New Chlorinated Metabolites from the Tropical Marine Sponge Dysidea herbacea

1997 ◽  
Vol 50 (2) ◽  
pp. 139 ◽  
Author(s):  
Eric J. Dumdei ◽  
Jamie S. Simpson ◽  
Mary J. Garson ◽  
Karl A. Byriel ◽  
Colin H. L. Kennard
Keyword(s):  
Great Barrier Reef ◽  
Marine Sponge ◽  
Crystallographic Analysis ◽  
Southern Region ◽  
Barrier Reef ◽  
X Ray ◽  
Dysidea Herbacea ◽  
Absolute Stereochemistry

Three new chlorinated metabolites, namely 3-(3,3-dichloro-2-methylpropyl)-6-(3,3-dichloro-2-methyl-propylidene)-1,4-dimethylpiperazine-2,5-dione (3), 1-methyl-3-(3,3,3-trichloro-2-methylpropyl)-6-(3,3,3-richloro-2-methylpropylidene)piperazine-2,5-dione (4) and 5,5-dichloro-4-methyl-2-[methyl(4,4-dichloro-3-methyl-1-oxobutyl)amino]-N-(thiazol-2-ylmethyl)pentanamide (8), have been isolated from collections of Dysidea herbacea from the southern region of the Great Barrier Reef. The relative and absolute stereochemistry of (4) was determined by X-ray crystallographic analysis.

A New Brominated Diphenyl Ether from the Marine Sponge Dysidea herbacea.

2000 ◽  
Vol 53 (4) ◽  
pp. 299 ◽  
Author(s):  
Bruce F. Bowden ◽  
Leanne Towerzey ◽  
Peter C. Junk
Keyword(s):  
Great Barrier Reef ◽  
Marine Sponge ◽  
Polybrominated Diphenyl Ethers ◽  
Diphenyl Ether ◽  
Two Dimensional ◽  
Barrier Reef ◽  
X Ray Diffraction ◽  
X Ray ◽  
Diphenyl Ethers ◽  
Dysidea Herbacea

Samples of Dysidea herbacea collected at Pelorus Island, Great Barrier Reef, Australia, afforded a new polybrominated diphenyl ether (1). The structure was determined by n.m.r. two-dimensional methods and by an X-ray diffraction study. N.m.r. spectral assignments for (1) and some previously reported isomeric polybrominated diphenyl ethers are discussed.

THE REACTION OF UNSATURATED CARBOHYDRATES WITH CARBON MONOXIDE AND HYDROGEN: V. ABSOLUTE STEREOCHEMISTRY OF ANHYDRODEOXYHEPTITOLS FROM 3,4,6-TRI-O-ACETYL-D-GLUCAL. STEREOCHEMISTRY OF HYDROFORMYLATION. CONFORMATIONAL ANALYSIS

1965 ◽  
Vol 43 (5) ◽  
pp. 1375-1381 ◽  
Author(s):  
Alex Rosenthal ◽  
Hans J. Koch
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Carbon Monoxide ◽  
Absolute Configuration ◽  
Sodium Iodide ◽  
Crystallographic Analysis ◽  
X Ray ◽  
Dicobalt Octacarbonyl ◽  
The Absolute ◽  
Compound Ii ◽  
Absolute Stereochemistry

3,4,6-Tri-O-acetyl-D-glucal reacted with carbon monoxide and hydrogen in the presence of dicobalt octacarbonyl to yield a mixture of two epimeric anhydrodeoxyheptitols, namely, 4,5,7-tri-O-acetyl-2,6-anhydro-3-deoxy-D-manno-heptitol (I) and 4,5,7-tri-O-acetyl-2,6-anhydro-3-deoxy-D-gluco-heptitol (II). De-O-acetylation of the mixture, followed by chromatographic separation, yielded crystalline 2,6-anhydro-3-deoxy-D-manno-heptitol (III) and 2,6-anhydro-3-deoxy-D-gluco-heptitol (IV). Reaction of the mixture of heptitols (I) and (II) with p-bromobenzenesulfonyl chloride, followed by fractional crystallization of the brosylates, gave pure 4,5,7-tri-O-acetyl-2,6-anhydro-1-O-(p-bromophenylsulfonyl)-3-deoxy-D-gluco-heptitol (VII). The absolute configuration of (VII) has been previously established by X-ray crystallographic analysis. The absolute configuration of (III) was established by correlation with that of (VII). The conversion of compound (II) into various derivatives is described.Reaction of 3,4,6-tri-O-acetyl-D-glucal with carbon monoxide and deuterium afforded 2,6-anhydro-3-deoxy-D-manno-heptitol-1,1,3-2H3 (XIII) and 2,6-anhydro-3-deoxy-D-gluco-heptitol-1,1,3-2H3 (XIV). Examination of the nuclear magnetic resonance (n.m.r.) spectra of the normal and deuterated anhydrodeoxyheptitols confirmed the structural assignments and showed that cis addition to the double bond took place to give (XIV).Comparison of the exchange reaction of sodium iodide with 4,5,7-tri-O-acetyl-2,6-anhydro-3-deoxy-1-O-tosyl-D-gluco-heptitol (VIII) and with 4,5,7-tri-O-acetyl-2,6-anhydro-3-deoxy-1-O-tosyl-D-manno-heptitol (XV) revealed that the equatorial primary tosyloxy group of (VIII) was exchanged by iodine twice as readily as the axial primary tosyloxy group of (XV).

