Recent Developments in Therapeutic and Nutraceutical Applications of p-Methoxycinnamic Acid from Plant Origin.

The p-methoxycinnamic acid (p-MCA) is one of the most studied phenylpropanoids with high importance not only in the wide spectrum of therapeutic activities but also its potential application for the food industry. This natural compound derived from plants exhibits a wide range of biologically useful properties; therefore, during the last two decades it has been extensively tested for therapeutic and nutraceutical applications. This article presents the natural sources of p-MCA, its metabolism, pharmacokinetic properties, and safety of its application. The possibilities of using this dietary bioactive compound as a nutraceutical agent that may be used as functional food ingredient playing a vital role in the prevention and treatment of many chronic diseases is also discussed. We present the antidiabetic, anticancer, antimicrobial, hepato-, and neuroprotective activities of p-MCA and methods of its lipophilization that have been developed so far to increase its industrial application and bioavailability in the biological systems.

Six New Phenylpropanoid Derivatives from Chemically Converted Extract of Alpinia galanga (L.) and Their Antiparasitic Activities.

Chemical conversion of the extract of natural resources is a very attractive way to expand the chemical space to discover bioactive compounds. In order to search for new medicines to treat parasitic diseases that cause high morbidity and mortality in affected countries in the world, the ethyl acetate extract from the rhizome of Alpinia galanga (L.) has been chemically converted by epoxidation using dioxirane generated in situ. The biological activity of chemically converted extract (CCE) of A. galanga (L.) significantly increased the activity against Leishmania major up to 82.6 ± 6.2 % at 25 µg/mL (whereas 2.7 ± 0.8% for the original extract). By bioassay-guided fractionation, new phenylpropanoids (1-6) and four known compounds, hydroquinone (7), 4-hydroxy(4-hydroxyphenyl)methoxy)benzaldehyde (8), isocoumarin cis 4-hydroxymelein (9), and (2S,3S,6R,7R,9S,10S)-humulene triepoxide (10) were isolated from CCE. The structures of isolated compounds were determined by spectroscopic analyses of 1D and 2D NMR, IR, and MS spectra. The most active compound was hydroquinone (7) with IC50 = 0.37 ± 1.37 µg/mL as a substantial active principle of CCE. In addition, the new phenylpropanoid 2 (IC50 = 27.8 ± 0.34 µg/mL) also showed significant activity against L. major compared to the positive control miltefosine (IC50 = 7.47 ± 0.3 µg/mL). The activities of the isolated compounds were also evaluated against Plasmodium falciparum, Trypanosoma brucei gambisense and Trypanosoma brucei rhodeisense. Interestingly, compound 2 was selectively active against trypanosomes with potent activity. To the best of our knowledge, this is the first report on the bioactive "unnatural" natural products from the crude extract of A. galanga (L.) by chemical conversion and on its activities against causal pathogens of leishmaniasis, trypanosomiasis, and malaria.

Phenylpropanoid-conjugated pentacyclic triterpenoids from the whole plants of Leptopus lolonum induced cell apoptosis via MAPK and Akt pathways in human hepatocellular carcinoma cells.

Our present and previous phytochemical investigations on Leptopus lolonum have resulted in the isolation of almost 30 phenylpropanoid-conjugated pentacyclic triterpenoids (PCPTs). During the continuous study on PCPTs, this kind of triterpenoid ester is considered as a natural product with low toxicity because of it's widely distribution in natural plants and edible fruits including kiwi fruit, durian, jujube, pawpaw, apple and pear. In the present work, we report the isolation, structural elucidation and cytotoxic evaluation of four new PCPTs (1-4) which obtained from L. lolonum. In addition, the possible biosynthesis pathway for 28-norlupane triterpenoid and potent effect of phenylpropanoid moiety for increasing the cytotxic effect of triterpenoids were also discussed. Among these compounds, compound 1 exhibited the highest cytotoxic effect on HepG2 cells with IC50 value of 11.87 µM. Further flow cytometry and western blot analysis demonstrated that 1 caused G1 cell cycle arrest by up-regulated the expression of phosphorylated p53 protein in HepG2 cells and induced cell apoptosis via MAPK and Akt pathways. These results emphasized the potential of PCPTs as lead compounds for developing anti-cancer drugs.

