title: Transformation of (±)-lavandulol and (±)-tetrahydrolavandulol by a fungal strain Rhizopus oryzae.
abstract: Biotransformation of an irregular monoterpene alcohol, (±)-lavandulol [(±)-5-methyl-2-(1-methylethenyl)-4-hexen-1-ol] (I) and its tetrahydro derivative, (±)-tetrahydrolavandulol [(±)-2-isopropyl-5-methylhexan-1-ol] (II) were studied using a soil isolated fungal strain Rhizopus oryzae. Five metabolites, 2-((3,3-dimethyloxiran-2-yl)methyl)-3-methylbut-3-en-1-ol (Ia), 2-methyl-5-(prop-1-en-2-yl)hex-2-ene-1,6-diol (Ib), 2-methyl-5-(prop-1-en-2-yl)hexane-1,6-diol (Ic), 2-(3-methylbut-2-enyl)-3-methylenebutane-1,4-diol (Id), 5-methyl-2-(2-methyloxiran-2-yl)hex-4-en-1-ol (Ie) have been isolated from the fermentation medium and characterized with lavandulol as a substrate. When tetrahydrolavandulol used as a substrate, two metabolites 2-isopropyl-5-methylhexane-1,5-diol (IIa) and 2-isopentyl-3-methylbutane-1,3-diol (IIb) have been isolated from the fermentation medium. Biotransformation studies with R. oryzae clearly indicate that the organism initiates the transformation either by hydroxylation at allylic methyl groups or epoxidation of double bond. GC and GCMS analyses indicated that both (R)- and (S)-enantiomers of I and II have been transformed into corresponding hydroxylated or epoxy derivatives, when racemic I and II were used as substrates.
authors.affiliation: Division of Organic Chemistry, National Chemical Laboratory, Council of Scientific and Industrial Research (CSIR), Pune, India.
authors.forename: Pankaj P
authors.initials: PP
authors.lastname: Daramwar
authors.forename: Raju
authors.initials: R
authors.lastname: Rincy
authors.forename: Siddiqui
authors.initials: S
authors.lastname: Niloferjahan
authors.forename: Ramakrishnan
authors.initials: R
authors.lastname: Krithika
authors.forename: Arvind
authors.initials: A
authors.lastname: Gulati
authors.forename: Amit
authors.initials: A
authors.lastname: Yadav
authors.forename: Rakesh
authors.initials: R
authors.lastname: Sharma
authors.forename: Hirekodathakallu V
authors.initials: HV
authors.lastname: Thulasiram
mesh_terms: D000080462:Acyclic Monoterpenes; D001711:Biotransformation; D053858:Metabolic Networks and Pathways; D039821:Monoterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism*; D012233:Rhizopus / Q000378:metabolism*
chemical_list: D000080462:Acyclic Monoterpenes; D039821:Monoterpenes; C492921:lavandulol