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Chardonnay marc, a co-product of the winemaking industry, is a combination of skins, seeds, and stems remaining after the juice is pressed from the grapes. This co-product amounts to over half a million tons per year. Recently, Chardonnay marc has been emerging as a healthy and flavorful food ingredient. The aroma contribution of the seeds to the overall aroma of Chardonnay marc remains unknown. In the present study, 43 odorants were identified in Chardonnay seeds employing aroma extract dilution analysis (AEDA) performed on a distillate prepared by solvent extraction and solvent-assisted flavor evaporation (SAFE) distillation. Of those, 6 odorants with a flavor dilution (FD) factor ≥64 were quantitated using stable isotope dilution assays (SIDAs). The odorants included (2

Research continues to provide compelling insights into potential health benefits associated with diets rich in plant-based natural products (PBNPs). Coupled with evidence from dietary intervention trials, dietary recommendations increasingly include higher intakes of PBNPs. In addition to health benefits, PBNPs can drive flavor and sensory perceptions in foods and beverages. Chardonnay marc (pomace) is a byproduct of winemaking obtained after fruit pressing that has not undergone fermentation. Recent research has revealed that PBNP diversity within Chardonnay marc has potential relevance to human health and desirable sensory attributes in food and beverage products. This review explores the potential of Chardonnay marc as a valuable new PBNP ingredient in the food system by combining health, sensory, and environmental sustainability benefits that serves as a model for development of future ingredients within a sustainable circular bioeconomy. This includes a discussion on the potential role of computational methods, including artificial intelligence (AI), in accelerating research and development required to discover and commercialize this new source of PBNPs.

An activity-guided fractionation approach applied to thermally treated, enzymatically hydrolyzed mushroom, Agaricus bisporus L., protein led to the identification of several saltiness- and kokumi-enhancing peptides. The identification was accomplished by employing a combination of solid-phase extraction (SPE), gel-permeation chromatography (GPC), and semipreparative reverse-phase high-performance liquid chromatography (RP-HPLC), coupled with sensory analysis. As a result, this study led to the identification of a collection of common mushroom derived tastants, including 5'-mononucleotides and free amino acids, along with several taste-modulating pyroglutamyl dipeptides, including pyroglutamylcysteine (pGlu-Cys), pyroglutamylvaline (pGlu-Val), pyroglutamylaspartic acid (pGlu-Asp), pyroglutamylglutamic acid (pGlu-Glu), and pyroglutamylproline (pGlu-Pro). The taste-modulating thresholds for the pyroglutamyl dipeptides were calculated in a model mushroom broth containing natural concentrations of guanosine 5'-monophosphate and 14 amino acids, all with dose-over-threshold (DoT) factors ≥1. Liquid chromatography-tandem mass spectrometry (LC-MS/MS) was employed to quantitate the pyroglutamyl dipeptides, and their concentrations ranged from 2 to 58 μmol/L; however, they were determined to be present in the hydrolysate below their individual taste-modulating thresholds. Despite being present below their individual thresholds, when the dipeptides were collectively added to a model mushroom broth at their natural concentrations (143 μmol/L combined), both salty (p = 0.0061) and kokumi (p = 0.0025) taste attributes were significantly enhanced, demonstrating a synergistic subthreshold taste-modulating effect. This study lays the groundwork for future investigations on the saltiness-enhancing potential of mixtures of subthreshold levels of pyroglutamyl dipeptides found in mushrooms and other sources.

Understanding how host-associated microbial assemblages respond to pathogen invasion has implications for host health. Until recently, most investigations have focused on understanding the taxonomic composition of these assemblages. However, recent studies have suggested that microbial assemblage taxonomic composition is decoupled from its function, with assemblages being taxonomically varied but functionally constrained. The objective of this investigation was to understand how the Tri-colored bat, Perimyotis subflavus cutaneous microbial assemblage responds to fungal pathogen invasion within a functional context. We hypothesized that at a broad scale (e.g., KEGG pathways), there will be no difference in the functional assemblages between the white nose pathogen, Pseudogymnoascus destructans, positive and negative bats; and this pattern will be driven by the functional redundancy of bacterial taxa. At finer scales (e.g., gene models), we postulate differences in function attributed to interactions between bacteria and P. destructans, resulting in the production of antifungal metabolites. To test this, we used a combination of shotgun metagenomic and amplicon sequencing to characterize the bat cutaneous microbial assemblage in the presence/absence of P. destructans. Results showed that while there was a shift in taxonomic assemblage composition between P. destructans positive and negative bats, there was little overall difference in microbial function. Functional redundancy across bacterial taxa was clear at a broad-scale; however, both redundancy and variation in bacterial capability related to defense against pathogens was evident at finer scales. While functionality of the microbial assemblage was largely conserved in relation to P. destructans, the roles of particular functional pathways in resistance to fungal pathogens require further attention.