Short communication: Short-term effect of 3-nitrooxypropanol on feed dry matter intake in lactating dairy cows.

The objective of this study was to investigate the effect of 3-nitrooxypropanol (3-NOP), an enteric methane inhibitor under investigation, on short-term dry matter intake (DMI) in lactating dairy cows. Following a 1-wk adaptation period, 12 multiparous Holstein cows were fed a basal total mixed ration (TMR) containing increasing levels of 3-NOP during 5 consecutive, 6-d periods. The experiment was conducted in a tiestall barn. Feed bins were split in half by a solid divider, and cows simultaneously received the basal TMR supplemented with the following: (1) a placebo without 3-NOP or (2) 3-NOP included in the TMR at 30, 60, 90, or 120 mg/kg of feed dry matter (experimental periods 2, 3, 4, and 5, respectively). Cows received the control diet (basal TMR plus placebo premix) during experimental period 1. A premix containing ground corn grain, soybean oil, and dry molasses was used to incorporate 3-NOP in the ration. Cows were fed twice daily as follows: 60% of the daily feed allowance at 0800 h and 40% at 1800 h. Feed offered and refused was recorded at each feeding. During the morning feedings, each cow was offered either control or 3-NOP-treated TMR at 150% of her average intake during the previous 3 d. After collection of the evening refusals, cows received only the basal TMR without the premix until the next morning feeding. The test period for the short-term DMI data collection was defined from morning feeding to afternoon refusals collection during each day of each experimental period. Location (left or right) of the control and 3-NOP diets within a feed bin was switched every day during each period to avoid feed location bias. Dry matter intake of TMR during the test period was quadratically increased by 3-NOP compared with the control. Inclusion of 3-NOP at 120 mg/kg of feed dry matter resulted in decreased 10-h DMI compared with the lower 3-NOP doses, but was similar to the control. There was no effect of feed location (left or right) within feed bin on DMI. Data from this short-term study suggests that 3-NOP does not have a negative effect on DMI in lactating dairy cows.

Isolation and Characterization of Phenylpropanoid and Lignan Compounds from Peperomia pellucida [L.] Kunth with Estrogenic Activities.

Extracts of Peperomia pellucida [L.] Kunth have previously been demonstrated to have in vivo estrogenic-like effects, thereby functioning as an anti-osteoporotic agent. However, the compounds responsible for these effects have not yet been determined. Therefore, the aim of this study is to isolate and elucidate potential compounds with estrogenic activity. The structures of the isolated compounds were identified using 1D 1H and 13C-NMR and confirmed by 2D FT-NMR. The estrogenic activity was evaluated using the E-SCREEN assay, and a molecular docking study was performed to predict the binding affinity of the isolated compounds to estrogen receptors. In this experiment, we successfully isolated three phenylpropanoids and two lignan derivatives, namely, 6-allyl-5-methoxy-1,3-benzodioxol-4-ol (1), pachypostaudin B (2), pellucidin A (3), dillapiole (4), and apiol (5). Among these compounds, the isolation of 1 and 2 from P. pellucida is reported for the first time in this study. Activity assays clearly showed that the ethyl acetate extract and its fractions, subfractions, and isolated compounds exerted estrogenic activity. Methanol fraction of the ethyl acetate extract produced the highest estrogenic activity, while 1 and 2 had partial agonist activity. Some compounds (derivates of dillapiole and pellucidin A) also had, in addition, anti-estrogenic activity. In the docking study, the estrogenic activities of 1-5 appeared to be mediated by a classical ligand-dependent mechanism as suggested by the binding interaction between the compounds and estrogen receptors; binding occurred on Arg 394 and His 524 of the alpha receptor and Arg 346 and His 475 of the beta receptor. In summary, we reveal that P. pellucida is a promising anti-osteoporotic agent due to its estrogenic activity, and the compounds responsible for this activity were found to be lignan and phenylpropanoid derivatives. The presence of other compounds in either the extract or fraction may contribute to a synergistic effect, as suggested by the higher estrogenic activity of the methanol fraction. Hence, we suggest further research on the osteoporotic activity and safety of the identified compounds, especially regarding their effects on estrogen-responsive organs.

