schmidt Erich , Bail Stefanie , Buchbauer Gerhard , Stoilova Ivanka , Krastanov Albert , Stoyanova Albena , Jirovetz Leopold
Published: March 2019

The chemical composition of marjoram essential oil ( Origanum majorana L.) was determined by GC/FID and GC/MS. As major compounds of the oil terpinen-4-ol (21.3%), trans-sabinene hydrate (15.5%), γ-terpinene (14.0%), and α-terpinene (8.9%) were identified. The odour profile and evaluation of marjoram essential oil was established.

Marjoram oil has antiradical activity with regard to DPPH, exceeding that of the phenolic component thymol. The oil exhibited scavenging effect on the hydroxyl radicals (OH•), as well, which substantially exceeded that towards the DPPH radical - the respective concentrations for 50% inhibition of the radicals (IC50) were 0.11μg/mL for OH• and 341.0μg/mL for DPPH.

Marjoram essential oil was capable of antioxidant activity in a linoleic acid emulsion model system, where at concentration of 0.05% it inhibited conjugated dienes formation by 50.00% and the generation of linoleic acid secondary oxidized products by 79.85%.
GC-MS-Analysis, Antimicrobial Activities and Olfactory Evaluation of Essential Davana (Artemisia pallens Wall. ex DC) Oil from India
Authors: Bail Stefanie , Buchbauer Gerhard , Schmidt Erich , Wanner Juergen , Slavchev Alexander , Stoyanova Albena , Denkova Zapriana , Geissler Margit , Jirovetz Leopold
Published: March 2019

An essential oil sample of davana (Artemisia pallens Wall. ex DC.) and a fraction thereof were investigated for their chemical composition using GC and GC-MS. cis-Davanone (45.8%), bicyclogermacrene (9.6%), linalool (2.5%), caryophyllene oxide (2.2%) and phytol (2.1%) were found to be the main constituents of the davana oil sample. The main constituents of the fraction were analyzed as cis-davanone (72.2%), davana ether 2° (5.2%) and ( Z)-ethyl cinnamate (5.2%). Antimicrobial activities of the essential oil, the fraction, some major and reference compounds were evaluated against seven strains of bacteria and one yeast using agar diffusion and agar dilution methods. The davana essential oil showed antimicrobial activities against Staphylococcus aureus, Pseudomonas aeruginosa, Salmonella enterica subsp. enterica and the yeast Candida albicans; the davana fraction was effective against all the tested bacteria and yeast except Pseudomonas aeruginosa and Proteus vulgaris. The oil and the fraction were also olfactorially evaluated.
Chemical Composition and Antifungal Activity of Angelica sinensis Essential Oil Against three Colletotrichum Species
Authors: Tabanca Nurhayat , Wedge David E. , Wang Xiaoning , Demirci Betul , Baser Kemal Husnu Can , Zhou Ligang , Cutler Stephen J.
Published: March 2019

Chemical fungicides are an important component in disease management for most crops. As part of a program to discover natural product-based fungicides, several sensitive assay systems have been developed for the evaluation of naturally occurring antifungal agents. In this study, we focused on the discovery and evaluation of new natural product-based fungicides from Angelica sinensis (Dong Quai) for use in control of strawberry anthracnose caused by Colletotrichum species. A. sinensis oil was evaluated for antifungal activity against three Colletotrichum species using direct-bioautography assay and a strawberry detached leaf assay using C. fragariae. Chemical composition and fingerprinting were conducted by gas chromatography and gas chromatography-mass spectrometry. Major components were identified as ( Z) -ligustilide (43.1%), ( E)-3-butylidene phthalide (14.5%), ( Z)-β-ocimene (12.9%), and apiole (11.2%).
Investigation of Anticancer and Antiviral Properties of Selected Aroma Samples
Authors: Ryabchenko Boris , Tulupova Elena , Schmidt Erich , Wlcek Katrin , Buchbauer Gerhard , Jirovetz Leopold
Published: March 2019

Anti-tumor and antiviral activities of various aroma samples, including cinnamic acid, β-caryophyllene, caryophyllene oxide, nerolidol (synthetic and natural samples), trans, trans-farnesol, farnesol (isomeric mixture), longifolene, geranic acid and a farnesol-rich ylang-fraction were investigated using HeLa and Jurkat cell lines.

Using a CytoTox-96®-Assay we observed strong anti-tumor effects of natural- and synthetic nerolidol-samples at concentrations less than 5 μM. Furthermore, synthetic nerolidol reduced the number of HeLa and Jurkat cells to 50% (CC50) at concentrations which were more than ten times lower compared with the effective doses required to achieve 50% cytotoxicity (ED50). Antiviral studies were performed to investigate inhibitory effects of the compounds on mouse polyomavirus propagation in 3T6 cells. Remarkable inhibition of viral activity was demonstrated by synthetic nerolidol at CC50 3.2 ± 1.5 μM and natural nerolidol at CC50 1.2 ± 0.4 μM All other compounds, however, did not show any inhibition against this virus.
Chemical and Biological Investigations of Essential Oils from Stem Barks of Enantia Chlorantha Oliv. and Polyalthia Suaveolens Engler. & Diels. from Cameroon
Authors: Nyegue Maximilienne , Amvam-Zollo Paul-Henri , Etoa François-Xavier , Agnaniet Huguette , Menut Chantal
Published: March 2019

