Microbial transformation of the labdanes, cis-abienol and sclareol.

Abstract

The microbial transformation of ds-abienol and sclareol by a recently isolated soil bacterium, JTS-131, was studied. In the presence of metabolic inhibitors, three newcompoundswere isolated from the culture broth as degradation products of cw-abienol. They were determined to be (12Z)labda-12,14-dien-18-ol, (12Z)-labda-12,14-dien-18-oic acid and its methylester. Two new compounds were also formed from sclareol in the presence of metabolic inhibitors. They were determined to be 13/Miydroxylabd-14-en-18-oic acid and 13/?-hydroxylabd-14-en-18-oic acid methylester. As a result of sequence determination experiments, the biotransformation pathways of cw-abienol and sclareol by the bacterium were proposed. During the course of our studies on the microbial transformation of terpenoids, several new compounds were obtained as biotransformation products.1~3) In previous papers,2'3* we described products formed from m-abienol and sclareol, and their transformation pathways, by the bacterium JTS-162. This report describes the isolation of a new ds-abienol-utilizing bacterium, JTS-131, and the identification of transformation products produced from both e/s-abienol and sclareol by this bacterium. Pathways for these metabolic transformations are also proposed. Taxonomic studies on the bacterium JTS-131 will be reported elsewhere. MATERIALS AND METHODS Chemicals. c/s-Abienol was prepared from Canada fir balsam (Tanarome, Ltd., Montreal, Canada) according to the method described previously.2* Sclareol was provided by Takasago Perfumery Co., Tokyo. The other chemicals used were commercial products of reagent grade. Culture media. Medium-A,the basal mediumfor the metabolic studies, was an aqueoussolution containing 0.2% (NH4)2SO4,

Isolation, Chemical, and Biotransformation Routes of Labdane-type Diterpenes

“…It was also observed that Fusarium lini converted sclareol into 1β-hydroxysclareol ( 381 ) and (12 S )-12-hydroxysclareol ( 382 ) in 1.3% and 1% yield, respectively (Table ) . In 1983, Hieda and co-workers found that the microorganism Rhodococcus erythropolis JTS-131 produces two exclusive products from sclareol, 13β-hydroxylabd-14-en-18-oic acid ( 379 ) and 13β-hydroxylabd-14-en-18-oic acid methyl ester ( 380 ), in about 2 days (Table ) …”

“…142 In 1983, Hieda and co-workers found that the microorganism Rhodococcus erythro- a The partially purified metabolites were acetylated using standard conditions to afford products 396 and 397. polis JTS-131 produces two exclusive products from sclareol, 13β-hydroxylabd-14-en-18-oic acid (379) and 13β-hydroxylabd-14-en-18-oic acid methyl ester (380), in about 2 days (Table 2). 143…”

Microbial transformation of sesquitepenoid ketone, (+) Nootkatone by <i>Macrophomia phaseolina</i>

“…Terpene skeleton is most favourable for structural modification by microbes. Numerous publications described already microbial transformation of terpenoids (Bock et al, 1988;Bock et al, 2006;Ishida, 2005;Joglekar et al, 1969;Welf-Rainer-Abraham et al, 1986;Hieda et al, 1983).…”

Microbial Transformations of Isocupressic Acid

“…There are no reports concerned with the mammalian metabolism of isocupressic acid ( 1 ). However, microbial transformations have been reported for labdane-diterpenes, including sclareol [labd-14-ene-8α,13β-diol] − and its analogues, , and with ruminal metabolism of isocupressic acid ( 1 ) …”