scholarly journals Microbial Transformation of Curcumol by Aspergillus niger

2013 ◽  
Vol 8 (2) ◽  
pp. 1934578X1300800
Author(s):  
Chen Li-Xia ◽  
Zhang Hui ◽  
Zhao Qian ◽  
Yin Shi-Yu ◽  
Zhang Zhong ◽  
...  
Keyword(s):  
Quality Control ◽  
Natural Products ◽  
Aspergillus Niger ◽  
Essential Oil ◽  
Microbial Transformation ◽  
2D Nmr ◽  
Transformation Product ◽  
Spectroscopic Methods ◽  
Antiviral Effects ◽  
Major Transformation

Curcumol is a representative index component for the quality control of the essential oil of Curcuma wenyujin Y.H. Chen et C. Ling, an antivirus and anticancer drug in China. Microbial transformation of curcumol (1) by Aspergillus niger AS 3.739 yielded two products. Their structures were elucidated as 3α-hydroxycurcumol (2) and 3α-(4′-methoxy-succinyloxy)-curcumol (3) by extensive spectroscopic methods including 2D-NMR and HRESI-MS. Among them, 3 is a new compound. Esterification of the substrate with succinic acid is a novel reaction in the field of microbial transformation of natural products. Compound 2, the major transformation product of 1, was a high regio- and stereo-specific hydroxylation product and showed significant antiviral effects.

Extractives of fungi. V. Microbial transformation products of piperitone

1973 ◽  
Vol 26 (4) ◽  
pp. 845 ◽  
Author(s):  
EV Lassak ◽  
JT Pinhey ◽  
BJ Ralph ◽  
T Sheldon ◽  
JJH Simes
Keyword(s):  
Aspergillus Niger ◽  
Microbial Transformation ◽  
Transformation Products ◽  
Transformation Product ◽  
Major Transformation ◽  
A Minor

The products obtained from the transformation of (�)-piperitone (1) by Pro-actinomyces roseus, a species of Fusarium, and Aspergillus niger have been examined. Major transformation products include (�)-trans-6- hydroxy-p-menth-1-en-3-one (2) and (�)-7-hydroxy-p-menth-1-en-3-one (3); a minor transformation product has been tentatively identified as (�)-8-hydroxy-p-menth-1-en-3-one (4).

scholarly journals Microbial Transformation of Calamintha glandulosa Essential Oil by Aspergillus niger

2018 ◽  
Vol 13 (4) ◽  
pp. 1934578X1801300
Author(s):  
Miroslav Novakovic ◽  
Danka Bukvicki ◽  
Vlatka Vajs ◽  
Vele Tesevic ◽  
Slobodan Milosavljevic ◽  
...  
Keyword(s):  
Aspergillus Niger ◽  
Essential Oil ◽  
Silica Gel ◽  
Biological Activities ◽  
Microbial Transformation ◽  
2D Nmr ◽  
Plant Metabolites ◽  
Biotransformation Process ◽  
2D Nmr Spectra ◽  
Main Component

A number of potentially useful compounds with various biological activities can be obtained from plant metabolites by microorganisms. In present research, essential oil of Calamintha glandulosa was subjected to the biotransformation process by mycromicete Aspergillus niger. GC/MS analyses of the original and biotransformed essential oil have revealed six (1–6) biotransformed compounds from one of the main component-limonene and one biotransformed product (7) originating from the less abundant component-thymol. Piperitone epoxide and piperitenone epoxide, the most abundant components of the original oil, were not biotransformed but gave three artefacts (A1, A2, B1) due to the acidic conditions formed in A. niger medium. Compounds 5, 6 as well as 7 have not been previously found as a biotransformation products of limonene (5 and 6) and thymol (7 rebpectively. New uct (5, 6, and 7) together with the artefacts, were isolated by silica gel column chromatography followed by preparative silica gel thin layer chromatography, and their structures were established by a combination of 1D and 2D NMR spectra and GC/MS data. Biotransformation has one more confirmed as useful method, complementary to synthesis, for obtaining different type of molecules.

Nuclear Magnetic Resonance Spectroscopic Behaviour of Some Selective Natural Flavonoids: A Look Through

2020 ◽  
Vol 17 (2) ◽  
pp. 185-196
Author(s):  
Shyamal K. Jash ◽  
Dilip Gorai ◽  
Lalan C. Mandal ◽  
Rajiv Roy
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Natural Products ◽  
Magnetic Resonance ◽  
Hard Core ◽  
2D Nmr ◽  
Vital Role ◽  
Spectral Technique ◽  
Nmr Techniques ◽  
Significant Class ◽  
Nuclear Magnetic