The chemical composition and in vitro bioactivities of essential oils obtained by hydrodistillation of barks of Enantia chlorantha and Polyalthia suaveolens, two Annonaceae from Cameroon were investigated. Chemical analyses by GC and GC-MS showed that for both plants sesquiterpenes are predominant, the main constituents being 1,5-epoxysalvial-4(14)-ene (12.8%), caryophyllene oxide (13.4%), humulene epoxide II (8.1%) and spathulenol (7.0%), for E. chlorantha; β-caryophyllene (16.0%), germacrene D (8.5%), e pi-α-cadinol (8.3%), caryophyllene oxide (7.3%), salvia-4(14)-en-1-one (7.3%) and 5-cadinene (6.0%) for P. suaveolens. Evaluation of the antiradical scavenging activity by the 1,1-diphenyl-2-picryhydrazyl (DPPH) method indicated that the P. suaveolens essential oil was more active (SC50= 0.71 g/L) than that from E. chlorantha (8.0 g/L). In both cases, the essential oils were less efficient than BHT, taken as a reference (8.8 10-3g/L). In vitro microbiological screening revealed that E. chlorantha essential oil presents a significant activity against the three bacterial strains, Escherichia coli, Pseudomonas aeruginosa and Staphylococcus aureus (with a maximum activity > 90% at 2 mg/mL) and six fungal strains, Candida albicans, Microsporum canis, Trychophyton rubrum, Fusarium moniliforme, Aspergillus flavus and Aspergillus niger (with a maximum activity > 75% at 2 mg/mL). The volatile extract of P. suaveolens is globally less efficient, as it does not inhibit the growth of either S. aureus or A. flavus.
Physiological and Behavioral Effects of 1,8-Cineol and (±)-Linalool: A Comparison of Inhalation and Massage Aromatherapy
Authors: Heuberger Eva , Ilmberger Josef , Hartter Engelbert , Buchbauer Gerhard
Published: March 2019

The effects of fragrances on human arousal are not well understood. The aim of the present investigation was to determine the influence of two monoterpenes, 1,8-cineol and (±)-linalool, on human sustained attention, physiological arousal and well-being. The substances, as well as appropriate placebos, were administered either by inhalation or by skin application to a total of 130 healthy subjects. We found that when the fragrances were applied to the skin 1,8-cineol improved speed of attentional performance in comparison to (±)-linalool, but not in comparison to peanut oil, which served as a placebo. Under the same conditions, 1,8-cineol increased respiration rate in comparison to both (±)-linalool and placebo. In the inhalation condition, neither attentional performance nor physiological arousal were affected by the fragrances, but both odorants influenced well-being, i.e., 1,8-cineol decreased activation and (±)-linalool increased it. In contrast, no such effects were observed in the skin application condition. Our results demonstrate that fragrances affect cognitive performance, physiological arousal and well-being as a function of the mode of administration.
Synergistic and Antagonistic Interactions of Essential Oils on the Biological Activities of the Solvent Extracts from Three Salvia species
Authors: Kamatou Guy P. P. , Van Zyl Robyn L. , Davids Hajierah , Van Vuuren Sandy F. , Viljoen Alvaro M.
Published: March 2019

The solvent extracts of aromatic plants contain both volatile (e.g. essential oils) and non-volatile compounds. The biological activities (antibacterial, anti-oxidant, antiplasmodial and anticancer) of the solvent extracts of three South African Salvia species ( Salvia africana-caerulea, S. africana-lutea and S. lanceolata) were evaluated in the presence and absence of the essential oils. The solvent extract of S. africana-caerulea free of essential oil exhibited the best activity against Gram-positive bacteria (MIC value: 0.4 mg/mL), while the solvent extract containing essential oil of S. lanceolata was the most active against Gram-negative bacteria (MIC value: 2.0 mg/mL). No significant difference was obtained in the antiplasmodial activity of the solvent extract with or without the essential oils of S. africana-caerulea and S. lanceolata, while the activity of the solvent extract without essential oil was significantly higher than that of the solvent extract containing the essential oil in S. africana-lutea (p < 0.05). The toxicity profile of all three species was significantly higher (p < 0.05) with the solvent extracts containing essential oils than when assessed in the absence of the essential oil.
Essential Oil Composition of Eryngium Campestre L. Growing in Different Soil Types. A Preliminary Study
Authors: Palá-Paúl Jesús , Usano-Alemany Jaime , Soria A. Cristina , Pérez-Alonso M. José , Brophy Joseph J.
Published: March 2019

The essential oil composition of the aerial parts of four populations of Eryngium campestre has been analyzed by GC and GC/MS. Samples growing in different types of soil were gathered at the same phenological state. A total of 84 compounds have been identified from the different samples under analysis. Qualitative and quantitative differences were found between inflorescences (I) and stems and leaves (SL) of the different populations. The main constituents of the inflorescences were identified as germacrene D (30.3-40.3%), β-curcumene (0.7-22.2%), myrcene (3.0-21.7%) and ( E)-β-farnesene (0.1-19.0%). The type of soil seemed to exert an influence on the chemical composition of the oils of this species. Whereas high concentrations of myrcene were found in the populations growing in acid soil, its concentration was significantly lower in the alkaline populations. β-Curcumene concentration was higher in the populations growing in alkaline soil and was practically absent from the acid soil population. Regarding the stems and leaves, only germacrene D (31.1-42.4%) and myrcene (0.5-23.15) were considered as main constituents, their composition not being affected by the type of soil. However, terpenoid distribution was clearly influenced by the soil, with the population growing in acid soil containing a greater amount of monoterpenes than that of the population growing in alkaline soil. A more exhaustive study needs to be carried out in order to confirm if the biosynthesis of these compounds could be influenced by the availability of Ca2+ in the soil.
Variability of the Volatile Oil Composition in a Population of Silaum Silaus from Eastern Austria
Authors: Chizzola Remigius
Published: March 2019

