期刊
JOURNAL OF NATURAL PRODUCTS
卷 85, 期 7, 页码 1704-1714出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.jnatprod.2c00162
关键词
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资金
- Fundacao para a Ciencia e a Tecnologia (FCT) [UIDB/04423/2020, UIDP/04423/2020, SFRH/BD/116009/2016, SFRH/BD/136367/2018]
- European Union [952374, NORTE-01-0145- FEDER-000040]
- NORTE2020
- European Regional Development Fund (ERDF)
- Fundação para a Ciência e a Tecnologia [SFRH/BD/116009/2016, SFRH/BD/136367/2018] Funding Source: FCT
In this study, two new lipoglycopeptides were discovered from the cyanobacterium Desmonostoc muscorum LEGE 12446 isolated from a cycad coralloid root. The chemical structures of the compounds were determined, and their potential role in root endosymbiosis was proposed.
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.
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