Flavonoids are considered as a significant class of compounds among the natural products, exhibiting a variety of structural skeletons as well as multidirectional biological potentials. In structural elucidations of natural products, Nuclear Magnetic Resonance (NMR) spectroscopy has been playing a vital role; the technique is one of the sharpest tools in the hands of natural products chemists. The present resume deals with hard-core applications of such spectral technique, particularly in structural elucidation of flavonoids; different NMR techniques including 1H-NMR, 13C-NMR, and 2D-NMR [viz. 1H-1H COSY, COLOC, HMBC, HMQC] are described in detail.

scholarly journals A Novel Microbial Zearalenone Transformation through Phosphorylation

Toxins ◽  
2021 ◽  
Vol 13 (5) ◽  
pp. 294
Author(s):  
Yan Zhu ◽  
Pascal Drouin ◽  
Dion Lepp ◽  
Xiu-Zhen Li ◽  
Honghui Zhu ◽  
...  
Keyword(s):  
Microbial Transformation ◽  
Acid Tolerance ◽  
Transformation Product ◽  
The United States ◽  
Corn Silage ◽  
Rrna Gene ◽  
Bacillus Spp ◽  
High Concentrations ◽  
The 16S Rrna Gene ◽  
Bacillus Strains

Zearalenone (ZEA) is a mycotoxin widely occurring in many agricultural commodities. In this study, a purified bacterial isolate, Bacillus sp. S62-W, obtained from one of 104 corn silage samples from various silos located in the United States, exhibited activity to transform the mycotoxin ZEA. A novel microbial transformation product, ZEA-14-phosphate, was detected, purified, and identified by HPLC, LC-MS, and NMR analyses. The isolate has been identified as belonging to the genus Bacillus according to phylogenetic analysis of the 16S rRNA gene and whole genome alignments. The isolate showed high efficacy in transforming ZEA to ZEA-14-phosphate (100% transformation within 24 h) and possessed advantages of acid tolerance (work at pH = 4.0), working under a broad range of temperatures (22–42 °C), and a capability of transforming ZEA at high concentrations (up to 200 µg/mL). In addition, 23 Bacillus strains of various species were tested for their ZEA phosphorylation activity. Thirteen of the Bacillus strains showed phosphorylation functionality at an efficacy of between 20.3% and 99.4% after 24 h incubation, suggesting the metabolism pathway is widely conserved in Bacillus spp. This study established a new transformation system for potential application of controlling ZEA although the metabolism and toxicity of ZEA-14-phosphate requires further investigation.

scholarly journals Fusarins G–L with Inhibition of NO in RAW264.7 from Marine-Derived Fungus Fusarium solani 7227

Marine Drugs ◽  
2021 ◽  
Vol 19 (6) ◽  
pp. 305
Author(s):  
Guangyuan Luo ◽  
Li Zheng ◽  
Qilin Wu ◽  
Senhua Chen ◽  
Jing Li ◽  
...  
Keyword(s):  
Fusarium Solani ◽  
2D Nmr ◽  
Inflammatory Activity ◽  
Raw264.7 Cells ◽  
Spectroscopic Methods ◽  
X Ray ◽  
X Ray Crystallography ◽  
Structure Activity ◽  
Ic50 Values ◽  
New Compounds

Six new fusarin derivatives, fusarins G–L (1–6), together with five known compounds (5–11) were isolated from the marine-derived fungus Fusarium solani 7227. The structures of the new compounds were elucidated by means of comprehensive spectroscopic methods (1D and 2D NMR, HRESIMS, ECD, and ORC) and X-ray crystallography. Compounds 5–11 exhibited potent anti-inflammatory activity by inhibiting the production of NO in RAW264.7 cells activated by lipopolysaccharide, with IC50 values ranging from 3.6 to 32.2 μM. The structure–activity relationships of the fusarins are discussed herein.

scholarly journals 30-Normedicagenic Acid Glycosides from Chenopodium Foliosum

2012 ◽  
Vol 7 (11) ◽  
pp. 1934578X1200701
Author(s):  
Paraskev T. Nedialkov ◽  
Zlatina Kokanova-Nedialkova ◽  
Daniel Bücherl ◽  
Georgi Momekov ◽  
Jörg Heilmann ◽  
...  
Keyword(s):  
Methyl Ester ◽  
Cell Lines ◽  
Interleukin 2 ◽  
Leukemic Cell ◽  
2D Nmr ◽  
Spectroscopic Methods ◽  
Dioic Acid ◽  
Leukemic Cell Lines ◽  
Aerial Parts

