Bidysoxyphenols A-C, dimeric sesquiterpene phenols from the leaves of Dysoxylum parasiticum (Osbeck) Kosterm.

Three new sesquiterpene phenol dimers, bidysoxyphenols A-C (2-4), along with two known compounds, namely sesquiterpene phenol (1) and ionone derivatives (5), were isolated from the leaves of Dysoxylum parasiticum (Osbeck) Kosterm. The structures of these new compounds, including their absolute configurations, were elucidated by nuclear magnetic resonance spectroscopy, ultraviolet spectroscopy, infrared spectroscopy, high-resolution electrospray ionization time-of-flight mass spectrometry, and electronic circular dichroism. Compounds 1 and 2 showed cytotoxicity against human promyelocytic leukemia cells, with IC50 values of 18.25 ± 1.52 and 39.04 ± 3.12 µM, respectively.

Fermented rice bran supplementation attenuates chronic colitis-associated extraintestinal manifestations in female C57BL/6N mice.

Patients with inflammatory bowel disease (IBD) have higher incidence of extraintestinal manifestations (EIM), including liver disorders, sarcopenia, and neuroinflammation. Fermented rice bran (FRB), generated from rice bran (RB), is rich in bioactive compounds, and exhibits anti-colitis activity. However, its role in EIM prevention is still unclear. Here, for the first time, we investigated whether EIM in female C57Bl/6N mice is attenuated by FRB supplementation. EIM was induced by repeated administration of 1.5% dextran sulfate sodium (DSS) in drinking water (4 d) followed by drinking water (12 d). Mice were divided into 3 groups-control (AIN93M), 10% RB, and 10% FRB. FRB ameliorated relapsing colitis and inflammation in muscle by significantly lowering proinflammatory cytokines Tnf-α and Il-6 in serum and advanced glycation end product-specific receptor (Ager) in serum and muscle when compared with the RB and control groups. As FRB reduced aspartate aminotransferase levels and oxidative stress, it might prevent liver disorders. FRB downregulated proinflammatory cytokine and chemokine transcripts responsible for neuroinflammation in the hippocampus and upregulated mRNA expression of G protein coupled receptors (GPRs), Gpr41 and Gpr43, in small and large intestines, which may explain the FRB-mediated protective mechanism. Hence, FRB can be used as a supplement to prevent IBD-associated EIM.

Cochlioquinone derivatives produced by coculture of endophytes, Clonostachys rosea and Nectria pseudotrichia.

Three new meroterpenoid derivatives, furanocochlioquinol (1) and furanocochlioquinone (2), as well as nectrianolin D (3), together with two known biogenetically related compounds 4 and 5 were isolated from a mixed culture of two mangrove-derived fungi, Clonostachys rosea B5-2 and Nectria pseudotrichia B69-1. The structures of 1-3 were deduced based on the interpretation of HRMS and NMR data. Compounds 1-5 exhibited cytotoxicity against human promyelocytic leukemia (HL60) cells with IC50 values ranging from 0.47 to 10.16 µM.

Fermented Rice Bran Supplementation Prevents the Development of Intestinal Fibrosis Due to DSS-Induced Inflammation in Mice.

Fermented rice bran (FRB) is known to protect mice intestines against dextran sodium sulfate (DSS)-induced inflammation; however, the restoration of post-colitis intestinal homeostasis using FRB supplementation is currently undocumented. In this study, we observed the effects of dietary FRB supplementation on intestinal restoration and the development of fibrosis after DSS-induced colitis. DSS (1.5%) was introduced in the drinking water of mice for 5 days. Eight mice were sacrificed immediately after the DSS treatment ended. The remaining mice were divided into three groups, comprising the following diets: control, 10% rice bran (RB), and 10% FRB-supplemented. Diet treatment was continued for 2 weeks, after which half the population of mice from each group was sacrificed. The experiment was continued for another 3 weeks before the remaining mice were sacrificed. FRB supplementation could reduce the general observation of colitis and production of intestinal pro-inflammatory cytokines. FRB also increased intestinal mRNA levels of anti-inflammatory cytokine, tight junction, and anti-microbial proteins. Furthermore, FRB supplementation suppressed markers of intestinal fibrosis. This effect might have been achieved via the canonical Smad2/3 activation and the non-canonical pathway of Tgf-ß activity. These results suggest that FRB may be an alternative therapeutic agent against inflammation-induced intestinal fibrosis.

Supplementation with Fermented Rice Bran Attenuates Muscle Atrophy in a Diabetic Rat Model.

