Penipyrols C-G and methyl-penipyrol A, α-pyrone polyketides from the mangrove derived fungus Penicillium sp. HDN-11-131.

Animals Dose-Response Relationship, Drug Hypoglycemic Agents / chemistry Insulin-Secreting Cells / drug effects Molecular Structure Penicillium / chemistry Polyketides / chemistry Pyrones / chemistry Regeneration / drug effects Structure-Activity Relationship Zebrafish
Diabetes Polyketides Zebrafish α-Pyrone β-cell regeneration γ-Butyrolactone

Journal

Bioorganic chemistry
ISSN: 1090-2120
Titre abrégé: Bioorg Chem
Pays: United States
ID NLM: 1303703

Informations de publication

Date de publication:
08 2021
Historique:
received: 30 01 2021
revised: 22 04 2021
accepted: 05 05 2021
pubmed: 22 5 2021
medline: 3 11 2021
entrez: 21 5 2021
Statut: ppublish

Résumé

Six new α-pyrone polyketides, penipyrols C-G (1-5) and methyl-penipyrol A (6), together with one biogenetically related known compound, penipyrol A (7), were isolated from the extract of fungus Penicillium sp. HDN-11-131. Their structures including the absolute configurations were established by extensive spectroscopic analysis, Mosher's method, and ECD calculations as well as biogenic considerations. Compounds 1-4 possess a rare skeleton featuring γ-butyrolactone linked to α-pyrone ring through double bond. Compound 1 can induce pancreatic β-cell regeneration in zebrafish at 10 μM, which demonstrated promising anti-diabetes potential.

Identifiants

DOI: 10.1016/j.bioorg.2021.104975 PMID: 34020278
pubmed: 34020278
pii: S0045-2068(21)00352-7
doi: 10.1016/j.bioorg.2021.104975
pii:
doi:

Substances chimiques

Hypoglycemic Agents 0
Polyketides 0
Pyrones 0

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

104975

Informations de copyright

Copyright © 2021 Elsevier Inc. All rights reserved.

Auteurs

Lu Wang (L)

Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, PR China.

Yeqin Shi (Y)

Fujian Provincial Key Laboratory of Innovative Drug Target Research, School of Pharmaceutical Science, Xiamen University, Fujian 361102, PR China.

Qian Che (Q)

Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, PR China.

Tianjiao Zhu (T)

Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, PR China.

Guojian Zhang (G)

Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, PR China; Laboratory for Marine Drugs and Bioproducts of Qingdao Pilot National Laboratory for Marine Science and Technology, Qingdao 266237, PR China.

Xiaokun Zhang (X)

Fujian Provincial Key Laboratory of Innovative Drug Target Research, School of Pharmaceutical Science, Xiamen University, Fujian 361102, PR China.

Mingyu Li (M)

Fujian Provincial Key Laboratory of Innovative Drug Target Research, School of Pharmaceutical Science, Xiamen University, Fujian 361102, PR China. Electronic address: limingyu@xmu.edu.cn.

Dehai Li (D)

Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, PR China; Laboratory for Marine Drugs and Bioproducts of Qingdao Pilot National Laboratory for Marine Science and Technology, Qingdao 266237, PR China. Electronic address: dehaili@ouc.edu.cn.

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Classifications MeSH

questionsmedicales.fr › Eucaryotes › Animaux › Penipyrols C-G and methyl-penipyrol A,...
questionsmedicales.fr › Phénomènes physiologiques › Phénomènes pharmacologiques et toxicologiques › Phénomènes toxicologiques › Relation dose-effet des médicaments › Penipyrols C-G and methyl-penipyrol A,...
questionsmedicales.fr › Actions chimiques et utilisations › Actions pharmacologiques › Effets physiologiques des médicaments › Hypoglycémiants › Penipyrols C-G and methyl-penipyrol A,...
questionsmedicales.fr › Cellules › Cellules épithéliales › Cellules entéroendocrines › Cellules à insuline › Penipyrols C-G and methyl-penipyrol A,...
questionsmedicales.fr › Phénomènes chimiques › Structure moléculaire › Penipyrols C-G and methyl-penipyrol A,...
questionsmedicales.fr › Eucaryotes › Champignons › Deuteromycota › Penicillium › Penipyrols C-G and methyl-penipyrol A,...
questionsmedicales.fr › Composés polycycliques › Composés macrocycliques › Polycétides › Penipyrols C-G and methyl-penipyrol A,...
questionsmedicales.fr › Composés hétérocycliques › Composés hétéromonocycliques › Pyrannes › Pyrones › Penipyrols C-G and methyl-penipyrol A,...
questionsmedicales.fr › Phénomènes biologiques › Régénération › Penipyrols C-G and methyl-penipyrol A,...
questionsmedicales.fr › Phénomènes physiologiques › Phénomènes pharmacologiques et toxicologiques › Phénomènes pharmacologiques › Relation structure-activité › Penipyrols C-G and methyl-penipyrol A,...
questionsmedicales.fr › Eucaryotes › Animaux › Chordés › Vertébrés › Poissons › Cypriniformes › Cyprinidae › Danio zébré › Penipyrols C-G and methyl-penipyrol A,...