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Stauntonia brachyanthera Hand-Mazz., known as zhuyaozi or north banana by Dong Ethnicity in the southwest of China, is widely accepted as a delicious fruit with high economic value because of the presence of health-promoting components and the delivery of new tastes. In search for antioxidant compounds, the activity-guided fractionation and purification processes were performed on the stems and roots of S. brachyanthera, which resulted in the isolation of six new compounds, brachyanin A–F (1–6), and seven known compounds (7–13). Their structures were elucidated by 1D and 2D NMR, and HR-ESI-MS. Brachyanin A (1) exhibited significant cytotoxicity against HepG2 and K562 cell lines with IC50 values of 6.93 and 7.89 µM, respectively, and possessed antioxidant activity. Six compounds presented stronger antioxidant activities than those of vitamin C and quercetin in three tests (DPPH, ABTS, and FRAP). Among them, calceolarioside B (9) exhibited strongest activity and was present in higher amounts in the plant, which could be designated as characteristic component for the pharmacognostic identification and the quality control of S. brachyanthera. These findings laid solid theoretical references for the exploration of traditional usage of S. brachyanthera.

The chemical constituents of the seeds of Moringa oleifera were isolated and purified by using Sephadex LH-20, Toyo-pearl HW-40F, silica gel, ODS, and MCI column chromatography. The structures of compounds were identified by high-resolution mass spectrometry, ~1H-NMR, ~(13)C-NMR, HMQC, HMBC, and ~1H-~1H COSY, as well as physicochemical properties of compounds and literature data. Twelve compounds were isolated from 30% ethanol fraction of the seeds of M. oleifera and identified as ethyl-4-O-α-L-rhamnosyl-α-L-rhamnoside(1), ethyl-3-O-α-L-rhamnosyl-α-L-rhamnoside(2),(4-hydroxybenzyl)ethyl carbamate(3),(4-aminophenyl)acetic acid(4), ethyl-α-L-rhamnoside(5), methyl-α-L-rhamnoside(6), moringapyranosyl(7), 2-[4-(α-L-rhamnosyl)phenyl]methyl acetate(8), niaziridin(9), 5-hydroxymethyl furfural(10), 4-hydroxybenzeneacetamide(11), and 4-hydroxybenzoic acid(12). Among them, compounds 1 and 2 are two new compounds, compound 3 is a new natural product, and compounds 4-5 were yielded from Moringa plant for the first time. All compounds were evaluated for α-glucosidase inhibitory activity in vitro. Compound 10 showed excellent inhibitory activity with IC_(50) of 210 μg·mL~(-1).

Eight heterocyclic compounds and twelve phenolic glycosides were separated from the water extract of Dendrobium officinale flowers through chromatographic techniques, such as Diaion HP-20 macroporous adsorption resin column chromatography(CC), silica gel CC, ODS CC, Sephadex LH-20 CC, and preparative high performance liquid chromatography(PHPLC). According to the spectroscopic analyses(MS, ~1H-NMR, and ~(13)C-NMR) and optical rotation data, the compounds were identified as dendrofurfural A(1), 2'-deoxyadenosine(2), 4-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl] butanoic acid(3), 4-[2-formyl-5-(methoxymethyl)-1H-pyrrol-1-yl] butanoic acid(4), 1-(2-hydroxyethyl)-5-(methoxymethyl)-1H-pyrrole-2-carbaldehyde(5), 5-(methoxymethyl)-1H-pyrrole-2-carbaldehyde(6), methyl 5-(hydroxymethyl)-furan-2-carboxylate(7),(S)-5-hydroxymethyl-5H-furan-2-one(8), 2-methoxyphenyl-1-O-β-D-glucopyranoside(9), arbutin(10), isotachioside(11), 2,6-dimethoxy-4-hydroxyphenol-1-O-β-D-glucopyranoside(12), orcinol glucoside(13), tachioside(14), gastrodin(15), 4-O-β-D-glucopyranosylvanillyl alcohol(16), 2,6-dimethoxy-4-hydroxymethylphenol-1-O-β-D-glucopyranoside(17), icariside D_2(18), 4-formylphenyl-β-D-glucopyranoside(19), and vanillin-4-O-β-D-glucopyranoside(20). Among them, compound 1 is a new furfural benzyl alcohol condensate, with the skeleton first found in Dendrobium. Compounds 2-9, 11, 13, and 19 are reported from Dendrobium for the first time, and compounds 14 and 18 are reported for the first time from D. officinale. Compounds 11 and 14 showed moderate DPPH radical scavenging capacity, and compounds 11-14 demonstrated potent ABTS radical scavenging capacity, possessing antioxidant activity.

The foraging ecology of mammalian herbivores is determined by plant secondary compounds (PSC) that defend plants against herbivory, by nutrients that are required for maintenance, growth, and reproduction, and by the interaction between these variables. In this study, we explored the influence of an herbivore’s nutritional state and experience on intake of aspen ( Populus tremuloides ) leaves with contrasting concentrations of a PSC, phenolic glycosides (PG). Thirty-two lambs were randomly assigned to two groups (N = 16). Each group received aspen leaves with either higher (21.2%) or lower (16.3%) concentrations of PG throughout the study. In Experiment 1, half of the lambs within each group received rations with a high (22.2% crude protein [CP]; 3.13 Mcals/kg) or low (11.9% CP; 3.13 Mcals/kg) concentration of CP. During Experiment 2, half of the lambs within each group received rations with a high (3.45 Mcals/kg; 16.1% CP) or low (2.52 Mcals/kg; 18.5% CP) concentration of energy. During Experiment 3, all lambs received a simultaneous offer of aspen leaves containing higher (20.6%) and lower (14.8%) concentrations of PG. Aspen intake was greater when lambs received the high-protein or the low-energy rations (P < 0.05), and when they received aspen leaves with lower concentrations of PG (P = 0.009). During Experiment 3 (choice of high- or low-PG aspen), aspen intake was not affected by PG, but intake increased when nutrients were present in aspen in a combination of low concentrations of Cu, P, K, S, crude protein, and an intermediate concentration of condensed tannins. In summary, nutritional state and aspen chemical composition modulated the extent to which aspen was consumed by lambs. Herbivores grazing plant communities with high concentrations of protein or low concentrations of energy may be more likely to consume greater amounts of aspen than those animals grazing forages with low concentrations of protein or high concentrations of energy. This knowledge can be applied at the landscape level to identify potential “at-risk areas” of aspen regeneration and recruitment, allowing for the development of supplementation programs that reduce aspen herbivory. [ABSTRACT FROM AUTHOR]