The volatiles present in the above ground parts of Silaum silaus (L.) Schinz et Thell. (Apiaceae), pepper saxifrage, were analysed by GC/MS and GC. The fractions investigated were the distilled oil, n-hexane extracts and solid phase microextracts (SPME) of the different plant parts. Myristicin was the main volatile compound in the fruits, followed by ( E)-β-ocimene. The leaves and stems contained α-pinene, myristicin, ( Z)-β-ocimene and ( E)-β-ocimene as major compounds in the essential oil. Additionally, in a root headspace sample 2,4,5-trimethylbenzaldehyde was the main compound.
Essential Oil Polymorphism of Hungarian Common Thyme (Thymus Glabrescens Willd.) Populations
Authors: Pluhár Zsuzsanna , Sárosi Szilvia , Novák Ildikó , Kutta Gabriella
Published: March 2019

The volatile oil compositions of Thymus glabrescens Willd. from eight different localities of Hungary were analyzed by GC/MS. Significant essential oil polymorphism was found: eight new chemovarieties may have been determined, representing a way of adaptation to the different habitat conditions. The main volatile compounds of chemotype 1 (Csesznek) were thymol (34.2%), γ-terpinene (26.2%) and p-cymene (16.4%). In the case of chemotype 2 (Várpalota), germacrene D (55.4%) and β-caryophyllene (14.8%) were identified as chief constituents. Chemotype 3 (Szentbékkálla) contained thymol (32.9%), β-caryophyllene (16.5%) and germacrene D (17.6%), while chemotype 4 (Várvölgy) accumulated α-cubebene (50.9%) and β-caryophyllene (22.9%) as the main volatiles. The oil of chemotype 5 (Várgesztes) can be characterized by geraniol (49.0%) and germacrene D (13.6%), while that of chemotype 6 (Tardosbánya) consisted of p-cymene (45.0%), geraniol (13.6%) and linalyl acetate (9.9%). In the oil of chemotype 7 (Salgó Hill), thymol (14.4%), germacrone (12.1%) and geraniol (10.8%) were found in higher percentages, while chemotype 8 (Pásztó) produced thymol (29.3%) and germacrene D (14.2%) as its main essential oil compounds. The existence of thymol chemotypes in the case of T. glabrescens is new for the literature.
Diversity of Essential Oil Glands of Spanish Sage (Salvia Lavandulifolia Vahl, Lamiaceae)
Authors: Schmiderer Corinna , Grassi Paolo , Novak Johannes , Franz Chlodwig
Published: March 2019

Salvia lavandulifolia (Spanish sage, Lamiaceae) is widely cultivated in the Mediterranean region and used for the flavor and food industry, perfumery and medicinal purposes. The essential oil, which is responsible for the specific flavor, is produced and stored in specialized epidermal oil glands. In S. lavandulifolia peltate essential oil glands occur on all aerial parts of the plant. The content of single oil glands from different positions on the plant (leaf, calyx, corolla and anther) were directly sampled using a solid-phase micro-extraction (SPME) fiber and analyzed by GC/FID and GC/MS in order to study the variability of the essential oil composition. It was found that the composition of terpenoids is quite variable within a plant. The leaves and calyces are characterized by the main compounds, 1,8-cineole, camphor and β-pinene, and by the sesquiterpenes α-humulene and β-caryophyllene. The corolla shows the highest proportion of borneol, but a low concentration of camphor. In the essential oil of the anthers the percentages of limonene, β-pinene and the diterpene manool are by far higher than in all other plant parts, whereas the proportions of camphor and the sesquiterpenes are considerably lower.
Transient Induction of Antimicrobial 3-Deoxyflavonoids does not Affect Pharmacological Compounds in Hawthorn
Authors: Schlangen Karin , Halbwirth Heidi , Peterek Silke , Gosch Christian , Ringl Alexandra , Fischer Thilo C. , Treutter Dieter , Forkmann Gert , Kopp Brigitte , Stich Karl
Published: March 2019

Hawthorn ( Crataegus sp.) is a traditional medicinal plant, which shows a broad spectrum of health-related effects. Drug preparation is based on material collected from wild growing plants, which usually show variability in their secondary metabolite composition and concentration. Plantations of selected hawthorn genotypes could form the basis of a consistent homogeneous source of top-quality hawthorn drugs. However, as hawthorn is a member of the Rosaceae family, such plantations would be threatened by the bacterial disease fire blight, which currently causes dramatic economic losses in apple and pear orchards. We show that prohexadione-Ca induces the formation in Crataegus monogyna leaves of the rare class of 3-deoxyflavonoids, which are responsible for better fire blight resistance and that the quality and quantity of the health related ingredients are not negatively influenced by prohexadione-Ca treatment.
Trafficking and Sequestration of Anthocyanins
Authors: Grotewold Erich , Davies Kevin
Published: March 2019

Flavonoids are synthesized on the cytoplasmic surface of the endoplasmic reticulum (ER). As is the case for several other phytochemicals, anthocyanins and other products of the pathway often accumulate in the large central vacuole. This review summarizes recent findings on the possible mechanisms by which flavonoids traffic between the ER and the vacuole, and discusses the frequent localization of anthocyanins in sub-vacuolar structures with variable characteristics.
Anthocyanins Reduce Fungal Growth in Fruits
Authors: Schaefer H. Martin , Rentzsch Michael , Breuer Michael
Published: March 2019

