scholarly journals Coumarins from Seseli hartvigii

2010 ◽  
Vol 5 (7) ◽  
pp. 1934578X1000500
Author(s):  
Lin Zhang ◽  
Alev Tosun ◽  
Masaki Baba ◽  
Yoshihito Okada ◽  
Lijun Wu ◽  
...  
Keyword(s):  
Natural Product ◽  
Spectroscopic Analysis ◽  
Chemical Conversion ◽  
Linear Type ◽  
Whole Plants ◽  
Modified Mosher’S Method

Linear-type furocoumarins, 5-[(2″ E,6″R)-6″-hydroxy-3″,7″-dimethylocta-2″,7″-dienyloxy]psoralen and 5-[(2″ E,6″ S)-6″-hydroxy-3″,7″-dimethylocta-2″,7″-dienyloxy]psoralen (1) were first isolated from whole plants of Seseli hartvigii together with one new natural product 6-(3’-methyl-2’-oxo-3’-butenyl)-7-methoxycoumarin (2), and four known compounds (tamarin, bergaptol, notoptol, and a mixture of β-sitosterol and stigmasterol). The structure of 1 was elucidated by extensive spectroscopic analysis and chemical conversion. The modified Mosher's method and HPLC were applied to determine its stereochemistry. Both R- and S-configurations exist in 1; after modification by Mosher's reagent, they were effectively separated, and their ratio was deduced to be 59% and 41%, respectively.

Trachycladindoles H–M: Molecular Networking Guided Exploration of a Library of Southern Australian Marine Sponges

2020 ◽  
Vol 73 (4) ◽  
pp. 338 ◽  
Author(s):  
Shamsunnahar Khushi ◽  
Laizuman Nahar ◽  
Angela A. Salim ◽  
Robert J. Capon
Keyword(s):  
Chemical Analysis ◽  
Natural Product ◽  
Structure Elucidation ◽  
Spectroscopic Analysis ◽  
Marine Sponges ◽  
Single Specimen ◽  
Guided Search ◽  
Guided Exploration ◽  
Rare Class ◽  
Great Australian Bight

A global natural product social (GNPS) molecular network guided search of a library of 960 southern Australian marine sponge extracts successfully detected a deep-water Great Australian Bight sponge, Geodia sp. (CMB-01063), as a new source of a rare class of indolo-imidazole alkaloids previously believed to be unique to a single specimen of Trachycladus laevispirulifer (CMB-03397). Chemical analysis of CMB-01063 detected the known trachycladindoles A–G (1–7), and led to the isolation, characterisation, and structure elucidation of the new trachycladindoles H–M (8–13). Structures for 8–13 were assigned on the basis of detailed spectroscopic analysis, with comparison to authentic standards of 1–7.

Parguerenes Revisited: New Brominated Diterpenes From the Southern Australian Marine Red Alga Laurencia Filiformis

1996 ◽  
Vol 49 (1) ◽  
pp. 19 ◽  
Author(s):  
SJ Rochfort ◽  
RJ Capon
Keyword(s):  
Natural Product ◽  
Biosynthetic Pathway ◽  
Spectroscopic Analysis ◽  
Red Alga ◽  
Biosynthetic Precursor ◽  
Chemical Correlation ◽  
New Compounds

Five new pargueranes, 15-bromoparguer-9(11)-ene-2,7,16,19-tetrol 2,7,16-triacetate (20), 15-bromoparguer-9(11)-ene-2,7,16-triol 2,7-diacetate (21), 15-bromoparguer-9(11)-ene-2,16-diol 2-acetate (22), 15-bromoparguer-9(11)-en-16-ol (23) and 15-bromoisoparguer-9(11)-en-16-ol (24), together with a plausible biosynthetic precursor, preparguerene (25), two known parguerenes , 15-bromoparguer-9(11)-ene-2,7,16,19-tetrol tetraacetate (4) and 15-bromoparguer-9(11)-ene-2,7,16-triol 2,16 diacetate (7), and the known algal metabolites (-)- aromadendrene (17), austradiol acetate (18) and austradiol diacetate (19), have been isolated from a collection of the southern Australian marine red alga Laurencia filiformis. The known synthetic parguerane 15-bromoparguer-9(11)-ene-2,7-16-triol triacetate (5) was also found for thefirst time as a natural product. In addition to securing the structures of new compounds by chemical correlation and detailed spectroscopic analysis, a lausible biosynthetic pathway has been proposed linking preparguerene, parguerene, isoparguerene and secoparguerene carbon skeletons.

