Novel mammalian cell cycle inhibitors, cyclotroprostatins A–D, produced by Aspergillus fumigatus, which inhibit mammalian cell cycle at G2/M phase
TetrahedronPublished 1 January 1997
Cheng‐Bin Cui, Hideaki Kakeya, Hiroyuki Osada
Citations221
SJR quartileQ3
SJR score0.43
SNIP0.60
Generate an AI Snapshot to get a quick, structured summary of this paper.
Study Snapshot
ObjectiveStudy objective
MethodsResearch methodology
PopulationPopulation studied
Sample sizeSample sizes
OutcomesStudy outcomes here
ResultsStudy results comes here
LimitationsResearch study limitations comes here
A concise AI-generated summary of the paper will appear here once you click Generate AI Snapshot.
TL;DR
Spirotryprostatins A and B had a novel structural skeleton with an unique spiro ring system and inhibited the cell cycle progression of tsFT210 cells at the G2/M phase with IC50 values of 197.5 μM and 14.0 μM, respectively.
Abstract
Four new natural diketopiperazine derivatives cyclotryprostatins A (1), B (2), C (3) and D (4), were isolated as new inhibitors of the mammalian cell cycle from the secondary metabolites of Aspergillus fumigatus BM939 through a separation procedure guided by cell cycle inhibitory acitivity. The structures of 1–4 were determined by spectroscopic methods especially by detailed analyses of their 1H and 13C NMR spectra with the aid of 2D NMR techniques. Compounds 1–4 inhibited the cell cycle progression of tsFT210 cells at the G2/M phase with IC50 values of 5.6 μM (1), 19.5 μM (2). 23.4 μM (3) and 25.3 μM (4), respectively.
Keywords
MedicineBiochemistry, Genetics and Molecular Biology
Fortschritte der Chemie Organischer Naturstoffe/Fortschritte der Chemie organischer Naturstoffe/Progress in the chemistry of organic natural productsProgress in the Chemistry of Organic Natural Products 109
2,053 Citations2019A. Douglas Kinghorn, Heinz Falk +4 more
Analytica Chimica ActaCarbon-13 NMR spectroscopy
1,048 Citations1989Hans‐Otto Kalinowski, Stefan Berger +2 more
CellThe when and how of Src regulation
535 Citations1993Jonathan A. Cooper, Brian W. Howell
This essay focuses on the structures and mechanisms that confer negative regulation and discusses how inhibition is relaxed or overridden to allow activation of Src.
TetrahedronNovel mammalian cell cycle inhibitors, spirotryprostatins A and B, produced by Aspergillus fumigatus, which inhibit mammalian cell cycle at G2/M phase
518 Citations1996Cheng‐Bin Cui, Hideaki Kakeya +1 more
TetrahedronStudies in relation to biosynthesis—XLII
234 Citations1970Arthur J. Birch, J. J. Wright
Five related metabolites isolated from the mould, Penicillium brevi-compactum Dierckx, are shown to be biogenetically derived from tryptophan, proline and mevalonic acid.
The Journal of AntibioticsNovel Mammalian Cell Cycle Inhibitors, Tryprostatins A, B and Other Diketopiperazines Produced by Aspergillus fumigatus. I. Taxonomy, Fermentation, Isolation and Biological Properties.
207 Citations1996Cheng‐Bin Cui, Hideaki Kakeya +3 more
The diketopiperazines showed an inhibitory activity on the cell cycle progression of mouse tsFT210 cells in the M phase with the MIC values of 16.4 microM and 12.2 microM, respectively.
The Journal of AntibioticsNovel Mammalian Cell Cycle Inhibitors, Tryprostatins A, B and Other Diketopiperazines Produced by Aspergillus fumigatus. II. Physico-chemical Properties and Structures.
148 Citations1996Cheng‐Bin Cui, Hideaki Kakeya +1 more
The structures of tryprostatins A, B and demethoxyfumitremorgin C were determined mainly by the use of spectroscopic methods especially by detailed analyses of their 1H and 13C NMR spectra with the aid of 2D NMR techniques including pulse field gradient heteronuclear multiple-bond correlation (PFG-HMBC) spectroscopy.
TetrahedronThe structures of five diketopiperazines from Aspergillus ustus
142 Citations1973P. S. STEYN
Journal of the American Chemical SocietyStructure of verruculogen, a tremor producing peroxide from Penicillium verruculosum
110 Citations1974J. Fayos, David M. Lokensgard +3 more
Journal of the American Chemical SocietyRemarkable, enantio-divergent biogenesis of brevianamide A and B
69 Citations1989Robert M. Williams, E. KWAST +2 more
TetrahedronTotal synthesis of (+)-fumitremorgin B, its epimeric isomers, and demethoxy derivatives
61 Citations1988S. Kodato, Masako Nakagawa +3 more
Chemical and Pharmaceutical BulletinChemistry of tremorogenic metabolites. I. Fumitremorgin a from Aspergillus fumigatus.
61 Citations1980Mikio Yamazaki, Haruhiro Fujimoto +1 more
Two new indolic metabolites, fumitremorgin A and B, were isolated from the fungus Aspergillus fumigatus, and caused severe tremor and convulsion in experimental animals.
Phytochemistry12,13-Dihydroxy-fumitremorgin C from Aspergillus fumigatus
40 Citations1990Wolf‐Rainer Abraham, Hans‐Adolf Arfmann
A new fumitremorgin C was isolated from Aspergillus fumigatus DSM 790 and its structure elucidated and it was only produced under resting cell conditions.
Chemical and Pharmaceutical BulletinConstituents of a Fern, Davallia mariesii Moore. IV. Isolation and Structures of a Novel Norcarotane Sesquiterpene Glycoside, a Chromone Glucuronide, and Two Epicatechin Glycosides.
30 Citations1992Cheng‐Bin Cui, Yasuhiro Tezuka +4 more
Tetrahedron LettersThe structure of a novel nucleoside antibiotic, dapiramicin A
26 Citations1983Haruo Seto, N. OTAKE +6 more
Tetrahedron LettersApplication of long range j c-h resolved 2d spectroscopy (lrjr) in structural elucidation of natural products. The structure of oxirapentyn
22 Citations1984Haruo Seto, Kazuo Furihata +5 more