9-(5'-Deoxy-5'-thio-β-D-xylofuranosyl)adenine Disulfide from the Southern Australian Marine Sponge Trachycladus laevispirulifer: the First Natural Occurrence of a Nucleoside Disulfide

2010 ◽  
Vol 63 (6) ◽  
pp. 873 ◽  
Author(s):  
Chongsheng Peng ◽  
G. M. Kamal B. Gunaherath ◽  
Andrew M. Piggott ◽  
Zeinab Khalil ◽  
Melissa Conte ◽  
...  
Keyword(s):  
Marine Sponge ◽  
Structure Elucidation ◽  
Spectroscopic Analysis ◽  
Chemical Fractionation ◽  
Natural Occurrence ◽  
Model Compounds ◽  
Anticancer Properties ◽  
Synthetic Model ◽  
Natural And Synthetic

Chemical fractionation of a southern Australian marine sponge, Trachycladus laevispirulifer, yielded 9-(5′-deoxy-5′-thio-β-d-xylofuranosyl)adenine disulfide as the first recorded natural occurrence of a nucleoside disulfide, and only the second of a xylo-nucleoside. Structure elucidation of the disulfide was achieved by detailed spectroscopic analysis and comparison to synthetic model compounds. The antibacterial, antifungal, and anticancer properties of the disulfide are documented and the literature surrounding natural and synthetic thionucleosides is reviewed.

scholarly journals New from Old: Thorectandrin Alkaloids in a Southern Australian Marine Sponge, Thorectandra choanoides (CMB-01889)

Marine Drugs ◽  
2021 ◽  
Vol 19 (2) ◽  
pp. 97
Author(s):  
Shamsunnahar Khushi ◽  
Angela A. Salim ◽  
Ahmed H. Elbanna ◽  
Laizuman Nahar ◽  
Robert J. Capon
Keyword(s):  
Marine Sponge ◽  
Tissue Specificity ◽  
Spectroscopic Analysis ◽  
Transformation Products ◽  
Chemical Fractionation ◽  
Cancer Tissue ◽  
Michael Acceptor ◽  
Michael Acceptors ◽  
Stable Ring

Thorectandra choanoides (CMB-01889) was prioritized as a source of promising new chemistry from a library of 960 southern Australian marine sponge extracts, using a global natural products social (GNPS) molecular networking approach. The sponge was collected at a depth of 45 m. Chemical fractionation followed by detailed spectroscopic analysis led to the discovery of a new tryptophan-derived alkaloid, thorectandrin A (1), with the GNPS cluster revealing a halo of related alkaloids 1a–1n. In considering biosynthetic origins, we propose that Thorectandrachoanoides (CMB-01889) produces four well-known alkaloids, 6-bromo-1′,8-dihydroaplysinopsin (2), 6-bromoaplysinopsin (3), aplysinopsin (4), and 1′,8-dihydroaplysinopsin (10), all of which are susceptible to processing by a putative indoleamine 2,3-dioxygenase-like (IDO) enzyme to 1a–1n. Where the 1′,8-dihydroalkaloids 2 and 10 are fully transformed to stable ring-opened thorectandrins 1 and 1a–1b, and 1h–1j, respectively, the conjugated precursors 3 and 4 are transformed to highly reactive Michael acceptors that during extraction and handling undergo complete transformation to artifacts 1c–1g, and 1k–1n, respectively. Knowledge of the susceptibility of aplysinopsins as substrates for IDOs, and the relative reactivity of Michael acceptor transformation products, informs our understanding of the pharmaceutical potential of this vintage marine pharmacophore. For example, the cancer tissue specificity of IDOs could be exploited for an immunotherapeutic response, with aplysinopsins transforming in situ to Michael acceptor thorectandrins, which covalently bind and inhibit the enzyme.

Beyond Polygodial: New Drimane Sesquiterpenes From a Southern Australian Marine Sponge, Dysidea sp.