The American Matsutake, Tricholoma magnivelare (Peck) Redhead, is an edible wild mushroom with a distinctive aroma described as mushroom and spice with subtle floral and citrus nuances. In this study, a total of 36 odorants were identified from T. magnivelare using solvent-assisted flavor evaporation and aroma extract dilution analysis. Stable isotope dilution assays were performed to quantitate 14 odorants with flavor dilution factors ≥64. Odorants with high odor activity values (OAVs) included 1-octen-3-one (OAV 2125), linalool (OAV 650), (2E,4E)-nona-2,4-dienal (OAV 304), and 1-octen-3-ol (OAV 206). An odor simulation model matched the odor profile of the fresh mushroom. Omission studies showed that linalool, hexanal, (2E,4E)-nona-2,4-dienal, methyl (E)-3-phenylprop-2-enoate, and 1-octen-3-one or 1-octen-3-ol were essential to the aroma of T. magnivelare. Chiral chromatography showed that α-pinene was a scalemic mixture of 34% (R)-(+) to 66% (S)-(-), while 1-octen-3-ol was present as 95% (R)-(-) to 5% (S)-(+), and linalool was 96% (R)-(-) to 4% (S)-(+). These results establish the base for future investigations into the aroma chemistry of other members of the genus Tricholoma.

The fragrant bolete, Suillus punctipes (Peck) Singer, is an edible mushroom with a unique aroma reminiscent of mushroom and citrus peel with an undertone of apricot. Thirty-five odorants were identified using solvent-assisted flavor evaporation (SAFE) and aroma extract dilution analysis (AEDA). Fourteen odorants including those with flavor dilution (FD) factors ≥64 were quantitated using stable isotope dilution assays (SIDA). Some odorants with high OAVs included 1-octen-3-one (OAV 164368), 1-octen-3-ol (OAV 3421), linalool (OAV 812), and nonanal (OAV 487). An odor simulation model was prepared closely matching the aroma of the mushroom. Omissions experiments revealed that 1-octen-3-one, 1-octen-3-ol, (2E)-oct-2-enal, linalool, δ-dodecalactone, and a mixture of three aldehydes, octanal, nonanal, and decanal, were essential odorants for the aroma profile. Enantiomeric ratios were determined for several odorants employing chiral chromatography. The results from this study lay the groundwork for future studies in the aroma chemistry of S. punctipes and other mushrooms from the Suillus genus.

Employing isotope incubation studies, the biosynthetic pathway leading to a series of benzylic derivatives was elucidated in the fermentation broth of the edible mushroom Ischnoderma resinosum (P. ...

Thirty-five odorants from Meehan's mint, Meehania cordata, were identified using solvent-assisted flavor evaporation (SAFE) and aroma extract dilution analysis (AEDA). Twelve compounds with flavor dilution factors ≥16 were quantitated using stable isotope dilution assays (SIDA). Odor activity values (OAVs) and sensory experiments revealed (-)-(E)-pinocarvyl acetate as a key impact odorant contributing to the plant's unique woody and minty odor. Odor simulation experiments revealed a mixture of 10 compounds, including (2E,6Z)-nona-2,6-dienal (OAV 48000), β-ionone (OAV 33000), (E)-pinocarvyl acetate (OAV 8600), 1-octen-3-one (OAV 2800), and linalool (OAV 990), successfully mimicked the plant odor when combined in their natural concentrations. Three stereoisomers of pinocarvyl acetate were identified including (-)-(E)-, (+)-(E)-, and (-)-(Z)-isomers. The (E) to (Z)-ratio was determined as 95.5% (E) and 0.5% (Z). The enantiomeric ratio of (-)-(E)- to (+)-(E)- was determined as 96% (-)-(E)- and 4% (+)-(E)-pinocarvyl acetate. This study established the basis for future investigations aimed at determining the odorant variability of individual genotypes from natural populations of M. cordata and other members of the Meehenia genus.

Chardonnay marc, consisting of grape skins, seeds, and stems, is a coproduct of grape juice production for Chardonnay wine making. The discovery that marc contains a rich source of health-promoting molecules has led to its growing popularity as a flavorful healthy food ingredient. However, the odorants responsible for its pleasant fruity aroma remain unknown. In this study, 35 odorants were identified in Chardonnay marc skins using solvent-assisted flavor evaporation (SAFE) and aroma extract dilution analysis (AEDA). Thirteen odorants were quantitated employing stable isotope dilution assays (SIDAs), and odor activity values (OAVs) were calculated. Odorants with OAVs >1 included 3-methylnonane-2,4-dione (hay, OAV 5800), β-ionone (floral, violets, OAV 2900), (2E,4E)-nona-2,4-dienal (fatty, OAV 1200), β-damascenone (cooked apple, OAV 370), hexanal (green, OAV 260), oct-1-en-3-one (mushroom, OAV 200), linalool (floral, citrus, OAV 61), (2E,4E)-deca-2,4-dienal (fatty, OAV 60), 2-phenylethanol (floral, rose, OAV 16), 3-(methylsulfanyl)propanal (potato, OAV 3.7), HDMF (caramel, OAV 2.0), and ethyl octanoate (fruity, OAV 1.1). An odor simulation model prepared using odorants with OAVs >1 sensorially matched the aroma of the Chardonnay marc skins. This investigation establishes a foundation for future studies aimed at determining the contribution of individual Chardonnay marc components (skins, seeds, and stems) to the aroma profile of Chardonnay marc powder and aiding producers in delivering optimal and consistent aroma profiles by region.

