Dianthiamides A–E, proline-containing orbitides from dianthus chinensis

Jin Woo Lee; Jun Gu Kim; Jae Sang Han; Yong Beom Cho; Yu Jin Lee; Dongho Lee; Dae Hwan Shin; Jin Tae Hong; Mi Kyeong Lee; Bang Yeon Hwang

doi:10.3390/molecules26237275

Dianthiamides A–E, proline-containing orbitides from dianthus chinensis

Jin Woo Lee, Jun Gu Kim, Jae Sang Han, Yong Beom Cho, Yu Jin Lee, Dongho Lee, Dae Hwan Shin, Jin Tae Hong, Mi Kyeong Lee, Bang Yeon Hwang

Department of Biosystems and Biotechnology

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

1 Citation (Scopus)

Abstract

Orbitides are plant-derived small cyclic peptides with a wide range of biological activities. Phytochemical investigation of the whole plants of Dianthus chinensis was performed with the aim to discover new bioactive orbitides. Five undescribed proline-containing orbitides, dianthiamides A–E (1–5), were isolated from a methanolic extract of Dianthus chinensis. Their structures were elucidated by extensive analysis of 1D and 2D NMR and HRESI–TOF–MS as well as ESI–MS/MS fragmentation data. The absolute configuration of the amino acid residues of compounds 1–5 was determined by Marfey’s method. All compounds were tested for their cytotoxic activity, and dianthiamide A (1) exhibited weak activity against A549 cell line with IC₅₀ value of 47.9 µM.

Original language	English
Article number	7275
Journal	Molecules
Volume	26
Issue number	23
DOIs	https://doi.org/10.3390/molecules26237275
Publication status	Published - 2021 Dec 1

Bibliographical note

Funding Information:
Funding: This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MIST) (No. 2020R1A2C1008406 and the Medical Research Center Program 2017R1A5A2015541).

Publisher Copyright:
© 2021 by the authors. Licensee MDPI, Basel, Switzerland.

Keywords

Caryophyllaceae
Cytotoxic activity
Dianthus chinensis
Orbitide
Structure elucidation

ASJC Scopus subject areas

Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry

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10.3390/molecules26237275

Cite this

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title = "Dianthiamides A–E, proline-containing orbitides from dianthus chinensis",

abstract = "Orbitides are plant-derived small cyclic peptides with a wide range of biological activities. Phytochemical investigation of the whole plants of Dianthus chinensis was performed with the aim to discover new bioactive orbitides. Five undescribed proline-containing orbitides, dianthiamides A–E (1–5), were isolated from a methanolic extract of Dianthus chinensis. Their structures were elucidated by extensive analysis of 1D and 2D NMR and HRESI–TOF–MS as well as ESI–MS/MS fragmentation data. The absolute configuration of the amino acid residues of compounds 1–5 was determined by Marfey{\textquoteright}s method. All compounds were tested for their cytotoxic activity, and dianthiamide A (1) exhibited weak activity against A549 cell line with IC50 value of 47.9 µM.",

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author = "Lee, {Jin Woo} and Kim, {Jun Gu} and Han, {Jae Sang} and Cho, {Yong Beom} and Lee, {Yu Jin} and Dongho Lee and Shin, {Dae Hwan} and Hong, {Jin Tae} and Lee, {Mi Kyeong} and Hwang, {Bang Yeon}",

note = "Funding Information: Funding: This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MIST) (No. 2020R1A2C1008406 and the Medical Research Center Program 2017R1A5A2015541). Publisher Copyright: {\textcopyright} 2021 by the authors. Licensee MDPI, Basel, Switzerland.",

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doi = "10.3390/molecules26237275",

language = "English",

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AU - Lee, Jin Woo

AU - Kim, Jun Gu

AU - Han, Jae Sang

AU - Cho, Yong Beom

AU - Lee, Yu Jin

AU - Lee, Dongho

AU - Shin, Dae Hwan

AU - Hong, Jin Tae

AU - Lee, Mi Kyeong

AU - Hwang, Bang Yeon

N1 - Funding Information: Funding: This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MIST) (No. 2020R1A2C1008406 and the Medical Research Center Program 2017R1A5A2015541). Publisher Copyright: © 2021 by the authors. Licensee MDPI, Basel, Switzerland.

PY - 2021/12/1

Y1 - 2021/12/1

N2 - Orbitides are plant-derived small cyclic peptides with a wide range of biological activities. Phytochemical investigation of the whole plants of Dianthus chinensis was performed with the aim to discover new bioactive orbitides. Five undescribed proline-containing orbitides, dianthiamides A–E (1–5), were isolated from a methanolic extract of Dianthus chinensis. Their structures were elucidated by extensive analysis of 1D and 2D NMR and HRESI–TOF–MS as well as ESI–MS/MS fragmentation data. The absolute configuration of the amino acid residues of compounds 1–5 was determined by Marfey’s method. All compounds were tested for their cytotoxic activity, and dianthiamide A (1) exhibited weak activity against A549 cell line with IC50 value of 47.9 µM.

AB - Orbitides are plant-derived small cyclic peptides with a wide range of biological activities. Phytochemical investigation of the whole plants of Dianthus chinensis was performed with the aim to discover new bioactive orbitides. Five undescribed proline-containing orbitides, dianthiamides A–E (1–5), were isolated from a methanolic extract of Dianthus chinensis. Their structures were elucidated by extensive analysis of 1D and 2D NMR and HRESI–TOF–MS as well as ESI–MS/MS fragmentation data. The absolute configuration of the amino acid residues of compounds 1–5 was determined by Marfey’s method. All compounds were tested for their cytotoxic activity, and dianthiamide A (1) exhibited weak activity against A549 cell line with IC50 value of 47.9 µM.

KW - Caryophyllaceae

KW - Cytotoxic activity

KW - Dianthus chinensis

KW - Orbitide

KW - Structure elucidation

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DO - 10.3390/molecules26237275

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SN - 1420-3049

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JO - Molecules

JF - Molecules

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ER -

Dianthiamides A–E, proline-containing orbitides from dianthus chinensis

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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