HSQC-TOCSY Fingerprinting-Directed Discovery of Antiplasmodial Polyketides from the Marine Ascidian-Derived Streptomyces sp. (USC-16018)

Larissa Buedenbender; Luke P Robertson; Leonardo Lucantoni; Vicky M Avery; D Ipek Kurtboke; Anthony R Carroll

doi:10.3390/md16060189

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HSQC-TOCSY Fingerprinting-Directed Discovery of Antiplasmodial Polyketides from the Marine Ascidian-Derived Streptomyces sp. (USC-16018)

Journal article

Open access

Peer reviewed

HSQC-TOCSY Fingerprinting-Directed Discovery of Antiplasmodial Polyketides from the Marine Ascidian-Derived Streptomyces sp. (USC-16018)

Larissa Buedenbender, Luke P Robertson, Leonardo Lucantoni, Vicky M Avery, D Ipek Kurtboke and Anthony R Carroll

Marine Drugs, Vol.16(6), pp.1-11

2018

DOI: https://doi.org/10.3390/md16060189

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Abstract

actinomycetes

Streptomyces

ascidian-associated actinomycetes

Symplegma rubra

polyketide

ansamycin derivative

herbimycin

antiplasmodial activity

Chemical investigations on the fermentation extract obtained from an ascidian-derived Streptomyces sp. (USC-16018) yielded a new ansamycin polyketide, herbimycin G (1), as well as a known macrocyclic polyketide, elaiophylin (2), and four known diketopiperazines (3â»6). The structures of the compounds were elucidated based on 1D/2D NMR and MS data. The absolute configuration of 1 was established by comparison of experimental and predicted electronic circular dichroism (ECD) data. Antiplasmodial activities were tested for the natural products against chloroquine sensitive (3D7) and chloroquine resistant (Dd2) Plasmodium falciparum strains; the two polyketides (1â»2) demonstrated an inhibition of >75% against both parasite strains and while 2 was highly cytotoxic, herbimycin G (1) showed no cytotoxicity and good predicted water solubility.

Details

Title: HSQC-TOCSY Fingerprinting-Directed Discovery of Antiplasmodial Polyketides from the Marine Ascidian-Derived Streptomyces sp. (USC-16018)
Authors: Larissa Buedenbender (Author) - Griffith University
Luke P Robertson (Author) - Griffith University
Leonardo Lucantoni (Author) - Griffith University
Vicky M Avery (Author) - Griffith University
D Ipek Kurtboke (Author) - University of the Sunshine Coast - Faculty of Science, Health, Education and Engineering
Anthony R Carroll (Author) - Griffith University
Publication details: Marine Drugs, Vol.16(6), pp.1-11
Publisher: MDPI AG
Date published: 2018
DOI: 10.3390/md16060189
ISSN: 1660-3397
Copyright note: Copyright © 2018 by the authors. Licensee MDPI, Basel, Switzerland. This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).
Organisation Unit: School of Science and Engineering - Legacy; GeneCology Research Centre - Legacy; School of Science, Technology and Engineering; Centre for Bioinnovation
Language: English
Record Identifier: 99451363402621
Output Type: Journal article

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Collaboration types: Domestic collaboration
Web Of Science research areas: Chemistry, Medicinal; Pharmacology & Pharmacy

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