Macrocyclic diterpenoids from the seeds of Euphorbia peplus with potential activity in inducing lysosomal biogenesis.

Abstract:

:The first phytochemical investigation of the seeds of Euphorbia peplus led to the isolation and characterization of five new (1-5), named euphopepluanones A-E, and five known diterpenoids (6-10). Their structures were established by extensive spectroscopic analysis and X-ray crystallographic experiments. Euphopepluanones A-E (1-3) feature a very rare 5/11/5-tricyclic skeleton, and euphopepluanones D-E (4-5) represent the first report of lathyrane type diterpenoids found in E. peplus. The new compounds 1-5 were assessed for their activities to induce lysosomal biogenesis through LysoTracker Red staining, in which compounds 1 and 3 could significantly induce lysosomal biogenesis. In addition, compounds 1 and 3 could promote the nuclear translocation of TFEB, a master transcriptional factor of lysosomal genes, indicating that compounds 1 and 3 induced lysosomal biogenesis through activation of TFEB.

journal_name

Bioorg Chem

journal_title

Bioorganic chemistry

authors

Chen YN,Ding X,Lu QY,Li DM,Li BT,Liu S,Yang L,Zhang Y,Di YT,Fang X,Hao XJ

doi

10.1016/j.bioorg.2020.104464

subject

Has Abstract

pub_date

2020-12-01 00:00:00

pages

104464

eissn

0045-2068

issn

1090-2120

pii

S0045-2068(20)31762-4

journal_volume

105

pub_type

杂志文章
  • Synthesis, anticancer effect and molecular modeling of new thiazolylpyrazolyl coumarin derivatives targeting VEGFR-2 kinase and inducing cell cycle arrest and apoptosis.

    abstract::New thiazolylpyrazolyl coumarin derivatives were synthesized and tested for their anticancer potential in vitro against five different human cell lines, including breast MCF-7, lung A549, prostate PC3, liver HepG2 and normal melanocyte HFB4. Breast carcinoma revealed higher sensitivity towards compounds 7a, 8c, 9b, 9c...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2018.12.040

    authors: Mohamed TK,Batran RZ,Elseginy SA,Ali MM,Mahmoud AE

    更新日期:2019-04-01 00:00:00

  • 1-(4-Methane(amino)sulfonylphenyl)-3-(4-substituted-phenyl)-5-(4-trifluoromethylphenyl)-1H-2-pyrazolines/pyrazoles as potential anti-inflammatory agents.

    abstract::2-Pyrazolins 14a-l and pyrazoles 15a-l were designed as celecoxib analogs for the evaluation of their in vitro COX-1/COX-2 inhibitory activity and the in vivo anti-inflammatory activity. Compounds 14i, 15a, 15d and 15f were the most COX-2 selective derivatives (S.I.=5.93, 6.08, 5.03 and 5.27 respectively) while the py...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2015.09.002

    authors: Abdellatif KR,Elshemy HA,Azoz AA

    更新日期:2015-12-01 00:00:00

  • Dual targeting DNA gyrase B (GyrB) and topoisomerse IV (ParE) inhibitors: A review.

    abstract::GyrB and ParE are type IIA topoisomerases and found in most bacteria. Its function is vital for DNA replication, repair and decatenation. The highly conserved ATP-binding subunits of DNA GyrB and ParE are structurally related and have been recognized as prime candidates for the development of dual-targeting antibacter...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.bioorg.2015.07.004

    authors: Azam MA,Thathan J,Jubie S

    更新日期:2015-10-01 00:00:00

  • The adenosine receptor affinities and monoamine oxidase B inhibitory properties of sulfanylphthalimide analogues.

    abstract::Based on a report that sulfanylphthalimides are highly potent monoamine oxidase (MAO) B selective inhibitors, the present study examines the adenosine receptor affinities and MAO-B inhibitory properties of a series of 4- and 5-sulfanylphthalimide analogues. Since adenosine antagonists (A1 and A2A subtypes) and MAO-B i...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2015.02.005

    authors: Van der Walt MM,Terre'Blanche G,Petzer A,Petzer JP

    更新日期:2015-04-01 00:00:00

  • α-bisabolol β-D-fucopyranoside as a potential modulator of β-amyloid peptide induced neurotoxicity: An in vitro &in silico study.