As the most visible role of anthocyanins is to impart colors, the adaptive significance of anthocyanins in plant reproductive organs is invariably attributed to the attraction of seed dispersers and pollinators. However, few studies suggested that anthocyanins in vegetative tissue might also function in plant defence, although the evidence for such a function is not particularly strong. Here, we investigated whether anthocyanins contribute to fruit defence against fruit-rot fungi. We found that the risk of fruit-rot in grape varieties infected with Botrytis cinerea decreased with increasing anthocyanin contents. Moreover, anthocyanin contents directly inhibited growth rates of nine fruit-rot fungi on agar plates. Anthocyanins reduced fungal growth by 50% in the concentrations that typically characterise unripe blackberries and by 95% in the concentrations that typify ripe blackberries. We conclude that anthocyanins in fruits not only function to attract animal vectors, but that they also contribute to fruit defence. The antifungal activity of anthocyanins might more widely explain their occurrence in various plant organs such as vegetative tissue and roots.
Phenolic Compounds Produced by Secretory Structures in Plants: A Brief Review
Authors: Marilia De M. Castro , Demarco Diego
Published: March 2019

The purpose of this brief review has been to provide more recent data regarding the production of phenolic compounds by secretory structures. Although morphology and histochemistry of glands are well documented, meagre information concerning phenolics is available in the surveyed literature. Two major groups of glands are found regarding phenolic compounds synthesis: 1. secretory cells producing mainly phenolics, 2. secretory cells producing phenolics coupled with other compounds. In the former group, phenolic compounds remain in mature organs, and prevail in the material produced by epidermis, hypodermis, idioblasts, and sheath encircling vascular bundles and ducts. The latter group is constituted of trichomes, cavities, ducts, laticifers, colleters, nuptial nectaries, osmophores and stigma system, which synthesize complex mixtures of terpenes, phenolic compounds, polysaccharides and other compounds. In vegetative organs, the secretion of these glands might provide chemical defence against damage by UV radiation, against pathogen activities, and play a role in the herbivory deterrence. Additional functions ascribed to phenolics produced by floral glands are associated with pollination, pollen germination and pollen-tube elongation.
Surface Flavonoids in Catalpa Ovata, Greyia Sutherlandii and Paulownia Tomentosa
Authors: Wollenweber Eckhard , Wehde Rüdiger , Christ Matthias , Dörr Marion
Published: March 2019

Exudate flavonoids have been found on the green fruits of Catalpa ovata (Bignoniaceae) and Paulownia tomentosa (Scrophulariaceae) and on the leaf surfaces of Greyia sutherlandii (Melianthaceae) and Paulownia tomentosa, respectively. The flavonoid aglycones are mostly flavone and flavonol methyl ethers, including some rare natural products. Several flavanones and 2 dihydrochalcones have also been detected, the flavanones produced by Paulownia being geranylated products. The occurrence of exudate flavonoids on fruit tissue has been rarely noticed in the past.
Occurrence and Distribution of the Flavone Tricetin and its Methyl Derivatives as Free Aglycones
Authors: Wollenweber Eckhard , Dörr Marion
Published: March 2019

This paper presents a review of the occurrence of tricetin and its methyl ethers, with respect to their occurrence in the free state. In addition to literature data, our tabulated survey also includes a dozen unpublished results. The review indicates that 5,7,3′,4′,5′-pentahydroxyflavone and its methyl derivatives are more widespread than was known so far. Their presence as aglycones has been proved in a good number of plant species belonging to unrelated families.
Variation in Flavonoids in Leaves, Stems and Flowers of White Clover Cultivars
Authors: Carlsen Sandra C.K. , Mortensen Anne G. , Oleszek Wieslaw , Piacente Sonia , Stochmal Anna , Fomsgaard Inge S.
Published: March 2019

In the present study, the major flavonoids of white clover ( Trifolium repens L.) cv. Sonja were extracted, isolated and identified. The major flavonoids in leaves and stems were the four flavonol glycosides: kaempferol-3- O-{Xyl(1→2)-Gal} (kaempferol-Xyl-Gal), kaempferol-3- O-{Rha(1→6)-[Xyl(1→2)]-Gal} (kaempferol-Rha-Xyl-Gal), quercetin-3- O-{Xyl(1→2)-Gal} (quercetin-Xyl-Gal), and quercetin-3- O-{Rha(1→6)-[Xyl(1→2)]-Gal} (quercetin-Rha-Xyl-Gal). Quercetin-Rha-Xyl-Gal has never been reported before and kaempferol-Rha-Xyl-Gal has not previously been identified in clover aerial parts. Concentrations of those compounds, together with aglyconic flavonoids previously described in white clover, as well as their glycosides, were quantified in leaves/stems and flowers of four white clover cvs Rabani, Klondike, Ramona and Aran using tandem mass spectrometry. There were significant differences in flavonoid concentrations in the two plant parts, with the highest concentrations of most aglycones in flowers and the highest concentrations of most glycosides in leaves/stems. This distribution of compounds may indicate different ways of storage and/or different mechanisms of action of the compounds. The cultivars were selected for genetic diversity, which resulted in distinctly different amounts of flavonoids in the plants. Concentrations of 17 of 24 compounds varied significantly – for some compounds up to a factor of 10 – among cultivars. Total flavonoid concentrations in flowers did not vary greatly among cultivars, at 28.9–35.8 mmol/g dry material (DM). In contrast, in leaves/stems, the cvs Rabani and Klondike had lower concentrations of most flavonoids (total concentrations 10.0 and 12.7 mmol/gDM, respectively) compared to cvs Aran and Ramona (32.3 and 22.1 mmol/gDM, respectively). There is a potential for breeding/selection of cultivars with targeted concentrations of particular flavonoids.
Two New Kaempferol Glycosides from Matthiola Longipetala (subsp. livida) (Delile) Maire and Carcinogenic Evaluation of its Extract
Authors: Marzouk Mona M. , Kawashty Salwa A. , Ibrahium Lamyaa F. , Saleh Nabiel A. M. , Al-Nowaihi Abdel-Ssalam M.
Published: March 2019

