Aromadendrane transformations by Curvularia lunata ATCC 12017

Area of Science:

• Natural Product Chemistry
• Microbial Metabolism
• Organic Synthesis

Background:

• Sesquiterpenes are a diverse class of natural products with various biological activities.
• Hyptis verticillata is a plant source of bioactive compounds, including squamulosone.
• Understanding the microbial transformation of natural products can lead to novel derivatives.

Purpose of the Study:

• To synthesize analogues of the natural sesquiterpene squamulosone.
• To investigate the microbial metabolism of these synthetic analogues using Curvularia lunata.
• To identify novel metabolites and understand the biotransformation pathways.

Main Methods:

• Chemical synthesis of five squamulosone analogues from naturally occurring squamulosone.
• Incubation of synthesized analogues with the fungus Curvularia lunata in two distinct growth media.
• Identification of metabolites using analytical techniques (implied, not explicitly stated).

Main Results:

• Five novel sesquiterpene analogues were synthesized and characterized.
• Curvularia lunata mediated redox reactions on most analogues, converting ketones to alcohols and vice versa.
• Aromadendran-9-one (5) underwent remote hydroxylation, and aromadendra-1,9-diene (6) showed extensive metabolism due to its conjugated diene system.

Conclusions:

• The fungus Curvularia lunata is capable of transforming sesquiterpenes through redox reactions and hydroxylation.
• The metabolic fate of squamulosone analogues is influenced by their functional groups and structural features.
• This study expands the known chemical diversity of squamulosone derivatives through microbial biotransformation.