    abstract::Alzheimer's disease (AD) is a multifaceted neurodegenerative disorder affecting the elderly people. For the AD treatment, there is inefficiency in the existing medication, as these drugs reduce only the symptoms of the disease. Since multiple pathological proteins are involved in the development of AD, searching for a...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2019.102935

    authors: Jeyakumar M,Sathya S,Gandhi S,Tharra P,Suryanarayanan V,Singh SK,Baire B,Pandima Devi K

    更新日期:2019-07-01 00:00:00

  • Antitrypanosomal activity of epi-polygodial from Drimys brasiliensis and its effects in cellular membrane models at the air-water interface.

    abstract::Epi-polygodial, a drimane sesquiterpene was isolated from Drimys brasiliensis (Winteraceae). This compound demonstrated high parasite selectivity towards Trypanosoma cruzi trypomastigotes (IC50 = 5.01 μM) with a selectivity index higher than 40. These results were correlated with the effects observed when this compoun...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2018.11.048

    authors: Gonçalves GEG,Morais TR,Gomes KS,Costa-Silva TA,Tempone AG,Lago JHG,Caseli L

    更新日期:2019-03-01 00:00:00

  • Exploration of aroyl/heteroaroyl iminothiazolines featuring 2,4,5-trichlorophenyl moiety as a new class of potent, selective, and in vitro efficacious glucosidase inhibitors.

    abstract::A series of iminothiazolines (4a-j) featuring 2,4,5-trichlorophenyl moiety and aroyl/heteroaroyl substituents has been prepared from readily accessible thioureas. In-vitro screening against glucosidase enzymes showed highly specific inhibition of α-glucosidase with a marked dependence of the potency upon the nature of...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2017.07.012

    authors: Kazmi M,Zaib S,Amjad ST,Khan I,Ibrar A,Saeed A,Iqbal J

    更新日期:2017-10-01 00:00:00

  • Synthesis and evaluation of antioxidant and antiproliferative activity of 2-arylbenzimidazoles.

    abstract::Three series of arylbenzimidazole derivatives 3-40, 45 have been simply synthesized and tested for their antioxidant capacity. The 2-arylbenzimidazoles were tested against various radicals by the DPPH, FRAP and ORAC tests and showed different activity profiles. It has been observed that the number and position of the ...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2019.103396

    authors: Baldisserotto A,Demurtas M,Lampronti I,Tacchini M,Moi D,Balboni G,Pacifico S,Vertuani S,Manfredini S,Onnis V

    更新日期:2020-01-01 00:00:00

  • Separation and configurational assignment of stereoisomeric phenalenones from the marine mangrove-derived fungus Penicillium herquei MA-370.

    abstract::Eight phenalenone derivatives, including four new compounds, aceneoherqueinones A and B (1 and 2), (+)-aceatrovenetinone A (3a), and (+)-aceatrovenetinone B (3d), along with four known congeners, (-)-aceatrovenetinone A (3b), (-)-aceatrovenetinone B (3c), (-)-scleroderolide (4a), and (+)-scleroderolide (4b), were char...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2020.104477

    authors: Yang SQ,Mándi A,Li XM,Liu H,Li X,Balázs Király S,Kurtán T,Wang BG

    更新日期:2021-01-01 00:00:00

  • Design, synthesis and biological evaluation of novel 1,2,3-triazole linked coumarinopyrazole conjugates as potent anticholinesterase, anti-5-lipoxygenase, anti-tyrosinase and anti-cancer agents.

    abstract::A series of new 1,2,3-triazole linked coumarinopyrazole conjugates 4a-e and 5a-e have been synthesized via the Copper(I)-catalysed Alkyne-Azide Cycloaddition (CuAAC). Going through the reaction of compound 2 with the 3-propargyl bromide gave a mixture of propargylated regioisomers 3 + 3' used as a dipolarophile to acc...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2018.06.005

    authors: Chekir S,Debbabi M,Regazzetti A,Dargère D,Laprévote O,Ben Jannet H,Gharbi R

    更新日期:2018-10-01 00:00:00

  • DNA binding studies of novel diazatruxenones analogs as potential anticancer agents: Synthesis, antitumor investigation, DNA binding, SAR and molecular modeling calculation.

