Trivial Name Research Articles

The nutritional role of free sialic acid, a human milk monosaccharide, and its application as a functional food ingredient

ABSTRACT N-Acetyl-d-neuraminic acid (NANA), more commonly known by its trivial name sialic acid, is an endogenous human and ubiquitous nutritional monosaccharide. As a bound sugar at the terminal positions of glycans NANA is known to play important roles in many biological events. The data that exist on the occurrence of the free monosaccharide in breast milk and nutrition, however, are less commonly discussed. In most foods of animal origin, sialic acid occurs as a mixture of NANA and N-glycolyl-d-neuraminic acid (NGNA), a hydroxylated derivative of NANA that is not found in humans. The dietary intake of NGNA has been identified as a risk factor for long-term adverse health effects. Therefore, we present summaries on the biochemistry, metabolism, bioavailability, and the data on NANA and NGNA levels that occur in diverse foods. Finally, we discuss the emerging data demonstrating that free NANA is linked to positive nutritional effects including pronounced antioxidative properties. These data and the extremely high safety profile of NANA justify dietary enrichment at levels that correspond to the dietary intake of NANA in infants through breast milk.

Erratum to: Laboratory evaluation of five novel pyrrole derivatives as grain protectants against Tribolium confusum and Ephestia kuehniella larvae

Several naturally discovered or laboratory-synthesized pyrrole compounds have insecticidal, acaricidal and microbial properties. The novel sulfanyl 5H-dihydro-pyrrole derivatives exhibit certain antioxidant activities. However, there is a knowledge gap whether these substances are potent grain protectants against stored-product insect pest species. In this context, we evaluated the insecticidal activity of five novel pyrrole derivatives (under the trivial names 3a, 3g, 3l, 3m, 3h), against larvae of Tribolium confusum Jaquelin du Val and Ephestia kuehniella Zeller at different doses (0.1, 1 and 10 ppm), exposure intervals (7, 14 and 21 days or 1, 2, 7, 14, 21 days), temperatures (20, 25 and 30 °C), relative humidity (RH) (55 and 75 %) levels and commodities (wheat, maize, barley). The pyrrole derivative 3a exhibited the highest insecticidal activity, while 3g, 3l, 3m and 3h caused similar mortality against larvae of T. confusum. Apart of the level of efficacy, all tested pyrrole derivatives performed similarly according temperature. We found that increase in temperature increased mortality in the majority of the tested combinations. Generally, the pyrrole derivatives caused the highest mortality levels at 30 °C. The pyrrole derivatives 3a, 3g, 3l and 3m were affected by relative humidity at almost all combinations tested. The 75 % level of RH moderated the efficacy of the pyrrole derivatives, while the 55 % enhanced it. Mortality of T. confusum and E. kuehniella on maize was much lower on treated maize than barley or wheat. However, 100 % control of both species was recorded only on treated barley. The results of the present study indicate that the pyrrole derivatives tested could serve as grain protectants against noxious stored-product insects under certain biotic and abiotic conditions.

Fossil crinoids from the basal West Point Formation (Silurian), southeast Gaspé Peninsula, Québec, eastern Canada

Silurian strata of Atlantic Canada and southern Québec locally preserve common fossil crinoids, albeit mostly as disarticulated remains. New crinoids from the Chaleurs Group, West Point Formation (Ludlow to Pridoli?; Upper Silurian) of the Gaspé Peninsula include Iocrinus? maennili (Yeltysheva) (otherwise known from the Katian of Estonia), Bystrowicrinus (col.) depressus sp. nov. and Cyclocyclicus (col.) sp. aἀ. C. (col.) echinus Donovan. On the basis of both its gross morphology and stratigraphic position, Iocrinus? maennili is unlikely to be an iocrinid disparid, a family that became extinct at the end of the Ordovician. The trivial name has hitherto been erroneously spelled as männili, mannili and mjannili. Most specimens of the common Bystrowicrinus (col.) depressus appear cyclocyclic because the pentastellate lumen occurs in a deeply sunken claustrum that is commonly occluded by sediment; clean specimens are highly distinctive. Cyclocyclicus (col.) sp. aἀ. C. (col.) echinus is similar to a species known from the Katian of North Wales. Taken together, this assemblage is more reminiscent of Katian strata (Upper Ordovician). Ḁis is problematic given the current mapping of the outcrop as West Point Formation (Upper Silurian), suggesting further stratigraphic studies in the area are required.

