C4_C0085 1

ELUCIDATING THE KEY STRUCTURAL FEATURES OF BENZOIC ACID AND ITS DERIVATIVES AS ANTI-FUNGAL AGENTS: QSAR STUDIES Kodchakron Kun-asa ,1 Pharit Kamsri ,1 Apinya Srisupan,1 Auradee Punkvang, 2 Warinthorn Chavasiri, 3 Pornpan Pungpo,1,* 1Department of Chemistry, Faculty of Science, Ubon Ratchathani University, 85 Sthollmark Rd., Warinchamrap, Ubonratchathani 34190, 2Faculty of Liberal Arts and Sciences, Division of Science, University, Nakhon Phanom, 48000, Thailand 3 Natural Products Research Unit, Department of Chemistry, Faculty of Science, , Bangkok 10330, Thailand *e-mail: [email protected]

Abstract: Plant pathogenic fungi are harmful for plant production in Thailand. Plant diseases caused by Alternaria porri and Phytophthora parasitica have been serious problems of the agriculture productions. Benzoic acid is one of the most commonly compounds for anti- fungal agents. Moreover, the benzoic derivatives show potential anti-fungal activity. To evaluate the key structural features relating to anti-fungal activities of benzoic acid and its derivatives, 2D and 3D QSAR approaches using HQSAR and CoMSIA, respectively, are convenient tools to establish correlations between biological activities and various molecular properties. The obtained HQSAR and CoMSIA models using the data sets of Alternaria porri and Phytophthora parasitica are satisfying with the q2 values of 0.53 and 0.61 and 0.82 and 0.63, respectively. Graphic interpretations designed in different QSAR models indicate the structure requirement to improve the anti-fungal activities of the benzoic derivatives. The benzoic derivatives require the small substituent containing the hydrophobic and electron donating property in order to improve their activities. Consequently, the obtained results suggest a structural guideline for design and synthesis of novel compounds which will display a better potency against Alternaria porri and Phytophthora parasitica.

References: 1. Thedpitak N. Anti-phytopathogenic fungal activity of benzoic acid and cinnamic acid derivatives. Master’s thesis, Program in Biotechnology, Faculty of Science, Chulalongkron University 2005 2. Amborabe B-E, Fleurat-Lessard P, Chollet J-F, Roblin G. Plant Physiol Biochem 2002; 40:1051–1060. 3. Kim JH, Campbell BC, Mahoney N, Chan KL, Molyneux RJ, Balajee A. fungal biol 2010; 114, 817-824.

Acknowledgements: This work was supported by Thailand Research Fund (DBG5380006 and RTA53800010). The financial support from Science Achievement Scholarship of Thailand (SAST) to K. Kun-asa is acknowledged. Faculty of Science, Ubon Ratchatani University, LCAC , University of Vienna, ASEA-Uninet, NECTEC are gratefully acknowledged for supporting this research.

Keywords: Plant diseases, CoMSIA, Anti-fungal activity, Alternaria porri , Phytophthora parasitica

© 38th Congress on Science and Technology of Thailand (Abstract)