Two new phenolic glycosides, 7 S , 8 R -urolignoside-9′- O - β -D-glucoside ( 1 ) and scrophenoside G ( 2 ), were isolated and identified from the seeds of Ginkgo biloba L., a famous traditional medicine and functional food around the world. Their structures were elucidated by spectroscopic methods (1D and 2D NMR, HR-ESI-MS, and CD), and the comparisons of spectroscopic data with the reported values in the literature. [ABSTRACT FROM AUTHOR]

Two new phenolic glycosides (1 and 2) and two new isocoumarin glycosides (3 and 4), along with 14 known compounds (5–18), were isolated from the stems of Homalium paniculiflorum. Their structures were established on the basis of extensive spectroscopic analyses and chemical methods. All new compounds were evaluated for their anti-inflammatory activities via examining the inhibitory activity on nitric oxide (NO) production induced by lipopolysaccharide (LPS) in mouse macrophage RAW 264.7 cells in vitro. Compounds 1 and 4 exhibited inhibitory activities with IC50 values of 30.23 ± 1.23 μM and 19.36 ± 0.19 μM, respectively. [ABSTRACT FROM AUTHOR]

The fate of carbon (C) captured by forest trees during photosynthesis is influenced by the supply of other resources. Fixed C may be partitioned among biomolecules within the leaf and/or allocated throughout the tree to growth, storage and maintenance activities. Phosphorus (P) availability often limits tree productivity due to its high biological demand and strong interactions with soil minerals. As ectomycorrhizal (ECM) fungi play critical roles in enhancing phosphate (Pi) acquisition by their hosts, these symbioses will influence the fate of C within trees and forested ecosystems. Using Populus tremuloides Michx. (trembling aspen) in symbiosis with Laccaria bicolor (Marie) P.D. Orton or Paxillus involutus (Batsch) Fr., we assessed C acquisition, allocation and partitioning under Pi limitation, specifically focusing on primary and secondary C compounds. Both ECM fungi moderated the effects of low P on photosynthesis and C partitioning among carbohydrates and secondary metabolites by sustaining Pi uptake and translocation in P. tremuloides under Pi limitation. As leaf P declined, reductions in photosynthesis were accompanied by significant shifts in C partitioning from nonstructural carbohydrates (NSCs) to phenolic glycosides and tannins. Carbon partitioning in roots exhibited more complex patterns, with distinct increases in NSCs in nonmycorrhizal (NM) plants under Pi limitation that were not evident in plants colonized by either ECM symbiont. In general, aspen colonized by L. bicolor exhibited C partitioning patterns intermediate between those of NM and P. involutus aspen. The C cost of symbiosis was pronounced for plants supporting P. involutus, where ECM plants exhibited maintenance of photosynthesis yet reduced biomass in comparison with NM and L. bicolor aspen under Pi replete conditions. Our results indicate that the ECM symbiosis affects the disposition of C in forest trees in part by altering the acquisition of other limiting resources from soils, but also through ECM species-specific influences on host physiology. This modulation of C partitioning will have broad implications for forest ecosystem C capture, storage and cycling where nutrient resources may be limited. [ABSTRACT FROM AUTHOR]

In view of the significant neuroprotective effect of Clausena lansium, we continued to separate the n-butanol and the water extracts from the stems of C. lansium in order to find the leading compounds with significant activity. Two new phenolic glycosides, Clausenolside A-B (1-2), one new pair of phenolic enantiomers (3a, 3b), and two new monoterpenoids, clausenapene A-B (4-5), together with twelve known analogues (6-17) were isolated from the stems of C. lansium. Compounds 1-17 were obtained from C. lansium for the first time. Compounds 3a, 3b, 4, 16, and 17 showed strong or moderate potential neuroprotective effects on inhibited PC12 cell injury induced by okadaic acid, and compound 9 exhibited strong potential hepatoprotective activities. Their structures were elucidated on the basis of spectroscopic analyses, including UV, IR, NMR experiments, and electronic circular dichroism (ECD) spectra. [ABSTRACT FROM AUTHOR]

Quantum mechanics (QM)-based calculations for elucidating full structures of natural compounds are growing in importance and reliability. Two new phenolic glycosides ( 1 and 2 ) and 11 known compounds were isolated from the twigs of Spiraea prunifolia var. simpliciflora . The chemical structures of the new compounds ( 1 and 2 ) were initially established through different NMR techniques ( 1 H and 13 C NMR, COSY, HSQC, and HMBC), HRMS data analysis, and chemical hydrolysis. These structure assignments were further verified by QM-based NMR chemical shift calculations. All of the purified compounds ( 1 – 13 ) were evaluated for their cytotoxicity against four human cancer cell lines (A549, SK-OV-3, SK-MEL-2, and BT549). Those phytochemicals were also evaluated for both anti-inflammatory activity through the measurement of nitric oxide (NO) production levels in lipopolysaccharide (LPS)-stimulated murine microglia BV-2 cell lines and neuroprotective effects via induction of nerve growth factor (NGF) in C6 glioma cells. [ABSTRACT FROM AUTHOR]