Two new kaempferol glycosides, kaempferol 3- O-(2″-α-L-rhamnopyranosyl)-β-L-arabinopyranoside-7- O-α-L-rhamnopyranoside and kaempferol 3- O-(2″-α-L-rhamnopyranosyl)-β-L-arabinopyranoside-7- O-α-L-rhamnopyranoside-4′- O-β-D-glucopyranoside were isolated along with four known flavonols from Matthiola longipetala (subsp. livida) (Delile) Maire growing in Egypt. Their structures were established on the basis of detailed chemical and spectral analysis. The cytotoxic activity of the alcoholic extract against Cervix (HELA) and Colon (HCT116) human cell lines showed IC50 values of 22.1 and 53.7 μg/mL, respectively. No activity was found against liver (HEPG2) carcinoma cells.
Newer Constituents of Derris Indica Stem
Authors: Shankar Thangaraj , Muthusubramanian Shanmugam , Gandhidasan Rathinasamy
Published: March 2019

Two new compounds, 5,7-dihydroxy-6-methyl-4′-methoxyisoflavone (6-methylbiochanin A) (1) and cis-3,5-diphenylpiperidine-2,6-dione (2) were isolated from the young stems of Derris indica along with desmethoxykanugin (3), 3′, 5′-dimethoxy-(2″, 3″: 7, 8)furanoflavone (4) and 7,4′-dimethyldaidzein (5). The structures of these compounds were determined by means of chemical and spectral studies.
Structural Characterization of Genuine (-)-Pipermethystine, (-)-Epoxypipermethystine, (+)-Dihydromethysticin and Yangonin from the Kava Plant (Piper methysticum)
Authors: Naumov Panče , Dragull Klaus , Yoshioka Masahiro , Tang Chung-Shih , Ng Seik Weng
Published: March 2019

Two alkaloids, (-)-pipermethystine and (-)-epoxypipermethystine, and two lactones, (+)-dihydromethysticin and yangonin, were isolated from the kava plant ( Piper methysticum) and crystallographically authenticated.
Oxidative Decarboxylation of Triterpene C-28 Acids of Lupane Series
Authors: Komissarova Nataliya G. , Belenkova Nataliya G. , Shitikova Olga V. , Spirikhin Leonid V. , Yunusov Marat S.
Published: March 2019

The oxidative decarboxylation of betulonic, 3,20-dioxo-29- nor-lupan-28-oic, dihydrobetulonic acids with Pb(OAc)4 in the presence of Py, Cu(OAc)2, CF3COOH or with PhI(OAc)2 – I2 leads to 28- nor-lup-16(17)-enes and 28- nor-lup-17(22)-enes, and 17α-acetoxy derivatives. The proportion of regioisomeric olefines is related to a substituent at C-19; the yields of olefines and of acetoxy derivatives depends on reaction conditions and structures of the starting acids. The structures of products were determined by spectroscopic methods.
Proapoptotic and Anticarcinogenic Activities of Leviusculoside G from the Starfish Henricia leviuscula and Probable Molecular Mechanism
Authors: Fedorov Sergey N. , Shubina Larisa K. , Kicha Alla A. , Ivanchina Natalia V. , Kwak Jong Y. , Jin Jun O. , Bode Ann M. , Dong Zigang , Stonik Valentin A.
Published: March 2019

Proapoptotic and anticarcinogenic properties of leviusculoside G (LSG) isolated from the starfish Henricia leviuscula and a probable mechanism of these effects were investigated in human leukemia HL-60, THP-1, and mouse skin JB6 Cl41 cells, using a variety of assessments, including a cell viability (MTS) assay, flow cytometry, anchorage-independent soft agar assay, luciferase assay, and western-blotting. Application of LSG at nontoxic doses induced apoptosis in cancer cells and decreased cell transformation. This compound exerted its actions, at least in part, through the induction of p53-dependent apoptosis and inhibition of AP-1, NF-κB, and ERKs activities.
New Angucyclinones from the Marine Mollusk Associated Actinomycete Saccharothrix espanaensis An 113
Authors: Kalinovskaya Nataliya I. , Kalinovsky Anatoly I. , Romanenko Lyudmila A. , Pushilin Mikhail A. , Dmitrenok Pavel S. , Kuznetsova Tatyana A.
Published: March 2019