Riesling wines are mostly enjoyed as young wines, usually consumed within the first few years after bottling. Throughout several years of aging, Riesling wines begin to develop more robust flavor profiles, often displaying less fruity and floral notes and more pronounced maple, honey, and caramel notes. A body of scientific literature has been conducted on the aroma chemistry of young Riesling wines; however, comparatively less scientific reports have been published on the aroma chemistry of aged Riesling wines, and a comprehensive aroma analysis of a 10-year-old Riesling wine has not been previously completed. In this study, a total of 36 odorants were identified in a 10-year-old aged Riesling wine using solvent-assisted flavor evaporation and aroma extract dilution analysis. A total of 26 odorants were quantitated by employing stable isotope dilution assays. Odorants with high odor activity values (OAV) included wine lactone (coconut, OAV 460), ethyl octanoate (fruity, OAV 240), ethyl hexanoate (fruity, OAV 97), s-damascenone (cooked apple, OAV 60), 5-ethyl-3-hydroxy-4-methyl-(5H)-furan-2-one (maple, OAV 33), (S)-ethyl 2-methylbutanoate (fruity, OAV 22), 3-(methylsulfanyl) propanal (cooked potato, OAV 20), ethyl 2-methylpropanoate (fruity, OAV 9.5), ethyl butanoate (fruity, 7.1 OAV), and 1,1,6-trimethyl-1,2-dihydronapthalene (petrol, OAV 6.4). An odor simulation model prepared from all the odorants with an OAV greater than 1 closely matched the sensory profile of the authentic wine. The results of this study provide insight about odorants present in a 10-year-old bottle aged Riesling wine, and this knowledge may be useful for future studies aimed at probing the influence of aging on the aroma chemistry of Riesling wines and other white wines.

Culinary sage (Salvia officinalis L.) is a common spice plant in the mint family (Lamiaceae) well known for its distinctive culinary and traditional medicinal uses. Sage tea has been used traditionally as a brain-enhancing tonic and extracts from sage have been reported to have both cognitive and memory enhancing effects. Brain-derived neurotrophic factor (BDNF) is an endogenous signaling molecule involved in cognition and memory function. In this study, activity-guided fractionation employing preparative reverse-phase high performance liquid chromatography (RP-HPLC) of culinary sage extracts led to the discovery of benzyl 6-O-β-D-apiofuranosyl-β-D-glucoside (B6AG) as a natural product that upregulates transcription of neurotrophic factors in C6 glioma cells. Purified B6AG showed a moderate dose response, with upregulation of BDNF and with EC50 at 6.46 μM. To better understand the natural variation in culinary sage, B6AG was quantitated in the leaves of several commercial varieties by liquid chromatography-mass spectrometry (LC-MS). The level of B6AG in dried culinary sage was found to range from 334 ± 14 to 698 ± 65 μg/g. This study provided a foundation for future investigations, including quantitative inquiries on the distribution of B6AG within the different plant organs, explorations in optimizing post-harvest practices, and aid in the development of sage varieties with elevated levels of B6AG.

Innovative approaches to develop flavors with high sensory appeal are critical in encouraging increased consumer preference and adoption of low sodium foods. Gas chromatography-olfactometry, coupled with stable isotope dilution assays and sensory experiments, led to the identification of the odorants responsible for an enhancement in saltiness perception of chicken broth prepared with thermally treated enzymatically hydrolyzed mushroom protein and cysteine, then reacted under kitchen-like cooking conditions. Comparative aroma extract dilution analysis revealed 36 odorants with flavor dilution factors between a range of 1 and 256. Sixteen odorants were quantitated and odor activity values (OAVs) calculated. Important odorants included 2-furfurylthiol (coffee, OAV 610), 1-(2-furyl)ethanethiol (meaty, OAV 78), 3-sulfanylpentan-2-one (catty, OAV 42), sotolon (maple, OAV 20), indole (animal, OAV 8), 2-methyl-3-(methyldithio)furan (meaty, OAV 3), and p-cresol (barnyard, OAV 1). An odor simulation model was evaluated in two consumer sensory studies. These studies confirmed that the addition of the aroma model increased the perceived saltiness of low sodium chicken broth (p < 0.05).

To identify fruit processing treatments relevant for functional food applications, beverages prepared from processed Garcinia xanthochymus fruits were investigated. Treatments, including air drying (AD), sun drying (SD), freeze drying (FD), high and low temperature blanching (BH and BL), and high and low sulfating (SH and SL) were evaluated for their effects on sensory quality, pH, color, free-radical scavenging activity (DPPH), and anti-inflammatory activity. Sensory analysis concluded that the BH treatment had an elevated tropical-note as compared to the SD treatment, whereas the highest pH, b* value and DPPH scavenging activities were recorded for FD, BL, and BH treatments, respectively. Activity-guided fractionation of fruit extracts led to the identification of 2,4,6,3′,4′-pentahydroxybenzophenone-2-O-s-D-glucopyranoside (1), showing an 80% reduction in IL-6 and a 31% reduction in nitric oxide (NO) levels. Quantitation of (1) revealed that FD followed by BH had the highest levels, at 24.9 mg/g and 2.3 mg/g, respectively. The results from this study demonstrated the potential of processed G. xanthochymus fruit as a functional beverage ingredient, with good sensory characteristics along with antioxidant and anti-inflammatory activities. This study examined the potential of processed G. xanthochymus fruit as the basis of a functional beverage.

