Oceanalin B, a Hybrid α,ω-Bifunctionalized Sphingoid Tetrahydroisoquinoline β-Glycoside from the Marine Sponge Oceanapia sp.

Oceanalin B (1), an α,ω-bipolar natural product belonging to a rare family of sphingoid tetrahydoisoquinoline β-glycosides, was isolated from the EtOH extract of the lyophilized marine sponge Oceanapia sp. as the second member of the series after oceanalin A (2) from the same animal. The compounds are of particular interest due to their biogenetically unexpected structures as well as their biological activities. The structure and absolute stereochemistry of 1 as a α,ω-bifunctionalized sphingoid tetrahydroisoquinoline β-glycoside was elucidated using NMR, CD and MS spectral analysis and chemical degradation. Oceanalin B exhibited in vitro antifungal activity against Candidaglabrata with a MIC of 25 μg/mL.

Chemical Constituents from Nicotiana tabacum L. and Their Antifungal Activity

A phytochemical investigation of an aqueous ethyl alcohol (EtOH) extract of the flowers of Nicotiana tabacum L . led to the identification of one new eudesmane-type sesquiterpenoid (1) and 14 known compounds, including 7 flavones (2-8), 6 phenolic acids (9-14), and 1 coumarin (15). The chemical structure of 1 was established on the basis of high-resolution electrospray ionization (HRESIMS) and 1D and 2D NMR analyses, while the other structures were elucidated by 1D NMR and LC–MS data. The antiphytopathogenic activities of all the isolated compounds were tested to determine their antifungal activity against Valsa mali var. mali, Alternaria porri, and Botrytis cinerea at a concentration of 10 µg/mL. Compound 4 exhibited more potent antifungal effects against Valsa mali var. mali with a % growth inhibition of 47.9 ± 1.2%, while the others only showed insignificant activities.

Is Phytomelatonin Complex Better Than Synthetic Melatonin? The Assessment of the Antiradical and Anti-Inflammatory Properties

This work aims to assess the recently established anti-inflammatory and antioxidant potential of melatonin of plant origin extracted from the plant matrix as a phytomelatonin complex (PHT-MLT), and compare its activity with synthetic melatonin (SNT-MLT) when used on its own or with vitamin C. For this purpose, a COX-2 enzyme inhibitory activity test, an antiradical activity in vitro and on cell lines assays, was performed on both PHT-MLT and SNT-MLT products. COX-2 inhibitory activity of PHT-MLT was found to be ca. 6.5 times stronger than that of SNT-MLT (43.3% and 6.7% enzyme inhibition, equivalent to the activity of acetylsalicylic acid in conc. 30.3 ± 0.2 and 12.0 ± 0.3 mg/mL, respectively). Higher antiradical potential and COX-2 inhibitory properties of PHT-MLT could be explained by the presence of additional naturally occurring constituents in alfalfa, chlorella, and rice, which were clearly visible on the HPLC-ESI-QTOF-MS fingerprint. The antiradical properties of PHT-MLT determined in the DPPH test (IC50 of 21.6 ± 1 mg of powder/mL) were found to originate from the presence of other metabolites in the 50% EtOH extract while SNT-MLT was found to be inactive under the applied testing conditions. However, the antioxidant studies on HaCaT keratinocytes stimulated with H2O2 revealed a noticeable activity in all samples. The presence of PHT-MLT (12.5, 25 and 50 µg/mL) and vitamin C (12.5, 25 and 50 µg/mL) in the H2O2-pretreated HaCaT keratinocytes protected the cells from generating reactive oxygen species. This observation confirms that MLT-containing samples affect the intracellular production of enzymes and neutralize the free radicals. Presented results indicated that MLT-containing products in combination with Vitamin C dosage are worth to be considered as a preventive alternative in the therapy of various diseases in the etiopathogenesis, of which radical and inflammatory mechanisms play an important role.

