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Sponge-derived Streptomyces producing isoprenoids via the mevalonate pathway.
J Nat Prod. 2010 Feb 26; 73(2):208-12.JN

Abstract

In the course of our screening program for isoprenoids of marine actinobacterial origin, 523 actinobacterial strains were isolated from marine samples. Actinobacteria usually use the 2-C-methyl-d-erythritol 4-phosphate pathway for the production of primary metabolites, but some have been reported to use the mevalonate (MVA) pathway for the production of isoprenoids as secondary metabolites. 3-Hydroxy-3-methyl glutaryl coenzyme A reductase (HMGR) is a key enzyme and plays an important role in the MVA pathway. Therefore, we screened strains possessing the HMGR gene from the 523 strains mentioned above and also investigated isoprenoid compounds from cultures of strains possessing HMGR genes. As a result, Streptomyces sp. SpC080624SC-11 isolated from a marine sponge, Cinachyra sp., was shown to possess the HMGR gene and produce novel isoprenoids, JBIR-46 (1), -47 (2), and -48 (3). On the basis of extensive NMR and MS analyses, the structures of 1-3 were determined to be phenazine derivatives harboring dimethylallyl moieties. Furthermore, the isoprene units of 2 and 3 were confirmed to be synthesized via the MVA pathway in a feeding experiment using [1-(13)C]acetate.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Izumikawa M
Biomedicinal Information Research Center, Japan Biological Informatics Consortium, 2-4-7 Aomi, Koto-ku, Tokyo 135-0064, Japan.
Khan ST
No affiliation info available
Takagi M
No affiliation info available
Shin-ya K
No affiliation info available

MeSH

AnimalsErythritolHydroxymethylglutaryl-CoA-Reductases, NADP-dependentMarine BiologyMevalonic AcidMolecular StructurePoriferaSequence Homology, Nucleic AcidStreptomycesSugar PhosphatesTerpenes

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

20085309

Citation

Izumikawa, Miho, et al. "Sponge-derived Streptomyces Producing Isoprenoids Via the Mevalonate Pathway." Journal of Natural Products, vol. 73, no. 2, 2010, pp. 208-12.
Izumikawa M, Khan ST, Takagi M, et al. Sponge-derived Streptomyces producing isoprenoids via the mevalonate pathway. J Nat Prod. 2010;73(2):208-12.
Izumikawa, M., Khan, S. T., Takagi, M., & Shin-ya, K. (2010). Sponge-derived Streptomyces producing isoprenoids via the mevalonate pathway. Journal of Natural Products, 73(2), 208-12. https://doi.org/10.1021/np900747t
Izumikawa M, et al. Sponge-derived Streptomyces Producing Isoprenoids Via the Mevalonate Pathway. J Nat Prod. 2010 Feb 26;73(2):208-12. PubMed PMID: 20085309.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Sponge-derived Streptomyces producing isoprenoids via the mevalonate pathway. AU - Izumikawa,Miho, AU - Khan,Shams Tabrez, AU - Takagi,Motoki, AU - Shin-ya,Kazuo, PY - 2010/1/21/entrez PY - 2010/1/21/pubmed PY - 2010/4/1/medline SP - 208 EP - 12 JF - Journal of natural products JO - J Nat Prod VL - 73 IS - 2 N2 - In the course of our screening program for isoprenoids of marine actinobacterial origin, 523 actinobacterial strains were isolated from marine samples. Actinobacteria usually use the 2-C-methyl-d-erythritol 4-phosphate pathway for the production of primary metabolites, but some have been reported to use the mevalonate (MVA) pathway for the production of isoprenoids as secondary metabolites. 3-Hydroxy-3-methyl glutaryl coenzyme A reductase (HMGR) is a key enzyme and plays an important role in the MVA pathway. Therefore, we screened strains possessing the HMGR gene from the 523 strains mentioned above and also investigated isoprenoid compounds from cultures of strains possessing HMGR genes. As a result, Streptomyces sp. SpC080624SC-11 isolated from a marine sponge, Cinachyra sp., was shown to possess the HMGR gene and produce novel isoprenoids, JBIR-46 (1), -47 (2), and -48 (3). On the basis of extensive NMR and MS analyses, the structures of 1-3 were determined to be phenazine derivatives harboring dimethylallyl moieties. Furthermore, the isoprene units of 2 and 3 were confirmed to be synthesized via the MVA pathway in a feeding experiment using [1-(13)C]acetate. SN - 1520-6025 UR - https://www.unboundmedicine.com/medline/citation/20085309/Sponge_derived_Streptomyces_producing_isoprenoids_via_the_mevalonate_pathway_ L2 - https://doi.org/10.1021/np900747t DB - PRIME DP - Unbound Medicine ER -