Erucic acid in feed and food

Erucic acid is the trivial name of the fatty acid cis-13-docosenoic acid and occurs at high concentrations mainly in the seeds of species of the Brassicaceae (e.g. rape seed or mustard seed). The European Commission requested EFSA to deliver a scientific opinion on the risks for animal and human health related to the presence of erucic acid in feed and food. For most humans, the main contributor to dietary exposure to erucic acid was the food group ‘Fine bakery wares’. In ‘Infants’, ‘Food for infants and small children’ was the main contributor to exposure. The heart is the principal target organ for toxic effects after exposure. Myocardial lipidosis was identified as the critical effect for chronic exposure to erucic acid. This effect is reversible and transient during prolonged exposure. A tolerable daily intake (TDI) of 7 mg/kg body weight (bw) per day for erucic acid was established, based on a no observed adverse effect level of 0.7 g/kg bw per day for lipidosis in young rats and newborn piglets. Mean chronic exposure of the different groups of the population did not exceed the TDI. The 95th percentile dietary exposure level was highest in infants and other children, ranging from 1.3 to 7.4 mg/kg bw per day; the higher level being at the level of the TDI. This may indicate a risk for young individuals with high erucic acid exposure. In pigs, levels of erucic acid are unlikely to represent a health concern. However, for poultry, the small margin between the lowest observed adverse effect level (LOAEL) and the estimated exposure may indicate a health risk where maximum inclusion rates are applied. Due to the absence of adequate data, the risk for ruminants, horses, fish and rabbits could not be assessed.

Minor polysaccharidic constituents from the red seaweed Hypnea musciformis. Appearance of a novel branched uronic acid

Two polysaccharide fractions isolated from Hypnea musciformis after room temperature- and hot water extraction, soluble after KCl precipitation of the more abundant carrageenans, were subfractionated by ion-exchange chromatography eluting with increasing concentrations of NaCl. The lowest NaCl concentration (0.2M) eluted agarans. The dl-hybrids (or mixtures) eluted at intermediate concentrations of NaCl. The d/l-galactose ratio and the sulfate proportion increased with the NaCl concentration. Different types of substitution were present, mainly at C-3 with sulfate, Xyl and methylated Gal stubs, as well as low amounts of 3,6-AnGal. A novel constituent, identified as 3-C-carboxy-d-erythrose11According to the IUPAC rules for carbohydrates (Mc Naught, 1996; rule 18.3), the name of the acyclic form should be 3-C-hydroxymethyl-l-threuronic acid, whereas for the cyclic form, the ring closure takes precedence over the carboxyl group and thus, 3-C-carboxy-d-erythrofuranose should be imposed. (2R,3R)-apiuronic acid (ApiA) is used as an alternative trivial name throughout the text. in its β-furanosic form, was found linked to C-6 of β-Gal units. A search carried out in other species like Iridaea undulosa and Kappaphycus alvarezii also revealed the same constituent. Finally, the late-eluting fractions were mostly carrageenans, with a structure consistent with that of a κ/ι/ν-carrageenan hybrid.

Aldehyde dehydrogenases inhibition eradicates leukemia stem cells while sparing normal progenitors.