Fermented rice bran (FRB), a prospective supplement, has been proven to ameliorate certain medical conditions. However, its nutraceutical effect on muscle atrophy has never been investigated. The present study aimed to evaluate the effect of FRB on muscle atrophy in a streptozotocin (STZ)-induced diabetic rat model. Three groups of Sprague-Dawley rats, namely the control, STZ, and FRB groups, were treated as follows. The diabetic groups (STZ and FRB) were injected intraperitoneally with STZ (40 mg/kg BW), whereas the control group was injected with the vehicle. The STZ and control groups were fed the AIN93M diet, and the FRB group was fed 10% of FRB based on the AIN93M diet. The diabetic groups had reduced muscle size compared to the control group; however, these changes were alleviated in the FRB group. Moreover, the FRB group had a significantly lower expression of FBXO32/Atrogin-1 and TRIM63/MuRF1 (p < 0.05) due to blocked NF-κB activation. In conclusion, the anti-inflammatory effect of FRB may be beneficial for ameliorating muscle atrophy in diabetic conditions.

New polyketides, paralactonic acids A-E produced by Paraconiothyrium sp. SW-B-1, an endophytic fungus associated with a seaweed, Chondrus ocellatus Holmes.

Five polyketides, paralactonic acids A-E (1-5) were isolated from Paraconiothyrium sp. SW-B-1, an endophytic fungus isolated from the seaweed, Chondrus ocellatus Holmes. Their structures were determined by various spectroscopic methods, predominantly by 2D NMR spectroscopic analyses. The absolute configurations of compounds 1-5 were determined by comparison of the experimental and calculated ECD spectra. Compound 5 showed moderate antibacterial activity and restored the growth of a mutant yeast strain inhibited by hyperactivated Ca2+-signaling.

Adenosine and adenosine-5'-monophosphate ingestion ameliorates abnormal glucose metabolism in mice fed a high-fat diet.

BACKGROUND: We have previously reported that ingestion of adenosine (ADN) and adenosine-5'-monophosphate (AMP) improves abnormal glucose metabolism in the stroke-prone spontaneously hypertensive rat model of non-obesity-associated insulin resistance. In this study, we investigated the effect of ADN and AMP ingestion on glucose metabolism in mice with high-fat diet-induced obesity. METHODS: Seven-week-old C57BL/6 J mice were administered distilled water (as a control), 10 mg/L ADN, or 13 mg/L AMP via their drinking water for 14 or 25 weeks, during which they were fed a high-fat diet. Oral glucose tolerance test (OGTT) was conducted on 21-week-old mice fasted for 16 h. Insulin tolerance test (ITT) was performed on 22-week-old mice fasted for 3 h. Blood and muscle were collected for further analysis of serum parameters, gene and protein expression levels, respectively. RESULTS: Glucose metabolism in the ADN and AMP groups was significantly improved compared with the control. OGTT and ITT showed that ADN and AMP groups lower than control group. Furthermore, phosphorylation of AMP-activated protein kinase (AMPK) and mRNA levels of genes involved in lipid oxidation were enhanced in the skeletal muscle of ADN- and AMP-treated mice. CONCLUSION: These results indicate that ingestion of ADN or AMP induces activation of AMPK in skeletal muscle and mitigates insulin resistance in mice with high-fat diet-induced diabetes.

New isocoumarins, naphthoquinones, and a cleistanthane-type diterpene from Nectria pseudotrichia 120-1NP.

Four new compounds, namely, nectriapyrones A (2) and B (3), nectriaquinone B (5), and zythiostromic acid C (8), were isolated from the brown rice culture of Nectria pseudotrichia 120-1NP together with four known compounds (1, 4, 6, and 7). To the best of our knowledge, this is the first report of 4 from a natural source. Their structures were determined on the basis of 1D/2D-NMR spectroscopy and HRESITOFMS data. In addition, the absolute configuration of secondary alcohols in 8 were determined using modified Mosher's ester method. All isolated compounds were evaluated for their antimicrobials activity, phytotoxicity, and cytotoxicity.

Dietary Supplementation of Fermented Rice Bran Effectively Alleviates Dextran Sodium Sulfate-Induced Colitis in Mice.

Rice bran (RB) is a major by-product of rice polishing and a rich source of bioactive compounds. Here, we investigated the anti-colitis effect of diet supplementation with fermented rice bran (FRB) in a murine model of ulcerative colitis. FRB was prepared by dual fermentation of RB using fungi and lactic acid bacteria. Colitis was induced in C57Bl/6N male mice (n = 8/group) by dextran sodium sulfate (DSS). Body weight change, disease activity index (DAI), histopathology score, tissue myeloperoxidase (MPO) activity, cytokine and chemokine transcript levels, and the production of short-chain fatty acids (SCFAs) and mucin in the colonic tissue were monitored. Based on histopathology scores, DSS induced severe mucosal inflammation, with an increased loss of crypts, and inflammatory cell infiltration in the control and RB groups, but not in the FRB group. MPO activity, thiobarbituric acid-reactive substance levels, and pro-inflammatory cytokine transcript (Tnf-α, Il-1ß, Il-6, and Il-17) levels were significantly higher in the control and RB groups than in the FRB group. Thus, dietary FRB attenuated intestinal inflammation owing to elevated SCFAs and tryptamine production, which might regulate tight junction barrier integrity and intestinal homeostasis. These results suggest that FRB could comprise an effective potential preventive agent for ulcerative colitis.

A phytotoxic bicyclic lactone and other compounds from endophyte Xylaria curta.

