(+)-Menthol and its hydroxy derivatives, novel fungal monoterpenols from the fusicoccin-producing fungi, Phomopsis amygdali F6a and Niigata 2.
In our search for new fusicoccins of unique diterpene glucosides from Phomopsis amygdali, we found that a fragrant substance was formed in the early stage of fusicoccin fermentation. This fragrant constituent was isolated and identified as (+)-menthol, which is a novel fungal metabolite as the enantiomer of well-known peppermint (-)-menthol. (+)-7-Hydroxymenthol and new (+)-(6S)-hydroxymenthol were also isolated and identified as fungal metabolites. In addition, p-menthanetriol, which has been reported as the first fungal monoterpene from the fungus, was also isolated. The possible biosynthetic relationship of these metabolites is discussed.
Sassa
Takeshi
T
Course of the Science of Bioresources, The United Graduate School of Agricultural Sciences, Iwate University (Yamagata University), Wakaba-cho, Tsuruoka 997-8555, Japan. tsassa@tds1.tr.yamagata-u.ac.jp
Kenmoku
Hiromichi
H
Sato
Mitsuyoshi
M
Murayama
Tetsuya
T
Kato
Nobuo
N
D002247:Carbon Isotopes; D006027:Glycosides / Q000096:biosynthesis; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008610:Menthol / Q000031:analogs & derivatives* / Q000302:isolation & purification / Q000378:metabolism; D003904:Mitosporic Fungi / Q000737:chemistry* / Q000378:metabolism; D039821:Monoterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism; D013237:Stereoisomerism
D002247:Carbon Isotopes; D006027:Glycosides; D039821:Monoterpenes; D008610:Menthol; C007808:fusicoccin