scholarly journals Halogenated volatiles from the fungusGeniculosporiumand the actinomyceteStreptomyces chartreusis

2013 ◽  
Vol 9 ◽  
pp. 2767-2777 ◽  
Author(s):  
Tao Wang ◽  
Patrick Rabe ◽  
Christian A Citron ◽  
Jeroen S Dickschat
Keyword(s):  
Natural Products ◽  
Natural Product ◽  
Structure Elucidation ◽  
Mass Spectra ◽  
Small Family ◽  
Structural Assignment ◽  
Comparison Of Mass Spectra

Two unidentified chlorinated volatilesXandYwere detected in headspace extracts of the fungusGeniculosporium. Their mass spectra pointed to the structures of a chlorodimethoxybenzene forXand a dichlorodimethoxybenzene forY. The mass spectra of some constitutional isomers forXandYwere included in our databases and proved to be very similar, thus preventing a full structural assignment. For unambiguous structure elucidation all possible constitutional isomers forXandYwere obtained by synthesis or from commercial suppliers. Comparison of mass spectra and GC retention times rigorously established the structures of the two chlorinated volatiles. Chlorinated volatiles are not very widespread, but brominated or even iodinated volatiles are even more rare. Surprisingly, headspace extracts fromStreptomyces chartreusiscontained methyl 2-iodobenzoate, a new natural product that adds to the small family of iodinated natural products.

Applied evolution: phylogeny-based approaches in natural products research

2019 ◽  
Vol 36 (9) ◽  
pp. 1295-1312 ◽  
Author(s):  
Martina Adamek ◽  
Mohammad Alanjary ◽  
Nadine Ziemert
Keyword(s):  
Natural Products ◽  
Natural Product ◽  
Structure Elucidation ◽  
Phylogenetic Analyses ◽  
Natural Product Discovery

Here we highlight how phylogenetic analyses can be used to facilitate natural product discovery and structure elucidation.

scholarly journals Isolation and Structure Elucidation of New Secondary Metabolites from New Zealand Marine Red Algae

2021 ◽  
Author(s):  
◽  
Wendy Lynne Popplewell
Keyword(s):  
Antibacterial Activity ◽  
Natural Products ◽  
New Zealand ◽  
Secondary Metabolites ◽  
Natural Product ◽  
Red Algae ◽  
Structure Elucidation ◽  
Screening Tool ◽  
Product Analysis ◽  
Algal Extracts

<p>The natural product analysis of New Zealand red algae has been neglected in recent years, and there is obvious scope for the chemical re-evaluation of New Zealand marine red algae. This study describes the isolation and structure elucidation of 12 new and eight known compounds from four different genera of red algae. To aid in this process, 34 red algae were screened in order to generate a digital HSQC spectra mask, a screening tool developed by the VUW Marine Natural Products group to identify extracts of interest for further analysis. All 34 algal extracts were screened using the HSQC mask and four extracts were identified as interesting and analysed in detail. Examination of extracts of the red algae Plocamium costatum and Ballia callitricha lead to the isolation of three known metabolites. Eleven new oxylipins, labillarides A to K, are reported from the alga Phacelocarpus labillardieri. Labillarides A to H are polyunsaturated alpha-pyrone macrocycles, all of which show similarities to the previously reported compounds isolated from southern Australian collections of the algae. Labillarides E to H are of particular interest as they represent the two diastereomeric pairs associated with variation at the C-3 and C-8 chiral centres. Labillarides I and J are related enol macrocycles while labillaride K is a furan-3-one oxylipin, all of which have biogenic significance to the macrocyclic alpha-pyrones. Labillarides A, B and I exhibit moderate cytotoxicity while labillaride C shows moderate antibacterial activity. A new nitrogenous bromophenol, colensolide A, was isolated from the alga Osmundaria colensoi along with five known bromophenols. The presence of nitrogen-containing sidechains in bromophenols is unusual but not unprecedented. The bicyclic nitrogenous moiety observed in colensolide A is proposed to be of histidine origin. Several of the known bromophenols exhibit antibacterial activity and one shows moderate cytotoxicity.</p>

scholarly journals Isolation and Structure Elucidation of New Secondary Metabolites from New Zealand Marine Red Algae

