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| Biosynthesis and identification of volatiles released by the myxobacterium Stigmatella aurantiaca |
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| Author(s): Dickschat JS, Bode HB, Wenzel SC, Muller R, Schulz S |
| Source: CHEMBIOCHEM Volume: 6 Issue: 11 Pages: 2023-2033 Published: NOV 2005 |
| Times Cited: 14 References: 44 |
| Abstract: The volatiles released by agar plate cultures of two strains of the myxobacterium Stigmatella aurantiaca (strains Sg a 15 and DW4/3-1) were collected in a closed-loop stripping apparatus (CLSA) and analyzed by GC-MS. Large numbers of substances from different compound classes (ketones, esters, lactones, terpenes, and sulfur and nitrogen compounds) were identified; several of them are reported from natural sources for the first time. The volatiles 2-methyltridecan-4-one (17), its isomer 3-methyltridecan-4-one (20), and the higher homologue 2-methyltetradecan-4-one (18) were identified in the extracts of both strains and were synthesized. In addition, strain Sg a 75 produced 2,12-dimethyltridecan4-one (79), 2-methyltridec-2-en-4-one (2 3), and a series of phenyl ketones, among them 1-phenyldecan-1-one (14) and 9-methyl-1-phenyldecan-1-one (16), whereas strain DW4/3-1 emitted traces of 10-methylundecan-2-one (21). The biosynthesis of 14 and 16 was examined in feeding experiments with deuterated precursors carried out on agar plate cultures. The leucine-derived starter unit isovalerate was shown to be incorporated into 16, as was phenylalanine-derived benzoic acid into both 14 and 16. The results point to formation both of the phenyl ketones and of the structurally related aliphatic ketones through an unusual head-to-head coupling between a starter unit such as benzoyl-CoA and a forty acyl-CoA, followed by decarboxylation. |
| Document Type: Article |
| Language: English |
| Reprint Address: Schulz, S (reprint author), Tech Univ Carolo Wilhelmina Braunschweig, Inst Organ Chem, Hagenring 30, D-38106 Braunschweig, Germany |
Addresses:
1. Tech Univ Carolo Wilhelmina Braunschweig, Inst Organ Chem, D-38106 Braunschweig, Germany
2. Univ Saarland, Inst Pharmazeut Biotechnol, D-66123 Saarbrucken, Germany |
| Publisher: WILEY-V C H VERLAG GMBH, PO BOX 10 11 61, D-69451 WEINHEIM, GERMANY |
| Subject Category: Biochemistry & Molecular Biology; Chemistry, Medicinal |
| IDS Number: 983LD |
| ISSN: 1439-4227 |
| DOI: 10.1002/cbic.200500174 |
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