Xanthones and sesquiterpene derivatives from a marine-derived fungus Scopulariopsis sp.

Mohamed S. Elnaggar, Sherif S. Ebada, Mohamed L. Ashour, Weaam Ebrahim, Werner E G Müller, Attila Mándi, T. Kurtán, Abdelnasser Singab, Wenhan Lin, Zhen Liu, Peter Proksch

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Two new xanthone derivatives, 12-dimethoxypinselin (1) and 12-O-acetyl-AGI-B4 (2), as well as two new phenolic bisabolane-type sesquiterpenes, 11,12-dihydroxysydonic acid (15) and 1-hydroxyboivinianic acid (16), together with one new alkaloid, scopulamide (21) and one new α-pyrone derivative, scopupyrone (26), in addition to twenty-three known compounds (3-14, 17-20, 22-25, 27-29) were isolated from solid rice cultures of the marine-derived fungus Scopulariopsis sp. obtained from the Red Sea hard coral Stylophora sp. All compounds were unambiguously identified through extensive NMR spectroscopic analyses, and by comparison with the literature. Marfey's reaction was performed to determine the absolute configuration of scopulamide (21) and TDDFT-ECD calculations were used to assign the configuration of AGI-B4 (3) and scopupyrone (26). All isolated compounds were evaluated for their cytotoxicity against L5178Y mouse lymphoma cells and the structure-activity relationships were discussed.

Original languageEnglish
Pages (from-to)2411-2419
Number of pages9
JournalTetrahedron
Volume72
Issue number19
DOIs
Publication statusPublished - May 12 2016

Fingerprint

Scopulariopsis
Xanthones
Sesquiterpenes
Fungi
Pyrones
Derivatives
Indian Ocean
Anthozoa
Acids
Structure-Activity Relationship
Cytotoxicity
Alkaloids
Lymphoma
Nuclear magnetic resonance
AGI B4

Keywords

  • Cytotoxicity
  • Scopulariopsis sp.
  • Sesquiterpene
  • Structural elucidation
  • Xanthone

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Elnaggar, M. S., Ebada, S. S., Ashour, M. L., Ebrahim, W., Müller, W. E. G., Mándi, A., ... Proksch, P. (2016). Xanthones and sesquiterpene derivatives from a marine-derived fungus Scopulariopsis sp. Tetrahedron, 72(19), 2411-2419. https://doi.org/10.1016/j.tet.2016.03.073

Xanthones and sesquiterpene derivatives from a marine-derived fungus Scopulariopsis sp. / Elnaggar, Mohamed S.; Ebada, Sherif S.; Ashour, Mohamed L.; Ebrahim, Weaam; Müller, Werner E G; Mándi, Attila; Kurtán, T.; Singab, Abdelnasser; Lin, Wenhan; Liu, Zhen; Proksch, Peter.

In: Tetrahedron, Vol. 72, No. 19, 12.05.2016, p. 2411-2419.

Research output: Contribution to journalArticle

Elnaggar, MS, Ebada, SS, Ashour, ML, Ebrahim, W, Müller, WEG, Mándi, A, Kurtán, T, Singab, A, Lin, W, Liu, Z & Proksch, P 2016, 'Xanthones and sesquiterpene derivatives from a marine-derived fungus Scopulariopsis sp.', Tetrahedron, vol. 72, no. 19, pp. 2411-2419. https://doi.org/10.1016/j.tet.2016.03.073
Elnaggar MS, Ebada SS, Ashour ML, Ebrahim W, Müller WEG, Mándi A et al. Xanthones and sesquiterpene derivatives from a marine-derived fungus Scopulariopsis sp. Tetrahedron. 2016 May 12;72(19):2411-2419. https://doi.org/10.1016/j.tet.2016.03.073
Elnaggar, Mohamed S. ; Ebada, Sherif S. ; Ashour, Mohamed L. ; Ebrahim, Weaam ; Müller, Werner E G ; Mándi, Attila ; Kurtán, T. ; Singab, Abdelnasser ; Lin, Wenhan ; Liu, Zhen ; Proksch, Peter. / Xanthones and sesquiterpene derivatives from a marine-derived fungus Scopulariopsis sp. In: Tetrahedron. 2016 ; Vol. 72, No. 19. pp. 2411-2419.
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