2021 ◽  
Author(s):  
◽  
Wendy Lynne Popplewell
Keyword(s):  
Antibacterial Activity ◽  
Natural Products ◽  
New Zealand ◽  
Secondary Metabolites ◽  
Natural Product ◽  
Red Algae ◽  
Structure Elucidation ◽  
Screening Tool ◽  
Product Analysis ◽  
Algal Extracts

<p>The natural product analysis of New Zealand red algae has been neglected in recent years, and there is obvious scope for the chemical re-evaluation of New Zealand marine red algae. This study describes the isolation and structure elucidation of 12 new and eight known compounds from four different genera of red algae. To aid in this process, 34 red algae were screened in order to generate a digital HSQC spectra mask, a screening tool developed by the VUW Marine Natural Products group to identify extracts of interest for further analysis. All 34 algal extracts were screened using the HSQC mask and four extracts were identified as interesting and analysed in detail. Examination of extracts of the red algae Plocamium costatum and Ballia callitricha lead to the isolation of three known metabolites. Eleven new oxylipins, labillarides A to K, are reported from the alga Phacelocarpus labillardieri. Labillarides A to H are polyunsaturated alpha-pyrone macrocycles, all of which show similarities to the previously reported compounds isolated from southern Australian collections of the algae. Labillarides E to H are of particular interest as they represent the two diastereomeric pairs associated with variation at the C-3 and C-8 chiral centres. Labillarides I and J are related enol macrocycles while labillaride K is a furan-3-one oxylipin, all of which have biogenic significance to the macrocyclic alpha-pyrones. Labillarides A, B and I exhibit moderate cytotoxicity while labillaride C shows moderate antibacterial activity. A new nitrogenous bromophenol, colensolide A, was isolated from the alga Osmundaria colensoi along with five known bromophenols. The presence of nitrogen-containing sidechains in bromophenols is unusual but not unprecedented. The bicyclic nitrogenous moiety observed in colensolide A is proposed to be of histidine origin. Several of the known bromophenols exhibit antibacterial activity and one shows moderate cytotoxicity.</p>

scholarly journals Structure elucidation and biosynthesis of fuscachelins, peptide siderophores from the moderate thermophileThermobifida fusca

2008 ◽  
Vol 105 (40) ◽  
pp. 15311-15316 ◽  
Author(s):  
Eric J. Dimise ◽  
Paul F. Widboom ◽  
Steven D. Bruner
Keyword(s):  
Natural Products ◽  
Natural Product ◽  
Gene Cluster ◽  
Structure Elucidation ◽  
Biochemical Characterization ◽  
Gene Clusters ◽  
Biologically Active ◽  
Biosynthetic Gene ◽  
Nonribosomal Peptide

Bacteria belonging to the order Actinomycetales have proven to be an important source of biologically active and often therapeutically useful natural products. The characterization of orphan biosynthetic gene clusters is an emerging and valuable approach to the discovery of novel small molecules. Analysis of the recently sequenced genome of the thermophilic actinomyceteThermobifida fuscarevealed an orphan nonribosomal peptide biosynthetic gene cluster coding for an unknown siderophore natural product.T. fuscais a model organism for the study of thermostable cellulases and is a major degrader of plant cell walls. Here, we report the isolation and structure elucidation of the fuscachelins, siderophore natural products produced byT. fusca. In addition, we report the purification and biochemical characterization of the termination module of the nonribosomal peptide synthetase. Biochemical analysis of adenylation domain specificity supports the assignment of this gene cluster as the producer of the fuscachelin siderophores. The proposed nonribosomal peptide biosynthetic pathway exhibits several atypical features, including a macrocyclizing thioesterase that produces a 10-membered cyclic depsipeptide and a nonlinear assembly line, resulting in the unique heterodimeric architecture of the siderophore natural product.

Biosynthetic Studies on Acetosellin and Structure Elucidation of a New Acetosellin Derivative

Planta Medica ◽  
2017 ◽  
Vol 83 (12/13) ◽  
pp. 1044-1052 ◽  
Author(s):  
Peter Hufendiek ◽  
Simon Stölben ◽  
Stefan Kehraus ◽  
Nicole Merten ◽  
Henrik Harms ◽  
...  
Keyword(s):  
Natural Products ◽  
Drug Discovery ◽  
Natural Product ◽  
Structure Elucidation ◽  
13C Labeling ◽  
Fungal Strains ◽  
Epicoccum Nigrum ◽  
Marine Habitats ◽  
Biosynthetic Studies

