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.

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.

The structure and partial synthesis of imbricatine, a benzyltetrahydroisoquinoline alkaloid from the starfish Dermasterias imbricata

1991 ◽  
Vol 69 (1) ◽  
pp. 20-27 ◽  
Author(s):  
David L. Burgoyne ◽  
Shichang Miao ◽  
Charles Pathirana ◽  
Raymond J. Andersen ◽  
William A. Ayer ◽  
...  
Keyword(s):  
Key Words ◽  
Absolute Configuration ◽  
Spectroscopic Analysis ◽  
Chemical Degradation ◽  
Model Compounds ◽  
Partial Synthesis ◽  
The Absolute

The structure of imbricatine (1), a cytotoxic metabolite of the starfish Dermasterias imbricata, has been determined by spectroscopic analysis and chemical degradation. Synthesis of model compounds 7 and 18 provided evidence for the absolute configuration and constitution of the benzyltetrahydroisoquinoline substructure of imbricatine. Key words: imbricatine, asteroid, alkaloid.

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.

Glaciasterols A and B, 9,11-secosteroids from the marine sponge Aplysillaglacialis

1992 ◽  
Vol 70 (5) ◽  
pp. 1506-1510 ◽  
Author(s):  
Jana Pika ◽  
Mark Tischler ◽  
Raymond J. Andersen
Keyword(s):  
Marine Sponge ◽  
Spectroscopic Analysis ◽  
Northeastern Pacific

The glaciasterols, a family of cytotoxic 9,11-secosteroids, have been isolated from extracts of the northeastern Pacific sponge Aplysillaglacialis. The structures of glaciasterol A (2) and glaciasterol B (3) were elucidated by a combination of spectroscopic analysis and chemical interconversions on the native steroid 2 and the diacetate 5 of glaciasterol B (3).

Chromodorane diterpenes from the tropical dorid nudibranch Chromodoris cavae

1991 ◽  
Vol 69 (5) ◽  
pp. 768-771 ◽  
Author(s):  
Sandra A. Morris ◽  
E. Dilip de Silva ◽  
Raymond J. Andersen
Keyword(s):  
Key Words ◽  
Spectroscopic Analysis ◽  
Nmr Assignments ◽  
Carbon Skeleton

Two novel diterpenoids, chromodorolides A (1) and B (2), have been isolated from skin extracts of the tropical dorid nudibranch Chromodoris cavae. Complete NMR assignments are presented for chromodorolide A (1). The structure of chromodorolide B (2) has been solved by spectroscopic analysis. Chromodorolides A (1) and B (2) are the first examples of diterpenoids with the highly rearranged chromodorane carbon skeleton. Key words: nudibranch, diterpene, chromodorane, Chromodoris.

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.

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 Chaetolactone, A Skeletally New Cyclopentenone from Chaetomium sp. C521

2018 ◽  
Vol 13 (7) ◽  
pp. 1934578X1801300 ◽  
Author(s):  
Wen-Bo Han ◽  
He Li ◽  
Hui-Yi Zhou ◽  
Jia Meng ◽  
Jin-Ming Gao ◽  
...  
Keyword(s):  
Botrytis Cinerea ◽  
Absolute Configuration ◽  
Magnaporthe Oryzae ◽  
Spectroscopic Analysis ◽  
Alternaria Solani ◽  
Carbon Skeleton ◽  
The Absolute

Chaetolactone, a new polyketide with an unprecedented carbon skeleton, was constructed by Chaetomium sp. C521. Its structure was characterized by a combination of detailed spectroscopic analysis and ECD method, which facilitated the establishment of the absolute configuration for chaetolactone. The new compound was tested for anti-phytopathogenic activity against Botrytis cinerea, Alternaria solani, Gibberella saubinettii, and Magnaporthe oryzae, but exhibited negligible inhibition at a concentration of 20 μM.

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