benzofurans and dihydroactinidiolide

Alzheimer's disease (AD) etiology has been studied for a long time and it is found to be multifaceted involving the accumulation of amyloid β and tau protein. Oxidative stress is an early event in AD associated neurodegeneration provoking neuronal death through mitochondrial dysfunction and activation of caspase-3. Therefore we tested the efficacy of dihydroactinidiolide (DHAc), a monoterpene lactone against the oxidative load involved in AD like pathological conditions induced by sodium dithionite, glutamate, amyloid β and colchicine in SH-SY5Y cells. Some of the indicators of neurotoxicity like acetylcholinesterase activity, intracellular reactive oxygen species (ROS), nitrite content, lipid peroxidation, protein carbonylation, nuclear and membrane damage were found to be significantly high in the toxicant treated cells when compared to the control cells while DHAc pretreatment significantly restored the toxicant induced neuronal damage signatures. Caspase-3 activity was found to be increased in the toxicant treated cells while DHAc significantly reduced it. Western blotting and RT-PCR revealed that DHAc significantly increased anti-apoptotic Bcl-2 expression and mRNA levels of Nrf2 and HO-1. Therefore DHAc was found to protect SH-SY5Y cells from neurotoxicant induced oxidative stress and apoptosis by regulating cellular antioxidant defenses and apoptosis related genes.

Topics: Apoptosis; bcl-2-Associated X Protein; Benzofurans; Caspase 3; Caspase Inhibitors; Cell Line, Tumor; Dose-Response Relationship, Drug; Heme Oxygenase-1; Humans; Neuroblastoma; Neurons; Neuroprotective Agents; NF-E2-Related Factor 2; Oxidative Stress

Dee are a unique and rapidly growing part of the global snack food market and are recognised as having distinct sensory properties (taste and texture). In this study, the development of important volatile aroma compounds over storage was evaluated and their chemical origin explained. Sweet potatoes were batch fried in high oleic sunflower oil (HOSO) and subjected to accelerated shelf life testing. Headspace volatiles were analysed using SPME GC-MS and correlated with sensory perception. All the components (sweet potatoes, oil and β-carotene) showed significant degradation after 3 weeks of storage at accelerated conditions (equivalent to 12 weeks in real-time at 25 °C). Marker volatiles associated with lipid oxidation such as hexanal, octanal, pentanal were identified, in addition to norisoprenoids from β-carotene degradation such as β-ionon, 5,6-epoxy-β-ionone, dihydroactinidiolide (DHA) and β-cyclocitral. The most prominent marker of lipid oxidation (hexanal) rapidly increased at week 1, whereas the carotene degradation makers did not rapidly increase until week 3 suggesting a delayed response. The frying temperature during the batch frying process of SPC was also shown to play a significant role in the sensory perception of the product over the shelf life. Overall, the results suggest that tight control of process variables and raw material design may enable extended shelf life and potentially enhanced health credentials for the product. These findings are unique to SPC, but also of value to the wider food industry.

Topics: Aldehydes; Benzofurans; beta Carotene; Cooking; Diterpenes; Food Industry; Gas Chromatography-Mass Spectrometry; Hot Temperature; Ipomoea batatas; Lipid Metabolism; Lipids; Norisoprenoids; Odorants; Oxidation-Reduction; Sensation; Sunflower Oil; Taste; Volatile Organic Compounds

Topics: Amnesia; Animals; Benzofurans; Biological Products; Cholinergic Antagonists; Male; Maze Learning; Mice; Neuroprotective Agents; Oxidative Stress; Scopolamine

Synthesis of natural products has speeded up drug discovery process by minimizing the time for their purification from natural source. Several diseases like Alzheimer's disease (AD) demand exploring multi targeted drug candidates, and for the first time we report the multi AD target inhibitory potential of synthesized dihydroactinidiolide (DA). Though the activity of DA in several solvent extracts have been proved to possess free radical scavenging, anti bacterial and anti cancer activities, its neuroprotective efficacy has not been evidenced yet. Hence DA was successfully synthesized from β-ionone using facile two-step oxidation method. It showed potent acetylcholinesterase (AChE) inhibition with half maximal inhibitory concentration (IC

