Malaysian Journal of Analytical Sciences Vol 25 No 6 (2021): 949 - 958

 

 

 

 

PURIFICATION OF XANTHORRHIZOL AND SCREENING OF SELECTED MICROBES FOR ITS BIOTRANSFORMATION

 

(Penulenan Xantorizol dan Pengesanan Mikrob Terpilih untuk Biotransformasinya)

 

Nurul Iman Aminudin¹*, Nadia Farhana Yahya¹, Zaima Azira Zainal Abidin², Deny Susanti¹, Muhammad Taher³

 

¹Department of Chemistry, Kulliyyah of Science

² Department of Biotechnology, Kulliyyah of Science

International Islamic University Malaysia, 25200 Kuantan, Pahang Darul Makmur, Malaysia

³ Department of Pharmaceutical Technology, Kulliyyah of Pharmacy

International Islamic University Malaysia, P. O. Box 141, 25710 Kuantan, Pahang Darul Makmur, Malaysia

 

*Corresponding author:  nuruliman@iium.edu.my

 

 

Received: 5 September 2021; Accepted: 11 November 2021; Published:  27 December 2021

 

 

Abstract

Xanthorrhizol is a bisabolene-type sesquiterpenoid and is present abundantly in the essential oil of Curcuma xanthorrhiza (temulawak). It was reported to possess various pharmacological activities, including antimicrobial, anti-inflammatory, antioxidant, antihyperglycemic, antihypertensive, and antiplatelet activities. To further evaluate its pharmacological potency based on the structure-activity relationship, a large amount of xanthorrhizol needs to be purified and subjected to chemical synthesis to yield xanthorrhizol analogues. Common approaches to synthesise the analogues are through chemical reactions. Biotransformation utilising microbes as biocatalysts is one of the green alternatives to replace chemical synthesis methods for producing xanthorrhizol analogues. In this study, xanthorrhizol was purified from the crude essential oil by utilising repetitive chromatographic separation and two-step chemical synthesis involving acetylation and hydrolysis reactions. The purification successfully yielded xanthorrhizol with a purity of 98.1%, as indicated by gas chromatography-mass spectrometry (GC-MS) analysis. The structure of xanthorrhizol was also characterised using nuclear magnetic resonance spectroscopy (NMR). Four selected microbes (Aspergillus niger, Streptomyces sp. K1-18, K3-20, and K7-11) were screened for the biotransformation of xanthorrhizol. The results from thin layer chromatography (TLC) and GC-MS showed that only A. niger could biotransform xanthorrhizol into its derivatives.

 

Keywords:  xanthorrhizol, biotransformation, Aspergillus niger, Streptomyces sp., sesquiterpene

 

Abstrak

Xantorizol adalah seskuiterpen jenis bisabolen dan hadir dengan banyak di dalam minyak pati Curcuma xanthorrhiza (temulawak). Ia telah dilaporkan mempunyai pelbagai aktiviti farmakologi termasuk antimikrob, anti-radang, antioksidan, anti-hiperglisemik, anti-hipertensi dan antiplatlet. Untuk menilai lebih lanjut potensi farmakologi berdasarkan hubungan struktur-aktiviti, xantorizol dalam jumlah yang banyak perlu ditulenkan dan perlu melalui kaedah sintesis kimia yang membolehkan analog xantorizol dihasilkan. Pendekatan biasa untuk sintesis analog adalah melalui tindak balas kimia. Biotransformasi menggunakan mikrob sebagai biopemangkin merupakan satu alternatif hijau menggantikan kaedah sinstesis kimia yang boleh menghasilkan analog xantorizol. Dalam kajian ini, xantorizol telah ditulenkan daripada minyak pati mentah menggunakan pemisahan kromatografi berulang dan dua langkah sintesis kimia melibatkan tindak balas asetilasi dan hidrolisis. Proses penulenan telah berjaya menghasilkan xantorizol dengan ketulenan 98.1% seperti ditunjukkan oleh analisis gas-kromatografi-jisim spektrometri (GK-JS). Struktur xantorizol juga telah diperincikan menggunakan resonans magnetik nuklear (RMN) spektroskopi. Empat mikrob terpilih, (Aspergillus niger, Streptomyces sp. K1-18, K3-20 dan K7-11) telah disaring untuk biotransformasi xantorizol. Keputusan kromatografi lapisan nipis (KLN) dan JK-MS telah menunjukkan cuma A. niger berupaya melakukan biotransformasi xantorizol kepada terbitannya.

 

Kata kunci:  xantorizol, biotransformasi, Aspergillus niger, Streptomyces sp., seskuiterpen

 

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