Prediction of Geraniol Bond Mode in Aspergillus niger Linalool Dehydratase – Isomerase

https://doi.org/10.22146/mot.45599

Yelfi Anwar(1), Andrianopsyah Mas Jaya Putra(2), Elvina Dhiaul Iftitah(3), Partomuan Simanjuntak(4), Shirly Kumala(5*)

(1) 1) Doctoral Program, Faculty of Pharmacy, University of Pancasila, Jakarta 2) Faculty of Pharmacy, University of 17 August 1945, Jakarta
(2) 1) Faculty of Pharmacy, University of 17 August 1945, Jakarta 2) Pusat Penelitian Kimia, Lembaga Ilmu Pengetahuan Indonesia
(3) 1) Department of Chemistry, Faculty of Math and Science, University of Brawijaya, Malang 2) Essential Oil Institute, University of Brawijaya, Malang
(4) 1) Biotechnology Research Center, Indonesian Institute of Sciences (LIPI) 2) Faculty of Pharmacy, University of Pancasila, Jakarta
(5) Faculty of Pharmacy, University of Pancasila, Jakarta
(*) Corresponding Author

Abstract


Geraniol is a very valuable aroma chemical and has commonly been used in fragrances and aroma compound. Geraniol biotransformation by Aspergillus niger has been studied. The main bioconversion products obtained from geraniol and liquid culture of A. niger are linalool and alpha-terpineol. Linalool plays a major role in anti-inflammatory, antibacterial and antioxidant activities. This study aims to know the interaction of geraniol in Aspergillus niger enzyme with docking molecular. Comparative modeling of Aspergillus niger enzyme was conducted by means of one of the crystal structure of Linalool Dehydratase – Idomerase (LDI) as a template. The best model of this comparative modeling was then used in docking molecular to investigate geraniol binding mode inactive site enzyme of Aspergillus niger. Inactive site enzyme of Aspergillus niger, geraniol is located with hydrophobic and hydrogen bonds: Amino acid – the amino acids are Asn 105, Arg 96, Lys 112 inactive site - OH with hydrogen bond, Arg 97 inactive site – CH3 with hydrophobic bond and Leu54 inactive site – CH3 with the hydrophobic bond. The distances among pharmacophore respectively are 3,603 A, 6,768 A, and 7,345A. It has higher score (ΔGbind: -3.4 kcal/mol) compared to linalool (ΔGbind: -3.6 kcal/mol). Virtual tethering of linalool with LDI Aspergillus niger enzyme in amino acid Leu120 and Glu118 had been done. The pharmacophore is - OH and methyl C8 group. The distances among pharmacophore respectively are 5,835 Å, 2,52 Å, and 5,32 Å. Virtual tethering of LDI Aspergillus niger enzyme with geraniol has a higher score (ΔGbind: -3.4 kcal/mol) compared to linalool (ΔGbind: -3.6 kcal/mol). It shows that interaction between linalool and LDI Aspergillus niger enzyme is easier to occur than the interaction between geraniol and LDI Aspergillus niger enzyme, geraniol reaction to linalool that occurs is rearrangement reaction.


Keywords


Aspergillus niger; Docking molecular; Geraniol; Linalool Dehydratase-Isomerase; Comparative modeling

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References

Ademark P, Varga A, Medve J, Harjunpää V, Drakenberg T, Tjerneld F, et al. (1998) ‘Soft- wood hemicellulose-degrading enzymes from Aspergillus niger: purification and properties of a ␤-mannanase.’, J Biotechnol, 63, pp. 199–210.

Akbar N. Saxena B. K (2009) ‘Isolation of Geraniol content from various essential oils’, C(1), p. 5890.

Borges KB, Borges WdS, Durán-Patrón R, Pupo MT, Bonato PS, C. I. (2009) ‘Stere- oselective biotransformations using fungi as biocatalysts.’, Tetrahedron Asym, 20, pp. 385–97.