3-Nitrooxypropanol supplementation had little effect on fiber degradation and microbial colonization of forage particles when evaluated using the in situ ruminal incubation technique.

3-Nitrooxypropanol (3-NOP) is an investigational compound that acts as an enzyme inhibitor to decrease ruminal methanogenesis. We hypothesized that when feeding 3-NOP to cattle fed a high-forage diet, H2 would accumulate in the rumen, which could suppress microbial colonization of feed particles and fiber degradation. Therefore, the study investigated the effects of supplementing a high-forage diet with 3-NOP on ruminal fiber degradability and microbial colonization of feed particles using the in situ technique. Eight ruminally cannulated beef cattle were allocated to 2 groups (4 cattle/group) in a crossover design with 2 periods and 2 dietary treatments. The treatments were control (basal diet) and 3-NOP (basal diet supplemented with 3-NOP, 150 mg/kg of dry matter). The basal diet consisted of 45% barley silage, 45% chopped grass hay, and 10% concentrate (dry matter basis). Samples of dried, ground barley silage and grass hay were incubated in the rumen of each animal for 0, 4, 12, 24, 36, 48, 96, 120, 216, and 288 h to determine neutral detergent fiber (NDF) degradation kinetics. An additional 2 bags were incubated for 4 and 48 h to evaluate the bacterial community attached to the incubated forages. Dietary supplementation of 3-NOP decreased (-53%) the dissolved methane concentration and increased (+780%) the dissolved H2 concentration in ruminal fluid, but did not substantially alter in situ NDF degradation. The addition of 3-NOP resulted in a decrease in the α-diversity of the microbial community with colonizing communities showing reduced numbers of amplicon sequence variants and phylogenetic diversity compared with control diets. Principal coordinate analysis plots indicated that forages incubated in animals fed 3-NOP resulted in highly specific changes to targeted microbes compared with control diets based on unweighted analysis (considering only absence and presence of taxa), but did not alter the overall composition of the colonizing community based on weighted UniFrac distances; unchanged relative abundances of major taxa included phyla Bacteroidetes, Firmicutes, and Fibrobacteres. The effect of 3-NOP on colonizing methanogenic microbes differed depending upon the forage incubated, as abundance of genus Methanobrevibacter was decreased for barley silage but not for grass hay. In conclusion, 3-NOP supplementation of a high-forage diet decreased ruminal methanogenesis and increased dissolved H2 concentration, but had no negative effects on ruminal fiber degradation and only minor effects on relative abundances of the major taxa of bacteria adhered to forage substrates incubated in the rumen.

Structure Elucidation of Two New Norlignans from Anemone vitifolia and Their Anti-Inflammatory Activities.

Two new norlignans together with two known phenylpropanoids were isolated from the whole herb of Anemone vitifolia. All compounds were reported from this plant for the first time. The structures of these compounds were identified by comprehensive HR-ESI-MS, 1D and 2D NMR spectroscopic data analysis and comparison with literature data. Additionally, bioactivity study results showed that two new compounds have potential anti-inflammatory activity. The plausible biosynthetic pathway for these compounds were also speculated in this article.

Identification of Cinnamaldehyde as Most Effective Fatty Acid Uptake Reducing Cinnamon-Derived Compound in Differentiated Caco-2 Cells Compared to Its Structural Analogues Cinnamyl Alcohol, Cinnamic Acid, and Cinnamyl Isobutyrate.