Studies of Australian Ascidians. VI. Virenamides D and E, Linear Peptides from the Colonial Didemnid Ascidian Diplosoma virens

1997 ◽  
Vol 50 (4) ◽  
pp. 337 ◽  
Author(s):  
Yunjiang Feng ◽  
Bruce F. Bowden
Keyword(s):  
Great Barrier Reef ◽  
Spectroscopic Data ◽  
Two Dimensional ◽  
Barrier Reef ◽  
Minor Constituents ◽  
One Dimensional ◽  
The Absolute ◽  
Absolute Stereochemistry

Two new linear cytotoxic tripeptides, virenamides D and E, have been isolated as minor constituents of extracts of the didemnid ascidianDiplosoma virens collected on the Great Barrier Reef, Australia. Their structures were deduced from one-dimensional and two-dimensional n.m.r. spectroscopic data, and the absolute stereochemistry of virenamide E is proven by synthesis from virenamide A.

The Great Barrier Reef Expedition 1928–29: The crystal structure and occurrence of weddellite, ideally CaC2O4·2.5H2O, from the Low Isles, Queensland

2016 ◽  
Vol 80 (2) ◽  
pp. 399-406 ◽  
Author(s):  
Stuart J. Mills ◽  
Andrew G. Christy
Keyword(s):  
Crystal Structure ◽  
Coral Reef ◽  
Low Temperature ◽  
Great Barrier Reef ◽  
Single Crystal ◽  
Structure Study ◽  
Barrier Reef ◽  
X Ray Diffraction ◽  
X Ray ◽  
First Report

Abstract“Envelope crystals” collected during The Great Barrier Reef Expedition in May 1929 have been studied using low-temperature synchrotron single-crystal X-ray diffraction. The crystals are shown to be weddellite, with the largest content of zeolitic water reported to date. A new H2O site has been located within the crystal structure. Study of the crystals show that the end-member formula for weddellite should be reported as CaC2O4·(2.5 – x)H2O, where 0≤x≤ 0.25, instead of CaC2O4·(2H2O or CaC2O4·(2 + x )H2O. This is also the first report of weddellite occurring in a coral reef.

Coscinoquinol, a New Cytotoxic Sesterterpene From a Dictyoceratid Sponge, Coscinoderma sp.

1994 ◽  
Vol 47 (1) ◽  
pp. 191 ◽  
Author(s):  
GV Alea ◽  
AR Carroll ◽  
BF Bowden
Keyword(s):  
Great Barrier Reef ◽  
Marine Sponge ◽  
Biological Activities ◽  
Two Dimensional ◽  
Barrier Reef ◽  
One Dimensional

A marine sponge, Coscinoderma sp., from the Great Barrier Reef, Australia, contained a new sesterterpene hydroquinone, coscinoquinol (1). The structure was elucidated by one-dimensional and two-dimensional n.m.r. techniques. Cytotoxicity and other biological activities are reported for (1).