Effect of Batissa violacea celebensis Martens, 1897, Extract on β-Catenin Gene in Mice (Mus musculus) Induced by Azoxymethane and Dextran Sulfate Sodium using Polymerase Chain Reaction-restriction Fragment Length Polymorphism Method

BACKGROUND: At present, the β-catenin gene is a genetic change considered as the most important factor in the initiation and the progress of cancer. Bivalve extract contains steroid compounds that are thought to have an aphrodisiac and anti-inflammatory effect. The triterpenoid component detected in the crude bivalves extract is thought to have antitumor activity. AIM: This study aimed at knowing the effect of ethanol (EtOH) extract, ethyl acetate fraction, and the n-hexane fraction of pokea clam on β-catenin gene mutation in mice induced by azoxymethane (AOM) and dextran sulfate sodium (DSS) using the polymerase chain reaction-restriction fragment length polymorphism (PCR-RFLP) method. METHODS: The testing of the effect of pokea clam extract was conducted on several treatment groups, namely, AOM/DSSinfected mice treated with EtOH extract, ethyl acetate fraction, and N-hexane fraction. The positive control and the negative control of the three treatment groups were done by giving the extract with a dosage of 0.25 mg/bb to mice for 14 days. RESULTS: Based on the result of β-catenin gene amplification using the PCR method and RFLP analysis, the EtOH extract and ethyl acetate fraction groups had the same band, namely, 56 bp and 12 bp, consecutively; meanwhile, the n-hexane fraction was marked by the band formation of 191 bp, 82 bp and 48 bp, 69 bp, 116 bp, 151 bp, 180 bp, and 234 bp. From the types of band and the band size that have been formed, it shows that they have the same formation and similarities in the positive and negative treatment characterized by the amplification that occurred in the band size of 227 bp, and the result of amplification from RFLP analysis showed the same band with the same band size, namely, 89 and 138 bp. CONCLUSION: Based on this, it can be concluded that N-hexane fraction affects β-catenin gene mutation at the first or second base at codon position 32 or 33, and the third base, namely, the bands of 82 and 145 bp that also characterize the effect of N-hexane on β-catenin gene mutation at the second or third base. It is supported by the sequencing method obtaining the homological percentage of 99.13%.

Liposoluble portion of the red alga Pyropia yezoensis protects alcohol induced liver injury in mice

The hepatoprotective effect of liposoluble portion of Pyropia yezoensis (PYLP) was investigated against alcohol-induced liver injury in mice. Fatty acids were predominant in PYLP obtained from hexane fraction of 70% EtOH extract after ultrasonication. In particular, polyunsaturated fatty acids such as eicosapentaenoic acid and linoleic acid accounted for 56.91% of the total lipids. PYLP significantly reduced liver damage induced by the alcohol treatment in mice. PYLP treatment increased the activity of antioxidant enzymes including superoxide dismutase, catalase, and glutathion peroxidase by reducing thiobarbituric acid reactive substances. Histological observations showed that PYLP minimizes damage to living tissue induced by alcohol treatment by modulating the expression level of proteins involved in the anti-apoptotic signaling pathway. Our results suggest that PYLP, rich in polyunsaturated fatty acids extracted from the red alga P. yezoensis, will be useful as a potential liver protectant in the hangover industry.

Recovery of Bioactive Compounds from Strawberry (Fragaria × ananassa) Pomace by Conventional and Pressurized Liquid Extraction and Assessment Their Bioactivity in Human Cell Cultures

Pressing strawberries for juice generates large amounts of pomace, containing valuable nutrients and therefore requiring more systematic studies for their valorization. This study compared conventional solid-liquid (SLE) and pressurized liquid (PLE) extractions with ethanol (EtOH) and H2O for the recovery of bioactive compounds from strawberry pomace. The composition and bioactivities of the products obtained were evaluated. Among 15 identified compounds, quercetin-3-glucuronide, kaempferol-3-glucuronide, tiliroside, ellagic, malic, succinic, citric and p-coumaric acids were the most abundant constituents in strawberry pomace extracts. SLE-EtOH and PLE-H2O extracts possessed strong antioxidant capacity in DPPH• and ABTS•+ scavenging and oxygen radical absorbance capacity (ORAC) assays. Cytotoxicity, antiproliferative and cellular antioxidant activities in human cells of PLE-EtOH and PLE-H2O extracts were also evaluated. PLE-EtOH and PLE-H2O extracts possessed strong antioxidant activity, protecting Caco-2 cells upon stress stimuli, while PLE-EtOH extract showed higher antiproliferative activity with no cytotoxicity associated. In general, the results obtained revealed that properly selected biorefining schemes enable obtaining from strawberry pomace high nutritional value functional ingredients for foods and nutraceuticals.