    abstract::A series of polycyclic skeleton of truxene and triazatruxene analogs has been synthesized and evaluated for antitumor and DNA binding activities. The synthesized structures were confirmed by different spectroscopic techniques such as IR, 1HNMR, 13CNMR, and mass spectroscopy. The antitumor screening was performed adopt...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2020.104323

    authors: El Sayed MT,Shabaan SN,Sarhan AE,El-Messery SM,El-Sayed SM,Hassan GS

    更新日期:2020-11-01 00:00:00

  • Taxumarienes A-G, seven new α-glucosidase inhibitory taxane-diterpenoids from the leaves of Taxus mairei.

    abstract::Seven new taxane diterpenoids taxumarienes A-G (1-7) were isolated from the leaves of Taxus mairei, along with seven known analogous (8-14). The structures of the new compounds were elucidated based on the analysis of NMR and MS spectroscopy. All isolates were evaluated for their α-glucosidase inhibitory activities. A...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2019.103400

    authors: Chen K,Liu XQ,Wang WL,Luo JG,Kong LY

    更新日期:2020-01-01 00:00:00

  • Pesimquinolones I-S, eleven new quinolone alkaloids produced by Penicillium simplicissimum and their inhibitory activity on NO production.

    abstract::Eleven undescribed quinolone alkaloids, pesimquinolones I-S (1-4 and 6-12), as well as eleven known congeners (5 and 13-22), were isolated from the solid culture broth of the fungus Penicillium simplicissimum. Their chemical structures with absolute configurations were established by a combination of NMR spectroscopy,...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2021.104635

    authors: Dai C,Li X,Zhang K,Li XN,Wang W,Zang Y,Chen X,Li Q,Wei M,Chen C,Zhu H,Zhang Y

    更新日期:2021-01-08 00:00:00

  • Surprising duplex stabilisation upon mismatch introduction within triply modified duplexes.

    abstract::Three different modified phosphoramidite nucleoside building blocks equipped with additional protected imidazole, masked alcohol and masked carboxylate functionality are synthesized and incorporated into oligonucleotides. Based on the serine-protease active site model, doubly and triply modified duplexes are created a...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2010.01.002

    authors: Catry MA,Gheerardijn V,Madder A

    更新日期:2010-06-01 00:00:00

  • Kinetic Isotope Effects and Stereochemical Studies on a Ribonuclease Model: Hydrolysis Reactions of Uridine 3'-Nitrophenyl Phosphate.

    abstract::The reactions of a ribonuclease model substrate, the compound uridine-3'-p-nitrophenyl phosphate, have been examined using heavy-atom isotope effects and stereochemical analysis. The cyclization of this compound is subject to catalysis by general base (by imidazole buffer), specific base (by carbonate buffer), and by ...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1006/bioo.2000.1170

    authors: Hengge AC,Bruzik KS,Tobin AE,Cleland WW,Tsai MD

    更新日期:2000-06-01 00:00:00

  • Novel coumarin-pyridazine hybrids as selective MAO-B inhibitors for the Parkinson's disease therapy.

    abstract::The 3-pyridazinylcoumarin scaffold was previously reported as an efficient core for the discovery of reversible and selective inhibitors of MAO-B, a validated drug target for PD therapy which also plays an important role in the AD progress. Looking for its structural optimization, novel compounds of hybrid structure c...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2020.104203

    authors: Rodríguez-Enríquez F,Costas-Lago MC,Besada P,Alonso-Pena M,Torres-Terán I,Viña D,Fontenla JÁ,Sturlese M,Moro S,Quezada E,Terán C

    更新日期:2020-11-01 00:00:00

  • Enantiomeric 8-O-4'-type neolignans from Crataegus pinnatifida exhibit cytotoxic effect via apoptosis and autophagy in Hep3B cells.

