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

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.

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Analysis of production kojic acid from endophytic fungi Aspergillus flavus isolated from Annona squamosa leaves using an OSMAC Approach

IOP Conference Series Materials Science and Engineering ◽

10.1088/1757-899x/823/1/012003 ◽

2020 ◽

Vol 823 ◽

pp. 012003

Author(s):

Antonius R B Ola ◽

Yoseph Sugi ◽

Christina A Pada Soa ◽

Reiner I Lerrik ◽

Bibiana D Tawa

Keyword(s):

Aspergillus Flavus ◽

Endophytic Fungi ◽

Kojic Acid ◽

Annona Squamosa

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

Molecules ◽

10.3390/molecules24091709 ◽

2019 ◽

Vol 24 (9) ◽

pp. 1709 ◽

Cited By ~ 3

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.

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

Natural Product Communications ◽

10.1177/1934578x1801301102 ◽

2018 ◽

Vol 13 (11) ◽

pp. 1934578X1801301 ◽

Cited By ~ 1

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.

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Isolation and Characterization of Fungal Endophytes Isolated from Medicinal Plant Ephedra pachyclada as Plant Growth-Promoting

Biomolecules ◽

10.3390/biom11020140 ◽

2021 ◽

Vol 11 (2) ◽

pp. 140 ◽

Cited By ~ 2

Author(s):

Ahmed Mohamed Aly Khalil ◽

Saad El-Din Hassan ◽

Sultan M. Alsharif ◽

Ahmed M. Eid ◽

Emad El-Din Ewais ◽

...

Keyword(s):

Medicinal Plants ◽

Plant Growth ◽

Aspergillus Flavus ◽

Endophytic Fungi ◽

Fungal Endophytes ◽

Penicillium Crustosum ◽

Plant Growth Promoting ◽

Penicillium Commune ◽

Maize Plants ◽

Growth Promoting

Endophytic fungi are widely present in internal plant tissues and provide different benefits to their host. Medicinal plants have unexplored diversity of functional fungal association; therefore, this study aimed to isolate endophytic fungi associated with leaves of medicinal plants Ephedra pachyclada and evaluate their plant growth-promoting properties. Fifteen isolated fungal endophytes belonging to Ascomycota, with three different genera, Penicillium, Alternaria, and Aspergillus, were obtained from healthy leaves of E. pachyclada. These fungal endophytes have varied antimicrobial activity against human pathogenic microbes and produce ammonia and indole acetic acid (IAA), in addition to their enzymatic activity. The results showed that Penicillium commune EP-5 had a maximum IAA productivity of 192.1 ± 4.04 µg mL−1 in the presence of 5 µg mL−1 tryptophan. The fungal isolates of Penicillium crustosum EP-2, Penicillium chrysogenum EP-3, and Aspergillus flavus EP-14 exhibited variable efficiency for solubilizing phosphate salts. Five representative fungal endophytes of Penicillium crustosum EP-2, Penicillium commune EP-5, Penicillium caseifulvum EP-11, Alternaria tenuissima EP-13, and Aspergillus flavus EP-14 and their consortium were selected and applied as bioinoculant to maize plants. The results showed that Penicillium commune EP-5 increased root lengths from 15.8 ± 0.8 to 22.1 ± 0.6. Moreover, the vegetative growth features of inoculated maize plants improved more than the uninoculated ones.

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A 19F, 119Sn nuclear magnetic resonance and 119Sn Mössbauer study of the SnF2–MF–H2O system

Canadian Journal of Chemistry ◽

10.1139/v84-099 ◽

1984 ◽

Vol 62 (3) ◽

pp. 591-595 ◽

Cited By ~ 11

Author(s):

Thomas Birchall ◽

Georges Dénès

Keyword(s):

Nuclear Magnetic Resonance ◽

Spectroscopic Data ◽

Dominant Species ◽

Mössbauer Study ◽

Frozen Solution ◽

Nmr Data ◽

Mössbauer Measurements ◽

Mössbauer Parameters ◽

High Concentrations ◽

Frozen Solutions

19F and 119Sn nmr spectroscopy has been used to study the SnF2–MF–H2O (M = Li+, Na+, K+, Rb+, Cs+, and [NH4]+) system. The nmr data have been supplemented by frozen solution 119Sn Mössbauer measurements. The evidence suggests that the dominant species in the SnF2–H2O system is a hydrated stannous fluoride, probably SnF2•H2O having Mössbauer parameters of δ = 3.46 mm s−1 and Δ = 1.70 mm s−1. When F− is added to these solutions rapid F− exchange occurs with the hydrated SnF2 and the dominant species becomes [SnF3]−. The 119Sn nmr chemical shift of [SnF3]− is ~ −700 ppm from (CH3)4Sn. The 119Sn Mössbauer parameters for frozen solutions of [SnF3]− are δ = ~ 3.1 mm s−1 Δ = 1.9 mm s−1. These spectroscopic data are cation dependent. We could find no strong evidence for high concentrations of [Sn2F5]− in any of these solutions.

