scholarly journals Three New Quinazoline-Containing Indole Alkaloids From the Marine-Derived Fungus Aspergillus sp. HNMF114

2021 ◽  
Vol 12 ◽  
Author(s):  
Sha-Sha Liu ◽  
Li Yang ◽  
Fan-Dong Kong ◽  
Jia-Hui Zhao ◽  
Li Yao ◽  
...  
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Spodoptera Frugiperda ◽  
Quantum Chemical ◽  
Spectroscopic Data ◽  
Chemical Shifts ◽  
Indole Alkaloids ◽  
Amide Group ◽  
Activation Effect ◽  
Aspergillus Sp ◽  
New Compounds

By feeding tryptophan to the marine-derived fungus Aspergillus sp. HNMF114 from the bivalve mollusk Sanguinolaria chinensis, 3 new quinazoline-containing indole alkaloids, named aspertoryadins H–J (1–3), along with 16 known ones (4–19), were obtained. The structures of the new compounds were elucidated by the analysis of spectroscopic data combined with quantum chemical calculations of nuclear magnetic resonance (NMR) chemical shifts and electron capture detector (ECD) spectra. Structurally, compound 3 represents the first example of this type of compound, bearing an amide group at C-3. Compounds 10 and 16 showed potent α-glucosidase inhibitory activity with IC50 values of 7.18 and 5.29 μM, and compounds 13 and 14 showed a clear activation effect on the ryanodine receptor from Spodoptera frugiperda (sfRyR), which reduced the [Ca2+]ER by 37.1 and 36.2%, respectively.

scholarly journals Bioactive Novel Indole Alkaloids and Steroids from Deep Sea-Derived Fungus Aspergillus fumigatus SCSIO 41012

Molecules ◽  
2018 ◽  
Vol 23 (9) ◽  
pp. 2379 ◽  
Author(s):  
Salendra Limbadri ◽  
Xiaowei Luo ◽  
Xiuping Lin ◽  
Shengrong Liao ◽  
Junfeng Wang ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nuclear Magnetic Resonance ◽  
Aspergillus Fumigatus ◽  
Deep Sea ◽  
Spectroscopic Data ◽  
Indole Alkaloids ◽  
Significant Activity ◽  
Inhibitory Activities ◽  
Antibacterial And Antifungal ◽  
Mic Value

Two new alkaloids, fumigatosides E (1) and F (2), and a new natural product, 3, 7-diketo-cephalosporin P1 (6) along with five known compounds (3–5, 7, 8) were isolated from deep-sea derived fungal Aspergillus fumigatus SCSIO 41012. Their structures were determined by extensive spectroscopic data analysis, including 1D, 2D nuclear magnetic resonance (NMR) and mass spectrometry (MS), and comparison between the calculated and experimental electronic circular dichroism (ECD) spectra. In addition, all compounds were tested for antibacterial and antifungal inhibitory activities. Compound 1 showed significant antifungal activity against Fusarium oxysporum f. sp. momordicae with MIC at 1.56 µg/mL. Compound 4 exhibited significant higher activity against S. aureus (16,339 and 29,213) with MIC values of 1.56 and 0.78 µg/mL, respectively, and compound 2 exhibited significant activity against A. baumanii ATCC 19606 with a MIC value of 6.25 µg/mL.

scholarly journals Verruculosins A–B, New Oligophenalenone Dimers from the Soft Coral-Derived Fungus Talaromyces verruculosus

Marine Drugs ◽  
2019 ◽  
Vol 17 (9) ◽  
pp. 516 ◽  
Author(s):  
Minghui Wang ◽  
Longhe Yang ◽  
Liubin Feng ◽  
Fan Hu ◽  
Fang Zhang ◽  
...  
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Spectroscopic Data ◽  
Soft Coral ◽  
Optical Rotation ◽  
Tyrosine Phosphatase ◽  
X Ray ◽  
X Ray Crystallography ◽  
Lead Compounds ◽  
Ic50 Values ◽  
New Compounds

In an effort to discover new bioactive anti-tumor lead compounds, a specific tyrosine phosphatase CDC25B and an Erb family receptor EGFR were selected as drug screening targets. This work led to the investigation of the soft coral-derived fungus Talaromyces verruculosus and identification of two new oligophenalenone dimers, verruculosins A–B (1–2), along with three known analogues, bacillisporin F (3), duclauxin (4), and xenoclauxin (5). Compound 1 was the first structure of the oligophenalenone dimer possessing a unique octacyclic skeleton. The detailed structures and absolute configurations of the new compounds were elucidated on the basis of spectroscopic data, X-ray crystallography, optical rotation, Electronic Circular Dichroism (ECD) analysis, and nuclear magnetic resonance (NMR) calculations. Among which, compounds 1, 3, and 5 exhibited modest inhibitory activity against CDC25B with IC50 values of 0.38 ± 0.03, 0.40 ± 0.02, and 0.26 ± 0.06 µM, respectively.