Phytochemical investigation of Idesia polycarpa (Salicaceae) resulted in the structure elucidation of nine previously undescribed phenolic natural products along with six known compounds. The compounds are structurally related to salicinoids that are known defense compounds from Salix and Populus species. The I. polycarpa diet was toxic, as shown in feeding experiments with larvae of Lymantria dispar , an herbivorous broadleaf tree generalist insect, and with larvae of Cerura vinula , a specialist adapted to poplar. The survival rate and mass gain of larvae was significantly lower when they fed on I. polycarpa leaves, compared to larvae fed on Populus nigra leaves. Potential reasons for the poor performance of both herbivores on I. polycarpa leaves are discussed. [ABSTRACT FROM AUTHOR]

The roots of Ilex asprella (Rla) are a well-known traditional Chinese medicine for the treatment of viral and bacterial infectious diseases, such as influenza, tonsillitis, sphagitis, and trachitis. However, due to the complexity of the chemical constituents in Rla , few investigations have acquired a comprehensive understanding of material basis. High-performance liquid chromatography coupled to electrospray ionisation and quadrupole time-of-flight mass spectrometry (HPLC-ESI-QTOF-MS/MS) was used for the identification of chemical constituents from the extract of Rla in negative ion mode. Their chemical structures were tentatively elucidated based on exact formulas, fragmentation patterns and literature data. A total of 32 compounds were discovered and tentatively characterised in Rla, including 4 phenolic glycosides and 28 triterpenoid glycosides. 10 compounds have not been previously reported in Rla and 8 of them have not been previously reported in the literature. The chemical composition of Rla was identified and summarised, providing a basis for further study on Rla. [Display omitted] • It was the first time to elucidate the chemical profiling of Ilex asprella by HPLC-ESI-QTOF-MS/MS. • A total of 32 compounds were discovered and tentatively characterised in Rla. • The chemical structures of 8 new compounds were tentatively elucidated. [ABSTRACT FROM AUTHOR]

Foeniculum vulgare (Apiaceae) commonly known as fennel is a well known and important medicinal and aromatic plant widely used as carminative, digestive, lactogogue and diuretic and in treating respiratory and gastrointestinal disorders. Its seeds are used as flavourings in baked goods, meat and fish dishes, ice cream, alcoholic beverages and herb mixtures. Phenols, phenolic glycosides and volatile aroma compounds such as trans-anethole, estragole and fenchone have been reported as the major phytoconstituents of this species. Different pharmacological experiments in a number of in vitro and in vivo models have convincingly demonstrated the ability of F. vulgare to exhibit antifungal, antibacterial, antioxidant, antithrombotic and hepatoprotective activities, lending support to the rationale behind several of its therapeutic uses. Phenolic compounds isolated from F. vulgare are considered to be responsible for its antioxidant activity while the volatile aroma compounds make it an excellent flavouring agent. The present review is an up-to-date and comprehensive analysis of the chemistry, pharmacology, traditional uses and safety of F. vulgare.

Salix triandra (almond leaved willow) is an established crop, grown in coppicing regimes for basket-making materials. It is known as a source of non-salicinoid phenolic glycosides, such as triandrin and salidroside. A spontaneous natural hybrid of S. triandra and S. dasyclados was subjected to metabolite profiling by high resolution LC-MS, and 22 phenolic glycosides, including 18 that are new to the Salicaceae, were identified. Structures were determined by HPLC isolation and NMR methods. The hybridisation process has introduced novel chemistry into the Salix phenolic glycoside palette, in particular, the ability to generate disaccharide conjugates where the glycosyl group is further extended by a range of sugars, including apiose, rhamnose, xylose, and arabinose. Also of note is the appearance of chavicol derivatives, also not previously seen in Salix spp. The work demonstrates the plasticity of the phenolic glycoside biosynthetic pathway, and the potential to improve established crops such as S. triandra and S. dasyclados, via high-value metabolites, for both basketry and bioenergy markets.

Seven new phenolic glycosides including two heterocyclic phenolic derivatives orcinosides I-J ( 1–2 ) and five chlorophenolic glycosides curculigines J-N ( 3 – 7 ), together with nineteen known compounds were isolated from the rhizome of Curculigo orchioides . Based on extensive spectroscopic analyses (UV, IR, HRESIMS, 1D and 2D NMR), the structures of the new compounds were identified. Orcinoside I ( 1 ) and J ( 2 ) displayed xanthine oxidase inhibitory activities with IC 50 values 0.25 and 0.62 mM respectively. [ABSTRACT FROM AUTHOR]

Objective To find the genuine structure with anti-acetylcholinesterase (anti-AChE) from the phenolic glycosides abundant in Leonurus japonicus (Lamiaceae). The assay for anti-AChE activity is often used to lead anti-Alzheimer's drugs. Methods The five phenolic glycosides, tiliroside, leonurusoside C, 2‴-syringoylrutin, rutin, and lavanduliofolioside were isolated from L. japonicus . The activities of the glycosides were relatively low. Seven compounds including p -coumaric acid, caffeic acid, hydroxytyrosol, salidroside, syringic acid, kaempferol, and quercetin, which are produced by the hydrolysis of the five glycosides, were also assayed for anti-AChE activity. Results Of those seven compounds, the five compounds other than salidroside and syringic acid exhibited potent anti-AChE activities. In particular, the IC 50 s of caffeic acid and quercetin were (1.05 ± 0.19) and (3.58 ± 0.02) μg/mL, respectively. Rutin was the most abundant flavonoid in the extract (9.18 mg/g as measured by HPLC). Conclusion The substances with potent anti-AChE were caffeic acid, quercetin, p -coumaric acid, kaempferol, and hydroxytyrosol that can be produced from their glycosides. [ABSTRACT FROM AUTHOR]

