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Neuroprotective Effects of Trilobatin, a Novel Naturally Occurring Sirt3 Agonist from Lithocarpus polystachyus Rehd., Mitigate Cerebral Ischemia/Reperfusion Injury: Involvement of TLR4/NF-κB and Nrf2/Keap-1 Signaling
Aims: Neuroinflammation and oxidative stress are deemed the prime causes of brain injury after cerebral ischemia/reperfusion (I/R). Since the silent mating-type information regulation 2 homologue 3 (Sirt3) pathway plays an imperative role in protecting against neuroinflammation and oxidative stress, it has been verified as a target to treat ischemia stroke. Therefore, we attempted to seek novel Sirt3 agonist and explore its underlying mechanism for stroke treatment both in vivo and in vitro. Results: Trilobatin (TLB) not only dramatically suppressed neuroinflammation and oxidative stress injury after middle cerebral artery occlusion in rats, but also effectively mitigated oxygen and glucose deprivation/reoxygenation injury in primary cultured astrocytes. These beneficial effects, along with the reduced proinflammatory cytokines via suppressing Toll-like receptor 4 (TLR4) signaling pathway, lessened oxidative injury via activating nuclear factor erythroid 2-related factor 2 (Nrf2) signaling pathways, in keeping with the findings in vivo. Intriguingly, the TLB-mediated neuroprotection on cerebral I/R injury was modulated by reciprocity between TLR4-mediated neuroinflammatory responses and Nrf2 antioxidant responses as evidenced by molecular docking and silencing TLR4 and Nrf2, respectively. Most importantly, TLB not only directly bonded to Sirt3 but also increased Sirt3 expression and activity, indicating that Sirt3 might be a promising therapeutic target of TLB. Innovation: TLB is a naturally occurring Sirt3 agonist with potent neuroprotective effects via regulation of TLR4/nuclear factor-kappa B and Nrf2/Kelch-like ECH-associated protein 1 (Keap-1) signaling pathways both in vivo and in vitro. Conclusion: Our findings indicate that TLB protects against cerebral I/R-induced neuroinflammation and oxidative injury through the regulation of neuroinflammatory and oxidative responses via TLR4, Nrf2, and Sirt3, suggesting that TLB might be a promising Sirt3 agonist against ischemic stroke.
Chen, Nana,Gao, Jianmei,Gong, Qihai,Lei, Yaying,Li, Na,Shi, Jingshan,Wang, Wei,Xu, Fan
p. 117 - 143
(2020)
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Catalytic hydrogenation reaction of naringin-chalcone. Study of the electrochemical reaction
The electrocatalytic hydrogenation reaction of naringin derivated chalcone is studied. The reaction is carried out with different catalysts in order to compare with the classic catalytic hydrogenation.
Nazareno,Giannuzzo,Mishima,Lopez De Mishima
p. 589 - 590
(2000)
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Natural chalcones elicit formation of specialized pro-resolving mediators and related 15-lipoxygenase products in human macrophages
Specialized pro-resolving mediators (SPMs) comprise lipid mediators (LMs) produced from polyunsaturated fatty acids (PUFAs) via stereoselective oxygenation particularly involving 12/15-lipoxygenases (LOXs). In contrast to pro-inflammatory LMs such as leuk
Cala Peralta, Antonio,Helesbeux, Jean-Jacques,Hoff, Daniel,Hofstetter, Robert Klaus,Jordan, Paul M.,Koeberle, Andreas,Kretzer, Christian,Meyer, Katharina P. L.,Richomme, Pascal,Schuster, Daniela,Seraphin, Denis,Stuppner, Hermann,Temml, Veronika,Viault, Guillaume,Werner, Markus,Werz, Oliver
(2021/12/24)