Naturally occurring cinnamon compounds such as cinnamaldehyde (CAL) and structurally related constituents have been associated with antiobesity activities, although studies regarding the impact on intestinal fatty acid uptake are scarce. Here, we demonstrate the effects of CAL and structural analogues cinnamyl alcohol (CALC), cinnamic acid (CAC), and cinnamyl isobutyrate on mechanisms regulating intestinal fatty acid uptake in differentiated Caco-2 cells. CAL, CALC, and CAC (3000 µM) were found to decrease fatty acid uptake by 58.0 ± 8.83, 19.4 ± 8.98, and 21.9 ± 6.55%, respectively. While CAL and CALC at a concentration of 300 µM increased serotonin release 14.9 ± 3.00- and 2.72 ± 0.69-fold, respectively, serotonin alone showed no effect on fatty acid uptake. However, CAL revealed transient receptor potential channel A1-dependency in the decrease of fatty acid uptake, as well as in CAL-induced serotonin release. Overall, CAL was identified as the most potent of the cinnamon constituents tested.

Effects of 3-nitrooxypropanol on enteric methane production, rumen fermentation, and feeding behavior in beef cattle fed a high-forage or high-grain diet1.

The objective of the study was to determine whether feeding a diet supplemented with 3-nitrooxypropanol (3-NOP) affects feeding behavior altering intake and rumen fermentation. Two experiments were conducted with 9 rumen-cannulated beef steers in a replicated 3 × 3 Latin square design where animals received a high-forage or high-grain diet. Treatments were 1) a basal diet (CON), the CON diet supplemented with 3-NOP (dNOP; 100 mg/kg in dietary DM or 1 g/d), or the CON diet with 3-NOP (1 g/d) infused into the rumen (infNOP). Each experimental period consisted of 14-d diet adaptation and 7-d sample collection. A 7-d washout period was provided between experiment periods. All data were analyzed as a Latin square design using Mixed Procedure of SAS. In Exp. 1 (high-forage diet), methane yield (measured by the Greenfeed system) was lowered by 18% (18.6 vs. 22.7 g/kg DMI; P < 0.01) by dNOP compared with CON. Rumen fermentation was altered similarly by both NOP treatments compared with CON where dNOP and infNOP increased (P < 0.01) rumen pH at 3 h and decreased (P < 0.01) proportion of acetate in total VFA. However, DMI, feed consumption rate (0 to 3, 3 to 6, 6 to 12, and 12 to 24 h after feeding), particle size distribution of orts, and feeding behavior (videotaped for individual animals over 48 h) were not affected by dNOP and infNOP compared with CON. In Exp. 2 (high-grain diet), methane production was not affected by dNOP or infNOP compared with CON. Dry matter intake, feed consumption rate, particle size distribution of orts, and feeding behavior were not altered by dNOP and infNOP compared with CON. However, both dNOP and infNOP affected rumen fermentation where total VFA decreased (P = 0.04) and acetate proportion in total VFA tended to decrease (P = 0.07) compared with CON. In conclusion, dietary supplementation of 3-NOP did not affect feeding behavior of beef steers fed a high-forage or high-grain diet. However, rumen fermentation was similarly changed when 3-NOP was provided in the diet or directly infused in the rumen. Thus, observed changes in rumen fermentation with 3-NOP were not due to changes in feeding behavior indicating no effects on the organoleptic property of the diets. In addition, according to small or no changes in DMI in both experiments and relatively small changes in rumen fermentation in Exp. 2, a greater dosage level of 3-NOP than 100 mg/kg (dietary DM) may need further examination of its effects on feeding behavior of beef cattle.

A Review: The Bioactivities and Pharmacological Applications of Phellinus linteus.

