scholarly journals The Issue of Misidentification of Kojic Acid with Flufuran in Aspergillus flavus

Molecules ◽  
2019 ◽  
Vol 24 (9) ◽  
pp. 1709 ◽  
Author(s):  
Marina DellaGreca ◽  
Gaetano De Tommaso ◽  
Maria Michela Salvatore ◽  
Rosario Nicoletti ◽  
Andrea Becchimanzi ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Aspergillus Flavus ◽  
13C Nmr ◽  
Spectroscopic Data ◽  
Kojic Acid ◽  
Uv Spectra ◽  
Complex Phenomenon ◽  
Metabolomic Profile ◽  
The Past ◽  
Bee Decline

In the course of investigations on the complex phenomenon of bee decline, Aspergillus flavus was isolated from the haemocoel of worker bees. Observations on the metabolomic profile of this strain showed kojic acid to be the dominant product in cultures on Czapek-Dox broth. However, an accurate review of papers documenting secondary metabolite production in A. flavus also showed that an isomer of kojic acid, identified as 5-(hydroxymethyl)-furan-3-carboxylic acid and named flufuran is reported from this species. The spectroscopic data of kojic acid were almost identical to those reported in the literature for flufuran. This motivated a comparative study of commercial kojic acid and 5-(hydroxymethyl)-furan-3-carboxylic acid, highlighting some differences, for example in the 13C-NMR and UV spectra for the two compounds, indicating that misidentification of the kojic acid as 5-(hydroxymethyl)-furan-3-carboxylic acid has occurred in the past.

scholarly journals Lampiran 1F Paper Single production of Kojic acid by Aspergillus flavus and the revision of flufuran

2021 ◽  
Author(s):  
Philiphi de Rozari
Keyword(s):  
Aspergillus Flavus ◽  
Endophytic Fungi ◽  
Catharanthus Roseus ◽  
Spectroscopic Data ◽  
Kojic Acid ◽  
Annona Squamosa ◽  
Nmr Data ◽  
Toxic Metabolites ◽  
Single Production ◽  
Industrial Use

Timor Island is very hot and dry due to the high intensity of sunlight experienced throughout the year. The endophytic fungi Aspergillus flavus had been isolated from medicinal plants such as Catharanthus roseus, Annona squamosa and Curcuma xanthorisa. The endophytic fungi A. flavus from each plant was cultivated on solid rice media and then analyzed for its capability for producing kojic acid. The production of kojic acid was analyzed by HPLC; the highest amount of kojic acid was observed from the endophytic fungi A. flavus, isolated from the stem of Catharanthus roseus, followed by A. flavus from Annona squamosa and Curcuma xanthorisa. Simple VLC fractionation of the extract of A. flavus from C.roseus led to the isolation of around 11.1 g of pure kojic acid. The structure of kojic acid (1) was confirmed by NMR and MS spectroscopic data. A comparison of the NMR data with the literature supported the revision of the natural product flufuran to kojic acid. To the best of our knowledge, this is the first report of a strain of endophytic fungi producing only kojic acid without any other toxic metabolites such as alfatoxins. Therefore, this Aspergillus flavus strain can be applied as a potential producer of kojic acid for industrial use.

scholarly journals Single Production of Kojic Acid by Aspergillus flavus and the Revision of Flufuran

Molecules ◽  
2019 ◽  
Vol 24 (22) ◽  
pp. 4200 ◽  
Author(s):  
Antonius R. B. Ola ◽  
Gema Metboki ◽  
Caterina S. Lay ◽  
Yoseph Sugi ◽  
Philipi De Rozari ◽  
...  
Keyword(s):  
Aspergillus Flavus ◽  
Endophytic Fungi ◽  
Catharanthus Roseus ◽  
Spectroscopic Data ◽  
Kojic Acid ◽  
Annona Squamosa ◽  
Nmr Data ◽  
Toxic Metabolites ◽  
Single Production ◽  
Industrial Use

Timor Island is very hot and dry due to the high intensity of sunlight experienced throughout the year. The endophytic fungi Aspergillus flavus had been isolated from medicinal plants such as Catharanthus roseus, Annona squamosa and Curcuma xanthorisa. The endophytic fungi A. flavus from each plant was cultivated on solid rice media and then analyzed for its capability for producing kojic acid. The production of kojic acid was analyzed by HPLC; the highest amount of kojic acid was observed from the endophytic fungi A. flavus, isolated from the stem of Catharanthus roseus, followed by A. flavus from Annona squamosa and Curcuma xanthorisa. Simple VLC fractionation of the extract of A. flavus from C.roseus led to the isolation of around 11.1 g of pure kojic acid. The structure of kojic acid (1) was confirmed by NMR and MS spectroscopic data. A comparison of the NMR data with the literature supported the revision of the natural product flufuran to kojic acid. To the best of our knowledge, this is the first report of a strain of endophytic fungi producing only kojic acid without any other toxic metabolites such as alfatoxins. Therefore, this Aspergillus flavus strain can be applied as a potential producer of kojic acid for industrial use.

