Targeted solid phase fermentation of the soil dwelling fungus Gymnascella dankaliensis yields new brominated tyrosine-derived alkaloids

Hao Wang; Haofu Dai; Christian Heering; Christoph Janiak; Wenhan Lin; Raha S. Orfali; Werner E. G. Müller; Zhen Liu; Peter Proksch

doi:10.1039/C6RA14554J

Targeted solid phase fermentation of the soil dwelling fungus Gymnascella dankaliensis yields new brominated tyrosine-derived alkaloids

Hao Wang,^a Haofu Dai,^b Christian Heering,^c Christoph Janiak,^c Wenhan Lin,^d Raha S. Orfali,^e Werner E. G. Müller,^f Zhen Liu*^a and Peter Proksch*^a

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* Corresponding authors

^a Institute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine-Universität Düsseldorf, Universitätsstrasse 1, 40225 Düsseldorf, Germany
E-mail: zhenfeizi0@sina.com, proksch@uni-duesseldorf.de

^b Key Laboratory of Biology and Genetic Resources of Tropical Crops, Ministry of Agriculture, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, China

^c Institute of Inorganic and Structural Chemistry, Heinrich-Heine-University Düsseldorf, Universitätsstrasse 1, 40225 Düsseldorf, Germany

^d State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191, China

^e Department of Pharmacognosy, Faculty of Pharmacy, King Saud University, Riyadh, Saudi Arabia

^f Institut für Physiologische Chemie, Universitätsmedizin der Johannes Gutenberg-Universität Mainz, Duesbergweg 6, 55128 Mainz, Germany

Abstract

Seven new brominated tyrosine-derived alkaloids, gymnastatins T–Y (1–6) and dankastatin D (7), together with three known likewise brominated analogues gymnastatins I–K (8–10) were isolated from the soil fungus Gymnascella dankaliensis through fermentation on solid rice medium following addition of NaBr. None of these compounds were detected when the fungus was cultured on rice that either lacked NaBr or that contained NaCl instead, indicating a remarkable plasticity of the fungal secondary metabolism. All structures were elucidated on the basis of one and two dimensional NMR spectroscopic analyses and MS data. The absolute configuration of the new gymnastatin T (1) was determined by X-ray crystallographic data. All isolated alkaloids showed potent to moderate cytotoxicity against the L5178Y mouse lymphoma cell line with IC₅₀ values ranging from 0.078 to 14.1 μM.

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Publication details

The article was received on 05 Jun 2016, accepted on 19 Aug 2016 and first published on 30 Aug 2016

Article type: Paper

DOI: 10.1039/C6RA14554J

Citation: RSC Adv., 2016,6, 81685-81693

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Targeted solid phase fermentation of the soil dwelling fungus Gymnascella dankaliensis yields new brominated tyrosine-derived alkaloids

H. Wang, H. Dai, C. Heering, C. Janiak, W. Lin, R. S. Orfali, W. E. G. Müller, Z. Liu and P. Proksch, RSC Adv., 2016, 6, 81685
DOI: 10.1039/C6RA14554J
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Targeted solid phase fermentation of the soil dwelling fungus Gymnascella dankaliensis yields new brominated tyrosine-derived alkaloids

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Targeted solid phase fermentation of the soil dwelling fungus Gymnascella dankaliensis yields new brominated tyrosine-derived alkaloids

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