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.

Lamellarins O and P: New Aromatic Metabolites From the Australian Marine Sponge Dendrilla cactos

1994 ◽  
Vol 47 (10) ◽  
pp. 1919 ◽  
Author(s):  
S Urban ◽  
MS Butler ◽  
RJ Capon
Keyword(s):  
Marine Sponge ◽  
Spectroscopic Analysis ◽  
Pyrrole Ring ◽  
Ring System ◽  
Aromatic Rings ◽  
Partial Synthesis ◽  
Structure Class

A specimen of Dendrilla cactos collected during trawling operations in Bass Strait, Australia, has yielded two new alkaloids, lamellarin-O (17) and lamellarin-P (18). Both these metabolites are examples of the lamellarin structure class, previously reported from tunicates and a mollusc; however, in these examples the pyrrole ring system is not fused to adjacent aromatic rings. The structures of (17) and (18) were secured by spectroscopic analysis and partial synthesis.

Sigmosceptrins A - C: New Norditerpenes from a Southern Australian Marine Sponge, Sigmosceptrella sp.

1997 ◽  
Vol 50 (12) ◽  
pp. 1137 ◽  
Author(s):  
Sean Bassett, ◽  
Simon P. B. Ovenden ◽  
Robert W. Gable ◽  
Robert J. Capon
Keyword(s):  
Structural Analysis ◽  
Single Crystal ◽  
Ethyl Ester ◽  
Marine Sponge ◽  
Biosynthetic Pathway ◽  
Spectroscopic Analysis ◽  
Methyl Esters ◽  
Chemical Degradation ◽  
X Ray ◽  
Great Australian Bight

A Sigmosceptrella sp. of sponge collected during trawling operations in the Great Australian Bight, Australia, has yielded a series of new norterpenes. These include a new bisnorditerpene, sigmosceptrin-A (5); two new norditerpenes, sigmosceptrin-B (14) and sigmosceptrin-C (15), isolated as their methyl esters (6) and (7) respectively; and an ethylated artefact, sigmosceptrin-B ethyl ester (8). Complete stereostructures were assigned to the sigmosceptrins by spectroscopic analysis, chemical degradation, derivatization, and by a single-crystal X-ray structural analysis. A biosynthetic pathway is proposed that requires a common biosynthetic precursor to both the sigmosceptrins and norterpene cyclic peroxides.

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).

Triterpenoid glycosides from the Northeastern Pacific marine sponge Xestospongia vanilla

1991 ◽  
Vol 69 (9) ◽  
pp. 1352-1364 ◽  
Author(s):  
Sandra A. Morris ◽  
Peter T. Northcote ◽  
Raymond J. Andersen
Keyword(s):  
Key Words ◽  
Marine Sponge ◽  
Spectroscopic Analysis ◽  
Carbon Skeleton ◽  
Chemical Degradation ◽  
Triterpenoid Glycoside ◽  
Northeastern Pacific ◽  
Triterpenoid Glycosides

Isoxestovanin A (6), xestovanin B (7), xestovanin C (8), dehydroxestovanin A (9), epidehydroxestovanin A (10), dehydroxestovanin C (11), and secodehydroxestovanin A (12), seven new triterpenoid glycosides, have been isolated from the Northeastern Pacific sponge Xestospongia vanilla. The structures of the metabolites were determined by a combination of spectroscopic analysis and chemical degradation. The aglycone of 6 has the new isoxestovanane triterpenoid carbon skeleton. Compounds 7, 8, and 11 are the first X. vanilla triterpenoid glycosides known to contain three monosaccharide subunits. Key words: triterpenoid, glycoside, sponge, Xestospongia.

The Luffarins (A-Z), Novel Terpenes From an Australian Marine Sponge, Luffariella geometrica

1992 ◽  
Vol 45 (10) ◽  
pp. 1705 ◽  
Author(s):  
MS Butler ◽  
RJ Capon
Keyword(s):  
Natural Products ◽  
Marine Sponge ◽  
Coastal Waters ◽  
Marine Natural Products ◽  
Spectroscopic Analysis ◽  
Marine Metabolites ◽  
Chemical Correlation ◽  
The Absolute ◽  
Great Australian Bight ◽  
Absolute Stereochemistry

A marine sponge, Luffariella geometrica Kirkpatrick, collected from the southern Australian coastal waters of the Great Australian Bight, has been found to contain 14 new bicyclic sesterterpenes, luffarin-A (14), -B (15), -C (16), -D (17), -E (18), -F (19), -G (20), -H (21), -I (22), -J (23), -K (24), -L (25), -M (26) and -N (27), a new bicyclic bisnorsesterterpene, luffarin-O (30), a new monocyclic sesterterpene, luffarin-P (32), six new acyclic sesterterpenes, luffarin-Q (35), -R (36), -S (37), -T (38), -U (39) and -V (40), two new diterpenes, luffarin-W (41) and -X (44), and two new bisnorditerpenes luffarin-Y (45) and -Z (46). These novel marine metabolites have been assigned structures, including stereochemistry, on the basis of detailed spectroscopic analysis, chemical correlation, derivatization, and biosynthetic considerations. Studies directed at the absolute stereochemistry of the luffarins have also permitted assignment of absolute stereochemistry to the known marine natural products (E)-neomanoalide (3), (Z)-neomanoalide (4) and dehydroambliol-A (47).

scholarly journals Cacolides: Sesterterpene Butenolides from a Southern Australian Marine Sponge, Cacospongia sp.

Marine Drugs ◽  
2018 ◽  
Vol 16 (11) ◽  
pp. 456 ◽  
Author(s):  
Shamsunnahar Khushi ◽  
Laizuman Nahar ◽  
Angela Salim ◽  
Robert Capon
Keyword(s):  
Natural Products ◽  
Chemical Analysis ◽  
Carboxylic Acids ◽  
Marine Sponge ◽  
Deep Sea ◽  
Spectroscopic Analysis ◽  
Chemical Diversity ◽  
Commercial Fishing ◽  
Southern Coast ◽  
Molecular Networking

Chemical analysis of a marine sponge, Cacospongia sp. (CMB-03404), obtained during deep sea commercial fishing activities off the southern coast of Australia, yielded an unprecedented family of sesterterpene α-methyl-γ-hydroxybutenolides, cacolides A–L (1–12), together with biosynthetically related norsesterterpene carboxylic acids, cacolic acids A–C (13–15). Structures were assigned on the basis of detailed spectroscopic analysis with comparisons to known natural products and biosynthetic considerations. In addition to revealing new chemical diversity, this study provided a valuable platform for comparing and contrasting the capabilities of the traditional dereplication technologies of HPLC-DAD, HPLC-MS and NMR, with those of the emerging HPLC-MS/MS approach known as global natural products social molecular networking (GNPS), as applied to marine sponge sesterterpene tetronic acids.

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.

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.

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