Two New Glycosides from Sanicula lamelligera

2006 ◽  
Vol 61 (5) ◽  
pp. 607-610 ◽  
Author(s):  
Ling-Yun Zhou ◽  
Hai-Yang Liu ◽  
Bai-Bo Xie ◽  
Zhi-Hai Liu ◽  
Chang-Xiang Chen
Keyword(s):  
Rosmarinic Acid ◽  
Spectroscopic Analysis ◽  
Whole Plants

Two new glycosides, 21-O-β -D-glucopyranosyl-olean-12-ene-3β , 16α, 21β , 22α, 28-pentol-3-O- β -D-glucopyranosyl (1→2)-[β -D-arabinopyranosyl (1→3)]-β -D-glucopyranoside (1) and 4-O-β - D-glucopyranosyl rosmarinic acid (3), along with the known compound rosmarinic acid (2) were isolated from the whole plants of Sanicula lamelligera Hance. Their structures were elucidated by spectroscopic analysis and chemical means.

Two for One: Structure Revision of the Marine Sesterterpene Tetronic Acid Strobilinin to (8Z,13E,20Z)-Strobilinin and (8E,13Z,20Z)-Strobilinin

1994 ◽  
Vol 47 (5) ◽  
pp. 933 ◽  
Author(s):  
R Davis ◽  
RJ Capon
Keyword(s):  
Natural Product ◽  
Spectroscopic Analysis ◽  
Marine Natural Product ◽  
Geometric Isomers ◽  
Tetronic Acid ◽  
Naturally Occurring ◽  
Structure Revision ◽  
Single Compound ◽  
The Absolute ◽  
Absolute Stereochemistry

A reinvestigation of the known marine natural product strobilinin has revealed it not to be a single compound (2), but to consist of two naturally occurring geometric isomers, neither of which corresponds to the structure originally assigned. These isomers, (8E,13Z,20Z)- strobilinin (10) and (8Z,13E,20Z)-strobilinin (11), were resolved, characterized and identified as their respective acetate derivatives (6) and (7), and their structures assigned by spectroscopic analysis. It would appear that the absolute stereochemistry of the strobilinins is very likely opposite to that of co-occurring variabilin (1).

scholarly journals Synthesis and Spectroscopic Analysis of Piperine- and Piperlongumine-Inspired Natural Product Scaffolds and Their Molecular Docking with IL-1β and NF-κB Proteins

Molecules ◽  
2020 ◽  
Vol 25 (12) ◽  
pp. 2841 ◽  
Author(s):  
Gabriel Zazeri ◽  
Ana Paula R. Povinelli ◽  
Cécile S. Le Duff ◽  
Bridget Tang ◽  
Marinonio L. Cornelio ◽  
...  
Keyword(s):  
Natural Products ◽  
Binding Site ◽  
Natural Product ◽  
Structural Modification ◽  
Spectroscopic Analysis ◽  
Two Dimensional ◽  
Electronic Density ◽  
Protein Targets ◽  
Dna Binding Site ◽  
First Time

Inspired by the remarkable bioactivities exhibited by the natural products, piperine and piperlongumine, we synthesised eight natural product-inspired analogues to further investigate their structures. For the first time, we confirmed the structure of the key cyclised dihydropyrazolecarbothioamide piperine analogues including the use of two-dimensional (2D) 15N-based spectroscopy nuclear magnetic resonance (NMR) spectroscopy. Prior investigations demonstrated promising results from these scaffolds for the inhibition of inflammatory response via downregulation of the IL-1β and NF-κB pathway. However, the molecular interaction of these molecules with their protein targets remains unknown. Ab initio calculations revealed the electronic density function map of the molecules, showing the effects of structural modification in the electronic structure. Finally, molecular interactions between the synthesized molecules and the proteins IL-1β and NF-κB were achieved. Docking results showed that all the analogues interact in the DNA binding site of NF-κB with higher affinity compared to the natural products and, with the exception of 9a and 9b, have higher affinity than the natural products for the binding site of IL-1β. Specificity for the molecular recognition of 3a, 3c and 9b with IL-1β through cation–π interactions was determined. These results revealed 3a, 3c, 4a, 4c and 10 as the most promising molecules to be evaluated as IL-1β and NF-κB inhibitors.

scholarly journals Chermebilaenes A and B, New Bioactive Meroterpenoids from Co-Cultures of Marine-Derived Isolates of Penicillium bilaiae MA-267 and Penicillium chermesinum EN-480

Marine Drugs ◽  
2020 ◽  
Vol 18 (7) ◽  
pp. 339
Author(s):  
Ling-Hong Meng ◽  
Xiao-Ming Li ◽  
Hong-Lei Li ◽  
Bin-Gui Wang
Keyword(s):  
Spectroscopic Analysis ◽  
Experimental Approach ◽  
Octadecadienoic Acid ◽  
Edwardsiella Tarda ◽  
Culture Vessel ◽  
Fungal Isolates ◽  
Microbial Strains ◽  
Inhibitory Activities ◽  
Modified Mosher’S Method ◽  
Penicillium Bilaiae

