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Planta Med 2014; 80(13): 1131-1137
DOI: 10.1055/s-0034-1382958
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Fumigaclavines D–H, New Ergot Alkaloids from Endophytic Aspergillus fumigatus

Jing Xu
1   Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, P. R. China
2   Key Laboratory of Protection and Development Utilization of Tropical Crop Germplasm Resources, Ministry of Education, Hainan University, Haikou, P. R. China
,
Yong Chun Song
1   Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, P. R. China
,
Ye Guo
1   Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, P. R. China
,
Ya Ning Mei
3   Department of Clinical Laboratory, the First Affiliated Hospital of Nanjing Medical University, Nanjing, P. R. China
,
Ren Xiang Tan
1   Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, P. R. China
› Author Affiliations
Further Information

Publication History

received 11 March 2014
revised 27 June 2014

accepted 09 July 2014

Publication Date:
15 August 2014 (online)

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Abstract

Ergot alkaloids are toxins which are produced biotechnologically on an industrial scale. The chemical investigation of endophytic Aspergillus fumigatus resulted in the isolation of five new ergot alkaloids named fumigaclavines D–H (2–6), along with three known analogues, fumigaclavine C (1), festuclavine (7), and fumigaclavine A (8). Their structures were unequivocally elucidated by extensive spectroscopic analyses in association with X-ray single-crystal diffraction. Fumigaclavines D–H are interesting clavine-type ergot alkaloids featuring a reverse prenyl moiety at C-2, with 1–4, 6, and 8 bearing additional substituents, e.g., an OH or OAc group at C-9. Compounds 2, 4, and 6–8 showed a broad spectrum of antimicrobial activity against a panel of anaerobic microorganisms, of which compounds 4 and 6 were the most active against Veillonella parvula with an MIC = 16 µg/mL compared to that (0.12 µg/mL) of tinidazole, co-assayed as a positive reference.

Key words

Aspergillus fumigates - Trichocomaceae - Cynodon dactylon - Poaceae - clavine-type ergot alkaloids - antimicrobial activity

Supporting Information

 

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