The vast majority of patients with acute myeloid leukemia (AML) achieve complete remission (CR) after standard induction chemotherapy. However, the majority subsequently relapse and die of the disease. A leukemia stem cell (LSC) paradigm has been invoked to explain this failure of CR to reliably translate into cure. Indeed, LSCs are highly enriched in CD34+CD38− leukemic cells that exhibit positive aldehyde dehydrogenase activity (ALDH+) on flow cytometry, these LSCs are resistant to currently existing treatments in AML such as cytarabine and anthracycline that, at the cost of great toxicity on normal cells, are highly active against the leukemic bulk, but spare the LSCs responsible for relapse. To try to combat the LSC population selectively, a well-characterized ALDH inhibitor by the trivial name of dimethyl ampal thiolester (DIMATE) was assessed on sorted CD34+CD38− subpopulations from AML patients and healthy patients. ALDH activity and cell viability were monitored by flow cytometry. From enzyme kinetic studies DIMATE is an active enzyme-dependent, competitive, irreversible inhibitor of ALDH1. On cells in culture, DIMATE is a powerful inhibitor of ALDHs 1 and 3, has a major cytotoxic activity on human AML cell lines. Moreover, DIMATE is highly active against leukemic populations enriched in LSCs, but, unlike conventional chemotherapy, DIMATE is not toxic for healthy hematopoietic stem cells which retained, after treatment, their self-renewing and multi-lineage differentiation capacity in immunodeficient mice, xenografted with human leukemic cells. DIMATE eradicates specifically human AML cells and spares healthy mouse hematologic cells.

The essential oil of Achillea ageratifolia (Sm.) Boiss. subsp. serbica (Nyman) Heimerl (Asteraceae) revisited: the stereochemical nomenclature issues, structural elucidation and synthesis of (new) sabinyl esters

AbstractSerbian Yarrow (Achillea ageratifolia (Sm.) Boiss. subsp. serbica (Nyman) Heimerl, Asteraceae) is a poorly investigated taxon, endemic to the Central Balkan Peninsula area. A combination of chromatographic and spectroscopic techniques enabled the identification of, in total, 300 constituents (comprising 95.5–97.2% of the total essential oil compositions) from the essential oils of the A. ageratifolia ssp. serbica dry aerial parts. A comparison of the essential‐oil compositions from plant material collected from two populations (Jelašnička klisura gorge and Suva Planina mountain, SE Serbia) in two consecutive years (2013 and 2014) confirmed that the biosynthesis/accumulation of the volatile metabolites for this species is not dependent on the environmental conditions and suggested the existence of a single chemotype of this species. The essential oil compositions were dominated by (1R*,3S*,5R*)‐sabinyl derivatives, including two completely new natural products: (1R*,3S*,5R*)‐sabinyl nonanoate and (1R*,3S*,5R*)‐sabinyl decanoate. The identity of these new esters was unambiguously confirmed by co‐injection of the essential oil samples with synthesized standards and their structure was elucidated by NMR (1D and 2D), IR and MS, whereas the stereochemistry of the esters was studied by an NMR methodology that employed lanthanide‐induced shift reagents. Additionally, a nomenclature confusion regarding the relative stereochemistry of sabinyl esters, that came from the opposing use of cis and trans for the parent alcohols and the derived esters, was addressed. We propose the use of CIP notation in connection with the trivial names to avoid further ambiguities. Copyright © 2016 John Wiley & Sons, Ltd.

Iriflophenone Glycosides from Aquilaria sinensis

Five iriflophenone glycosides were obtained from the stems of Aquilaria sinensis by phytochemical methods. Their structures were determined by spectroscopic methods and comparison with literature data. As a novel compound, compound 1 was given a trivial name aquilarinoside B.

ChemInform Abstract: Polyketides from the Mangrove‐Derived Fungal Endophyte Pestalotiopsis clavispora.

AbstractPestalpolyol I (I), pestapyrones A (IIa) and B (IIb), (R)‐periplanetin D (III), pestaxanthone (IV), and norpestaphthalide A (V) are isolated from Pestalotiopsis clavispora.

ChemInform Abstract: Medusamide A, a Panamanian Cyanobacterial Depsipeptide with Multiple β‐Amino Acids.

From a collection of marine cyanobacteria made in the Coiba National Park along the Pacific coast of the Republic of Panama a novel cyclic depsipeptide, given the trivial name medusamide A, has been isolated and fully characterized. Medusamide A contains four contiguous β-amino acid (2R,3R)-3-amino-2-methylhexanoic acid (Amha) residues. This is the first report of multiple Amha residues and contiguous β-amino acid residues within a single cyclic peptide-type natural product. Stereochemical assignment of the Amha residues was completed following the synthesis of reference standards for this β-amino acid and the subsequent derivatization with Marfey’s reagent and LC–MS analysis.

