Three New Depsipeptides, Homiamides A–C, Isolated from Streptomyces sp., ROA-065

Jeong Hyeon Kim; Ji Young Lee; Juri Lee; Prima F. Hillman; Jihye Lee; Byeongchan Choi; Man Jeong Paik; Songyi Lee; Sang Jip Nam

doi:10.3390/molecules29235539

Three New Depsipeptides, Homiamides A–C, Isolated from Streptomyces sp., ROA-065

Jeong Hyeon Kim, Ji Young Lee, Juri Lee, Prima F. Hillman, Jihye Lee, Byeongchan Choi, Man Jeong Paik, Songyi Lee, Sang Jip Nam

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

Abstract

Three new depsipeptides, homiamides A–C (1–3), were isolated from a marine sediment-derived strain of Streptomyces sp., ROA-065. The planar structures of homiamides A–C (1–3) were elucidated using mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopic data. The absolute configurations of 1–3 were deduced from the application of the Marfey’s method and GC-MS analysis after formation of the O-trifluoroacetylated (S)-(+)-methyl-2-butyl ester derivatives of amino acids. Compounds 1–3 exhibited weak anti-bacterial activities against both Gram-positive bacteria and Gram-negative bacteria, with compound 1 showing MIC values of 32–64 μg/mL. In antifouling assays, compounds 1 and 2 displayed moderate activity against Micrococcus luteus KCTC 3063, while compound 3 exhibited weak activity against all tested bacteria.

Original language	English
Article number	5539
Journal	Molecules
Volume	29
Issue number	23
DOIs	https://doi.org/10.3390/molecules29235539
State	Published - Dec 2024

Bibliographical note

Publisher Copyright:
© 2024 by the authors.

Keywords

antibacterial activity
depsipeptide
gas chromatography mass spectrometry
Marfey’s method
Streptomyces

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10.3390/molecules29235539

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@article{2716296fc55f48a096e9c619e21ee2a2,

title = "Three New Depsipeptides, Homiamides A–C, Isolated from Streptomyces sp., ROA-065",

abstract = "Three new depsipeptides, homiamides A–C (1–3), were isolated from a marine sediment-derived strain of Streptomyces sp., ROA-065. The planar structures of homiamides A–C (1–3) were elucidated using mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopic data. The absolute configurations of 1–3 were deduced from the application of the Marfey{\textquoteright}s method and GC-MS analysis after formation of the O-trifluoroacetylated (S)-(+)-methyl-2-butyl ester derivatives of amino acids. Compounds 1–3 exhibited weak anti-bacterial activities against both Gram-positive bacteria and Gram-negative bacteria, with compound 1 showing MIC values of 32–64 μg/mL. In antifouling assays, compounds 1 and 2 displayed moderate activity against Micrococcus luteus KCTC 3063, while compound 3 exhibited weak activity against all tested bacteria.",

keywords = "antibacterial activity, depsipeptide, gas chromatography mass spectrometry, Marfey{\textquoteright}s method, Streptomyces",

author = "Kim, {Jeong Hyeon} and Lee, {Ji Young} and Juri Lee and Hillman, {Prima F.} and Jihye Lee and Byeongchan Choi and Paik, {Man Jeong} and Songyi Lee and Nam, {Sang Jip}",

note = "Publisher Copyright: {\textcopyright} 2024 by the authors.",

year = "2024",

month = dec,

doi = "10.3390/molecules29235539",

language = "English",

volume = "29",

journal = "Molecules",

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T1 - Three New Depsipeptides, Homiamides A–C, Isolated from Streptomyces sp., ROA-065

AU - Kim, Jeong Hyeon

AU - Lee, Ji Young

AU - Lee, Juri

AU - Hillman, Prima F.

AU - Lee, Jihye

AU - Choi, Byeongchan

AU - Paik, Man Jeong

AU - Lee, Songyi

AU - Nam, Sang Jip

PY - 2024/12

Y1 - 2024/12

N2 - Three new depsipeptides, homiamides A–C (1–3), were isolated from a marine sediment-derived strain of Streptomyces sp., ROA-065. The planar structures of homiamides A–C (1–3) were elucidated using mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopic data. The absolute configurations of 1–3 were deduced from the application of the Marfey’s method and GC-MS analysis after formation of the O-trifluoroacetylated (S)-(+)-methyl-2-butyl ester derivatives of amino acids. Compounds 1–3 exhibited weak anti-bacterial activities against both Gram-positive bacteria and Gram-negative bacteria, with compound 1 showing MIC values of 32–64 μg/mL. In antifouling assays, compounds 1 and 2 displayed moderate activity against Micrococcus luteus KCTC 3063, while compound 3 exhibited weak activity against all tested bacteria.

AB - Three new depsipeptides, homiamides A–C (1–3), were isolated from a marine sediment-derived strain of Streptomyces sp., ROA-065. The planar structures of homiamides A–C (1–3) were elucidated using mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopic data. The absolute configurations of 1–3 were deduced from the application of the Marfey’s method and GC-MS analysis after formation of the O-trifluoroacetylated (S)-(+)-methyl-2-butyl ester derivatives of amino acids. Compounds 1–3 exhibited weak anti-bacterial activities against both Gram-positive bacteria and Gram-negative bacteria, with compound 1 showing MIC values of 32–64 μg/mL. In antifouling assays, compounds 1 and 2 displayed moderate activity against Micrococcus luteus KCTC 3063, while compound 3 exhibited weak activity against all tested bacteria.

KW - antibacterial activity

KW - depsipeptide

KW - gas chromatography mass spectrometry

KW - Marfey’s method

KW - Streptomyces

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U2 - 10.3390/molecules29235539

DO - 10.3390/molecules29235539

M3 - Article

C2 - 39683698

AN - SCOPUS:85212675783

SN - 1420-3049

VL - 29

JO - Molecules

JF - Molecules

IS - 23

M1 - 5539

ER -

Three New Depsipeptides, Homiamides A–C, Isolated from Streptomyces sp., ROA-065

Abstract

Bibliographical note

Keywords

UN SDGs

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