METHODS FOR TREATING CHRONIC FATIGUE SYNDROME AND MYALGIC ENCEPHALOMYELITIS
In one aspect the invention relates to a method of treatment selected from the group consisting of: (a) treating a symptom such as pain in a subject identified or diagnosed as having Myalgic Encephalomyelitis/Chronic Fatigue Syndrome (ME/CFS); (b) treating a symptom such as pain in a subject having dysfunctional TRPM3 ion channel activity; (c) restoring NK cell function in a subject having dysfunctional TRPM3 ion channel activity; and (d) restoring calcium homeostasis in a subject having dysfunctional TRPM3 ion channel activity. The method comprises the step of administering to the subject a therapeutically effective amount of at least one therapeutic compound selected from the group consisting of: (i) an opioid receptor antagonist; (ii) an opioid antagonist; and (iii) a therapeutic compound that restores TRPM3 ion channel activity. In some embodiments the therapeutic compound is naltrexone hydrochloride.
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(2021/03/13)

Quinoid dihydrochalcone dicarbonyl glycoside compound with glucose on A ring, preparation method and neuroprotective activity thereof
The invention discloses a class of quinoid dihydrochalcone C-glycoside compounds with glucose on a ring A, a preparation method and anti-cerebral ischemia injury activity thereof, wherein the compoundhas a structure represented by a general formula (I). The preparation method of the compound comprises the following steps: (1) synthesizing a 2,4,6-trihydroxy dihydrochalcone compound; (2) synthesizing a 2,4,6-trihydroxy-3,5-diglucosyl dihydrochalcone C-glycoside compound; and (6) synthesizing a class of quinoid dihydrochalcone C-glycoside compound with glucose in the A ring. The compound disclosed by the invention is simple in preparation method and has a remarkable effect of resisting cerebral ischemia injury.
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Paragraph 0070-0075

(2020/09/23)

Novel compound from plasma-treated phloridzin and anti-obesity composition comprising the same as effective component
The present invention relates to a novel compound derived from plasma-treated phloridzin and an anti-obesity composition comprising the same as an effective component and, more specifically, to a diameric compound derived from phloridzin, which is newly formed by plasma-treating phloridzin (methylene-bis-phloridzin, diglucosyl-methylene-bis-phloridzin, and methylene-bis-phloretin), and to an anti-obesity composition comprising the same as an effective component. In particular, the compound derived from phloridzin, comapred to phloridzin, inhibits the activity of pancreatic lipase and enhances the effect of suppressing fat accumulation during differentiation of fat cells. In particular, the methylene-bis-phloretin of the present invention, a diameric body formed by phloretin using a methyl group, a form of which sugars are removed from phloridzin, has excellent inhibitory effect on fat accumlation as compared to phloretin, and thus may be beneficially used as a material for anti-obesity therapeutic agents or anti-obesity functional health foods.COPYRIGHT KIPO 2019
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Paragraph 0039-0042

(2019/08/16)

Base-catalyzed oxidative dearomatization of multisubstituted phloroglucinols: An easy access to C-glucosyl 3,5,6-trihydroxycyclohexa-2,4-dienone derivatives
An efficient and simple method for the protecting group-free synthesis of C-glucosyl 3,5,6-trihydroxycyclohexa-2,4-dienone has been firstly established. This method is compatible with various functional groups, such as benzyl and phenethyl groups, affording a range of C-glucosyl 3,5,6-trihydroxycyclohexa-2,4-dienone derivatives.
Gao, Wan,Chen,Yang,Jiang, Jianshuang,Feng, Ziming,Zhang, Xu,Yuan,Zhang, Peicheng
supporting information

(2019/08/20)