    abstract::Crataegus pinnatifida has been famous for its nutritional purpose. However, systematic investigation on the bioactive constituents is still lacking, although this fruit has been reported for its cytotoxic effect before. In this study, two pairs of new lignan enantiomers (1a/1b, 2a/2b), which isolated using chiral chro...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2020.104267

    authors: Shang XY,Guo R,Yu XQ,Lin B,Huang XX,Yao GD,Song SJ

    更新日期:2020-11-01 00:00:00

  • Design, synthesis and anticancer evaluation of thieno[2,3-d]pyrimidine derivatives as dual EGFR/HER2 inhibitors and apoptosis inducers.

    abstract::Deregulation of many kinases is directly linked to cancer development and the tyrosine kinase family is one of the most important targets in current cancer therapy regimens. In this study, we have designed and synthesized a series of thieno[2,3-d]pyrimidine derivatives as an EGFR and HER2 tyrosine kinase inhibitors. A...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2019.102944

    authors: Elmetwally SA,Saied KF,Eissa IH,Elkaeed EB

    更新日期:2019-07-01 00:00:00

  • Design, synthesis, and biological evaluation of novel dual FFA1 (GPR40)/PPARδ agonists as potential anti-diabetic agents.

    abstract::The free fatty acid receptor 1 (FFA1) and peroxisome proliferator-activated receptor δ (PPARδ) were considered as potential anti-diabetic targets, and the dual FFA1/PPARδ agonists might provide synergistic effect in insulin secretion and sensibility. Herein, we further develop dual agonists by screening 7 series of he...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2019.103254

    authors: Li Z,Hu L,Wang X,Zhou Z,Deng L,Xu Y,Zhang L

    更新日期:2019-11-01 00:00:00

  • Bioactive flavonoid dimers from Chinese dragon's blood, the red resin of Dracaena cochinchinensis.

    abstract::Seven flavonoid dimers, biflavocochins A-G, together with six known compounds were isolated from the red resins of Dracaena cochinchinensis (Chinese dragon's blood). Their structures were elucidated based on extensive spectroscopic analysis. The absolute configurations of 1-7 was assigned by experimental and quantum c...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2020.103659

    authors: Lang GZ,Li CJ,Gaohu TY,Li C,Ma J,Yang JZ,Zhou TT,Yuan YH,Ye F,Wei JH,Zhang DM

    更新日期:2020-04-01 00:00:00

  • Ellagitannin and flavonoid constituents from Agrimonia pilosa Ledeb. with their protein tyrosine phosphatase and acetylcholinesterase inhibitory activities.

    abstract::A new ellagitannin, agritannin (1), a new flavone glycoside, agriflavone (2), and another flavone glycoside with spectroscopic data reported for the first time, kaempferol-3-O-[(S)-3-hydroxy-3-methylglutaryl (1→6)]-β-d-glucoside (3), along with 16 known compounds were isolated from the aerial parts of Agrimonia pilosa...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2017.04.017

    authors: Nguyen DH,Seo UM,Zhao BT,Le DD,Seong SH,Choi JS,Min BS,Woo MH

    更新日期:2017-06-01 00:00:00

  • The green synthesis and molecular docking of novel N-substituted rhodanines as effective inhibitors for carbonic anhydrase and acetylcholinesterase enzymes.

    abstract::Recently, inhibition effects of enzymes such as acetylcholinesterase (AChE) and carbonic anhydrase (CA) has appeared as a promising approach for pharmacological intervention in a variety of disorders such as epilepsy, Alzheimer's disease and obesity. For this purpose, novel N-substituted rhodanine derivatives (RhAs) w...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2019.103096

    authors: Bayindir S,Caglayan C,Karaman M,Gülcin İ

    更新日期:2019-09-01 00:00:00

  • Synthesis and antiproliferative activity of new 2-glyco-3-nitro-2H-chromenes.

    abstract::3-nitro-2H-chromenes and derivatives are compounds with diverse biological activity, among them, new 2-glyco-3-nitro-2H-chromenes have been prepared by one-pot oxa-Michael-Henry-dehydration reactions between carbohydrate-derived nitroalkenes and several salicylaldehydes, using a minimal amount of solvent and DBU as ca...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2019.03.016

    authors: Luque-Agudo V,Albarrán-Velo J,Light ME,Padrón JM,Román E,Serrano JA,Gil MV

    更新日期:2019-06-01 00:00:00

  • Bioactive polyoxygenated seco-cyclohexenes from Artabotrys hongkongensis.

