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Mar. Drugs 2018, 16(6), 189; https://doi.org/10.3390/md16060189

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

1
Environmental Futures Research Institute, School of Environment and Science, Griffith University, Gold Coast Campus, QLD 4222, Australia
2
Griffith Institute for Drug Discovery, Griffith University, Brisbane, QLD 4111, Australia
3
GeneCology Research Centre, Faculty of Science, Health, Education and Engineering, University of the Sunshine Coast, Maroochydore, QLD 4558, Australia
*
Authors to whom correspondence should be addressed.
Received: 8 May 2018 / Revised: 18 May 2018 / Accepted: 22 May 2018 / Published: 30 May 2018
(This article belongs to the Special Issue Marine Natural Products from Symbiotic Ecosystems)
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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. View Full-Text
Keywords: actinomycetes; Streptomyces; ascidian-associated actinomycetes; Symplegma rubra; polyketide; ansamycin derivative; herbimycin; antiplasmodial activity actinomycetes; Streptomyces; ascidian-associated actinomycetes; Symplegma rubra; polyketide; ansamycin derivative; herbimycin; antiplasmodial activity
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Buedenbender, L.; Robertson, L.P.; Lucantoni, L.; Avery, V.M.; Kurtböke, D.İ.; Carroll, A.R. HSQC-TOCSY Fingerprinting-Directed Discovery of Antiplasmodial Polyketides from the Marine Ascidian-Derived Streptomyces sp. (USC-16018). Mar. Drugs 2018, 16, 189.

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