Three new phenolic glycosides ( 1–3 ) together with nine known ones were isolated from the roots of Tecoma mollis using DPPH radical scavenging bioassay-guided chromatographic separation. The structures of the new compounds were established using extensive spectroscopic data and HR-MS. The antioxidant, COX-2 inhibition, and cytotoxic activities were evaluated for the isolated compounds. Compound 4 displayed the strongest radical scavenging activity relative to ascorbic acid with IC 50 8.7 μM. Compounds 5 , 6 , and 10 showed promising COX-2 inhibitory action, IC 50 values of 11.3 μM, 9.4 μM, and 13.4 μM, respectively. All compounds exhibited weak cytotoxic activity against Hela and A549 cancer cell lines. [ABSTRACT FROM AUTHOR]

Nutrients and plant secondary compounds in aspen ( Populus tremuloides) may interact with nutrients in the surrounding vegetation to influence aspen use by herbivores. Thus, this study aimed to determine aspen intake and preference by sheep in response to supplementary nutrients or plant secondary compounds (PSC) present in aspen trees. Thirty-two lambs were randomly assigned to one of four molasses-based supplementary feeds to a basal diet of tall fescue hay ( N = 8) during three experiments. The supplements were as follows: (1) high-protein (60% canola meal), (2) a PSC (6% quebracho tannins), (3) 25% aspen bark, and (4) control (100% molasses). Supplements were fed from 0700 to 0900, then lambs were fed fresh aspen leaves collected from stands containing high (Experiment 1, 2) or low (Experiment 3) concentrations of phenolic glycosides (PG). In Experiment 2, lambs were simultaneously offered aspen, a forb ( Lathyrus pauciflorus), and a grass ( Bromus inermis) collected from the aspen understory. Animals supplemented with high protein or tannins showed greater intake of aspen leaves than animals supplemented with bark or the control diet ( P < 0.05), likely because some condensed tannins have a positive effect on protein nutrition and protein aids in PSC detoxification. Overall, animals supplemented with bark showed the lowest aspen intake, suggesting PSC in bark and aspen leaves had additive inhibitory effects on intake. In summary, these results suggest that not only the concentration but also the types and proportions of nutrients and chemical defenses available in the plant community influence aspen use by herbivores. [ABSTRACT FROM AUTHOR]

The leaves of Aquilaria crassna (Thymelaeaceae) are recently become an attractive research due to their potential in antioxidative, antibacterial, antipyretic, analgesic, and laxative activities. However, the neuritogenic and neuroprotective effects of A. crassna leaves have never been reported. In this study, three phenolic glycosides were isolated from A. crassna leaves. The isolates were identified as genkwanin 5- O-β-primevoside ( 1), iriflophenone 3,5- C-β- d-diglucoside ( 2) and iriflophenone 3-C-β - d -glucoside ( 3). The neuroprotective and neuritogenic activities of these compounds were evaluated. Compound 1 and 2, at very low concentration (100 ng/mL of compound 1 and 1 ng/mL of compound 2), exhibited the protection of P19-derived neurons and promoted the neurite outgrowth of the cultured neurons. In addition, a preliminary study on these compounds revealed that there was no correlation between their antioxidative properties and their neuroprotective activities. Practical applications Agarwood leaves have been used as an ingredient in foods and drinks for health promotion in Asian countries. The results of this study also suggest that Aquilaria crassna leaves are potentially sources of neuritogenic and neuroprotective constituents, which may be developed as functional foods for the prevention of neurodegenerative disorder. [ABSTRACT FROM AUTHOR]

Three new compounds, apetalumosides C1 (1), D (2), and 1-thio-β-D-glucopyranosyl(1→1)-1-thio-α-D-glucopyranoside (3), together with twenty-two known ones (4-25) were obtained from the seeds of Lepidium apetalum Willd. Among the known isolates, 5-8, 10-13, 16-20, and 25 were obtained from the genus for the first time; 4, 14, 15, and 21-24 were isolated from the species for the first time. Meanwhile, the NMR data of 16 was first reported here. Their structures were determined by means of chemical and spectroscopic methods. On the other hand, their inhibitory effects on sodium oleate-induced triglyceride (TG) overloading in HepG2 cells were evaluated. As a resulţ two new compounds (1 and 2), together with known isolates 7-11, 13, 14, 16-18, 20, 21, and 25 possessed significant inhibitory effects in the cells. [ABSTRACT FROM AUTHOR]

Two new phenolic glycosides with a rare β- d -glucopyranosyl-(1 → 3)-α- l -rhamnopyranosyl moiety ( 1 , 2 ), one new dihydrobenzofuran derivative ( 3 ), one new pyrazine derivative ( 4 ), two new furofuran lignan glycosides ( 5 , 6 ), and six known compounds ( 7 – 12 ) were isolated from the rhizomes of Atractylodes lancea . The structures of these compounds were elucidated by extensive spectroscopic analyses combined with the experimental and calculated electronic circular dichroism and the Rh 2 (OCOCF 3 ) 4 -induced circular dichroism for configurational assignments. Notably, compounds 1 – 3 showed significant hepatoprotective activities against N -acetyl- p -aminophenol-induced HepG2 cell injury. This study is also the first Letter on the isolation of furofuran lignans and pyrazine derivatives ( 4 – 7 ) from the genus Atractylodes . [ABSTRACT FROM AUTHOR]

The survival of insect herbivores on chemically defended plants may often depend on their ability to metabolize these defense compounds. However, only little knowledge is available on how insects actually process most plant defense compounds. We investigated the metabolism of salicinoids, a major group of phenolic glycosides in poplar and willow species, by a generalist herbivore, the gypsy moth ( Lymantria dispar ). Seven salicinoid metabolites identified in gypsy moth caterpillar feces were mostly conjugates with glucose, cysteine or glycine. Two of the glucosides were phosphorylated, a feature not previously reported for insect metabolites of plant defense compounds. The origins of these metabolites were traced to specific moieties of three major poplar salicinoids ingested, salicin, salicortin and tremulacin. Based on the observed metabolite patterns we were able to deduce the initial steps of salicinoid breakdown in L. dispar guts, which involves cleavage of ester bonds. The conjugated molecules were effectively eliminated within 24 h after ingestion. Some of the initial breakdown products (salicin and catechol) demonstrated negative effects on insect growth and survival in bioassays on artificial diets. Gypsy moth caterpillars with prior feeding experience on salicinoid-containing poplar foliage converted salicinoids to the identified metabolites more efficiently than caterpillars pre-fed an artificial diet. The majority of the metabolites we identified were also produced by other common poplar-feeding insects. The conversion of plant defenses like salicinoids to a variety of water-soluble sugar, phosphate and amino acid conjugates and their subsequent excretion fits the general detoxification strategy found in insect herbivores and other animals. [ABSTRACT FROM AUTHOR]