Revised Absolute Configurations of Latifolic Acid and the Pyrrolizidine Alkaloid Latifoline

1988 ◽  
Vol 41 (11) ◽  
pp. 1781 ◽  
Author(s):  
JN Roitman ◽  
RY Wong
Keyword(s):  
Carboxylic Acid ◽  
Single Crystal ◽  
Pyrrolizidine Alkaloid ◽  
Crystallographic Analysis ◽  
Side Chain ◽  
X Ray ◽  
The Absolute ◽  
Absolute Stereochemistry

The absolute stereochemistry of (+)- latifolk acid has been determined by single-crystal X-ray crystallographic analysis to be (2S,3R,4R)-3- hydroxy-2,4-dimethyl-5-oxotetrahydrofuran-3-carboxylic acid. The configuration of the three chiral centres is opposite to that presently recorded in the literature. Accordingly, the configuration of the pyrrolizidine alkaloid, latifoline, which includes a latifolic acid side chain, must be revised.

Two New Isonakafurans from the Great Barrier Reef Sponge Dysidea sp. nov.

1998 ◽  
Vol 51 (3) ◽  
pp. 195 ◽  
Author(s):  
Andrew E. Flowers ◽  
Mary J. Garson ◽  
Karl A. Byriel ◽  
Colin H. L. Kennard
Keyword(s):  
Great Barrier Reef ◽  
Trichophyton Mentagrophytes ◽  
Marine Fungus ◽  
Crystallographic Analysis ◽  
Barrier Reef ◽  
Tree Island ◽  
Growth Inhibitory ◽  
Growth Inhibitory Activity ◽  
Relative Stereochemistry ◽  
P388 Cell

Two new sesquiterpenes, the furan Δ7,14-isonakafuran-9 (11) and the autoxidized derivative (12), were isolated from the sponge Dysidea sp. nov. collected from One Tree Island on the Great Barrier Reef. The structures of the two new sesquiterpenes, which both contain a bicyclo[4.3.1]decane skeleton, were deduced by use of one- and two-dimensional n.m.r. spectroscopy, in particular by n.O.e. and HMBC experiments. Compound (11) is isomeric with nakafuran-9 (6) while the hydroperoxide derivative (12) was subjected to X-ray crystallographic analysis to confirm its relative stereochemistry at C1 and C11. Both metabolites have growth inhibitory activity against the P388 cell line, while the hydroperoxide derivative (12) is also inhibitory to the marine fungus Trichophyton mentagrophytes.

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).

Pigments of Fungi. LVII. Structure and X-Ray Crystallographic Analysis of Dermocanarin 10, a New Naphthalene - Dihydroanthracenone Dimer from an Australian Dermocybe Toadstool

1999 ◽  
Vol 52 (9) ◽  
pp. 881 ◽  
Author(s):  
Melvyn Gill ◽  
Petra M. Millar ◽  
Evelin Raudies ◽  
Somphone Phonh-Axa ◽  
Jonathan M. White ◽  
...  
Keyword(s):  
Single Crystal ◽  
Structure Analysis ◽  
Spectroscopic Data ◽  
Crystallographic Analysis ◽  
Fungal Metabolite ◽  
X Ray ◽  
Absolute Stereochemistry

The structure and absolute stereochemistry of the fungal metabolite dermocanarin 10 (2), which differs from all previous members of the dermocanarin group by virtue of the connectivity between the anthraquinone and dimethoxynaphthol rings, is deduced from spectroscopic data and confirmed by a single-crystal X-ray structure analysis.

scholarly journals New Cytotoxic Steroid Produced by the Soil-Derived Fungus Aspergillus flavus JDW-1

2019 ◽  
Vol 14 (5) ◽  
pp. 1934578X1985037 ◽  
Author(s):  
Wenqiang Guo ◽  
Wenjie Liu ◽  
Feng Xiao ◽  
Miaomiao Zhang ◽  
Longqiang Li ◽  
...  
Keyword(s):  
Aspergillus Flavus ◽  
Spectroscopic Data ◽  
Inhibitory Concentration ◽  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
Crystallographic Analysis ◽  
Scavenging Activity ◽  
X Ray ◽  
Hct 116 ◽  
Absolute Stereochemistry

One new steroid 1, together with seven known compounds 2 to 8, were discovered in the extract of a soil-derived fungus Aspergillus flavus JDW-1. The structure, including the absolute stereochemistry of new compound 1, was established by interpretation of extensive nuclear magnetic resonance spectroscopic data and further confirmed by X-ray crystallographic analysis. The cytotoxicity of 1 against the A-549, Hela, HCT-116, MGC-803, and HO-8910 cell lines was evaluated, which showed cytotoxicity with the half-maximal inhibitory concentration (IC50) values as 5.00 to 22.38 μM. Compounds 2 to 8 exhibited moderate radical scavenging activity against DPPH with IC50 values ranging from 4.7 to 28.5 μM.

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