Feeding of [5,5-2H2]-1-desoxy-Image -xylulose and [4,4,6,6,6-2H5]-mevalolactone to a geosmin-producing Streptomyces sp. and Fossombronia pusilla

Spiteller, Dieter; Jux, Andreas; Piel, Jörn; Boland, Wilhelm

Feeding of [5,5-2H2]-1-desoxy-Image -xylulose and [4,4,6,6,6-2H5]-mevalolactone to a geosmin-producing Streptomyces sp. and Fossombronia pusilla

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Datum

2002

Autor:innen

Spiteller, Dieter

Jux, Andreas

Piel, Jörn

Boland, Wilhelm

Publikationstyp

Zeitschriftenartikel

Publikationsstatus

Published

Erschienen in

Phytochemistry. 2002, 61(7), pp. 827-834. ISSN 0031-9422. Available under: doi: 10.1016/S0031-9422(02)00282-0

Zusammenfassung

The biosynthesis of the trisnor sesquiterpenoid geosmin (4,8a-dimethyl-octahydro-naphthalen-4a-ol) (1) was investigated by feeding labeled [5,5-²H2]-1-desoxy-d-xylulose (11), [4,4,6,6,6-2H5]-mevalolactone (7) and [2,2-2H2]-mevalolactone (9) to Streptomyces sp. JP95 and the liverwort Fossombronia pusilla. The micro-organism produced geosmin via the 1-desoxy-d-xylulose pathway, whereas the liverwort exclusively utilized mevalolactone for terpenoid biosynthesis. Analysis of the labeling pattern in the resulting isotopomers of geosmin (1) by mass spectroscopy (EI/MS) revealed that geosmin is synthesized in both organisms by cyclization of farnesyl diphosphate to a germacradiene-type intermediate 4. Further transformations en route to geosmin (1) involve an oxidative dealkylation of an i-propyl substituent, 1,2-reduction of a resulting conjugated diene, and bicyclization of a germacatriene intermediate 13. The transformations largely resemble the biosynthesis of dehydrogeosmin (2) in cactus flowers but differ with respect to the regioselectivity of the side chain dealkylation and 1,2-reduction

Deuterium labeled mevalonate and desoxy-d-xylulose fed to cultures of Streptomyces sp. JP95 (MEP pathway) and the liverwort Fossombronia pusilla (MVA pathway) are incorporated into geosmin. Both organisms produce geosmin along the same biosynthetic sequence from farnesyl diphosphate via cyclization and oxidative dealkylation of an isopropyl substituent.

Fachgebiet (DDC)

570 Biowissenschaften, Biologie

Schlagwörter

Geosmin, Biosynthesis, Desoxy-Image -xylulose, Mevalolactone, Liverwort, Fossombronia pusilla, Streptomyces sp. JP95

Zitieren

ISO 690

SPITELLER, Dieter, Andreas JUX, Jörn PIEL, Wilhelm BOLAND, 2002. Feeding of [5,5-2H2]-1-desoxy-Image -xylulose and [4,4,6,6,6-2H5]-mevalolactone to a geosmin-producing Streptomyces sp. and Fossombronia pusilla. In: Phytochemistry. 2002, 61(7), pp. 827-834. ISSN 0031-9422. Available under: doi: 10.1016/S0031-9422(02)00282-0

BibTex

@article{Spiteller2002Feedi-15553,
  year={2002},
  doi={10.1016/S0031-9422(02)00282-0},
  title={Feeding of [5,5-2H2]-1-desoxy-Image -xylulose and [4,4,6,6,6-2H5]-mevalolactone to a geosmin-producing Streptomyces sp. and Fossombronia pusilla},
  number={7},
  volume={61},
  issn={0031-9422},
  journal={Phytochemistry},
  pages={827--834},
  author={Spiteller, Dieter and Jux, Andreas and Piel, Jörn and Boland, Wilhelm}
}

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    <dcterms:abstract xml:lang="eng">The biosynthesis of the trisnor sesquiterpenoid geosmin (4,8a-dimethyl-octahydro-naphthalen-4a-ol) (1) was investigated by feeding labeled [5,5-²H2]-1-desoxy-d-xylulose (11), [4,4,6,6,6-2H5]-mevalolactone (7) and [2,2-2H2]-mevalolactone (9) to Streptomyces sp. JP95 and the liverwort Fossombronia pusilla. The micro-organism produced geosmin via the 1-desoxy-d-xylulose pathway, whereas the liverwort exclusively utilized mevalolactone for terpenoid biosynthesis. Analysis of the labeling pattern in the resulting isotopomers of geosmin (1) by mass spectroscopy (EI/MS) revealed that geosmin is synthesized in both organisms by cyclization of farnesyl diphosphate to a germacradiene-type intermediate 4. Further transformations en route to geosmin (1) involve an oxidative dealkylation of an i-propyl substituent, 1,2-reduction of a resulting conjugated diene, and bicyclization of a germacatriene intermediate 13. The transformations largely resemble the biosynthesis of dehydrogeosmin (2) in cactus flowers but differ with respect to the regioselectivity of the side chain dealkylation and 1,2-reduction&lt;br /&gt;&lt;br /&gt;Deuterium labeled mevalonate and desoxy-d-xylulose fed to cultures of Streptomyces sp. JP95 (MEP pathway) and the liverwort Fossombronia pusilla (MVA pathway) are incorporated into geosmin. Both organisms produce geosmin along the same biosynthetic sequence from farnesyl diphosphate via cyclization and oxidative dealkylation of an isopropyl substituent.</dcterms:abstract>
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