Two new phenolic glycosides, named gnaphaffine A and B (compounds 1 and 2), were isolated from Gnaphalium affine. together with six known compounds, including caffeic acid (3), everlastoside L (4), isorhamnetin-7-O-β-D-glucopyranoside (5), quercetin- 3-O-β-D-glucopyranoside (6), scutellarein-7-O-β-D-glucoside (7) and api-genin-7-O-β-D- glucopyranoside (8). Their structures were elucidated by spectroscopic methods, including ESI-MS and 2D NMR spectroscopy (HMQC and HMBC). All compounds were evaluated for their anti-complementary activity on the classical pathway of the complement system in vitro.

From the aerial parts, pericarps and roots of Solenostemma argel, three new pregnane glycosides (1-3) with two known ones and a new phenolic glycoside (4) have been isolated. Their structures were established by extensive 1D - and 2D NMR and mass spectroscopic analysis. The cytotoxicity of all compounds was evaluated against two human tumor cell lines (SW 480, MCF-7), but none of them was active in the concentration range 0.9-59.0 μM. Compounds 2 and the known argeloside F at non toxic concentrations for the PBMCs (27.3 μM and 27.6 μM, respectively) significantly decreased the Il-1β production by LPS-stimulated PBMCs. All isolated compounds showed a significant antioxidant potential with ORAC values in the concentration range 3481-9617 μmol eq. Trolox/100 g. [ABSTRACT FROM AUTHOR]

Cucurbitaceae are one of most widely used plant species for human food but lesser known members have not been examined for bioactive components. The purpose of this study was to evaluate the antioxidant and genoprotective activities from three cucurbitaceae seeds extracts and to identify phenolic components by LC–ESIMS/MS analysis. From the results, the yield of seeds extract was 20–41% (w/w) and samples had 16–40% total phenols as gallic acid equivalents (GAE). Compared with methanol solvent, using acidified methanol led to increased extraction yield by 1.4 to 10-fold, higher phenolic content (149.5 ± 1.2 to 396.4 ± 1.9 mg GAE/g), higher DPPH radical quenching and enhanced genoprotective activity using the pBR322 plasmid assay. LC–ESI-MS/MS analysis led to identification of 14–17 components, based on authentic standards and comparison with literature reports, as mainly phenolic acids and esters, flavonol glycosides. This may be the first mass spectrometric profiling of polyphenol components from cucurbitaceae seeds. [ABSTRACT FROM AUTHOR]

Overbrowsing by ungulates is a major cause of poor aspen stand regeneration across North America and Eurasia. In general, factors driving ungulate browser preferences include concentrations of plant secondary compounds and the nutritional composition (non-structural carbohydrates, protein and minerals) of foliage. While each of these phytochemical factors has been shown to independently influence ungulate preference, the relative impact of each factor is unknown, as no study to date has examined them simultaneously., Plant fitness depends not only on the capacity of plants to resist browsing, but also on their capacity to tolerate browsing once it has occurred. Little is known of aspen tolerance to browsing, which inflicts a different form of damage than insect herbivory., We employed multiple aspen genotypes, replicate trees of which were subjected to different soil nutrient treatments, to investigate: (i) the effects of aspen genotype, nutrient treatment and genotype × nutrient interactions on susceptibility to browsing by white-tailed deer, (ii) the phytochemical basis for the patterns observed in (i), and (iii) the effects of genotype, soil nutrients and their interaction on short-term tolerance to deer browsing., Aspen genotypes varied markedly in their vernal susceptibility to deer browsing. Genetic variation in early season levels of non-structural carbohydrates (sugars), protein and multiple macro- and trace minerals had the strongest influence on tree susceptibility to browsing. In contrast, levels of phytochemical defences had minimal effects, although the range of levels expressed in this study was small. Soil nutrient availability did not significantly influence deer preference., The extent of browsing affected post-browse tolerance across genotypes. Soil nutrient treatment had little differential effect on tolerance, and, for the most part, genotypes did not display differential tolerance to browsing, regardless of which soil nutrient treatment they experienced., Synthesis. Genetic variation for susceptibility to browsing indicates that ungulate browsers have the potential to be agents of selection in aspen populations. In contrast with previous studies in aspen highlighting the importance of phytochemical defences in shaping preferences of browsing mammals, our results indicate that the nutritional composition of foliage (sugars, protein and mineral concentrations) can have sizable effects on preference. The observed lack of influence of soil nutrient availability on tree browsing tolerance contrasts with predictions of the limiting resource model, the prevailing model for plant tolerance. [ABSTRACT FROM AUTHOR]