Phellinus linteus is a popular medicinal mushroom that is widely used in China, Korea, Japan, and other Asian countries. P. linteus comprises various bioactive components, such as polysaccharides, triterpenoids, phenylpropanoids, and furans, and has proven to be an effective therapeutic agent in traditional Chinese medicine for the treatment and the prevention of various diseases. A number of studies have reported that P. linteus possesses many biological activities useful for pharmacological applications, including anticancer, anti-inflammatory, immunomodulatory, antioxidative, and antifungal activities, as well as antidiabetic, hepatoprotective, and neuroprotective effects. This review article briefly presents the recent progress made in understanding the bioactive components, biological activities, pharmacological applications, safety, and prospects of P. linteus, and provides helpful references and promising directions for further studies of P. linteus.

Pharmacological Effects and Chemical Constituents of Bupleurum.

Radix Bupleuri has been used in traditional Chinese medicine for thousands of years, with confirmed curative effects. This plant is also used in healthy food and cosmetics. A recent increase in studies of Radix Bupleuri's chemical constituents (mainly comprising flavonoids, lignins, phenyl propanol derivatives, triterpenoid saponins, and volatile oils) and pharmacological effects motivates the aim of the present study: to review the chemical components and pharmacological effects of Radix Bupleuri. Our review found that Radix Bupleuri exhibits diverse pharmacological effects. More than 281 components have been isolated from Radix Bupleuri, including 15 flavonoids, 430 lignins, 12 phenyl propanol derivatives, 66 triterpenoid saponins, and 158 volatile oils.

Toxic and Repellent Effects of Volatile Phenylpropenes from Asarum heterotropoides on Lasioderma serricorne and Liposcelis bostrychophila.

Toxic and repellent effects of the essential oil from Asarum heterotropoides Fr. Schmidt var. mandshuricum (Maxim.) Kitag. were evaluated against Lasioderma serricorne and Liposcelis bostrychophila. The essential oils (EOs) from roots (ER) and leaves (EL) of A. heterotropoides were obtained separately by hydrodistillation and characterized by gas chromatography-mass spectrometry (GC-MS) analysis. Major components of ER and EL included methyleugenol, safrole, and 3,5-dimethoxytoluene. Both ER and EL of A. heterotropoides showed certain toxicity and repellency against L. serricorne and L. bostrychophila. 3,5-Dimethoxytoluene, methyleugenol, and safrole were strongly toxic via fumigation to L. serricorne (LC50 = 4.99, 10.82, and 18.93 mg/L air, respectively). Safrole and 3,5-dimethoxytoluene possessed significant fumigant toxicity against L. bostrychophila (LC50 = 0.83 and 0.91 mg/L air, respectively). The three compounds all exhibited potent contact toxicity against the two insect species. Here, the EL of A. heterotropoides was confirmed to have certain toxicity and repellency against stored product insects, providing a novel idea for the comprehensive use of plant resources.

E-p-Methoxycinnamoyl-α-l-rhamnopyranosyl Ester, a Phenylpropanoid Isolated from Scrophularia buergeriana, Increases Nuclear Factor Erythroid-Derived 2-Related Factor 2 Stability by Inhibiting Ubiquitination in Human Keratinocytes.

The nuclear factor erythroid-derived 2-related factor 2 (Nrf2) is a key regulator of gene expression during oxidative stress and drug detoxification. Thus, identifying Nrf2 activators to protect from possible cell damage is necessary. In this study, we investigated whether E-p-methoxycinnamoyl-α-l-rhamnopyranosyl ester (MCR), a phenylpropanoid isolated from Scrophularia buergeriana, can activate Nrf2 signaling in human keratinocytes (HaCaT). First, we determined the dose- and time-dependent effects of MCR on the expression and activity of Nrf2. The antioxidant response element-luciferase reporter assay and western blot analysis results showed that MCR markedly induced Nrf2 activity and its protein expression, respectively. Further, MCR increased both the mRNA and protein levels of heme-oxygenase-1, one of the Nrf2 target genes, in the cells. Interestingly, we found that Nrf2 stability was remarkably enhanced by MCR. Furthermore, ubiquitin-dependent proteasomal degradation of Nrf2 was significantly reduced by MCR. Thus, MCR might afford skin protection by enhancing Nrf2 stability or by blocking its proteasomal degradation.