Targeting type 2 diabetes with c-glucosyl dihydrochalcones as selective sodium glucose co-transporter 2 (sglt2) inhibitors: Synthesis and biological evaluation
Inhibiting glucose reabsorption by sodium glucose co-transporter proteins (SGLTs) in the kidneys is a relatively new strategy for treating type 2 diabetes. Selective inhibition of SGLT2 over SGLT1 is critical for minimizing adverse side effects associated with SGLT1 inhibition. A library of C-glucosyl dihydrochalcones and their dihydrochalcone and chalcone precursors was synthesized and tested as SGLT1/SGLT2 inhibitors using a cell-based fluorescence assay of glucose uptake. The most potent inhibitors of SGLT2 (IC50 = 9.23 nM) were considerably weaker inhibitors of SGLT1 (IC50 = 10.19 μM). They showed no effect on the sodium independent GLUT family of glucose transporters, and the most potent ones were not acutely toxic to cultured cells. The interaction of a C-glucosyl dihydrochalcone with a POPC membrane was modeled computationally, providing evidence that it is not a pan-assay interference compound. These results point toward the discovery of structures that are potent and highly selective inhibitors of SGLT2.
Jesus, Ana R.,Vila-Vi?osa, Diogo,Machuqueiro, Miguel,Marques, Ana P.,Dore, Timothy M.,Rauter, Amélia P.
p. 568 - 579
(2017/02/05)

Rapid preparation of (methyl)malonyl coenzyme A and enzymatic formation of unusual polyketides by type III polyketide synthase from Aquilaria sinensis
(Methyl)malonyl coenzyme A was rapidly and effectively synthesized by a two-step procedure involving preparation of N-hydroxysuccinimidyl (methyl)malonate from (methyl)Meldrum's acid, and followed by transesterification with coenzyme A. The synthesized (methyl)malonyl coenzyme A could be well accepted and assembled to 4-hydroxy phenylpropionyl coenzyme A by type III polyketide synthase from Aquilaria sinensis to produce dihydrochalcone and 4-hydroxy-3,5-dimethyl-6-(4-hydroxyphenethyl)-2H-pyrone as well as 4-hydroxy-3,5-dimethyl-6-(5-(4-hydroxyphenyl)-3-oxopentan-2-yl)-2H-pyrone.
Gao, Bo-Wen,Wang, Xiao-Hui,Liu, Xiao,Shi, She-Po,Tu, Peng-Fei
supporting information
p. 1279 - 1283
(2015/03/14)

Towards the synthesis of glycosylated dihydrochalcone natural products using glycosyltransferase-catalysed cascade reactions
Regioselective O-β-D-glucosylation of flavonoid core structures is used in plants to create diverse natural products. Their prospective application as functional food and pharmaceutical ingredients makes flavonoid glucosides interesting targets for chemical synthesis, but selective instalment of a glucosyl group requires elaborate synthetic procedures. We report glycosyltransferase-catalysed cascade reactions for single-step highly efficient O-β-D-glucosylation of two major dihydrochalcones (phloretin, davidigenin) and demonstrate their use for the preparation of phlorizin (phloretin 2′-O-β-d-glucoside) and two first-time synthesised natural products, davidioside and confusoside, obtained through selective 2′- and 4′-O-β-d-glucosylation of the dihydroxyphenyl moiety in davidigenin, respectively. Parallel biocatalytic cascades were established by coupling uridine 5′-diphosphate (UDP)-glucose dependent synthetic glucosylations catalysed by herein identified dedicated O-glycosyltransferases (OGTs) to UDP dependent conversion of sucrose by sucrose synthase (SuSy; from soybean). The SuSy reaction served not only to regenerate the UDP-glucose donor substrate for OGT (up to 9 times), but also to overcome thermodynamic restrictions on dihydrochalcone β-d-glucoside formation (up to 20% conversion and yield enhancement). Using conditions optimised for overall coupled enzyme activity, target 2′-O- or 4′-O-β-d-glucoside was obtained in ≥88% yield from reactions consisting of 5 mM dihydrochalcone acceptor, 100 mM sucrose, and 0.5 mM UDP. Davidioside and confusoside were isolated and their proposed chemical structures confirmed by NMR. OGT-SuSy cascade transformations present a green chemistry approach for efficient glucosylation in natural products synthesis. the Partner Organisations 2014.
Gutmann, Alexander,Bungaruang, Linda,Weber, Hansjoerg,Leypold, Mario,Breinbauer, Rolf,Nidetzky, Bernd
supporting information
p. 4417 - 4425
(2014/11/08)