Topics: Acetylcholinesterase; Amyloid beta-Peptides; Animals; Benzofurans; Catalytic Domain; Cell Line, Tumor; Cholinesterase Inhibitors; Free Radical Scavengers; Hemolysis; Humans; Mice; Molecular Docking Simulation; Molecular Dynamics Simulation; Neuroprotective Agents; Peptide Fragments; Protein Multimerization; Reactive Oxygen Species

Topics: Arabidopsis; Benzofurans; beta Carotene; Dose-Response Relationship, Radiation; Gene Expression Regulation, Plant; Light

Online capillary gas chromatography-isotope ratio mass spectrometry in both the combustion and the pyrolysis modes (HRGC-C/P-IRMS) was employed to perform authentication studies of the flavoring agent (+/-)-dihydroactinidiolide. Thus, the delta(13)C(V-PDB) and delta(2)H(V-SMOW) values of synthetic (ex synthetic beta-ionone and natural beta-carotene) as well as enzymatically (ex synthetic and natural beta-carotene) produced references were studied in comparison with those of the natural substance isolated from black (n = 17) and green teas (n = 6) ( Camellia sinensis ) as well as Rooibos tea ( Aspalathus linearis ) (n = 7). The isotope values determined for both the synthetic and enzymatically produced samples of (+/-)-dihydroactinidiolide reflected the influence of the origin of their educts. Hence, in cases when synthetic educts were used, the delta(13)C(V-PDB) and delta(2)H(V-SMOW) values ranged from -27.0 to -28.4 per thousand and from -28 to -169 per thousand, respectively, whereas the use of natural educts led to ranges from -30.3 to -31.6 per thousand and from -154 to -228 per thousand, respectively. As to the tea samples, delta(13)C(V-PDB) and delta(2)H(V-SMOW) values ranging from -29.0 to -34.1 per thousand and from -153 to -274 per thousand, respectively, were recorded for (+/-)-dihydroactinidiolide from black and green teas, whereas that from Rooibos tea showed (2)H/(1)H ratios ranging from -189 to -210 per thousand as well as slightly enriched values in the (13)C/(12)C ratios ranging from -24.4 to -27.1 per thousand.

Topics: Aspalathus; Benzofurans; beta Carotene; Beverages; Gas Chromatography-Mass Spectrometry; Norisoprenoids; Online Systems; Tea

On the basis of our recent findings that the germination of intact wheat grains with glumes (husks) belonging to dormant varieties was restrained as compared with that of dehusked grains, we have explored the identities of germination inhibitors in the glumes, resulting in the characterization of dihydroactinidiolide (1) and some aromatic compounds. A related natural product, tetrahydroactinidiolide (2), showed similar activity. The present study has demonstrated that the sensitivity in inhibition response of germination of the grains to 1 and 2 declined during after-ripening, in parallel with changes in germinability; the sprouting of after-ripened seeds on a whole spike was preventable by exogenous application of 2 in laboratory conditions, and germination of after-ripened grains was delayed by more than two weeks by the action of 1 or 2. The term "pseudodormancy" is proposed for the phenomenon of delay of germination caused by the inhibitor. After accumulation of additional evidence on inhibition response of actinidiolide-type natural products, structurally related to inhibitor 1, a mechanism concerning germination inhibition by 1 or 2 is proposed on the basis of the concept of nonbonding interaction with the inhibitors at an active site of an acceptor.

Topics: Benzofurans; Germination; Seeds; Triticum

Topics: Animals; Benzofurans; Exocrine Glands; Foxes; Male; Scent Glands; Sebum; Terpenes