Literature DB >> 27359053

Janadolide, a Cyclic Polyketide-Peptide Hybrid Possessing a tert-Butyl Group from an Okeania sp. Marine Cyanobacterium.

Hidetoshi Ogawa1, Arihiro Iwasaki1, Shinpei Sumimoto1, Yuki Kanamori1, Osamu Ohno2, Masato Iwatsuki, Aki Ishiyama, Rei Hokari, Kazuhiko Otoguro, Satoshi O̅mura, Kiyotake Suenaga1.   

Abstract

Janadolide, a new cyclic polyketide-peptide hybrid possessing a tert-butyl group, was isolated from an Okeania sp. marine cyanobacterium. The gross structure was elucidated by spectroscopic analyses, and the absolute configurations of the amino acid moieties were determined by acid hydrolysis and chiral-phase HPLC analyses. The absolute configuration of the two stereogenic centers in the polyketide moiety was elucidated based on a combination of degradation reactions and spectroscopic analyses including the phenyl-glycine methyl ester method. Janadolide showed potent antitrypanosomal activity with an IC50 value of 47 nM without cytotoxicity against human cells at 10 μM.

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Year:  2016        PMID: 27359053     DOI: 10.1021/acs.jnatprod.6b00171

Source DB:  PubMed          Journal:  J Nat Prod        ISSN: 0163-3864            Impact factor:   4.050


  12 in total

1.  Biosynthesis of t-Butyl in Apratoxin A: Functional Analysis and Architecture of a PKS Loading Module.

Authors:  Meredith A Skiba; Andrew P Sikkema; Nathan A Moss; Andrew N Lowell; Min Su; Rebecca M Sturgis; Lena Gerwick; William H Gerwick; David H Sherman; Janet L Smith
Journal:  ACS Chem Biol       Date:  2018-05-08       Impact factor: 5.100

Review 2.  Marine natural product peptides with therapeutic potential: Chemistry, biosynthesis, and pharmacology.

Authors:  Vedanjali Gogineni; Mark T Hamann
Journal:  Biochim Biophys Acta Gen Subj       Date:  2017-08-24       Impact factor: 3.770

Review 3.  Marine Cyclic Peptides: Antimicrobial Activity and Synthetic Strategies.

Authors:  Ricardo Ribeiro; Eugénia Pinto; Carla Fernandes; Emília Sousa
Journal:  Mar Drugs       Date:  2022-06-15       Impact factor: 6.085

Review 4.  Cyanobacteria-From the Oceans to the Potential Biotechnological and Biomedical Applications.

Authors:  Shaden A M Khalifa; Eslam S Shedid; Essa M Saied; Amir Reza Jassbi; Fatemeh H Jamebozorgi; Mostafa E Rateb; Ming Du; Mohamed M Abdel-Daim; Guo-Yin Kai; Montaser A M Al-Hammady; Jianbo Xiao; Zhiming Guo; Hesham R El-Seedi
Journal:  Mar Drugs       Date:  2021-04-24       Impact factor: 5.118

Review 5.  Structural Diversity, Biological Properties and Applications of Natural Products from Cyanobacteria. A Review.

Authors:  Sayed Asmat Ali Shah; Najeeb Akhter; Bibi Nazia Auckloo; Ishrat Khan; Yanbin Lu; Kuiwu Wang; Bin Wu; Yue-Wei Guo
Journal:  Mar Drugs       Date:  2017-11-10       Impact factor: 5.118

6.  Efforts To Access the Potent Antitrypanosomal Marine Natural Product Janadolide: Synthesis of Des-tert-butyl Janadolide and Its Biological Evaluation.

Authors:  Paresh R Athawale; Gorakhnath R Jachak; Anurag Shukla; Dhanasekaran Shanmugam; D Srinivasa Reddy
Journal:  ACS Omega       Date:  2018-02-27

7.  Total Synthesis of Desmethyl Jahanyne and Its Lipo-Tetrapeptide Conjugates Derived from Parent Skeleton as BCL-2-Mediated Apoptosis-Inducing Agents.

Authors:  Shivakrishna Kallepu; Minnapuram Kavitha; Ragini Yeeravalli; Kanakaraju Manupati; Surender Singh Jadav; Amitava Das; Prathama S Mainkar; Srivari Chandrasekhar
Journal:  ACS Omega       Date:  2018-01-04

8.  Biosynthetic origin of butyrolactol A, an antifungal polyketide produced by a marine-derived Streptomyces.

Authors:  Enjuro Harunari; Hisayuki Komaki; Yasuhiro Igarashi
Journal:  Beilstein J Org Chem       Date:  2017-03-08       Impact factor: 2.883

Review 9.  Marine Cyanobacteria: A Source of Lead Compounds and their Clinically-Relevant Molecular Targets.

Authors:  Lik Tong Tan; Ma Yadanar Phyo
Journal:  Molecules       Date:  2020-05-08       Impact factor: 4.411

Review 10.  Marine Natural Peptides: Determination of Absolute Configuration Using Liquid Chromatography Methods and Evaluation of Bioactivities.

Authors:  Ye' Zaw Phyo; João Ribeiro; Carla Fernandes; Anake Kijjoa; Madalena M M Pinto
Journal:  Molecules       Date:  2018-01-31       Impact factor: 4.411

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