Enzymatic conversion of flavonoids using bacterial chalcone isomerase and enoate reductase
Flavonoids are a large group of plant secondary metabolites with a variety of biological properties and are therefore of interest to many scientists, as they can lead to industrially interesting intermediates. The anaerobic gut bacterium Eubacterium ramulus can catabolize flavonoids, but until now, the pathway has not been experimentally confirmed. In the present work, a chalcone isomerase (CHI) and an enoate reductase (ERED) could be identified through whole genome sequencing and gene motif search. These two enzymes were successfully cloned and expressed in Escherichia coli in their active form, even under aerobic conditions. The catabolic pathway of E. ramulus was confirmed by biotransformations of flavanones into dihydrochalcones. The engineered E. coli strain that expresses both enzymes was used for the conversion of several flavanones, underlining the applicability of this biocatalytic cascade reaction.
Gall, Mechthild,Thomsen, Maren,Peters, Christin,Pavlidis, Ioannis V.,Jonczyk, Patrick,Grunert, Philipp P.,Beutel, Sascha,Scheper, Thomas,Gross, Egon,Backes, Michael,Geissler, Torsten,Ley, Jakob P.,Hilmer, Jens-Michael,Krammer, Gerhard,Palm, Gottfried J.,Hinrichs, Winfried,Bornscheuer, Uwe T.
supporting information
p. 1439 - 1442
(2014/03/21)

Microbial synthesis of dihydrochalcones using Rhodococcus and Gordonia species
Chalcones are important compounds in food and cosmetics industry, and in food chemistry research. We have developed a method of synthesis of dihydrochalcones from flavanone and α,β-unsaturated chalcones by microbial hydrogenation. It has been found that bacterial strains of Rhodococcus sp. and Gordonia sp. can be successfully used in the key step of dihydrochalcones synthesis. This kind of activity has not been previously examined. Twelve microorganisms were initially screened for their ability to catalyze biotransformation reactions of selected flavonoid compounds. Of these, Rhodococcus sp. and Gordonia sp. transformed flavanone and chalcones to hydrogenation products in good isolated yield of 13-94%.
Stompor, Monika,Potaniec, Bartomiej,Szumny, Antoni,Zielinski, Pawe,Zonierczyk, Anna Katarzyna,Aniol, Miroslaw
p. 283 - 288
(2013/10/22)

Synthesis of non-natural flavanones and dihydrochalcones in metabolically engineered yeast
Flavonoids are plant phenolic compounds that have many interesting medicinal properties. Therefore, there is interestin the synthesisof non-natural flavonoidsas they may possess neworenhanced biological activities. In this study, metabolically engineered Saccharomyces cerevisiae expressing 4-coumaroyl:CoA-ligase (4CL) and chalcone synthase (CHS)was explored as a platform for producingnon-natural flavanones and dihydrochalcones. By precursor addition of cinnamic acid analogues to the engineered yeast, numerous non-natural flavanones and dihydrochalcones were formed in vivo. Also, several CHS derailment products were formed. Of the isolated compounds, one flavanone and three derailment products were found to be novel compounds.
Werner, Sean R.,Chen, Hao,Jiang, Hanxiao,Morgan, John A.
body text
p. 257 - 263
(2010/11/18)

Synthesis and biological evaluation of phloridzin analogs as human concentrative nucleoside transporter 3 (hCNT3) inhibitors
Nucleoside transporter inhibitors have potential therapeutic applications as anticancer, antiviral, cardioprotective and neuroprotective agents. Although quite a few potent inhibitors of the equilibrative nucleoside transporters are known, largely missing are the concentrative nucleoside transporter inhibitors. Phloridzin (3, Ki = 16.00 μM) is a known moderate inhibitor of the concentrative nucleoside transporters. We have synthesized and evaluated analogs of phloridzin at the hCNT3 nucleoside transporter. Within the series of synthesized analogs compound 16 (Ki = 2.88 μM), possessing a ribofuranose sugar unit instead of a glucopyranose as present in phloridzin, exhibited the highest binding affinity at the hCNT3 transporter. Phloridzin and compound 16 have also been shown to be selective for the hCNT3 transporter as compared with the hENT1 transporter. Compound 16 can serve as a new lead which after further modifications could yield selective and potent hCNT3 inhibitors.
Gupte, Amol,Buolamwini, John K.
supporting information; experimental part
p. 917 - 921
(2009/09/06)