Three new angucyclinones, saccharothrixins A (6), B (7) and C (8), together with five known analogues, X-14881 A (1), X-14881 E (2), ochromycinone (3), X-14881 C (4) and X-14881 B (5), were isolated from the actinomycete Saccharothrix espanaensis An 113 associated with the marine mollusk Anadara broughtoni. The structures of the new compounds were elucidated by spectroscopic methods including one- and two-dimensional NMR and by comparison of the NMR data with those of the structurally related known angucyclinone X-14881 A (1).
2,4-Dihydroxypentanoic Acids: New Non-sugar Components of Bacterial Polysaccharides
Authors: Shashkov Alexander S. , Kocharova Nina A. , Toukach Filip V. , Kachala Vadim V. , Knirel Yuriy A.
Published: March 2019

New components of bacterial polysaccharides, (2 S,4 R)- and (2 R,4 R)-2,4-dihydroxypentanoic acids, were identified using two-dimensional 1H and 13C NMR spectroscopy in the O-antigens of Providencia alcalifaciens O8 and O31. The acids were ether-linked via their 2-HO-group to a residue of either N-acetylglucosamine or mannose at position 4. The absolute configurations of the acids were determined by NOE spectroscopy, combined with molecular modeling.
Structural Analysis of Antibiotic INA 9301 from Amycolatopsis Orientalis
Authors: Shashkov Alexander S. , Tsvetkov Dmitry E. , Grachev Alexey A. , Lapchinskaia Olda A. , Lavrova-Balashova Maia F. , Ponomarenko Valerii I. , Katrukha Genrikh S. , Nifantiev Nikolay E.
Published: March 2019

The dalbaheptide antibiotic INA 9301 was isolated from a culture of Amycolatopsis orientalis. By using a combination of mass spectrometry and NMR spectroscopy, INA 9301 was assessed as N,N-dimethylvancomycin. Detailed 13C NMR characteristics of INA9301 in D2O and DMSO- d 6 are presented, together with 2D 1H-1H ROESY and 1H-13C gHMBC data, which confirmed the configurations of the asymmetric centers and spatial conformational shape of the molecule in aqueous solution.
Inhibition of Mushroom Tyrosinase and Melanogenesis B16 Mouse Melanoma Cells by Components Isolated from Curcuma longa
Authors: Kim Jeong Ah , Son Jong Keun , Chang Hyun Wook , Jahng Yurngdong , Kim Youngsoo , Na MinKyun , Lee Seung Ho
Published: March 2019

The methanol extract of the rhizomes of Curcuma longa was found to inhibit tyrosinase activity. After partition, various column chromatographic and preparative HPLC procedures were used for bioassay guided isolation from the active ethyl acetate-soluble fraction. Various spectroscopic (1D-, 2D-NMR) and mass spectrometric techniques, and Mosher's esterification were applied to elucidate the structures of the isolated compounds. The isolates were tested using an in vitro mushroom tyrosinase assay. Inhibition of melanin formation by the active compounds was further evaluated using B16 mouse melanoma cells. Eleven compounds (1 – 11) were isolated from the rhizomes of C. longa by bioassay guided fractionation. The configuration at the C-4 position of 4-hydroxy-1,3(15),10-bisabolatrien-9-one (11) was confirmed by Mosher's method. Of the isolates, curcuminoids 5 - 7 showed potent inhibitory activity in the tyrosinase assay. Melanin formation of the active compounds in the B16 mouse melanoma cells corresponded with the tyrosinase inhibitory activity. The findings support the view that either curcuminoids or the extract of C. longa rhizomes containing them may be useful for the treatment of hyperpigmentation.
Reaction of Furanoeremophilans with Pyridoxal
Authors: Torihata Atsushi , Kuroda Chiaki
Published: March 2019

Furanoeremophilan-10β-ol, a major component of Ligularia cymbulifera growing in northwestern Yunnan Province of China, reacted with pyridoxal or its 5′-phosphate at room temperature in aqueous solution to afford condensation products. It is plausible that the reaction also occurs in nature.
A Bioactive Diterpene from Smallanthus sonchifolius
Authors: Ragasa Consolacion Y. , Alimboyoguen Agnes B. , Urban Sylvia , Raga Dennis D.
Published: March 2019

The dichloromethane extract of the air-dried leaves and freeze-dried tubers of Smallanthus sonchifolius afforded ent-kaurenoic acid (1). The structure of 1 was elucidated by extensive 1D and 2D NMR spectroscopy and was found to exhibit significant analgesic and anti-inflammatory activities. Ent-kaurenoic acid (1), dissolved in dimethylsulfoxide, also displayed potential anti-diabetes and anti-toxicity activity. In addition, 1 showed low antimicrobial activities against E. coli, P. aeruginosa, S. aureus, C. albicans and T. mentagrophytes, but was found to be inactive against B. subtilis and A. niger.
Comparative Photobleaching Behavior of Hypocrellin A and Elsinochrome C
Authors: Zhao Qian , Zhang Hong-Yu
Published: March 2019

Hypocrellin A (HA) and elsinochrome C (EC) are naturally-occurring perylenequinonoid photosensitizers. To evaluate their potential as photoactive medicines and/or pesticides, the photobleaching behaviors of both compounds were studied in two organic systems (ethanol and DMSO). It was found that, although HA and EC possess comparable photosensitizing activities, EC is more stable to photobleaching than HA. Both pigments exhibited higher photo-stability in ethanol than in DMSO. Therefore, it seems that EC has more developmental potential than HA and its photobleaching behavior can be modified by changes in media polarity.
Variation of Bioactive Secondary Metabolites in Hypericum triquetrifolium Turra from Wild Populations of Turkey
Authors: Çamaş Necdet , Radušienė Jolita , Ayan Ali Kemal , Çırak Cüneyt , Janulis Valdimaras , Ivanauskas Liudas
Published: March 2019

