(+)-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.
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
Takeshi
T
Sassa
Hiromichi
H
Kenmoku
Mitsuyoshi
M
Sato
Tetsuya
T
Murayama
Nobuo
N
Kato
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