    abstract::Six new polyoxygenated seco-cyclohexenes, artahongkongenes A-F (1-6), together with six known analogues (7-12) were isolated from the stems and leaves of Artabotrys hongkongensis. Their structures were elucidated by extensive spectroscopic methods. All new compounds were evaluated for their cytotoxicities against five...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2017.12.011

    authors: Liu YP,Tang JY,Hua Y,Lai L,Luo XL,Zhang ZJ,Yin WQ,Chen GY,Fu YH

    更新日期:2018-02-01 00:00:00

  • Design, synthesis and evaluation of some 1,6-disubstituted-1H-benzo[d]imidazoles derivatives targeted PI3K as anticancer agents.

    abstract::Phosphatidylinositol 3-kinase (PI3K) pathway regulates various cellular processes, such as proliferation, growth, autophagy and apoptosis. Class I PI3K is frequently mutated and overexpressed in a lot of human cancers and PI3K was considered as a target for therapeutic treatment of cancer. In this study, we designed a...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2019.103283

    authors: Ding HW,Yu L,Bai MX,Qin XC,Song MT,Zhao QC

    更新日期:2019-12-01 00:00:00

  • Auspicious role of the steroidal heterocyclic derivatives as a platform for anti-cancer drugs.

    abstract::Steroids are polycyclic compounds that have a wide range of biological activities. They are bio-synthesized from cholesterol through a series of enzyme-mediated transformations, so they are highly lipophilic and readily enter most cells to interact with intracellular receptors, making them ideal vehicles for targeting...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.bioorg.2017.06.006

    authors: Tantawy MA,Nafie MS,Elmegeed GA,Ali IAI

    更新日期:2017-08-01 00:00:00

  • Triazinoindole analogs as potent inhibitors of α-glucosidase: synthesis, biological evaluation and molecular docking studies.

    abstract::A new series of triazinoindole analogs 1-11 were synthesized, characterized by EI-MS and (1)H NMR, evaluated for α-glucosidase inhibitory potential. All eleven (11) analogs showed different range of α-glucosidase inhibitory potential with IC50 value ranging between 2.46±0.008 and 312.79±0.06 μM when compared with the ...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2014.12.001

    authors: Rahim F,Ullah K,Ullah H,Wadood A,Taha M,Ur Rehman A,uddin I,Ashraf M,Shaukat A,Rehman W,Hussain S,Khan KM

    更新日期:2015-02-01 00:00:00

  • Expeditious and eco-friendly synthesis of new multifunctionalized pyrrole derivatives and evaluation of their antioxidant property.

    abstract::Diminution of oxidative stress-mediated diseases is an essential pharmaceutical objective in modern biomedical research. The present work stresses upon the efficient and eco-friendly synthesis of an array of novel diversely functionalized pyrrole derivatives which are found to be antioxidants with reactive oxygen spec...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2020.103734

    authors: Kundu T,Pramanik A

    更新日期:2020-05-01 00:00:00

  • Esterification of all four monoribonucleotides with acetyl-D-L-valine proceeds with a preference for the D-isomer but the D/L ratio in the products declines as a function of the hydrophobicity of the nucleotide.

    abstract::We recently reported that esterification of 5'-AMP with N-acetyl amino acids proceeds with a preference for D-amino acids, and the D/L ratio in products declines as the hydrophobicity of the amino acid declines. Using one amino acid, Ac-Val, we now show that esterification of all four nucleotides proceeds with a pref...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/0045-2068(92)90019-y

    authors: Wickramasinghe NS,Lacey JC Jr

    更新日期:1992-01-01 00:00:00

  • Discovery of isoalloxazine derivatives as a new class of potential anti-Alzheimer agents and their synthesis.

    abstract::This article describes discovery of a novel and new class of cholinesterase inhibitors as potential therapeutics for Alzheimer's disease. A series of novel isoalloxazine derivatives were synthesized and biologically evaluated for their potential inhibitory outcome for both acetylcholinesterase (AChE) and butyrylcholin...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2015.05.005

    authors: Kanhed AM,Sinha A,Machhi J,Tripathi A,Parikh ZS,Pillai PP,Giridhar R,Yadav MR

    更新日期:2015-08-01 00:00:00