Malaysian Journal of Analytical Sciences Vol 21 No 5 (2017): 1156 - 1161

DOI: https://doi.org/10.17576/mjas-2017-2105-19

 

 

 

ISOLATION AND SYNTHESIS OF PINOCEMBRIN AND PINOSTROBIN FROM Artocarpus odoratissimus

 

(Pemencilan dan Sintesis Pinocembrin dan Pinostrobin dari Artocarpus odoratissimus)

 

Nyotia Nyokat1, Khong Heng Yen1*, Ahmad Sazali Hamzah2, Isabel Fong Lim3, Aimi Suhaili Saaidin2

 

1School of Chemistry and Environmental Studies, Faculty of Applied Sciences,

Universiti Teknologi MARA, 94300 Kota Samarahan, Sarawak, Malaysia

2Institute of Science,

Universiti Teknologi MARA, 40450 Shah Alam, Selangor, Malaysia

3Department of Paraclinical Sciences, Faculty of Medicine and Health Sciences,

Universiti Malaysia Sarawak, 94300 Kota Samarahan, Sarawak, Malaysia

 

*Corresponding author:  khonghy@sarawak.uitm.edu.my

 

 

Received: 21 August 2016; Accepted: 27 July 2017

 

 

Abstract

Artocarpus odoratissimus is native to Borneo and Mindanao Island. In Sarawak, it is locally known as Terap. Previous studies showed Artocarpus species are rich in phenolic compounds,  including flavonoids, stilbenoids and arylbenzofurons. The chemical profile of the indigenous plants from Sarawak, such as A. odoratissimus has not been studied intensively and the analyses of medicinal properties have not been explored. Thus, a phytochemical study is carried out on the root extracts of A. odoratissimus using various chromatographic methods and it has led to the isolation of two known flavonoids, namely pinocembrin (1) and pinostrobin (2).  The structures are identified by comparison of their 1H and 13C NMR data with those reported in the literature.  Flavonoid molecule incorporated as multifunctional in the pharmaceutical industry. It has a vast range of pharmacological activities, such as antimicrobial, anti-inflammatory, antioxidant, and anticancer activities. Pinocembrin and pinostrobin which are successfully synthesized with 2-hydroxy,4,6-methoxyacetphenone and benzaldehyde as starting materials were discussed.

 

Keywords:  Artocarpus odoratissimus, terap, pinocembrin, pinostrobin

 

Abstrak

Artocarpus odoratissimus berasal dari Borneo dan Pulau Mindanao. Di Sarawak ia dikenali sebagai Terap. Kajian terdahulu menunjukkan yang spesis Artocarpus kaya dengan sebatian fenolik, termasuk flavonoid, stilbenoid dan arilbenzofuron. Profil kimia tentang tumbuhan yang berasal dari Sarawak, seperti A. odoratissimus masih belum dikaji secara intensif dan analisis tentang khasiat perubatan masih belum lagi diterokai. Oleh itu, kajian fitokimia yang telah dilakukan ke atas krud ekstrak akar  A. odoratissimus dengan menggunakan pelbagai kaedah kromatografi telah berjaya  memencilkan dua sebatian flavonoid, iaitu pinosembrin (1) dan pinostrobin (2).  Bentuk struktur telah dikenal pasti melalui perbandingan data 1H dan 13C NMR dengan kajian literatur. Molekul flavonoid mempunyai pelbagai fungsi di dalam industri farmaseutikal. Ia mempunyai aktiviti farmakologi yang sangat meluas seperti antimikrob, anti-radang, antioksidan, dan antikanser. Pinosembrin dan pinostrobin yang telah berjaya disintesis dengan menggunakan 2-hidroksi,4,6-metoksiasetofenon dan benzaldehid sebagai bahan pemula telah dibincangkan.

 

Kata kunci:  Artocarpus odoratissimus, terap, pinosembrin, pinostrobin

 

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