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Effect of Aspergillus flavus Fungal Elicitor on the Production of Terpenoid Indole Alkaloids in Catharanthus roseus Cambial Meristematic Cells

Molecules ◽

10.3390/molecules23123276 ◽

2018 ◽

Vol 23 (12) ◽

pp. 3276

Author(s):

Chuxin Liang ◽

Chang Chen ◽

Pengfei Zhou ◽

Lv Xu ◽

Jianhua Zhu ◽

...

Keyword(s):

Suspension Culture ◽

Aspergillus Flavus ◽

Catharanthus Roseus ◽

Indole Alkaloids ◽

Fungal Elicitor ◽

Control Group ◽

Terpenoid Indole Alkaloids ◽

Meristematic Cells ◽

Qrt Pcr ◽

Induction Process

This study reported the inducing effect of Aspergillus flavus fungal elicitor on biosynthesis of terpenoid indole alkaloids (TIAs) in Catharanthus roseus cambial meristematic cells (CMCs) and its inducing mechanism. According to the results determined by HPLC and HPLC-MS/MS, the optimal condition of the A. flavus elicitor was as follows: after suspension culture of C. roseus CMCs for 6 day, 25 mg/L A. flavus mycelium elicitor were added, and the CMC suspensions were further cultured for another 48 h. In this condition, the contents of vindoline, catharanthine, and ajmaline were 1.45-, 3.29-, and 2.14-times as high as those of the control group, respectively. Transcriptome analysis showed that D4H, G10H, GES, IRS, LAMT, SGD, STR, TDC, and ORCA3 were involved in the regulation of this induction process. The results of qRT-PCR indicated that the increasing accumulations of vindoline, catharanthine, and ajmaline in C. roseus CMCs were correlated with the increasing expression of the above genes. Therefore, A. flavus fungal elicitor could enhance the TIA production of C. roseus CMCs, which might be used as an alternative biotechnological resource for obtaining bioactive alkaloids.

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Extraction and Determinationof Chemical Structure from flower Dicholomethane Extract of Catharanthus roseus

International Journal of Pharmaceutical Sciences Review and Research ◽

10.47583/ijpsrr.2021.v68i02.007 ◽

2021 ◽

Vol 68 (2) ◽

Author(s):

Shahin Aziza ◽

Koushik Sahab ◽

Md. Abdus Satter Miac ◽

Md. Hemayet Hossaina

Keyword(s):

Data Analysis ◽

Oleanolic Acid ◽

Catharanthus Roseus ◽

Spectroscopic Data ◽

Chemical Structure

Catharanthus roseus is considered a cooling medicine. Two compounds: ?-sitosterol (1) and 3?-Hydroxy-lup-20 (29)-en-28-oic acid or Oleanolic acid (2) have been isolated from flowers from Dicholoromethane extract of Catharanthus roseus. By different spectroscopic data analysis the structures of the compounds have been established.

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A NEW CYTOTOXIC DOLABELLANE FROM THE INDONESIAN SOFT CORAL Anthelia sp.

Indonesian Journal of Chemistry ◽

10.22146/ijc.21279 ◽

2013 ◽

Vol 13 (3) ◽

pp. 216-220 ◽

Cited By ~ 4

Author(s):

Anggia Murni ◽

Novriyandi Hanif ◽

Junichi Tanaka

Keyword(s):

Mass Spectrometry ◽

Drug Development ◽

Ethyl Acetate ◽

Spectroscopic Data ◽

Soft Coral ◽

Ethyl Acetate Extract ◽

2D Nmr ◽

Cancer Drug ◽

Nmr Data ◽

Anti Cancer

One new dolabellane (1) and two known diterpenoids stolonidiol (2) and clavinflol B (3) have been isolated from the ethyl acetate extract of the Indonesian soft coral Anthelia sp. A new compound 1 exhibited a moderate cytotoxicity against NBT-T2 cells at 10 µg/mL, while known compounds 2 and 3 showed cytotoxicity at 1 and 0.5 µg/mL, respectively. Structure of the new compound 1 was elucidated by interpretation of NMR spectroscopic data (1D and 2D NMR data) and mass spectrometry (ESIMS data) as well as comparison with those of related ones. This finding should be useful for anti cancer drug development of the promising dolabellane-types compound.

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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

Canadian Journal of Chemistry ◽

10.1139/v73-058 ◽

1973 ◽

Vol 51 (3) ◽

pp. 394-401 ◽

Cited By ~ 17

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.

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