Microbial Metabolism of the Diterpene Sclareol: Oxidation of the A Ring by Septomyxa affinis

✍ Scribed by Samir A. Kouzi; James D. McChesney

• Publisher: John Wiley and Sons
• Year: 1990
• Tongue: German
• Weight: 576 KB
• Volume: 73
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19900730811

✦ Synopsis

Microbial metabolism of the diterpene sclareol (1) was studied. Screening studies have shown a number of microorganisms capable of metabolizing 1. Preparative-scale fermentation with Septomyxu uffiniu ATCC 6737 has resulted in the production of three fungal metabolites that have been characterized by 2D-NMR techniques and chemical reactions. These metabolites have been identified as 8~,13p-dihydroxylabd-14-en-3-one (2), labd-14-ene-3p,8~,13B-triol (4), and labd-l4-ene-2c (,8cl,l3P-triol(6).

Introduction. -Sclareol (l), a labdane diterpene ditertiary alcohol, is widely distributed in nature. It was first isolated from the essential oil of Sulviu sclureu L. (Labiatae) in 1931 [l]. Sclareol is a fungal-growth regulator and a plant-growth inhibitor [2-41 and was reported to have a high antibacterial activity [5]. Commercially, sclareol is used as a fixative and natural body in perfumery, as a flavoring agent in the tobacco industry, and as a synthon for the preparation of a series of Ambra odorants in perfumery [6] [7]. The essential oil of Suluiu sclureu L. (clary sage oil) is used extensively as a flavoring component in food products, wine essences, grape flavors and liqueurs, as a fragrance component in soaps, detergents, creams, lotions and tabac-type fragrances in perfumery, as a modifier in spice compounds as well as in folk medicine [8] [9].

Synthesis and the configuration at C(13) of sclareol were studied by Bigley et al.

[lo], and the (13R)-c:onfiguration has been confirmed [Ill. The natural product 1 is a 9:l epimeric mixture at C(13), the (13R)-epimer being the major component [6] [ll]. Naturally occurring A-ring-oxygenated analogs of sclareol are unknown. Functionalization of