Abstract
Three amino acid-derived compounds, haenamindole (1) and 2'-epi-fumiquinazolines C (2) and D (3), were isolated from cultures of a fungicolous isolate of Penicillium lanosum (MYC-1813=NRRL 66231). Compound 1 was also encountered in cultures of P. corylophilum (MYC-418=NRRL 28126). Structure elucidation of these metabolites was based mainly on high resolution mass spectrometry and NMR data analysis. Haenamindole (1) was found to be a recently reported diketopiperazine-type metabolite that incorporates an unusual β-Phe unit. Analysis of X-ray crystallographic data and the products of acid hydrolysis of 1 enabled a conclusive, slightly modified stereochemical assignment for haenamindole. Fumiquinazoline analog 2 is a new natural product, while related compound 3 has been previously reported only as a product of an in vitro enzymatic step and of a genetically engineered fungal culture. Compounds 1 and 3 showed antiinsectan activity against the fall armyworm Spodoptera frugiperda.
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Acknowledgements
We are grateful to Professors Hyuncheol Oh of Wonkwang University and Jae-Hyuk Jang of the Korea Research Institute of Bioscience and Biotechnology (KRIBB) for providing a sample of haenamindole (1), which enabled direct comparison and verification that it was identical to our own sample of 1. We also thank Ms Nicole Krausert for technical support. Financial support was provided in part by a grant from the National Science Foundation (CHE-1011847). Crystallographic data were collected through the SCrALS (Service Crystallography at Advanced Light Source) program at Beamline 11.3.1 at the Advanced Light Source (ALS), Lawrence Berkeley National Laboratory. The ALS is supported by the US Department of Energy, Office of Energy Sciences Materials Sciences Division, under contract DE-AC02-05CH11231. Technical assistance from staff of the University of Iowa NMR and MS facilities is greatly appreciated. The USDA is an equal opportunity provider and employer.
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This article is dedicated to the fond memory of the late Professor Lester Mitscher, a great scholar, teacher and Emeritus Editor of The Journal of Antibiotics.
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Hwang, I., Che, Y., Swenson, D. et al. Haenamindole and fumiquinazoline analogs from a fungicolous isolate of Penicillium lanosum. J Antibiot 69, 631–636 (2016). https://doi.org/10.1038/ja.2016.74
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DOI: https://doi.org/10.1038/ja.2016.74
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