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Nat Prod Res. 2019 Jan 19:1-11. doi: 10.1080/14786419.2018.1548458. [Epub ahead of print]

Isoshamixanthone: a new pyrano xanthone from endophytic Aspergillus sp. ASCLA and absolute configuration of epiisoshamixanthone.

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a Organic and Bioorganic Chemistry, Faculty of Chemistry , Bielefeld University , Bielefeld , Germany.
b Pharmacognosy Department, Faculty of Pharmacy , Helwan University , Helwan , Cairo, Egypt.
c Microbial Chemistry Department, Genetic Engineering and Biotechnology Research Division , National Research Centre , Dokki-Giza , Egypt.
d Chemistry Department, Faculty of Science , Al-Azhar University , Nasr City-Cairo , Egypt.
e Inorganic and Structural Chemistry , Bielefeld University, Department of Chemistry , Bielefeld , Germany.
f Chemistry of Natural Compounds Department, Division of Pharmaceutical Industries , National Research Centre , Dokki-Giza , Egypt.


Isoshamixanthone (1), a new stereoisomeric pyrano xanthone together with the previously known fungal metabolites, epiisoshamixanthone (2), sterigmatocystin (3), arugosin C (4), norlichexanthone (5), diorcinol (6), ergosterol and methyllinoleate, were obtained from the endophytic fungal strain Aspergillus sp. ASCLA isolated from leaf tissues of the medicinal plant Callistemon subulatus. The chemical structure of the new xanthone (1) was elucidated by extensive 1D, 2D NMR, and ESI HR mass measurements, and by comparison with literature data. The constitutions and absolute configurations of 1 and epiisoshamixanthone (2) were additionally confirmed by X-ray crystallography. Compounds 1,2 were evaluated for their potential anticancer activity using the human cervix carcinoma cell line (KB-3-1). The antimicrobial activities of the fungal extract and compounds 1,2 were studied using a panel of pathogenic microorganisms as well.


Isoshamixanthone; absolute configuration; biological activities; endophytic fungi

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