Half a Century of Hawaiian Marine Natural Products.

The following review covers the primary literature concerning marine natural products isolated for the first time from organisms collected around the islands of Hawaii published in the 51-year period 1964 to July 2015. The review is divided into seven main sections based on major taxonomic groupings; algae, sponges, mollusks, miscellaneous invertebrates, cyanobacteria, bacteria, and fungi. The aim of the review is to discuss the compounds and information concerning their original biological activity and other potentially interesting properties. The majority of the 320 structures of isolated compounds are not shown directly in the review but are contained in the Supporting Information section in 22 figures, Figs. 1 S-22 S. The Supporting Information section also contains Table 1 S that has information relating to the taxonomic identification of the source organism of each compound, collection location of the source organism, a trivial or semi-systematic name for each compound, as well as its general structural class. The authors hope that this review will be the spawning ground for other reviews and the basis for a great deal more research into the marine life found in Hawaiian waters.

Engyodontochones, Antibiotic Polyketides from the Marine Fungus Engyodontium album Strain LF069

Six new (2, 4-8) and two known polyketides with a basic structure of an anthraquinone-xanthone were isolated from mycelia and culture broth of the fungus Engyodontium album strain LF069. The structures and relative configurations of these compounds were established by spectroscopic means, and their absolute configurations were defined mainly by comparison of quantum chemical TDDFT calculated and experimental ECD spectra. Compounds 2 and 4-8 were given the trivial names engyodontochone A (2) and B-F (4-8). Compounds 5-8 represent the first example of a 23,28 seco-beticolin carbon skeleton. The relative and absolute configurations of two known substances JBIR-97/98 (1) and JBIR-99 (3) were determined for the first time. All isolated compounds were subjected to bioactivity assays. Compounds 1-4 exhibited inhibitory activity against methicillin-resistant Staphylococcus aureus (MRSA) that was 10-fold stronger than chloramphenicol.

Novel archaeal tetraether lipids with a cyclohexyl ring identified in Fayetteville Green Lake, NY, and other sulfidic lacustrine settings.

The meromictic Fayetteville Green Lake (FGL) is of significant geobiological interest because of microbial cycling of sulfur within and below the permanent chemocline and in the euxinic deep waters. Studies of glycerol dibiphytanyl glycerol tetraethers (GDGTs) may help shed light on understanding the activity of archaeal communities in these habitats. Normal-phase and reversed-phase liquid chromatography/mass spectrometry (LC/MS) analysis on total lipid extracts of environmental samples revealed series of GDGTs with different biphytane structures. Comparison of the mass spectrum of biphytane obtained from separated novel GDGTs with that of a synthetic C40 biphytane confirms our structural assignments. A unique cyclohexyl ring configured in the middle of a C40 biphytane chain was identified in these novel GDGTs. We suggest the trivial name S-GDGTs for these compounds, where 'S' stands for 'sulfidic' and 'six-membered ring'. S-GDGT derivatives composed of biphytanes modified with double bonds and cyclopentane rings were also detected in the samples we analyzed. Intact polar lipid precursors of S-GDGT include compounds with mono- and diglycosyl head groups. The carbon isotopic composition of S-GDGTs and their occurrence in FGL, Messel Shale as well as Salt Pond and salt marshes on Cape Cod suggest that S-GDGTs may be produced by chemoautotrophic archaea that prefer sulfidic conditions. Copyright © 2016 John Wiley & Sons, Ltd.

