Haliclocyclin C, a New Monomeric 3-Alkyl Pyridinium Alkaloid from the Arctic Marine Sponge Haliclona viscosa

2011 ◽  
Vol 66 (7) ◽  
pp. 745-748 ◽  
Author(s):  
Gesine Schmidt ◽  
Christoph Timm ◽  
Matthias Köck
Keyword(s):  
Natural Product ◽  
Marine Sponge ◽  
Crude Extract ◽  
Structure Elucidation ◽  
Alkyl Chain ◽  
Natural Source ◽  
The Arctic ◽  
Synthetic Compound ◽  
Methylene Groups ◽  
First Time

For the first time, the macrocyclic monomeric 3-alkyl pyridinium alkaloid with an alkyl chain of 13 methylene groups, haliclocyclin C (1), could be identified from a natural source in the crude extract of the Arctic sponge Haliclona viscosa. Structure elucidation was carried out by comparison of the natural product with the corresponding synthetic compound.

Structure Elucidation of Submilligram Quantities of Natural Products - Application to Haliclamines G and H from the Arctic Marine Sponge Haliclona viscosa

2012 ◽  
Vol 67 (9) ◽  
pp. 944-950 ◽  
Author(s):  
Christine Cychon ◽  
Gesine Schmidt ◽  
Thorsten Mordhorst ◽  
Matthias Köck
Keyword(s):  
Marine Sponge ◽  
Crude Extract ◽  
Structure Elucidation ◽  
Mass Spectrometric ◽  
The Arctic ◽  
Detailed Knowledge ◽  
Fragmentation Pattern ◽  
Synthetic Compounds ◽  
Alkyl Chains ◽  
Methylene Groups

Two new haliclamines were identified directly from the crude extract of the Arctic sponge Haliclona viscosa using improved chromatographic conditions and a detailed knowledge about the fragmentation pattern of haliclamines. These are haliclamine G (1) with two alkyl chains of equal length (10 methylene groups) and haliclamine H (2) with alkyl chains of 10 and 12 methylene groups. Due to the limited amount of sponge material available, the haliclamines were not isolated, and the structure elucidation relied on the chromatographic and mass spectrometric comparison with synthetic compounds

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.

Lepistirones, Major Volatile Metabolites from Liquid Cultures of Lepista irina (Basidiomycotina)

1991 ◽  
Vol 46 (3-4) ◽  
pp. 169-171 ◽  
Author(s):  
Wolf-Rainer Abraham ◽  
Hans-Peter Hanssen ◽  
Irene Urbasch
Keyword(s):  
Liquid Medium ◽  
Natural Product ◽  
Structure Elucidation ◽  
Spectroscopic Methods ◽  
Liquid Cultures ◽  
Volatile Metabolites ◽  
Nuclear Overhauser Enhancement ◽  
Steam Distillate ◽  
Nuclear Overhauser ◽  
First Time

The basidiomycete Lepista irina (F r.) Bigelow (strains CBS 366.47 and CBS 458.79) was cultivated on a biomalt (2% )-liquid medium for 28 days. The steam distillate was analyzed by GLC and GLC-S. The structure elucidation of the predominant constituent resulted from spectroscopic methods, particularly from its 13CNMR spectrum, nuclear Overhauser enhancement 1HNMR data, and from 2d 1H homonuclear shift correlation. The bisabolane derivative was nam ed lepistirone and is described for the first time as a natural product. Two minor related com pounds could be characterized by their MS data.

Isolation, Structure Elucidation and Activity of Anthracycline Acetates from a Terrestrial Streptomyces sp.

2003 ◽  
Vol 58 (12) ◽  
pp. 1242-1246 ◽  
Author(s):  
Serge Fotso ◽  
Rajendra P. Maskey ◽  
Iris Grün-Wollny ◽  
Hartmut Laatsch
Keyword(s):  
Molecular Weight ◽  
Natural Product ◽  
Structure Elucidation ◽  
Ethyl Acetate Extract ◽  
2D Nmr ◽  
Streptomyces Sp ◽  
Naturally Occurring ◽  
Nmr Data ◽  
New Antibiotics ◽  
First Time

The red coloured ethyl acetate extract of the Streptomyces sp. isolate GW37/3236 delivered the two new antibiotics 13-O-acetyl-bisanhydro-13-dihydrodaunomycinone (3c) and 4,13-O-diacetylbisanhydro- 4-O-demethyl-13-dihydrodaunomycinone (3d) and additionally several known compounds. The quinones 3c and 3d are the first naturally occurring quinone acetates. Their structures were derived by comparison of the NMR data with those of bisanhydro-13-dihydrodaunomycinone (3b) and by interpretation of the 2D NMR data accompanied by the molecular weight and formula. 2-Acetamido-3-hydroxybenzamide (5) was also isolated from the extract and was identified by comparison of the NMR data with those of 2-acetamidobenzamide and by 2D NMR correlations. 6,9,11- Trihydroxy-4-methoxy-5,12-naphthacenedione (4) is isolated for the first time as a natural product.