AbstractNatural products from fungi, especially Ascomycota, play a major role in therapy and drug discovery. Fungal strains originating from marine habitats offer a new avenue for finding unusual molecular skeletons. Here, the marine-derived fungus Epicoccum nigrum (strain 749) was found to produce the azaphilonoid compounds acetosellin and 5′,6′-dihydroxyacetosellin. The latter is a new natural product. The biosynthesis of these polyketide-type compounds is intriguing, since two polyketide chains are assembled to the final product. Here we performed 13C labeling studies on solid cultures to prove this hypothesis for acetosellin biosynthesis.

scholarly journals New Deoxyenhygrolides from Plesiocystis pacifica Provide Insights into Butenolide Core Biosynthesis

Marine Drugs ◽  
2022 ◽  
Vol 20 (1) ◽  
pp. 72
Author(s):  
Joachim J. Hug ◽  
Louise Kjaerulff ◽  
Ronald Garcia ◽  
Rolf Müller
Keyword(s):  
Natural Products ◽  
Natural Product ◽  
Benzyl Alcohol ◽  
In Silico ◽  
Structure Elucidation ◽  
Product Class ◽  
Biological Functions ◽  
Biosynthetic Genes

Marine myxobacteria present a virtually unexploited reservoir for the discovery of natural products with diverse biological functions and novel chemical scaffolds. We report here the isolation and structure elucidation of eight new deoxyenhygrolides (1–8) from the marine myxobacterium Plesiocystis pacifica DSM 14875T. The herein described deoxyenhygrolides C–J (1–8) feature a butenolide core with an ethyl residue at C-3 of the γ-lactone in contrast to the previously described derivatives, deoxyenhygrolides A and B, which feature an isobutyl residue at this position. The butenolide core is 2,4-substituted with a benzyl (1, 2 and 7), benzoyl (3 and 4) or benzyl alcohol (5, 6 and 8) moiety in the 2-position and a benzylidene (1–6) or benzylic hemiketal (7 and 8) in the 4-position. The description of these new deoxyenhygrolide derivatives, alongside genomic in silico investigation regarding putative biosynthetic genes, provides some new puzzle pieces on how this natural product class might be formed by marine myxobacteria.

Computational prediction of chiroptical properties in structure elucidation of natural products

2019 ◽  
Vol 36 (7) ◽  
pp. 1005-1030 ◽  
Author(s):  
Laura Grauso ◽  
Roberta Teta ◽  
Germana Esposito ◽  
Marialuisa Menna ◽  
Alfonso Mangoni
Keyword(s):  
Natural Products ◽  
Natural Product ◽  
Structure Elucidation ◽  
Computational Prediction ◽  
Chiroptical Properties

A tutorial review aimed to introduce natural product chemists to the predictions of natural product configurations by ECD and OR calculations.

scholarly journals Isolation and Structure Elucidation of a Novel Symmetrical Macrocyclic Phthalate Hexaester

Symmetry ◽  
2021 ◽  
Vol 13 (2) ◽  
pp. 361
Author(s):  
Michiya Kamio ◽  
Weina Jiang ◽  
Hiroki Osada ◽  
Masayuki Fukuoka ◽  
Hajime Uchida ◽  
...  
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Antibacterial Activity ◽  
Magnetic Resonance ◽  
High Resolution ◽  
Natural Product ◽  
Spectroscopic Data ◽  
Structure Elucidation ◽  
Mass Spectra ◽  
Activity Test ◽  
Resolution Mass

A novel symmetrical macrocyclic phthalate hexaester (1) and a known macrocyclic phthalate tetraester (2) were isolated during a natural product-exploring program on the cyanobacterium Moorea producens. Their structures were elucidated based on spectroscopic data, including nuclear magnetic resonance and high-resolution mass spectra. In the antibacterial activity test, compounds 1 and 2 showed no bioactivity at the concentrations tested.

Structure elucidation of a proton-deficient natural product using LR-HSQMBC supported by DFT calculations

Planta Medica ◽  
2015 ◽  
Vol 81 (11) ◽  
Author(s):  
J Saurí ◽  
STS Chan ◽  
AV Buevich ◽  
KR Gustafson ◽  
RT Williamson ◽  
...  
Keyword(s):  
Dft Calculations ◽  
Natural Product ◽  
Structure Elucidation
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