Open in a separate window An activity-guided fractionation approach revealed several phenylpropanoid glycerol glucosides isolated from the bulbs of Lilium longiflorum Thunb. (Easter lily) with gluconeogenesis inhibitory activities. The strongest activity was observed for (2S)-1-O-p-coumaroyl-2-O-β-d-glucopyranosylglycerol (3), (2S)-1-O-caffeoyl-2-O-β-d-glucopyranosylglycerol (1), and (2R)-1-O-β-d-glucopyranosyl-2-O-p-coumaroylglycerol (2) with inhibitions of 51.2, 39.2, and 36.8%, respectively. The p-coumaroyl-based (3) and its acetylated derivative (5) exhibited differential inhibition activity (51.2% as compared to 3.6%), suggesting that natural acetylation decreases the hypoglycemic activity of these compounds. Direct structure–activity analysis of phenylpropanoid glycerol glucosides indicated that the hydroxylation pattern of the hydroxy cinnamic acid moiety and acetylation were responsible for the differences in activity. This is the first report of phenylpropanoid glycerol glucosides as a phytochemical class of hepatic glucose production inhibitors.

Eighteen odorants were identified by applying aroma extract dilution analysis in the liquid fermentation broth of the edible mushroom Ischnoderma resinosum (P. Karst). Eight compounds with flavor dilution factors ≥16 were quantitated in a 16-day sample using stable isotope dilution assays. Odor activity values (OAV) revealed anise-smelling 4-methoxybenzaldehyde (OAV; 1639), vanilla-smelling 3,4-dimethoxybenzaldehyde (OAV; 51), and cherry-smelling benzaldehyde (OAV; 14) as key contributors to the pleasant "candy-like" odor of the fermentation broth. Odor simulation experiments revealed a mixture of five compounds in their natural concentrations mimicked the odor of a 16-day-old fermentation broth. A 30-day time course study was conducted to monitor the production of three odorants in the fungal fermentation broth, where it was revealed that both 3,4-dimethoxybenzaldehyde (10.7 ± 1.0 mg/kg) and benzaldehyde (4.5 ± 0.1 mg/kg) peaked on day 16, whereas 4-methoxybenzaldehyde peaked on day 24 (104.9 ± 4.9 mg/kg).

Propolis is a fragrant material produced by bees and is commonly used as an ingredient in food, beverage, and consumer goods industries. Application of a comparative aroma extract dilution analysis (cAEDA) to volatiles isolated from propolis over three consecutive years afforded 48 odorants with flavor dilution (FD) factors ≥ 4, including 21 compounds not previously reported in propolis. Despite differences in FD factors of some compounds, the overall temporal variation in the odorants was low. Compounds with FD ≥ 64 were quantitated by stable isotope dilution assays (SIDAs), and odor activity values (OAVs) were calculated. A total of 22 compounds showed OAVs ≥ 1, including ( E)-isoeugenol (clove; OAV 3700), linalool (floral; OAV 380), butanoic acid (sweaty, rancid; OAV 370), and 3-phenylpropanoic acid (floral; OAV 270). An odor reconstitution model prepared from deodorized beeswax and the 22 odorants in their natural concentrations closely matched the olfactory profile of authentic propolis. The results of this study will help to establish a basis for future research on the variability of propolis sourced from different geographical locations, produced by different bee species, and collected from different botanical sources, all of which are largely unknown.

Bacillus strain UTK D1-0055 was isolated from a laboratory environment and appeared to have antilisterial activity. The genome was sequenced, the strain was identified as Bacillus altitudinis, and a high-quality complete annotated genome was produced. The taxonomy was evaluated for this and related Bacillus species (B. aerophilus, B. pumilus, B. safensis, B. stratosphericus, and B. xiamenensis) because the taxonomy is unclear and contains errors in public databases such as NCBI. The included strains grouped into seven clusters based on average nucleotide identity. Strains designated as B. aerophilus, B. altitudinis, and B. stratosphericus grouped together in the cluster containing the B. altitudinis type strain, suggesting that these three species should be considered a single species, B. altitudinis. The antimicrobial activity of UTK D1-0055 was evaluated against a panel of 15 Listeria strains (nine Listeria monocytogenes serotypes, Listeria innocua, and Listeria marthii), other foodborne pathogens (six Salmonella enterica serotypes and Escherichia coli), and three representative fungi (Saccharomyces cerevisiae, Botrytis cinerea, and Hyperdermium pulvinatum). Antibacterial activity was observed against all Listeria strains, but no antibacterial effects were found against the other tested bacterial and fungal strains. Biosynthetic gene clusters were identified in silico that may be related to the observed antibacterial activity, and these clusters included genes that putatively encode bacteriocins and nonribosomally synthesized peptides. The B. altitudinis strain identified in this investigation had a broad range of antilisterial activity, suggesting that it and other related strains may be useful for biocontrol in the food industry. HIGHLIGHTS

Authentic freshly distilled Tennessee whiskey is filtered through maple charcoal in a processing step known as the Lincoln County Process (LCP). Changes in odorants resulting from the LCP were characterized by a comparative aroma extract dilution analysis (cAEDA), quantitated by stable isotope dilution assays (SIDA), and odor activity values (OAVs) were calculated. Sensory evaluation showed a decrease in malty, rancid, fatty, and roasty aroma attributes of the distillate after LCP treatment. Forty-nine odorants were identified, nine of which have not been previously reported in the whiskey distillate literature. Thirty-one odorants were quantitated, all showing a decrease in concentration as a result of LCP treatment. Odorants, including (2E,4E)-nona-2,4-dienal (fatty), 3-methylbutanoic acid (rancid), 2'-aminoacetophenone (foxy), and 2-acetyl-1-pyrroline (roasty), dropped below detection thresholds (OAV 99%. The present investigation lays the groundwork for future studies aimed at flavor optimization for Tennessee whiskey production.

