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Mar Drugs. 2018 May 30;16(6). pii: E189. doi: 10.3390/md16060189.

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

Author information

1
Environmental Futures Research Institute, School of Environment and Science, Griffith University, Gold Coast Campus, QLD 4222, Australia. larissa.buedenbender@griffithuni.edu.au.
2
Environmental Futures Research Institute, School of Environment and Science, Griffith University, Gold Coast Campus, QLD 4222, Australia. luke.robertson2@griffithuni.edu.au.
3
Griffith Institute for Drug Discovery, Griffith University, Brisbane, QLD 4111, Australia. luke.robertson2@griffithuni.edu.au.
4
Griffith Institute for Drug Discovery, Griffith University, Brisbane, QLD 4111, Australia. l.lucantoni@griffith.edu.au.
5
Griffith Institute for Drug Discovery, Griffith University, Brisbane, QLD 4111, Australia. v.avery@griffith.edu.au.
6
GeneCology Research Centre, Faculty of Science, Health, Education and Engineering, University of the Sunshine Coast, Maroochydore, QLD 4558, Australia. ikurtbok@usc.edu.au.
7
Environmental Futures Research Institute, School of Environment and Science, Griffith University, Gold Coast Campus, QLD 4222, Australia. a.carroll@griffith.edu.au.
8
Griffith Institute for Drug Discovery, Griffith University, Brisbane, QLD 4111, Australia. a.carroll@griffith.edu.au.

Abstract

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 (36). 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 (12) 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.

KEYWORDS:

Streptomyces; Symplegma rubra; actinomycetes; ansamycin derivative; antiplasmodial activity; ascidian-associated actinomycetes; herbimycin; polyketide

PMID:
29849004
PMCID:
PMC6025042
DOI:
10.3390/md16060189
[Indexed for MEDLINE]
Free PMC Article

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