Helvamide, a new inhibitor of sterol O-acyltransferase produced by the fungus Aspergillus nidulans BF-0142.

Animals Aspergillus nidulans / metabolism CHO Cells Cricetulus Enzyme Inhibitors / chemistry Magnetic Resonance Spectroscopy Molecular Structure Piperazines / chemistry Sterol O-Acyltransferase / antagonists & inhibitors

Journal

The Journal of antibiotics
ISSN: 1881-1469
Titre abrégé: J Antibiot (Tokyo)
Pays: England
ID NLM: 0151115

Informations de publication

Date de publication:
01 2019
Historique:
received: 08 06 2018
accepted: 01 09 2018
revised: 08 08 2018
pubmed: 12 10 2018
medline: 30 4 2019
entrez: 12 10 2018
Statut: ppublish

Résumé

A new piperazine derivative designated helvamide was isolated as a pair of rotamers (1 and 2) from the culture broth of the fungus Aspergillus nidulans BF-0142 along with a known helvafuranone (3). The structures of 1 and 2 were elucidated based on spectroscopic analyses by the interpretation of one-dimensional and two-dimensional nuclear magnetic resonance data, ROESY (rotational Overhauser effect spectroscopy) correlations, and a chemical method. Helvamide existed as a rotameric mixture (1 and 2) in dimethyl sulfoxide. Helvamide inhibited sterol O-acyltransferases 1 and 2 (SOAT1 and SOAT2) in enzyme-based and cell-based assays using SOAT1-expressing and SOAT2-expressing Chinese hamster ovary (CHO) cells.

Identifiants

DOI: 10.1038/s41429-018-0101-8 PMID: 30305686
pubmed: 30305686
doi: 10.1038/s41429-018-0101-8
pii: 10.1038/s41429-018-0101-8
doi:

Substances chimiques

Enzyme Inhibitors 0
Piperazines 0
Sterol O-Acyltransferase EC 2.3.1.26

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

8-14

Subventions

Organisme : Japan Society for the Promotion of Science (JSPS)
ID : JP26253009
Pays : International
Organisme : Japan Society for the Promotion of Science (JSPS)
ID : 15K07417
Pays : International

Auteurs

Takashi Fukuda (T)

Laboratory of Microbial Chemistry, Graduate School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan.
Department of Fisheries, Faculty of Agriculture, Agricultural Technology and Innovation Research Institute, Kinki University, 3327-204 Nakamachi, Nara, 631-8505, Japan.

Takun Furukawa (T)

Laboratory of Microbial Chemistry, Graduate School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan.

Keisuke Kobayashi (K)

Laboratory of Microbial Chemistry, Graduate School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan.
Medicinal Research Laboratories, School of Pharmacy, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan.

Kenichiro Nagai (K)

Medicinal Research Laboratories, School of Pharmacy, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan.

Ryuji Uchida (R)

Laboratory of Microbial Chemistry, Graduate School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan.
Department of Natural Product Chemistry, Tohoku Medical and Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai, Miyagi, 981-8558, Japan.

Hiroshi Tomoda (H)

Laboratory of Microbial Chemistry, Graduate School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan. tomodah@pharm.kitasato-u.ac.jp.
Medicinal Research Laboratories, School of Pharmacy, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan. tomodah@pharm.kitasato-u.ac.jp.

Articles similaires

Evaluating the efficacy of telesurgery with dual console SSI Mantra Surgical Robotic System: experiment on animal model and clinical trials.

Sudhir Prem Srivastava, Vishwajyoti Pascual Srivastava, Avinesh Singh et al.
1.00
Robotic Surgical Procedures Animals Humans Telemedicine Models, Animal

Odour generalisation and detection dog training.

Lyn Caldicott, Thomas W Pike, Helen E Zulch et al.
1.00
Animals Odorants Dogs Generalization, Psychological Smell

FBXO22 inhibits colitis and colorectal carcinogenesis by regulating the degradation of the S2448-phosphorylated form of mTOR.

Minle Li, Xuan Chen, Pengfei Qu et al.
1.00
Animals TOR Serine-Threonine Kinases Colorectal Neoplasms Colitis Mice

Use of organic material provided by an automatic enrichment device by weaner pigs and its influence on tail lesions.

Philipp Heseker, Jeanette Probst, Stefanie Ammer et al.
1.00
Animals Tail Swine Behavior, Animal Animal Husbandry

Classifications MeSH

questionsmedicales.fr › Eucaryotes › Animaux › Helvamide, a new inhibitor of sterol...
questionsmedicales.fr › Eucaryotes › Champignons › Deuteromycota › Aspergillus › Aspergillus nidulans › Helvamide, a new inhibitor of sterol...
questionsmedicales.fr › Cellules › Cellules épithéliales › Cellules CHO › Helvamide, a new inhibitor of sterol...
questionsmedicales.fr › Eucaryotes › Animaux › Chordés › Vertébrés › Mammifères › Eutheria › Rodentia › Muridae › Arvicolinae › Cricetinae › Cricetulus › Helvamide, a new inhibitor of sterol...
questionsmedicales.fr › Actions chimiques et utilisations › Actions pharmacologiques › Mécanismes moléculaires de l'action pharmacologique › Antienzymes › Helvamide, a new inhibitor of sterol...
questionsmedicales.fr › Techniques d'investigation › Techniques de chimie analytique › Analyse spectrale › Spectroscopie par résonance magnétique › Helvamide, a new inhibitor of sterol...
questionsmedicales.fr › Phénomènes chimiques › Structure moléculaire › Helvamide, a new inhibitor of sterol...
questionsmedicales.fr › Composés hétérocycliques › Composés hétéromonocycliques › Pipérazines › Helvamide, a new inhibitor of sterol...
questionsmedicales.fr › Enzymes et coenzymes › Enzymes › Transferases › Acyltransferases › Sterol O-acyltransferase › Helvamide, a new inhibitor of sterol...