The American Matsutake

The fragrant bolete

The chemical compositions of by-products from commercial cannabidiol (CBD) extraction were characterized and quantitated by employing gas chromatography mass spectrometry (GC-MS) and GC flame-ionization detection (GC-FID). The four major by-products included an ethanol-wax suspension (WAX), terpenoid distillate (DIST-A), tar-like residue (TAR), and red resin (RES). The composition of WAX consisted of ∼28 wt % n-alkanes and ∼33-38 wt % cannabidiolic acid and CBD combined. The DIST-A consisted of ∼40 wt % sesquiterpenoids and ∼58 wt % cannabinoids. The DIST-A terpenoid profile was compared to dried unprocessed inflorescences (HEMP) to observe changes in monoterpene content after the distillation process. The TAR was composed of ∼5-9 wt % higher n-alkanes and up to 91 wt % cannabinoids, while RES consisted of up to 99 wt % cannabinoids. Several impurities including cannabidibutol and dehydroabietic acid were identified in commercial CBD samples. Compositional information of these by-products may provide manufacturers with the opportunity to optimize processing conditions.

Employing isotope incubation studies, the biosynthetic pathway leading to a series of benzylic derivatives was elucidated in the fermentation broth of the edible mushroom

Thirty-five odorants from Meehan's mint

Purpose: This study is to examine how viewing a Japanese garden affects Japanese patients with dementia. Background: In a previous study, authors explored the effect on individuals with Alzheimer’s disease of viewing an indoor Japanese garden at a nursing home in the United States and reported that viewing the garden significantly reduced the heart rate, evoked short-term and long-term memories, and improved behavioral symptoms. However, it was unclear whether these effects were caused by the design of Japanese garden or unfamiliarity of the design to Caucasians. Methods: We constructed a Japanese garden on the rooftop of a hospital in Japan and assessed with a total of 25 subjects on the following categories: (1) eye movement, (2) heart rate, and (3) behavior under four different conditions: (a) open view of the site before construction of the Japanese garden (the control space), (b) open view of the Japanese garden, (c) view of the Japanese garden through closed door, and (d) view of Japanese garden through closed door with the chrysanthemum scent. Findings/Results: Viewers’ eyes scanned larger area while viewing the Japanese garden, and viewing the Japanese garden significantly reduced heart rate and improved behavioral symptoms than the control space. We also found that the effect of viewing the same Japanese garden differed across three conditions: the view through an open door, a closed door, and a closed door with added scent.

Pycnanthemum incanum, a species of wild mountain mint endemic to North America, has a pungent mint-like odor that has not been fully characterized. Due in part to its high terpene content, P. incanum has broad potential for health-promoting, cosmetic, culinary, and food flavoring applications. Therefore, odorants of P. incanum were identified by coupling solvent assisted flavor evaporation (SAFE) and aroma extract dilution analysis (AEDA), which afforded 24 odorants including 14 odorants with flavor dilution (FD) factors ≥4. Selected odorants, including those with FD factors ≥16, were quantitated by stable isotope dilution assays (SIDAs), and odor activity values (OAVs) were determined. The odorants with the highest OAVs included β-ionone (floral, violet; OAV 300), myrcene (terpeny, OAV 120), linalool (floral, citrus; OAV 79), and pulegone (mint, medicinal; OAV 58). An odor-simulation model based on the quantitation closely matched the sensory attributes of the original P. incanum plant material. In addition, enantiomeric proportions of chiral odorants in P. incanum were determined by chiral chromatography.

Thirty-four aroma-active compounds, previously identified with high flavor dilution factors by application of an aroma extract dilution analysis, were quantified in tree-ripened fruits of mango (Mangifera indica L. 'Haden'). From the results, the odor activity value (OAV) was calculated for each compound as the ratio of its concentration in the mangoes to its odor threshold in water. OAVs1 were obtained for 24 compounds, among which ethyl 2-methylbutanoate (fruity; OAV 2100), (3E,5Z)-undeca-1,3,5-triene (pineapple-like; OAV 1900), ethyl 3-methylbutanoate (fruity; OAV 1600), and ethyl butanoate (fruity; OAV 980) were the most potent, followed by (2E,6Z)-nona-2,6-dienal (cucumber-like), ethyl 2-methylpropanoate (fruity), (E)-β-damascenone (cooked apple-like), ethyl hexanoate (fruity), 4-hydroxy-2,5-dimethyl-3(2H)-furanone (caramel-like), 3-methylbut-2-ene-1-thiol (sulfurous), γ-decalactone (peach-like), β-myrcene (terpeny), (3Z)-hex-3-enal (green), 4-methyl-4-sulfanylpentan-2-one (tropical fruit-like), and ethyl octanoate (fruity). Aroma simulation and omission experiments revealed that these 15 compounds, when combined in a model mixture in their natural concentrations, were able to mimic the aroma of the fruits.

