Chemical characterization of cytotoxic indole acetic acid derivative from mulberry fruit (Morus alba L.) against human cervical cancer.

Abstract:

:The fruit of the white mulberry tree (Morus alba L.) is a multiple fruit with a sweet flavor commonly consumed around the world. Chemical investigation of the fruits led to the isolation of two indole acetic acid derivatives (1 -2) including a new compound, which turned out to be an isolation artifact, 3S-(β-D-glucopyranosyloxy)-2,3-dihydro-2-oxo-1H-indole-3-acetic acid butyl ester (1), along with five known compounds (3 -7). Compounds 2 and 7 were newly identified from mulberry fruit. The new isolation artifact (1) exhibited cytotoxic effect on human cervical cancer Hela cells in a dose-dependent manner. Compound 1 activated caspase-8, caspase-9, and caspase-3, followed by cleavage of PARP, a substrate of caspase-3, in a dose-dependent manner. Simultaneous alterations in protein expression of mitochondrial factors Bax, BID and Bcl-2 were also observed. A comparison between compounds 1 and 2 led to a structure-activity relationship analysis of the cytotoxic effect. These results suggest that compound 1 could be beneficial in human cervical cancer treatment, and provide a theoretical basis for further application of compound 1.

journal_name

Bioorg Chem

journal_title

Bioorganic chemistry

authors

Yu JS,Lee D,Lee SR,Lee JW,Choi CI,Jang TS,Kang KS,Kim KH

doi

10.1016/j.bioorg.2017.10.015

subject

Has Abstract

pub_date

2018-02-01 00:00:00

pages

28-36

eissn

0045-2068

issn

1090-2120

pii

S0045-2068(17)30571-0

journal_volume

76

pub_type

杂志文章
  • Synthesis of Mitomycin C and decarbamoylmitomycin C N6 deoxyadenosine-adducts.

    abstract::Mitomycin C (MC), an anti-cancer drug, and its analog, decarbamoylmitomycin C (DMC), are DNA-alkylating agents. MC is currently used in the clinics and its cytotoxicity is mainly due to its ability to form Interstrand Crosslinks (ICLs) which impede DNA replication and, thereby, block cancer cells proliferation. Howeve...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2019.103280

    authors: Zheng M,Hwang S,Snyder T,Aquilina J,Proni G,Paz MM,Pradhan P,Cheng SY,Champeil E

    更新日期:2019-11-01 00:00:00

  • Discovery of novel cathepsin inhibitors with potent anti-metastatic effects in breast cancer cells.

    abstract::It is still challenging to determine the potential targets of natural products, which is essential for further drug research and development. Due to its novel mechanism of action of inducing autophagy effects in breast cancer cells, asperphenamate has received our considerable attention. However, its unknown target in...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2018.09.029

    authors: Yuan L,Sheng L,He W,Zou C,Hu B,Liu J,Ge W,Liu Y,Wang J,Ma E

    更新日期:2018-12-01 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

  • Mycothiol: a promising antitubercular target.

    abstract::Tuberculosis (TB) is the world's second commonest cause of death next to HIV/AIDS. The increasing emergence of multi drug resistance and the recalcitrant nature of persistent infections pose an additional challenge for the treatment of TB. Due to the development of resistance to conventional antibiotics there is a nee...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.bioorg.2013.11.004

    authors: Nilewar SS,Kathiravan MK

    更新日期:2014-02-01 00:00:00

  • QM/MM study of the reaction mechanism of Cl-cis,cis-muconate with muconate lactonizing enzyme.

    abstract::The lactonization process of Cl-cis,cis-muconate catalyzed by anti-muconate lactonizing enzyme (anti-MLE) was studied theoretically with the aid of a combined quantum mechanics/molecular mechanics (QM/MM) approach. Two elementary processes steps involved in the lactanization process were investigated. The calculated e...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2018.05.007

    authors: Zhu L,Tang X,Li Y,Zhang R,Wang J,Zhang Q,Wang W

    更新日期:2018-10-01 00:00:00

  • Synthesis and characterization of CAPE derivatives as xanthine oxidase inhibitors with radical scavenging properties.

    abstract::Inhibitors of the enzyme xanthine oxidase (XO) with radical scavenging properties hold promise as novel agents against reperfusion injuries after ischemic events. By suppressing the formation of damaging reactive oxygen species (ROS) by XO or scavenging ROS from other sources, these compounds may prevent a buildup of ...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2019.02.049

    authors: Choi W,Villegas V,Istre H,Heppler B,Gonzalez N,Brusman N,Snider L,Hogle E,Tucker J,Oñate A,Oñate S,Ma L,Paula S

    更新日期:2019-05-01 00:00:00

  • Identification of 5-benzylidene-2-phenylthiazolones as potent PRMT5 inhibitors by virtual screening, structural optimization and biological evaluations.