Two new glycosides of 30-normedicagenic acid, namely 3- O-[ β-D-glucuronopyranosyl methyl ester]-2 β,3 β-dihydroxy-30-noroleane-12,20(29)-diene-23,28-dioic acid 28- O-β-D-glucopyranosyl ester, and 3- O-β-D-glucopyranosyl-2 β,3 β-dihydroxy-30-noroleane-12,20(29)-diene-23,28-dioic acid, together with the known 3- O-β-glucopyranosyl-2 β,3 β-dihydroxy-30-noroleane-12,20(29)-diene-23,28-dioic acid 28- O-β-glucopyranosyl ester, and 3- O-β-glucuronopyranosyl-2 β,3 β-dihydroxy-30-noroleane-12,20(29)-diene-23,28-dioic acid 28- O-β-glucopyranosyl ester were isolated from the aerial parts of Chenopodium foliosum Asch. The structures of the compounds were determined by means of spectroscopic methods (1D and 2D NMR, UV, IR) and HRMS-ESI. The compounds were tested for cytotoxicity on three leukemic cell lines (BV-173, SKW-3, HL-60). In addition, the saponins showed moderate stimulatory effects on interleukin-2 production in PHA/PMA stimulated Jurkat E6.1 cells.

scholarly journals Antimicrobial Metabolites against Methicillin-Resistant Staphylococcus aureus from the Endophytic Fungus Neofusicoccum australe

Molecules ◽  
2021 ◽  
Vol 26 (4) ◽  
pp. 1094
Author(s):  
Melissa M. Cadelis ◽  
Soeren Geese ◽  
Benedict B. Uy ◽  
Daniel R. Mulholland ◽  
Shara J. van de Pas ◽  
...  
Keyword(s):  
Staphylococcus Aureus ◽  
Antimicrobial Activity ◽  
Natural Products ◽  
Structure Elucidation ◽  
Methicillin Resistant Staphylococcus Aureus ◽  
Inhibitory Concentration ◽  
Spectroscopic Methods ◽  
Methicillin Resistant ◽  
Bioassay Guided Fractionation ◽  
Antimicrobial Metabolites

Antimicrobial bioassay-guided fractionation of the endophytic fungi Neofusicoccum australe led to the isolation of a new unsymmetrical naphthoquinone dimer, neofusnaphthoquinone B (1), along with four known natural products (2–5). Structure elucidation was conducted by nuclear magnetic resonance (NMR) spectroscopic methods, and the antimicrobial activity of all the natural products was investigated, revealing 1 to be moderately active towards methicillin-resistant Staphylococcus aureus (MRSA) with a minimum inhibitory concentration (MIC) of 16 µg/mL.

scholarly journals Phenolic Constituents of Knautia arvensis Aerial Parts

2011 ◽  
Vol 6 (11) ◽  
pp. 1934578X1100601 ◽  
Author(s):  
Jaroslaw Moldoch ◽  
Barbara Szajwaj ◽  
Milena Masullo ◽  
Lukasz Pecio ◽  
Wieslaw Oleszek ◽  
...  
Keyword(s):  
Chlorogenic Acid ◽  
2D Nmr ◽  
Spectroscopic Methods ◽  
Flavone Glycoside ◽  
Aerial Parts ◽  
Dicaffeoylquinic Acid ◽  
Phenolic Constituents ◽  
First Time

A new C-6 flavone glycoside (6), together with seven known compounds, cryptochlorogenic acid (1), chlorogenic acid (2), 2- O- trans-caffeoylhydrocitric acid (3), isovitexin 7-β-D-glucopyranoside (4), 7,4′-dihydroxy-5-methoxyflavone-6- C-β-D-glucopyranoside (5), 3,5- O-dicaffeoylquinic acid (7) and 4,5- O-dicaffeoylquinic acid (8), were isolated from the aerial parts of Knautia arvensis. Their structures were elucidated by extensive spectroscopic methods including 1D- (1H, 13C and TOCSY) and 2D-NMR (DQF-COSY, HSQC, HMBC) experiments, as well as ESIMS analysis. Compounds 1, 3-5 and 8 are reported for the first time in Knautia arvensis.

Flavon- and Flavonolglycosides from Achillea pannonica Scheele

2001 ◽  
Vol 56 (7-8) ◽  
pp. 521-525 ◽  
Author(s):  
Denata Kasaj ◽  
Liselotte Krenn ◽  
Sonja Prinz ◽  
Antje Hüfner ◽  
Shi Shan Yuc ◽  
...  
Keyword(s):  
Methanolic Extract ◽  
2D Nmr ◽  
Flavonoid Glycosides ◽  
Spectroscopic Methods ◽  
Esi Ms ◽  
Aerial Parts ◽  
Nmr Techniques ◽  
Chemotaxonomic Study ◽  
First Time ◽  
C Nmr

The detailed investigation of a methanolic extract of aerial parts of Achillea pannonica SCHEELE. within a chemotaxonomic study led to the isolation of 6 flavonoid glycosides. Besides rutin, apigenin-7-O-glucopyranoside, luteolin-7-O-glucopyranoside, apigenin-7-O-rutinoside and acacetin-7-O-rutinoside, an unusual flavondiglucoside was isolated. Its structure was established by UV, 1HNMR and 13C NMR spectroscopic methods including 2D-NMR techniques and ESI-MS as luteolin-7,4′-O-β-diglucoside. This substance is reported for the first time in the genus Achillea. Chemotaxonomic aspects are discussed briefly

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