title: Halogenated benzoate derivatives of altholactone with improved anti-fungal activity.
abstract: Altholactone exhibited the anti-fungal activity with a high MIC value of 128 μg ml(-1) against Cryptococcus neoformans and Saccharomyces cerevisiae. Fifteen ester derivatives of altholactone 1-15 were modified by esterification and their structures were confirmed by spectroscopic methods. Most of the ester derivatives exhibited stronger anti-fungal activities than that of the precursor altholactone. 3-Bromo- and 2,4-dichlorobenzoates (7 and 15) exhibited the lowest minimal inhibitory concentration (MIC) values against C. neoformans at 16 μg ml(-1), while the 4-bromo-, 4-iodo-, and 1-bromo-3-chlorobenzoates (11-13) displayed potent activity against S. cerevisiae with MIC values of 1 μg ml(-1). In conclusion, this analysis indicates that the anti-fungal activity of altholactone is enhanced by addition of halogenated benzoyl group to the 3-OH group.
authors.affiliation: a Department of Biotechnology, Faculty of Science , Mahidol University , Bangkok 10400 , Thailand.|b Mahidol University-Osaka University Collaborative Research Center for Bioscience and Biotechnology, Faculty of Science , Mahidol University , Bangkok 10400 , Thailand.
authors.forename: Jirayut
authors.initials: J
authors.lastname: Euanorasetr
authors.affiliation: b Mahidol University-Osaka University Collaborative Research Center for Bioscience and Biotechnology, Faculty of Science , Mahidol University , Bangkok 10400 , Thailand.
authors.forename: Mayura
authors.initials: M
authors.lastname: Junhom
authors.affiliation: c Department of Clinical Microbiology, Faculty of Medical Technology , Mahidol University , Bangkok 10400 , Thailand.
authors.forename: Srisurang
authors.initials: S
authors.lastname: Tantimavanich
authors.affiliation: d Department of Chemistry, Faculty of Science , Mahidol University , Bangkok 10400 , Thailand.
authors.forename: Onanong
authors.initials: O
authors.lastname: Vorasin
authors.affiliation: d Department of Chemistry, Faculty of Science , Mahidol University , Bangkok 10400 , Thailand.
authors.forename: Bamroong
authors.initials: B
authors.lastname: Munyoo
authors.affiliation: d Department of Chemistry, Faculty of Science , Mahidol University , Bangkok 10400 , Thailand.
authors.forename: Patoomratana
authors.initials: P
authors.lastname: Tuchinda
authors.affiliation: a Department of Biotechnology, Faculty of Science , Mahidol University , Bangkok 10400 , Thailand.|b Mahidol University-Osaka University Collaborative Research Center for Bioscience and Biotechnology, Faculty of Science , Mahidol University , Bangkok 10400 , Thailand.
authors.forename: Watanalai
authors.initials: W
authors.lastname: Panbangred
mesh_terms: D015761:4-Aminopyridine / Q000031:analogs & derivatives / Q000737:chemistry; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001565:Benzoates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D003455:Cryptococcus neoformans / Q000187:drug effects; D004024:Dicyclohexylcarbodiimide / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006846:Hydrocarbons, Halogenated / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D012441:Saccharomyces cerevisiae / Q000187:drug effects; D013237:Stereoisomerism
chemical_list: D000935:Antifungal Agents; D001565:Benzoates; D005663:Furans; D006846:Hydrocarbons, Halogenated; D011753:Pyrones; C459359:altholactone; D004024:Dicyclohexylcarbodiimide; D015761:4-Aminopyridine; C003885:4-dimethylaminopyridine
keywords: Altholactone; Polyalthia crassa; anti-fungal activity; ester derivative; halogenated benzoate