    abstract::Protein arginine methyltransferase 5 (PRMT5) is an epigenetics related enzyme that has been validated as an important therapeutic target for glioblastoma and mantel cell lymphoma. In the present study, 11 novel PRMT5 inhibitors with 5-benzylidene-2-phenylthiazolone scaffold were identified by molecular docking-based v...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2018.08.021

    authors: Zhu K,Tao H,Song JL,Jin L,Zhang Y,Liu J,Chen Z,Jiang CS,Luo C,Zhang H

    更新日期:2018-12-01 00:00:00

  • Structural elucidation and anti-neuroinflammatory activities of lignans from the testas of Vernicia montana.

    abstract::Vernicia montana Lour. (tung tree) is an oil-producing plant with multiple uses, especially with its great potential in biodiesel production, which was a small Asian tree of the spurge family (Euphorbiaceae) with big economic values. However, studies on small molecular compositions of V. montana are limited. As a resu...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2020.103690

    authors: Zhou D,Li Y,Chen G,Yang Y,Mi Y,Lin B,Li W,Hou Y,Li N

    更新日期:2020-04-01 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

  • Antimalarial activity of HIV-1 protease inhibitor in chromone series.

    abstract::Increasing parasite resistance to nearly all available antimalarial drugs becomes a serious problem to human health and necessitates the need to continue the search for new effective drugs. Recent studies have shown that clinically utilized HIV-1 protease (HIV-1 PR) inhibitors can inhibit the in vitro and in vivo grow...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2014.10.006

    authors: Lerdsirisuk P,Maicheen C,Ungwitayatorn J

    更新日期:2014-12-01 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

  • Tacrine-hydroxamate derivatives as multitarget-directed ligands for the treatment of Alzheimer's disease: Design, synthesis, and biological evaluation.

    abstract::In order to develop multitarget-directed ligands as potential treatments for Alzheimer's disease, twenty-eight new tacrine-hydroxamate derivatives were designed, synthesized, and biologically evaluated. As expected, most of the compounds exhibited inhibitory activities against cholinesterases (ChEs) and histone deacet...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2020.103721

    authors: Xu A,He F,Zhang X,Li X,Ran Y,Wei C,James Chou C,Zhang R,Wu J

    更新日期:2020-05-01 00:00:00

  • Synthesis and molecular docking study of new benzofuran and furo[3,2-g]chromone-based cytotoxic agents against breast cancer and p38α MAP kinase inhibitors.

    abstract::This study deals with synthesis of a new set of benzofuran and 5H-furo[3,2-g]chromone linked various heterocyclic functionalities using concise synthetic approaches aiming to gain new antiproliferative candidates against MCF-7 breast cancer cells of p38α MAP kinase inhibiting activity. The biological data proved the s...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2017.12.029

    authors: Amin KM,Syam YM,Anwar MM,Ali HI,Abdel-Ghani TM,Serry AM

    更新日期:2018-02-01 00:00:00

  • Synthesis of new 3-phenylquinazolin-4(3H)-one derivatives as potent antibacterial agents effective against methicillin- and vancomycin-resistant Staphylococcus aureus (MRSA and VRSA).

    abstract::Occurrence of infections due to the drug resistant Staphylococcus aureus is on rise necessitating the need for rapid development of new antibacterial agents. In our present work, a series of new 3-phenylquinazolin-4(3H)-one derivatives were designed, synthesized and evaluated for their antibacterial activity against E...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2018.08.012

    authors: Gatadi S,Gour J,Kaul G,Shukla M,Dasgupta A,Akunuri R,Tripathi R,Madhavi YV,Chopra S,Nanduri S

    更新日期:2018-12-01 00:00:00

  • Heterocyclic periphery in the design of carbonic anhydrase inhibitors: 1,2,4-Oxadiazol-5-yl benzenesulfonamides as potent and selective inhibitors of cytosolic hCA II and membrane-bound hCA IX isoforms.

    abstract::A series of novel aromatic primary sulfonamides decorated with diversely substituted 1,2,4-oxadiazole periphery groups has been prepared using a parallel chemistry approach. The compounds displayed a potent inhibition of cytosolic hCA II and membrane-bound hCA IX isoforms. Due to a different cellular localization of t...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2017.10.005

    authors: Krasavin M,Shetnev A,Sharonova T,Baykov S,Tuccinardi T,Kalinin S,Angeli A,Supuran CT

    更新日期:2018-02-01 00:00:00

  • Design, synthesis, molecular modeling, in vivo studies and anticancer activity evaluation of new phthalazine derivatives as potential DNA intercalators and topoisomerase II inhibitors.

