Abstract
Three new hydroxylated rhamnolipids, dokdolipids A−C (1−3) were obtained from the marine actinomycete Actinoalloteichus hymeniacidonis, which was isolated from a sediment sample collected off the coasts of Dokdo island, Republic of Korea. The structures of the isolated compounds were elucidated on the basis of 1D and 2D NMR and mass spectrometric data analyses. Their absolute configurations were assigned using the modified Mosher’s method and specific rotation values, as well as acid hydrolysis, chemical derivatizations and subsequent HPLC analysis to determine the configuration of the sugar moieties. All new compounds were evaluated for their cytotoxicity against six cancer cell lines, HCT-15, NUGC-3, NCI-H23, ACHN, PC-3 and MDA-MB-231. Compounds 1−3 displayed moderate cytotoxicity against all the cell lines tested with IC50 values ranging from 13.7−41.5 µM.
Highlights
Rhamnolipids belong to a class of biosurfactants composed of rhamnose linked to β-hydroxylated fatty acid chains [1]
The growth inhibition assay against human cancer cell lines was carried out according to a sulforhodamine B (SRB)
179DD-027 led to the isolation of three new hydroxylated rhamnolipids (1−3), and the identification of the sugar moiety as well as the determination of the absolute configuration of the stereogenic carbon in the carboxylic acid moiety
Summary
Rhamnolipids belong to a class of biosurfactants composed of rhamnose linked to β-hydroxylated fatty acid chains [1]. Various researchers have demonstrated that rhamnolipids display low toxicity, antimicrobial activities and the ability to suppress the growth of breast cancer cells [10,11]. These unique and diverse properties make them suitable to be used in a wide range of industrial demands such as the bioremediation of pollutants, cosmetics, food, pharmaceuticals and therapeutics [12]. Dokdo Island is a large volcanic island with 89 small islets and rocks containing rich and fermentation of the producing strain, solvent extraction and chemical investigation procedures led well-preserved biodiversity [16]. Subsequent fermentation of the producing strain, solvent to extraction the isolation three new rhamnolipids, named.
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