A New Alkaloid From an Australian Marine Sponge, Spongosorites sp.

1994 ◽  
Vol 47 (12) ◽  
pp. 2279 ◽  
Author(s):  
S Urban ◽  
RJ Capon ◽  
JNA Hooper
Keyword(s):  
Marine Sponge ◽  
Spectroscopic Analysis ◽  
Ethanol Extract ◽  
Chemical Derivatization ◽  
Dihydro Derivative ◽  
Antibiotic Property

A specimen of a marine sponge, Spongosorites sp., collected in Port Phillip Bay, Victoria, Australia, has yielded the alkaloid (2). The structure of (2) was secured by spectroscopic analysis, chemical derivatization and synthesis of a dihydro derivative (4). The antibiotic property of the crude ethanol extract of this sponge was attributed to (2).

Cometins (A-C), New Furanosesterterpenes From an Australian Marine Sponge, Spongia sp.

1992 ◽  
Vol 45 (8) ◽  
pp. 1255 ◽  
Author(s):  
S Urban ◽  
RJ Capon
Keyword(s):  
Marine Sponge ◽  
Spectroscopic Analysis ◽  
Ethanol Extract ◽  
Chemical Derivatization ◽  
Tetronic Acid ◽  
Antibiotic Property ◽  
Great Australian Bight

The known marine furanosesterterpene furospinosulin-1 (1), together with three new furanosesterterpenes, namely cometin-A (2), cometin-B (3) and cometin-C (4), were isolated from a marine sponge, Spongia sp., collected during commercial trawling operations in the Great Australian Bight. The structures of these metabolites were determined by detailed spectroscopic analysis and chemical derivatization . The antibiotic property of the crude ethanol extract of this sponge was attributed solely to the furanosesterterpene tetronic acid cometin -A (2).

Norterpene Dienes From an Australian Marine Sponge Latrunculia brevis

1991 ◽  
Vol 44 (1) ◽  
pp. 77 ◽  
Author(s):  
MS Butler ◽  
RJ Capon
Keyword(s):  
Marine Sponge ◽  
Spectroscopic Analysis ◽  
Methyl Esters ◽  
Chemical Derivatization

The norditerpene diene acid (4) and norsesterterpene diene acid (5), along with their corresponding methyl esters (6) and (7), were isolated from an Australian marine sponge, Latrunculia brevis, and their structures determined by detailed spectroscopic analysis, chemical derivatization and degradation. Comment is made on the possible intermediacy of dienes such as (4)-(7) in the biosynthesis of norterpene cyclic peroxides, common to other Latrunculia species from the same locality.

Lamellarins Q and R: New Aromatic Metabolites From an Australian Marine Sponge, Dendrilla cactos

1995 ◽  
Vol 48 (8) ◽  
pp. 1491 ◽  
Author(s):  
S Urban ◽  
L Hobbs ◽  
JNA Hooper ◽  
RJ Capon
Keyword(s):  
Marine Sponge ◽  
Spectroscopic Analysis ◽  
New South ◽  
New South Wales ◽  
Chemical Derivatization ◽  
South Wales

A specimen of Dendrilla cactos collected off the coast of New South Wales, Australia, has yielded two new alkaloids, lamellarins Q (19) and R (20), the structures of which were secured by spectroscopic analysis and by chemical derivatization.

Isopalinurin: a Mild Protein Phosphatase Inhibitor From a Southern Australian Marine Sponge, Dysidea sp.

1993 ◽  
Vol 46 (8) ◽  
pp. 1291 ◽  
Author(s):  
L Murray ◽  
ATR Sim ◽  
JAP Rostas ◽  
RJ Capon
Keyword(s):  
Marine Sponge ◽  
Protein Phosphatase ◽  
Spectroscopic Analysis ◽  
Ethanol Extract ◽  
Antibiotic Activity ◽  
Tetronic Acid ◽  
Phosphatase Inhibitor ◽  
Protein Phosphatase Inhibitor

A new sesterterpene tetronic acid, isopalinurin (1), has been isolated from an Australian marine sponge, Dysidea sp., collected in Bass Strait. Isopalinurin (1) was identified as the agent responsible for the antibiotic activity and protein phosphatase inhibitory properties exhibited by the crude ethanol extract, and its structure was secured by detailed spectroscopic analysis.

cis-3-Hydroxy-N-methyl-L-proline: a New Amino Acid from a Southern Australian Marine Sponge, Dendrilla sp.

1998 ◽  
Vol 51 (2) ◽  
pp. 169 ◽  
Author(s):  
Robert J. Capon ◽  
Simon P. B. Ovenden ◽  
Tim Dargaville
Keyword(s):  
Amino Acid ◽  
Marine Sponge ◽  
Spectroscopic Analysis ◽  
Natural Abundance ◽  
Chemical Derivatization ◽  
Great Australian Bight ◽  
Very High

A specimen of the sponge Dendrilla sp. collected during commercial trawling operations in the Great Australian Bight, Australia, analyses for a very high natural abundance of the new amino acid cis-3-hydroxy-N-methyl-L-proline (1). The complete stereostructure for (1) was determined by spectroscopic analysis and chemical derivatization.