Phenylpropanoids from the fruit of Crataegus pinnatifida exhibit cytotoxicity on hepatic carcinoma cells through apoptosis induction.

Eight new phenylpropanoids (1a/1b, 2-4, 5a/5b and 6) including two pairs of enantiomers (1a/1b and 5a/5b), along with a known analogue (7) were isolated from the fruit of Crataegus pinnatifida. Their structures were elucidated using comprehensive spectroscopic methods. Compounds 1a/1b and 5a/5b were separated successfully by chiral chromatographic column. The absolute configurations of enantiomers were determined by comparison between the experimental and calculated electronic circular dichroism (ECD) spectra. The in vitro antitumor activities of the isolates were evaluated against two human hepatocellular carcinoma HepG2 and Hep3B cells. Five compounds (1a/1b, 2-4) exhibited more potent cytotoxicity and their structure-activity relationships were also discussed. Annexin V-FITC/PI staining using flow cytometry was carried out to examine cell apoptosis, and the results showed that compounds 3-4 with the presence of two methoxy groups substituted at C-3' significantly induced apoptosis in HepG2 cells.

Rapid Communication: Evaluation of methane inhibitor 3-nitrooxypropanol and monensin in a high-grain diet using the rumen simulation technique (Rusitec).

The objective of this study was to evaluate the effects of 3-nitrooxypropanol (NOP), a known methane (CH) inhibitor; the ionophore monensin (MON); and their combination on in vitro CH production in a high-grain diet (85% barley grain, 10% barley silage, and 5% vitamin-mineral supplement; DM basis) using a rumen simulation technique (Rusitec). Sixteen fermentation vessels in 2 Rusitec apparatuses (blocks) were used in a completely randomized block design with 4 treatments: Control, NOP (200 µg/g DM), MON (200 µg/g DM), and the combination of 200 µg NOP/g DM and 200 µg MON/g DM (NOP + MON). Two fermenters within each apparatus were randomly assigned to a treatment. Treatments were mixed with 10 g of substrate and supplied on a daily basis. The study included an 8-d adaptation period without treatment supplementation and a 6-d period for addition of treatments. Dry matter disappearance, pH, and total VFA were not affected by treatment ( ≥ 0.34). Acetate proportion was decreased by 8.3% and 14.9% with NOP and NOP + MON ( < 0.01), respectively; however, propionate proportion was not affected by treatment ( = 0.44). The acetate to propionate ratio was lowered by 21.1% with the combination of NOP and MON ( = 0.02), whereas ammonia-N concentration was not affected by treatment ( = 0.50). Total gas production was unaffected ( = 0.50), but CH production decreased by 77.7% and 75.95% ( < 0.01) with NOP and NOP + MON addition, respectively. Concurrently, H gas production increased by 131.3% and 185.6% ( = 0.01) with NOP and NOP + MON treatments, respectively. The copy number of methanogens was decreased in both solid and liquid phases ( < 0.01) with NOP and NOP + MON treatments. Despite the combination of NOP + MON showing the greatest decrease in acetate molar proportion and acetate to propionate ratio, it did not further inhibit CH beyond the effect of NOP alone. The decrease in CH emissions with treatments that included NOP occurred along with a decrease in the copy number of methanogens associated with the solid and liquid phases, confirming the inhibitory effects of NOP on these microorganisms. In conclusion, the combined effects of NOP and MON on CH mitigation did not exceed the effect of NOP alone when using a high-grain diet in vitro.

Cinnamyl Alcohol, the Bioactive Component of Chestnut Flower Absolute, Inhibits Adipocyte Differentiation in 3T3-L1 Cells by Downregulating Adipogenic Transcription Factors.