    abstract::Herein we report the design and synthesis of a new series of phthalazine derivatives as Topo II inhibitors and DNA intercalators. The synthesized compounds were in vitro evaluated for their cytotoxic activities against HepG-2, MCF-7 and HCT-116 cell lines. Additionally, Topo II inhibitory activity and DNA intercalatin...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2020.104233

    authors: El-Helby AA,Sakr H,Ayyad RR,Mahdy HA,Khalifa MM,Belal A,Rashed M,El-Sharkawy A,Metwaly AM,Elhendawy MA,Radwan MM,ElSohly MA,Eissa IH

    更新日期:2020-10-01 00:00:00

  • Introduction of amino moiety enhances the inhibitory potency of 1-tetralone chalcone derivatives against LPS-stimulated reactive oxygen species production in RAW 264.7 macrophages.

    abstract::The design and synthesis of a series of thirty-two halogenated 1-tetralone or 6-amino-1-tetralone chalcone derivatives was achieved by the Claisen-Schmidt condensation reaction and were evaluated for their inhibitory effects against ROS production in LPS-stimulated RAW 264.7 macrophages. It was observed that the intro...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2019.03.055

    authors: Katila P,Shrestha A,Shrestha A,Shrestha R,Park PH,Lee ES

    更新日期:2019-06-01 00:00:00

  • A competent synthesis and efficient anti-inflammatory responses of isatinimino acridinedione moiety via suppression of in vivo NF-κB, COX-2 and iNOS signaling.

    abstract::A potent Nonsterodial Anti-inflammatory Drug (NSAID) candidates has been conceived and built by an assembly of a hydrophilic, fluorescent and COX-2 inhibiting units in the same molecule. The isatinimino-acridinedione core (TM-7) was achieved in a simple three step synthetic procedure viz (i) a multicomponent reaction ...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2019.103047

    authors: Periyasami G,Antonisamy P,Perumal K,Stalin A,Rahaman M,Alothman AA

    更新日期:2019-09-01 00:00:00

  • Heterocyclic cellular lipid peroxidation inhibitors inspired by the marine antioxidant barettin.

    abstract::The marine environment remains a rich source for the discovery and development of novel bioactive compounds. The present paper describes the design, synthesis and biological evaluation of a library of small molecule heterocyclic mimetics of the marine 2,5-diketopiperazine barettin which is a powerful natural antioxida...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2018.11.024

    authors: Labrière C,Andersen JH,Albrigtsen M,Hansen JH,Svenson J

    更新日期:2019-03-01 00:00:00

  • Differential metabolism of diastereoisomeric diterpenes by Preussia minima, found as endophytic fungus in Cupressus lusitanica.

    abstract::The plant diastereoisomeric diterpenes ent-pimara-8(14)-15-dien-19-oic acid, obtained from Viguiera arenaria, and isopimara-8(14)-15-dien-18-oic acid, isolated from Cupressus lusitanica, were distinctly functionalized by the enzymes produced in whole cell cultures of the fungus Preussia minima, isolated from surface s...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2018.04.003

    authors: Ud Din Z,de Medeiros LS,Abreu LM,Pfenning LH,Lopes Jymeni DB,Rodrigues-Filho E

    更新日期:2018-08-01 00:00:00

  • Evaluation of 4-thiazolidinone derivatives as potential reverse transcriptase inhibitors against HIV-1 drug resistant strains.

    abstract::Rapid emergence of drug resistance is crucial in management of HIV infection limiting implementation of efficacious drugs in the ART regimen. Designing new molecules against HIV drug resistant strains is utmost essential. Based on the anti-HIV-1 activity, we selected four 4-thiazolidinone derivatives (S009-1908, S009-...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2017.02.007

    authors: Suryawanshi R,Jadhav S,Makwana N,Desai D,Chaturbhuj D,Sonawani A,Idicula-Thomas S,Murugesan V,Katti SB,Tripathy S,Paranjape R,Kulkarni S

    更新日期:2017-04-01 00:00:00

  • Enantiodiscrimination of bilirubin-IXalpha enantiomers in biomembrane models: has chirality a role in bilirubin toxicity?

    abstract::Simple biomembrane models, namely micellar aggregates formed by enantiopure sodium N-acylprolinates, are able to convert the racemic mixture of bilirubin-IXalpha into an enantiomerically enriched mixture, thus suggesting a possible role of chirality in bilirubin toxicity due to the perturbation of neuron membrane dyna...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2008.05.001

    authors: Ceccacci F,Giansanti L,Mortera SL,Mancini G,Sorrenti A,Villani C

    更新日期:2008-10-01 00:00:00

  • Five new compounds from Hosta plantaginea flowers and their anti-inflammatory activities.

