Structural and stereochemical studies of hydroxyanthraquinone derivatives from the endophytic fungus Coniothyrium sp

Peng Sun, Juan Huo, T. Kurtán, Attila Mándi, S. Antus, Hua Tang, Siegfried Draeger, Barbara Schulz, Hidayat Hussain, Karsten Krohn, Weihua Pan, Yanghua Yi, Wen Zhang

Research output: Article

21 Citations (Scopus)

Abstract

Four known hydroxyanthraquinones (1-4) together with four new derivatives having a tetralone moiety, namely coniothyrinones A-D (5-8), were isolated from the culture of Coniothyrium sp., an endophytic fungus isolated from Salsola oppostifolia from Gomera in the Canary Islands. The structures of the new compounds were elucidated by detailed spectroscopic analysis and comparison with reported data. The absolute configurations of coniothyrinones A (5), B (6), and D (8) were determined by TDDFT calculations of CD spectra, allowing the determination of the absolute configuration of coniothyrinone C (7) as well. Coniothyrinones A (5), B (6), and D (8) could be used as ECD reference compounds in the determination of absolute configuration for related tetralone derivatives. This is the first report of anthraquinones and derivatives from an isolate of the genus Coniothyrium sp. These compounds showed inhibitory effects against the fungus Microbotryum violaceum, the alga Chlorella fusca, and the bacteria Escherichia coli and Bacillus megaterium.

Original languageEnglish
Pages (from-to)141-148
Number of pages8
JournalChirality
Volume25
Issue number2
DOIs
Publication statusPublished - febr. 2013

Fingerprint

Tetralones
Fungi
Salsola
Bacillus megaterium
Derivatives
Chlorella
Anthraquinones
Spectroscopic analysis
Bacilli
Algae
Spain
Escherichia coli
Bacteria

ASJC Scopus subject areas

  • Organic Chemistry
  • Analytical Chemistry
  • Drug Discovery
  • Pharmacology
  • Catalysis
  • Spectroscopy

Cite this

Structural and stereochemical studies of hydroxyanthraquinone derivatives from the endophytic fungus Coniothyrium sp. / Sun, Peng; Huo, Juan; Kurtán, T.; Mándi, Attila; Antus, S.; Tang, Hua; Draeger, Siegfried; Schulz, Barbara; Hussain, Hidayat; Krohn, Karsten; Pan, Weihua; Yi, Yanghua; Zhang, Wen.

In: Chirality, Vol. 25, No. 2, 02.2013, p. 141-148.

Research output: Article

Sun, P, Huo, J, Kurtán, T, Mándi, A, Antus, S, Tang, H, Draeger, S, Schulz, B, Hussain, H, Krohn, K, Pan, W, Yi, Y & Zhang, W 2013, 'Structural and stereochemical studies of hydroxyanthraquinone derivatives from the endophytic fungus Coniothyrium sp', Chirality, vol. 25, no. 2, pp. 141-148. https://doi.org/10.1002/chir.22128
Sun, Peng ; Huo, Juan ; Kurtán, T. ; Mándi, Attila ; Antus, S. ; Tang, Hua ; Draeger, Siegfried ; Schulz, Barbara ; Hussain, Hidayat ; Krohn, Karsten ; Pan, Weihua ; Yi, Yanghua ; Zhang, Wen. / Structural and stereochemical studies of hydroxyanthraquinone derivatives from the endophytic fungus Coniothyrium sp. In: Chirality. 2013 ; Vol. 25, No. 2. pp. 141-148.
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