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Article

Highly N-Methylated Linear Peptides Produced by an Atypical Sponge-Derived Acremonium sp.

Supporting Info

Claudia M. Boot,^† Karen Tenney,^† Frederick A. Valeriote,^‡ and Phillip Crews*^†

Department of Chemistry and Biochemistry and Department of Ocean Sciences, University of California, Santa Cruz, California 95064, and Henry Ford Health System, Department of Internal Medicine, Division of Hematology and Oncology, Detroit, Michigan 48202

J. Nat. Prod., 2006, 69 (1), pp 83–92

DOI: 10.1021/np0503653

Publication Date (Web): January 7, 2006

†

University of California, Santa Cruz.

‡

Ford Health System.

To whom correspondence should be addressed. Tel: 831-459-2603. Fax: 831-459-2935. E-mail: phil@chemistry.ucsc.edu.

Abstract

RHM1 (1) and RHM2 (2) are highly N-methylated linear octapeptides produced by an atypical strain of Acremonium sp., cultured from a marine sponge collected in Papua New Guinea. The known peptaibiotic efrapeptin G (3) was also isolated from this fungus. The planar structures of 1 and 2 were assigned based on 1D- and 2D-NMR experiments and fragmentation patterns from ESIMS. The absolute configuration of 1 was determined via Marfey's method; the absolute configuration of 2 is proposed to be identical. Efrapeptin G (3) displayed potent cytotoxicity against murine cancer cell lines, while RHM1 (1) and RHM2 (2) showed weak cytotoxicity against murine cancer cell lines; efrapeptin G (3) and RHM1 (1) also demonstrated antibacterial activity.