    abstract::Five new compounds hostines A-E (1-5), together with eighteen known compounds (6-23), were obtained from the flowers of Hosta plantaginea (Lam.) Aschers, a traditional folk herbal medicine widely used in Mongolian. The structures of the undescribed compounds were determined by using detailed spectroscopic (1D/2D NMR) ...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2019.103494

    authors: Zhang Y,Liu J,Wang M,Sun C,Li X

    更新日期:2020-01-01 00:00:00

  • Antimycobacterial activity of azepanobetulin and its derivative: In vitro, in vivo, ADMET and docking studies.

    abstract::The antimycobacterial investigation of azepanobetulin and its amide derivative was performed. Both compounds showed increased in vitro antibacterial activity on the H37Rv MTB strain in aerobic and anaerobic conditions. Basing on differences between MIC and IC50 values a predominant bactericidal effect for amide in con...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2020.104209

    authors: Kazakova O,Lopatina T,Giniyatullina G,Mioc M,Soica C

    更新日期:2020-11-01 00:00:00

  • Preparative scale application of Mucor circinelloides ene-reductase and alcohol dehydrogenase activity for the asymmetric bioreduction of α,β-unsaturated γ-ketophosphonates.

    abstract::The fungus Mucor circinelloides exhibits high potential for green chemistry and technological applications. Recently M. circinelloides, which so far was considered mainly as a platform for biodiesel production, was found to exhibit high ene-reductase activity. In our current research we applied this promising microorg...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2019.103548

    authors: Janicki I,Kiełbasiński P,Szeląg J,Głębski A,Szczęsna-Antczak M

    更新日期:2020-03-01 00:00:00

  • From orexin receptor agonist YNT-185 to novel antagonists with drug-like properties for the treatment of insomnia.

    abstract::YNT-185 is the first known small molecule acting as orexin 2 receptor (OX2R) agonist with implication to narcolepsy treatment, served as a template scaffold in generating a small set of seven compounds with predictive affinity to OX2R. The design of the new small molecules was driven mostly by improving physicochemica...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2020.104179

    authors: Mezeiova E,Janockova J,Konecny J,Kobrlova T,Benkova M,Dolezal R,Prchal L,Karasova-Zdarova J,Soukup O,Korabecny J

    更新日期:2020-10-01 00:00:00

  • Design, synthesis, in vitro and in silico investigation of aldose reductase inhibitory effects of new thiazole-based compounds.

    abstract::Aldose reductase (AR) catalyzes the NADPH-dependent reduction of glucose to sorbitol in the polyol pathway, which plays an important role in the development of diabetic complications including cataract, retinopathy, nephropathy, and neuropathy. AR has been considered as an important target to heal these long-term diab...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2020.104110

    authors: Sever B,Altıntop MD,Demir Y,Akalın Çiftçi G,Beydemir Ş,Özdemir A

    更新日期:2020-09-01 00:00:00

  • 1,2,3-Triazole-based kojic acid analogs as potent tyrosinase inhibitors: Design, synthesis and biological evaluation.

    abstract::A series of kojic acid-derived compounds 6a-p bearing aryloxymethyl-1H-1,2,3-triazol-1-yl moiety were designed by modifying primary alcoholic group of kojic acid as tyrosinase inhibitors. The target compounds 6a-p were synthesized via click reaction. All compounds showed very potent anti-tyrosinase activity (IC50s = 0...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2018.10.069

    authors: Ashooriha M,Khoshneviszadeh M,Khoshneviszadeh M,Moradi SE,Rafiei A,Kardan M,Emami S

    更新日期:2019-02-01 00:00:00

  • Structure-activity relationships and molecular docking of thirteen synthesized flavonoids as horseradish peroxidase inhibitors.

    abstract::For the first time, the structure-activity relationships of thirteen synthesized flavonoids have been investigated by evaluating their ability to modulate horseradish peroxidase (HRP) catalytic activity. Indeed, a modified spectrophotometrically method was carried out and optimized using 4-methylcatechol (4-MC) as per...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2017.08.001

    authors: Mahfoudi R,Djeridane A,Benarous K,Gaydou EM,Yousfi M

    更新日期:2017-10-01 00:00:00

  • 3, 9-di-O-substituted coumestrols incorporating basic amine side chains act as novel apoptosis inducers with improved pharmacological selectivity.

    abstract::There is much interest in the use of phytoestrogens such as coumestrol in breast cancer intervention due to their antiestrogenic activity and multiple modes of tumor cell death. However, the clear beneficial effects of naturally occurring estrogen mimetic coumestrol remain controversial due to experimental evidence th...

    journal_title:Bioorganic chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bioorg.2018.12.024

    authors: Luo G,Tang Z,Li X,Hou Q,Chen Y,Lao K,Xiang H

    更新日期:2019-04-01 00:00:00