Benzamidinium benzoates

1990 ◽  
Vol 55 (2) ◽  
pp. 460-468 ◽  
Author(s):  
Jiří Krechl ◽  
Svatava Smrčková ◽  
Josef Kuthan
Keyword(s):  
Quantum Chemical ◽  
Spectroscopic Data ◽  
Nmr Spectra ◽  
Mutual Influence ◽  
Chemical Shifts ◽  
Aliphatic Compounds ◽  
C Nmr

Various p-substituted benzamidinium benzoates (III), and benzamidinium p(m)-substituted benzoates (IV) were prepared and the nature of the amidinium - carboxylate interactions was examined by 1H and 13C NMR spectra. Based on the simple semiempirical quantum-chemical EHT method a presumption was made that the mutual influence between both counter-partners is substantially stronger compared to similar aliphatic compounds. The spectroscopic data are consistent with this presumption and exhibit good correlation between chemical shifts and Hammett's σ values.

scholarly journals Applications of artificial intelligence to structure determination of organic compounds. XX*. Determination of groups attached to the skeleton of natural products using13C nuclear magnetic resonance spectroscopy

1997 ◽  
Vol 13 (3) ◽  
pp. 191-200 ◽  
Author(s):  
Gilberto do V. Rodrigues ◽  
Ivan P. de Arruda Campos ◽  
Vicente de P. Emerenciano
Keyword(s):  
Artificial Intelligence ◽  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Natural Product ◽  
Spectroscopic Data ◽  
Chemical Shifts ◽  
Resonance Spectroscopy ◽  
Initial Dataset ◽  
C Nmr

A procedure for the identification of substituent groups (viz. angelate, tiglate, etc.) attached to any of the atoms in the conventional skeleton of a natural product is described. It consists in the use of the program MACRONO, which was developed for finding subspectra due to the carbons in the said substituent groups amid the raw13C NMR spectroscopic data from any given natural product (by means of comparisons of all possible subsets of the observed chemical shifts with those contained in an apposite database, built with literature13C NMR spectroscopic data regarding those groups). This procedure enables one to expunge the chemical shifts not due to skeletal carbons from the initial dataset, which then can be input to the expert system SISTEMAT, for skeletal identification.

Synthesis, Characterization, and Modelling of Novel Multifunctional Acryloyl-Based Monomers: An Experimental and Computational Study

2002 ◽  
Vol 55 (10) ◽  
pp. 675 ◽  
Author(s):  
Georgia Patras ◽  
Greg G. Qiao ◽  
David H. Solomon ◽  
Rainer Koch
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Nmr Spectroscopy ◽  
Magnetic Resonance ◽  
Quantum Chemical ◽  
Nmr Spectra ◽  
Computational Study ◽  
Chemical Shifts ◽  
13C Nmr Spectra ◽  
Nmr Spectrum ◽  
Reactive N

Several novel multifunctional monomers with at least three reactive N-acryloyl double bonds have been synthesized and fully characterized. Quantum-chemical calculations and nuclear magnetic resonance (NMR) spectroscopy have been used to predict the structural dissymmetry of these monomers: the simulation of conformers and the NMR spectrum of monomer (3) allows the explanation of the observed 13C NMR spectra as well as a comparison of the performance of several methods for calculating chemical shifts.

The High Resolution NMR Spectra of Pesticides. II. The DDT-Type Compounds

1969 ◽  
Vol 52 (5) ◽  
pp. 1074-1092 ◽  
Author(s):  
L H Keith ◽  
A L Alford ◽  
A W Garrison
Keyword(s):  
Nuclear Magnetic Resonance ◽  
High Resolution ◽  
Nmr Spectra ◽  
Chemical Shifts ◽  
Coupling Constants ◽  
Aromatic Rings ◽  
Nuclear Magnetic Resonance Spectra ◽  
High Resolution Nmr ◽  
Related Compounds ◽  
Deshielding Effect

Abstract The high resolution nuclear magnetic resonance spectra of the DDT class of pesticides and related compounds are discussed, including a study of the resonances of the aromatic protons as they are affected by various substiluents. The CCl3 moiety on the α-carbon strongly deshields the ortho protons on the aromatic rings, and this deshielding effect is greatly enhanced by substitution of a chlorine ortho rather than para on the aromatic ring. These deshielding effects are explained by a consideration of the electronegativity of the substituents and the stereochemistry of the molecule. The chemical shifts and coupling constants are tabulated.

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