Trachycladindoles H–M: Molecular Networking Guided Exploration of a Library of Southern Australian Marine Sponges

2020 ◽  
Vol 73 (4) ◽  
pp. 338 ◽  
Author(s):  
Shamsunnahar Khushi ◽  
Laizuman Nahar ◽  
Angela A. Salim ◽  
Robert J. Capon
Keyword(s):  
Chemical Analysis ◽  
Natural Product ◽  
Structure Elucidation ◽  
Spectroscopic Analysis ◽  
Marine Sponges ◽  
Single Specimen ◽  
Guided Search ◽  
Guided Exploration ◽  
Rare Class ◽  
Great Australian Bight

A global natural product social (GNPS) molecular network guided search of a library of 960 southern Australian marine sponge extracts successfully detected a deep-water Great Australian Bight sponge, Geodia sp. (CMB-01063), as a new source of a rare class of indolo-imidazole alkaloids previously believed to be unique to a single specimen of Trachycladus laevispirulifer (CMB-03397). Chemical analysis of CMB-01063 detected the known trachycladindoles A–G (1–7), and led to the isolation, characterisation, and structure elucidation of the new trachycladindoles H–M (8–13). Structures for 8–13 were assigned on the basis of detailed spectroscopic analysis, with comparison to authentic standards of 1–7.

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

Epoxy Lipids From the Australian Epiphytic Brown Alga Notheia anomala. II.

1991 ◽  
Vol 44 (6) ◽  
pp. 843 ◽  
Author(s):  
LM Murray ◽  
RA Barrow ◽  
RJ Capon
Keyword(s):  
Arachidonic Acid ◽  
Secondary Metabolite ◽  
Brown Alga ◽  
Structure Elucidation ◽  
Spectroscopic Analysis ◽  
Chemical Degradation

Continuation of a study into the chemistry of the brown alga Notheia anomala has resulted in the isolation and structure elucidation of six new C21 lipids. These include the first reported occurrence of a secondary metabolite (3), O-acylated by arachidonic acid, along with three new bisepoxy lipids (4)-(6), and two novel trisepoxy lipids (7) and (8). The structures were secured by detailed spectroscopic analysis and chemical degradation.

scholarly journals Heronapyrrole D: A case of co-inspiration of natural product biosynthesis, total synthesis and biodiscovery

2014 ◽  
Vol 10 ◽  
pp. 1228-1232 ◽  
Author(s):  
Jens Schmidt ◽  
Zeinab Khalil ◽  
Robert J Capon ◽  
Christian B W Stark
Keyword(s):  
Antibacterial Activity ◽  
Natural Products ◽  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Natural Product ◽  
Joint Effort ◽  
Natural Product Biosynthesis ◽  
New Members ◽  
Degree Of Oxidation ◽  
Rare Class

The heronapyrroles A–C have first been isolated from a marine-derived Streptomyces sp. (CMB-0423) in 2010. Structurally, these natural products feature an unusual nitropyrrole system to which a partially oxidized farnesyl chain is attached. The varying degree of oxidation of the sesquiterpenyl subunit in heronapyrroles A–C provoked the hypothesis that there might exist other hitherto unidentified metabolites. On biosynthetic grounds a mono-tetrahydrofuran-diol named heronapyrrole D appeared a possible candidate. We here describe a short asymmetric synthesis of heronapyrrole D, its detection in cultivations of CMB-0423 and finally the evaluation of its antibacterial activity. We thus demonstrate that biosynthetic considerations and the joint effort of synthetic and natural product chemists can result in the identification of new members of a rare class of natural products.

Parguerenes Revisited: New Brominated Diterpenes From the Southern Australian Marine Red Alga Laurencia Filiformis

1996 ◽  
Vol 49 (1) ◽  
pp. 19 ◽  
Author(s):  
SJ Rochfort ◽  
RJ Capon
Keyword(s):  
Natural Product ◽  
Biosynthetic Pathway ◽  
Spectroscopic Analysis ◽  
Red Alga ◽  
Biosynthetic Precursor ◽  
Chemical Correlation ◽  
New Compounds

