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.

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).

Deoxyspongiaquinones: New Sesquiterpene Quinones and Hydroquinones From a Southern Australian Marine Sponge Euryspongia sp.

1996 ◽  
Vol 49 (5) ◽  
pp. 611 ◽  
Author(s):  
S Urban ◽  
RJ Capon
Keyword(s):  
Marine Sponge ◽  
Spectroscopic Analysis ◽  
Chemical Investigation ◽  
Great Australian Bight

Chemical investigation of a marine sponge, Euryspongia sp., collected from the Great Australian Bight, Australia, resulted in the isolation of two new sesquiterpene quinones , deoxyspongiaquinone (4) and (E)-chlorodeoxyspongiaquinone (5), as well as two sesquiterpene hydroquinones, deoxyspongiaquinol (6) and (E)-chlorodeoxyspongiaquinol (7). The structures for (4)-(7) were determined by detailed spectroscopic analysis, as well as chemical interconversion and degradation.

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.

Isoquinoline Alkaloids from Corydalis taliensis

2007 ◽  
Vol 62 (9) ◽  
pp. 1199-1202 ◽  
Author(s):  
Ying-Rui Wu ◽  
You-Xing Zhao ◽  
Yu-Qing Liu ◽  
Jun Zhou
Keyword(s):  
Spectral Data ◽  
Spectroscopic Analysis ◽  
Chemical Investigation ◽  
Perennial Herb ◽  
Isoquinoline Alkaloids ◽  
Rheumatic Arthritis ◽  
Spectral Evidence

Corydalis taliensis Franch is a perennial herb used for treatment of rheumatic arthritis, toothache, and hepatitis. The chemical investigation of this plant resulted in the isolation of a new compound, named taliensineside (1). Its structure was identified on the basis of spectral evidence. In addition, thirteen known isoquinoline alkaloids (2 - 14) were isolated and identified by spectroscopic analysis and comparison of their spectral data with those reported previously.

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 Saturated Ceramides from the Sponge Dysidea Robusta

2009 ◽  
Vol 4 (7) ◽  
pp. 1934578X0900400
Author(s):  
Suzi O. Marques ◽  
Katyuscya Veloso ◽  
Antonio G. Ferreira ◽  
Eduardo Hajdu ◽  
Solange Peixinho ◽  
...  
Keyword(s):  
Marine Sponge ◽  
Crude Extract ◽  
Spectroscopic Data ◽  
Chemical Investigation ◽  
Ms Analysis

Chemical investigation of the crude extract of a marine sponge Dysidea robusta led to the isolation of an inseparable mixture of saturated ceramides. These were identified from spectroscopic data as well as by hydrolysis followed by LC-MS analysis of the sphingosine moieties.

scholarly journals Three New Spongian Diterpenes from the Fijian Marine Sponge Spongia sp

2009 ◽  
Vol 4 (3) ◽  
pp. 1934578X0900400 ◽  
Author(s):  
Harald Gross ◽  
Anthony D. Wright ◽  
Uwe Reinscheid ◽  
Gabriele M. König
Keyword(s):  
Molecular Modeling ◽  
Marine Sponge ◽  
Spectroscopic Data ◽  
Chemical Investigation ◽  
Complete Analysis ◽  
Quantum Mechanical ◽  
Quantum Mechanical Calculations ◽  
Fiji Islands ◽  
Combined Strategy ◽  
Spongian Diterpene

Chemical investigation of the marine sponge Spongia sp., collected from the Fiji Islands resulted in the isolation of three new furanoditerpenoids 1-3, along with the known compounds epispongiatriol (4) and 17,19-dihydroxyspongia-13(16),14-dien-2,3-dione (5) While 1 is a new spongian diterpene with a modified oxidation pattern, compounds 2 and 3 represent two new ring A-contracted spongians, displaying a novel and unprecedented nor-spongian carbon skeleton. Despite their labile nature the structures could be established through a combined strategy including complete analysis of spectroscopic data (NMR, MS), molecular modeling and quantum-mechanical calculations.

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.

Glucosides from the Fresh Flowers of Juglans regia L. and Their Biological Evaluation

2019 ◽  
Vol 17 (1) ◽  
pp. 31-35
Author(s):  
Haibo Wang ◽  
Xikui Liu
Keyword(s):  
Spectroscopic Analysis ◽  
Juglans Regia ◽  
2D Nmr ◽  
Antibacterial Activities ◽  
Biological Evaluation ◽  
Chemical Investigation ◽  
Etoac Extract

The chemical investigation of the EtOAc extract of the fresh flowers of Juglans regia L. resulted in a new α-tetralonyl glucoside (1) and two known glucosides (2-3). The structure of the new compound was determined by extensive 1D and 2D NMR spectroscopic analysis and HRESIMS. The biological evaluation of the obtained glucosides showed that compound 1 and 3 displayed good antioxidant and antibacterial activities. These two compounds were identified as the main functional molecules in the fresh flowers of Juglans regia L.

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