Structure and Biosynthesis of Desmamides A-C, Lipoglycopeptides from the Endophytic Cyanobacterium Desmonostoc muscorum LEGE 12446

• Type: Article in International Scientific Journal
• Date: 2022

Authors

Castelo Branco, R (Author) Other; Wenzel Storjohann, A (Author) Other; Vitor Vasconcelos (Author) FCUP; Tasdemir, D (Author) Other; Pedro N Leao (Author) Other; Freitas, S (Author) Other

Journal

Title: Journal of Natural Products

Vol. 85

Pages: 1704-1714

ISSN: 0163-3864

Publisher: American Chemical Society

Indexing

ISI Web of Knowledge - 6 Citations

Scopus - 6 Citations

Other information

Authenticus ID: P-00W-YC1

DOI: 10.1021/acs.jnatprod.2c00162

Abstract (EN): Certain cyanobacteria of the secondary metabolite-rich order Nostocales can establish permanent symbioses with a large number of cycads, by accumulating in their coralloid roots and shifting their metabolism to dinitrogen fixation. Here, we report the discovery of two new lipoglycopeptides, desmamides A (1) and B (2), together with their aglycone desmamide C (3), from the nostocalean cyanobacterium Desmonostoc muscorum LEGE 12446 isolated from a cycad (Cycas revol u t a ) coralloid root. The chemical structures of the compounds were elucidated using a combination of 1D and 2D NMR spectroscopy and mass spectrometry. The desmamides are decapeptides featuring O-glycosylation of tyrosine (in 1 and 2) and an unusual 3,5-dihydroxy-2-methyldecanoic acid residue. The biosynthesis of the desmamides was studied by substrate incubation experiments and bioinformatics. We describe herein the dsm biosynthetic gene cluster and propose it to be associated with desmamide production. The discovery of this class of very abundant (> 1.5% d.w.) bacterial lipoglycopeptides paves the way for exploration of their potential role in root endosymbiosis.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 11