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Microbial Transformation of Calamintha glandulosa Essential Oil by Aspergillus niger

Authorized Users Only
2018
Authors
Novaković, Miroslav
Bukvicki, Danka
Vajs, Vlatka
Tešević, Vele
Milosavljević, Slobodan
Marin, Petar D.
Asakawa, Yoshinori
Article (Published version)
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Abstract
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), respectively. New products (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.

Keywords:
Calamintha glandulosa / Essential oil / Biotransformation / Aspergillus niger.
Source:
Natural Product Communications, 2018, 13, 4, 479-482
Publisher:
  • SAGE Publications
Funding / projects:
  • Micromorphological, phytochemical and molecular investigations of plants - systematic, ecological and applicative aspects (RS-173029)
  • Natural products of wild, cultivated and edible plants: structure and bioactivity determination (RS-172053)
  • Matsumae International Foundation
Note:
  • Supplementary data: https://cer.ihtm.bg.ac.rs/handle/123456789/4448
Related info:
  • Referenced by
    https://cer.ihtm.bg.ac.rs/handle/123456789/4448

DOI: 10.1177/1934578x1801300425

ISSN: 1934-578X

WoS: 000433651900025

Scopus: 2-s2.0-85048122670
[ Google Scholar ]
1
2
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/2294
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - JOUR
AU  - Novaković, Miroslav
AU  - Bukvicki, Danka
AU  - Vajs, Vlatka
AU  - Tešević, Vele
AU  - Milosavljević, Slobodan
AU  - Marin, Petar D.
AU  - Asakawa, Yoshinori
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2294
AB  - 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), respectively. New products (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.
PB  - SAGE Publications
T2  - Natural Product Communications
T1  - Microbial Transformation of Calamintha glandulosa Essential Oil by Aspergillus niger
VL  - 13
IS  - 4
SP  - 479
EP  - 482
DO  - 10.1177/1934578x1801300425
ER  - 
@article{
author = "Novaković, Miroslav and Bukvicki, Danka and Vajs, Vlatka and Tešević, Vele and Milosavljević, Slobodan and Marin, Petar D. and Asakawa, Yoshinori",
year = "2018",
abstract = "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), respectively. New products (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.",
publisher = "SAGE Publications",
journal = "Natural Product Communications",
title = "Microbial Transformation of Calamintha glandulosa Essential Oil by Aspergillus niger",
volume = "13",
number = "4",
pages = "479-482",
doi = "10.1177/1934578x1801300425"
}
Novaković, M., Bukvicki, D., Vajs, V., Tešević, V., Milosavljević, S., Marin, P. D.,& Asakawa, Y.. (2018). Microbial Transformation of Calamintha glandulosa Essential Oil by Aspergillus niger. in Natural Product Communications
SAGE Publications., 13(4), 479-482.
https://doi.org/10.1177/1934578x1801300425
Novaković M, Bukvicki D, Vajs V, Tešević V, Milosavljević S, Marin PD, Asakawa Y. Microbial Transformation of Calamintha glandulosa Essential Oil by Aspergillus niger. in Natural Product Communications. 2018;13(4):479-482.
doi:10.1177/1934578x1801300425 .
Novaković, Miroslav, Bukvicki, Danka, Vajs, Vlatka, Tešević, Vele, Milosavljević, Slobodan, Marin, Petar D., Asakawa, Yoshinori, "Microbial Transformation of Calamintha glandulosa Essential Oil by Aspergillus niger" in Natural Product Communications, 13, no. 4 (2018):479-482,
https://doi.org/10.1177/1934578x1801300425 . .

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