1993 ◽  
Vol 46 (8) ◽  
pp. 1255 ◽  
Author(s):  
MS Butler ◽  
RJ Capon
Keyword(s):  
Marine Sponge ◽  
Structure Elucidation ◽  
Spectroscopic Analysis ◽  
Marine Metabolites ◽  
Ecological Relationship ◽  
Chemical Correlation ◽  
The Absolute ◽  
First Time ◽  
Absolute Stereochemistry

This report describes the isolation and structure elucidation of four new drimane sesquiterpenes (14)-(17) from a southern Australian marine sponge Dysidea sp. The structures for (14)-(17) were secured by detailed spectroscopic analysis, chemical interconversion and derivatization. Also reported are the known metabolites (+)- euryfuran (7), dihydropallescensin-2 (18), (-)- pallescensin-A (19) and (-)-7-deacetoxyolepupane (6). The rare co-occurrence of two antipodes, (7) and (19), in the same specimen highlights the dangers in assigning absolute stereochemistry based on 'unproven' biosynthetic relationships. The absolute stereochemistry for (6) has been unambiguously established for the first time by chemical interconversion to (7). Furthermore, the absolute stereochemistry of the new marine metabolites listed above, (14)-(17), were determined by chemical correlation to (6). A biosynthetic and ecological relationship is proposed between the metabolites from Dysidea sp. with the known marine and terrestrial antifeedant polygodial (8). Chemical investigations are reported that support this proposition.

The Bastadins Revisited: New Chemistry From the Australian Marine Sponge Ianthella basta

1991 ◽  
Vol 44 (2) ◽  
pp. 287 ◽  
Author(s):  
MS Butler ◽  
TK Lim ◽  
RJ Capon ◽  
LS Hammond
Keyword(s):  
Great Barrier Reef ◽  
Marine Sponge ◽  
Structure Elucidation ◽  
Spectroscopic Analysis ◽  
Oxidative Cyclization ◽  
Barrier Reef ◽  
Structure Class

A specimen of Ianthella basta, collected from the Great Barrier Reef, Australia, has been found to contain the recently reported tetramer of bromotyrosine , bastadin-9 (6a), along with a new example of this structure class, bastadin-12 (9a). The structure for bastadin-12 (9a) was confirmed by detailed spectroscopic analysis and derivatization, and represents the first reported example of this structure class derived from an alternative oxidative cyclization . As earlier biosynthetic arguments to the structure elucidation of some bastadins were based on the premise that only one cyclization pathway was possible (leading to 13,32-dioxa-4,22-diazabastarane), the discovery of (9a) introduces an added dimension to the identification of new and known bastadins. Also isolated and identified as their methyl ethers were two new dimers of bromotyrosine, hemibastadin-1 (10) and hemibastadin-2 (11).

Two New Scalarane Sesterterpenes: Isoscalarafuran-A and -B, Epimeric Alcohols From a Southern Australian Marine Sponge, Spongia hispida

1993 ◽  
Vol 46 (8) ◽  
pp. 1295 ◽  
Author(s):  
R Davis ◽  
RJ Capon
Keyword(s):  
Marine Sponge ◽  
Molecular Modelling ◽  
Spectroscopic Analysis ◽  
Model Compounds ◽  
Great Australian Bight ◽  
New Metabolites

A specimen of the marine sponge Spongia hispida ( Lamarck , 1814), collected in the Great Australian Bight, has yielded the known marine sesterterpene hyrtiosal (1), together with two new scalarane sesterterpenes, isoscalarafuran-A (2) and isoscalarafuran -B (3). The structures for these two new metabolites were secured by detailed spectroscopic analysis, comparison with model compounds, and molecular modelling.

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.

Isolation and Structure Elucidation of Epipolasterol and 22,23-Dihydroepipolasterol from the Marine Sponge Epipolasis sp.

1997 ◽  
Vol 117 (4) ◽  
pp. 561-563 ◽  
Author(s):  
Russell G. Kerr ◽  
Cathy Foss ◽  
Shigeki Matsunaga ◽  
Nobuhiro Fusetani
Keyword(s):  
Marine Sponge ◽  
Structure Elucidation

YM-266183 and YM-266184, Novel Thiopeptide Antibiotics Produced by Bacillus cereus Isolated from a Marine Sponge. Part 2. Structure Elucidation.

ChemInform ◽  
2003 ◽  
Vol 34 (29) ◽  
Author(s):  
Ken-ichi Suzumura ◽  
Takako Yokoi ◽  
Masashi Funatsu ◽  
Koji Nagai ◽  
Koichi Tanaka ◽  
...  
Keyword(s):  
Bacillus Cereus ◽  
Marine Sponge ◽  
Structure Elucidation ◽  
Thiopeptide Antibiotics
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