scholarly journals Kojic Acid Derivatives and Sesquiterpenes from the Aspergillus flavus GZWMJZ-288, A Fungal Endophyte of Garcinia multiflora

2018 ◽  
Vol 13 (11) ◽  
pp. 1934578X1801301 ◽  
Author(s):  
Yanchao Xu ◽  
Liping Wang ◽  
Qianyu Gong ◽  
Guoliang Zhu ◽  
Chunmao Yuan ◽  
...  
Keyword(s):  
Aspergillus Flavus ◽  
Endophytic Fungus ◽  
Spectroscopic Data ◽  
Kojic Acid ◽  
Fungal Endophyte ◽  
Solid Culture ◽  
First Report ◽  
Naturally Occurring ◽  
New Compounds

One new kojic acid dimer, dikojiacid A (1), one new naturally occurring kojic acid dimer, dikojiacid B (2), one new sesquiterpene, 12-hydroxy-8-ene-3-oxodrimenol (6), as well as three known kojic acid derivatives (3–5) and five sesquiterpenes (7–11) were isolated from a solid culture of the endophytic fungus Aspergillus flavus GZWMJZ-288 with Garcinia multiflora. The structures of the new compounds were determined on the basis of spectroscopic data and ECD calculation. This is the first report for the natural kojic acid dimers by which Aspergillus flavus GZWMJZ-288 avoids the injury from acetaldehyde.

scholarly journals PhI(OTf)2 Does Not Exist (Yet)

2020 ◽  
Author(s):  
Sevan D. Houston ◽  
Lachlan Sharp-Bucknall ◽  
Mohammad Albayer ◽  
Jason Dutton ◽  
Tania _
Keyword(s):  
Spectroscopic Data ◽  
The Past

PhI(OTf)2 has been used for the past 30 years as a strong I(III) oxidant for organic and inorganic transformations. It has been reported to be generated in situ from the reactions of either PhI(OAc)2 or PhI=O with two equivalents of TMS-OTf. In this report it is shown that neither of these reactions generate a solution with spectroscopic data consistent with PhI(OTf)2 and thus this compound should not be invoked as the species acting as the oxidant for transformations that have been associated with its use

scholarly journals Structure Elucidation of an Pentacyclic Triterpenoid and Phenolic from Steam Bark of Vitex Pubescens Vahl

2019 ◽  
Vol 1 (1) ◽  
pp. 68-74
Author(s):  
Lenny Anwar
Keyword(s):  
1H Nmr ◽  
13C Nmr ◽  
Betulinic Acid ◽  
Spectroscopic Data ◽  
Structure Elucidation ◽  
Stem Bark ◽  
Hydroxybenzoic Acid ◽  
Pentacyclic Triterpenoid ◽  
Reported Data ◽  
First Time

Pentacyclic triterpenoid, betulinic acid (1) and phenolic, p-hydroxybenzoic acid (2), had been isolated for the first time from the stem bark of Vitex pubescens Vahl. The structure of compounds 1 and 2 was determined based on the interpretation of spectroscopic data including UV, IR, NMR (1H-NMR, 13C-NMR, HMQC, HMBC, COSY) and MS, as well as by comparison with those reported data.

Base-catalyzed Degradations of Carbohydrates. IV. Formation of 2,3-Anhydro-2-methoxy-α-D-allopyranose Derivatives from 3-Deoxy-D-erythro-hex-2-enopyranoses

1973 ◽  
Vol 51 (3) ◽  
pp. 394-401 ◽  
Author(s):  
G. O. Aspinall ◽  
R. R. King
Keyword(s):  
Spectroscopic Data ◽  
Kojic Acid ◽  
Major Product ◽  
A Minor

1,4,6-Tri-O-acetyl-3-deoxy-2-O-methyl-α-D-erythro-hex-2-enopyranose (4) reacts with m-chloroperbenzoic acid to give the epoxide, 1,4,6-tri-O-acetyl-2,3-anhydro-2-methoxy-α-D-allopyranose (6), as the major product together with the perester, 4,6-di-O-acetyl-1,2-O-(1′-m-chloroperbenzoyloxy-ethylidene)-2-methoxy-α-D-glucopyranose (5), as a minor product. The structures of these novel compounds have been assigned on the basis of spectroscopic data and of transformations (i) to kojic acid diacetate and (ii) by oxidative degradations to substituted aldopentonolactones. Further examination of the products of the reaction of 1-O-acetyl-3-deoxy-2,4,6-tri-O-methyl-α-D-erythro-hex-2-enopyranose (1) with m-chloroperbenzoic acid has shown that the epoxide, 1-O-acetyl-2,3-anhydro-2-methoxy-4,6-di-O-methyl-α-D-allopyranose (15), is formed in addition to the previously characterized perester 2.