The extract of chestnut (Castanea crenata var. dulcis) flower (CCDF) has antioxidant and antimelanogenic properties, but its anti-obesity properties have not been previously examined. In this study, we tested the effect of CCDF absolute on adipocyte differentiation by using 3T3-L1 cells and determining the bioactive component of CCDF absolute in 3T3-L1 cell differentiation. CCDF absolute (0.1-100[Formula: see text][Formula: see text]g/mL) did not change 3T3-L1 cell viability. At 50[Formula: see text][Formula: see text]g/mL and 100[Formula: see text][Formula: see text]g/mL, the absolute significantly reduced the accumulation of lipid droplets in 3T3-L1 cells that were induced by culture in medium containing 3-isobutyl-1-methylxanthine/dexamethasone/insulin (MDI). GC/MS analysis showed that CCDF absolute contains 10 compounds. Among these compounds, cinnamyl alcohol (3-phenyl-2-propene-1-ol) dose-dependently inhibited the increased accumulation of lipid droplets in MDI-contained medium-cultured 3T3-L1 cells at a concentration range of 0.1[Formula: see text][Formula: see text]g/mL to 10[Formula: see text][Formula: see text]g/mL that did not cause cytotoxicity in 3T3-L1 cells. The inhibitory effect was significant at 5[Formula: see text][Formula: see text]g/mL ([Formula: see text] of response in MDI alone-treated state, [Formula: see text]) and 10[Formula: see text][Formula: see text]g/mL ([Formula: see text] of response in MDI alone-treated state, [Formula: see text]). Moreover, the enhanced expression of obesity-related proteins (PPAR[Formula: see text], C/EBP[Formula: see text], SREBP-1c, and FAS) in MDI medium-cultivated 3T3-L1 cells was significantly attenuated by the addition of cinnamyl alcohol at 5[Formula: see text][Formula: see text]g/mL and 10[Formula: see text][Formula: see text]g/mL. These findings demonstrate that cinnamyl alcohol suppresses 3T3-L1 cell differentiation by inhibiting anti-adipogenesis-related proteins, and it may be a main bioactive component of CCDF absolute, exerting antidifferentiation action in 3T3-L1 cells. Therefore, cinnamyl alcohol, as well as CCDF absolute, may be potential candidates for the prevention or treatment of obesity.

Phenylpropanoids from the fruits of Nicandra physaloides and their anti-inflammatory activities.

Twenty-one phenylpropanoids, including 1 new (1) and 20 known phenylpropanoids (2-21), were isolated and identified from the fruits of Nicandra physaloides. The structures of these compounds were established by 1D and 2D NMR spectra referring to the literatures, together with mass spectrometry. It was found that the isolated compounds, except for 7, 18 and 19, showed the different levels of inhibitions on NO production by LPS-induced RAW 264.7 cells at IC50 values from 27.0 to 97.3 µM.

Phenylpropanoids from Juglans mandshurica exhibit cytotoxicities on liver cancer cell lines through apoptosis induction.

Three new phenylpropanoids (1-3) together with six known congeners (4-9) were isolated from the bark of Juglans mandshurica Maxim using anti-hepatoma activity as a guide. Their structures were determined by comprehensive NMR and HRESIMS spectroscopic data analyses. All the isolated compounds were evaluated for their growth inhibitory activities against two kinds of liver cancer cell lines (HepG2 and Hep3B). Among them, compound 4 showed moderate cytotoxic activities against HepG2 and Hep3B cell lines with IC50 values of 58.58 and 69.87µM. Compound 5 exhibited 50% cell death rate in HepG2 and Hep3B cell lines at 63.70 and 46.45µM, respectively. Further observation of morphological changes and Western blot demonstrated that compounds 4 and 5 exhibited their cytotoxic activities through the induction of apoptosis. A structure-activity relationship study suggested that an α, ß-unsaturated aldehyde might be the most important functional group.

