Ptp1b inhibitory secondary metabolites from an antarctic fungal strain acremonium sp. Sf-7394

Hye Jin Kim; Xiao Jun Li; Dong Cheol Kim; Tai Kyoung Kim; Jae Hak Sohn; Haeun Kwon; Dongho Lee; Youn Chul Kim; Joung Han Yim; Hyuncheol Oh

doi:10.3390/molecules26185505

Ptp1b inhibitory secondary metabolites from an antarctic fungal strain acremonium sp. Sf-7394

Hye Jin Kim, Xiao Jun Li, Dong Cheol Kim, Tai Kyoung Kim, Jae Hak Sohn, Haeun Kwon, Dongho Lee, Youn Chul Kim, Joung Han Yim, Hyuncheol Oh

Department of Biosystems and Biotechnology

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

4 Citations (Scopus)

Abstract

Chemical investigation of the Antarctic lichen-derived fungal strain Acremonium sp. SF-7394 yielded a new amphilectane-type diterpene, acrepseudoterin (1), and a new acorane-type sesquiterpene glycoside, isocordycepoloside A (2). In addition, three known fungal metabolites, (−)-ternatin (3), [D-Leu]-ternatin (4), and pseurotin A (5), were isolated from the EtOAc extract of the fungal strain. Their structures were mainly elucidated by analyzing their NMR and MS data. The absolute configuration of 1 was proposed by electronic circular dichroism calculations, and the absolute configuration of the sugar unit in 2 was determined by a chemical method. The inhibitory effects of the isolated compounds on protein tyrosine phosphatase 1B (PTP1B) were evaluated by enzymatic assays; results indicated that acrepseudoterin (1) and [D-Leu]-ternatin (4) dose-dependently inhibited the enzyme activity with IC₅₀ values of 22.8 ± 1.1 µM and 14.8 ± 0.3 µM, respectively. Moreover, compound 1 was identified as a competitive inhibitor of PTP1B.

Original language	English
Article number	5505
Journal	Molecules
Volume	26
Issue number	18
DOIs	https://doi.org/10.3390/molecules26185505
Publication status	Published - 2021 Sept

Bibliographical note

Funding Information:
Funding: This research was funded by the Korea Polar Research Institute (PE21150).

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

Keywords

Acremonium sp
Antarctic fungal metabolites
PTP1B
Terpenoids

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/molecules26185505

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title = "Ptp1b inhibitory secondary metabolites from an antarctic fungal strain acremonium sp. Sf-7394",

abstract = "Chemical investigation of the Antarctic lichen-derived fungal strain Acremonium sp. SF-7394 yielded a new amphilectane-type diterpene, acrepseudoterin (1), and a new acorane-type sesquiterpene glycoside, isocordycepoloside A (2). In addition, three known fungal metabolites, (−)-ternatin (3), [D-Leu]-ternatin (4), and pseurotin A (5), were isolated from the EtOAc extract of the fungal strain. Their structures were mainly elucidated by analyzing their NMR and MS data. The absolute configuration of 1 was proposed by electronic circular dichroism calculations, and the absolute configuration of the sugar unit in 2 was determined by a chemical method. The inhibitory effects of the isolated compounds on protein tyrosine phosphatase 1B (PTP1B) were evaluated by enzymatic assays; results indicated that acrepseudoterin (1) and [D-Leu]-ternatin (4) dose-dependently inhibited the enzyme activity with IC50 values of 22.8 ± 1.1 µM and 14.8 ± 0.3 µM, respectively. Moreover, compound 1 was identified as a competitive inhibitor of PTP1B.",

keywords = "Acremonium sp, Antarctic fungal metabolites, PTP1B, Terpenoids",

author = "Kim, {Hye Jin} and Li, {Xiao Jun} and Kim, {Dong Cheol} and Kim, {Tai Kyoung} and Sohn, {Jae Hak} and Haeun Kwon and Dongho Lee and Kim, {Youn Chul} and Yim, {Joung Han} and Hyuncheol Oh",

note = "Funding Information: Funding: This research was funded by the Korea Polar Research Institute (PE21150). Publisher Copyright: {\textcopyright} 2021 by the authors. Licensee MDPI, Basel, Switzerland.",

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month = sep,

doi = "10.3390/molecules26185505",

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AU - Kim, Hye Jin

AU - Li, Xiao Jun

AU - Kim, Dong Cheol

AU - Kim, Tai Kyoung

AU - Sohn, Jae Hak

AU - Kwon, Haeun

AU - Lee, Dongho

AU - Kim, Youn Chul

AU - Yim, Joung Han

AU - Oh, Hyuncheol

PY - 2021/9

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N2 - Chemical investigation of the Antarctic lichen-derived fungal strain Acremonium sp. SF-7394 yielded a new amphilectane-type diterpene, acrepseudoterin (1), and a new acorane-type sesquiterpene glycoside, isocordycepoloside A (2). In addition, three known fungal metabolites, (−)-ternatin (3), [D-Leu]-ternatin (4), and pseurotin A (5), were isolated from the EtOAc extract of the fungal strain. Their structures were mainly elucidated by analyzing their NMR and MS data. The absolute configuration of 1 was proposed by electronic circular dichroism calculations, and the absolute configuration of the sugar unit in 2 was determined by a chemical method. The inhibitory effects of the isolated compounds on protein tyrosine phosphatase 1B (PTP1B) were evaluated by enzymatic assays; results indicated that acrepseudoterin (1) and [D-Leu]-ternatin (4) dose-dependently inhibited the enzyme activity with IC50 values of 22.8 ± 1.1 µM and 14.8 ± 0.3 µM, respectively. Moreover, compound 1 was identified as a competitive inhibitor of PTP1B.

AB - Chemical investigation of the Antarctic lichen-derived fungal strain Acremonium sp. SF-7394 yielded a new amphilectane-type diterpene, acrepseudoterin (1), and a new acorane-type sesquiterpene glycoside, isocordycepoloside A (2). In addition, three known fungal metabolites, (−)-ternatin (3), [D-Leu]-ternatin (4), and pseurotin A (5), were isolated from the EtOAc extract of the fungal strain. Their structures were mainly elucidated by analyzing their NMR and MS data. The absolute configuration of 1 was proposed by electronic circular dichroism calculations, and the absolute configuration of the sugar unit in 2 was determined by a chemical method. The inhibitory effects of the isolated compounds on protein tyrosine phosphatase 1B (PTP1B) were evaluated by enzymatic assays; results indicated that acrepseudoterin (1) and [D-Leu]-ternatin (4) dose-dependently inhibited the enzyme activity with IC50 values of 22.8 ± 1.1 µM and 14.8 ± 0.3 µM, respectively. Moreover, compound 1 was identified as a competitive inhibitor of PTP1B.

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Ptp1b inhibitory secondary metabolites from an antarctic fungal strain acremonium sp. Sf-7394

Abstract

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