Abstract
LC/MS-based chemical profiling of a ginseng farm soil-derived actinomycete strain, Streptomyces sp. BYK1371, enabled the discovery of two new cyclic heptapeptides, depsidomycins B and C (1 and 2), each containing two piperazic acid units and a formyl group at their N-terminus. The structures of 1 and 2 were elucidated by a combination of spectroscopic and chemical analyses. These new compounds were determined to possess d-leucine, d-threonine, d-valine, and S-piperazic acid based on the advanced Marfey's method and a GITC (2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl isothiocyanate) derivatization of their hydrolysates, followed by LC/MS analysis. Depsidomycins B and C displayed significant antimetastatic activities against metastatic breast cancer cells (MDA-MB-231).
Keywords:
Streptomyces sp.; actinomycete; antimetastatic; cyclic peptide; farm soil.
MeSH terms
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / isolation & purification*
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Antineoplastic Agents / pharmacology
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Cell Line, Tumor
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Cell Survival / drug effects
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Epithelial Cells / drug effects
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Epithelial Cells / pathology
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Farms
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Humans
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Isothiocyanates / chemistry
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Leucine / chemistry
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Leucine / isolation & purification
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Oligopeptides / chemistry
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Oligopeptides / isolation & purification*
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Oligopeptides / pharmacology
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Panax / growth & development
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Pyridazines / chemistry
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Pyridazines / isolation & purification
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Soil Microbiology*
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Stereoisomerism
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Streptomyces / chemistry*
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Streptomyces / metabolism
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Threonine / chemistry
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Threonine / isolation & purification
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Valine / chemistry
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Valine / isolation & purification
Substances
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Antineoplastic Agents
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Isothiocyanates
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Oligopeptides
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Pyridazines
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depsidomycin
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2,3,4,6-tetra-O-acetylglucopyranosylisothiocyanate
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Threonine
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piperazic acid
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Leucine
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Valine