Journal
TETRAHEDRON
Volume 67, Issue 30, Pages 5461-5468Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.05.066
Keywords
Chevalones; Aszonapyrone; Eurochevalierine; Meroterpenoids; Antimalarial; Antimycobacterial; Anticancer; Eurotium chevalieri
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Funding
- Bioresources Research Network (BRN) of the National Center for Genetic Engineering and Biotechnology (BIOTEC) [BRN 001 G-51]
- Higher Education Research Promotion and National Research University of Thailand
- Office of the Higher Education Commission through Khon Kaen University
- Center for Innovation in Chemistry (PERCH-CIC)
- Office of the Higher Education Commission
- Mahidol University under the National Research Universities Initiative
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Five new meroterpenoids, chevalones A-D (1-4), aszonapyrone B (8), and a new sequiterpene alkaloid, eurochevalierine (5), together with four known compounds, sequiterpene (6), terpenoid pyrrolo-benzoxazine named CJ-12662 (7), meroterpenoid, aszonapyrone A (9), and ergosterol were isolated from the fungus Eurotium chevalieri. The structures were established on the basis of spectroscopic evidence. The configurations of 1 and 5 were determined by X-ray analysis. The biosynthetic pathway of 1-3, 8, and 9 were proposed. Chemical transformation of aszonapyrone A (9) was also studied. Compounds 4, 5, and 7 exhibited antimalarial activity against Plasmodium falciparum, while 3, 5, and 7 showed anti-mycobacterial activity against Mycobacterium tuberculosis. In addition, compounds 2-7 showed cytotoxicity against cancer cell lines. (C) 2011 Elsevier Ltd. All rights reserved.
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