Plant- and insect-associated microorganisms encounter a diversity of allelochemicals, and require mechanisms for contending with these often deleterious and broadly-acting compounds. Trembling aspen, Populus tremuloides, contains two principal groups of defenses, phenolic glycosides (salicinoids) and condensed tannins, which differentially affect the folivorous gypsy moth, Lymantria dispar, and its gut symbionts. The bacteria genus Acinetobacter is frequently associated with both aspen foliage and gypsy moth consuming that tissue, and one isolate, Acinetobacter sp. R7-1, previously has been shown to metabolize phenolic glycosides. In this study, we aimed to characterize further interactions between this Acinetobacter isolate and aspen secondary metabolites. We assessed bacterial carbon utilization and growth in response to different concentrations of phenolic glycosides and condensed tannins. We also tested if enzyme inhibitors reduce bacterial growth and catabolism of phenolic glycosides. Acinetobacter sp. R7-1 utilized condensed tannins but not phenolic glycosides or glucose as carbon sources. Growth in nutrient-rich medium was increased by condensed tannins, but reduced by phenolic glycosides. Addition of the P450 enzyme inhibitor piperonyl butoxide increased the effects of phenolic glycosides on Acinetobacter sp. R7-1. In contrast, the esterase inhibitor S,S,S,-tributyl-phosphorotrithioate did not affect phenolic glycoside inhibition of bacterial growth. Degradation of phenolic glycosides by Acinetobacter sp. R7-1 appears to alleviate the cytotoxicity of these compounds, rather than provide an energy source. Our results further suggest this bacterium utilizes additional, complementary mechanisms to degrade antimicrobial phytochemicals. Collectively, these results provide insight into mechanisms by which microorganisms contend with their environment within the context of plant-herbivore interactions. [ABSTRACT FROM AUTHOR]

Three new alkaloids, liparis alkaloid A ( 1 ), B ( 2 ), C ( 3 ), and three new phenolic glycosides, liparis glycoside H ( 4 ), I ( 5 ), J ( 6 ), together with three known phenolic glycosides ( 7–9 ) were isolated from the whole plant of Liparis odorata . Their structures were characterized on the basis of extensive 1D-, 2D-NMR and HR-ESI-MS experiments. In addition, compounds 1 – 3 revealed hypolipidemic effects in the in vitro bioassays, and the ability to inhibit LPS-induced NO production of these isolated phenolic glycosides ( 4 – 9 ) was also evaluated. [ABSTRACT FROM AUTHOR]

In recent years, the exposure of vineyards and grapes to smoke from bushfires and controlled burn events has in some instances resulted in wines described as smoke tainted. Such wines are characterised by undesirable sensory characters described as smoky, burnt, ash, smoky bacon, medicinal and ashtray. This review summarises the knowledge about the composition of smoke from forest and grass fires, describes relationships between smoke exposure of vineyards and smoke taint in wine, and outlines strategies for managing and reducing the risk to producing smoke-affected wines. The sensitivity of grapes and vines at different phenological stages to the uptake of contaminants from smoke, especially smoke-derived volatile phenols, is outlined, and the pathways for entry and metabolic transformation of volatile phenols are discussed. The potential for translocation of phenolic contaminants within the grapevine and the differences in uptake of smoke contaminants of different grape cultivars are also discussed, along with preliminary work on dose/response relationships regarding concentration and duration of exposure and subsequent expression of smoke taint in wine. The chemical basis of smoke taint in wine is described, and the relationship between volatile phenols from combustion of wood/lignin and their glycosides, and sensory panel ratings of smoke attributes in affected wines is discussed. This includes a summary of sensory reconstitution studies and measurement of flavour compounds released from nonvolatile glycosides in mouth and during in vitro model experiments, which corroborate the sensory contribution of glycosylated phenolic substances and their role as flavour precursors. Finally, the review also discusses analytical methods used to quantify free volatile phenolic substances and their associated glycosides, biomarkers for identifying smoke exposure of grapes, and strategies for assessing the risk of quality loss post-smoke exposure. Case studies are presented that outline the influence of harvesting and winemaking practices on the expression of smoke taint, and that describe oenological approaches to ameliorate smoke taint in wine. [ABSTRACT FROM AUTHOR]

Aim This work was conducted to produce, purify and characterize biosurfactants from Aspergillus flavus AF612 isolated from citrus fruit. Methods and results Biosurfactant named 'Uzmaq' was isolated from A. flavus AF612. The chemical characterization of the biosurfactant was conducted. Biosurfactant Uzmaq produced by A. flavus, was composed of methoxy phenyl oxime glycosides. Two molecular forms of the biosurfactant, Uzmaq-A and Uzmaq-B were isolated. Biological properties (antifungal activity) were evaluated. The fractions of the biosurfactant were isolated and their surface properties were analysed. Uzmaq-A and Uzmaq-B had critical micelle concentration (CMC) around 170 and 80 mg l−1, and lowered surface tension of water up to 20 and 25 m Nm−1 respectively. The biosurfactants were stable at pH 3-12 and temperature up to 80°C. Growth and biosurfactant production kinetics were also analysed. Conclusion Novel biosurfactant Uzmaq was produced from A. flavus, which was composed of methoxy phenyl oxime glycosides. The surface activity of Uzmaq was better than the maximum values of synthetic chemical surfactants. The biosurfactant showed antifungal activity and self-assembling properties. Significance and Impact of the Study Aspergillus flavus AF612 can be used for commercial production of Uzmaq that may be employed for controlled drug release applications and bioremediation. [ABSTRACT FROM AUTHOR]

Paulownia tomentosa, a member of the plant family Paulowniaceae and a rich source of biologically active secondary metabolites, is traditionally used in Chinese herbal medicine. Flavonoids, lignans, phenolic glycosides, quinones, terpenoids, glycerides, phenolic acids, and miscellaneous other compounds have been isolated from different parts of P. tomentosa plant. Recent interest in this species has focused on isolating and identifying of prenylated flavonoids, that exhibit potent antioxidant, antibacterial, and antiphlogistic activities and inhibit severe acute respiratory syndrome coronavirus papain-like protease. They show cytotoxic activity against various human cancer cell lines and inhibit the effects of human cholinesterase, butyrylcholinesterase, and bacterial neuraminidases. Most of the compounds considered here have never been isolated from any other species of plant. This review summarizes the information about the isolated compounds that are active, their bioactivities, and the structure-activity relationships that have been worked out for them. [ABSTRACT FROM AUTHOR]

