Depsidomycins B and C: New cyclic peptides from a ginseng farm soil-derived actinomycete

Yun Kwon; Woong Sub Byun; Byung Yong Kim; Myoung Chong Song; Munhyung Bae; Yeo Joon Yoon; Jongheon Shin; Sang Kook Lee; Dong Chan Oh

doi:10.3390/molecules23061266

Depsidomycins B and C: New cyclic peptides from a ginseng farm soil-derived actinomycete

Yun Kwon
, Woong Sub Byun
, Byung Yong Kim
, Myoung Chong Song
, Munhyung Bae
, Yeo Joon Yoon
, Jongheon Shin
, Sang Kook Lee
, Dong Chan Oh

Department of Pharmacy

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

13 Scopus citations

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).

Original language	English
Article number	1266
Journal	Molecules
Volume	23
Issue number	6
DOIs	https://doi.org/10.3390/molecules23061266
State	Published - 2018

Keywords

Actinomycete
Antimetastatic
Cyclic peptide
Farm soil
Streptomyces sp.

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.3390/molecules23061266

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title = "Depsidomycins B and C: New cyclic peptides from a ginseng farm soil-derived actinomycete",

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{\textquoteright}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 = "Actinomycete, Antimetastatic, Cyclic peptide, Farm soil, Streptomyces sp.",

author = "Yun Kwon and Byun, \{Woong Sub\} and Kim, \{Byung Yong\} and Song, \{Myoung Chong\} and Munhyung Bae and Yoon, \{Yeo Joon\} and Jongheon Shin and Lee, \{Sang Kook\} and Oh, \{Dong Chan\}",

note = "Publisher Copyright: {\textcopyright} 2018 by the authors.",

year = "2018",

doi = "10.3390/molecules23061266",

language = "English",

volume = "23",

journal = "Molecules",

issn = "1420-3049",

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TY - JOUR

T1 - Depsidomycins B and C

T2 - New cyclic peptides from a ginseng farm soil-derived actinomycete

AU - Kwon, Yun

AU - Byun, Woong Sub

AU - Kim, Byung Yong

AU - Song, Myoung Chong

AU - Bae, Munhyung

AU - Yoon, Yeo Joon

AU - Shin, Jongheon

AU - Lee, Sang Kook

AU - Oh, Dong Chan

PY - 2018

Y1 - 2018

N2 - 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).

AB - 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).

KW - Actinomycete

KW - Antimetastatic

KW - Cyclic peptide

KW - Farm soil

KW - Streptomyces sp.

UR - https://www.scopus.com/pages/publications/85047857096

U2 - 10.3390/molecules23061266

DO - 10.3390/molecules23061266

M3 - Article

C2 - 29799492

AN - SCOPUS:85047857096

SN - 1420-3049

VL - 23

JO - Molecules

JF - Molecules

IS - 6

M1 - 1266

ER -

Depsidomycins B and C: New cyclic peptides from a ginseng farm soil-derived actinomycete

Abstract

Keywords

UN SDGs

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