Hydrolysis of toxic natural glucosides catalyzed by cyclodextrin dicyanohydrins
The hydrolysis of toxic 7-hydroxycoumarin glucosides and other aryl and alkyl glucosides, catalyzed by modified α- and β-cyclodextrin dicyanohydrins, was investigated using different UV, redox, or HPAEC detection assays. The catalyzed reactions all followed Michaelis-Menten kinetics, and an impressive rate increase of up to 7569 (kcat/kuncat) was found for the hydroxycoumarin glucoside substrate 4-MUGP. Good and moderate degrees of catalysis (kcat/kuncat) of up to 1259 were found for the natural glucosides phloridzin and skimmin. By using a newly developed catechol detection UV-assay, a weak degree of catalysis was also found for the toxic hydroxycoumarin esculin. A novel synthesized diaminomethyl β-cyclodextrin showed a weak catalysis of p-nitrophenyl β-D-glucopyranoside hydrolysis. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Bjerre, Jeannette,Nielsen, Erik Holm,Bols, Mikael
p. 745 - 752
(2008/09/17)

AROMA COMPOSITIONS OF ALKAMIDES WITH HESPERETIN AND/OR 4-HYDROXYDIHYDROCHALCONES AND SALTS THEREOF FOR ENHANCING SWEET SENSORY IMPRESSIONS
The invention primarily relates to aroma compositions of (i) certain saliva-stimulating alkamides having a tingling, pungent and/or hot flavor (such as for example pellitorines, spilanthol) with (ii) hesperetin (5,7-dihydroxy-3-(3-hydroxy-4-methoxyphenyl)-chroman-4-one) or the enantiomers and/or salts thereof and/or (iii) 4-hydroxydihydrochalcones (3-(4-hydroxyphenyl)-1-phenylpropan-1-ones) and/or the salts thereof, the use thereof to enhance the sweet flavor of sweet-tasting substances or the sweet odor impression of aroma substances which give rise to a sweet odor impression, but in particular to enhance the sweet initial flavor or odor (initial sweetness). The invention thus relates to the use of said aroma compositions as general sweetness enhancers and enhancers of initial sweetness. The invention further relates to certain preparations which contain an effective amount of said aroma compositions of (i) alkamides (such as in particular pellitorines, spilanthol) with (ii) hesperetin or the enantiomers and/or salts thereof and/or (iii) 4-hydroxydihydrochalcones and/or the salts thereof and methods for enhancing the sweet flavor or initial sweetness of a sweet-tasting substance or the sweet odor impression or initial sweetness of an aroma substance which gives rise to a sweet odor impression. The invention also relates to the use of certain alkamides (i) to enhance the initial sweetness of a preparation comprising (ii) hesperetin or the enantiomers and/or salts thereof and/or (iii) 4-hydroxydihydrochalcones and/or the salts thereof and (b) sweet-tasting substances and/or (c) aroma substances which give rise to a sweet odor impression.
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(2008/12/07)

A concise synthesis of polyhydroxydihydrochalcones and homoisoflavonoids
A general and single step synthesis of polyhydroxydihydrochalcones from the readily available phenols and dihydrocinnamic acids using BF 3·Et2O is described. The method allows the synthesis of a wide range of compounds with multiple phenolic hydroxyls and other substituents. These dihydrochalcones are converted into homoisoflavonoids by DMF/PCl5 and the methodology has been applied to the synthesis of naturally occurring phloretin and 5,7-dihydroxy-3-[(4-hydroxyphenyl)methyl]-4H- chromen-4-one. The antioxidant activity of dihydrochalcones and homoisoflavonoids was determined by superoxide free radical (NBT) and DPPH free radical scavenging methods. Polyhydroxydihydrochalcones 3c, 3f, 3g and homoisoflavonoids 4c, 4f, 4g displayed excellent antioxidant activity.
Siddaiah, Vidavalur,Rao, Chunduri Venkata,Venkateswarlu, Somepalli,Subbaraju, Gottumukkala V.
p. 841 - 846
(2007/10/03)