The co-cultivation of two or more different microbial strains in one culture vessel was supposed to be a viable experimental approach for enhancing the diversity of the compounds produced. Two new meroterpenoid derivatives, chermebilaenes A (1) and B (2), together with three known sesquiterpenoids, sesquicaranoic acid B (3), cyclonerodiol (4) and bisabol-l-on-13-säuremethylester (5), were characterized from a co-culture of the marine-derived fungal isolates of Penicillium bilaiae MA-267 and Penicillium chermesinum EN-480. Neither fungus produced these compounds when cultured alone under the same conditions. Compound 1 represents an unprecedented acorane-type sesquiterpene hybridized with an octadecadienoic acid skeleton. The structures were elucidated on the basis of spectroscopic analysis, and the absolute configurations were assumed on the basis of acidic hydrolysis combined with modified Mosher’s method and electronic circular dichroism (ECD) calculations. Compound 1 showed potent inhibitory activities against Ceratobasidium cornigerum and Edwardsiella tarda.

scholarly journals Muyocopronones A and B: azaphilones from the endophytic fungus Muyocopron laterale

2020 ◽  
Vol 16 ◽  
pp. 2100-2107
Author(s):  
Ken-ichi Nakashima ◽  
Junko Tomida ◽  
Tomoe Tsuboi ◽  
Yoshiaki Kawamura ◽  
Makoto Inoue
Keyword(s):  
Antibacterial Activity ◽  
Endophytic Fungus ◽  
Spectroscopic Analysis ◽  
Gram Positive ◽  
Electronic Circular Dichroism ◽  
Gram Positive Bacteria ◽  
Circular Dichroism Data ◽  
Circular Dichroïsm ◽  
Weak Antibacterial Activity ◽  
Modified Mosher’S Method

Two new azaphilones, namely muyocopronones A (1) and B (2), were isolated from the cultures of an endophytic fungus Muyocopron laterale ECN279. Their structures were elucidated by extensive spectroscopic analysis. Their absolute configurations were determined using the modified Mosher’s method and through comparisons of experimental and calculated electronic circular dichroism data. In addition, muyocopronone B (2) was found to exhibit a weak antibacterial activity against some Gram-positive bacteria.

Trunculin-F and Contrunculin-A and -B: Novel Oxygenated Norterpenes From a Southern Australian Marine Sponge, Latrunculia conulosa

1993 ◽  
Vol 46 (9) ◽  
pp. 1363 ◽  
Author(s):  
MS Butler ◽  
RJ Capon
Keyword(s):  
Methyl Ester ◽  
Natural Product ◽  
Marine Sponge ◽  
Coastal Waters ◽  
Spectroscopic Analysis ◽  
Marine Natural Product ◽  
New Compounds ◽  
Absolute Stereochemistry

A specimen of Latrunculia conulosa from southern Australian coastal waters, previously observed to contain conulosin-A (6) and conulosin-B (7), has also been found to yield the known marine natural product trunculin-C methyl ester (14), along with three new norterpenes, trunculin-F (10), contrunculin-A (11) and contrunculin-B (12). Trunculin-F (10) was isolated, characterized and identified as its methyl ester (13), and its absolute stereochemistry determined by Horeau analysis. The structures for all new compounds were secured by detailed spectroscopic analysis.

A New Sesterterpene Tetronic Acid From an Australian Marine Sponge, Psammocinia sp.

1995 ◽  
Vol 48 (11) ◽  
pp. 1899 ◽  
Author(s):  
L Murray ◽  
H Hamit ◽  
JNA Hooper ◽  
L Hobbs ◽  
RJ Capon
Keyword(s):  
Antimicrobial Activity ◽  
Natural Product ◽  
Marine Sponge ◽  
Spectroscopic Analysis ◽  
Marine Natural Product ◽  
Structural Isomer ◽  
Tetronic Acid ◽  
Spectroscopic Characteristics

A new sesterterpene tetronic acid (5) exhibiting antimicrobial activity has been isolated from an Australian marine sponge, Psammocinia sp., and its structure secured by detailed spectroscopic analysis. The tetronic acid (5) possesses almost identical spectroscopic characteristics to, and is a structural isomer of, the known marine natural product (6) previously reported from an Australian sponge.

scholarly journals Sacraoxides A–G, Bioactive Cembranoids from Gum Resin of Boswellia sacra

2021 ◽  
Vol 9 ◽  
Author(s):  
Bingyang Zhang ◽  
Di Liu ◽  
Wenyue Ji ◽  
Kouharu Otsuki ◽  
Koji Higai ◽  
...  
Keyword(s):  
Nitric Oxide ◽  
Spectroscopic Analysis ◽  
Raw264.7 Cells ◽  
No Production ◽  
X Ray Diffraction ◽  
X Ray ◽  
Inhibitory Activities ◽  
Modified Mosher’S Method ◽  
Boswellia Sacra

Seven undescribed cembranoids, sacraoxides A–G (1, 3–8) were isolated from the gum resin of Boswellia sacra. Their structures were elucidated by extensive physicochemical and spectroscopic analysis, as well as ECD calculation, modified Mosher’s method and X-ray diffraction crystallography. Compounds 6 and 7 exhibited inhibitory activities on nitric oxide (NO) production induced by lipopolysaccharide in RAW264.7 cells with IC50 values of 24.9 ± 1.7 and 36.4 ± 2.9 μM.

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