The Roles of Gentrification in Creation of Diverse Urbanities of Tokyo

2010 ◽  
Vol 35 (4) ◽  
pp. 20-28
Author(s):  
Darko Radovic
Keyword(s):  
Urban Regeneration ◽  
World City ◽  
Complex Phenomenon ◽  
Cultural Sustainability ◽  
The Past ◽  
The World ◽  
Urban Regulation

This article focuses on the role of gentrification in urban regeneration. It supports calls for a more nuanced approach to understanding of that complex phenomenon, which would include the possibility that some of its forms may represent the much needed transfusion of new and healthy energies into tired urbanities. The examples of gentrification presented in this article indicate that some of the outcomes of certain kinds of gentrification are superior to those generated by “proper”, even well considered and well theorised examples of urban regeneration. Those examples are from Tokyo, the largest and one of the fastest-changing cities in the world. The chosen locations are in the precincts of Nezu and Yanaka, where living connections with the past coexist with practices of the bustling World City, and in vibrant, commercially driven Harajuku. The article advocates locally attuned approaches to cultural sustainability, and careful balancing of gentrification with urban regulation. That may help cities remain, as de Certeau once said, the ‘most immoderate of human texts’.

Influence of pH on Kojic Acid Fermentation by Aspergillus flavus

2000 ◽  
Vol 3 (6) ◽  
pp. 977-982 ◽  
Author(s):  
M. Rosfarizan ◽  
A.B. Ariff . ◽  
M. A. Hassan . ◽  
M.I.A. Karim .
Keyword(s):  
Aspergillus Flavus ◽  
Kojic Acid ◽  
Acid Fermentation ◽  
Influence Of Ph

scholarly journals Two New Isocoumarin Derivatives from an Endophytic Fungi Pestalotiopsis coffeae Isolated from a Mangrove Fishtail Palm

2018 ◽  
Vol 13 (1) ◽  
pp. 1934578X1801300 ◽  
Author(s):  
Zhong Wang ◽  
Peng Fan ◽  
Tong-Dan Xue ◽  
Lin-Lin Meng ◽  
Wen-Bin Gao ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Endophytic Fungi ◽  
Endophytic Fungus ◽  
Spectroscopic Data ◽  
X Ray Diffraction ◽  
X Ray ◽  
Chinese Plant

Two new isocoumarin derivatives, 6,8-dihydroxy-7-methyl-1-oxo-1H-isochromene-3-carboxylic acid (1) and 6,8-dihydroxy-3-methoxy-3,7- dimethyl-isochroman-1-one (2), together with five known compounds (3-7), were isolated from the endophytic fungus Pestalotiopsis coffeae derived from the Chinese plant fishtail palm. The structures of these compounds were determined mainly by analysis of their NMR spectroscopic data. The structure of compound 2 was further confirmed by X-ray diffraction.

scholarly journals Enantiomeric Resolution and Absolute Configuration of a Chiral δ-Lactam, Useful Intermediate for the Synthesis of Bioactive Compounds

Molecules ◽  
2020 ◽  
Vol 25 (24) ◽  
pp. 6023
Author(s):  
Roberta Listro ◽  
Giacomo Rossino ◽  
Serena Della Volpe ◽  
Rita Stabile ◽  
Massimo Boiocchi ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Bioactive Compounds ◽  
Absolute Configuration ◽  
Chiral Center ◽  
Reference Compound ◽  
Enantiomeric Resolution ◽  
Enantiomerically Pure ◽  
X Ray ◽  
The Past ◽  
Configuration Assignment

During the past several years, the frequency of discovery of new molecular entities based on γ- or δ-lactam scaffolds has increased continuously. Most of them are characterized by the presence of at least one chiral center. Herein, we present the preparation, isolation and the absolute configuration assignment of enantiomeric 2-(4-bromophenyl)-1-isobutyl-6-oxopiperidin-3-carboxylic acid (trans-1). For the preparation of racemic trans-1, the Castagnoli-Cushman reaction was employed. (Semi)-preparative enantioselective HPLC allowed to obtain enantiomerically pure trans-1 whose absolute configuration was assigned by X-ray diffractometry. Compound (+)-(2R,3R)-1 represents a reference compound for the configurational study of structurally related lactams.

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