scholarly journals Indole Alkaloids from Tropical Sponge Hyrtios sp. as Isocitrate Lyase Inhibitors

2018 ◽  
Vol 13 (6) ◽  
pp. 1934578X1801300 ◽  
Author(s):  
Seung-Il Park ◽  
Yeon-Ju Lee ◽  
Hoshik Won ◽  
Ki-Bong Oh ◽  
Hyi-Seung Lee
Keyword(s):  
Candida Albicans ◽  
Marine Sponge ◽  
Isocitrate Lyase ◽  
Indole Alkaloids ◽  
Natural Source ◽  
Spectroscopic Analyses ◽  
Inhibitory Activities ◽  
First Time

A new β-carboline alkaloid, 3,4-dihydrohyrtiosulawesine (8), and fifteen known alkaloids were isolated from the tropical marine sponge Hyrtios sp. Among these known compounds, β-ketoserotonin (10) has been isolated for the first time from a natural source. The structures of the isolated compounds were determined by spectroscopic analyses and comparison with literature values. Compound 8 displayed potent inhibitory activities against isocitrate lyase (IC50: 92.9 μM) from Candida albicans.

Étude des Hernandiacées. XII. Dimères aporphine–benzylisoquinoléine originaux isolés de Hernandiapeltata

1986 ◽  
Vol 64 (1) ◽  
pp. 123-126 ◽  
Author(s):  
M. C. Chalandre ◽  
J. Bruneton ◽  
P. Cabalion ◽  
H. Guinaudeau
Keyword(s):  
Natural Source ◽  
Synthetic Compound ◽  
First Time

The bark of Hernandiapeltata Meissner (Hernandiaceae) has yielded four new dimeric alkaloids, namely (+)-6-northalicarpine 6, (+)-thalicarpine 2′-N-oxide 10, (+)-hebridamine 11, and (+)-vilaportine 12. Hebridamine is the first example of a benzylisoquinoline-phenanthrene dimer and (+)-vilaportine is a dimer with an oxoaporphinium zwitterionic moiety. The 6a,7-dehydrothalmelatine 9, previously known as a synthetic compound, has been isolated from a natural source for the first time. The possibility of a biogenetic relationship between (+)-vanuatine and (+)-thalicarpine 7 is considered.

MS-guided Fractionation as a Fast Way to the Identification of New Natural Products – MALDI-TOF-MS Screening of the Marine Sponge Stylissa caribica

2007 ◽  
Vol 62 (4) ◽  
pp. 600-604 ◽  
Author(s):  
Achim Grube ◽  
Thomas Maier ◽  
Matthias Köck
Keyword(s):  
Marine Sponge ◽  
Crude Extract ◽  
Screening Method ◽  
Rapid Identification ◽  
Sponge Tissue ◽  
Maldi Tof Ms ◽  
Maldi Tof ◽  
First Time ◽  
Tof Ms ◽  
Good Agreement

MALDI-TOF-MS was used for the first time as a direct screening method to analyse sponge tissue (Stylissa caribica). In order to validate this method the results were compared with a HPLC-ESI-MS analysis of the crude extract from the investigated sponge. Both methods showed a good agreement in their results, allowing for the rapid identification of 15 pyrrole-imidazole alkaloids.

Structure elucidation of a proton-deficient natural product using LR-HSQMBC supported by DFT calculations

Planta Medica ◽  
2015 ◽  
Vol 81 (11) ◽  
Author(s):  
J Saurí ◽  
STS Chan ◽  
AV Buevich ◽  
KR Gustafson ◽  
RT Williamson ◽  
...  
Keyword(s):  
Dft Calculations ◽  
Natural Product ◽  
Structure Elucidation

A Well-Ordered Thing

2018 ◽  
Author(s):  
Michael D. Gordin
Keyword(s):  
Nineteenth Century ◽  
History Of Science ◽  
Periodic Table ◽  
The Arctic ◽  
Classic Work ◽  
Hot Air ◽  
History Of ◽  
First Time

Dmitrii Mendeleev (1834–1907) is a name we recognize, but perhaps only as the creator of the periodic table of elements. Generally, little else has been known about him. This book is an authoritative biography of Mendeleev that draws a multifaceted portrait of his life for the first time. As the book reveals, Mendeleev was not only a luminary in the history of science, he was also an astonishingly wide-ranging political and cultural figure. From his attack on Spiritualism to his failed voyage to the Arctic and his near-mythical hot-air balloon trip, this is the story of an extraordinary maverick. The ideals that shaped his work outside science also led Mendeleev to order the elements and, eventually, to engineer one of the most fascinating scientific developments of the nineteenth century. This book is a classic work that tells the story of one of the world's most important minds.

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