Literature DB >> 33445521

New Deoxyisoaustamide Derivatives from the Coral-Derived Fungus Penicillium dimorphosporum KMM 4689.

Olesya I Zhuravleva1,2, Alexandr S Antonov1, Vo Thi Dieu Trang3, Mikhail V Pivkin1, Yuliya V Khudyakova1, Vladimir A Denisenko1, Roman S Popov1, Natalya Y Kim1, Ekaterina A Yurchenko1, Andrey V Gerasimenko4, Anatoly A Udovenko4, Gunhild von Amsberg5,6, Sergey A Dyshlovoy1,2,5,6, Shamil S Afiyatullov1.   

Abstract

Seven new deoxyisoaustamide derivatives (1-7) together with known compounds (8-10) were isolated from the coral-derived fungus Penicillium dimorphosporum KMM 4689. Their structures were established using spectroscopic methods, X-ray diffraction analysis and by comparison with related known compounds. The absolute configurations of some alkaloids were determined based on CD and NOESY data as well as biogenetic considerations. The cytotoxic and neuroprotective activities of some of the isolated compounds were examined and structure-activity relationships were pointed out. New deoxyisoaustamides 4-6 at concentration of 1 µM revealed a statistical increase of PQ(paraquat)-treated Neuro-2a cell viability by 30-39%.

Entities:  

Keywords:  Penicillium dimorphosporum; deoxyisoaustamide; neuroprotective activity; paraquat; prenylated indole diketopiperazines; secondary metabolites

Mesh:

Substances:

Year:  2021        PMID: 33445521      PMCID: PMC7826743          DOI: 10.3390/md19010032

Source DB:  PubMed          Journal:  Mar Drugs        ISSN: 1660-3397            Impact factor:   5.118


  15 in total

Review 1.  2,5-diketopiperazines as neuroprotective agents.

Authors:  C Cornacchia; I Cacciatore; L Baldassarre; A Mollica; F Feliciani; F Pinnen
Journal:  Mini Rev Med Chem       Date:  2012-01       Impact factor: 3.862

2.  Notoamides F-K, prenylated indole alkaloids isolated from a marine-derived Aspergillus sp.

Authors:  Sachiko Tsukamoto; Hikaru Kato; Masayuki Samizo; Yuka Nojiri; Hiroyuki Onuki; Hiroshi Hirota; Tomihisa Ohta
Journal:  J Nat Prod       Date:  2008-12       Impact factor: 4.050

3.  Effect of resveratrol and tetracycline on the subacute paraquat toxicity in mice.

Authors:  R M Satpute; P P Pawar; S Puttewar; S D Sawale; P D Ambhore
Journal:  Hum Exp Toxicol       Date:  2017-01-16       Impact factor: 2.903

4.  Prenylated indole diketopiperazines from the marine-derived fungus Aspergillus versicolor.

Authors:  Jixing Peng; Huquan Gao; Jing Li; Jing Ai; Meiyu Geng; Guojian Zhang; Tianjiao Zhu; Qianqun Gu; Dehai Li
Journal:  J Org Chem       Date:  2014-08-11       Impact factor: 4.354

5.  A short synthetic route to (+)-austamide, (+)-deoxyisoaustamide, and (+)-hydratoaustamide from a common precursor by a novel palladium-mediated indole --> dihydroindoloazocine cyclization.

Authors:  Phil S Baran; E J Corey
Journal:  J Am Chem Soc       Date:  2002-07-10       Impact factor: 15.419

6.  Cytotoxic alkaloids and antibiotic nordammarane triterpenoids from the marine-derived fungus Aspergillus sydowi.

Authors:  Min Zhang; Wen-Liang Wang; Yu-Chun Fang; Tian-Jiao Zhu; Qian-Qun Gu; Wei-Ming Zhu
Journal:  J Nat Prod       Date:  2008-05-28       Impact factor: 4.050

7.  Neuroprotection of Neuro2a cells and the cytokine suppressive and anti-inflammatory mode of action of resveratrol in activated RAW264.7 macrophages and C8-B4 microglia.

Authors:  Nicole Steiner; Rachelle Balez; Niloo Karunaweera; Joanne M Lind; Gerald Münch; Lezanne Ooi
Journal:  Neurochem Int       Date:  2015-10-29       Impact factor: 3.921

8.  SHELXT - integrated space-group and crystal-structure determination.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A Found Adv       Date:  2015-01-01       Impact factor: 2.290

9.  Crystal structure refinement with SHELXL.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr C Struct Chem       Date:  2015-01-01       Impact factor: 1.172

10.  Successful Targeting of the Warburg Effect in Prostate Cancer by Glucose-Conjugated 1,4-Naphthoquinones.

Authors:  Sergey A Dyshlovoy; Dmitry N Pelageev; Jessica Hauschild; Ksenia L Borisova; Moritz Kaune; Christoph Krisp; Simone Venz; Yurii E Sabutskii; Ekaterina A Khmelevskaya; Tobias Busenbender; Vladimir A Denisenko; Natalia D Pokhilo; Lyubov N Atopkina; Markus Graefen; Hartmut Schlüter; Valentin A Stonik; Carsten Bokemeyer; Victor Ph Anufriev; Gunhild von Amsberg
Journal:  Cancers (Basel)       Date:  2019-10-30       Impact factor: 6.639

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  4 in total

1.  Cytoprotective Activity of p-Terphenyl Polyketides and Flavuside B from Marine-Derived Fungi against Oxidative Stress in Neuro-2a Cells.

Authors:  Ekaterina A Yurchenko; Ekaterina S Menchinskaya; Evgeny A Pislyagin; Ekaterina A Chingizova; Elena V Girich; Anton N Yurchenko; Dmitry L Aminin; Valery V Mikhailov
Journal:  Molecules       Date:  2021-06-13       Impact factor: 4.411

Review 2.  Structures and Biological Activities of Diketopiperazines from Marine Organisms: A Review.

Authors:  Zhiqiang Song; Yage Hou; Qingrong Yang; Xinpeng Li; Shaohua Wu
Journal:  Mar Drugs       Date:  2021-07-21       Impact factor: 5.118

Review 3.  Marine Indole Alkaloids-Isolation, Structure and Bioactivities.

Authors:  Yong Hu; Siling Chen; Fang Yang; Shuai Dong
Journal:  Mar Drugs       Date:  2021-11-24       Impact factor: 5.118

Review 4.  Marine-Derived Indole Alkaloids and Their Biological and Pharmacological Activities.

Authors:  Joko Tri Wibowo; Peni Ahmadi; Siti Irma Rahmawati; Asep Bayu; Masteria Yunovilsa Putra; Anake Kijjoa
Journal:  Mar Drugs       Date:  2021-12-21       Impact factor: 5.118

  4 in total

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