Brodkorb, D. et al. (2010) ‘Linalool Dehydratase-Isomerase , a Bifunctional Enzyme in the Anaerobic Degradation of Monoterpenes * □’, 285(40), pp. 30436–30442.

Cori, O. et al. (1986) ‘Linalool, Geraniol, and Nerol and Their Derivatives’, (15), pp. 1310–1316.

Demyttenaere, J. A. N. C. R. and Willemen, H. M. (1998) ‘Biotransformation of linalool to Furanoid and Pyranoid Linalool Oxides by Aspergillus niger’, 47(6), pp. 1029–1036.

Demyttenaere, J. C. R., Del Carmen Herrera, M. and De Kimpe, N. (2000) ‘Biotransformation of geraniol, nerol and citral by sporulated surface cultures of Aspergillus niger and Penicillium sp.’, Phytochemistry, 55(4), pp. 363–373.

Hegazy, M. E. F. et al. (2015) ‘Microbial biotransformation as a tool for drug development based on natural products from mevalonic acid pathway: A review’, Journal of Advanced Research. Cairo University, 6(1), pp. 17–33.

Hu, S. et al. (2017) ‘Research progress on biotransformation of monoterpenes by Aspergillus niger Monocyclic monoterpenes monoterpenes Monocyclic monoterpenes’, 12(6).

Lüddeke, F. and Harder, J. (2011) ‘Enantiospecifi c ( S ) - ( + ) -Linalool Formation from β -Myrcene by Linalool Dehydratase-Isomerase’, pp. 1–4.

Panin, F. et al. (2002) ‘Anti-inflammatory activity of linalool and linalyl acetate constituents of essential oils’, pp. 721–726.

Parshikov, I. A. and Sutherland, J. B. (2014) ‘The use of Aspergillus niger cultures for biotransformation of terpenoids’, Process Biochemistry. Elsevier Ltd.

Raper KB, F. D. (1965) The genus Aspergillus. Baltimore: Williams & Wilkins;

Shah AA, Hasan F, Hameed A, A. S. (2008) ‘Biological degradation of plastics: a comprehensive review.’, Biotechnol Adv, 26, pp. 246–65.

Shubakov AA, E. E. (2002) ‘Production of polygalacturonases by filamentous fungi Aspergillus niger ACM F-1119 and Penicillium dierckxii ACIM F-152.’, Chem Com- put Sim Butlerov Commun, 2, pp. 65–8.

Takeo Ohta, Yuzo Morimitsu, Yoshihiro Sameshima, T. S. and T. O. (1991) ‘Transformation from Geraniol , Nerol and Their Glucosides into Linalool and -Terpineol during Shochu Distillation’, Fermentation, Journal O F, 72(5), pp. 347–351.

Toniazzo, G. et al. (2005) ‘Biotransformation of (-)beta-pinene by Aspergillus niger ATCC 9642.’, Applied biochemistry and biotechnology, 121–124, pp. 837–44. doi: 10.1385/ABAB:123:1-3:0837.

Ward OP, Qin WM, Dhanjoon J, Ye J, S. A. (2006) ‘Physiology and biotechnology of Aspergillus.’, Adv Appl Microbiol 2006;58:1–75., 58, pp. 1–75.

Yemashova NA, Murygina VP, Zhukov DV, Zakharyantz AA, Gladchenko MA, Appanna V, et al. (2007) ‘Biodeterioration of crude oil and oil derived products: a review.’, Rev Environ Sci Biotechnol, 6, pp. 315–37.

Zengin, H. and Baysal, A. H. (2014) ‘Antibacterial and Antioxidant Activity of Essential Oil Terpenes against Pathogenic and Spoilage-Forming Bacteria and Cell Structure-Activity Relationships Evaluated by SEM Microscopy’, pp. 17773–17798.




DOI: https://doi.org/10.22146/mot.45599

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