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

Marine Drugs
Larissa BuedenbenderAnthony R Carroll

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 (3⁻6). 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 (1⁻2) 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.

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Mar 3, 2018·Journal of Natural Products·Larissa BuedenbenderAnthony R Carroll

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Citations

Nov 30, 2019·International Journal of Molecular Sciences·Tawanda Zininga, Addmore Shonhai
Feb 7, 2020·Natural Product Reports·Anthony R CarrollMichèle R Prinsep
Dec 12, 2020·Parasitology International·Arpron LeesombunYoshifumi Nishikawa
Jan 16, 2021·The Journal of Antibiotics·Aki IshiyamaMasato Iwatsuki

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Datasets Mentioned

BETA
MF773774

Methods Mentioned

BETA
NMR
circular dichroism

Software Mentioned

ChemBio3D Ultra
GaussSum
SpecDis
Schrödinger MacroModel 2016
Gaussian
GraphPad Prism
MacroModel

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