17092-92-1Relevant articles and documents
Dihydroactinidiolide, a natural product against Aβ25-35 induced toxicity in Neuro2a cells: Synthesis, in silico and in vitro studies
Das, Mamali,Prakash, Sengodu,Nayak, Chirasmita,Thangavel, Nandhini,Singh, Sanjeev Kumar,Manisankar, Paramasivam,Devi, Kasi Pandima
, p. 340 - 349 (2018/09/10)
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 (IC50) 34.03 nM, which was further supported by molecular docking results showing strong H bonding with some of the active site residues such as GLY117, GLY119 and SER200 of AChE. Further it displayed DPPH and (.NO) scavenging activity with IC50 value 50 nM and metal chelating activity with IC50 >270 nM. Besides, it significantly prevented amyloid β25-35 self-aggregation and promoted its disaggregation at 270 nM. It did not show cytotoxic effect towards Neuro2a (N2a) cells up to 24 h at 50 and 270 nM while it significantly increased viability of amyloid β25-35 treated N2a cells through ROS generation at both the concentrations. Cytotoxicity profile of DA against human PBMC was quite impressive. Hemolysis studies also revealed very low hemolysis i.e. minimum 2.35 to maximum 5.61%. It also had suitable ADME properties which proved its druglikeness. The current findings demand for further in vitro and in vivo studies to develop DA as a multi target lead against AD.
β-Carotene autoxidation: Oxygen copolymerization, non-vitamin A products, and immunological activity
Burton, Graham W.,Daroszewski, Janusz,Nickerson, James G.,Johnston, James B.,Mogg, Trevor J.,Nikiforov, Grigory B.
supporting information, p. 305 - 316 (2014/05/06)
Carotenoids are reported to have immunological effects independent of vitamin A activity. Although antioxidant activity has been suggested as a basis of action, the ability of carotenoids to autoxidize to numerous non-vitamin A products with immunological activity is an alternative yet to be fully explored. We have undertaken a systematic study of β-carotene autoxidation and tested the product mixture for immunological activity. Autoxidation proceeds predominantly by oxygen copolymerization, leading to a defined, reproducible product corresponding to net uptake of almost 8 molar equivalents of oxygen. The product, termed OxC-beta, empirical formula C40H60O 15 versus C40H56 for β-carotene, contains more than 30% oxygen (w/w) and 85% β-carotene oxygen copolymers (w/w) as well as minor amounts of many C8-C18 norisoprenoid compounds. No vitamin A or higher molecular weight norisoprenoids are present. The predominance of polymeric products has not been reported previously. The polymer appears to be a less polymerized form of sporopollenin, a biopolymer found in exines of spores and pollen. Autoxidations of lycopene and canthaxanthin show a similar predominance of polymeric products. OxC-beta exhibits immunological activity in a PCR gene expression array, indicating that carotenoid oxidation produces non-vitamin A products with immunomodulatory potential.
Cu(I)-catalyzed oxidative cyclization of alkynyl oxiranes and oxetanes
Gronnier, Colombe,Kramer, Soren,Odabachian, Yann,Gagosz, Fabien
, p. 828 - 831 (2012/03/07)
In the presence of a Cu(I) catalyst and a pyridine oxide, alkynyl oxiranes and oxetanes can be converted into functionalized five- or six-membered α,β-unsaturated lactones or dihydrofuranaldehydes. This new oxidative cyclization is proposed to proceed via an unusual allenyloxypyridinium intermediate.
Total synthesis of (±)-dihydroactinidiolide using selenium-stabilized carbenium ion
Dabdoub, Miguel J.,Silveira, Claudio C.,Lenard?o, Eder J.,Guerrero Jr., Palimécio G.,Viana, Luiz H.,Kawasoko, Cristiane Y.,Baroni, Adriano C.M.
scheme or table, p. 5569 - 5571 (2011/02/24)
A new, short total synthesis of dihydroactinidiolide 1 is described using selenium carbenium ion-promoted carbon-carbon bond formation as the key step. Our synthetic strategy starts with a lactonization reaction between 1,3,3-trimethylcyclohexene 13 and α-chloro-α-phenylseleno ethyl acetate 14, affording the key intermediate, α-phenylseleno-γ-butyro lactone 15, which reacted via a selenoxide elimination to the target compound 1.
Generation of norisoprenoid flavors from carotenoids by fungal peroxidases
Zelena, Kateryna,Hardebusch, Bjoern,Huelsdau, Baerbel,Berger, Ralf G.,Zorn, Holger
experimental part, p. 9951 - 9955 (2010/07/18)
To biotechnologlcally produce norisoprenoid flavor compounds, two extracellular peroxidases (MsP1 and MsP2) capable of degrading carotenoids were isolated from the culture supematants of the basidiomycete Marasmlus scorodonlus (garlic mushroom). The encod
Synthesis of loliolide, actinidiolide, dihydroactinidiolide, and aeginetolide via cerium enolate chemistry
Eidman, Kirk F.,MacDougall, Brian S.
, p. 9513 - 9516 (2007/10/03)
(Chemical Equation Presented) Loliolide, aeginetolide, actinidiolide, and dihydroactinidiolide were synthesized in racemic form from a single common intermediate, prepared through the 1,2 addition of the cerium enolate of ethyl acetate to 2,6,6-trimethylcylohexenone.