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.

scholarly journals Chemical Derivatization and Characterization of Novel Antitrypanosomals for African Trypanosomiasis

Molecules ◽  
2021 ◽  
Vol 26 (15) ◽  
pp. 4488
Author(s):  
Aboagye Kwarteng Dofuor ◽  
Temitayo Samson Ademolue ◽  
Cynthia Mmalebna Amisigo ◽  
Kwaku Kyeremeh ◽  
Theresa Manful Gwira
Keyword(s):  
Structural Modification ◽  
Spectroscopic Analysis ◽  
Microscopic Analysis ◽  
The Novel ◽  
Chemical Derivatization ◽  
African Trypanosomiasis ◽  
Chemical Structures ◽  
Normal Ratio

The search for novel antitrypanosomals and the investigation into their mode of action remain crucial due to the toxicity and resistance of commercially available antitrypanosomal drugs. In this study, two novel antitrypanosomals, tortodofuordioxamide (compound 2) and tortodofuorpyramide (compound 3), were chemically derived from the natural N-alkylamide tortozanthoxylamide (compound 1) through structural modification. The chemical structures of these compounds were confirmed through spectrometric and spectroscopic analysis, and their in vitro efficacy and possible mechanisms of action were, subsequently, investigated in Trypanosoma brucei (T. brucei), one of the causative species of African trypanosomiasis (AT). The novel compounds 2 and 3 displayed significant antitrypanosomal potencies in terms of half-maximal effective concentrations (EC50) and selectivity indices (SI) (compound 1, EC50 = 7.3 μM, SI = 29.5; compound 2, EC50 = 3.2 μM, SI = 91.3; compound 3, EC50 = 4.5 μM, SI = 69.9). Microscopic analysis indicated that at the EC50 values, the compounds resulted in the coiling and clumping of parasite subpopulations without significantly affecting the normal ratio of nuclei to kinetoplasts. In contrast to the animal antitrypanosomal drug diminazene, compounds 1, 2 and 3 exhibited antioxidant absorbance properties comparable to the standard antioxidant Trolox (Trolox, 0.11 A; diminazene, 0.50 A; compound 1, 0.10 A; compound 2, 0.09 A; compound 3, 0.11 A). The analysis of growth kinetics suggested that the compounds exhibited a relatively gradual but consistent growth inhibition of T. brucei at different concentrations. The results suggest that further pharmacological optimization of compounds 2 and 3 may facilitate their development into novel AT chemotherapy.

scholarly journals Two New Thyminenol Derivatives from the Marine Sponge Haliclona sp

2014 ◽  
Vol 9 (4) ◽  
pp. 1934578X1400900
Author(s):  
Bin Wang ◽  
Yaocai Lin ◽  
Yinning Chen ◽  
Riming Huang
Keyword(s):  
Marine Sponge ◽  
Spectroscopic Analysis

Investigation of the marine sponge Haliclona sp. led to the isolation of two new thyminenol derivatives, named cis-thyminenol (1) and trans-thyminenol (2). The structures of the new isolates were elucidated on the basis of extensive spectroscopic analysis.

A New Furanoditerpene From a Southern Australian Marine Sponge, Thorectandra choanoides

1995 ◽  
Vol 48 (11) ◽  
pp. 1903 ◽  
Author(s):  
S Urban ◽  
RJ Capon
Keyword(s):  
Marine Sponge ◽  
Spectroscopic Analysis

A specimen of the marine sponge Thorectandra choanoides from Bass Strait, Australia, has yielded the new furanoditerpene (7), the structure of which was secured by spectroscopic analysis.

scholarly journals Cytotoxic Polyketides from the Marine Sponge-Derived Fungus Pestalotiopsis heterocornis XWS03F09

Molecules ◽  
2019 ◽  
Vol 24 (14) ◽  
pp. 2655 ◽  
Author(s):  
Lei ◽  
Lei ◽  
Zhou ◽  
Hu ◽  
Niu ◽  
...  
Keyword(s):  
Marine Sponge ◽  
Spectroscopic Analysis ◽  
Fermentation Broth ◽  
Human Cancer ◽  
Optical Rotation ◽  
Cytotoxic Activities ◽  
Human Cancer Cell Lines ◽  
Chemical Structures ◽  
Ic50 Values ◽  
New Compounds

Four new compounds, including two new polyketides, heterocornols M and N (1, 2), and a pair of epimers, heterocornols O and P (3, 4), were isolated from the fermentation broth of the marine sponge-derived fungus Pestalotiopsis heterocornis XWS03F09, together with three known compounds (5–7). The new chemical structures were established on the basis of a spectroscopic analysis, optical rotation, experimental and calculated electronic circular dichroism (ECD). All of the compounds (1–7) were evaluated for their cytotoxic activities, and heterocornols M-P (1–4) exhibited cytotoxicities against four human cancer cell lines with IC50 values of 20.4–94.2 μM.

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