Cytotoxic Veraguamides, Alkynyl Bromide-Containing Cyclic Depsipeptides from the Marine Cyanobacterium cf. <i>Oscillatoria margaritifera</i>

Mevers, Emily; Liu, Wei-Ting; Engene, Niclas; Mohimani, Hosein; Byrum, Tara; Pevzner, Pavel A.; Dorrestein, Pieter C.; Spadafora, Carmenza; Gerwick, William H.

doi:10.1021/np200077f

Cited by 99 publications

(79 citation statements)

References 35 publications

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“…47 Cells were added at 3.33 × 10 4 cells/mL in Roswell Park Memorial Institute (RPMI) 1640 medium with fetal bovine serum (FBS) and 1% penicillin/streptomycin, compounds added in DMSO and then incubated for 48 h before staining with MTT (1 mg/mL, 37 °C, 25 min). In brief, the medium was aspirated and the cells resuspended in 100 μL DMSO to solubilize the formazan dye.…”

Section: Methodsmentioning

confidence: 99%

A Maldiisotopic Approach to Discover Natural Products: Cryptomaldamide, a Hybrid Tripeptide from the Marine Cyanobacterium Moorea producens

Kinnel

Esquenazi²,

Leão³

et al. 2017

J. Nat. Prod.

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Genome sequencing of microorganisms has revealed a greatly increased capacity for natural products biosynthesis than was previously recognized from compound isolation efforts alone. Hence, new methods are needed for the discovery and description of this hidden secondary metabolite potential. Here we show that provision of heavy nitrogen 15N-nitrate to marine cyanobacterial cultures followed by single filament MALDI analysis over a period of days was highly effective in identifying a new natural product with an exceptionally high nitrogen content. The compound, named cryptomaldamide, was subsequently isolated using MS to guide the purification process, and its structure determined by 2D NMR and other spectroscopic and chromatographic methods. Bioinformatic analysis of the draft genome sequence identified a 28.7 kB gene cluster which putatively encodes for cryptomaldamide biosynthesis. Notably, an amidinotransferase is proposed to initiate the biosynthetic process by transferring an amidino group from arginine to serine to produce the first residue to be incorporated by the hybrid NRPS-PKS pathway. The maldiisotopic approach presented here is thus demonstrated to provide an orthogonal method by which to discover novel chemical diversity from Nature.

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Section: Methodsmentioning

confidence: 99%

A Maldiisotopic Approach to Discover Natural Products: Cryptomaldamide, a Hybrid Tripeptide from the Marine Cyanobacterium Moorea producens

Kinnel

Esquenazi²,

Leão³

et al. 2017

J. Nat. Prod.

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“…Better knowledge of the behavior of these interactions could bring additional tools in crystal engineering and in material design, as well as for efficient and fruitful drug design. Indeed, terminal alkynes [43,44] and haloalkynes [45][46][47] are biologically important classes of molecules. …”

Section: Introductionmentioning

confidence: 99%

Isomorphous Crystals from Diynes and Bromodiynes Involved in Hydrogen and Halogen Bonds

et al. 2016

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Isomorphous crystals of two diacetylene derivatives with carbamate functionality (BocNH-CH 2 -diyne-X, where X = H or Br) have been obtained. The main feature of these structures is the original 2D arrangement (as supramolecular sheets or walls) in which the H bond and halogen bond have a prominent effect on the whole architecture. The two diacetylene compounds harbor neighboring carbamate (Boc protected amine) and conjugated alkyne functionalities. They differ only by the nature of the atom located at the penultimate position of the diyne moiety, either a hydrogen atom or a bromine atom. Both of them adopt very similar 2D wall organizations with antiparallel carbamates (as in antiparallel beta pleated sheets). Additional weak interactions inside the same walls between molecular bricks are H bond interactions (diyne-H¨¨¨O=C) or halogen bond interactions (diyne-Br¨¨¨O=C), respectively. Based on crystallographic atom coordinates, DFT (B3LYP/6-31++G(d,p)) and DFT (M06-2X/6-31++G(d,p)) calculations were performed on these isostructural crystals to gain insight into the intermolecular interactions.

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“…Such dd-ITe was used to investigate structures of intact polar lipids of microbes found in two regions in an artesian sulfur-rich spring source [37]. DD-ITe was used for structural analyses of seven vergauamide compounds in marine cyanobacteria, using a maximum MS 3 depth [38]. Non-genotoxic carcinogens in rats and lipid species were also structurally elucidated and confirmed using dd-ITe [39].…”

Section: Msn Data-acquisition Methodsmentioning

confidence: 99%

Using fragmentation trees and mass spectral trees for identifying unknown compounds in metabolomics

Vaniya

Fiehn

2015

TrAC Trends in Analytical Chemistry

126

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Identification of unknown metabolites is the bottleneck in advancing metabolomics, leaving interpretation of metabolomics results ambiguous. The chemical diversity of metabolism is vast, making structure identification arduous and time consuming. Currently, comprehensive analysis of mass spectra in metabolomics is limited to library matching, but tandem mass spectral libraries are small compared to the large number of compounds found in the biosphere, including xenobiotics. Resolving this bottleneck requires richer data acquisition and better computational tools. Multi-stage mass spectrometry (MSn) trees show promise to aid in this regard. Fragmentation trees explore the fragmentation process, generate fragmentation rules and aid in sub-structure identification, while mass spectral trees delineate the dependencies in multi-stage MS of collision-induced dissociations. This review covers advancements over the past 10 years as a tool for metabolite identification, including algorithms, software and databases used to build and to implement fragmentation trees and mass spectral annotations.

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Cytotoxic Veraguamides, Alkynyl Bromide-Containing Cyclic Depsipeptides from the Marine Cyanobacterium cf. Oscillatoria margaritifera

Cited by 99 publications

References 35 publications

A Maldiisotopic Approach to Discover Natural Products: Cryptomaldamide, a Hybrid Tripeptide from the Marine Cyanobacterium Moorea producens

A Maldiisotopic Approach to Discover Natural Products: Cryptomaldamide, a Hybrid Tripeptide from the Marine Cyanobacterium Moorea producens

Isomorphous Crystals from Diynes and Bromodiynes Involved in Hydrogen and Halogen Bonds

Using fragmentation trees and mass spectral trees for identifying unknown compounds in metabolomics

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