A new compound, (3aS,6aR)-4,5-dimethyl-3,3a,6,6a-tetrahydro-2H-cyclopenta [b]furan-2-one (2), along with two known metabolites, myrotheciumone A (1) and 4-oxo-4H-pyron-3-acetic acid (3) was isolated from the ethyl acetate extract of fermentation broth of Xylaria curta 92092022. The structures of these compounds were elucidated on the basis of spectroscopic methods (UV, IR, HRESITOFMS, 1D NMR, and 2D NMR). Compounds 1 and 2 showed moderate antibacterial and phytotoxic activities.

Fermented rice bran supplementation mitigates metabolic syndrome in stroke-prone spontaneously hypertensive rats.

BACKGROUND: Previous study shown that enzyme treated-rice bran effectively improved hypertension and glucose intolerance in stroke-prone spontaneously hypertensive rat (SHRSP). However, dual fermentation of rice bran's efficacy against metabolic syndrome in SHRSP is still unknown. METHODS: Fermented rice bran (FRB) was prepared by dual fermentation of rice bran using fungi and lactic acid bacteria. The effect of FRB on metabolic syndrome in stroke-prone spontaneously hypertensive rats (SHRSP) was investigated by single and chronic supplementation. RESULTS: Dual fermentation of rice bran enriches the functional value of rice bran. Single-dose oral administration of FRB (2 g/kg body weight) reduced systolic blood pressure; however, chronic supplementation with 5 % FRB (4 weeks) significantly reduced both systolic and diastolic blood pressure. FRB supplementation improved leptin impairment and increased serum adiponectin levels and angiotensin-converting enzyme inhibitory activity. Furthermore, FRB supplementation improved glucose tolerance and insulin sensitivity as well as serum insulin levels. Lipid profiles were also improved by the regulation of 5' adenosine monophosphate-activated protein kinase activation. Moreover, supplementation with FRB reduced the expressions of hepatic transcription factors such as liver X receptor alpha, sterol regulatory element-binding protein 1c, and carbohydrate-responsive element-binding protein alpha, as well as their target genes. In conclusion, dietary supplementation with FRB may lower hypertension and alleviate metabolic syndrome. CONCLUSION: Metabolic syndrome was better alleviated with FRB supplementation. We therefore suggest FRB as an alternative medicine to reduce the risks of lifestyle-related diseases.

Two new 5-deoxyflavan-3,4-diol glucosides from roots of Albizia chevalieri.

Phytochemical investigation of the roots of Albizia chevalieri led to the isolation of two new 5-deoxyflavan-3,4-diol glucosides from roots of A. chevalieri, Chevalieriflavanosides A and B. Their structures were established by 2D NMR techniques, UV, IR, CD, and mass spectrometry. Cytotoxicity of the two compounds was evaluated against acute promyelocytic leukemia HL60 cells. The antibacterial activities of 1 and 2 also were evaluated against Pseudomonas aeruginosa and Staphylococcus aureus using the agar diffusion test. Copyright © 2016 John Wiley & Sons, Ltd.

A new cytosporone derivative from the endophytic fungus Cytospora sp.

Japanese oak wilt (JOW) is a tree disease caused by the fungus Raffaelea quercivora, which is vectored by the ambrosia beetle, Platypus quercivorus. In a screening study of the inhibitory active compounds from fungi, a new cytosporone analogue, compound 1, was isolated from the endophytic fungus Cytospora sp. TT-10 isolated from Japanese oak, together with the known compounds, integracin A (2), cytosporones N (3) and A (4). Their structures were determined by extensive 1D- and 2D-NMR spectroscopic and mass spectral analyses. Compound 1 was identified as 4,5-dihydroxy-3-heptylphthalide and named cytosporone E. Compounds 2 and 3 showed antimicrobial activity against Raffaelea quercivora.

Isolation of a phomoxanthone A derivative, a new metabolite of tetrahydroxanthone, from a Phomopsis sp. isolated from the mangrove, Rhizhopora mucronata.

From the rice culture of Phomopsis sp. IM 41-1, isolated from the mangrove plant, Rhizhopora mucronata, two dimeric tetrahydroxanthones, phomoxanthone A (1) and 12-O-deacetyl-phomoxanthone A (2) were obtained. Their structures were determined by spectroscopic and spectrometric methods. Both compounds exhibited antimicrobial activities.

Polyketide metabolites from the endophytic fungus Microdiplodia sp. KS 75-1.

Through our screening for new natural compounds, four new polyketide metabolites, 7,8-dihydonivefuranone A (1), 6(7)-dehydro-8-hydroxyterrefuranone (2), 8-hydroxyterrefuranone (3), and 6-hydroxyterrefuranone (4) were isolated from the fermentation extract of Microdiplodia sp. KS 75-1, together with the known compounds nivefuranones A (5) and B (6); their structures were determined by spectroscopic (NMR, UV and IR) and MS analysis. Compounds 1, 2, 4 and 5 showed antimicrobial activity against Candida albicans and Staphylococcus aureus.