The EtOH extract of the roots ofPaeonia lactifloraafforded a new phenolic glycoside paenoside A (1) and a new monoterpene glycoside paeonin D (2), and five known monoterpene glycosides. Their structures were elucidated on the basis of spectroscopic means and hydrolysis products. All compounds displayed inhibitory potential against enzyme lipoxygenase. [ABSTRACT FROM PUBLISHER]

Regularities of spectrophotometric determination of phenolic compounds in medicinal plant raw materials are considered taking into account the effect of coexisting compounds. An algorithm for the development of a spectrophotometric procedure of analysis of biologically active compounds in medicinal plant raw materials and related pharmaceutical formulations was composed on the basis of generalized results of author´s own studies and literature data. [ABSTRACT FROM AUTHOR]

The root of Rhodiola imbricata , a Trans Himalayan food crop is known for its antioxidant and adaptogenic properties. Four new compounds ( 7 , 11 , 12 and 15 ) together with known phenolic glycosides ( 10 , 13 – 14 , 16 – 19 ) and other phenolics ( 1 – 6 , 8 – 9 ) were isolated from the ethyl acetate extract of the roots of R. imbricata . The structures of isolated molecules were established by spectroscopic techniques (ESI-HRMS, 1D and 2D NMR) and chemical methods. The compounds were evaluated for their antioxidant (radical scavenging, MTT antioxidant, linoleic acid peroxidation and reducing power assay) and anticancer activities against A-549 and MCF-7 cancer cell lines. [ABSTRACT FROM AUTHOR]

Phytochemical investigation of a Chinese fern Lepidogrammitis drymoglossoides led to the isolation of five compounds, including one triterpenoid, two lignans and two glycosides. Their structures were determined to be filic-3-ene-28-oic acid (1), (−)-syringaresinol-4 -O- beta- d -glucopyranoside (2), lyoniresinol (3), 4- O- beta- d -glucopyranosyl caffeic acid (4) and n -butyl- O- beta- d -fructopyranoside (5) on the basis of mass and NMR spectra and chemical and physical properties. Filic-3-ene-28-oic acid (1) is a new triterpenoid, while compounds 2–5 were isolated from the genus Lepidogrammitis for the first time. Chemotaxonomic significance of this investigation is summarized. [ABSTRACT FROM AUTHOR]

Five new phenolic glycosides, Sargentodosides A-E, and two new dihydronaphthalene lignans, Sargentodognans F-G, together with thirty-two known phenolic compounds were isolated from the 60% ethanol extracts of Sargentodoxa cuneata . Their structures including absolute configurations were determined by spectroscopic analysis and electronic circular dichroism experiments. In bioscreening experiments, twelve compounds ( 22 – 26 , 29 , 33 – 34 , 36 , 38 ) exhibited antibacterial activities against S. aureus ATCC 29213 with minimum inhibitory concentration (MIC) values of 2–516 μ g/mL. And compound 29 showed the highest antibacterial activity against S. aureus ATCC 29213 with MIC values of 2 μ g/mL, while the MIC values of levofloxacin was 8 μ g/mL. Three compounds ( 29 , 33 , 36 ) exhibited antibacterial activities against S. aureus ATCC 25923 with MIC values of 256–516 μ g/mL. Two compounds ( 29 , 33 ) exhibited antibacterial activities against A. baumanii ATCC 19606 with MIC values of 128–516 μ g/mL. However, no compound exhibited antimicrobial activities against C. albicans ATCC 10231. Moreover, three compounds ( 10 , 25 , 36 ) exhibited significant inhibition of proliferation in the two cell lines Hela and Siha, and showed stronger inhibitive activity of these two selected cell lines than cisplatin in the cytotoxic assay. Thus, S. cuneata is a potential plant source for further research targeting bacteria and cancer diseases. [ABSTRACT FROM AUTHOR]

A phytochemical investigation from 80% ethanol extract of Penthorum chinense Pursh (Saxifragaceae) resulted in the isolation of three new phenolic glycosides ( 1 – 3 ), together with three known phenolic glycosides ( 4 – 6 ). The structures of the new compounds were deduced from their comprehensive spectroscopic analysis including IR, HR-EI-MS, 1 H NMR, 13 C NMR, DEPT, COSY, HMBC and HMQC. And the structures of known compounds 4 – 6 were identified by comparison of their spectral data with those reported in the literature. [ABSTRACT FROM AUTHOR]

Microbial symbionts are becoming increasingly recognized as mediators of many aspects of plant - herbivore interactions. However, the influence of plant chemical defenses on gut associates of insect herbivores is less well understood. We used gypsy moth ( Lymantria dispar L.), and differing trembling aspen ( Populus tremuloides Michx.) genotypes that vary in chemical defenses, to assess the influence of foliar chemistry on bacterial communities of larval midguts. We evaluated the bacterial community composition of foliage, and of midguts of larvae feeding on those leaves, using next-generation high-throughput sequencing. Plant defense chemicals did not influence the composition of foliar communities. In contrast, both phenolic glycosides and condensed tannins affected the bacterial consortia of gypsy moth midguts. The two most abundant operational taxonomic units were classified as Ralstonia and Acinetobacter. The relative abundance of Ralstonia was higher in midguts than in foliage when phenolic glycoside concentrations were low, but lower in midguts when phenolic glycosides were high. In contrast, the relative abundance of Ralstonia was lower in midguts than in foliage when condensed tannin concentrations were low, but higher in midguts when condensed tannins were high. Acinetobacter showed a different relationship with host chemistry, being relatively more abundant in midguts than with foliage when condensed tannin concentrations were low, but lower in midguts when condensed tannins were high. Acinetobacter tended to have a greater relative abundance in midguts of insects feeding on genotypes with high phenolic glycoside concentrations. These results show that plant defense chemicals influence herbivore midgut communities, which may in turn influence host utilization. [ABSTRACT FROM AUTHOR]