Effects of sustained reduction of enteric methane emissions with dietary supplementation of 3-nitrooxypropanol on growth performance of growing and finishing beef cattle.

The study objective was to evaluate the effects of sustained reduction of enteric methane (CH) emissions with dietary supplementation of the inhibitor 3-nitrooxypropanol (NOP) on growth rate and feed conversion efficiency of growing and finishing beef cattle. Eighty-four crossbred steers were used in a 238-d feeding study and fed a backgrounding diet for the first 105 d (backgrounding phase) and transition diets for 28 d followed by a finishing diet for 105 d (finishing phase) with 3 doses of NOP (0, 100, and 200 mg/kg DM). The experiment was a completely randomized design using 21 pens (4 cattle/pen) with 7 pens per treatment. When cattle were fed the backgrounding diet, pen DMI was reduced ( < 0.01) whereas G:F tended to improve ( = 0.06) with increasing dose of NOP supplementation. During the finishing phase, DMI ( = 0.06) and ADG ( = 0.07) tended to decrease with increasing dose of NOP supplementation. Although both levels of NOP were effective in reducing CH emissions from the backgrounding diet ( < 0.01), only NOP supplemented at the highest dose was effective in reducing total CH emissions from the finishing diet ( < 0.01). Methane yield (g/kg DMI) was reduced whereas hydrogen emissions were increased at the highest dose of NOP supplementation with both backgrounding and finishing diets ( < 0.01). Overall, these results demonstrate efficacy of NOP in reducing enteric CH emissions from cattle fed backgrounding and finishing diets, and these effects were negated once NOP supplementation was discontinued.

Sustained reduction in methane production from long-term addition of 3-nitrooxypropanol to a beef cattle diet.

The objective was to evaluate whether long-term addition of 3-nitrooxypropanol (NOP) to a beef cattle diet results in a sustained reduction in enteric CH4 emissions in beef cattle. Eight ruminally cannulated heifers (637 ± 16.2 kg BW) were used in a completely randomized design with 2 treatments: Control (0 g/d of NOP) and NOP (2 g/d of NOP). Treatments were mixed by hand into the total mixed ration (60% forage, DM basis) at feeding time. Feed offered was restricted to 65% of ad libitum DMI (slightly over maintenance energy intake) and provided once per day. The duration of the experiment was 146 d, including an initial 18-d covariate period without NOP use; a 112-d treatment period with NOP addition to the diet, divided into four 28-d time intervals (d 1 to 28, 29 to 56, 57 to 84, and 85 to 112); and a final 16-d recovery period without NOP use. During the covariate period and at the end of each interval and the end of the recovery period, CH4 was measured for 3 d using whole animal metabolic chambers. The concentration of VFA was measured in rumen fluid samples collected 0, 3, and 6 h after feeding, and the microbial population was evaluated using rumen samples collected 3 h after feeding on d 12 of the covariate period, d 22 of each interval within the treatment period, and d 8 of the recovery period. Average DMI for the experiment was 7.04 ± 0.27 kg. Methane emissions were reduced by 59.2% when NOP was used (9.16 vs. 22.46 g/kg DMI; P < 0.01). Total VFA concentrations were not affected (P = 0.12); however, molar proportion of acetate was reduced and that for propionate increased when NOP was added (P < 0.01), which reduced the acetate to propionate ratio (3.0 vs. 4.0; P < 0.01). The total copy number of the 16S rRNA gene of total bacteria was not affected (P = 0.50) by NOP, but the copy number of the 16S rRNA gene of methanogens was reduced (P < 0.01) and the copy number of the 18S rRNA gene of protozoa was increased (P = 0.03). The residual effect of NOP for most of the variables studied was not observed or was minimal during the recovery period. These results demonstrated that the addition of NOP to a diet for beef cattle caused a sustained decrease of methanogenesis, with no sign of adaptation, and that these effects were reversed once NOP addition was discontinued