Cosmetic composition
A composition for topical application to the skin in order to promote the repair of photo-damaged or aged skin and/or to reduce or prevent damaging effects of ultra-violet light on skin and/or to lighten the skin comprising a hydrocalchone of general structure: STR1 wherein R1, R2 and R3, which may be the same or different, represent H, --OH, --OR or --COR (where R is a C1-20 alkyl group); R4, R5, R6 and R7, which may be the same or different, represent H or --COR (where R is as herein before defined). Optional additional ingredients include sunscreens and other skin lightening skin lightening agents, particularly retinol or derivatives thereof.
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(2008/06/13)

Anti-ulcer agent comprising chalcone derivative as effective ingredient and novel chalcone derivative
The present invention relates to an anti-ulcer agent comprising a compound represented by the following general formula I as the effective ingredient, and a novel chalcone derivative included in the compound represented by this general formula I: STR1 wherein X and Y independently stand for a hydrogen atom or together form a single bond, R1 stands for a hydroxyl group, an acetoxy group, a carboxymethoxy group or a methoxycarbonylmethoxy group, R2 stands for a hydrogen atom, an isoprenyl group, isopentyl group or a propyl group, R3 stands for hydroxyl group or a methoxy group, R4 stands for a hydrogen atom, a hydroxyl group or a methoxy group, R5 stands for a hydrogen atom, a hydroxyl group, a methoxy group or an isopentyl group, R6 stands for a hydroxyl group, a methoxy group or a carboxymethoxy group, and R7 stands for a hydrogen atom or a methoxy group.
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(2008/06/13)

Synthesis of natural 5,7-dihydroxy-3-(4-hydroxybenzyl)chromone and its congener
2-Hydroxy-4,6-dibenzyloxyacetophenone (1) on condensation with p-benzyloxybenzaldehyde (2a) or veratraldehyde (2b) gives the corresponding chalcone (3a or 3b) which is reduced to dihydrochalcone (4a or 4b).The latter undergoes cyclization with DMF in the presence of borontrifluoride etherate and methanesulphonyl chloride to give 5,7-dihydroxy-3-(4-hydroxybenzyl)chromone (5a), identical with naturally occuring compound, or 5,7-dihydroxy-3-(3,4-dimethoxybenzyl)chromone (5b).
Jain, A. C.,Paliwal, Poonam
p. 416 - 418
(2007/10/02)

CATALYTIC TRANSFER HYDROGENATION, A FACILE CONVERSION OF HYDROXYFLAVANONES INTO HYDROXYDIHYDROCHALCONES
Catalytic transfer hydrogenation of naringenin, hesperetin and eriodictyol using sodium formate as the donor and commercially available Pd/C gives the respective hydroxydihydrochalcones in good yields.The method is an excellent alternative to catalytic hydrogenation.
Krishnamurty, H.G.,Sathyanarayana, S.
p. 119 - 124
(2007/10/02)

Chemistry of Homoisoflavonoids: Synthesis of Polyhydroxy 3-Benzylchromones and 3-Benzylchroman-4-ones without Protection and Deprotection of Hydroxyl Groups and a Convenient Preparation of Benzylidenechroman-4-ones
Catalytic transfer hydrogenation of hydroxyflavanones gives hydroxydihydrochalcones.These dihydrochalcones are converted into hydroxyhomoisoflavones and homoisoflavanones without protection and deprotection of hydroxyl groups.The condensation between chromanones and aryl aldehydes in the presence of dry p-toluenesulfonic acid in benzene or toluene gives benzylidenechromanones in good yields.The method is far superior to all other existing procedures.
Sathyanarayana, S.,Krishnamurty, H. G.
p. 899 - 901
(2007/10/02)