Effect of cis/trans isomerism of β-carotene on the ratios of volatile compounds produced during oxidative degradation
Wache, Yves,Bosser-DeRatuld, Aurelie,Lhuguenot, Jean-Claude,Belin, Jean-Marc
, p. 1984 - 1987 (2007/10/03)
β-Carotene is, when cleaved, an important source of flavor and aroma compounds in fruits and flowers. Among these aroma compounds, the main degradation products are β-ionone, 5,6-epoxy-β-ionone, and dihydroactinidiolide (DHA), which are associated by flavorists and perfumers with fruity, floral, and woody notes. These three species can be produced by degradation of β-carotene through an attack by enzyme-generated free radicals and a cleavage at the C9-C10 bond. This study investigated the influence of cis/trans isomerism at the C9-C10 bond on the production of β-carotene degradation compounds, first with a predictive approach and then experimentally with different isomer mixtures. β-Carotene solutions containing high ratios of 9-cis-isomers produced more DHA, suggesting a different pathway than for the transformation of all-trans-β-carotene to ionone and DHA. These results are important in the search for financially viable processes to produce natural carotene-derived aroma compounds.
Total Synthesis of (R)-Dihydroactinidiolide and (R)-Actinidiolide Using Asymmetric Catalytic Hetero-Diels-Alder Methodology
Yao, Sulan,Johannsen, Mogens,Hazell, Rita G.,J?rgensen, Karl Anker
, p. 118 - 121 (2007/10/03)
The total synthesis of the naturally occurring bicyclic lactones (R)-dihydroactinidiolide and (R)-actinidiolide is presented. The key step in the syntheses is the copper(II)-bisoxazoline-catalyzed hetero-Diels-Alder reaction of a cyclic diene with ethyl glyoxylate giving the hetero-Diels-Alder product in high yield and with very high regio-, diastereo-, and enantioselectivity. The total syntheses proceed via an intermediate, which also has the potential for a series of other natural products. The structure of the key intermediate is confirmed by X-ray analysis.
Convenient Synthesis of 2,2-Diethoxy-2,5-dihydrofurans, 2(5H)Furanones and 2-Ethoxyfurans. Crystal and Molecular Structure of a Barrelenone Diels-Alder Product
Saalfrank, Rolf W.,Hafner, Wieland,Markmann, Joachim,Welch, Andreas,Peters, Karl,Schnering, Hans Georg von
, p. 389 - 406 (2007/10/02)
Reaction of 1,2-hydroxyketones 5 with (2,2-diethoxyvinylidene)triphenylphosphorane (2) or (2,2-diethoxyvinyl)triphenylphosphonium tetrafluoroborates 6 yields the 2,2-diethoxy-2,5-dihydrofurans 9.Depending on the reaction conditions used, the orthoesters 9 can be hydrolized to give 2(5H)furanones 10 and 2-ethoxyfurans 11, respectively. 4,5-Dimethyl-5,6-dihydro-2-pyranone (20) and 8-methoxycoumarin (23) are prepared, starting from (2,2-diethoxyvinyl)triphenylphosphonium tetrafluoroborate (6a) and 1-hydroxy-2-methyl-3-butanone (16) or 2-hydroxy-3-methoxy-benzaldehyde (21).The 2-ethoxyfuranes 11 readily undergo Diels-Alder reactions with 2-chloracrylonitrile (24), maleic anhydride (26), N-phenyl-1,2,4-triazoline-3,5-dione (28) and dimethyl acetylenedicarboxylate (30) to give the corresponding Diels-Alder products 25, 27, 29 and 31, respectively.Contrary to 2-ethoxyfuran 11b, 11a reacts with two equivalents of acetylene 30, to yield barrelenone 34.The structure of 34 unequivocally is established by X-ray structure analysis. - Keywords: 2,2-Diethoxy-2,5-dihydrofurans, 2(5H)Furanones, 2-Ethoxyfurans, Barrelenone, Diels-Alder Products, X-Ray
Oxidative degradation of β-carotene and β-apo-8′-carotenal
Mordi, Raphael C.,Walton, John C.,Burton, Graham W.,Hughes, Lise,Ingold U., Keith,Lindsay A., David,Moffatt J., Douglas
, p. 911 - 928 (2007/10/02)
In the self-initiated oxidation of β-carotene with molecular oxygen the rate of oxygen uptake was shown to depend on the oxygen partial pressure. Epoxides, dihydrofurans, carbonyl compounds, carbon dioxide, oligomeric material, traces of alcohols, and probably carboxylic acids were formed. The main products in the early stage of the oxidation were shown to be 5,6-epoxy-β-carotene. 15,15′-epoxy-′-carotene, diepoxides, and a series of β-apo-carotenals and -carotenones. As the oxidation proceeded uncharacterised oligomeric material and the carbonyl compounds became more important and the epoxides degraded. In the final phase of the oxidation the longer chain β-apo-carotenals were themselves oxidized to shorter chain carbonyl compounds, particularly β-apo-13-carotenone, β-ionone, 5,6-epoxy-gb-ionone, dihydroactinidiolide and probably carboxylic acids. The effect of iron, copper and zinc stearates on the product composition and proportions was studied, as was the effect of light. The oxidation was inhibited by 2,6-di-t-butyl-4-methyphenol and α-tocopherol. The oxidations of β-apo-8′-carotenal and retinal under similar conditions were studied briefly, and the main products from the former compound were characterized. The initiation, the formation of the epoxides, the β-apo-carotenals and -carotenones, the successive chain shortening of the aldehydes to the ketones, and the formation of dihydroactinidiolide are explained in terms of free radical peroxidation chemistry.