Ethnopharmacological relevance The bulbs and flowers of plants from the Lilium genus have historically been used in Asian and Greco-Roman medicine to treat burns and promote skin healing. Aim of the study To evaluate a steroidal glycoalkaloid isolated from Easter lily bulbs for its potential wound healing promoting properties. Materials and methods A lily-derived steroidal glycoalkaloid (LSGA), (22R, 25R)-spirosol-5-en-3β-yl O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-β-D-glucopyranoside, was isolated from Easter lily bulbs, and its structure was confirmed by LC-MS and NMR spectrometry. LSGA effects on wound scratch closure were evaluated in a primary human dermal fibroblast cell culture, and the changes in gene expression profiles were quantitated using an 84 wound-related gene qPCR microarray. Results LSGA promoted migration of dermal fibroblasts into the wounded area. The treatment was associated with a rapid upregulation of early inflammatory (CD40LG, CXCL11, IFNG, IL10, IL2 and IL4), cell growth (CSF3 and TNF) and remodeling (CTSG, F13A1, FGA, MMP and PLG) genes both in the wounded and unwounded cells treated with LSGA. A selective decrease in gene expression profiles associated with inflammatory (CXCL2 and CCL7) and remodeling (MMP7 and PLAT) phases was observed in wounded cells treated with LSGA, in contrast to the wounded cells (control). Conclusion This study demonstrates that a glycoalkaloid present in lilies promoted fibroblast migration in vitro and affected inflammatory, remodeling and growth factor gene expression. The decreases in expression of key genes may impact the wound healing process, possibly contributing to an earlier end of the inflammatory response and shortening the early phases of model tissue reconstitution. The results of this preliminary investigation may provide a basis for the historical use of lily bulbs to promote dermal healing after injury.

Ethnopharmacological relevance Preparations derived from bulbs of various Lilium species have been used to promote the healing of skin abrasions, sores and burns and to aid in healing wounds in Traditional Chinese and Greco-Roman Medicine. Aim of the study To evaluate fractionated Easter lily bulb extracts and their steroidal glycosides (1–5) for the promotion of dermal fibroblast migration in vitro , a model for the early events in wound healing. Materials and methods An activity-guided screening approach was used by coupling sequential solvent extraction, gel permeation chromatography (GPC), and semi-preparative reverse-phase high performance liquid chromatography (RP-HPLC) with an in vitro dermal fibroblast migration assay. Cytotoxicity was evaluated with methyl thiazole tetrazolium (MTT). To gain insight into the mode of action of the steroidal glycosides, nitric oxide (NO) production, and expression of genes for transforming growth factor beta-1 (TGF-β) and its receptors were evaluated. Results Fractionated bulb extracts and the two isolated steroidal glycoalkaloids ( 1 ) and ( 2 ) induced NO production and TGF-β receptor I mRNA expression in fibroblast cell culture. In a cytotoxicity assay, steroidal glycosides ( 1 ) and ( 3 ) had IC 50 values of 8.2 and 8.7 µM, but the natural acetylation of the C-6″′ hydroxy of the terminal glucose unit in ( 2 ) resulted in a 3-fold decrease in cell cytotoxicity when compared with ( 1 ). Results from the dermal fibroblast migration assay revealed that the steroidal glycoalkaloids ( 1 ) and ( 2 ), and the furostanol saponin ( 3 ) promoted fibroblast migration from the range of 23.7±5.7 to 37.7±5.1%, as compared with the control. Conclusion Collectively, our data demonstrate that the steroidal glycosides present in Easter lily bulbs induce, at least in part, the observed dermal fibroblast migration activity of the bulb extracts. This is the first evidence that steroidal glycosides from Lilium longiflorum may potentially play a role in the wound healing process and may provide a scientific basis for the historical use of lily bulbs for this purpose.

The bulbs of the Easter lily ( Lilium longiflorum Thunb.) are regularly consumed in Asia as both food and medicine, and the beautiful white flowers are appreciated worldwide as an attractive ornamental. The Easter lily is a rich source of steroidal glycosides, a group of compounds that may be responsible for some of the traditional medicinal uses of lilies. Since the appearance of recent reports on the role steroidal glycosides in animal and human health, there is increasing interest in the concentration of these natural products in plant-derived foods. A LC-MS/MS method performed in multiple reaction monitoring (MRM) mode was used for the quantitative analysis of two steroidal glycoalkaloids and three furostanol saponins, in the different organs of L. longiflorum. The highest concentrations of the total five steroidal glycosides were 12.02 ± 0.36, 10.09 ± 0.23, and 9.36 ± 0.27 mg/g dry weight in flower buds, lower stems, and leaves, respectively. The highest concentrations of the two steroidal glycoalkaloids were 8.49 ± 0.3, 6.91 ± 0.22, and 5.83 ± 0.15 mg/g dry weight in flower buds, leaves, and bulbs, respectively. In contrast, the highest concentrations of the three furostanol saponins were 4.87 ± 0.13, 4.37 ± 0.07, and 3.53 ± 0.06 mg/g dry weight in lower stems, fleshy roots, and flower buds, respectively. The steroidal glycoalkaloids were detected in higher concentrations as compared to the furostanol saponins in all of the plant organs except the roots. The ratio of the steroidal glycoalkaloids to furostanol saponins was higher in the plant organs exposed to light and decreased in proportion from the aboveground organs to the underground organs. Additionally, histological staining of bulb scales revealed differential furostanol accumulation in the basal plate, bulb scale epidermal cells, and vascular bundles, with little or no staining in the mesophyll of the bulb scale. An understanding of the distribution of steroidal glycosides in the different organs of L. longiflorum is the first step in developing insight into the role these compounds play in plant biology and chemical ecology and aids in the development of extraction and purification methodologies for food, health, and industrial applications. In the present study, (22R,25R)-spirosol-5-en-3β-yl O-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranosyl-(1→4)-β-d-glucopyranoside, (22R,25R)-spirosol-5-en-3β-yl O-α-l-rhamnopyranosyl-(1→2)-[6-O-acetyl-β-d-glucopyranosyl-(1→4)]-β-d-glucopyranoside, (25R)-26-O-(β-d-glucopyranosyl)furost-5-ene-3β,22α,26-triol 3-O-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranosyl-(1→4)-β-d-glucopyranoside, (25R)-26-O-(β-d-glucopyranosyl)furost-5-ene-3β,22α,26-triol 3-O-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranosyl-(1→3)-β-d-glucopyranoside, and (25R)-26-O-(β-d-glucopyranosyl)furost-5-ene-3β,22α,26-triol 3-O-α-l-rhamnopyranosyl-(1→2)-α-l-xylopyranosyl-(1→3)-β-d-glucopyranoside were quantified in the different organs of L. longiflorum for the first time.