Polyketides from the Mangrove-derived fungal endophyte Pestalotiopsis clavispora

Six new polyketide derivatives, including pestalpolyol I (1), pestapyrones A (2) and B (3), (R)-periplanetin D (6), pestaxanthone (7), norpestaphthalide A (8), and an isolation artifact pestapyrone C (4), were obtained from extracts of the endophytic fungus Pestalotiopsis clavispora isolated from the Mangrove plant Rhizophora harrisonii. In addition, seven known metabolites, including similanpyrone B (5), (R,S)-5,7-dihydroxy-3-(1-hydroxyethyl)phthalide (9), for which we propose the trivial name norpestaphthalide B, pestaphthalides A (10) and B (11), 2-epi-herbarumin II (12), and pestalotiollides A (13) and B (14) were isolated. The structures of the new compounds were unambiguously elucidated on the basis of one- and two-dimensional NMR spectroscopy, as well as by high-resolution mass spectrometry. All compounds were tested for their cytotoxicity against the mouse lymphoma cell line L5178Y. Compound 1 exhibited strong activity with an IC50 value of 4.10μM. All other compounds (2–14) proved to be inactive (IC50>10μM) in this assay.

Fatty acid esters produced by Lasiodiplodia theobromae function as growth regulators in tobacco seedlings

The Botryosphaeriaceae are a family of trunk disease fungi that cause dieback and death of various plant hosts. This work sought to characterize fatty acid derivatives in a highly virulent member of this family, Lasiodiplodia theobromae. Nuclear magnetic resonance and gas chromatography-mass spectrometry of an isolated compound revealed (Z, Z)-9,12-ethyl octadecadienoate, (trivial name ethyl linoleate), as one of the most abundant fatty acid esters produced by L. theobromae. A variety of naturally produced esters of fatty acids were identified in Botryosphaeriaceae. In comparison, the production of fatty acid esters in the soil-borne tomato pathogen Fusarium oxysporum, and the non-phytopathogenic fungus Trichoderma asperellum was found to be limited. Ethyl linoleate, ethyl hexadecanoate (trivial name ethyl palmitate), and ethyl octadecanoate, (trivial name ethyl stearate), significantly inhibited tobacco seed germination and altered seedling leaf growth patterns and morphology at the highest concentration (0.2 mg/mL) tested, while ethyl linoleate and ethyl stearate significantly enhanced growth at low concentrations, with both still inducing growth at 98 ng/mL. This work provides new insights into the role of naturally esterified fatty acids from L. theobromae as plant growth regulators with similar activity to the well-known plant growth regulator gibberellic acid.

Medusamide A, a Panamanian Cyanobacterial Depsipeptide with Multiple β-Amino Acids.

From a collection of marine cyanobacteria made in the Coiba National Park along the Pacific coast of the Republic of Panama a novel cyclic depsipeptide, given the trivial name medusamide A, has been isolated and fully characterized. Medusamide A contains four contiguous β-amino acid (2R,3R)-3-amino-2-methylhexanoic acid (Amha) residues. This is the first report of multiple Amha residues and contiguous β-amino acid residues within a single cyclic peptide-type natural product. Stereochemical assignment of the Amha residues was completed following the synthesis of reference standards for this β-amino acid and the subsequent derivatization with Marfey's reagent and LC-MS analysis.

Spiromastilactones: A new class of influenza virus inhibitors from deep-sea fungus

A new class of phenolic lactones with trivial names of spiromastilactones A-M (1–13) was isolated from a deep-sea derived Spiromastix sp. fungus. Their structures featured by various chlorination at aromatic rings were determined on the basis of extensive spectroscopic analyses. An antiviral assay revealed that most of the tested compounds exert inhibitory activity against WSN influenza virus with low cytotoxicity, while the structure–activity relationships were discussed. Spiromastilactone D (4), a 5′-chloro-2′-methoxy substituted analogue, displayed the most potent to inhibit a panel of influenza A and B viruses in addition to drug-resistant clinical isolates. Mechanistic investigation resulted in that compound 4 bonded to hemagglutinin protein (HA), potentially at the spherical head, and disrupted the HA-sialic acid receptor interaction, that is essential for the attachment and entry of all influenza viruses. In addition, compound 4 also showed inhibitory effect toward viral genome replication via targeting viral RNP complex. The synergistic effects of 4 on both viral entry and replication assumed it to be a promising lead for the development of a new influenza inhibitor.

Prasiolin, a new UV-sunscreen compound in the terrestrial green macroalga Prasiola calophylla (Carmichael ex Greville) Kützing (Trebouxiophyceae, Chlorophyta).