Investigations into Chemical Components from Monascus purpureus with Photoprotective and Anti-Melanogenic Activities

Monascus species are asexually or sexually reproduced homothallic fungi that can produce a red colorant, specifically the so-called red yeast rice or Anka, which is used as a food ingredient in Asia. Traditional experiences of using Monascus for treating indigestion, enhancing blood circulation, and health remedies motivate us to investigate and repurpose Monascus-fermented products. Here, two new 5H-cyclopenta[c]pyridine type azaphilones, 5S,6S-monaspurpyridine A (1) and 5R,6R-monaspurpyridine A (2), two new xanthonoids, monasxanthones A and B (3 and 4), one new naphthalenone, monasnaphthalenone (5), and one new azaphilone, monapurpurin (6), along with two known compounds were isolated from the 70% EtOH extract of a citrinin-free domesticated strain M. purpureus BCRC 38110. The phytochemical properties of the xanthonoid and naphthalenone components were first identified from Monascus sp. differently from the representative ingredients of polyketide-derived azaphilones. UVB-induced cell viability loss and reactive oxygen species (ROS) overproduction in human keratinocytes were attenuated by monascuspirolide B (7) and ergosterol peroxide (8), indicating their photoprotective potentials. Ergosterol peroxide (8) decreased the melanin contents and tyrosinase activities of mouse melanocytes, depending on the concentration, suggesting their anti-melanogenic effects. In conclusion, six new and two known compounds were isolated from M. purpureus BCRC 38110, and two of them exhibited dermal protective activities. The results revealed the novel potential of M. purpureus for developing natural cosmeceutics against skin photoaging.

Leismanicidal Activity of Propolis Collected in the Semiarid Region of Brazil

Objective: The aim of the current study is to investigate the chemical composition, cytotoxic effect, and leishmanicidal activity of propolis collected in the semi-arid region of Bahia, Brazil.Methods: EtOH extract, hexane, EtOAc and MeOH fractions from propolis were analyzed by ultra-performance liquid chromatography coupled with diode array detector and quadrupole time-of-flight mass spectrometry. The identification was based on the exact mass, general fragmentation behaviors and UV absorption of the flavonoids. The in vitro cytotoxic effect and leishmanicidal activity of ethanolic extract, hexane, ethyl acetate, and methanolic fractions of propolis were evaluated.Results: Five triterpenes and twenty-four flavonoids were identified. The propolis did not present toxicity to the host cell up to the maximum concentration tested. In addition, all tested samples showed statistically significant activity against promastigotes of Leishmania chagasi and Leishmania amazonensis. Regarding the activity against amastigote forms of L. amazonensis, the hexane fraction, presented statistically significant activity with IC50 of 1.3 ± 0.1 μg/ml.Conclusion: The results support the idea that propolis can be used for future antileishmania studies.

Chemical constituents and antimicrobial activity of Lisotrigona cacciae propolis collected in Hoa Binh province

A chemical study on the propolis of the stingless bee Lisotrigona cacciae collected from Hoa Binh province led to the isolation of four compounds including cycloartenol (1), cochinchinone A (2), α-mangostin (3), and isomangiferolic acid (4). Mangifera indica (Xoài) and Cratoxylum cochinchinense (Thành Ngạnh Nam) were suggested to be the resin sources of the propolis. The propolis EtOH extract showed good antimicrobial activity against the Gram (+) strains B. cereus with an MIC value of 8 μg/ml. Among the isolated compounds, α-mangostin (3) was the most active and displayed strong activity against the five strains B. cereus, E. feacalis, S. aureus, P. aeruginosa, and the fungus C. albicans with MIC values of 1-2 μg/ml.

Isolation and Characterization of Glycosidic Tyrosinase Inhibitors from Typhonium giganteum Rhizomes

A new hydrocinnamoyl glucoside, 1-O-(4-hydroxyhydrocinnamoyl)-β-D-glucopyranose (1), together with fifteen known glycosides, including two phenylethanoid glycosides (2–3), two cinnamoyl glycosides (4–5), six phenolic glycosides (6–11), one lignan glycoside (12) and four megastigmane glycosides (13–16) were isolated from a 95% EtOH extract of the Typhonium giganteum rhizomes. The sixteen glycosides were structurally characterized by NMR, HRESIMS, enzymatic hydrolysis and comparison with literature. Upon evaluating inhibitory activities of compounds 1–16 against mushroom tyrosinase at 25 μM, compounds 10 and 11 exhibited obvious inhibitory activities, with %inhibition values of 20.94±0.59%, 23.28±1.09%, respectively, with arbutin used as the positive control (26.21±0.58%).