Thiodiketopiperazines with two spirocyclic centers extracted from Botryosphaeria mamane, an endophytic fungus isolated from Bixa orellana L.
Antineoplastic Agents
/ chemistry
Ascomycota
/ chemistry
Bixaceae
/ microbiology
Caco-2 Cells
Cell Line
Circular Dichroism
Crystallography, X-Ray
Diketopiperazines
/ chemistry
Drug Screening Assays, Antitumor
Endophytes
/ chemistry
HT29 Cells
HeLa Cells
Hep G2 Cells
Humans
Magnetic Resonance Spectroscopy
Molecular Structure
Bixa orellana L. (Bixaceae)
Botryosphaeria mamane D.E. Gardner (Botryosphaeriaceae)
Cytotoxic activity
Thiodiketopiperazine
Journal
Phytochemistry
ISSN: 1873-3700
Titre abrégé: Phytochemistry
Pays: England
ID NLM: 0151434
Informations de publication
Date de publication:
Feb 2019
Feb 2019
Historique:
received:
30
07
2018
revised:
08
11
2018
accepted:
09
11
2018
pubmed:
24
12
2018
medline:
23
1
2019
entrez:
22
12
2018
Statut:
ppublish
Résumé
Three thiodiketopiperazines, botryosulfuranols A-C (1-3) were isolated from the endophytic fungus Botryosphaeria mamane. The three compounds present sulfur atoms on α- and β-positions of phenylalanine derived residues and unprecedented two spirocyclic centers at C-4 and C-2'. Their planar structures were determined by spectroscopic analysis and absolute configurations were achieved by X-ray diffraction analysis and ECD and NMR chemical shifts calculations. Botryosulfuranol A (1) was the most cytotoxic compound against four cancer cell lines (HT-29, HepG2, Caco-2, HeLa) and two healthy cell lines (IEC6, Vero) highlighting the importance of an electrophilic center for cell growth inhibition.
Identifiants
pubmed: 30576967
pii: S0031-9422(18)30397-2
doi: 10.1016/j.phytochem.2018.11.007
pii:
doi:
Substances chimiques
Antineoplastic Agents
0
Diketopiperazines
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
142-148Informations de copyright
Copyright © 2018 Elsevier Ltd. All rights reserved.