Five new pargueranes, 15-bromoparguer-9(11)-ene-2,7,16,19-tetrol 2,7,16-triacetate (20), 15-bromoparguer-9(11)-ene-2,7,16-triol 2,7-diacetate (21), 15-bromoparguer-9(11)-ene-2,16-diol 2-acetate (22), 15-bromoparguer-9(11)-en-16-ol (23) and 15-bromoisoparguer-9(11)-en-16-ol (24), together with a plausible biosynthetic precursor, preparguerene (25), two known parguerenes , 15-bromoparguer-9(11)-ene-2,7,16,19-tetrol tetraacetate (4) and 15-bromoparguer-9(11)-ene-2,7,16-triol 2,16 diacetate (7), and the known algal metabolites (-)- aromadendrene (17), austradiol acetate (18) and austradiol diacetate (19), have been isolated from a collection of the southern Australian marine red alga Laurencia filiformis. The known synthetic parguerane 15-bromoparguer-9(11)-ene-2,7-16-triol triacetate (5) was also found for thefirst time as a natural product. In addition to securing the structures of new compounds by chemical correlation and detailed spectroscopic analysis, a lausible biosynthetic pathway has been proposed linking preparguerene, parguerene, isoparguerene and secoparguerene carbon skeletons.

scholarly journals Biological and Chemical Diversity of Marine Sponge-Derived Microorganisms over the Last Two Decades from 1998 to 2017

Molecules ◽  
2020 ◽  
Vol 25 (4) ◽  
pp. 853 ◽  
Author(s):  
Mei-Mei Cheng ◽  
Xu-Li Tang ◽  
Yan-Ting Sun ◽  
Dong-Yang Song ◽  
Yu-Jing Cheng ◽  
...  
Keyword(s):  
Natural Products ◽  
Secondary Metabolites ◽  
Natural Product ◽  
Marine Sponge ◽  
Marine Sponges ◽  
Chemical Diversity ◽  
Comprehensive Overview ◽  
Bioactive Secondary Metabolites ◽  
The Relationship ◽  
Product Chemistry

Marine sponges are well known as rich sources of biologically natural products. Growing evidence indicates that sponges harbor a wealth of microorganisms in their bodies, which are likely to be the true producers of bioactive secondary metabolites. In order to promote the study of natural product chemistry and explore the relationship between microorganisms and their sponge hosts, in this review, we give a comprehensive overview of the structures, sources, and activities of the 774 new marine natural products from sponge-derived microorganisms described over the last two decades from 1998 to 2017.

scholarly journals Natural Product Repertoire of the Genus Amphimedon

Marine Drugs ◽  
2018 ◽  
Vol 17 (1) ◽  
pp. 19 ◽  
Author(s):  
Nourhan Shady ◽  
Mostafa Fouad ◽  
Mohamed Salah Kamel ◽  
Tanja Schirmeister ◽  
Usama Abdelmohsen
Keyword(s):  
Secondary Metabolites ◽  
Natural Product ◽  
Bioactive Compounds ◽  
Biological Activities ◽  
Marine Sponges ◽  
Rich Source ◽  
Undescribed Species ◽  
Pharmacological Activities ◽  
Wide Range ◽  
Complete Survey

Marine sponges are a very attractive and rich source in the production of novel bioactive compounds. The sponges exhibit a wide range of pharmacological activities. The genus Amphimedon consists of various species, such as viridis, compressa, complanata, and terpenensis, along with a handful of undescribed species. The Amphimedon genus is a rich source of secondary metabolites containing diverse chemical classes, including alkaloids, ceramides, cerebrososides, and terpenes, with various valuable biological activities. This review covers the literature from January 1983 until January 2018 and provides a complete survey of all the compounds isolated from the genus Amphimedon and the associated microbiota, along with their corresponding biological activities, whenever applicable.

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.

Spongiaquinone Revisited: Structural and Stereochemical Studies on Marine Sesquiterpene/Quinones From a Southern Australian Marine Sponge, Spongia sp.

1993 ◽  
Vol 46 (8) ◽  
pp. 1245 ◽  
Author(s):  
RJ Capon ◽  
DR Groves ◽  
S Urban ◽  
RG Watson
Keyword(s):  
Marine Sponge ◽  
Potassium Salt ◽  
Spectroscopic Analysis ◽  
Chemical Investigation ◽  
Chiroptical Properties ◽  
Naturally Occurring ◽  
Great Australian Bight ◽  
Absolute Stereochemistry ◽  
Unambiguous Assignment

A chemical investigation of a large purple sponge, Spongia sp., from the Great Australian Bight, resulted in the isolation of a new sesquiterpene/quinone (8), together with the known compounds dehydrocyclospongiaquinone-1 (4) and spongiaquinone (2). The last compound was also isolated as the potassium salt (9), this being the first recorded account of a naturally occurring marine sesquiterpene/quinone salt. The structure for (8) was assigned by detailed spectroscopic analysis. A re-investigation into the stereostructure of spongiaquinone (2) resulted in the first unambiguous assignment of absolute stereochemistry, and uncovered the peculiar chiroptical properties of spongiaquinone (2) and its potassium salt (9).

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