The hepatoprotective activities of two different extracts, a hydroethanolic crude bulb extract (CB) and a steroidal glycoside-rich 1-butanol extract (BuOH), prepared from the bulbs of Easter lily (Lilium longiflorum Thunb.), were evaluated in a 24 week study in the female KK.Cg-A(y)/J Type 2 diabetic mouse model. Animals were divided into six groups (n = 16): control mice received Easter lily bulb extract-free drinking water together with a low- or high-fat diet (diabetic control); drinking water for the remaining groups was supplemented with CB extract (1%), BuOH extract (0.1 or 0.2%), and reference drug Metformin (0.001%), together with a high-fat diet. Both CB and BuOH extract treatment groups exhibited significantly improved liver function based on comparisons of triglycerides [diabetic 219 ± 34 mg/dL, CB 131 ± 27 mg/dL, BuOH(0.2%) 114 ± 35 mg/dL], CB total cholesterol (TC) (diabetic 196 ± 12 mg/dL, CB 159 ± 5 mg/dL), average liver mass [diabetic 2.96 ± 0.13 g, CB 2.58 ± 0.08 g, BuOH(0.1%) 2.48 ± 0.13 g], alanine transferase [diabetic 74 ± 5 units/L, CB 25 ± 1 units/L, BuOH(0.1%) 45 ± 1 units/L], and histological examinations. Glucose metabolism was improved only in CB, which was confirmed by oral glucose tolerance tests (OGTT) in diet-induced obese C57BL/6J mice exposed to CB extract. These data suggest that steroidal glycosides 1-5 might play a role in the hepatoprotective activity of the BuOH extracts, while the results of the TC measurements and OGTT study indicate that other constituents present in the CB extract are responsible for its hypocholesterolemic and hypoglycemic activity.

The Easter lily (Lilium longiflorum Thunb.) is esteemed worldwide as an attractive ornamental plant, and the flower buds and bulbs are used for both culinary and medicinal purposes in many parts of the world. L. longiflorum contains significant amounts of phenylpropanoid glycerol glucosides, a group of compounds that may contribute to plant pathogen defense, ultraviolet/high-intensity visible light (UV/high light) protection, and the purported medicinal uses of lilies. To define the natural distribution of these compounds within the plant, a liquid chromatography-mass spectrometry (LC-MS) method performed in selected ion monitoring (SIM) mode was employed for the quantitative analysis of five phenylpropanoid glycerol glucosides, namely, (2S)-1-O-caffeoyl-2-O-β-D-glucopyranosylglycerol, 1; (2R)-1-O-β-D-glucopyranosyl-2-O-p-coumaroylglycerol, 2; (2S)-1-O-p-coumaroyl-2-O-β-D-glucopyranosylglycerol, 3; (2S)-1-O-caffeoyl-2-O-β-D-glucopyranosyl-3-O-acetylglycerol, 4; and (2S)-1-O-p-coumaroyl-2-O-β-D-glucopyranosyl-3-O-acetylglycerol, 5, in the different organs of L. longiflorum. The p-coumaroyl-based 3 and its acetylated derivative 5 were determined to be the most abundant of the phenylpropanoid glycerol glucosides found in Easter lily bulbs, at 776.3 ± 8.4 and 650.7 ± 32.6 μg/g dry weight, respectively. The acetylated p-coumaroyl- and caffeoyl-based derivatives, 5 and 4, accumulated to the highest concentration in the closed flower buds, at 4925.2 ± 512.8 and 3216.8 ± 406.4 μg/g dry weight, respectively. Compound 4, followed by 5 and 1, proved to be the most abundant in the mature flowers, occurring at 6006.2 ± 625.8, 2160.3 ± 556.5, and 1535.8 ± 174.1 μg/g dry weight, respectively. Total concentrations of the phenylpropanoid glycerol glucosides were 10-100-fold higher in the above-ground plant organs as compared to the bulbs and fleshy roots. Two of the five compounds, 1 and 2, were identified in L. longiflorum for the first time. The quantitative analysis of phenylpropanoid glycerol glucosides in the different plant organs of L. longiflorum will establish the direction of investigations aimed at defining how these compounds function in the physiology and chemical ecology of the plant and also as a starting point for determining their possible effects on human health, which has not been investigated.