Main conclusionWe introduced a novel combination of chromatographic techniques for the purification and analysis of a new UV-sunscreen mycosporine-like amino acid (MAA) in the terrestrial green algaPrasiola calophylla.Prasiola calophylla (Carmichael ex Greville) Kützing (Trebouxiophyceae, Chlorophyta) is a typical member of terrestrial algal communities in temperate Europe, where it regularly experiences various stress conditions including strong diurnal and seasonal fluctuations in ultraviolet radiation (UVR). As a photoprotective mechanism Prasiola species and other related Trebouxiophycean taxa synthesize a mycosporine-like amino acid (MAA) as natural sunscreen whose chemical structure was unknown so far. In the present study a new methodological approach is described for the isolation, purification and structural elucidation of this novel sunscreen in P. calophylla. The new compound exhibits an absorption maximum at 324 nm (in the short ultraviolet-A), a molecular weight of 333 and a molecular extinction coefficient of 12.393 M−1 cm−1, and could be identified as N-[5,6 hydroxy-5(hydroxymethyl)-2-methoxy-3-oxo-1-cycohexen-1-yl] glutamic acid using one- and two-dimensional 1H and 13C-NMR spectroscopy. As trivial name for this novel MAA we suggest ‘prasiolin’. The ecologically essential function of prasiolin for UVR-protection in terrestrial algae of the Trebouxiophyceae is discussed.

4-Methoxycinnamic acid – An unusual phenylpropanoid involved in phenylphenalenone biosynthesis in Anigozanthos preissii

In vitro root cultures of Anigozanthos preissii and Wachendorfia thyrsiflora (Haemodoraceae) are suitable biological systems for studying the biosynthesis of phenylphenalenones. Here we report how we used these root cultures to investigate precursor–product relationships between phenylpropanoids and phenylphenalenones whose phenyl rings share identical substitution patterns. Four phenylpropanoic acids, including ferulic acid and the unusual 4-methoxycinnamic acid, were used in 13C-labeled form as substrates to study their incorporation into phenylphenalenones. In addition to the previously reported 2-hydroxy-9-(4′-hydroxy-3′-methoxyphenyl)-1H-phenalen-1-one (trivial name musanolone F), 2-hydroxy-9-(4′-methoxyphenyl)-1H-phenalen-1-one (proposed trivial name 4′-methoxyanigorufone) was found as a biosynthetic product in A. preissii. The carbon skeleton of 4′-methoxycinnamic acid was biosynthetically incorporated as an intact unit including its 4′-O-methyl substituent at the lateral phenyl ring. 4′-Methoxyanigorufone is reported here for the first time as a natural product.

Silphiperfolene-Type Terpenoids and Other Metabolites from Cultures of the Tropical Ascomycete Hypoxylon rickii (Xylariaceae).

A culture isolated from ascospores of Hypoxylon rickii, a xylariaceous ascomycete collected in Martinique, had yielded botryane, noreremophilane and abietane-type terpenoids in a preceding study, but additional metabolites were detected by extensive HPLC–MS analysis in other fractions. Herein we report the further isolation of four new sesquiterpenoids with a silphiperfol-6-ene skeleton from extracts of H. rickii. The planar structures were elucidated by NMR and HRMS data as 13-hydroxysilphiperfol-6-ene (1), 9-hydroxysilphiperfol-6-en-13-oic acid (2), 2-hydroxysilphiperfol-6-en-13-oic acid (3) and 15-hydroxysilphiperfol-6-en-13-oic acid (4). For compounds 2–4 we propose the trivial names rickinic acids A–C. Their stereochemistry was assigned by ROESY correlations as well as by the specific optical rotation. Additionally, the known compounds, botryenanol, dehydrobotrydienol, cyclo(Phe-Pro), cyclo(Pro-Leu), (+)-ramulosin and α-eleostearic acid were isolated. The antimicrobial and cytotoxic activities of the new compounds are also reported.Graphical Electronic supplementary materialThe online version of this article (doi:10.1007/s13659-015-0065-3) contains supplementary material, which is available to authorized users.