Isocoumarindole A, a Chlorinated Isocoumarin and Indole Alkaloid Hybrid Metabolite from an Endolichenic Fungus Aspergillus sp.

Aspergillus / chemistry Diketopiperazines / chemistry Fungi Halogenation Indole Alkaloids / chemistry Isocoumarins / chemistry Molecular Structure Peptide Synthases / chemistry

Journal

Organic letters
ISSN: 1523-7052
Titre abrégé: Org Lett
Pays: United States
ID NLM: 100890393

Informations de publication

Date de publication:
01 03 2019
Historique:
pubmed: 21 2 2019
medline: 30 7 2019
entrez: 21 2 2019
Statut: ppublish

Résumé

Isocoumarindole A (1), a novel polyketide synthetase-nonribosomal peptide synthetase (PKS-NRPS) hybrid metabolite, was isolated from the endolichenic fungus Aspergillus sp. CPCC 400810. The structure of isocoumarindole A (1) was featured by an unprecedented skeleton containing chlorinated isocoumarin and indole diketopiperazine alkaloid moieties linked by a carbon-carbon bond, which was determined by a combination of spectroscopic analyses, Marfey's method, and calculations of NMR chemical shifts, ECD spectra, and optical rotation values. Isocoumarindole A showed significant cytotoxicity and mild antifungal activities.

Identifiants

DOI: 10.1021/acs.orglett.9b00385 PMID: 30785290
pubmed: 30785290
doi: 10.1021/acs.orglett.9b00385
doi:

Substances chimiques

Diketopiperazines 0
Indole Alkaloids 0
Isocoumarins 0
Peptide Synthases EC 6.3.2.-
non-ribosomal peptide synthase EC 6.3.2.-

Types de publication

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

Langues

eng

Pagination

1530-1533

Auteurs

Minghua Chen (M)

NHC Key Laboratory for Microbial Drug Bioengeering, Institute of Medicinal Biotechnology , Chinese Academy of Medical Sciences and Peking Union Medical College , Beijing 100050 , People's Republic of China.
Key Laboratory for Uighur Medicine , Institute of Materia Medica of Xinjiang Uygur Autonomous Region , Urumqi 830004 , People's Republic of China.
ORCID: 0000-0001-5634-4599

Renzhong Wang (R)

NHC Key Laboratory for Microbial Drug Bioengeering, Institute of Medicinal Biotechnology , Chinese Academy of Medical Sciences and Peking Union Medical College , Beijing 100050 , People's Republic of China.
Department of Natural Medicinal Chemistry, School of Traditional Chinese Pharmacy , China Pharmaceutical University , Nanjing 210009 , People's Republic of China.

Wuli Zhao (W)

NHC Key Laboratory for Microbial Drug Bioengeering, Institute of Medicinal Biotechnology , Chinese Academy of Medical Sciences and Peking Union Medical College , Beijing 100050 , People's Republic of China.

Liyan Yu (L)

NHC Key Laboratory for Microbial Drug Bioengeering, Institute of Medicinal Biotechnology , Chinese Academy of Medical Sciences and Peking Union Medical College , Beijing 100050 , People's Republic of China.
ORCID: 0000-0002-8861-9806

Conghui Zhang (C)

NHC Key Laboratory for Microbial Drug Bioengeering, Institute of Medicinal Biotechnology , Chinese Academy of Medical Sciences and Peking Union Medical College , Beijing 100050 , People's Republic of China.

Shanshan Chang (S)

NHC Key Laboratory for Microbial Drug Bioengeering, Institute of Medicinal Biotechnology , Chinese Academy of Medical Sciences and Peking Union Medical College , Beijing 100050 , People's Republic of China.

Yan Li (Y)

NHC Key Laboratory for Microbial Drug Bioengeering, Institute of Medicinal Biotechnology , Chinese Academy of Medical Sciences and Peking Union Medical College , Beijing 100050 , People's Republic of China.

Tao Zhang (T)

NHC Key Laboratory for Microbial Drug Bioengeering, Institute of Medicinal Biotechnology , Chinese Academy of Medical Sciences and Peking Union Medical College , Beijing 100050 , People's Republic of China.

Jianguo Xing (J)

Key Laboratory for Uighur Medicine , Institute of Materia Medica of Xinjiang Uygur Autonomous Region , Urumqi 830004 , People's Republic of China.

Maoluo Gan (M)

NHC Key Laboratory for Microbial Drug Bioengeering, Institute of Medicinal Biotechnology , Chinese Academy of Medical Sciences and Peking Union Medical College , Beijing 100050 , People's Republic of China.
ORCID: 0000-0002-3089-8654

Feng Feng (F)

Department of Natural Medicinal Chemistry, School of Traditional Chinese Pharmacy , China Pharmaceutical University , Nanjing 210009 , People's Republic of China.

Shuyi Si (S)

NHC Key Laboratory for Microbial Drug Bioengeering, Institute of Medicinal Biotechnology , Chinese Academy of Medical Sciences and Peking Union Medical College , Beijing 100050 , People's Republic of China.

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Classifications MeSH

questionsmedicales.fr › Eucaryotes › Champignons › Deuteromycota › Aspergillus › Isocoumarindole A, a Chlorinated Isocoumarin...
questionsmedicales.fr › Composés hétérocycliques › Composés hétéromonocycliques › Pipérazines › Pipérazinediones › Isocoumarindole A, a Chlorinated Isocoumarin...
questionsmedicales.fr › Eucaryotes › Champignons › Isocoumarindole A, a Chlorinated Isocoumarin...
questionsmedicales.fr › Métabolisme › Halogénation › Isocoumarindole A, a Chlorinated Isocoumarin...
questionsmedicales.fr › Composés hétérocycliques › Composés hétérocycliques à cycles fusionnés › Composés hétérobicycliques › Indolizine › Indolizidines › Alcaloïdes indoliques › Isocoumarindole A, a Chlorinated Isocoumarin...
questionsmedicales.fr › Composés hétérocycliques › Composés hétérocycliques à cycles fusionnés › Composés hétérobicycliques › Benzopyranes › Coumarines › Isocoumarines › Isocoumarindole A, a Chlorinated Isocoumarin...
questionsmedicales.fr › Phénomènes chimiques › Structure moléculaire › Isocoumarindole A, a Chlorinated Isocoumarin...
questionsmedicales.fr › Enzymes et coenzymes › Enzymes › Ligases › Carbon-nitrogen ligases › Amino-acid ligases › Isocoumarindole A, a Chlorinated Isocoumarin...