The present study was conducted to determine the variation in the content of hyperforin, hypericin and pseudohypericin in Hypericum triquetrifolium Turra growing wild in four locations of Turkey. The aerial parts, representing a total of 30 individuals, were collected at full flowering and dissected into floral, leaf and stem tissues. After drying at room temperature, the plant materials were assayed for their chemical contents by HPLC. The populations varied significantly in chemical contents. Hyperforin content ranged from 0.05 to 0.56 mg/g, hypericin from 0.74–1.98 mg/g, and pseudohypericin from 0.72–2.26 mg/g, dry weight. Among the different plant parts, the flowers were found to be the principle organ for hyperforin accumulation, while hypericin and pseudohypericin were accumulated mainly in leaves. Such kinds of data could be useful for optimizing the processing methodology of wild-harvested plant material and phytochemical evaluation of H. triquetrifolium.
Anti-inflammatory Activity of Piper Magnibaccum (Piperaceae)
Authors: Emrizal  , Ahmad Farediah , Sirat Hasnah M. , Jamaludin Fadzureena , Mustapha Nik Musa'adah , Ali Rasadah M. , Arbain Dayar
Published: March 2019

Anti-inflammatory activity of a crude extract of Piper magnibaccum (Piperaceae) and of compounds isolated from it was established using the TPA-induced mouse ear edema model and an in vitro quantitative lipoxygenase inhibition assay. Five compounds were isolated from P. magnibaccum [β-sitosterol, N-isobutyl-(2 E,4 E)-tetradecadienamide, linoleic acid, 13-(4′, 5′-dimethoxytridecanoyl)piperidine, and piperine]. The light petroleum extract of the plant exhibited significant anti-inflammatory activity in both models. N-isobutyl-(2 E,4 E)-tetradecadienamide showed significant activity, with an IE % value of 70.2 + 5.4 in the TPA-induced mouse ear edema model and 87.2 + 0.11 in the in vitro quantitative lipoxygenase inhibition assay.
Comparative Analysis of the Essential Oils from two Asteraceous Plants Found in Nigeria, Acanthospermum Hispidum and Tithonia Diversifolia
Authors: Gbolade Adebayo A. , Biondi Daniela M. , Ruberto Giuseppe
Published: March 2019

The essential oils from two members of the Asteraceae ( Acanthospermum hispidum DC. aerial parts, and leaves of Tithonia diversifolia (Hemsley) A. Gray), growing wild in Osun State, Nigeria, have been characterised by combined gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS) analyses. Twenty-nine components have been fully identified and grouped into monoterpene hydrocarbons (22.2%), oxygenated monoterpenes (4.6%), sesquiterpenes hydrocarbons (58.2%) and oxygenated sesquiterpenes (10.8%) in A. hispidum. The main constituents of the oil were β-caryophyllene (28.0%), α-pinene (15.9%) and bicyclogermacrene (11.0%) among the hydrocarbon compounds, and bisabolol (8.9%) and carvacrol methyl ether (4.1%) among the oxygenated components. Tithonia diversifolia essential oil comprised seventeen components and was characterised by a predominant content of monoterpene hydrocarbons (87.9%), cis-β-ocimene (43.7%), α-pinene (28.6%) and limonene (12.0%) being the main compounds. Sesquiterpenes represented ca. 10% oil, as sum of hydrocarbons and oxygenated components. A new chemotype is established for T. diversifolia, while the Nigerian A. hispidum is being reported for the first time as a new source of essential oil with some distinction in composition from those of other sources.
New Drimane Sesquiterpenoids from Tidestromia Oblongifolia
Authors: Chaudhary Sandeep , Thomas Vladimir , Todaro Louis , LeGendre Onica , Pecic Stevan , Harding Wayne W.
Published: March 2019

From an acetone extract of the aerial parts of Tidestromia oblongifolia (Amaranthaceae), a new drimane sesquiterpenoid bearing an 11,12,13-trihydroxydrimene skeleton (1), as well as the 11,12 acetonide of 1 were isolated. Three known stigmastane triterpenoids were also isolated. Structures were elucidated with the aid of 1D and 2D NMR spectroscopic techniques. The absolute configuration of 1 was confirmed by single-crystal x-ray crystallography. This is the first report on phytochemical constituents from any plant of the genus Tidestromia and is the first report of the occurrence of drimanes in the Amaranthaceae.
Triterpenoidal Saponins and Prosapogenins from Albizia Lebbeck (Leguminosae)
Authors: Scott Janelle P. , Tinto Winston F. , Reynolds William F.
Published: March 2019

Four new echinocystic acid glycosides (1–4) were isolated from the dried seeds of Albizia lebbeck. The alkaline hydrolysate of the saponin fraction yielded two new prosapogenins (5–6). Their structures were determined by extensive NMR and spectroscopic analysis.
Synthetic and Computational Studies on the ABC Trioxadispiroketal Subunit of the Marine Biotoxin Azaspiracid-1
Authors: Li Jialiang , Li Xiaohua , Mootoo David R.
Published: March 2019