Covering: 1989 up to 2014 Plants from the Lilium genus are a rich source of chemical diversity and have been the focus of natural products chemistry research for over twenty years. This manuscript provides a background on the chemistry and nomenclature of steroidal glycosides, as well as a chronological account of the progress between the years of 1989 up to 2014, with respect to their isolation and characterization from the genus. This review highlights the traditional use of lilies, as both food and medicine, and brings attention to the fact that the genus contains 110 accepted species of which the chemistry and biological activity of the steroidal glycosides from the majority have not been investigated to date. Thus, making the genus a relatively untapped resource that contains a potential treasure trove of chemical diversity waiting to be discovered.

The aroma-active compounds present in tree-ripened fruits of the five mango (Mangifera indica L.) cultivars Haden, White Alfonso, Praya Sowoy, Royal Special, and Malindi were isolated by solvent extraction followed by solvent-assisted flavor evaporation (SAFE) and analyzed by gas chromatography-olfactometery (GC-O). Application of a comparative aroma extract dilution analysis (cAEDA) afforded 54 aroma-active compounds in the flavor dilution (FD) factor range from 4 to ≥2048, 16 of which are reported for the first time in mango. The results of the identification experiments in combination with the FD factors revealed 4-hydroxy-2,5-dimethyl-3(2H)-furanone as an important aroma compound in all cultivars analyzed. Twenty-seven aroma-active compounds were present in at least one mango cultivar at an FD factor ≥128. Clear differences in the FD factors of these odorants between each of the mango cultivars suggested that they contributed to the unique sensory profiles of the individual cultivars.

Botrytis cinerea Pers. Fr. is a plant pathogenic fungus and the causal organism of blossom blight of Easter lily (Lilium longiflorum Thunb.). Easter lily is a rich source of steroidal glycosides, compounds which may play a role in the plant-pathogen interaction of Easter lily. Five steroidal glycosides, including two steroidal glycoalkaloids and three furostanol saponins, were isolated from L. longiflorum and evaluated for fungal growth inhibition activity against B. cinerea, using an in vitro plate assay. All of the compounds showed fungal growth inhibition activity; however, the natural acetylation of C-6''' of the terminal glucose in the steroidal glycoalkaloid, (22R,25R)-spirosol-5-en-3β-yl O-α-L-rhamnopyranosyl-(1→2)-[6-O-acetyl-β-D-glucopyranosyl-(1→4)]-β-D-glucopyranoside (2), increased antifungal activity by inhibiting the rate of metabolism of the compound by B. cinerea. Acetylation of the glycoalkaloid may be a plant defense response to the evolution of detoxifying mechanisms by the pathogen. The biotransformation of the steroidal glycoalkaloids by B. cinerea led to the isolation and characterization of several fungal metabolites. The fungal metabolites that were generated in the model system were also identified in Easter lily tissues infected with the fungus by LC-MS. In addition, a steroidal glycoalkaloid, (22R,25R)-spirosol-5-en-3β-yl O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (6), was identified as both a fungal metabolite of the steroidal glycoalkaloids and as a natural product in L. longiflorum for the first time.

The bulbs of the Easter lily ( Lilium longiflorum Thunb.) are used as a food and medicine in several Asian cultures, and they are cultivated as an ornamental plant throughout the world. A new steroidal glycoalkaloid and two new furostanol saponins, along with two known steroidal glycosides, were isolated from the bulbs of L. longiflorum. The new steroidal glycoalkaloid was identified as (22R,25R)-spirosol-5-en-3beta-yl O-alpha-l-rhamnopyranosyl-(1--2)-[6-O-acetyl-beta-d-glucopyranosyl-(1--4)]-beta-d-glucopyranoside. The new furostanol saponins were identified as (25R)-26-O-(beta-d-glucopyranosyl)-furost-5-en-3beta,22alpha,26-triol 3-O-alpha-l-rhamnopyranosyl-(1--2)-alpha-l-arabinopyranosyl-(1--3)-beta-d-glucopyranoside and (25R)-26-O-(beta-d-glucopyranosyl)-furost-5-en-3beta,22alpha,26-triol 3-O-alpha-l-rhamnopyranosyl-(1--2)-alpha-l-xylopyranosyl-(1--3)-beta-d-glucopyranoside. The previously known steroidal glycosides, (22R,25R)-spirosol-5-en-3beta-yl O-alpha-l-rhamnopyranosyl-(1--2)-beta-d-glucopyranosyl-(1--4)-beta-d-glucopyranoside and (25R)-26-O-(beta-d-glucopyranosyl)-furost-5-en-3beta,22alpha,26-triol 3-O-alpha-l-rhamnopyranosyl-(1--2)-beta-d-glucopyranosyl-(1--4)-beta-d-glucopyranoside were identified in L. longiflorum for the first time. These new compounds from L. longiflorum and the isolation methodologies employed can be used for studies on the biological role of steroidal glycosides in plant development and plant-pathogen interactions, as well as for studies in food and human health, for which little is known.