title: Syntheses of natural 1,3-polyol/α-pyrone and its all stereoisomers to estimate antifungal activities against plant pathogenic fungi.
abstract: All stereoisomers of 1,3-polyol/α-pyrone 1-8 with more than 99% ee were synthesized to estimate the effect of stereochemistry on the antifungal activity. The absolute configuration of natural compound was determined as (6R,2'S,4'R)-2. The eight stereoisomers showed the antifungal activity against plant pathogenic Alternaria alternata Japanese pear pathotype and Colletotrichum lagenarium. The large difference of activity level was not observed between stereoisomers, showing 43-72% of growth ratio against control at 0.5mM. The most potent stereoisomer was (6S,2'S,4'S)-8 and the activity of (6R,2'S,4'S)-1 was weakest against both fungi.
authors: Faculty of Agriculture, Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, Japan; South Ehime Fisheries Research Center, 1289-1 Funakoshi, Ainan, Ehime 798-4292, Japan. Electronic address: syamauch@agr.ehime-u.ac.jp.
authors: Satoshi
authors: S
authors: Yamauchi
authors: Faculty of Agriculture, Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, Japan.
authors: Yasuyoshi
authors: Y
authors: Isozaki
authors: Faculty of Agriculture, Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, Japan.
authors: Hisashi
authors: H
authors: Nishiwaki
authors: Integrated Center for Sciences, Tarumi Station, Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, Japan.
authors: Koichi
authors: K
authors: Akiyama
mesh_terms: D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D020231:Colletotrichum / Q000187:drug effects*; D015394:Molecular Structure; D010944:Plants / Q000382:microbiology*; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism
chemical_list: D000935:Antifungal Agents; D011108:Polymers; D011753:Pyrones; C024617:polyol
keywords: 1,3-Polyol/α-pyrone; 5,6-Dihydro-α-pyrone; Antifungal activity