The trioxadispiroketal residue in the marine biotoxin azaspiracid-1, which exists in a configuration capable of exhibiting a double anomeric effect, is believed to be the thermodynamically most stable bis-spiroketal diastereomer. In order to get insight into how structural factors affect this equilibrium, a simplified ABC trioxadispiroketal analog of azaspiracid-1 was synthesized and subjected to equilbration and computational studies. Compound 7, which represents a double anomeric effect was obtained as the major isomer, together with diastereomers 14 and 15, in a respective ratio of 62:22:16. DFT calculations for 7, 14 and 15 qualitatively matched this observation. These results suggest that while a double anomeric effect may play a major role in the stability of the trioxadispiroketal configuration in the more complex natural product, the substitution pattern of the C ring is also a contributing factor.
Secondary Metabolites from Clerodendrum Chinense
Authors: Layne Tanya H. , Reynolds William F. , McLean Stewart , Tinto Winston F.
Published: March 2019

Chemical studies carried out on Clerodendrum chinense yielded three new compounds including the steroid (22E, 24S)-stigmasta-4, 22, 25-trien-3-one (1), the flavone glycoside 7, 8, 4′-trihydroxyflavone-6-O-β-D-glucuronopyranoside (2) and the epimeric neo-clerodane 14, 15-dihydro-15ξ-hydroxyclerodendrin A (3). Two acetylated derivatives of compound 3-, 2α-acetoxy-14, 15-dihydro-15ξ-hydroxyclerodendrin A (4) and 2α-acetoxy-14, 15-dihydro-15ξ-methoxyclerodendrin A (5) were also prepared, which have not been reported previously. The structure of each compound was elucidated by spectroscopic means.
Dittrichia Viscosa L. Greuter: Phytochemistry and Biological Activity
Authors: Barrero Alejandro F. , Herrador M. Mar , Arteaga Pilar , Catalán Julieta V.
Published: March 2019

Dittrichia viscosa is a plant widely distributed in the Mediterranean region. This species and its components present a broad range of biological activities (for example, anti-inflammatory, antifungal, antiulcer, antiviral, antiparasitic), which are reviewed. Extracts of the species are particularly rich in terpenoids, in particular eudesmane acids, notably ilicic acid (45) and α-costic acid (44). Flavonoids are also abundant, especially during flowering.
Two New Sesquiterpene Lactone-esters from Achillea vermicularis
Authors: Farooq Umar , Khan Afsar , Ahmad Viqar Uddin , Azhar-ul-Haq  , Farooq Robina , Pervez Arshid , Jassbi Amir Reza
Published: March 2019

Phytochemical investigation of the whole plant of Achillea vermicularis led to the isolation of two new sesquiterpene lactone-esters, vermicularon A and B (1–2). The structures of these compounds were determined primarily with the help of one- and two-dimensional (1D and 2D) NMR techniques, including 1H NMR, 13C NMR, HMQC, and HMBC experiments.
A Cytotoxic Diterpenoid from Croton Membranaceus, the Major Constituent of Anticancer Herbal Formulations Used in Ghana
Authors: Bayor Marcel T. , Ayim John S. K. , Marston Gemma , Phillips Roger M. , Shnyder Steven D. , Wheelhouse Richard T. , Wright Colin W.
Published: March 2019

Croton membranaceus is used by herbalists and traditional healers in Ghana for the management of various cancers, especially prostate cancers. A methanolic extract of the roots showed cytotoxic activities against two cancer cell lines, and bioassay-guided fractionation of this extract revealed that the cytotoxic activity resided mostly in the ethyl acetate fraction. Six compounds were isolated from this fraction, including a new furano-clerodane diterpenoid (1), for which the trivial name crotomembranafuran is suggested. This compound exhibited an IC50 value of 4.1 μg/mL (10.6 μM) against human prostate (PC-3) cells, providing some support for the traditional use of C. membranaceus in the treatment of cancers.
Two Novel Acylated Flavonol Glycosides from Platanus Orientalis L. Leaves
Authors: El-Alfy Taha S. , El-Gohary Hamida M.A. , Sokkar Nadia M. , Al-Mahdy Dalia A.
Published: March 2019

Two novel acylated flavonol glycosides were isolated from the n-butanol fraction of the ethanolic extract of Platanus orientalis L. leaves. They were identified as kaempferol-3-O-(2″’-p-E-coumaroylrhamnosyl)(1″’→6″)-[β-D-glucopyranosyl-(1′″→2″)-β-D-glucopyranoside]-7-O-α-L-rhamnopyranoside, and quercetin-3-O-(2″’-p-E-coumaroylrhamnosyl)(1″’→6″)-[β-D-glucopyranosyl-(1″″→2″)-β-D-glucopyranoside]-7-O-α-L-rhamnopyranoside. Their structures were established on the basis of detailed spectral analysis.
Chemical Constituents of Equisetum Debile and their Cytotoxic Activity
Authors: Thai Tran Huy , Hung Nguyen Quang , Van Minh Chau , Cuong Nguyen Xuan , Yen Pham Hai , Huong Le Mai , Van Kiem Phan
Published: March 2019

A new phenyl glycoside, equisetumoside D (1), was isolated from the aerial parts of Equisetum debile, along with equisetumoside B (2), dehydrovomifoliol (3), corchoionoside C (4), (-)-isolariciresinol-3a-O-β-D-glucopyranoside (5), and kaempferol 3-O-sophoroside-7-O-β-D-glucopyranoside (6). Their structures were elucidated by NMR spectroscopic and MS experiments. Compound 1 was found to be cytotoxic against both tested human cancer cell lines, hepatocellular carcinoma (Hep-G2, IC50: 1.12 μg/mL) and rhabdosarcoma (RD, IC50: 0.25 μg/mL), while the other compounds showed no activity against these cell lines by in vitro assay.