Four new phenolic glycosides, liparisglycosides D-G ( 1- 4), together with a known compound ( 5) were isolated from the whole plant of Liparis odorata. Their structures were elucidated through extensive spectroscopic methods, including UV, IR, MS, 1D, and 2D NMR experiments (HSQC, COSY, and HMBC), and in an in vitro bioassay, compounds 1, 3, and 5 showed moderate inhibitory effects on nitric oxide production in LPS-induced microglia cells at 10 µM, yet all compounds were inactive when tested against five human cancer cell lines (IC >10 µM). [ABSTRACT FROM AUTHOR]

Three new phenolic glycosides, named as glycopentosides A–C (1–3), along with nine known compounds were isolated from the n-BuOH extract of stems of Glycosmis pentaphylla. Their structures were determined by using spectroscopic and chemical methods. Bioassay showed that compound 10 (tachioside) could inhibit nitric oxide production in lipopolysaccharides-stimulated RAW 264.7 cells with IC50 value of 12.14 μM. [ABSTRACT FROM AUTHOR]

The phytochemical investigation of the stems of Dendrobium officinale Kimura et Migo led to the isolation of a new chromone, chromcinale (1) and a new phenolic glycoside, leonuriside C (5), together with three known biogenetically related phenanthrenes (2 – 4), three known biogenetically related phenolic glycosides (6 – 8) and four known biogenetically related phenylpropanoids (9 – 12). The structures of these compounds were elucidated using comprehensive spectroscopic methods. Compounds 1–3 , 5–12 were isolated from the D. officinale for the first time. The chemotaxonomic significance of the isolates was also discussed. [Display omitted] • A new chromone, chromcinale and a new phenolic glycoside, leonuriside C from the Dendrobium officinale. • Compounds 1–3 , 5–12 were isolated from the Dendrobium officinale for the first time. • Compounds 1 - 12 may have a role as chemotaxonomic markers for Dendrobium officinale. [ABSTRACT FROM AUTHOR]

Aspen ( Populus tremuloides Michx.) has evolved a chemical defense system comprised of phenolic glycosides (PG), which effectively deter insect herbivory. However, much less is known about the role of PG and the nutritional quality of the associated plant community on aspen browse susceptibility to mammalian herbivores. In three successive periods during the growing season, we conducted experiments with sheep by offering leaves from two aspen stands with different concentrations of PG (LOW, HIGH) or aspen leaves vs. leaves from a forb (Utah pea, Lathyrus pauciflorus) or a grass (smooth brome, Bromus inermis Leyss.) growing in an aspen understory. Intake of aspen (19 to 35 % PG) was low in all periods (1 to 6 g/Kg in 2 hr) supporting the notion that aspen's defense system may contribute to its ecological success. However, lambs ate larger amounts of LOW than of HIGH suggesting that sheep could discriminate between aspen stands with different concentrations of PG, even when both stands were relatively well defended. Concentration of nutrients and chemical defenses in aspen leaves remained fairly stable across the growing season, and preference for aspen increased over the growing season. In contrast, preference for the forb and the grass decreased across the growing season in concert with a decline in the nutritional quality of these plants. The data suggest that nutritional context of aspen and associated forage species drove preference more than contrasts in defense chemistry of aspen. There may be periods of 'susceptibility' of aspen use by mammalian herbivores, despite high concentrations of chemical defenses, which can potentially be targeted by management to reduce aspen herbivory. [ABSTRACT FROM AUTHOR]

Phytophagous insects must contend with numerous secondary defense compounds that can adversely affect their growth and development. The gypsy moth ( Lymantria dispar) is a polyphagous herbivore that encounters an extensive range of hosts and chemicals. We used this folivore and a primary component of aspen chemical defenses, namely, phenolic glycosides, to investigate if bacteria detoxify phytochemicals and benefit larvae. We conducted insect bioassays using bacteria enriched from environmental samples, analyses of the microbial community in the midguts of bioassay larvae, and in vitro phenolic glycoside metabolism assays. Inoculation with bacteria enhanced larval growth in the presence, but not absence, of phenolic glycosides in the artificial diet. This effect of bacteria on growth was observed only in larvae administered bacteria from aspen foliage. The resulting midgut community composition varied among the bacterial treatments. When phenolic glycosides were included in diet, the composition of midguts in larvae fed aspen bacteria was significantly altered. Phenolic glycosides increased population responses by bacteria that we found able to metabolize these compounds in liquid growth cultures. Several aspects of these results suggest that vectoring or pairwise symbiosis models are inadequate for understanding microbial mediation of plant-herbivore interactions in some systems. First, bacteria that most benefitted larvae were initially foliar residents, suggesting that toxin-degrading abilities of phyllosphere inhabitants indirectly benefit herbivores upon ingestion. Second, assays with single bacteria did not confer the benefits to larvae obtained with consortia, suggesting multi- and inter-microbial interactions are also involved. Our results show that bacteria mediate insect interactions with plant defenses but that these interactions are community specific and highly complex. [ABSTRACT FROM AUTHOR]

Five new phenolic glycosides, 2-hydroxy-(2′E)-prenyl benzoate-2,4′-di-O-β-d-glucopyranoside (1), 2-hydroxy-(2′E)-prenyl benzoate-2-O-α-l-arabinopyranosyl-(1 → 6)-β-d-glucopyranoside (2), 4-methylphenol-1-O-α-l-rhamnopyranosyl-(1 → 6)-β-d-glucopyranoside (3), 4-methylphenol-1-O-α-l-arabinopyranosyl-(1 → 6)-β-d-glucopyranoside (4), and 3,5-dimethoxyphenol-1-O-β-d-apiofuranosyl-(1 → 2)-β-d-glucopyranoside (5), together with six known glycosides (6–11), were isolated from then-BuOH fraction of the EtOH extract ofPilea cavalerieiLevl subsp.cavaleriei. Their structures were elucidated by extensive spectroscopic analysis, including 1D and 2D NMR spectroscopy as well as HR-ESI-MS, and chemical evidences. All these compounds were isolated from the genusPileafor the first time. [ABSTRACT FROM PUBLISHER]