scholarly journals Integrating Molecular Networking and 1H NMR Spectroscopy for Isolation of Bioactive Metabolites from the Persian Gulf Sponge Axinella sinoxea

Marine Drugs ◽  
2020 ◽  
Vol 18 (7) ◽  
pp. 366
Author(s):  
Reza Mohsenian Kouchaksaraee ◽  
Mahdi Moridi Farimani ◽  
Fengjie Li ◽  
Melika Nazemi ◽  
Deniz Tasdemir

The geographic position, highly fluctuating sea temperatures and hypersalinity make Persian Gulf an extreme environment. Although this unique environment has high biodiversity dominated by invertebrates, its potential in marine biodiscovery has largely remained untapped. Herein, we aimed at a detailed analysis of the metabolome and bioactivity profiles of the marine sponge Axinella sinoxea collected from the northeast coast of the Persian Gulf in Iran. The crude extract and its Kupchan subextracts were tested in multiple in-house bioassays, and the crude extract and its CHCl3-soluble portion showed in vitro antibacterial activity against Methicillin-resistant Staphylococcus aureus (MRSA) and Enterococcus faecium (Efm). A molecular networking (MN)-based dereplication strategy by UPLC-MS/MS revealed the presence of phospholipids and steroids, while 1H NMR spectroscopy indicated the presence of additional metabolites, such as diketopiperazines (DKPs). Integrated MN and 1H NMR analyses on both the crude and CHCl3 extracts combined with an antibacterial activity-guided isolation approach afforded eight metabolites: a new diketopiperazine, (-)-cyclo(L-trans-Hyp-L-Ile) (8); a known diketopiperazine, cyclo(L-trans-Hyp-L-Phe) (7); two known phospholipids, 1-O-hexadecyl-sn-glycero-3-phosphocholine (1) and 1-O-octadecanoyl-sn-glycero-3-phosphocholine (2); two known steroids, 3β-hydroxycholest-5-ene-7,24-dione (3) and (22E)-3β-hydroxycholesta-5,22-diene-7,24-dione (4); two known monoterpenes, loliolide (5) and 5-epi-loliolide (6). The chemical structures of the isolates were elucidated by a combination of NMR spectroscopy, HRMS and [α]D analyses. All compounds were tested against MRSA and Efm, and compound 3 showed moderate antibacterial activity against MRSA (IC50 value 70 μg/mL). This is the first study that has dealt with chemical and bioactivity profiling of A. sinoxea leading to isolation and characterization of pure sponge metabolites.

Fitoterapia ◽  
2016 ◽  
Vol 114 ◽  
pp. 138-143 ◽  
Author(s):  
Chuan-Yang Zhang ◽  
Jian-Guang Luo ◽  
Rui-Huan Liu ◽  
Ru Lin ◽  
Ming-Hua Yang ◽  
...  

2008 ◽  
Vol 59 (7) ◽  
Author(s):  
Maria Maganu ◽  
Filip Chiraleu ◽  
Constantin Draghici ◽  
Gheorghe Mihai

The previous data obtained by 1H-NMR spectroscopy established the existence of an asymmetry of the bond between Pd and p-allylic groups, even in the p-allyl-Pd complexes dimers which are considered usually symmetric dimers. The asymmetry of the bond depends by the substitutes of the allylic group. Other analytical methods were investigated for additional proof of the obtained results. Thus, this paper discusses how this asymmetry would be reflected in the infrared spectra and in the reaction of the complexes with carbon monoxide.


2020 ◽  
Vol 07 ◽  
Author(s):  
Christian Trapp ◽  
Corinna Schuster ◽  
Chris Drewniok ◽  
Dieter Greif ◽  
Martin Hofrichter

Background:: Chiral β-hydroxy esters and α-substituted β-hydroxy esters represent versatile building blocks for pheromones, β-lactam antibiotics and 1,2- or 1,3-aminoalcohols. Objective:: Synthesis of versatile α-substituted β-keto esters and their diastereoselective reduction to the corresponding syn- or anti-α-substituted β-hydroxy esters. Assignment of the relative configuration by NMR-spectroscopy after a CURTIUS rearrangement of α-substituted β-keto esters to 4-substituted 5-methyloxazolidin-2-ones. Method:: Diastereoselective reduction was achieved by using different LEWIS acids (zinc, titanium and cerium) in combination with complex borohydrides as reducing agents. Assignment of the relative configuration was verified by 1H-NMR spectroscopy after CURTIUS-rearrangement of α-substituted β-hydroxy esters to 4-substituted 5-methyloxazolidin-2-ones. Results:: For the syn-selective reduction, titanium tetrachloride (TiCl4) in combination with a pyridine-borane complex (py BH3) led to diastereoselectivities up to 99% dr. High anti-selective reduction was achieved by using cerium trichloride (CeCl3) and steric hindered reducing agents such as lithium triethylborohydride (LiEt3BH). After CURTIUS-rearrangement of each α-substituted β-hydroxy ester to the corresponding 4-substituted 5-methyloxazolidin-2-one, the relative configuration was confirmed by 1H NMR-spectroscopy. Conclusion:: We have expanded the procedure of LEWIS acid-mediated diastereoselective reduction to bulky α-substituents such as the isopropyl group and the electron withdrawing phenyl ring.


1985 ◽  
Vol 50 (8) ◽  
pp. 1899-1905 ◽  
Author(s):  
Milena Masojídková ◽  
Jaroslav Zajíček ◽  
Miloš Buděšínský ◽  
Ivan Rosenberg ◽  
Antonín Holý

Conformational properties of ribonucleoside 5'-O-phosphonylmethyl derivatives have been determined by 1H NMR spectroscopy and compared with those of natural nucleosides and 5'-nucleotides.


Author(s):  
Masanori Inagaki ◽  
Risa Iwakuma ◽  
Susumu Kawakami ◽  
Hideaki Otsuka ◽  
Harinantenaina L. Rakotondraibe

Author(s):  
Praveen Kumar Solasa ◽  
Manu Saraswathi Kesava Pillai ◽  
Vijendra Kumar ◽  
Ancy Smitha Alex ◽  
Srinivas Chinthalapalli ◽  
...  

Sign in / Sign up

Export Citation Format

Share Document