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 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 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.

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.

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.

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).

New Oxygenated Sesquiterpenes From a Southern Australian Marine Sponge, Dictyodendrilla sp.

1995 ◽  
Vol 48 (10) ◽  
pp. 1757 ◽  
Author(s):  
NH Tran ◽  
JNA Hooper ◽  
RJ Capon
Keyword(s):  
Marine Sponge ◽  
Spectroscopic Analysis ◽  
Chemical Investigation

Chemical investigation of a Dictyodendrilla sp. from Port Phillip Bay, Victoria, yielded three new oxygenated sesquiterpenes, dictyodendrillin -A (6), -B (7) and -C (8), together with the known sesquiterpene dendrolasin (9). Structures for all these metabolites were established by spectroscopic analysis.

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.

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.

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.

Alkyl and Alkenyl Resorcinols From an Australian Marine Sponge, Haliclona Sp (Haplosclerida : Haliclonidae)

1991 ◽  
Vol 44 (10) ◽  
pp. 1393 ◽  
Author(s):  
RA Barrow ◽  
RJ Capon
Keyword(s):  
Natural Products ◽  
Marine Sponge ◽  
Spectroscopic Analysis ◽  
Chemical Degradation ◽  
Plant Source ◽  
Marine Plant ◽  
Plant Sources ◽  
Structure Class

Eleven alkyl and alkenyl resorcinols have been isolated from the Australian marine sponge Haliclona sp. Three of these, (3), (5) and (10), have previously been described from Australian terrestrial and marine plant sources. The remaining eight, (13)-(20), are new natural products whose structures have been secured by a combination of spectroscopic analysis and chemical degradation. This report represents the first account of this structure class being isolated from a non-plant source.

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